Loud, booming music filled the darkened room of the nightclub, making conversation difficult for anyone but the person in one’s immediate vicinity. Unfortunately, there was no one in my immediate vicinity as I nursed my drink, alone at the bar, as usual.
The company I worked for, a well established bank in town, had rented the club for the evening to celebrate a merger with a rival financial institution. But as I tended to be something of an introvert, I found myself secluded in a room full of people. It wasn’t that I was ugly, but I was considered somewhat of a geek by my co-workers and the fact was, my friends were few and far between.
It didn’t help that I was still a virgin at 22. Of course, I hotly denied it to everyone around me but I don’t think anyone believed me. The fact was, my list of achievements with girls could be counted on one hand. There was Sylvia, from the comic book club, who I briefly shared an evening making out in the back of her car. That night had ended ignominiously when I had prematurely ejaculated in my pants while kissing her.
And then there was Wendy, who upon discovering my minuscule, pre-pubescent sized boner, broke into gales of laughter and abandoned me in our high school parking lot, horny and ashamed of myself.
So my record with women was hardly something to be proud of. I had resigned myself to a life of solitary exclusion, masturbating at home in my pathetic studio apartment.
My sad self reflection was interrupted by the sudden presence of a person coming up to the bar next to me.
“I’ll get a glass of the Cab,” she said in a cool, commanding voice.
I shivered with instant recognition and my heart skipped a beat. Without turning my head, I knew without a doubt it was my supervisor, Denise.
She had started several months ago and quickly rose through the ranks while I still remained a lowly clerk. She had an authoritative air about her and she was used to getting her way. At 5′ 10″, she towered over me and with her ubiquitous high heels, she was, in fact, a full head taller. I always felt like a fumbling child in her presence, and even though she’d barely said more than a couple words to me during the few months she’d worked at the bank, I was completely intimidated by her.
It wasn’t just the force of her personality. She was stunningly beautiful too, with long, jet black hair that cascaded over her shoulders and down the middle of her back. She had steely blue eyes that took my breath away and made me unable to hold her gaze. But everyone agreed that she was the prettiest woman that had ever worked at the bank and with her cute nose and full, sensuous lips, she could have easily been a model.
Besides being tall and statuesque, she also had a narrow waist and big, impossible-to-ignore breasts. Her full, generous cups seemed to overflow from the restrictive confines of her sheer blouses and there was many a night I had spent, diddling myself as I fantasizing about her and her fabulous body.
As she waiting for her wine, I stared ahead, afraid to look over at her, my heart pounding in my chest and my mouth suddenly dry. Out of my peripheral vision, I could see the slinky black cocktail dress she was wearing, so low cut and revealing that our doddering old fool of a bank manager, Mr. Jenkins, had blushed when he first saw it this evening. At the same time, the female bank workers were looking at her with knives while the males were practically drooling over themselves. The latter group had done everything in their power to get her out on a date but so far, she had rejected them all. I could only speculate what sort of man could live up to her standards but I knew he would have to be incredible.
For my own part, I was content just to stay out of her way and not have her dislike me, at least not overtly.
“What are you drinking?” Denise asked casually.
My heart skipped a beat. Hastily, I looked around, certain she was talking to someone else.
When I could see no other person within shouting distance, I gulped hard and briefly looked up into her crystalline sapphire-blue eyes.
“Um–uh, j-just beer,” I replied lamely.
I instantly hated myself for my abysmal social skills. She must have thought I was the lowliest turd in the room.
And yet, instead of rolling her eyes (as I’d seen her do before), she flashed me an impish smile which only made her look more radiant, if that was even possible.
“You’re name’s Chris, right?” she asked.
I blushed with pride that she actually knew my name, despite the fact we had worked in the same small building for four months together.
“Uh, y-yes,” I stammered, “Hi Denise,” I croaked.
I felt so utterly unworthy of having a conversation with her. My palms were sweating and I felt the eyes of every guy in the room upon us.
Her glass of wine appeared but she ignored it.
“Want to dance?” she asked simply.
I swallowed hard in disbelief.
“M-me?” I stammered as I pointed to myself incredulously.
“I’m not talking to anyone else, am I?” she replied dryly.
I cleared my throat nervously. What was I going to say? No? I would have walked home naked if she had asked me.
“Um, s-sure,” I said uncertainly.
We made our way out to the dance floor and I followed behind like her little puppy. Just watching her walk was an intensely arousing experience, with her perfect buns and the feminine sway of her curvy hips. Gazing at her long, sexy legs, I felt myself getting hard in my pants.
It seemed like I was panting before we even began to dance and I was seeing a side of her I hadn’t seen before. Whereas at the bank, she carried herself with a cool, professional demeanor–here, she was like an exotic dancer, so completely exciting and delicious in every way.
She slid up against me and I shivered with delight. Her dance was tortuously erotic and once again, I could feel the eyes of everyone watching us. I smiled foolishly with pride at being the one that Denise chose to dance with–this was the single most amazing point of my entire life!
As the beat grew slower, she moved up close to me and deliberately ground herself against my thigh. It was all too much for me. I shuddered and abruptly climaxed in my pants.
She immediately sensed a change and she looked at me strangely.
I shook my head and blushed hotly.
“N-nothing, I’m okay,” I lied.
Suddenly, her slim hand reached down and cupped my crotch, feeling the damp spot forming in front. I jerked away like her hand was a red hot poker, ashamed of my pathetic lack of control.
“Chris, did you just cum in your pants?” she asked pointedly, her left eyebrow rising in a show of incredulity.
“No–I-I….” I stammered at a loss for words.
“I better take you home, I think you’ve had more than you can handle for one night.”
I blushed fire engine red and looked down at the floor in shame. Taking me by the hand, she led me past the groups of staring employees who were fortunately ignorant of my shameful deed.
We walked out to the parking lot, Denise leading the way and holding my hand like I was child. I felt so humiliated, having her think I had no more control than a pimply-faced 13 year-old boy.
Opening the door to her Lexus, she pushed me in without giving me a chance to explain myself.
“Really, I-I can drive myself home,” I tried to tell her.
“Oh no, you’re coming home with me,” she said firmly, “I have something you need at my house.”
I couldn’t imagine what she was talking about, but I was relieved that she at least wasn’t laughing at me or scorning me openly in front of our other co-workers.
As she drove us through the darkened city streets, her delicate, manicured hand came to rest on my thigh, which she began to rub softly.
“So…do you find me sexy?” she asked, her voice taking on a sensuous timbre.
“Oh my god–yes,” I replied without equivocation.
“Well, I think you’re kind of cute too, Chrissey,” she said with that impish smile again.
Even though she had used a more feminine form of my name, I could hardly protest because her hand was making it’s way over to my crotch.
“What have you got hiding down in there?” she asked playfully.
I froze with nervousness, afraid of what she would discover. Even when I was fully erect, my penis was no more than two inches–on my best day. Limp, it could barely be referred to as my “manhood”.
“Hmm…” she said as she reached further down, “I’m not finding anything…are you sure you have a cock?” she teased.
I felt the sides of my cheeks burning with shame and my neck getting red as well.
“Y-yes,” I stammered, “it’s-it’s just not, um, very big.”
“Well, I’ll have to take your word for it, cause I’m not finding anything.”
This was mortifying to have to go through again, with her, of all people.
At last, we pulled into her driveway and the humiliating inquiry was interrupted. We got out and went into her house where she gave me a beer from out of her refrigerator. Pouring herself a glass of red wine she instructed me to follow her down the hallway.
“Chrissey, if you’re going to be with me, we’re going to have to take some steps to take care of your little problem.”
I wasn’t sure if she was referring to the size of my penis or my tendency to prematurely ejaculate, neither of which I was very proud of.
Turning to face me, she reached down and began unbuttoning my pants.
“Wha-what are you doing?” I squeaked, suddenly nervous again.
“Look. Let’s get something straight–in this relationship, I make the rules. If you can’t deal with that, you can walk out the door right now and I’ll never speak to you again,” she said defiantly.
The color drained from my face. How could I tell this incredibly gorgeous woman no? How could I deny her anything?
“I…I’m okay with that,” I said meekly.
“Good. I’m glad to hear it,” she said, her voice taking on a bossy tone, “because I have something here that will help your little problem.”
I still didn’t know what she had in mind but I stood there like a child as she unzipped my pants and dropped them to the floor. I shivered as her smooth hands slipped inside my underwear and pulled them down, ignoring the gooey wet spot on the front. She looked at my shriveled member and shook her head, making me blush all over again. I groaned with embarrassment as she reached into her dresser drawer and took out a clear plastic device of some sort.
“I only hope this is small enough,” she said as she took it apart and then put the pieces aside.
Despite my humiliation, I felt myself getting aroused all over again. As she was bending over, I couldn’t help but gaze down the scoop neck of her cocktail dress and stare at the two big twins spilling out of her top. They were truly massive and they pushed up against each other, creating an unbelievably sexy cleavage. As I felt her handling my sack, I started to get erect once more.
“That’s good, keep staring at my breasts, Chrissey,” she said as if reading my mind, “it’ll help me to get your little penis into this device.”
I whimpered as she placed a clear ring around the base of my genitals and with a little lube, began pushing my semi-erect member into a short, cock-shaped tube with a slit at the end.
“Wait–wha-what are you doing?” I asked suddenly apprehensive.
“Something your mommy should have done a long time ago,” she said as she pushed the tube up against the ring to mate it with the pins facing forward. In no time, she took a small lock and slipped it through the hole in front, clicking it closed with an air of finality. My penis, small as it was, felt stuffed into the device and it was now forced into a downward facing angle.
“There, that should take care of that little problem,” she said with a smug look on her face.
“But…but how am I going to get any satisfaction now?” I asked dumbly.
“You’ve already had your satisfaction, and I hope it was good for you because it will be the last orgasm you have for quite a while.”
Before I could protest, she continued without pausing.
“And now, we need to take care of a little unpleasant business. Well…unpleasant for you, that is,” she said with a smirk as she reached into her dresser drawer and pulled out a long rectangular wooden paddle with air holes in it.
“Wait–what are you gonna do?” I quaked nervously as I tried to back away from her.
“This will help you understand who makes the rules in this relationship,” she snapped as she snatched my wrist and yanked me over her sexy lap.
“Wait! Stop!” I cried desperately.
I hadn’t been spanked since my mom caught me masturbating at the age of sixteen. She had quickly reduced me to tears (as she always did) in short order and I didn’t want a repeat here. With the floor only inches from my face, I tried to get up off her lap but she held me in place with steel-like strength.
Denise gripped my shirt firmly with her left hand as her right arm swung up in an avenging arc with the paddle.
“Stop it! Stop it!” I wailed as I kicked my feet frantically.
The paddle swooped down and landed squarely across both my bare cheeks, searing them like a hundred wasp stings.
Another harsh swat landed right where the first one did and I gasped in shock, my eyes bugging out of my head. I struggled mightily against her but nothing I did could extricate myself from her grasp.
A few moments ago, I had been worried about the chastity device but that was the last thing on my mind right now. My eyes filled with tears and I looked down at her high heels, spread a little apart to give her support as she spanked me hard like a naughty little boy.
Her paddle rained down on my defenseless bottom again and again, scalding it and turning it into a flaming sea of crimson welts. I tried to hold back but I couldn’t take it anymore. As her harsh paddle swatted my tender cheeks over and over, I burst into tears and sobbed like a baby.
She kept up her punitive rhythm and I slapped my hands in the floor in frustration and impotence. How could I ever have imagined this is how I would be spending my evening? Why was she punishing me so thoroughly? This was certainly no sensual play spanking, but a blistering paddling that would leave me unable to sit for some time.
Every time I tried to position one of my cheeks away from her attentions, she’d smack it especially hard several times.
Tears were streaming down my face and my nose was running when she finally stopped and let me up. Standing me on my shaky legs, I stamped my feet and rubbed my throbbing, blazing cheeks. For several moments, I just bawled unashamedly in front of her, knowing I looked like nothing more than a defeated, punished child.
She gazed back at me with a look of tremendous satisfaction, a pleased, superior smile on her pretty face.
“Why did you spank me so hard?” I sobbed in bitter frustration.
“So you’d know who wears the pants around here,” she said as she stood up. Reaching her hands out, she took me into her arms and held me close, burying my face into the soft, pillowy cushions of her big breasts. I cried and cried, my chest heaving as she softly stroked my swollen, flaming bottom.
“There, there, baby, get it all out,” she whispered softly in my ear.
Despite the intense, searing pain on my cheeks, it was wonderful to have my nose deep between her beautiful boobs. They smelled fantastic and felt even better against my wet, sobbing face.
For so long, since the first day Denise started working at the bank, I had fantasized about doing just this, although, certainly not under these circumstances.
“And now, it’s time my little sugarplum took care of mommy,” she said with a coy smile.
“And now, it’s time my little sugarplum took care of Mommy,” she said with a coy smile.
Holding my face gently in her slim hands, Denise bent down and gave me a long, slow, sensuous kiss.
I closed my eyes and relaxed, feeling myself helplessly melting in her soft hands. She tasted fabulous and it was obvious she was in no hurry to end our embrace.
I felt so confused! The same beautiful woman that had just paddled my bottom to a five alarm fire and made me cry like a baby was giving me the most passionate kiss of my life!
Although my mind may have been confused, my penis certainly wasn’t. It expanded within the chastity device until it was straining like a Pit Bull against it’s leash. Without thinking, I reached down to alleviate the constriction but could do little other than helplessly grasp my imprisoned wiener in futility. It throbbed with frustration and angst.
Denise reached down and tweaked my nipple, making me groan with desire.
“I have a surprise for you,” she said finally as she ended the kiss and whispered in my ear.
“You-you do?” I asked breathlessly.
I was so worked up and aroused–I wanted her desperately!
“I have a very big surprise for you,” she said, and even though I thought I heard a trace of mirth in her voice, I was so excited, I dismissed it.
“I want you on your knees, Chrissey,” she told me with a provocative smile on her pretty face.
Maybe she wanted me to lick her pussy? If so, I certainly didn’t have any objections. I had never been that close to a woman’s sex before but I figured it couldn’t be that difficult. Presumably, she’d tell me what she wanted if I wasn’t doing it right.
“Um, will you teach me how to do it?” I asked her timidly.
“Oh yes,” she grinned, “I’ll train you to be the very best.”
As I knelt before her on my knees, she took a small object in her hands and pressed a button. I thought I heard some mechanical device being turned on but I couldn’t be sure and as I glanced around the room, I couldn’t see anything apparent.
“What was that?” I asked innocently.
“Don’t you worry your little head about it, Chrissey, you just need to focus on the job ahead of you,” she said, still grinning.
Part of me suspected she had something up her sleeve but I couldn’t imagine what it was, and in any case, I wanted to prove to her I could satisfy her like a man.
“Close your eyes, Chrissey, it’s time for your big surprise,” she instructed me.
Doing as I was told, I knelt in place, not understanding why such a thing would be necessary. I heard her moving a bit and thought I could discern her pulling her panties down her legs. My breathing quickened as I imagined her sex–was it shaved down there? That would be super sexy, I mused.
“Open your mouth, sissy,” she told me, “Nice and wide…wider, Chrissey…that’s it…nice and wide…good boy.”
I heard her giggling and couldn’t imagine what she found so amusing.
“Here you go…just what every sissy boy needs,” she said.
Suddenly, I felt a warm, massive object being pushed into my mouth, quickly filling it to capacity. My eyes shot open and I squealed with shock.
Denise had a fat, gargantuan cock and she had just thrust it deep into my mouth!
I felt her hands firmly holding the back of my head, preventing me from escaping but I struggled anyway.
“Surprise!” she said with a throaty chuckle.
“AWFGH!!!!” I gagged as she pushed her cock all the way in, all the way to my larynx, nearly choking me.
She smiled down on me wickedly, keeping her hands on the back of my head as she pulled her member out a little and then shoved it back in. Each time, I gagged and struggled to breathe through my nose.
“Don’t worry sissy, you’ll be getting plenty of practice. Just use your tongue…that’s it…thaaaat’s it…suck that big lollipop,” she said in a husky voice.
I didn’t want to accommodate her but there was little I could do as she thrust it in and out of my mouth, forcing me to suck her titanic phallus.
“This is right where you belong, on your knees with a big hard cock in your mouth…”
She paused only long enough to moan deliriously.
“Oh yessss…That’s it…show mommy what a good little cocksucker you are…”
I couldn’t believe what I was doing. Was I really sucking my supervisor’s cock right now? On my knees, giving my hot boss a sloppy blowjob?
My lips were wrapped around the slippery shaft of her big, thick cock and she slid it in and out of my warm, wet mouth at a pace of her own choosing.
“More tongue…that’s it…that’s my little sissy…Mommy’s going to teach you to be the best little cocksucker there is…”
Her words were so humiliating to hear, and yet, I felt like I had no choice. I could only hope and pray that if she decided to cum, she’d pull it out of my mouth first.
One time, I had experimented with my own, tasting the strange semen while masturbating and I hadn’t liked it at all.
“Maybe I’ll have you do this to me in the break room at work…would you like that, Chrissey?”
Needless to say, with eight inches of hard cock meat stuffed into my mouth, I was in no position to respond.
Some of her precum was leaking as I sucked on her and the salty taste mixed with my saliva like a lubricant. Her fat shaft was pistoning in and out and a steady stream of drool was dribbling down my chin.
“Get ready sissy…oh…oh…oh-my-god, I’m…I’m about to…” Her voice trailed off.
Her thrusts into my willing mouth were becoming more urgent and I sensed her orgasm was not far off. It felt like she was practically raping my mouth, battering her big pole in and choking me, only to pull it out and thrust it back in again. My head was getting dizzy from all the pounding until she stopped abruptly and held my head tightly in place with both of her hands. The head of her cock was positioned just inside my mouth, with my lips wrapped around the big, bulbous head.
“OHHHHH!!! OH MY GODDD!!!” she shrieked.
I felt her cock swell in my mouth, followed by a huge explosion as she came like a tidal wave. Instantly, my mouth was filled to capacity with hot, creamy semen and I gagged as I struggled to swallow it. No sooner did I gulp it down, when she blew a fresh batch into my mouth, filling it to overflowing. I squealed and shook my hands in the air, desperate to get relief from the mighty cannon my lips were wrapped around. Semen spilled out of the corners of my mouth and dripped down my chin. I tried to back off and get away but she continued to hold my head firmly in her hands, forcing me to take all her cum as she thrust her hard cock all the way in and shot a third load, right down my throat.
All the time, she was gasping for air as she roiled in the throes of her multiple orgasm.
I could hardly breathe and I swallowed again and again, trying to keep up with what seemed like a fire hydrant.
