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Kendra - Chapter Two

A year later, when Mike got a job at Johnson Technologies, he was floored when he first met his new boss.

Kendra Casanova was a stunning brunette, with big, round breasts that she wasn’t afraid to hide behind loose, ill-fitting clothing. Poor Mike was so intimidated by her, that he could hardly string a few words together in a complete sentence without sounding like a stuttering fool. He also just barely managed to avoid wetting his pants. It certainly wasn’t made easier by the fact that she towered over his unimpressive 5’ 2” frame. Kendra made a point of wearing her “power heels” to work, and on the odd occasion that Mike was in a conversation with her, he was forced to crane his head upwards to make eye contact, like a child addressing an adult. This inevitably meant looking up over the tops of her big breasts, which she thrust out proudly before her within her snug, low-cut tops. Mike’s mouth would go dry, and he would gape up at her gorgeous face like an idiot.

Although he did everything possible to ingratiate himself with his manager, Kendra remained aloof and uninterested. Indeed, with her youthful beauty and the body of a goddess, she had no lack of boyfriends, all of whom easily outclassed Mike in every way. It was with acute jealousy that he watched them pick her up after work, whisking her away on yet another hot date. He could only imagine what it must be like to be a guy who could have his way with Kendra. The prospect made him shiver with arousal and envy.

Sadly, there would be no such dates for Mike. For one, he knew he could never bring a woman home, not with the pungent smell of pee from his diapers constantly filling the apartment. But perhaps more damning, was the laughably small size of his penis. Even when he was horny and as stiff as it could be, it barely reached four inches, and that was being overly generous. Of course, when it was in its normal state, it was hardly an inch in length and it more closely resembled a toddler’s penis than that of a man. Perhaps it was due to his constant, daily masturbating in his diapers that prevented it from growing to a normal size but as a result, it remained ridiculously small.

The one time he’d managed to make out with a girl in high school, she’d laughed out loud when she discovered his child-like nub and the date had been abruptly terminated.

Back when he was living under his mom’s roof, it was a different situation. Mike had enjoyed nothing better than masturbating himself silly after he’d been pinned into his fluffy nighttime diapers and put to bed. This had resulted in several late-night spankings when his mom had caught him, but he simply couldn’t stop himself. The fact was, his thick cloth diapers were incredibly soft, and the multiple layers caressed his little child-sized member in the most erotically torturous way. Of course, it was mortifying that the teenager had to wear them in the first place, but once his mom pulled his babyish plastic panties up and over his triple-thick nighttime diapers, he secretly let out a sigh of contentment. The moment she tucked him into bed and closed the door to his bedroom, he would frantically rub himself to an eye-crossing orgasm. It was in such a restful state of bliss that he would slowly drift off to sleep and soon begin wetting his diapers, thoroughly soaking them like the sissy bedwetter that he was.

And of course, now that he was once again wearing them in his apartment, he delighted in changing early for bed and playing with himself as he fantasized about his beautiful boss, Kendra, and her fabulous, sexy body.

After he'd climaxed, he was filled with shameful feelings of guilt, but his pragmatic side acknowledged sadly, just how much he needed to keep the diapers on for bedtime.

Perhaps it was his constant, daily masturbating that also led him to have so little control over his staying power. He would scarcely rub himself for two minutes before he felt himself erupting in his diapers, splashing the tiny little load of semen into his soft, fluffy diapers.

Things continued on in this manner until one day, when Mike received news that a distant uncle had passed away unexpectedly, leaving him a sizable inheritance. This was exciting news for the nearly destitute young man, and he could barely stop himself from bragging about it to Kendra, the next time he saw her in the break room at work. Hoping the money would finally make a difference to her, he was pleasantly surprised when she actually deigned to make conversation with him.

Holding her coffee cup in her perfectly manicured hands, Mike practically trembled before her and he was once more reminded of what a superior female she was. His mouth suddenly went dry again as he looked up into her dark, beautiful eyes. He found himself stammering, clumsily trying to fashion a coherent conversation with this exquisite woman, so vastly far above his social station.

But it was after that initial episode that Kendra actually started to acknowledge Mike, greeting him in the hallway or waving goodbye to him on her way out of the office. He tried to tell himself that the money (and there was a lot of it) wasn’t the only reason she paid any attention to him. Instead, he told himself that it was his modestly attractive looks and humble personality that she found engaging.

One time, he had gotten into the elevator at work to find her already in it, coming up from a lower floor. He stood, facing away from her, staring at the polished aluminum doors before him and his heart pounded in his chest, knowing that only eighteen inches behind him, stood his babe of a boss. Dirty, perverted thoughts filled his head, and his little penis twitched anxiously as they rode the short ways up to the eighth floor.

