Surprise!

[Baby Bobby]

Surprise!

Chapter One


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 coc-ktail 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.
"What's wrong?"
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 c-um 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 pen-is 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 coc-k?" 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 pen-is 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 coc-ktail 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 pen-is 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, coc-k-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 pen-is, 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.

"OWW-WOW-OWW!!!"

SMACKKKK!!!

 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.

SMACKKK!! SMACKKKK!!

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 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 circ-umstances.

"And now, it's time my little sugarplum took care of mommy," she said with a coy smile.

[Baby Bobby]

Chapter Two


"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 pen-is 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 coc-k 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 coc-k 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...thats it...thaaaat's it...suc-k 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 suc-k her titanic phallus.

"This is right where you belong, on your knees with a big hard coc-k in your mouth..."
She paused only long enough to moan deleriously.
"Oh yessss...That's it...show mommy what a good little coc-ksuc-ker you are..."
I couldn't believe what I was doing. Was I really suc-king my supervisor's coc-k right now? On my knees, giving my hot boss a sloppy blowjob?
My lips were wrapped around the slippery shaft of her big, thick coc-k 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 coc-ksuc-ker 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 c-um, 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 coc-k meat stuffed into my mouth, I was in no position to respond.
Some of her prec-um was leaking as I suc-ked 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 coc-k was positioned just inside my mouth, with my lips wrapped around the big, bulbous head.

"OHHHHH!!! OH MY GODDD!!!" she shrieked.

I felt her coc-k 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 c-um as she thrust her hard coc-k 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 c-um in your mouth for months now," she confessed between gasps for breath.

I blushed with humiliation at having willingly suc-ked a coc-k 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 c-um and the inside of my mouth was slick with her semen. Blushing furiously, I swiped my arm across my face even even as I subconsciously licked the c-um 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 coc-k in your mouth--and we both know that's where you really belong.
"With that tiny little pen-is of yours, you're useless as a man, but as a coc-ksuc-king 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, suc-k 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 suc-kled, 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."

[Baby Bobby]

Chapter Three

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 suc-kling 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 pen-is, 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 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.
"suc-k 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 circ-umstances, 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 pen-is came into view and she suddenly giggled to herself.
"And how's Chrissey's little pee-pee doing today?" she asked in a 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 suc-ked 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 pen-is 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 suc-king 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 pen-is 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.

[Baby Bobby]

Chapter Four


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 c-um in three 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 coc-k 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 suc-king coc-k--"
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-fuc-ked me, shoving her fat coc-k deep into my mouth and grinding her pelvis against my face.

"Use that tongue again, Chrissey...oh...that's it...yes, that's better...suc-k it good...ohhh...that's my little sissy...thaaaat's Mommy's little boy...suc-k that sweet coc-k...mmm...yes..."

Her big balls were slapping my chin as the fat end of her coc-k pounded urgently against the back of my throat.

"Ohhhh...what a good little coc-ksuc-ker 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, suc-king 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 coc-k 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 coc-k out long enough to fill my mouth with one last good load before pulling it out entirely.

A white strand of c-um followed the blunt tip of her coc-k from my mouth and I gasped for air.
"Oh, that felt so good," she said as she held her still hard coc-k in her hand, moving it left and right and smearing the last bit of c-um 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 pen-is?" I asked her, "I haven't been able to c-um 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 c-um. My imagination, deprived of an orgasm for so long, began working in overdrive, thinking of all the delicious ways I could c-um...would she be returning the favor of oral sex for me? Maybe she would let me rub my pen-is 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 c-um with her. How many other guys would have willingly paid to be in my shoes?

[Baby Bobby]

Chapter Five




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 pen-is 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.

"Mr. Jones!"

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 restaraunt. 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.

[Baby Bobby]

Chapter Six



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 pen-is, 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 pen-is 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 c-um, and this one promised to be an earth shattering climax.

As she continued to fondle my diminutive pen-is, 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 pen-is 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.

SMACKKKK!!!

I howled in pain and tried to wrest my legs free but she held me too strongly.

SMACKKKK!!! SMACKKKK!!!

I cried out at the top of my lungs as she continued to swat my damp, bare cheeks mercilessly.

SMACKKKK!!! SMACKKKK!!!

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 pen-is, 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."

[Baby Bobby]

Chapter Seven


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 suc-k her big, thick coc-k 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 have 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 c-um 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 pen-is. One word from her, a button undone, or a soft caress from her hand caused my long deprived pen-is 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 pen-is 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.