At last, the spasms lessened, and she leaned back against her bed, exhausted, her beautiful blue eyes rolling into the back of her head.
“Oh my god, that felt good…I’ve wanted to cum in your mouth for months now,” she confessed between gasps for breath.
I blushed with humiliation at having willingly sucked a cock and swallowed her massive load of semen, to say nothing of being the object of her pervy desires. My lips and chin were sticky with cum and the inside of my mouth was slick with her semen. Blushing furiously, I swiped my arm across my face even as I subconsciously licked the cum from around the corners of my mouth.
“But it’s true,” she said still trying to catch her breath, “ever since I first saw you in the bank, I’ve pictured you on your knees, with my cock in your mouth–and we both know that’s where you really belong.
“With that tiny little penis of yours, you’re useless as a man, but as a cocksucking sissy, I think you have a very bright future,” she giggled.
Reaching down, she grasped my locked up genitals and gave them a shake.
“And fortunately, we’ve taken care of that little problem,” she smirked, “with emphasis on little.”
I stood up, shaken and upset, my cheeks burning with shame.
“Honestly, you didn’t really think you were ever going to satisfy a woman with that tiny thing, did you?”
Her scorn washed over me and made me want to cry again.
Craning my neck to look up into her pretty and confident face, I felt so completely inferior to her while she stood there, her hands on her hips and looking down at me with that smug, superior expression of hers.
“Aww, come here baby,” she said, taking me in her arms again and using a voice reserved for toddlers. Once more, she pushed my nose into her deep cleavage and held me there, stroking the back of my head tenderly.
“I’m sorry baby, I didn’t mean to hurt your feelings,” she said soothingly, “don’t be upset, okay?”
She reached down and kissed my ear to comfort me.
I was so confused! My emotions were all over the place! In one moment, Denise could be as cruel as my worst enemy, and in the next, loving and warm.
Meanwhile, I breathed in deeply of her feminine scent and savored the wonderful feeling of her big, soft breasts against my face.
“Okay Chrissey, you’ve been through a lot today, I think it’s time you got a little reward,” she said in a seductive voice.
Wondering what she had in mind, I pulled my face away as she took one of her long nailed fingers and pulled the spaghetti strap of her dress aside, letting it fall past her shoulder. As the dress fell away, it revealed the cup of her sexy satin black push-up bra. I licked my lips as she reached between the cups to undo the clasp holding them together.
“Is this what baby wants?” she cooed to me.
I nodded hungrily and she peeled back the cup from her right breast to reveal a big pink aureole and a perky nipple.
“Here sissy, suck from Mommy’s breast,” she urged me.
Since she was so tall, I hardly needed to bend over to accommodate her. I happily wrapped my lips around her warm nipple and suckled, feeling waves of bliss washing over me.
“That’s just what Mommy’s baby needs, hm, sugarplum?” she asked me in a sweet voice.
I nodded and savored the taste of her nipple, reaching up with my right hand to fondle her left breast.
“Nope, hands off sissy, that’s not for you to touch,” she scolded me lightly.
I whimpered but continued enjoying the wonderful nipple in my mouth.
“Hmm…I’m starting to think Mommy needs to get some clothing more appropriate for her baby…like maybe some diapers and plastic pants? What do you think, baby Chrissey? Is that what my little sugarplum needs?”
I shook my head and mumbled no, although it was considerably muffled with her gigantic breast filling my mouth.
“Well…I don’t know Chrissey, I think you’re more of a sissy baby than you’ve led us to believe…I might just have to get some baby clothing for you and dress you up properly.
“One thing’s for sure…I’m taking you off the market so I can have you all to myself,” she said as she beamed down on my blushing face, “I have big plans for you, Chrissey.”
For the next three days at work, Denise practically ignored me. Once, when I tried to talk with her alone in the hallway, she simply brushed me aside and said she was “busy”. I couldn’t understand it. What had I done wrong? Had I not submitted to her completely that first night?
Despite my shock at discovering her anatomy, I still found her incredibly sexy. She still had that gorgeous model-esque face and the big boobs to die for. Every time I thought of suckling from her hard nipples, I swooned.
All week after the night at her house, my heart was doing somersaults–that a woman so totally out of my league would be interested in me, just blew me away. But then, I also couldn’t understand why was she so cool with me at work. It hurt my feelings that she made no acknowledgement of what had happened between us and yet, I couldn’t get her off my mind. I worked at my counter, constantly daydreaming about her. Every time she walked into the room, my heart stopped beating and my eyes followed her every move.
The other issue was, I was beside myself with horniness. I had never gone more than a couple days without being able to masturbate freely and this chastity device of hers was killing me! I had tried everything I could to remove it but it’s design was devilishly made to prevent any kind of escape.
I found myself waking up in the middle of the night, my nighttime erections becoming a source of pain I never thought possible. I found that if I got up and walked around, the budding erection and the associated discomfort would subside, but it was still tremendously frustrating.
I made a vow to demand Denise remove the device the very next time we were alone.
On the other hand, my social standing at the bank had gone up considerably since the party. All the guys thought I was some kind of stud and even the cool ones who never talked to me looked at me in a whole new light. If only they knew I had been on my knees that night, swallowing load after creamy load of Denise’s semen!
I tried to block out that experience but the fact was, I was so horny all the time now, I was willing to put that aspect of her aside. In the big scheme of things, I rationalized that it just wasn’t that important.
But regardless, I didn’t think it was fair for her to ignore me and leave me locked up like this.
Finally, on Friday, I found a brief note left at my counter station along with a stack of checks. It said; ‘Be at my place 9 pm sharp–Denise‘.
I sighed and held the note to my chest, smiling to myself. She did care about me after all.
That night, after a fresh shower and a change into my best shirt and slacks, I showed up Denise’s door with a bouquet of flowers, precisely at 9 pm on the dot. When the door opened, my heart stopped and I was momentarily breathless. She looking absolutely ravishing with her long black hair falling in curls over her bare shoulders and a dark red lipstick on her sensuous lips.
Once again, I was struck by the difference between her attire at work and how she looked when outside of it. She was wearing a black Lycra bustier with a matching skirt and of course, her usual sexy high heels. Around her neck, she wore a thin gold necklace with the key to my chastity device on it, as if taunting me with my freedom.
She gave me a coy smile and then reached down, gently holding my face and planting a long, erotic kiss on my lips that left me panting.
“Hi Chrissey, glad you could make it,” she said with a playful wink, “The flowers are lovely.”
An electric rush rippled through me. I gulped as I drank in her beauty and all the demands and frustrations of the week seemed to evaporate. I had intended to make her remove my device and complain about her ignoring me but now that I was actually face to face with her, my heart was doing cartwheels and I couldn’t find the words. I was just happy to see her smiling at me again–everything else seemed trivial by comparison.
As we went inside, she turned and took me into her arms, pushing my nose into that source of nirvana, her deep cleavage. I sighed and nuzzled, happier than I could ever remember being in my life.
“Did you like nursing from my boobs last time, Chrissey?” she asked softly in my ear.
“Oh yes, that was awesome!” I exclaimed.
“I liked it too,” she replied, “I think you’re just the sweetest little sissy I’ve ever known and for some reason, you bring out the mommy in me.
“How would my baby like to go into my bedroom and nurse again?” she asked.
“Oh yes–for sure!” I replied enthusiastically.
Even though I didn’t like the reference to being a baby, the thought that she saw me as “hers” made my heart swell with pride and joy.
Taking my hand, she led me down the hallway into her large bedroom with it’s four poster king bed. However, as walked through the threshold, I was quick to discover that she had placed several items on the bed, none of which I found welcome.
A thick set of cloth diapers, baby powder, plastic pants and pins lay next to a frilly pink top of some sort. And next to that, was Denise’s fearsome Spencer paddle, ready for immediate use. My heart skipped a beat and I stopped in my tracks.
“Chrissey, I want to dress you up in a cute little outfit I picked out just for you–I know you’ll just love it.”
She beamed at me like she was presenting me with a new car.
“B-but, I’m not a baby,” I protested in a whining voice.
“Oh, I think you’re very babyish,” she immediately replied, “You have a little baby penis, you have an obvious fetish for breastfeeding, and let’s face it, you’re hardly much of a man.”
Once again, her words stung me to the core. It seemed like Denise could go from one extreme to the other in the blink of an eye, from loving to cruel without a second thought.
“But I don’t want to wear diapers!” I complained bitterly.
The fact was, the sight of those diapers and plastic pants brought strong, unpleasant memories of my early teens flooding back, from a time when I had been a habitual bedwetter. My mom had responded by putting me in diapers and plastic pants every night and the practice continued for several years–in fact, pretty much up to the point at which I moved out. I still had the occasional accident in bed but since I had few, if any visitors over to my apartment, I never gave the problem or the associated smell much thought.
And now, Denise wanted to put me back in diapers just like my mom!
“I won’t do it,” I said, but my voice lacked conviction.
The warm smile on Denise’s face vanished, to be replaced by an angry scowl.
“What did I tell you about obeying my instructions?” she snapped as she went over and picked up the paddle, “Do I need to put you over Mommy’s lap again?”
Her voice had taken on a stern edge to it, and the hair went up on the back of my neck.
I gulped nervously and looked around the room in a panic. I didn’t want to blow my relationship with this beautiful babe but I didn’t want to be dressed up like a baby, or be thought of in that way.
And yet, the steely determination in her pretty blue eyes as she held that hard wooden paddle in her hands made my knees weak. I held an instinctive fear of being spanked from my experiences growing up under my strict mother.
And it had taken days for the bruising to go down on my bottom after my last session over Denise’s lap—I wasn’t about to do that again.
“What’s it going to be, Chrissey? A hard spanking–followed by diapers…or just the diapers? It’s up to you,” she said crossing her arms across her impressive chest, her voice as hard as iron.
I felt like I was being scolded by my mom all over again and my will, never very strong, crumbled before this tower of female authority.
“Just-just the diapers, please,” I squeaked.
“That’s better,” she said, sounding smug and superior once again.
Putting the paddle down on the top of her dresser (to my vast relief), she scooped up a large pink pacifier and held it before my mouth.
“Suck on this baby, while Mommy puts you into your diapers.”
I whimpered weakly and reluctantly parted my lips as she pushed it in, the fat rubber nipple filling my mouth and making any kind of coherent speech impossible.
“You are not to remove that under any circumstances, got it?” she demanded.
I nodded my head mutely as she began undoing my pants and taking my shoes off.
What had I gotten myself into? It seemed that every encounter with Denise took me deeper and deeper down the rabbit hole.
Her demeanor changed when my chastised penis came into view and she suddenly giggled to herself.
“And how’s Chrissey’s little pee-pee doing today?” she asked in an amused, condescending tone, “Having difficulty dealing without playing with yourself everyday?”
Even though it was humiliating to admit to her charge, I nodded my head, hoping the admission would grant me some leniency from her.
“Better get used to it, Sissy, your days of masturbating are long gone.”
I winced and gritted my teeth in frustration.
As she pulled my freshly ironed shirt off of me, I wanted to ask when she planned to unlock my plastic prison but the pacifier stuffed into my mouth only garbled my words. I tried again but she just dismissed my babbling by shushing me and guiding me over to the bed.
Laying me down on top of the thick stack of diapers, she squeezed some Desitin in the palm of her hand and after raising me by my ankles, began smearing it across my bottom.
“The last time I saw these cute little buns, they were sporting a nice, deep shade of red,” she smirked as she set my legs down.
I blushed and sucked harder on the pacifier, the entire experience bringing back waves of humiliation from my bedtime routines with my mom.
Denise sprinkled my entire area with baby powder and even up on my chest, softly rubbing it in as she looked down on me and winking playfully. The fragrant scent brought back memories of weakness and inferiority in me, making me recall my childish lack of control.
Drawing up the bulky, but very soft cloth, she slipped a pair of safety pins through to secure it around my hips, first one side, and then the other.
“There!” she said with a flourish as she patted the fat front of my padded crotch, “All set and ready for your baby panties!”
I cringed with embarrassment as she took the pink pair of waterproof pants next to me and positioned them over my feet, drawing them up my legs in a tortuously slow fashion, no doubt intended to draw out the humiliating procedure as long as possible.
“How does it feel to be wearing baby pampers again, sissy?” she asked me.
My face glowed red with embarrassment and I looked away.
Using her perfectly manicured fingers, she slowly ran them around the elastic waistband, pulling them up and over the thick cloth surrounding me until the fluffy diapers were fully contained inside the plastic pants. With another dusting of baby powder between my legs, she put the diapering supplies away and came over to put my top on.
“I don’t have much for you to wear just yet, but don’t worry, sugarplum, I’ll get you all fixed up in no time,” she assured me.
The top she was putting on me was made of pink fleece, with short white puffy sleeves and a teddy bear playing with blocks decorating the chest. The hem, which was so short it barely went down to my navel, ended in a soft row of white ruffles.
I felt extremely babyish and I couldn’t put my legs together due to the thickness of the diapers between my thighs. Looking up at Denise’s pretty smiling face brought on sensations of helplessness in me. And I felt that whatever control I might have had in this relationship was rapidly disappearing.
Climbing onto the bed, she slowly unzipped her bustier, tantalizing me as she allowed her tremendous breasts to gradually be revealed in her sexy push-up bra. With a seductive look, she crawled over and straddled me, her magnificent bosom only inches from my face. Looking up into her stunning eyes, I felt powerless before her.
Taking out the pacifier from my mouth, she put it aside and positioned her cleavage right in front of my nose.
“Does baby want to nurse from Mommy’s boobs?” she asked in a musical voice.
“Uh-huh,” I said weakly. My penis had expanded in it’s tube and was pushing against the end as hard as it could. If only she would let it out!
“Um…D-Denise?” I ventured carefully.
“Shushhh, baby,” she said as she put a finger to her lips. She undid the clasp at the front of her bra and her gigantic melons fell free like two watermelons falling out of a basket. Reaching on either side of me, she held my arms down, pinning me in place. Before I could say another word, she mashed her big left breast into my face, forcing her enormous pink nipple into my eager mouth. I wasted no time in sucking it, and it quickly became hard in my mouth.
“Thaaaat’s Mommy’s baby,” she cooed.
Reaching back, she began softly stroking the smooth front of my diapers, which only aggravated my arousal level, making my little imprisoned penis throb with frustration and impotence. It was maddening, not being able to do something as simple as have a normal erection!
After about ten minutes, she switched over to her other breast and the sexual torment continued. I had never been so turned on in my entire life!
Once again, I tried to reach up and cup her free breast but she slapped my hand away.
“Sorry sissy, that’s not for you,” she told me.
I mewled in frustration but continued to enjoy the engorged nipple in my mouth.
After another five minutes or so, she pulled away from me without warning, bringing my breastfeeding session to an abrupt end.
“Okay, that’s enough of that for today–now baby needs his ba-ba before beddie-bye,” she said.
I furrowed my brow with disappointment–I didn’t want to be treated like a baby anymore, I wanted to be treated like an adult and her peer.
Reaching behind her, she picked up a baby bottle with a pink top that was on her night stand and brought it over to me.
“Open up, baby,” she said with that heart stopping smile.
I whimpered and shook my head no.
“Come on–open up, baby,” she repeated, pushing the dripping rubber nipple to my lips.
When I refused to open my mouth, she slapped my bare thigh which elicited a yelp from me. As my mouth opened, I was rewarded with a fat nipple and the big bottle of warm milk.
I had always detested milk, especially warm, since I considered it to be a drink only for infants. I whined and shook my hand but Denise kept the bottle to my mouth and forced me to continue to drink from it.
“There, there,” she said, whispering down at me, “that’s a good baby, drink your milk like a good little boy.”
It was so humiliating having to nurse from the bottle and listen to her treat me like a toddler but I had to admit it was also wonderful to be in such close proximity to such a pretty woman, and to have her fawn over me. I decided if the price of that was playing her little game, for now, then so be it. I drank the milk which seemed to make her happy, although for my part, I started to feel myself getting unexpectedly drowsy.
“Tell you what, Chrissey,” she said as she beamed down at me, “If you can manage to keep your diapers dry tonight, maybe I’ll consider letting you graduate to some training panties, okay?”
I nodded my head in acknowledgement. I wasn’t used to drinking anything before bedtime but it wasn’t too late yet and I could always use the bathroom before I went to sleep.
The last thing I remembered as the lights faded around me was looking up over the top of the baby bottle at Denise’s smug, smiling features.
When I woke up, I felt somewhat disorientated and it took me a moment to get my bearings. Looking around the dimly lit room, I realized I was in Denise’s bed and I was still wearing the thick diaper she had put me in last night.
And it was at that moment, that I suddenly realized I had thoroughly soaked it during the night!
Oh my god–what was she going to think of me now?
Of all nights to have an accident, why did it have to be the one night I spent with the hottest woman in town?
I was only too familiar with the feeling of cool, clammy Birdseye cloth clinging to my hips and bottom. I had felt it every morning during my early teen years as a result of my mom putting me in diapers and plastic pants every night. Her solution, while it kept my bed dry, ensured I felt the soggy effects of my incontinence until she decided to change me.
Somehow, I had to get rid of them before Denise discovered me.
Slowly rolling over to see if she was awake, I came to find her right next to me in bed, naked and lying on her side, her head propped on her hand as she lay there, smiling over at me.
“Did my baby sleep well?” she asked with a beautiful smile.
I blushed and swallowed hard.
“Um…yes, yes I did,” I replied uncertainly.
I glanced around the room, trying to think of some way to get out of bed to remove the diaper before she discovered it was wet.
“And was my little sugarplum able to keep her diapers dry?”
I bit my lip as my face turned a bright red.
“Um…ah, I um…” I stuttered.
Reaching down beneath the blankets, I felt Denise’s smooth hand slip inside my diaper, revealing my wetness to her all too clearly.
“Looks like Mommy has a little bedwetter on her hands,” she said with a knowing smile.
“I-it-it was j-just an accident,” I stammered, afraid she would kick me out and never speak to me again.
“I don’t think so, Chrissey. And I don’t think Mommy’s little baby can be trusted today without her diapers,” she told me.
I shook my head, my apprehension rising as to where this was going.
“Oh no–it was just an accident–I don’t know why it happened–it was just a fluke,” I tried to explain.
“Now Chrissey, you and I both know it was no accident. How do I know you won’t wet your pants today at work?”
I didn’t like where this was going at all.
“Mm-hm, I think my little baby’s going to have to wear some diapers to work today,” she told me with a disarming smile.
I shook my head and put my hands up.
“Now wait…I mean, I can’t–I mean, I’m not wearing–”
“–On the other hand…I can think of one way in which you could get out of it…”
She was smiling coyly at me and with those devastating blue eyes, it was all I could do to resist her charm.