As he stepped out of the elevator, he suddenly felt his bottom being pinched and he gasped with surprise. Looking back, he saw Kendra wink at him playfully, before strutting away sexily to her office.

Mike was practically floating on air as he made his way back to his cubicle in a daze.

Nothing much happened for the next week until a company function came up and Kendra’s date unexpectedly canceled at the last minute. Stopping by Mike’s cubicle, she asked him if he would be willing to fill in.

Mike gulped hard and stammered out a reply, indicating he would be delighted to join her, and he sped home after work to get ready. Rushing back in his best shirt and slacks, he couldn’t believe his luck in having landed a date with Kendra. A million possibilities went through his head, and he barely stopped himself from masturbating before heading out to go meet her.

*********************************************************

Kendra wasn’t sure when it was that she first became aware of Mike as a person. It was probably a month before, that she had needed to call him into her office to address some deficiency in his work. Although it had been a minor affair, the young man standing before her looked like a scared little boy, and she had a random thought that he might wet himself before her.

It was several months later, that the shy employee initiated a conversation with her, bragging about a huge windfall of money he’d inherited. Clearly, he thought he could make a big impression on her and while under any other circumstances, she would have ignored the runt, for some reason, she found herself starting to contemplate the two of them together.

All things being equal, Kendra preferred a tall man, muscular in stature, and manly in his bearing. That was what she was used to, and that’s who she normally dated. Mike was anything but that. With his short height and delicate frame, he looked weak and a little effeminate, although his baby blue eyes did give him an almost child-like cuteness.

Kendra knew instinctively that with his eager-to-please personality, there was little that he wouldn’t do for her, if she were only to ask. She had recognized his type all throughout high school and college—shy little wimps that fantasized about being with a woman like her but in reality, had no chance whatsoever.

Slowly, ideas began to form in her head of how a relationship with him might develop. These were ideas that she’d never consider with her traditional boyfriends, but things that just seemed more appropriate for a shy little boy type like Mike.

The idea of controlling Mike like a lost puppy started beginning to appeal to Kendra’s darker side, and she found herself thinking more and more about the things she would do to him. It was after a second disciplinary incident—this time for an oversight on his part, that the random idea popped into her head of putting him over her firm lap and spanking him like a child. Kendra could easily imagine his lily white bottom being flattened repeatedly by her wooden paddle and quickly turning it to a flaming red as he helplessly kicked his feet and cried like a baby. She knew that not only did she have the superior strength to make it happen but also the force of character.

In addition, she began pondering the idea that it would be fun to somehow control his sexuality. She knew very little about chastity devices but after doing some research on her computer at work, she soon discovered that there were a vast array of choices for weak males that needed controlling.

One day, the company was having a function after work and Kendra’s current boyfriend called at the last minute to tell her he’d be unable to take her to the event. This was disappointing, as Kendra loved the mind-blowing sex she had with the hunky guy, but it wasn’t the end of the world.

For a minute, Kendra contemplated calling one of her other studs and then she stopped herself. Maybe this was fate telling her to reach out to Mike, the little geek down in data analysis.

While she could have easily just picked up the phone and reached him via the company intercom, she decided to physically go down to the eighth floor and see him in person. Part of her wanted to see how he’d react, and she was looking forward to making him blush and squirm under her intimidating presence.

After unbuttoning one more button down the front of her tightly-fitted top, she sauntered over to Mike’s cubicle. As he caught sight of her, his mouth opened like a drawbridge and his eyes widened in amazement. Bending over slightly, Kendra treated Mike to a jaw-dropping view of her impressive cleavage and big breasts as she explained her need for a date to the company event.

In response, Mike couldn’t babble his acquiescence quickly enough and he spilled his cup of tea in the middle of his clumsy reply.

The night went well enough, and Kendra found Mike’s adoration and shyness endearing. Of course, nothing happened, sexually speaking, although Kendra gave him a peck on the cheek when they said goodbye for the evening.

It was a month later, and Mike was beginning to think he’d never hear from Kendra again when she asked him out on a more formal date.

It was afterwards that she suggested they go over to his place for another drink when he balked and tried to make an excuse to prevent her from coming over. Stammering like a fool, he babbled that his place was messy and he didn’t want her to see it but Kendra, an astute judge of human behavior, could tell something wasn’t ringing true about his explanation. They parted company with an awkward tenseness and Mike berated himself for the next week.