“I’ll tell you what…all this talk of putting you in diapers is getting me hot…if you can make me cum in five minutes, I’ll let you go to work without your diapers.”
Before I could respond one way or another, Denise was already rising up and she pushed me onto my back, quickly straddled my torso.
“No–wait!” I squealed.
She inched her way up my chest, her big, hard cock quickly closing to within inches of my face.
“My phone says it’s 7:05–you have until 10 past the hour Chrissey–better get to it,” she smirked at me.
“No…please,” I pleaded, “I don’t like sucking cock–”
My words were interrupted as she shoved her meaty leviathan into my mouth. She was straddling me, supported by her knees as she steadied herself with her arms against the headboard of the bed. In this position, with my head backed against the pillow, I could do nothing as she face-fucked me, shoving her fat cock deep into my mouth and grinding her pelvis against my face.
“Use that tongue again, Chrissey…oh…that’s it…yes, that’s better…suck it good…ohhh…that’s my little sissy…thaaaat’s Mommy’s little boy…suck that sweet cock…mmm…yes…”
Her big balls were slapping my chin as the fat end of her cock pounded urgently against the back of my throat.
“Ohhhh…what a good little cocksucker you are, Chrissey,” she moaned.
Knowing I had an impending deadline, I tried my best to please her, despite my feelings to the contrary. I swirled my tongue along the warm, throbbing underside of her massive head, sucking and slurping as best I could.
But there was only so much I could do. The pillow kept my head from moving and Denise was the one controlling her thrusts into my slobbering mouth.
“Get ready, Chrissey…breakfast is coming,” she said breathlessly.
I hoped it was inside the five minute deadline but it seemed like she had been pounding my face for 8 or 9 minutes already.
Her cock swelled in my mouth, and she jammed it deep into my throat.
“OHHHHHHHHH GODDD!” she cried, as she loudly and forcefully emptied her balls.
I could feel warm globs of thick, sticky semen being blasted down my throat and I swallowed again and again. Finally, she pulled her cock out long enough to fill my mouth with one last good load before pulling it out entirely.
A white strand of cum followed the blunt tip of her cock from my mouth and I gasped for air.
“Oh, that felt so good,” she said as she held her still hard cock in her hand, moving it left and right and smearing the last bit of cum across my lips.
“Lick that up, Chrissey, it’s what all sissies love,” she said condescendingly.
Reluctantly, I did what I was told, hoping I could get my wet diaper off and get ready for work. I reached over and picked up her phone, but to my dismay, the face read 7:15 on it.
“That’s right baby…looks like someone is going to work in diapers and plastic panties today,” she said with a big smile.
“Noooo,” I moaned unhappily.
“Don’t worry sugarplum, I won’t make it as big as the one you’re wearing now,” she assured me.
“But–how am I going to hide it?” I whined miserably.
“Don’t worry, honey-bunch,” she said dismissively, “no one will see a thing, you can wear your jacket which will cover that cute bottom of yours.”
Reaching down, I felt the hard object inside my diapers that was my chastity device.
“Denise, when are you going to unlock my penis?” I asked her, “I haven’t been able to cum for a week now.”
“If I’m going to be changing your wet diapers, you better start calling me Mommy,” she corrected me.
“Okay, M-Mommy,” I said awkwardly, “When are you going to unlock my chastity device?”
“Tonight, if all goes well,” she assured me as she got of bed, “I promise I will unlock you.”
My spirits rose immediately. Finally, I would get some relief for my poor, aching balls! As Denise laid out a changing pad, I was already thinking of ways in which to cum. My imagination, deprived of an orgasm for so long, began working in overdrive, thinking of all the delicious ways I could cum…would she be returning the favor of oral sex for me? Maybe she would let me rub my penis between her big, beautiful boobs? Hell, even a handjob would be wonderful from this sexy babe.
Denise busied herself getting the diapering supplies out and arranging them on the bed; she put a fresh diaper, baby powder, wipes, and diaper rash creme next to me. I didn’t see any plastic pants so I assumed the diapers today would be more symbolic, than for real purposes.
She pulled my wet ones off and placed them in a plastic bag, using the baby wipes to clean me up.
“Wow, I’ve never seen so little hair on a boy before,” she said as she wiped my pubic area, “Are you sure you’ve been through puberty yet?”
I blushed and assured her vehemently that I had.
“Well, this looks suits you better anyway,” she replied as she took a palm full of diaper rash creme and smeared it across my bottom cheeks. A thorough dusting of powder followed and I grew apprehensive again.
“Not so much!” I complained, “Some one will smell it on me.”
“Oh no, they won’t,” she disagreed, “Besides, you’ll be more comfortable this way.”
In no time at all, she deftly pinned the new diaper on me which was thankfully, much thinner than last night’s, although I still had concerns that I would be able to conceal it.
Turning around briefly, I thought she was done until she revealed a pair of pink nursery print plastic pants in her hands.
“D-do I have to wear those too?” I asked crestfallen.
“Of course, baby–what if you wet yourself today?”
“I won’t do that–I promise–please don’t make me wear the pants too,” I protested.
“Sorry sissy,” she said ignoring me and feeding my feet through the leg holes, “We can’t take that chance.”
I felt like I was with my mom all over again, who did as she pleased, regardless of my objections. I shook my fists and whimpered with frustration.
Worse yet–these waterproof pants were made of a somewhat stiffer plastic and they crinkled loudly as she drew them up my legs.
“I still don’t see why I have to wear diapers during the day,” I complained bitterly.
“Because I can’t trust you to keep your pants dry, sissy. Now if I hear one more word out of you, I’ll put you over my knee and warm your little bottom with my paddle.”
I pouted but remained silent as she positioned the humiliating pink panties over my diaper.
“Okay, stand up, Chrissey,” she instructed me.
I stood up next to her and she physically turned me around, fiddling around with something at the back of the waistband of the plastic pants.
“What are you doing?” I asked suspiciously.
I felt the waistband getting cinched snug and a lock clicking shut.
“Just making sure you don’t get any ideas about removing these during the day,” she said with a smug tone in her voice.
She emphasized her statement with a smack to my diapered bottom.
I gasped and craned my neck around to look. I hadn’t realized it before, but the waistband contained a small chain and Denise had just locked it closed, permanently securing the plastic pants, and therefore the diapers around me until she chose to remove them.
I balled my fists and stamped my feet in frustration.
I wanted to protest loudly and demand she take them off immediately but the memories of being over her lap were still fresh on my mind. She had already proven that she was physically stronger than me and I didn’t need a repeat demonstration of that fact over her lap.
Instead, I gritted my teeth, rationalizing that these were acceptable sacrifices to be made for having a relationship with such a drop-dead gorgeous woman as Denise.
I didn’t like it, but compared to what my love life had been a week ago, this was a thousand times better.
And tonight, I was going to get to cum with her. How many other guys would have willingly paid to be in my shoes?
That morning at the bank, I was nervous as hell.
I had done everything I could do to conceal my diapers by keeping my jacket on but the plastic pants were infuriatingly loud. Every step I took threatened to reveal my shameful secret to everyone at work. I had to walk slowly and cough to try and cover the sound of the crinkling. Even still, some of the people were giving me strange looks and I saw some of the female clerks whispering amongst each other. Were they talking about me? I couldn’t be sure.
It didn’t help things that I smelled like baby powder. It was a distinct smell that would be hard to explain away, should someone ask me.
It also frustrated me that Denise seemed to be distant with me again; acting cool and treating me in a perfunctory fashion. She wouldn’t return my smiles at her and what little conversation we had, was strictly professional.
I sent her several text messages but she didn’t reply to any of them.
About midmorning, I signed for a small package from FedEx which was addressed to her. She seemed very pleased to get it but then when I tried to stick around, she dismissed me curtly.
It hurt my feelings that she could be so warm and intimate with me at her house but cold and indifferent during the time we spent at work together. I mean–I didn’t expect her to exactly throw her arms around me when I walked into the room, but why was she treating me like a total stranger?
In addition, even though I had done everything I could to limit my liquid intake today, I was still fighting a strong urge to pee all morning. I was crossing my legs and fidgeting, practically dancing at my station as I dealt with bank customers.
Lunch was coming up and I had been told that the management was taking everyone out, on account of the new merger. I was determined to ask Denise to unlock my plastic pants at that point and relieve some of the built up pressure.
I was only an hour away from lunchtime when it all became too much to bear. All the dancing in place wasn’t going to make my urge go away and I reasoned if I just let a little out, I could hold the rest back.
And maybe Denise wouldn’t even detect such a small amount of dampness anyway?
Finally there was a break in the line to the tellers and I relaxed ever so slightly. I felt a stronger than expected surge suddenly empty into my diapers and I tried to cut off the flow. I stifled a sob as I realized the futility of holding back the dam. My little penis flexed weakly inside my chastity device and more and more hot pee flooded my diapers as wave after wave saturated the soft cotton cloth surrounding me. In no time at all–I felt like I was swimming in pee!
My mouth was hanging open and I looked over to see Ashley, my co-worker staring at me.
“Are you okay?” she asked pointedly.
I blushed furiously and looked down at my checks.
“Y-yes, I’m–I mean, uh, I was just daydreaming,” I stammered foolishly.
Ashley’s eyebrows went up as if to say ‘whatever‘ and she shook her head.
Did she realize I had just soaked my diapers?
My face wouldn’t stop burning as I felt the pee seeping between my legs, absorbing into the seat. I felt so babyish! I tried to stand with my feet apart but I could feel the warm wetness already upon my buns. For the moment, it appeared that I was the only one that was aware of my catastrophe, but I couldn’t stop blushing–I was so humiliated!
For the next half hour, it was impossible to concentrate on my work, and I kept making mistakes with customers.
I heard my name being called from across the room behind me and I froze in position. Turning my head around carefully, I saw Denise standing at her doorway, a serious look on her pretty face. She was wearing a silky white blouse that clung deliciously to her big breasts, a short, snug grey skirt and her stiletto heels.
She looked like a goddess of justice, about to pass sentence on a weak mortal.
“Come to my office,” she ordered me in a demanding voice.
Out of the corner of my eye, I saw Ashley smirk as I walked slowly away and into my supervisor’s office.
Moving past Denise, I was filled with trepidation, and she closed the door behind me.
I saw my underwear laying on the top of her desk and she looked down on me, her hands on her curvy hips.
“Did Mommy’s little baby wet his diapers, or is he ready for his big boy underwear again?”
I felt so weak and inferior before her, unable to look up into her eyes. It was like I was five years old, all over again, being scolded by my mommy.
I shuffled my feet and stared at the floor, knowing she would discover my soggy diapers, all too soon.
Without waiting, she reached down the front of my pants, slid her slim fingers inside my diapers and a smile crossed her face.
“Well…looks like someone isn’t quite ready to graduate to his big boy underpants, is he?”
I blushed hotly and stared at the ground.
“What do you say, Chrissey?” she pushed me.
“I-I couldn’t hold it anymore,” I whined.
“Mm-hm,” she nodded, “Just as I thought. Well, sissy boy–looks like you’ll just be wearing your wet diapers the rest of the day.”
“C-can’t I get a fresh change, please?” I whined pathetically.
“Nope, I didn’t bring a diaper bag with me–I didn’t realize what a big baby you were,” she countered emphatically.
With that, she spun me around and slapped my diapered bottom hard, essentially dismissing me. I walked out, thoroughly ashamed and returned to my counter, my plastic pants crinkling audibly.
Everyone was closing their drawers for lunch and I put my stuff away and locked up.
We all met at a restaurant across the street and the employees sat among three tables. I had never felt like I was a part of their crowd but on this occasion, the guys made room for me at their table.
I sat down with a humiliating squish and I prayed no one would detect the smell of pee coming from my general vicinity. It was hard to concentrate, with the saturated cloth clinging to my bottom and hugging my tiny, caged genitals. I prayed it wouldn’t leak out past my plastic pants and reveal my secret to everyone around me when I stood up.
The guys were having an animated discussion amongst themselves until Denise entered the restaurant. As always, she was the center of attention whenever she entered a room. And as always, she ignored them as she sauntered over to the table where the women were seated. All eyes followed her, admiring her sexy, voluptuous body in her short pencil skirt and revealing white blouse.
Her table was close enough that I could hear snatches of conversation between her and her friends but not much else.
A few moments later, Jordan showed up, and Denise’s face lit up in a display of obvious joy.
Jordan was a girl that had been working at the bank since before I started there. She was in her mid-twenties, slim, with long straight blonde hair. With her toned physique, beautiful face, and what many of the guys said were fake boobs, she attracted almost as much attention as Denise. The difference was she wasn’t as stand off-ish as the latter and therefore, didn’t have a reputation as an “ice queen”.
Nevertheless, like all hot women, she barely knew I existed.
Jordan was perhaps the only true friend that Denise had at the bank, probably because from a social status perspective, they were two of a type, and the fact is, beautiful women tend to congregate with each other. I had known that simple fact since my high school years.
But the look on Denise’s face made me start to wonder if there was more to their relationship than they let on.
She stood up from her seat to hug Jordan, and I couldn’t help but suspect there was more affection being shown than one would think for just two friends greeting each other. I felt a strong pang of jealousy ripple through me that someone else had Denise’s attention and it gnawed at me all through lunch. They were chatting busily between each other and occasionally, I would see Denise’s hand linger on Jordan’s toned thigh.
Was there something going on between them? Was Denise attracted to Jordan sexually?
I couldn’t stand the thought that I wasn’t the only sexual interest in her life.
Lunch finally ended and we were the last group to get back to the bank. When I walked up to my counter, I saw our manager, Mr. Jenkins, at my station and he was facing my computer screen, although because he was blocking my view, I couldn’t see what it was he was looking at.
And as I got closer, I could see a very angry look on his face. Ashley was trying to act busy, but clearly, she wanted to see what was about to happen.
He saw me out of the corner of his eye and he turned to face me.
“Mr. Jones? Do you have an explanation for this?” he snarled at me.
Looking at the computer screen, I saw a web page for something called SpankedSissies.com and I froze in place.
I blushed a deep shade of red and began stammering nervously. A trickle of pee escaped into my already very wet diapers.
I stood before Mr Jenkins, shocked and humiliated with his unexpected discovery. I had no idea how the website had been put on my screen or who was responsible.
“N-no, Sir, I don’t know who put that there.”
“This is–your station–is it not?” he demanded as his white eyebrows furrowed into a menacing V.
“Y-yes sir, b-but I’m just coming back from lunch–I don’t know who put that on my screen,” I tried to explain.
“I’ve been running this establishment for over thirty years…” he lectured me, “and our computers are not for the purposes of viewing porn–Do I make myself clear??”
“Y-yes, Sir,” I quaked.
“This will serve as a verbal warning to you, young man. If it happens again, it will be a write-up in your employee record,” he told me sternly, “Maybe you think the rules don’t apply to you around here but let me assure you that they do.”
I was so scared, I felt another warm stream of pee suddenly flow into my already soggy diapers. My face, burning red with shame, blushed even deeper.
I really needed this job. It was my first one out of high school and I could barely make ends meet as it was. One more late payment on my apartment and I would be out in the streets.
“Y-yes, Sir,” I repeated.
Ashley was staring at me and it was obvious she felt no sympathy for me at all.
Mr. Jenkins stormed off, muttering something about ‘sissies’ under his breath and I quickly changed the screen back to the default browser.
Glancing back at Ashley, I saw her shaking her head in disapproval before returning to her work.
I was at a loss to explain how the embarrassing webpage had been pulled up on my screen–obviously someone had to have put it on there as a prank.
But I was SO humiliated! It was bad enough to be treated like a sissy by Denise, but to advertise it like this was mortifying. I knew Ashley would be telling all her friends at her first opportunity. Now, everyone at the bank would be thinking I harbored secret, perverse fantasies of being a sissy and getting spanked. Nothing could have been farther from the truth!
The rest of the day was awkward, uncomfortable, and humiliating for me.
Finally, as I was walking out to my car, I got a text message from Denise. It said;
If you want to get changed out of your wet pampers, come over to my place.
That was first and foremost on my mind so I headed straight over.
After my degrading meeting with her in her office, I was afraid she would take back her promise to unlock my poor caged penis, but on the other hand, maybe she would have mercy on me after all that had happened to me today.
When I arrived, Denise ushered me in, smiling at me warmly. She was wearing a tight fitted top, and as low cut as it was, she had still unbuttoned the top two buttons. My eyes just about popped out of their sockets as I gazed lustfully at her sexy, yawning cleavage.
She guided me to her room and began undressing me, removing all my clothes except for the sodden diapers. Positioning me on the changing pad, she pulled down my clinging plastic pants and unpinned the soaking wet cloth.
“My my,” she commented, “My little baby really wet herself today, didn’t she?”
I nodded my head, even as I blushed at her remark.
“Don’t you worry, baby, I’ve got some new, thicker diapers that came in the mail today. They have nice, thick soaker pads down the center for heavy wetters like you.”
I wanted to argue with her contention but I didn’t want to do anything that was going to cause her to change her mind about my chastity. I had to get it removed today.
After she put the wet diapers aside, she produced a razor and some shaving cream.
“You hardly have any pubic hair as it is, but I want my baby to be girly smooth down there,” she said as she removed the few strands of light hair around my package.
When that was completed, she took the necklace from around her neck and unlocked the chastity device.
Never had I been so happy to see my penis again! After removing all the pieces of the chastity device, my little stub was finally free.
I immediately reached down to rub it but Denise slapped my hand away.
“No sissy boy, I’ll take care of that for you,” she assured me.
Putting some baby oil on her hands, she reached down and began gently massaging my tiny member.
I sighed and relaxed, or as much as one can relax when gazing at a woman as pretty as Denise, with the most spectacular boobs on the planet.
As I began breathing deeply, she paused long enough to retrieve the pacifier and she pushed it between my lips.
“There you are baby, you should have something filling your mouth at all times.”
I didn’t mind at all. I was willing to play baby games with her as long as I got to cum, and this one promised to be an earth shattering climax.
As she continued to fondle my diminutive penis, she began a childish banter with me in her sultry, sexy voice.
“Does mommy’s little baby like this? Hmm? Does my little sugarplum want mommy to keep rubbing her tiny baby pee-pee?”
I blushed even as I moaned and looked into her eyes, my lust and desire making my breathing labored.
“Mommy’s got a little present for her baby tonight…would you like to see it?” she asked me playfully.
I nodded my head deliriously, curious as to what she might have gotten me.
Taking my head in her hand, she guided it down and pushed my nose deep into her cleavage, momentarily blocking my view. I felt her slipping something around my scrotum, and pulling my balls and penis through.
Suddenly very concerned, I pulled my head back and looked down. A singular, solid pink plastic ring was behind my balls and Denise was holding the other half of a new pink chastity device in her hand.
“This one is a little different from the one you had on before,” she said as she held it up for my inspection, “See the spikes on the inside of the tube? Those will ensure my little baby stays nice and soft, all of the time.”
My mouth fell open and the pacifier dropped onto the bed.
“I-I’m n-not wearing that,” I gasped in horror.
“Oh yes you are, Chrissey–this is your new chastity device and your new best friend.
“You see, erections are for real men, and these spikes will make sure a sissy like you can never have one.”
“B-but, you-you said you were going to unlock me today!” I croaked.
“And I did,” she smiled at me, “And now you’re going to be locked back up.”
“No! I’ve had enough of this!” I shouted angrily, “I’ve gone along with your weird games but this is going too far.”
Denise dropped the chastity tube and quickly grasped my ankles together, abruptly swinging them upwards over my head and forcing me to put my hands out to steady myself. With her free hand, she snatched up the paddle and brought it down hard on my exposed bottom.
I howled in pain and tried to wrest my legs free but she held me too strongly.
I cried out at the top of my lungs as she continued to swat my damp, bare cheeks mercilessly.
Her paddle scalded me with blistering slaps and I immediately burst into tears.
Each fiery swat from her paddle made her tremendous breasts shake and jiggle within her top. Any other time, I would have found the display highly erotic but right now, all I could think about was the stinging bite of the wooden instrument of punishment in her hand.
My vision became blurred as the tears filled my eyes and streamed down my face. I bunched my fists and shook them as I bawled like a baby. At this moment, I hated Denise completely. I hated her for her strength, her unflinching, domineering resolve, her smug, condescending treatment, and lastly, for her incredible beauty.
I wailed like a helpless toddler as she harshly paddled me with abandon.
Occasionally, Denise would pull my legs even higher so she could swat my seat more effectively. I couldn’t believe how strong she was! Just when I thought she was done, she would devote her attention to the sides of my cheeks, giving them slap after biting, vengeful slap.
When she was finally finished and she let my legs down, I was gasping for breath and crying hard. I couldn’t see the expression on her face clearly through the tears filling my eyes.
“Now–Is Mommy’s little baby ready for her chastity device?” she asked me sternly.
I nodded my head vigorously as I tried to wipe my wet face with my arm.
Denise dabbed a little baby oil on my shriveled penis, rubbing it softly until she produced a little rise and then she popped it into the short pink tube. Pushing it up against the base ring, she inserted a long key and locked it shut.
“There, that’s much better,” she said satisfied, “And now, it’s time I put my baby into her new bedwetter diapers.”
The next couple of weeks began to develop into a pattern of sorts.
I was spending the night more and more over at Denise’s house and she was making sure I was diapered for bed on a regular basis. I didn’t always spend weekend days with her but when I did, she was dressing me up in ever more humiliating ways, which would always include as part of my outfit, thick, babyish diapers and plastic pants. I don’t know where she found them, but the tops she would put me in were short and frilly, often in pastel colors with ruffled or lacy puff sleeves. They usually had infantile designs on them which made me look even more like an incontinent toddler.
I didn’t like it, any more than I liked having to suck her big, thick cock every morning and evening. It was a humiliating, degrading job, made more so, by her continuous litany of condescending comments and taunts. And it wasn’t made any easier by the fact I could barely stuff it into my mouth or the struggles to swallow her copious loads of warm, creamy semen, but she gave me no choice in the matter.
I had never had a lot of willpower, and it seemed this relationship was only emphasizing that fact. I sometimes mused that she had picked me for precisely that reason, but to be honest, I didn’t want to dwell on it too much. The important thing was, the guys at my bank thought I was cool because I was dating the most amazing woman in town, so that was reason enough to put up with Denise’s peculiar and eccentric preferences. I had never once been the object of anyone’s envy, so this was an entirely new sensation for me.
The only problem was, I hadn’t cum in two weeks and I was frantic for some kind of satisfaction. This was made worse by the fact that Denise made a point of dressing provocatively at home which had a predictable effect on my poor, caged little penis. One word from her, a button undone, or a soft caress from her hand caused my long deprived penis to grow in it’s short tube until the soft, tender head pushed into the hard, unyielding spikes inside the device. No amount of fidgeting or wrestling with my chastised package would alleviate the agony. The spikes were as cruel as they were unforgiving and I couldn’t make the pain go away unless I concentrated on mundane things like bills or taxes. But that technique only worked until the next time Denise bent down in front of me, and then the vicious cycle began all over again.
I think she took an evil delight in tempting me with her sexuality, just to watch me cringe and writhe from the sharp bite of the spikes. When I asked her when she was going to release me, she always answered in vague terms like, “soon”, or “you’ll just have to be patient”.
But the enforced chastity had the effect of making me so horny I was willing to do anything she asked, and no indignity was too much to bear in hopes of getting released from my penis prison.
So far, I had only been put over her lap for a spanking on one occasion since the dreaded paddling the night she introduced me to the new chastity device. Still, those experiences were enough to make me never question her absolute authority over me, and I was extremely hesitant to push her any more than I dared on a topic of disagreement.
There was one weekend that will stand out in my memory for it’s singular level of humiliation at her hands.
The morning had started out normally (for a visit to Denise’s house anyway), with her changing me out of my wet nighttime diapers and into an outfit she had chosen for me for the day.
In this case, it was a short white fleece top with a teddy bear design on the chest and short, puffy sleeves decorated in a pink nursery print. The hem, also very short, was lined with soft pink ruffles and barely extended past my navel. I wore pink ruffled anklets which matched the ruffles around the leg and waist bands of the white nursery print plastic panties covering my fat, bulging diapers.
She had put me on the floor of her living room with a Disney Princess coloring book and given me instructions to fill out several pages using some crayons. I guess I must have gotten distracted because I never heard the vehicle pulling up in her front driveway.
Before I knew it, Denise had walked over to the front door and opened it, allowing two workmen to stroll right into the house without any sort of warning. Looking up from my drawing, I gasped with shock as they walked in and stared down on me, the amusement plain on their gruff, unshaven faces.
Denise was all smiles as she came over, acting as sultry and charming as only she could, saying, “Can I get you boys something to drink?”
“Yeah, a beer would be great,” the bigger of the two grunted as he stared down on me in disdain and disbelief.
I blushed a hot shade of red, as I looked into their smirking faces, only barely managing to stem the flow of panic-induced pee into my thick, embarrassing diapers. It was obvious that they had been forewarned of my appearance and equally obvious that Denise had planned this encounter specifically to humiliate me.
“Oh, don’t mind Chrissey here, he just has a hard time keeping his pants dry so I had to put him back into diapers.”
The burning in my cheeks spread down to my neck and chest and I gulped in abject shame. She made it sound like I had no more control than a little boy still being potty-trained!
Denise sauntered out of the room, while both men’s eyes followed her every move, greedily drinking in her sexy curves. Today, she had chosen a short, bouncy skirt that barely covered her trim derrière and her strappy high heels lent her a sexy, impossible-to-ignore gait.
Once around the corner, the men returned to looking down at me and I squirmed with anxiety and embarrassment. I felt like such a total sissy, my big, thick diapers, plain to see with their shiny plastic pants and babyish print.
“Dude, I didn’t see a ring on her hand,” the big one told his friend, “I think I’m gonna make a move on her before we go.”
I felt successive waves of humiliation, resentment, and jealously wash over me as it became obvious that they didn’t consider me in the least, a contender or competition for their lustful ambitions with Denise. They hadn’t even bothered to ask–one look at my sissy baby outfit and they assumed a woman like her would have nothing to do with a prissy boy like me.
And yet, I was afraid to open my mouth and dispel their conclusion. They would only laugh and ridicule me with greater contempt.
Denise returned shortly with two cold beers and she handed them over with a ravishing smile on her pretty face.
“Let me know if there’s anything else I can get you boys,” she said in her most flirtatious voice.
The big one stood up a little straighter and grinned back at her lecherously.
“Well, since you asked…here is my card–that number at the bottom is my personal cell phone. You feel free to call me anytime–anytime at all, you need a man’s help in this house.”
I knew the tone of his comment was a direct reference to my lack of the same and I bunched my fists in anger.
Denise giggled and led them back to the end of the hallway and into a spare room while I was left to pout on the floor in frustration.
To add insult to the situation, it was only then that I realized my diapers were wet–it had happened without me even realizing it!
I blushed anew at my childish lack of control, but I blamed Denise for being the ultimate architect of my humiliation. This would never have happened if I had hadn’t come over to her house in the first place.
When Denise came back into the living room, I angrily threw the coloring book at the wall and began shouting at her, accusing her of arranging this whole situation to deliberately humiliate me.
My tantrum brought about what was becoming a predictable response.
Inside of a minute, I found myself bent over her lap, diapers unpinned and pushed back, my plastic panties tangled around my ankles, as she soundly paddled me within easy earshot of the workers.
Through the tears filling my eyes, I could see their blurry forms as they came out to watch the weak, diapered sissy getting his soft, bare bottom spanked hard by the oh-so-hot woman that had employed them.
The line of bank customers finally began to grow shorter and I glanced up at the clock on the far wall, only to see I still had three hours left to go.
I sighed heavily and looked down at the pile of work next to my computer.
I was bored as hell and wanted to go home, not take checks and dispense cash to people who didn’t care if I lived or died.
Across the main room, I could see Denise talking with Mr. Jenkins, our manager. One couldn’t help but notice that her blouse was super snug as always, and I could clearly make out the outlines of her sexy white push-up bra underneath.
I sighed with admiration.
Just last night, she had allowed me to nurse from her big nipples for a half hour before bed. She had even mashed my face between her massive breasts, practically suffocating me in her glorious, feminine embrace.
My pleasant memory was interrupted by the biting sensation in my groin as my little penis grew with arousal and began pressing urgently against the sharp spikes in the tube of my chastity device.
I winced painfully and shifted in place, trying in vain to alleviate the torture to my tender head.
I had to stop looking at her–everything about her screamed sex and that was the one thing I couldn’t think about.
Ashley came over to drop off some checks and she looked at me strangely.
“Why does it always smell like baby powder over here?” she said accusingly.
“I dunno,” I replied lamely as I blushed with shame.
I had pleaded with Denise to use less of the fragrant smelling powder when she chose to diaper me in the mornings but she always ignored me or worse, put even more on. I always smelled like a baby’s nursery when I arrived at work and people were starting to get suspicious. I had bought some larger pants to wear but even those barely concealed the fact that I was wearing diapers and plastic pants underneath.
“Here,” she said thrusting a stack of checks at me, “Sort these and Heather’s before you go today.”
“Why can’t she sort her own checks?” I complained.
“Because I’m giving you that job,” she quipped.
Ever since Ashley had been promoted to lead teller last week, she had been lording her authority over me at every opportunity.
I bit back the remark on my lips and accepted the additional workload in sullen silence. I also resented that it seemed that the women here were getting all the lucky breaks and being given positions that I should have been considered for. It wasn’t fair, and I hated being ordered around all the time.
An hour later, I had to take some cash to the vault and I locked up my drawer before stepping away. I was required by our rules to notify Ashley but my ego prevented me from doing so and instead, I just walked away without saying anything.
Anyway, it was only for a few minutes and I figured the other tellers could handle the few people we had in line.
I went to the vault and sorted the cash, placing the notes in their appropriate sections.
Taking a moment to reach down into my diapers, I reflected that they weren’t too wet and I knew from past experience I wouldn’t have any difficulty getting through the last couple of hours of work.
My feelings of good nature were rudely shattered as I came back to see Ashley and Denise standing at my station, engaged in what sounded like a very serious discussion.
“Wha-what’s going on?” I asked nervously.
“Didn’t Mr. Jenkins tell you you weren’t allowed to look at porn on these computers?” Ashley said bluntly.
I gasped as I looked down at the screen between them. Splashed across the face of the monitor was a picture of a feminine looking guy bent over and being forcibly humped from behind by some dominant, leather clad woman. The website’s name was in big pink letters across the top which read PunishedSissies.com.
I blushed red and my mouth went dry.
“What do you have to say for yourself, Mr. Jones?” Denise said, her tone both accusing and overly formal with me.
“I-I didn’t put that there!” I cried, “Somebody else must have put it on my screen.”
The other tellers were starting to look at us and I felt a bead of sweat trickle down my temple.
“No one’s been at your station since you left it,” Ashley said pointedly, “which, by the way–you failed to inform me.
“This isn’t the first time, Denise.”
I felt the blood rushing to my head from indignant frustration.
“Is that true?” Denise asked.
While I knew I had nothing to do with the website on my computer, she did have me on the rule of notifying Ashley prior to leaving my station.
“Um…yes,” I muttered.
“I think we are going to need to finish this discussion in my office,” Denise said gravely.
My heart sank as the two of them turned and led the way, leaving me to face the stares of the rest of the staff who appeared anything but sympathetic.
It was customary during disciplinary situations to have a witness present, for reasons of liability. That way, the employee couldn’t claim later that something was or wasn’t said.
When we got to her office, Ashley closed the door behind me, her expression dead serious. Despite my innocence, I felt a shiver of fear go down my spine. This was all I needed.
Predictably, a stream of hot pee surged into my damp diapers before I could stop it.
“Have a seat,” Denise told me curtly, indicating with her pen, a chair in front.
I slumped into the chair as the other two took their places across the desk from me.
“Viewing porn on company computers is a serious breach of the rules,” Denise began dryly, “And you were warned about it by Mr. Jenkins himself, just two weeks ago.”
“–But that wasn’t me either!” I protested bitterly.
“Don’t make this worse for you than it already is,” she replied.
I couldn’t believe the woman who had let me nurse from her boobs only 14 hours previous was lecturing me and putting my job in jeopardy.
“Who else could have put it there?” Ashley countered, her certainty apparent.
“I don’t know, but it wasn’t me,” I complained, desperate now.
Denise dismissed me with a wave of her meticulously manicured hand.
“I’m afraid I have no choice but to document this and put it in your written record,” she informed me.
My spirits sank and my shoulders sagged with defeat.
Now my job was really on the line.
Who was setting me up? And why? I knew I wasn’t that popular, especially with the women at the bank, who viewed me with disdain or a mild contempt.
Was it Ashley? She was a logical choice, from a motive perspective. But somehow, I couldn’t imagine her bothering with something like that. I doubted she even knew about kinky fetishes like sissies and spanking–she seemed too vanilla for that.
Still, she was the only one close enough to have had access to my computer…
“I’ll need you to sign here,” Denise indicated on the form with her long nailed finger.
It seemed so surreal and ironic–and not in a good way, that the woman of my dreams was being instrumental in the destruction of my job here at the bank.
With angry silence, I snatched up the pen and scribbled my signature on the document.
“You are being given your final warning, Mr. Jones,” Denise told me, “if you are found with porn sites on your computer again, you will be terminated.”
My face flushed with hot shame and anger.
“But I didn’t do anything!” I whined.
“And I better not hear again that you are leaving your station without informing Ashley,” she added, pouring more salt on the wound, “Do you understand me?”
“Yes, Ma’am,” I answered, my head hung low.
“That is all. You are dismissed,” she said as she signed below mine and handed the pen to Ashley.
I got up and looked over only long enough to see a look of smug satisfaction on the latter’s face.
Even if my job wasn’t ruined, I knew that by this time tomorrow, my reputation would be, thanks to Ashley. Everyone would be certain I was a closet sissy that couldn’t even wait to get home to surf for the humiliating porn.
I felt tears threatening to erupt and I quickly made my exit, rushing to the bathroom to hide my face from the others.
There had to be some solution to stop my downward spiral, but what?
For the next several days, I felt strong feelings of anger and resentment toward Denise and I went out of my way to avoid her, for what I saw was her role in betraying me at work.
And yet, she seemed oblivious to my change of attitude. She kept sending me crude, dirty messages via text, like ‘I want to cum in your mouth’, and ‘I miss your lips around my cock’.
In my anger, I simply ignored them and went about my day.
To make matters worse, I was wetting the bed at home almost every night. I didn’t want to wear diapers, because they were humiliating and reminded me of Denise, but my sheets were getting stained and my bedroom was starting to smell of stale pee. I couldn’t understand why I was having such difficulty controlling my wetting and my shameful pre-teen years came back with a vengeance to haunt me.
At work, I felt conflicted and confused. The first few days after my write-up, I was too angry to think about Denise but at the same time, it was also impossible to ignore her. She’d come over to my station, the key to my chastity device hanging on a small chain that dangled above the deep line of her cleavage, which, because I was so short, was nearly eye level for me.
And like every other male, I couldn’t resist gazing lustfully at her big, proud breasts, barely contained within her silky white blouse. It was absolute torture!
From every angle, she was magnificent to behold.
And beyond my unrequited arousal, I felt, despite all my misgivings, that I was starting to fall in love with her. I knew my lack of previous relationships with women was a big weakness, because now that I had being shown some attention by someone as desirable as Denise, I was totally helpless to resist her.
Every time she winked at me or smiled when no one was looking, my heart skipped a beat and I was wracked by an intense longing for her.
I remained conflicted and in doubt until fate conspired to force my hand.
I was working at my station during the midmorning rush when, totally unexpectedly, I suddenly felt the front of my pants getting warm and wet. I gasped in horror as I looked down to see a big wet spot forming in my slacks. I was able to stop the flow, but to my dismay, the damage was done. There was no way I was going to be able to hide the accident–I was going to have to leave and go home to take care of it. And I knew the only person that was able to approve something like that, was Denise.
For the next ten minutes, I stood as close to the counter as I could to hide the evidence, cursing my lack of control and hating the fact that I was going to have to go crawling back to Denise and beg to be allowed to leave in the middle of my shift. Not only that, it was going to be tricky just to cover the distance to her office without anyone seeing the dark spot on the front of my pants.
Finally, marshaling my courage, I grabbed some papers, putting them in front of my groin, and asked Ashley if I could be excused to see Denise about a matter of importance. Did I mention that I hated sucking up to her? Fortunately, she was busy with another customer, and she dismissed me curtly with hardly a glance.
I strode briskly over to Denise’s office, relieved to see that her door was open and she wasn’t with someone. I ducked inside and closed the door behind me.
“Denise–I had an accident!” I blurted out in a panic.
She looked up from her work and her gaze fell upon the dark patch in the front of my pants. Immediately, she burst out laughing, showing her perfect white teeth and I blushed hot red with shame.
“Aww, did Mommy’s little baby wet his pants?” she asked in a syrupy voice reserved for children.
I fumed and shuffled my feet, unable to reply with anything dignified.