Later on, thinking he could somehow make it up to her, he had a modest bouquet of flowers delivered to her office, accompanied by a desperate note of reconciliation. When she finally responded back, Mike was so excited that he pinned on his diapers as soon as he got home and masturbated furiously to an orgasm that made his head swim. All through the weekend, he stayed inside and continued to diddle himself, as visions of Kendra’s big, mouthwatering boobs filled his eager imagination. His favorite fantasy, was to imagine her breastfeeding him, as he lay his head on her lap and nursed hungrily from her mammoth boobs. Indeed, by Monday morning, his little limp penis was tired, red, and sore.

At last, on Wednesday afternoon, he got a text from Kendra, inviting him to stop by a nearby wine bar for a drink after work. Mike was overjoyed, although his choice of clothes that day was a bit nerdy and anything but impressive.

As soon as they got in Kendra’s car, she slid her hand over to his crotch and slowly began fondling him over his slacks. Mike gulped hard and a bead of sweat trickled down his brow. Unfortunately, between his nonstop masturbating, and the fear and intimidation he felt in the presence of his sexy boss, he just couldn’t get it up. Confused and a little frustrated, Kendra kept probing, trying to find his elusive package. Of course, this only had the effect of causing his shy little member to shrivel even further, like a frightened mouse.

“Are you…are you an eunuch?” Kendra asked incredulously.

Mike blushed a bright red and he swallowed hard.

“N-no, it’s just…I mean, it’s just that I, uh, have a kinda, um, small cock,” he confessed haltingly.

“Honey, that’s not a cock,” she said firmly in no uncertain terms, “Don’t ever use that word to describe what you have. No, a little dicklette that is that small is only deserving of the word ‘penis’.”

Pulling the car over to the side of the road, Kendra shut off the engine and turned to face Mike. His face was a blazing color of red all the way down his chest and he feared that she would tell him to get out of the car.

“I think you better show me what you’ve got,” she said firmly, as she fixed him with a steely look.

Mike gulped again and tried to stall her but Kendra just pushed his hands aside and began undoing his pants. In less than a minute, she’d unzipped his fly while Mike whimpered in protest, watching with fear and dread as she pulled his underwear away to expose his tiny little package.

Kendra began to smile and Mike felt a brief moment of relief until her smile became a grin and then she started laughing out loud. Looking back at his distraught face, she laughed and laughed, unable to stop herself. Mike felt tears of shame beginning to well up in his eyes and he started considering opening the door to run away from her.

“Oh honey,” Kendra said when she could finally control her laughter, “Don’t be sad—some little boys just never grow much down there. I think it’s cute as a button.”

Mike was hardly consoled by such an appraisal, and he bit his lip in angst. And he was hardly flattered by being compared to a little boy, although deep down, he knew his little bits did most closely resemble those of a child. Quickly zipping up his pants, he looked out the opposite window, crushed with humiliation.

“I think I wanna go home now,” he bleated, nearly in tears.

Kendra reached over and pulled him close, mashing his face against her big, soft breasts.

“Hey, I’m sorry sweetie, I didn’t mean to laugh,” she said placatingly, “Look—I think you’re very nice. Tell you what--if you’ll forgive me, I promise not to say another word about it. What do you think?”

Mike looked up into her pretty, glittering eyes and he was completely helpless.

“Um, okay, I guess,” he said barely audibly.

Kendra bent down and kissed him passionately and despite his crushing shame, he felt the first stirrings of a tiny erection.

**************************

All through the week, Mike lived in a state of anxious uncertainty, not knowing where he stood with Kendra. Finally, on the following Tuesday, the phone on his desk buzzed, and he picked it up to answer the inter-office line.

“Ms. Casanova would like to see you in her office,” Kendra’s assistant told him without preamble. Her tone of voice was curt and neutral, making Mike fear the worst.

“Did-did she say wh-what it was about?” he stuttered.

“I’m sure she will tell you herself,” she replied brusquely before hanging up the line.

Mike gulped back his fear, wondering what he could be getting disciplined about. He went over the work he had done in the last week, but he couldn’t think of anything that might have landed him in trouble.

On shaky legs, he made his way to the elevator and rode it up to the 14th floor where Kendra’s office was. As he came up to her assistant’s desk, the attractive woman vaguely waved her pen behind her.

“She’ll see you now,” she told him.

Mike swallowed hard and tugged at his shirt collar as he opened the door and cautiously entered his boss’s office. Kendra was on the phone, and she silently beckoned him to take a seat in the leather chair before her desk.

Mike took a moment to glance her way without wanting to look like he was checking her out, even though that’s exactly what he was doing. Today, she was wearing a slim, hip-hugging pencil skirt and a clinging, very low-cut sweater top.

She looked absolutely ravishing.

Despite himself, he couldn’t take his eyes off her perfectly round breasts and his mouth watered with desire.