“I don’t know what happened–I just…I mean…this has never happened before,” I tried to explain.
Denise looked unconvinced and she smiled back at me.
“This is what happens when little sissies like you don’t wear their diapers like they’re supposed to,” she told me.
I bite my lip and stared at the floor as my cheeks burned with humiliation. The last time this had happened, was when I was in the third grade, and I still cringed with shame when I recalled Ms. Taylor’s condescending treatment of me.
“Um, do you think I could, um, leave to change my pants at home?” I asked tentatively.
Denise crossed her slim arms over her magnificent chest in a sign of doubt.
“I don’t know Chrissey…who will fill in for you while you’re gone? I can’t give special treatment to just anyone–the others might think I’m showing favoritism towards you.”
“I’ll only be 20 minutes,” I pleaded desperately, “and then I’ll be right back.”
Denise stood up from behind her desk and she slowly came around to stand before me. For some reason, the crisp click of her high heels on the hardwood floor seemed particularly loud in the quiet room.
I looked up into her pretty blue eyes, aware that I was totally at her mercy. I felt like I were standing before Ms. Taylor again, asking to be excused from class.
But there was no way I could go back out and work with my pants so obviously wet.
“Well…” she began, appearing to consider an option, “I think there might be a way we can come to an understanding…”
She smiled down on me coyly, as she reached down and began snaking her lacy panties down her firm, silky thighs.
“On your knees, Chrissey, I think we can make some sort of arrangement.”
I felt her slim hand on my shoulder pushing me down to that all-too-familiar position of subservience and I looked around me in a panic.
“B-but, shouldn’t we lo-lock the door or something?”
“I’ve always wanted you to suck my cock in my office,” she replied with a chuckle as she began stroking herself, “and the excitement of possibly getting caught only adds spice to the situation.”
“I don’t think–I mean–” I stammered nervously.
“Better work quickly, Chrissey,” she smirked as she looked down at me, her semi-hard cock in her hand, “before someone comes in for something.”
In a frantic panic, I wrapped my lips around her massive tool, swirling my tongue over her warm, thick head as visions of one of our co-workers discovering us swam through my head. My cheeks flushed with shame as I imagined the look on their faces, were they to find me on my knees, slobbering on a big thick cock in my mouth. I would never live that down in a million years! I’d have to move out of town if that were to happen!
Like a demon possessed, I went to work on her cock, using my hands to stroke her big, meaty shaft while my mouth sucked and slurped on the fat head. Denise moaned deeply and I knew I was having an effect on her. If only I could get her to cum quickly, I might avoid the catastrophe that she had so carelessly risked for us.
My head was bobbing up and down, my saliva working overtime as my heart beat wildly within my chest. At any moment, someone could come barging in!
Denise had moved her hands down to guide my head, and she slowed my frantic pace to a rhythm of her own choosing. I was impatient to get the job done, but on the other hand, experience dictated that she would cum sooner if she, rather than I, controlled the way things went.
I heard voices outside the door and I nearly choked in panic. Was someone about to come in??
My cheeks blazed with flaming humiliation.
Denise heard it too, and she grasped my head firmly.
“Keep going cocksucker…that’s my little sissy…I’m going to make sure you get a big mouthful of cum…show me what a good little cocksucker you are…”
Her humiliating remarks made me blush with shame even deeper but I had little choice but to finish the job at hand.
Finally, I felt the familiar sensation of her mighty cock swelling in my mouth and she soon erupted with a barely muffled moan, choking it back so as not to let everyone outside know what was happening. She filled my mouth with warm, creamy semen which I gulped down, only to be dwarfed with a second, even bigger load. That too, I swallowed but she pulled her cock out and proceeded to spray my face with the last of her milky ejaculation.
Reflexively, I moved my hands up to wipe it off but she pushed my hands away, and using her still hard cock head, she smeared her cum across my lips and face.
“Lick that up, sissy boy,” she told me breathlessly.
Obediently, I did as I was told and quickly rose to my feet, extremely humiliated, yet relieved we had gotten away without getting caught.
“Okay, I think we can allow you to leave for a quick break to take care of your pants,” she said with a superior wink.
My cheeks still burning, I hastily cleaned my face up before heading out the door.
The next couple of days, I managed to keep from peeing my pants at work, although to my frustration, I was still wetting the bed at home every night. Being somewhat stubborn by nature, I refused to admit I had a problem and I simply ignored the growing smell of stale pee that greeted me every time I walked into the door of my apartment.
At work, my reputation, which at one point, had risen me to the enviable status of a rock star, had now plummeted to below what it had been before I started going out with Denise. Whereas before, I had just been considered a geeky loner, now I was considered a diaper dependent sissy with a fetish for bizarre porn.
What few friends I had acquired now shunned me, and all the girls looked at me like I was some sort of freak.
I was still going over to Denise’s house about three times a week but she never explained what the builders had been doing there, what they were working on, or the many packages that I saw arriving in the mail when I came over. The room they had been in remained locked whenever I was around and when I asked about it, Denise merely shrugged and replied with something vague, like “it’s storage”.
I was working at my teller station, anxious for the hours to pass so I could flee my humiliating work conditions when unexpectedly, I received a short and simple text message from Denise;
How would Mommy’s little baby like to cum tonight?
My heart skipped a beat and I snatched up my phone, punching the letters so frantically, I had to re-type it three times. After telling her of my enthusiastic agreement, she instructed me to show up at her place at 8.
For the rest of the afternoon, I willingly endured the pain of the spikes in my chastity device whenever Denise came by my station teasing me with her fabulous body. I reasoned that soon enough, my little penis would be free and I would finally, at last, get the relief I needed so badly. In the back of my mind, I hoped that Denise didn’t have some trick up her sleeve but I could only hope for the best.
That night, I showed up at her place, dressed in my best clothes, a suit jacket, pressed slacks and crisp collared shirt. After giving me a long and affectionate kiss, she led me through the door and took me to her bedroom.
“Take off all of your clothes and fold them up neatly,” she instructed me.
I was a little surprised, hoping that after having endured everything I had, that I could assume more of a conventional role with her tonight, but then, anything that got that accursed device off me sooner was fine by me.
In moments, I stood before her nude from head to toe, except for the emasculating pink chastity device securely locked around my genitals.
With great ceremony, Denise removed the small silver necklace she regularly wore and brought the key over to where I was waiting. I was giddy with anticipation as she bent down and undid the small titanium lock securing the device.
I exhaled with relief as she removed the spiked tube and worked the cuff ring out from around my sack. Looking down, I saw that my shriveled penis had numerous red indentations from where my head would repeatedly push up against the spikes.
Taking my tiny member between her fingers, she pinched it somewhat hard and giggled aloud.
“Do you ever wonder if the girls at the bank know just how small you are?” she asked with amusement.
I shifted my feet nervously, wondering in the back of my mind if she was subtly implying that she had already told them. I blushed crimson, the very notion that Denise would share such a humiliating and private detail of my life with them.
“You-you didn’t tell them, did you?” I bleated.
Denise giggled, but didn’t reply as she led me over to the bed and sat me on a waiting stack of soft but very thick diapers.
“It’s time I got my little baby dressed for this evening,” she said with a devastating smile that washed over me like a tidal wave, “I have a few items that came in the mail I’ve been just dying to dress you in.”
This wasn’t really what I had in mind but as always when I was in her presence, I was helpless to deny her anything.
Taking some baby oil, she began slowly massaging my little member, which quickly responded to her ministrations by becoming stiff and erect. It was embarrassing to see just how small it was, even throbbing and hard, and her running commentary only served to dampen my arousal.
“Look at this tiny little baby stick,” she giggled, “Its just exactly like a little toddler’s… It’s no wonder you’re still a virgin…Did your girlfriends laugh at you when you pulled your pants down?”
I tried to fight the intense blushing of my cheeks as I listened to her humiliating comments. And yet, at the same time, her soft, steady caress of my pee-pee kept it rock hard and stiff. I was at once, extremely mortified and aroused all at the same time!
Dipping her middle finger into a nearby jar of Vaseline, she slowly pushed it up inside my anus, making me squeal like a little girl with surprise.
“Ever had a man take you here?” she asked with a knowing smirk as she plunged it in and swirled it around.
“No!” I replied hotly, angry and humiliated that she would imply such a thing.
“Hmm, well, we’ll have to see about that,” she said as she pulled her finger out. I fumed in silence and looked away as she wiped her hands on a baby wipe.
Taking the container of baby powder, she lifted me up by my ankles and powdered my bottom generously before lowering my legs and getting the front.
“I’m going to let my little baby girl cum in her diapers tonight,” she said with a playful wink, “which is entirely appropriate, given what a big sissy you are, don’t you think?”
It was so humiliating to be treated by her like this, but I didn’t want to give away my one good chance for relief by saying something that would anger her. I just had to do my best and go along with it, and besides, no one else was ever going to find out about how I had achieved my orgasm.
I nodded my head in shameful silence, wishing I had the backbone to stand up to her bossy personality.
Pulling the big, soft fluffy diaper up between my legs, she pinned it securely on either side of my hips.
“That’s mommy’s little baby,” she praised me, “Such a good little baby girl you are.”
My cheeks reddened all over again as she pulled out some nursery print, snap-on plastic pants, positioning them at my feet.
“Aren’t these cute?” she asked in her syrupy voice, “They’re perfect for when baby is taking his nap and mommy needs to check his diapers. I’m sure a chronic bedwetter like you can totally appreciate that feature.”
I whimpered weakly as she snuck them up my ankles and over my smooth, hairless thighs.
Even though this had come to be something of a ritual for us, it was still mortifying as an adult to have her treat me like a helpless, incontinent little infant.
I bit my lip with embarrassment as she fitted them up over the fat, bulky diapers, working her long nails around the waistband to make sure all the soft cotton cloth was contained inside.
“What a good little girl you are,” she said again as she beeped my nose and began putting some pink lacy anklets over my feet.
“Look what came in the mail for you today,” she exclaimed as she held forth a pair of white glossy Mary Janes with buckles, “These will go perfectly with the cute little Sunday school dress I’ve been waiting to put on you.”
I cringed and pouted fussily as she easily put the sissy style shoes on my feet and buckled them in place. I looked down at my babyish lower half, knowing my child-like penis was buried between layers of bunny soft cotton Birdseye.
Denise turned around and then brought over a pink gingham little girl’s dress, with a built in petticoat that flared out the very short hem.
“Isn’t this the cutest little thing you’ve ever seen?” she gushed proudly, “It’s like it was made just for you.”
I whined with protest as she forced my arms up and dropped the frilly confection down over my torso.
“It even smells wonderful,” she beamed down at me, “I got that baby powder scent from a company called Eternal Essence–it’s like the perfect perfume for diapered sissies like you.”
My cheeks flushed as they attained an even deeper shade of red. True to her word, the powerful scent of a baby’s nursery surrounded me and I squirmed in place with embarrassment.
As she zipped up the back, she slipped a small lock into the very top, snapping it shut.
“The seamstress was very thoughtful to have put a pair of eyes up here on the neckline so that it could be locked in place–that will make sure mommy’s little sissy doesn’t get any ideas about removing her dress until I say it’s time,” she said with another wink.
I bunched my fists in mute frustration, helpless to prevent her from dressing me up like a little baby girl.
“And last but not least,” she said grinning as she held up a pair of lacy pink panties before me, “this little ensemble wouldn’t be complete without the piece-de-resistance.”
I whimpered impotently as she held them in place for me and brought them slowly up my legs, teasing me again as she did so.
“If only Ashley could see you now,” she said with a chuckle, “Just think what she’d say!”
I felt the blood in my cheeks expand to my ears and chest as I imagined myself standing before my co-worker, dressed in all my little girly, babyish finery.
After easily slipping the stretchy panties over my fat, bulging diapers, Denise stood me up and led me over to the full length mirror against the far wall.
“Take a look at yourself,” she insisted with a big smile of satisfaction on her beautiful face, “Aren’t you the most precious little baby girl that ever lived!”
She stood behind me and reaching down, she squeezed the thick seat of my diapers making me squeal in my high pitched voice.
“This is the real you, Chrissey…not the boy that came over tonight masquerading as a man, but a diaper wetting sissy who belongs in baby dresses and lacy panties.
“We both know that’s where you belong.”
My blood felt hot on my face and chest and I bunched my fists in anger and frustration, petulantly stamping my foot on the ground.
“No!” I snapped, “I do not!”
Denise laughed but reached down and planted a big wet kiss on my cheek, leaving a red lipstick imprint.
“This is how you’ll be dressed whenever you’re at my house, so you better get used to it.”
Giggling with amusement, she turned me around and swatted my bottom, sending me back like an errant little child to a seat next to her bed.
“Okay Babykins, here’s your big chance,” she said as she took a seat opposite me, “You have three minutes to cum in your diapers before I pull them down and lock your little penis back up in your chastity device.”
I gasped and looked around the room, as if expecting some other solution to inexplicably present itself.
“Ju-just like this?” I stammered uncertainly.
“Mm-hm, just like that–just imagine you’re back at home and looking at sissy porn–do what comes natural,” she told me.
“Bu-but I can’t…not with you…you know…watching,” I whined.
“Better make it quick, Chrissey–the clock’s ticking,” she smirked as she gazed down at her watch.
With a gulp of despair, I spread my legs and reached down and began tentatively rubbing the front of my thick diapers over the plastic panties. Secretly, I had to admit that the fluffy soft cloth felt wonderful against my newly freed penis, but it was still tremendously humiliating to fondle myself in front of Denise, who was not only my girlfriend but also my boss at work.
As I began rubbing myself, powerful sensations of arousal filled my being and my breathing soon became labored.
“Oh wait!” Denise said as she stood up and came over to me.
Taking my pink lace panties, she yanked them down around my ankles.
“There. Now you look just like the little sissy masturbator that I always knew you were.”
My cheeks flushed with shame and I momentarily stopped playing myself.
“Better not stop now,” she warned me, “you’ve only got two minutes left.”
I gulped and renewed my efforts, rubbing the front of my plastic covered diapers with abandon. In no time, my heart was pounding in my chest and I was breathing heavily again. The soft, pillowy Birdseye material felt so incredibly wonderful against my little pencil, it was an entirely new sensation for me.
Denise giggled as she crossed her legs and sat back, enjoying the view of her diapered sissy baby, frantically masturbating like a horny adolescent school girl.
I looked down at the fat diapers I was rubbing, reveling in how deliciously erotic they felt, only to look up and receive the shock of my life.
Denise was sitting there, snapping pictures of me with her cell phone as she chuckled with glee!
“Stop that!” I cried as I rose to my feet and stormed over to her.
Denise tossed her long hair out of her face with a shake of her head while holding her cell phone out of arm’s reach from me.
“Is my baby saying she’s ready to be put back into her chastity device?” she asked.
I shook my fists with frustration, my little boner having shrunk back down from the fear of my being exposed with such incriminating pictures.
“Go ahead baby,” she taunted me, “You can sit back down and play with yourself for another minute or I can pull your diapers down and put your chastity device back on–it’s up to you.”
Her smug, superior smile made me burn with resentment–I hated being so completely helpless to her will. But on the other hand, I had been so close to cumming, I was desperate to finish the deal.
Sighing with defeat, I walked back over and sat down on the chair, my thick diapers forcing me to waddle.
“Go ahead sissy, show mommy how her little baby likes to play with herself.”
No sooner did I begin fondling my diapers again when she pulled her phone out and began taking more pictures of me. And once more, my weak will prevented me from doing anything to stop her. Instead, I rubbed myself furiously, hoping to achieve that elusive orgasm before my minute was up.
I blushed with utter shame as I imagined the images she was taking of me, my panties tangled around my ankles as I spread my legs and rubbed the front of my diapers. At that moment, nothing was more important to me in the world than spraying my creamy load into the soft, welcome embrace of my babyish underwear.
I was panting like a dog, my head swimming with erotic abandon. My orgasm was bubbling up, ready to explode gloriously in a shattering climax like I had never experienced in my life. My eyelids became heavy and I felt filled with euphoria–this would make all the humiliation I had suffered and endured worth it.
Suddenly, Denise’s voice cut through the air, abruptly derailing the freight train of my impending orgasm.
“Time’s up!” she announced, “Looks like my little sissy didn’t have to cum that bad after all.”
“NOOO!” I cried, “Please De-I mean, Mommy–please just give me thirty more seconds,” I begged her piteously.
She stood towering over me, her hands on her curvy hips as she looked down at me, an unsympathetic look on her pretty face.
“Chrissey, I gave you more than a fair chance, and you blew it,” she said firmly, “Now we’re going to do things my way.”
Before I could respond, she grabbed a tuft of my hair and forcefully pushed me to my knees.
“Time to do what you do best,” she ordered me roughly.
I whimpered and protested as she yanked her panties down and pulled her skirt up to reveal a big, thick hard-on staring me in the face.
Without hesitation, she shoved the fat head of her cock deep into my mouth, practically choking me.
“Suck it, sissy,” she hissed.
My cheeks bulged as I struggled with her titanic member filling my mouth and it muffled the panicked, girlish squeal I made.
Adjusting quickly to breathing through my nose, I began moving my head up and down her meaty shaft, caressing the underside with my tongue.
The tip of her head had a bead of pre-cum on it, which served to awaken my saliva glands. In no time at all, I was bobbing up and down like a cheap whore, her massive piston slick and wet with my juices.
“Ohhh…that’s it…that’s my little cocksucker,” Denise moaned, “This is right where you belong…on your knees with a big cock in your mouth…”
She emphasized her point by grabbing my head and slamming her fat hard-on all the way into my throat, gagging me on purpose.
“MFGHHHHH!!!” I squealed, before she relaxed her grip and let me resume my rhythm.
“Okay sissy,” she said throatily, “Stand up, come on–stand up,” she ordered me.
Momentarily confused, my mouth was still in the shape of a big ‘O’ as she popped her big cock out of my mouth and helped me back to my feet. My chin and lips were wet with saliva and I could still taste her pre-cum coating my mouth. Leading me over to the bed, she turned me around and pushed me over it, none too gently.
“Stay right there,” she commanded as she yanked my plastic pants open with a flurry of snaps.
“Wha-what are you gonna do?” I quivered.
Without answering me, Denise unpinned my diapers and let the back fall down between my legs, although bent over as I was, my little penis was still pressed up against the thick, soft, cotton cloth in front.
With her high heeled legs, she forcefully kicked my feet apart and my bare bottom was exposed and ready for punishment.
“Please don’t spank me, Mommy!” I wailed pitifully, “I’ll do better next time, just give me another chance.”
“Don’t worry baby, you’re getting another chance, just not the kind you were hoping for.”
I watched in horror as she dipped her tremendous cock into the jar of Vaseline and then took up a position behind me. Shaking my head violently, I pleaded with her to reconsider as she flipped up the back of my dress and using her hands, spread my cheeks wide.
“Oh no–oh no Mommy!” I squealed.
She pushed a big dollop of Vaseline into my hole, followed by another.
“Your virgin days are over, Chrissey–I’m going to pop your cherry tonight,” she said with a wicked grin.
“NOO! No–please!” I wailed, “Please Mommy!”
I felt the fat, warm tip of her organ pressing urgently against my small sphincter and I pinched my cheeks shut in a desperate bid to prevent her entry.
“Noooo!” I cried.
Reaching over, Denise picked up the oval shaped paddle on her night stand and she brought it down hard, swatting the right side of my bare bottom harshly.
“OWWW!!” I howled.
Using my distraction as my bottom momentarily relaxed, she pushed with determination, hard against my hole and I felt her gigantic head push past and plunge deep inside me. My eyes went wide and I gasped again in shock. Gripping the bed sheets frantically in my hands, I sobbed with defeat.
Denise moved slower now, pushing her big monster deep up inside me, stretching my hole tightly like it had never been stretched in my life. It felt like she was shoving a baseball bat into my pouting rectum.
“OHHHHHH!!!!” I moaned.
“There…” she whispered breathlessly in my ear, “Mommy’s little baby is getting just what she needs.”
I struggled to try and get away but between being bent over the bed and having her weight upon me, I was completely helpless. I moaned weakly as she ground her giant cock against me, pushing it in as far as it would go until it bottomed out.
Looking up, I saw our reflection in the big mirror covering the opposite wall of her bedroom. I looked so weak and pathetic, whereas she looked powerful and strong, the very picture of feminine superiority. Here I was, wearing a little girl’s frilly Sunday dress, holding onto the bed sheets for dear life as Denise stood imperious and proud, a smug smile on her face as she slowly pumped my aching hole.
“You see who’s in charge in this relationship? Not you sissy boy–I am,” she said firmly.
She emphasized her point by smacking my stinging bottom cheek again with the paddle and making me cry out in pain.
A tear trickled down my face and I groaned as I felt her plunge deep inside again.
“Your job is to take my cock–however and whenever I want you to.”
I let out a weak moan of defeat and acknowledgment. I couldn’t believe I was a 22 year-old virgin who’s first real sexual experience was being helplessly raped from behind.
I squirmed again with all my might but she slapped my bottom and forcefully rammed her phallus deep inside me again.
“UUUGHHH!” I sobbed.
“So if I snap my fingers at you at work, you better make haste to my office and get on your knees. You’ll be my little bitch and suck my cock whenever it suits me.”
My cheeks reddened as I pictured myself being at her beck and call, constantly at risk of being discovered I was a sissy cocksucker.
Grasping my hips, she began humping me purposefully, in and out, the long thrusts of her gargantuan shaft making me whimper and moan like a weak little school girl.
Looking up at our reflection in the mirror, I saw the disparity of power between us. I would never be her equal, in or out of the bedroom. She would always be the one calling the shots while I was forced to do her bidding. She held all the cards and I held…nothing.
“This is what happens to weak sissies like you, Chrissey–they get bent over and ass fucked like emasculated little boys. And you’ll take it because it’s the only sex you’ll ever get,” she explained in her bossy voice.
She slapped my right cheek again hard with the paddle.
I howled out and struggled against her but it was hopeless. As usual, Denise had complete control over the situation, like she did with everything in her life, and she was going to make sure I got what was coming to me.
Her paced changed and began to get more urgent as she dug her long nails into my bare hips and thrust her huge member harder and harder into me. I was moaning and crying, alternately slapping the bed mattress and gripping the sheets for comfort.
“Does baby Chrissey need his teddy bear?” she taunted me.
Her pretty face held a dark fire I’d never seen before–one of absolute power, like a lion that had cornered her prey and was about to lunge for the kill.
My poor hole was being stretched so wide from the battering ram of her cock and it ached like nobody’s business. And yet, somehow, I was getting a sensation of fulfillment like I’d never had before. My own little penis was rubbing against the soft cotton cloth beneath me and the weeks of deprivation meant the stimulation in my punished anus was translating to stimulation for my penis. I was deeply ashamed to admit I was getting turned on but I couldn’t help myself.
Denise pounded me relentlessly and I felt my own orgasm starting to become imminent too. I felt her big balls slapping my own as she fucked me hard and relentlessly. Looking up at her in the mirror, she looked so powerful and beautiful, a patina of fine sweat on her brow which was creased with concentration.
At some point, the aching in my hole became transformed into pleasure and my head was swimming deliriously as I felt myself teetering on the edge of my climax. I looked up to see Denise closing her eyes and I felt her big tool swell inside me.
Shrieking like a banshee, she plunged it all the way until it bottomed out, filling me with a warm, gooey enema. At the same time, I toppled over the edge myself, squirting my little load into the welcoming folds of my baby soft diapers.
As Denise spent herself, she collapsed on top of me, her fat, hard-on still buried inside me.
Both of us were breathing heavily, and she leaned into me, kissing me gently on my ear.
“Well Chrissey, you’re no longer a virgin,” she whispered with a chuckle, “And you have a nice tight, sissy ass that I’m going to enjoy taking on a regular basis.”
I blushed hotly and whimpered weakly in response.
Now that I had cum, I became acutely aware of her shaft stretching my hole to the limit and I mewled painfully. Sensing my discomfort, Denise pulled out and I let out a tremendous sigh of relief as her slippery tool slid out of me.
Turning me over, Denise lay down next to me, her finger reaching over to gently describe a line from my ear to my chin.
“How did my baby like her orgasm?” she asked me sweetly.
I blushed to think of how my orgasm had been achieved, not something I was ever going to be able to brag about. I also became aware or a warm river of semen oozing out of my hole, reminding me of my new status.
“It-it felt good,” I confessed ashamedly, my cheeks burning a hot shade of red.
It was true at least that I felt a strong sense of relief that I hadn’t had since I last masturbated some four weeks ago.
Pushing me over on my back, she knelt down and gave me the most sensuous kiss I’d ever experienced in my life. I sighed happily, my feelings of affection and love for her impossible to ignore.
Bending down, Denise gathered the pieces of my pink chastity device and began working the cuff ring over my genitals.
“Couldn’t we…you know…leave that off?” I asked timidly.
“I don’t think so, Chrissey,” she said firmly, “You’d be masturbating first thing tomorrow morning.”
I gritted my teeth with resignation as she fitted the tube onto my shriveled penis and mated the pins into the corresponding holes. Slipping the lock through the central pin, she clicked it shut and put the necklace with the key back around her neck.
“And now, it’s time to get my baby bedwetter dressed for beddie-bye.”
Grabbing my car keys and closing the door of my apartment behind me, I was struck by the difference in the air outside. Or rather, how different it smelled from the pungent air inside my single room dwelling being affected by my thoroughly pee-soaked and stained mattress.
My wetting hadn’t abated and I was seriously thinking I would have to start wearing diapers full time for nights. I absolutely hated the idea that I had no control over something like that at the adult age of twenty-two but what was I to do?
I walked the far way around the building to my car, purposely avoiding my apartment manager’s room so as to avoid her seeing me. Once again, I was late on my rent, and I was running out of excuses.
Nevertheless, I was in good spirits. I had received a text message from Denise that morning that was still making me swoon with desire;
I can’t wait to have you nuzzling my cleavage again. ;o)
It was followed by two pink hearts.
I sighed with contentment. I think I was in love.
I knew Denise wasn’t perfect–she had her flaws just like anyone. But I reasoned that her good points more than made up for her down side. Yes, she had taken part in my write-up at work, and to be sure, our sexual relationship was anything but conventional. But no one else knew about that side of her and besides, where I was I ever going to find a perfect woman like her? It would never happened again as long as I lived.
She was so pretty, and sexy, and awesome in every way. And when she smiled at me my heart sang with joy. I could easily forget about the many humiliations she had made me suffer through, if only to get that sign of approval from her when we were alone.
I pulled into the parking lot at work and locked my car, bringing my small sack lunch along with me.
I was just turning the corner of the building when I received a rude shock that froze me in place like a statue.
There, against the wall, I saw Jordan and Denise, locked in a wildly passionate embrace with their mouths eagerly pressed against each other’s, French kissing amorously as if they were in a bedroom instead of a very public place.
I gasped and my mouth hung open as I stared at them in disbelief.
Jordan’s back was against the wall and Denise had her hands pinned against it, as if she was forcing herself on her beautiful blond friend. However, that seemed highly doubtful–Jordan’s hands soon began freely roaming over her boss’s sexy body, exploring her shapely ass and cupping her big, heavy breasts.
I staggered back and tried to grapple with the enormity of what I was seeing. Obviously, the relationship between the two of them was far more developed than I had ever imagined. And just as obviously, it put my own relationship with Denise in a whole new light.
My entire being was blazing with an all consuming fire of jealousy, competing with alternating emotions of anger and anxiety.
How could she do this to me? I wanted to burst into tears and it was only with great difficulty that I pulled myself together.
As I staggered drunkenly into the bank, I walked in a daze, my heart turning somersaults. I ignored the usual disdainful stares of my co-workers and went to my station, trying desperately to focus my mind on my job.
About ten minutes later, I saw Jordan coming in, fixing her hair and makeup, her face still flushed from whatever they were doing out in the parking lot. Needless to say, she was very late by now for her shift, but I thought it extremely unlikely that anyone was going to hold her accountable for her tardiness.
I glared at her with unremitting hatred and envy. She had never given me the time of day ever since she first started working here and now I had a whole new reason to resent her.
For the rest of the morning, I was tormented with the vision of those two making out and it gnawed at me like tiger on my leg. My emotions surged from despair to raging anger, back to despair again. It was just so unfair that finally, after finding someone that I thought was perfect, that I should discover that she had feelings for another person.
What was I to do? I wanted to break up with her, but deep down, I wasn’t sure if I had the necessary emotional fortitude to do it. I felt helpless in the grip of her attraction, unable to stand up to her or demand she treat me with respect. The fact was, I felt weak in her presence and even now, I found her very intimidating.
All morning I could think of nothing else and my work suffered for it. Four times, customers complained I had given them the wrong change and once it even came to Ashley’s attention. I knew I was on thin ice with her and I struggled with difficulty to concentrate on my job.
I was with an older lady and trying to deal with that transaction when I saw a previous customer come up to Ashley’s station. An exchange followed in which the lady accused me of mishandling her funds and after taking care of it, Ashley turned to face me.
“Chris, what in hell are you doing today? That’s the second mistake I’ve had to deal with just this morning alone. We don’t hire people to play willy-nilly with our client’s cash.”
She was scolding me and my face was getting red as people were turning to look at us. Ashley was never one to turn away from making a spectacle and this one was turning into a doozie. I feared Denise or Mr. Jenkins would overhear and feel compelled to get involved.
“Don’t you realize how important the funds are that we handle here? It’s not just babysitting money to them…”
Her voice trailed off as I saw her gaze look past my shoulder to the computer screen behind me. Her mouth hung open in midsentence, registering the shock that was apparent on her face. I had no idea what she was looking at but her features darkened even further and her mouth tightened in a grim line.
With mounting trepidation, I slowly turned around to look at my computer. Due to inactivity, it had gone into screensaver mode except that instead of displaying the usual moving picture of the bank logo, I was now watching a slideshow presentation of pictures of myself. My mouth dropped open as I stared in horror at my image, dressed in the pink Sunday school dress, lacy panties tangled around my ankles as I was frantically rubbing the front of my bulging, fluffy diapers.
I gasped in shock as the image was replaced with a close up of the side of my face, Denise’s monster cock buried to the hilt as my cheeks bulged to accommodate her.
“That-is-it!!” Ashley shrieked, “I am going to make sure you get your ass fired!”
My heart was in my throat and I was stammering out an incoherent response when Denise suddenly appeared behind Ashley.
“What’s going on here?” she asked suspiciously.
The rest of the tellers were looking now too and several of them could plainly see the incriminating images on my screen.
In an instant, it all became crystal clear to me.
Denise had been behind this from the very beginning. I still wasn’t sure how she’d accomplished it, but the first night I had been at her house and heard what I thought was a camera shutter, she had been secretly her taking pictures of me. And then the blatant cell phone photos she’d taken the other night of my masturbating had obviously been intended to supplement those.
I was so utterly mortified, I was on the verge of tears. My mouth was moving but I couldn’t say a thing. That was until I saw Ashley’s gaze drop down to focus on my pants. Looking down, I saw the dark wet patch increasing in size as I helplessly wet myself like an incontinent toddler.
Heather, one of the other tellers, had come over to see what all the commotion was about and she shook her head disdainfully.
“Looks like someone needs diapers,” she muttered.
My heart was pounding wildly and I blushed red hot with shame. I would never live this down for as long as I lived! Tears tumbled down my face as Denise looked down on me like a little boy who had failed his potty training for the umpteenth time.
However, her expression hardened and she crossed her arms over her big, proud bosom to address me.
“Mr. Jones, it is clear that you are unprepared to handle the adult responsibilities required by this establishment. You’ve been given ample warning about your filthy porn habits and you’ve chosen to disregard them.”
“–You put these on here, you bitch!” I shrieked bitterly as I wiped the tears streaming down my face.
Denise slowly shook her head patronizingly and Ashley angrily pointed her manicured finger at me.
“You are some kind of sick pervert and you should have been fired a long time ago!” she snapped.
I was tempted to argue that the cock shown in my mouth was actually Denise’s but I knew that would never fly, short of lifting her skirt up, which would probably get me arrested, on top of being fired. My shoulders sagged in defeat as she continued to dress me down.
“Effective immediately, you are terminated, Mr. Jones,” she said in her no-nonsense tone, “Please take your things and leave the building at once.”
Looking around me, I saw nothing but contempt and a total lack of sympathy for me on the faces of my co-workers. I snatched up my car keys and headed for the nearest door without bothering to gather up any of my other things.
The entire front of my pants were soaked and I tried to shut out the sniggering comments being made at me as I pushed through the crowd around my station. Everything was in a blur and I was going on instinct alone.
I ran to my car and started it, jamming the key in and mashing the gas pedal to the floor. Swerving wildly out of the parking lot, I only narrowly missed a soccer mom and her kids in a van that was heading down the street at that moment. I drove through the streets recklessly, not caring whether I ran through stop lights or crosswalks.
By some miracle, I got home without being arrested.
Getting out of my car, I violently slammed the door shut and strode across the parking lot to my apartment. My anger was soon replaced by grief and shame and I hung my head in despair as my pace slowed to walk up the steps.
Because I was looking at the ground, instead of where I was going, I failed to see my apartment manager waiting for me at my door.
“Well, looks like you’ve had quite a day,” she sneered.
Looking up, I saw her standing defiantly in front of me, a slip of paper in her hands.
I had never really known Tasha, the woman who ran our apartment complex, although we had had a few brief exchanges. I knew she didn’t think much of me and of course, I resented her for that.
She was about thirty-something, slim, with long brown hair and a very attractive face. In other circumstances, I might have tried flirting with her but putting aside her distaste for me, she was way out my league anyway. I was used to being treated like trash by beautiful women and Tasha was just one more example in a long line of females throughout my life.
“This is your written eviction notice to vacate the premises. You have five days to clear your stuff out before I call the sheriff,” she said sternly.
Walking past me, she shoved the paper in my hands and strode off without another a word.
Looking down, I sighed heavily as I gazed at the harsh notification, so impersonal and final.
I fumbled with my keys and opened my door. This day had gone from good, to bad, to worse and now to disastrous. I honestly couldn’t think of how things could possibly be any worse for me.
I had no job, no income, no savings, no girlfriend, and now, no place to live, with nowhere to go.
What in the world was I to do??
And that’s when it hit me…
Denise was still holding the key to my chastity device!!
To say I was between a rock and a hard place, was a woefully inadequate understatement.
Denise was utterly and irrevocably out of my life now, and I still had no more access to my penis than I had when she was my girlfriend. My little member was still locked up tighter than Fort Knox and my chastity cage was going nowhere without getting possession of her key.
The obvious thing, would have been to simply go over to her house and demand she give it back to me but I wasn’t so sure. What if she refused? Worse yet, what if she and Jordan met me at the door and simply laughed at me? I had already suffered more humiliation than a person should have to go through in one lifetime and I wasn’t prepared to endure some more.
But the fact was, I had much bigger problems to deal with than that. I had one day left before I became homeless and I was no closer to being employed than I was when I had gotten sacked. Yes, I had applied at numerous places but due to the nature of my termination and the small size of our town, I was quickly finding out that I was persona non grata everywhere I tried to get a job.
That, combined with the fact that I would soon be without a roof over my head, made my situation increasingly dire. I was wracking my head for a solution and I honestly had no idea whatsoever as to how to proceed. I had 24 hours in which to come up with a solid plan and every hour made me increasingly desperate.
During this time, I found myself pondering what Denise was thinking about me, why she had conspired to get me fired, and why she had shown such an apparent interest in me in the first place.
What was she thinking now? Did she despise me? Did she still like me? In my heart of hearts, I hoped for the latter. But I had no way of knowing without communicating with her. It wasn’t like I saw her any more on a regular basis and her texts had grown silent since I lost my job.
Then again, if I was ever going to cum again, I had to face the fact that she was the only person who had the key I needed. As much as I loathed the idea, it seemed increasingly that I was going to have to make the first move and reach out to her.
After considerable deliberation and much soul searching, I finally took up my phone and punched the thread that had her name on it, typing the following message;
Can I call you?
I must have waited a half hour before getting the courage up to send it and then I finally hit the button.
The phone remained silent for several minutes.
It was infuriating, sitting there waiting for an answer. I kept turning my phone on to see if maybe I’d missed a notification, only to see that nothing at all had transpired.
Finally, after 56 minutes, my phone did its familiar ‘bleep-ba-bleep’.
I scrambled to get it and I shakily scrolled the icon over to reveal the message.
I wasn’t sure how to take that response exactly but at least it wasn’t a flat out rejection.
Nervously, I went over in my mind how I should conduct myself and what I should say. It wasn’t made any easier by the fact that she held all the cards and I had none.
Finally, I tapped the icon to call her and listened to it ring. She answered after the first ring but said nothing into the phone.
“H-hi, Denise,” I began uncertainly.
“Hi sissy Chrissey,” she greeted me cheerfully.
I breathed a small sigh of relief. That was a positive sign, albeit a humiliating one.
“Umm, how-how’s it going?” I asked, for lack of anything else to say.
“I’ve missed you, baby,” she told me.