At last, Kendra terminated the call and she smiled at Mike for the first time.

“Thank you for coming up,” she said as she rose to her feet, slowly coming around the front of the desk. In her five-inch pumps, Kendra was like an amazon goddess as she looked down at her flustered employee. Bending down, she suddenly planted a wet kiss on Mike’s cheek.

“I have a little something for you,” she said seductively.

Mike felt his little penis twitch and his heart skipped a beat.

“Y-you do?” he asked.

Picking up a small box with a FedEx label on it, she reached inside and pulled out a small, felt pouch.

“Yes I do, and I think it’s just what you need,” she said as she opened the pouch and dropped a small, stainless steel chastity device into the palm of her hand.

Mike swallowed hard in anxious fear as he stared at the contraption, instinctively pulling away as he grappled with what it was.

“Come on, stand up,” she said, her voice taking on a cutting firmness to it as she pulled him to his feet.

Reaching down, she pushed his hands aside and began unzipping his slacks.

“No wait—I don’t think…” he whimpered uncertainly, “I don’t wa-want that.”

“Mike, if there’s going to be any kind of future between us, this is going on and I’ll be the one to determine, when, and if it comes off.”

Mike felt like a bucket of cold water and just been dumped on him. He squealed in protest as she abruptly yanked his pants down, followed by his pee-stained underwear. Like his life was flashing before him, he suddenly realized the implications of this terrifying device. If he couldn’t escape from it, it spelled an end to his nightly masturbating and threatened to put an end to any future orgasms, however pathetic they were.

“Stop-please stop,” he cried plaintively but Kendra had already tugged his little package through the steel cuff ring and was deftly positioning the thimble-sized cage before his tiny, quivering head. She swatted his hands aside as she put the cage over it and mated the alignment pins with the holes on the ring, mashing his minuscule shaft within. With a quick insert of a long key, Kendra rotated it, locking the intimidating device in place.

“There—perfect. It's definitely just what you needed,” she smiled triumphantly.

Mike whimpered as he grasped the device and tried desperately to free himself.

He couldn’t imagine why she felt this was what he needed.

“I hope your last orgasm was a good one, because I’ve decided that your first period of lock-up will be three months,” she told him like she was delivering a death sentence.

“Three-three m-months?” he quaked nervously.

“Mm-hm,” she grinned, “That will allow you to get adjusted to a lifestyle free of orgasms and without being able to play with yourself. Trust me—you’ll thank me later,” she said as she dropped the key into her purse.

Mike stared back at her in disbelief.

“Your mommy should have done this a long time ago, but better late, than never,” she continued.

Mike sputtered and mumbled to himself, ashamed of his spineless subservience to this woman as he shifted his feet in place uncertainly. Kendra saw his distress and she hugged him tightly, pressing his face against her big, soft bosom comfortingly.

“There, there,” she said sweetly as she whispered in his ear, “You’ll be just fine, you’re my baby now and you have absolutely nothing to worry about.”

But Mike did worry.

He worried all that afternoon and on the way home from work. He kept squirming in his seat, trying to get comfortable with the strange new device that was locked implacably around his genitals, compressing his little shaft and making sure his penis had absolutely no chance of getting hard. As he made his way home, he tried to wrap his head around what it would be like, not being able to play with himself anymore. How was he going to manage?? He dearly loved masturbating in his diapers as soon as he got home, but now—Kendra had irrevocably taken that away from him.

Visions of her big, beautiful boobs and her pretty, smiling face filled his head and his tiny penis flexed madly within its cage. Not for the first time, did he reach down and try to get some relief but it was no use.

When he got home, he immediately rushed to his bedroom and pinned on his fluffiest set of diapers, nearly ripping the rubber panties in his rush to get changed. He sat on the edge of the bed and rubbed himself for all he was worth but it soon became apparent that it was hopeless. The act only made him hornier, and his eager little boy-sized penis throbbed with bitter frustration.

An anxious knot of unrequited arousal formed in the pit of his stomach and he tried unsuccessfully to think about something else. Anything but his gnawing, desperate need for an orgasm.

Mike didn’t understand Kendra’s actions, and he began formulating careful plans to beg for the key from her. He simply couldn’t go on without being able to masturbate and the idea of waiting three months to be able to cum was unthinkable.

On the other hand, of all the strangest things that had ever happened to him, it seemed that he was on the cusp of a fantastic, life-changing development. From the signs she was giving him, it appeared as if Kendra was actually planning on making Mike her boyfriend, an inconceivable notion only just the day before. He tried not to think about his bedwetting habit and how that might impact any relationship between them, going forward.

He’d cross that bridge when it came.

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