Despite myself, my heart surged. In that instant, I forgot all about the many things Denise had done to ruin my life and humiliate me. All I could think about was the spectacularly beautiful woman on the other end of the phone that I had fallen in love with.
Before I could say something in reply, she took the initiative.
“Have you missed sucking my cock?” she asked with amusement in her voice. I thought I heard another woman’s giggle in the background. Was that Jordan?
My heart skipped a beat.
“Are-are you with Jordan?” I asked, my voice quivering.
“Mm-hm,” she replied. Although I couldn’t see her, I knew she was smiling.
Once again, a massive surge of jealousy swept through me unchecked, my anger not far behind it.
“How could you do this to me?” I angrily demanded, “You got me fired and now you’re cheating on me with that slut!”
Denise didn’t reply immediately but her voice took on a bored tone.
“Was there a point to this call?” She sounded ready to hang up.
I had thought I would be able to keep my emotions in check but the presence of Jordan had unexpectedly pushed me over the edge. Nevertheless, I still had to resolve my living situation and this was my only chance, slim as it was.
“I’m sorry, I just…um…I mean…” all of a sudden, I felt my emotions getting out of control and I choked up, unable to speak.
“I don’t have anywhere to go,” I sobbed miserably.
“What do you mean?” she asked, her interest returning.
“I’m about to get evicted from my apartment!” I blubbered, barely coherent.
“Awww,” she said in her honeyed voice, “You could stay with me, baby.”
I wiped the tears off my face as I straightened up.
“I-I could? I mean–you’d let me…live with you?” I could hardly believe my ears.
“Mm-hm,” she said pleasantly.
“As-as your b-boyfriend?” I stammered anxiously.
“Well…not exactly as my boyfriend,” she giggled.
Again, I thought I heard Jordan giggling in the background.
“Wha-what do you mean?” I asked suspiciously.
“If you live in my house, you’ll live by my rules,” she said firmly, “You’ll do as I say without question.”
I bit my lip nervously.
“Li-like what?” I asked timidly.
“We can discuss the details when you get here. But first, I have to know that you will agree without question. Otherwise, we’re through talking.”
Her voice had taken on that bossy character that I knew all too well. There was zero room for discussion when she had her mind made up like this.
“Do you agree or not?” she demanded.
I looked around my mostly empty apartment at my ratty furniture and pee-soaked mattress.
“I-I agree,” I replied. What choice did I have? Once again, she had me cornered and checkmated.
“Good. Then there’s something you will have to do to show that you agree that I’m the one in charge here.
“Remember that outfit I sent you home with a few weeks ago?”
I cringed as I looked over at my couch and saw the white and pink ruffled fleece top laying on it.
“Ye-yes,” I answered her.
“I want you to put that on, along with your anklets, Mary Janes, and the biggest, thickest diapers you have. That’s how you will come over here. If I don’t see you get out of your car and walk up the driveway in that outfit, I won’t even answer the door,” she explained to me.
I gulped hard as I tried to imagine how excruciatingly humiliating that would be.
“Bu-but couldn’t I…couldn’t I just put that on when I got there?” I whined.
“Those are my terms. Take it or leave it.”
I bit my finger in angst, knowing I had little choice. It was either that, or become a homeless beggar in the streets. My mind raced as I tried to think of a way out but I couldn’t see any. I was going to have to go crawling back to her on my hands and knees, and dressed in the most humiliating way possible.
I gulped in trepidation and then began trying to think of ways to justify doing it. After all, it would mean room and board, and an end to all my troubles, to say nothing of a life with a beautiful woman. The short ride over would be embarrassing, for sure, but on the other hand, I wouldn’t be seeing anyone here again anyway, I reasoned.
“Okay,” I agreed quietly.
“That’s ‘yes Mommy’,” she corrected me.
“Yes Mommy,” I quickly replied. I could hear Jordan giggling in the background.
“Good. Be here by 4, I want there to be plenty of light still outside.”
“Yes Mommy,” I responded submissively.
“See you then, sissy,” she said before she hung up the phone.
I looked down at the phone and sighed heavily. It seemed that ever since I had met Denise, humiliation and degradation had become a normal part of my life.
With little else to do, I decided I might as well get this over with. I could come back for the rest of my stuff later.
Walking over to the couch, I laid out three of the soft Birdseye diapers Denise had given me, along with some pins and baby powder. She had only given me one pair of plastic panties, a white nursery print with babyish characters on it. It was going to be mortifying to go out in broad daylight wearing them but if this was the price for free rent, I was going to have to do it.
After arranging the cloth diapers in a thick, rectangular stack, I sat down upon them and proceeded to powder myself as I had seen Denise do so many times before. These particular diapers had an absorbent soaker section sewn down the middle and I was amazed as I pulled them up between my legs to see just how bulky they were. They spread my legs apart just like a baby’s and I blushed with the familiar sensation.
Taking the pink headed diaper pins, I pushed them through the soft cloth awkwardly, unaccustomed to having to do this for myself. It took a few attempts before I got the right fit and then I was ready for the plastic panties. Holding them in my hands, I blushed again that I was willingly doing this to myself. What would people think if they were to see me? I tried not to think about it as I slid them up my legs like my usual underwear. I had to work them around the diapers which were so fat and bulky but eventually, all the fluffy, spongy cloth was contained inside the waterproof vinyl.
I put the top on next, a white and pink fleece garment with short, puffy sleeves and a frilly lace hem that came down to about my navel. A diapered teddy bear amongst some building blocks decorated the chest. Very mature indeed.
I went into my closet and found the white lacy anklets and glossy pink Mary Janes, idly wondering to myself where Denise found all this stuff. Sitting down, I slipped the socks and sissyish shoes on, standing up to look at myself in the mirror.
Of course, I had seen myself dressed like this at Denise’s house many times, but this was the first time I had seen myself in my apartment, and more importantly, having agreed to dress in it myself.
I blushed a hot red as I beheld the thickly diapered sissy looking back at me in the mirror, looking like he needed his mommy and a bottle.
I swallowed hard, grabbed my car keys and headed for the door. Was I really going to do this? How many people would see me? I could only hope I would be able to run to the car and once inside, people wouldn’t really be able to pick up on just how ridiculous I looked.
I was holding the doorknob in my hand, afraid to twist it open. With my heart pounding in my chest, I took a deep breath and opened the door. Looking down the second story balcony hallway, I didn’t see anyone in either direction.
With my heart feeling like it was about ready to jump out of my chest, I tried to walk briskly toward the stairwell going down to the parking lot, only to discover that the extreme thickness of the diapers forced me to waddle like a baby. I went as fast as I could, bolting down the steps but then when I turned the corner, who should I find standing there before me, but Tasha!
Her mouth dropped open (as did mine) and she stared incredulously at me, her gaze taking in my pink Mary Janes, baby smooth thighs devoid of hair, my thick, bulging diapers with the shiny nursery print plastic panties, and lastly, the white and pink sissy baby top.
I nearly dropped my car keys but then I felt a familiar and childish sensation happening in my diapers as I suddenly flooded them in panic.
“Oh-my-god,” she said in awestruck shock.
Completely at a loss for words, I tried to move around her but she stepped in my way.
“Whoa there, baby boy,” she said with a smirk coming to her face, “I always suspected you were some kind of weird pervert but I had no idea…”
My face flushed a deep red and I felt another stream of hot pee saturate the cloth between my legs. I ducked around her and fled for my car, her raucous laughter ringing in my ears.
Once again, I was making a panic stricken escape, mindless of my surroundings. Driving like a maniac, I just wanted to get to Denise’s house as fast as I could.
I took the on ramp to the freeway and floored it, accelerating into the left lane as quickly as I could. Keeping my eyes forward, I ignored the cars that were slowing down or speeding up to keep pace with me and see the strange sissy in the driver’s seat.
I had almost reached the exit for Denise’s street when the flashing red and blue lights suddenly caught my attention in the rear view mirror.
With a sinking realization, I knew my day was just about to get a whole lot more interesting.
As I looked with disbelief into the rear view mirror at the red and blue flashing lights closing in, my entire being surged with panic. How was I going to explain my appearance? How could my situation be any worse?
I bit my lip so hard, I almost drew blood.
With my heart beating wildly, I slowed the car and started pulling over to the right lanes of the freeway. Maybe, just maybe, he was after someone else.
But no, he followed right behind me as I made my way over and I knew with sinking certainty that it was me he was after.
My breathing was coming in short gasps and I thought I was going to hyperventilate. What would he do when he saw my sissy top and diapers? I was already blushing a deep red and I hadn’t even stopped the car.
At last, I pulled off the active lane and onto the wide shoulder, shutting off the engine. The policeman had been driving a suburban and he kept the lights flashing as he got out, which had the effect of calling attention to every motorist who should happen to drive by us.
I swallowed hard as I watched him walking toward me, his dark sunglasses making him look all the more menacing. The big cop rested his hand on his gun as he approached and I squirmed in my seat, only to realize I had just let out another stream of pee into my thick, fluffy diapers.
Rolling down the side window, I tried to get my erratic breathing under control. The cop came alongside and looked down at me, his expression darkening as he beheld the ridiculous image of the sissy baby behind the wheel. I couldn’t read his eyes, but his look was that of contempt and displeasure.
Without a word, he put both his hands on his hips and his chiseled jaw hardened.
“What in god’s name are you wearing, boy?” he demanded.
I swallowed hard and tried to say something but my mouth was so dry I could only stammer foolishly.
“Never mind,” he cut me off in a curt tone, “Do you know why I pulled you over?”
I-I-I wa-was speeding?” I quaked, guessing the obvious.
“That’s right sissy boy. Give me your license and registration.”
My face flushed as I suddenly realized that in my haste to get over to Denise’s house, I had left my driver’s license in my pants pocket which was now lying on the floor of my apartment. With my hands visibly shaking, I fumbled for my car’s registration from the glovebox and almost dropped it on the ground as I gave it to the stern officer.
“Driver’s license,” he barked at me.
I felt another stream of pee surge into my already wet diapers.
“I-I-I seem to have, um, uh, forgot it,” I replied lamely.
He regarded me with a fierce expression that made me cringe in fear.
“Looks like your going to be taking a trip to jail today, young man,” he told me simply.
I gasped in horror. There was no way I could go to jail dressed as I was–no way.
“Please! Wait–please, isn’t there something–something we could do?” I was beside myself with panic. I tried to squeeze my thighs together to staunch yet another steam of terror-induced pee into my diapers.
The cop looked at me long and hard without saying a word as he appeared to consider the alternatives. At last, he put his ticket book into his breast pocket and stood back a step.
“Get out of the vehicle,” he ordered.
With my heart threatening to jump out of my chest, I fumbled with the door handle and stepped out, the cars passing by enthusiastically honking at me as they caught sight of my babyish outfit. Looking around nervously, I followed him as he led me to the opposite side of his suburban from the traffic. He then made me face the oncoming traffic while he stood behind me. I wanted to hide behind the vehicle but he pushed me forward so I was next to the rear view bumper, ensuring everyone in the near lanes would get an unobstructed view of me as they drove by us.
I blushed hotly as I stood there, every fifth or sixth car honking at me as they whizzed by. I heard him undoing his belt and unzipping his pants and wondered what exactly he had in mind.
Before long, I felt the waistband along with the back of my diapers being pulled back. I squealed with surprise but the worse was yet to come. I knew I had no choice but to submit to whatever he was going to do to me and in my naïveté, I thought maybe he’d just drop something down the back of my diapers.
It was with mortified shock that I felt a strong stream of hot pee suddenly splashing against my lower back and into the crack between my buns as began peeing into my diaper like it was his own personal urinal.
The cars passing us could probably see his head behind me but it was my full body that they saw as he slowly relieved himself into the thick, absorbent cloth inside my plastic panties.
My face went a bright shade of red and I bunched my fists, stamping my feet in frustration as I stood in place, letting him do his business without any sort of interference. He must have thought me a complete weakling to stand there and do nothing. Somehow, all my previous moments of spinelessness seemed to come back to haunt me, as if to say that all my cowardice in the past had led me to this ultimate of humiliating degradations. To be sure, I was showing absolutely no backbone now or doing anything to discourage this bully.
I could feel his hot pee accumulating in a deepening pool in my seat as the fluffy, soft cotton struggled to absorb it all as fast as it could. I felt the soggy warm wetness seeping in between my legs and up into the crotch of my diapers to surround my little balls and caged penis with his nasty urine.
The force behind his stream was very strong and as it splattered against my lower back, I pictured he must have had quite a big cock. He kept peeing freely, emptying what must have been a very full bladder until it trickled to a halt. And then, just when I thought he was finished, he started with another equally strong stream.
I sobbed with humiliation and felt my eyes filling with tears of shame. My diapers were sagging by now with the weight and I whimpered with helplessness. Who else was so totally lacking in dignity to let another man pee freely into the back of his diapers? But then, who else would have willingly put on diapers, plastic baby panties and a sissy outfit to drive around in public? Obviously, my shame had no bounds.
I waited until he was finally done, and then stood there submissively as he let go of my plastic panties and slapped my thickly diapered bottom roughly as a form of dismissal.
“Run along, sissy boy,” he commanded me.
“Yes sir,” I whimpered in defeat.
In my utter humiliation, I waddled back to my car, holding my diapers on either side to prevent them from sliding down my smooth thighs from the weight of all that pee. With a humiliating squish, I sat in my seat, the warm pee seeming to surround me completely as my snug plastic panties ensured I felt every soaking square inch of my diapers.
I sniffed away the sob threatening to engulf me as I pulled back onto the freeway and slowly took the exit to Denise’s house.
Needless to say, I could never tell anyone what just happened. If she asked–and I knew she would–Denise would have to be told I simply couldn’t hold it anymore and I’d peed my diapers like any other incontinent toddler.
After my humiliating encounter with the cop, I drove much slower, and with a heightened sense of apprehension as I made my way to Denise’s neighborhood. I rebuked myself for forgetting my driver’s license–I wouldn’t be swimming in another man’s pee now if I had just been more careful and less impulsive.
Earlier, I had been dreading my arrival at my former girlfriend’s house but by comparison to what I had just been through, walking up her driveway in my sissy top and exposed diapers was going to be easy.
I hadn’t wanted to move too much in my seat but regardless, I couldn’t escape the cop’s warm pee surrounding me everywhere. There wasn’t one section of my diapers that wasn’t fully saturated and I felt like a toddler who couldn’t be trusted with training pants yet. I was utterly ashamed and part of me even felt like I had gotten what I deserved for my total lack of backbone and my cowardly personality.
Getting out of the car, I closed the door behind me and waddled awkwardly up the paved driveway to Denise’s front door. My diapers were so heavy, they sagged under the weight and I was forced to use one hand to help support them. With my free hand, I knocked on the door and waited nervously, hoping my exposure outside would be as brief as possible.
Before long, I heard the sound of Denise’s high heels clicking on the hardwood floor as she approached. The door opened wide, and I beheld my former boss for the first time since she had fired me so ignominiously at the bank earlier in the week.
She was wearing a snug, form-fitting white skirt and matching crop top that clung deliciously to her big, mouthwatering breasts. In all my trauma lately, I had forgotten just how mesmerizing they were. No wonder I was willing to do anything and everything she had wanted!
Her lovely long black hair spilled over her mostly bare shoulders in big curls but it did nothing to hide the deep, sexy cleavage between her big, proud breasts. Now that I stood before her, I felt foolish and weak when confronted by her power and beauty and I found myself blushing all over again.
She stood well above me, her hands on her curvy hips as she looked down at me imperiously, as if I were an errant child.
“Well…Did my little baby manage to keep her diapers dry for the ride over?” she asked skeptically.
I squirmed and turned bright red with embarrassment. Without waiting for an answer, she stepped outside, physically turned me around to face the street, and squeezed the thick, spongy seat of my diapers.
I squealed with embarrassment.
“Oh my, you are absolutely soaked!” she exclaimed, “You really do need diapers, don’t you?”
My face burned with shame as a neighbor across the street came out to check her mail. The woman looked across to gaze at me and I could see her eyebrow rising quizzically.
“Um, can-can we go inside?” I whined.
Denise answered me by swatting my seat and I stumbled forward clumsily, showing anyone who was watching who wore the real pants in this relationship.
Just as I turned to go in, Jordan appeared next to Denise blocking the way, and she looked down on me, the disdain plain on her face.
“Oh–it’s you,” she said by way of greeting.
I squirmed awkwardly and shifted my feet, not knowing what to say.
“That outfit suits you perfectly,” she remarked, “Just what I’d expect from a big sissy like you who can’t keep his pants dry.”
My cheeks burned with shame as I stood before the two of them, thoroughly humiliated. And to be sure, things weren’t made any better by the fact that the thick diapers I was wearing were sopping wet, only confirming her dismal opinion of me.
“Chrissey, I think you need to tell Jordan what you did,” Denise told me.
Biting my lip, I looked down at the concrete walkway in front of us. I badly wanted to duck inside and hide but she was apparently going to drag this out and make me humiliate myself in front of everyone.
“I-I w-wet myself,” I admitted shamefully.
Jordan shook her head in disgust.
“What a surprise.”
“Don’t worry, Chrissey,” Denise said with a forgiving smile, “Your days of wearing pants are over. Why don’t you come inside and I’ll show you to your room.”
Feeling a mixture of relief and trepidation, I followed them inside but not before looking over my shoulder to see if their neighbor was still there. Sure enough, the woman was still standing by her mailbox, staring at me and trying to figure out what kind of weirdo I was.
I rushed inside, waddling awkwardly behind the two sexy women as they led me down the hall toward the mysterious room Denise had been having work done to previously. As the two of them went in and stepped aside, I entered and looked around in shocked amazement.
It has been re-designed as a nursery, and judging by the pink and white decor, it looked like it was intended for a baby girl, albeit, a rather large one.
An oversized pink crib dominated the room, with a teddy bear nestled cozily amongst it’s Disney Princess baby blankets. Next to it, a low vinyl-covered changing table sat nearby, stacks and stacks of thick cloth diapers and other supplies ready for use along with a short chest of drawers that were open to reveal many pairs of waterproof plastic panties. My stomach buzzed with nervous anticipation.
A shelf containing nursery books and baby toys was to one side and next to it, a folded playpen stood ready for use.
Three sides of the room were wallpapered with designs of baby bears and building blocks while the fourth wall was covered with a mirrored set of closet doors. A warm light shone in through gauzy pink curtains over the only window on the opposite side of the room.
In the far corner, stood a large pink dresser, with dolls lining the top, it’s sides decorated with more playful nursery characters.
Hanging above it on a peg, I suddenly shivered as I recognized Denise’s formidable Spencer paddle, an instrument of discipline I was all too familiar with.
I gasped as I took it all in.
I guess I hadn’t really given too much thought as to what the conditions of my living here would be but I never imagined this!
“This is where a sissy like you belongs and it’s where you’ll be spending the majority of your time, Chrissey,” Denise explained firmly, “Judging by how wet your diapers are, it’s obvious you need them 24/7 now.”
My face reddened and I wanted to blurt out that most of the pee in my diapers wasn’t my doing but somehow, I didn’t think that explanation was going to do me much good.
“Time to explain a few ground rules,” Denise said in her no-nonsense tone, “First, under no circumstances are you to touch your diapers. If either of us catch you doing that, you will immediately get a severe spanking. Your diapers will be changed at our discretion, either by one of us, or one of your babysitters–”
“–Ba-babysitters?” I spluttered, trying to take it all in.
“Yes, babysitters. We won’t always be here to watch over you so I have a number of girls in mind that will be babysitting you when we’re gone.”
She saw the shock and horror registering on my face and a sly smile appeared on hers.
“Oh yes, Chrissey, don’t think for one minute that when people are visiting that your diapers will remain a secret. These are your underwear from now on,” she said slapping my thickly padded bottom, “And we’ll change your wet diapers regardless of company, so you might as well get used to the idea.”
I bit my lip and balled my fists as I struggled with the intense frustration, humiliation, and fear rising within me.
“Second, your bedtime will be 7:30 sharp. Any bad behavior during the day and I’ll move it up to 7, or even earlier. That means you will be in your crib, diapered and locked in with the lights out by bedtime. Any whining or complaining will result in trip over my lap.”
My mouth hung open again and my lips quivered as I tried to deal with what she was telling me.
“Third, I’ve already told you that you are to do whatever I tell you without question. That goes for Jordan here too. She has equal authority over you and if she feels you need a spanking, she has every right to do it.”
As I stood there in shock, Jordan strode over to the dresser and reached over to pick up the Spencer paddle.
“And just to get things off on the right foot so you’ll see who’s boss around here, I’m going to give you a taste of how things are going to be from now on,” Jordan told me.
I couldn’t believe what was happening to me. The very woman I resented and hated and had stolen my girlfriend was about to pull my diapers down and spank me!
I gulped in panic and felt a fear-induced stream of pee flood into my already soggy diapers.
“No-p-please,” I begged her as I put my hands up in protest.
She snatched my wrist roughly and yanked me over as she took a seat on a sturdy stool that I assumed served one purpose only–one in which I was about to participate in. With grim determination, she tugged my plastic panties and heavy wet diapers down with one quick move, leaving my pink chastity device fully on display.
I blushed hot red with shame as the strong smell of pee surrounded us.
“Pathetic…absolutely pathetic,” she said shaking her pretty head, “And I can see why Denise locked up this tiny little thing. A sissy like you doesn’t deserve to be able to cum anyway.”
Looking back up into my fear-filled eyes, she fixed me with a stern gaze.
“I’ve been wanting to paddle you for a long time now, Chrissey,” she told me, “so you can be sure I’ll make this one count.”
“Please don’t spank me!” I begged her shamelessly, the panic rising uncontrollably and making my knees weak.
“Get over my lap,” she told me tersely.
I squealed like a little girl as she yanked me over her skirted thighs, causing me to fall face forward helplessly.
“Wait! Please–please don’t spank me,” I sobbed. I knew there was no escaping now and as usual, my weak nature had put me in a place where I was going to receive a painful, humiliating punishment at the hands of the very person who was my arch enemy.
“By the way…I just thought you should know…” Jordan said smugly as she rubbed the fearsome paddle against my damp bottom, “Everyone at work knew you were wearing diapers–you smelled like baby powder and pee all the time and the girls used to call you ‘Pamper Princess’.”
I groaned with crushing shame at the realization even as I squirmed feebly on Jordan’s lap.
I opened my mouth to say something but I was cut off by the harsh, biting impact of the hard wooden paddle being seared across both my tender cheeks. I gasped in pain and howled as the paddle came down again and again in quick, scalding succession. Jordan was letting loose with months of pent-up frustration and resentment and she spanked me with all her strength. I burst into tears immediately and kicked my feet as I bunched my fists and beat the floor.
My wet diapers had only served to make my bottom more sensitive and I bawled with bitter indignation as each hard slap of the paddle impacted my damp, pee-soaked buns.
With tears flooding my eyes, I could no longer see Denise clearly as she stood above me, but her hands were on her hips as she watched her lover soundly paddle me with impunity. It felt like a thousand wasps were stinging my blazing cheeks and I was crying like a baby, struggling to escape Jordan’s terrible retribution but her grip was like steel as she continued my excruciating punishment.
Denise must have taught her well because after bringing the center of my buns to a flaming hot, cherry red, she turned her attention to the virgin sides, slapping them harshly until they glowed equally to an angry, red crimson. I prayed that she was done but then she returned to the center of my seat, repeatedly bringing the paddle down hard, delivering deep, vengeful swats right at the soft curve of my bottom where it reached my thighs. I wailed at the top of my lungs, kicking wildly as the hot tears spilled off my face to splatter on the floor while I pounded it with my fists in bitter, impotent frustration.
Was this to be my fate? Being paddled like a naughty little boy whenever the mood struck them?
While I had some sort of relationship with Denise (the exact nature of which I was still unsure), I could tell Jordan wouldn’t think twice about putting me over her lap for the slightest infraction.
I had resented Jordan from day one and it was the worst possible fate for me to find myself under her harsh and unforgiving authority. And now–to be spanked by her! It was more than I could bear.
At last, the terrible spanking was over and Jordan dumped me unceremoniously on the floor. I immediately reached around and rubbed my flaming, swollen cheeks as I cried like a baby before them.
“That was only the first of many spankings you can expect from me, sissy boy,” she informed me.
Denise came over and bent down to my level, smiling warmly at me in sharp contrast to Jordan.
“Aww baby,” she said, her voice for once revealing her sympathy, “Come here, sugarplum.”
Scooping me into her arms, I sobbed miserably as she held me to her soft, pillowy bosom in a tender, motherly embrace.
“I’m sorry that was necessary but it was important for you to learn that Jordan means business when she tells you what to do,” she said in a voice for simple toddlers.
I wiped my arm across my wet face and looked over to Jordan who still had the paddle in her hand, her arms crossed over her chest defiantly and an unrelenting, smug look on her face. As much as I hated and begrudged her, she was my boss now and I was going to have to respect her rule over me.
Whereas before, I had been an insignificant worm to her–now, I was her bedwetting sissy baby for her to punish and humiliate as she pleased.
Denise was soothing me and rubbing my head in a maternal way as she pushed my wet nose between her mammoth breasts.
“Poor little sweetums,” she cooed, “Mommy needs to put her little baby back into her diapers.”
I wasn’t about to resist her. I had no strength left.
Choking back a sob, I let her take me over to the changing table where she laid out three thick cloth diapers. I certainly didn’t want to live the life of a little baby girl but these two gave me no choice.
I pouted and continued to cry as she sat me down on the diapers but I howled out as soon as my blazing bottom came into contact with them.
Denise smiled down on me again and she pushed a big, pink rubber pacifier between my quivering lips to quiet me. I found it oddly comforting and I tried not to look at Jordan who was still standing there looking superior, staring down at me with disapproval. I whimpered as Denise pinned me into my new, permanent underwear; thick, embarrassing diapers, and I tried not to think of how it would be like to be seen by everyone that came over.
“Time for your baby panties, Chrissey!” she said gleefully as she positioned a pair of pink nursery print waterproof panties at my Mary Jane-clad feet. I sniffled as she worked them up my smooth legs and worked them over the bulky cloth, running her fingers around the waistband to be sure all the cloth was contained inside.
Rising up, she went over to the closet and came back with a fluffy pink and white baby dress which she held before me proudly.
“Is this what my little girl wants, hm?” she asked in her syrupy voice.
With the fat pacifier stuffed in my mouth, I nodded submissively.
“Well, don’t you worry sugarplum, ’cause Mommy bought a whole wardrobe for you, and you’re going to be just the cutest little baby girl from now on,” she said enthusiastically as she removed my fleece top and replaced it with the frilly dress.
Standing me up, she stood behind me as she zipped up the back and adjusted the short hem of the girly ensemble which barely covered the top of my diapers. I cringed as I stared at our reflection in the mirror, looking like mother and baby daughter.
Even without her heels, Denise was much taller than I but with her stilettos on, she practically towered over me. She stood behind me proudly, beaming with pleasure at the final result of all her careful scheming and planning.
“From the first day I met you, I knew I had to make you my baby girl,” she said with her beautiful smile, “And we both know this is where you really belong, Chrissey–not trying to impersonate a man, but wearing dresses and diapers in your very own nursery like the big sissy we all know you are.”
I blushed hotly from behind the fat pacifier filling my mouth at her humiliating words.
Jordan stepped forward and stood next to Denise.
“I think we should invite the girls from the bank so they can see the diapered sissy that used to work with them.”
“Oh my god–what a great idea!” Denise agreed, clapping her hands with eagerness, “I can’t wait to tell Ashley and see the look on her face when she sees him.”
Turning around to face Jordan, Denise threw her arms around her neck and planted a big, passion-filled kiss on her lips.
As I watched the two of them groping each other lustfully, I seethed with mute jealousy and envy.
Breaking her kiss momentarily, Denise looked into Jordan’s willing eyes but kept her arms around her.
“I think we need to leave our baby to play with her toys while we have some fun of our own,” she suggested in a husky voice.
“I thought you’d never ask,” Jordan grinned.
The two left me standing there, locking the door behind them to prevent me from leaving or interfering with their lovemaking.
I sniffled and sighed heavily, sitting down to look at the dollies and toys that had been gotten for me.
Several minutes later, the rhythmic sounds of the two of them moaning could be distinctly heard from the adjoining room as I stacked my colorful building blocks.
I didn’t even notice as I began wetting my soft, fluffy diapers.
…six months later
Anxiously, and with rising concern, I sat on the padded, vinyl covered floor of my playpen, surrounded by a collection of my dollies and a number of big plastic building blocks.
Not surprisingly, my diapers were soaking wet, as they often were these days. I had long ago lost my ability to control my wetting, and it was rare that I even got any kind of a warning sensation beforehand. More often, I just found myself helplessly wetting my diapers like any completely incontinent toddler.
Denise had explained to me that during the first few days after I’d met her, she’d put a mild sedative and diuretic in my baby bottle, just to get the process started, but after that, it had all been me. I think all the pressure I had been under, both at the bank, and trying to deal with Denise during the early stages of our relationship had caused me to revert to bedwetting, which in turn, started my uncontrolled wetting during the day. In any event, my diapers were indispensable now and they normally only remained dry for the first hour or so. After that, it was only a matter of time before they grew heavy and began to sag with all the pee accumulated from several consecutive wettings.
I had certainly become used to the feeling of wet diapers on a regular basis and it no longer bothered me like it used to. And to be sure, I had gotten used to the smell of stale, pee-soaked diapers in my nursery which no amount of fragrance could cover. Any visitors that should happen to come in, quickly realized that my diapers weren’t just for show but we’re absolutely necessary to keep my childish wetting under control.
True to her word, Denise spared me no dignity around her friends.
By now, they all knew of the sissy baby in her house and I was regularly paraded in front of them wearing my short dresses, onesies, or diaper shirts. And if she felt it was time, my diaper changes would take place in front of any or all of them, with some of them even lending a hand during the process.
And even though this was happening on a regular basis, the intense humiliation I suffered was as if each one, was the first time. Some of her friends really enjoyed teasing me, especially Ashley who was a regular visitor, or her bossy but sexy friend, Ariel. The latter particularly enjoyed humiliating me and making me explain in great detail why I “wasn’t ready for big boy underpants”, and why diapers would be my constant companion.
I had hoped my spankings, which had become a regular event since I moved in, would be kept private but that too, was something I had to suffer in front of everyone. Here again, Ashley and Ariel were only too happy to lend a hand and it was to my utter shame whenever one of them would unpin my diapers and pull me over their lap to soundly paddle my bottom.
But overall, I couldn’t really complain. My room and board were provided for by Denise and Jordan and I had zero responsibilities. My main concerns centered around what kind of food I was served in my high chair, and how soon I could get my perpetually wet diapers changed. To my frustration, it wasn’t uncommon for Denise to squeeze the thick seat of my diapers and dismissively tell me “you can wait another hour”, which meant enduring the annoying, clammy wet embrace for who knew how long.
I spent most of my time in my nursery, which on the whole, was about as dull and boring as it could get. And even when I was let out, it was usually just to be strapped into my high chair for meals or be placed in the playpen so they could keep an eye on me.
I had traded the stress of living in a competitive world for my freedom.
Denise kept my schedule of orgasms rare so the spikes in my chastity device remained as a constant source of pain for me. I tried my best to avoid thinking about sex but it wasn’t easy with the two of them going around the house wearing little in the way of clothing. I was generally allowed but one orgasm a month, and that, only by being bent over the crib mattress, my diapers pulled down as Denise pounded me for an hour from behind with her big, hard cock. Jordan made a point of telling me I was lucky to get even that, and maybe she was right, although it always left my hole sore, aching, and leaking of her gooey semen.
My sex life could be varied, in that sometimes Denise allowed me to masturbate into my diapers instead of being humped for my monthly orgasm. However, those rare instances always occurred under the most humiliating circumstances, like when she made me do it front of all her friends. After removing my chastity device, I was re-diapered and made to sit in the middle of the living room floor, then given a set time limit in which to rub myself to orgasm.
Given the audience I was to perform in front of, I preferred being bent over the crib mattress to the mortifying humiliation of playing with myself in front of a bunch of jeering, mocking women.
It was Jordan’s idea that I should receive regular “maintenance spankings” once a week, just to make sure I remembered who was boss. I certainly didn’t need any reminding and I dreaded them terribly but like everything else, I had absolutely no say.
On Sundays, either Jordan or Denise would come into my nursery, take down the paddle and put me over their lap for a blistering spanking that left me kicking and crying like a baby.
The only plus out of that arrangement was when Denise was the one administering the punishment. She would often re-diaper me afterwards and place me on her lap, allowing me to nuzzle her big, beautiful breasts as she bottle fed me.
Another aspect of my new life that I soon discovered after moving in were regular, daily enemas. Denise had a big dildo nozzle she liked to use when she bent me over for my daily purging, and it made her giggle to watch me squirm and whimper as I took in the quart or more of hot, soapy water deep into my rectum. She said she loved nothing more than to see me weak and helpless, bent over her lap with my legs spread as she administered the enema and I moaned like a little girl.
As much as I hated that humiliating procedure, I was wishing now that I had gotten one earlier today. The weekend morning had been unusually busy for the two of them and Denise had simply forgotten all about it. While one would think that would be a good thing, two circumstances were now dictating otherwise.
The first, was that I was starting to feel warning cramps and an urgent need to go. The second, was that Jordan had put my big rubber pacifier in my mouth with strict instructions not to remove it.
I knew better than to disobey her when she had issued that kind of order. My bottom was still sore from last night’s severe paddling.
But at the moment, I was sitting in my playpen in the living room, while the two of them were on the couch opposite me, kissing and fondling each other. Even under the best of times, this was a tortuous situation for me. It was agony watching or listening as they became amorous with each other because my little penis couldn’t help but get aroused and it wasn’t long before I felt the cruel bite of the sharp spikes in my chastity device. No amount of thinking about mundane things would alleviate the pain and I was left to suffer in silence.
However, today I had a whole new set of concerns. My dinner last night had worked its way through my bowels and was now seeking escape in the only way it could. I was shifting my position in the playpen but I knew there was no escaping nature’s inevitable course.
Rising up on my knees, I gripped the softly padded sides of the playpen and looked over anxiously at Denise and Jordan. They were completely oblivious of the torture I was undergoing as they kissed and explored each other’s bodies freely.
As the urges became stronger and stronger, I chewed my pacifier and whimpered, trying to get their attention. I knew that neither of them were fans of messy diapers and I could only imagine the punishment that would await me if I were to go right now.
Nevertheless, I was getting closer and closer to surrendering and I fidgeted anxiously, trying to find a position that would take some of the pressure off.
I gripped the side of the playpen until my knuckles grew white, mewling and desperately trying to make them look my way.
Finally, I couldn’t take it anymore.
With a sob of defeat, I knelt down a bit and relaxed. A huge, solid load pushed out between my spreading cheeks into my waiting diapers, oozing slowly, only to be followed by another equally thick one. A tear of shame trickled down my cheek and I was shocked at how big the mess was as the big slippery log slid up my crack. It filled my entire seat and felt heavier than I expected. I groaned as a third, smaller load joined the first mess in a growing, nasty pile within my diaper.
My face was red already from my exertions but now the utter shame of my childish act hit me. Even though I was still positioned on my knees, there was no escaping the warm, sticky mess being held closely and intimately against my bottom cheeks. And worse yet, my knees were getting tired, with neither Denise or Jordan showed any signs of noticing my distress.
At last, my knees couldn’t take anymore. With a sob of humiliation, I slowly sat down, the gooey mess squishing against my seat and spreading all around. I had never felt more like a helpless baby in all my life and I sniffled with shame, fighting back the tears that threatened to burst from my eyes.
At that moment, I hated being Denise’s little sissy baby!
I was sitting there miserably, trying to think of how things could be any worse for me when the doorbell rang. I gasped in shock and felt a strong stream of warm pee join the big, babyish mess that was already in my diapers.
Jordan stopped kissing Denise momentarily and she gave me a wicked look.
“That must be Chrissey’s babysitter,” she explained.
The very last thing I wanted was to have my mess discovered, let alone, by an outsider.
Jordan scurried over and opened the front door, standing aside as she invited her guest in. I winced as a tall, good looking, muscle-bound man entered. He was wearing snug white shorts and a tank top which served to showcase his very impressive physique.
Jordan gave the tall man a quick hug and then brought him over to the playpen. I blushed hotly as I looked up in embarrassment at the big man that was towering over me.
“Chrissey, meet my friend Hank. He’s a personal trainer down at our gym and he’s been super anxious to come over and meet you. I told him you were just a big sissy who wears diapers and dresses but he didn’t seem to mind.”
His crotch was eye level to me and I couldn’t help but notice a growing bulge in his shorts. I squirmed nervously in my seat, which only spread the big, sticky mess in my diapers further.
“Hank said he’d gladly babysit you for free, although god only knows why,” Jordan said sourly.
He looked down at me with naked lust in his eyes and I swallowed hard, watching as he slowly stroked his big, growing boner idly through the thin fabric of his shorts.
“Oh–” Jordan said by way of an afterthought, “–Did I mention that he’s gay? I’m sure the two of you will have lots of fun together.”