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The Babysitter
Tommy was seething with resentment.
His gorgeous wife of three years, Kaitlyn, was dropping him off at some strange woman’s house for an extended overnight visit so she could be free to spend a fabulous getaway with her hunky boyfriend, Brad. He hated that she was seeing other men and he knew for certain that they would be having wild sex the whole time. Tommy grit his teeth in frustration as she imagined his sexy wife, her long legs wrapped around another man’s waist as he plunged his big cock into her, making her moan with ecstatic pleasure. 
He certainly had never been able to do that to her with his little, crayon-sized penis.
Kaitlyn hadn’t told him much about this woman, other than she was supposed to be a specialist who worked with bedwetters, a personal habit Tommy was mortified to share with anyone else, let alone a complete stranger.
“I still don’t see why I have to see this person,” he whined bitterly as they pulled into the driveway of what appeared to be an otherwise ordinary house.
“For one reason, this woman has a lot of experience with sissies like you that are still wetting their beds and I’m sure she will be able to help you with your little problem. 
“And secondly, I need Brad’s amazing cock inside me again,” she said impatiently, “and this is an excellent excuse to have you out of my hair for a while.”
Tommy ground his teeth again, trying to muster the courage to stand up to his alluring but domineering wife. She had gone from having secret, torrid affairs behind his back, to openly cuckolding him now and he had been powerless to stop her. 
In his heart of hearts, he knew he had originally deceived her about his sexual abilities in the bedroom which were in fact, nonexistent. That, and he’d managed to hide from her, the fact that his little penis was no bigger than a AA battery, even when fully erect. The first time she’d seen it, she’d laughed out loud for several minutes and then gone on to dismissively suggest that his hand was a more appropriate receptacle than anywhere inside of her.
He still burned with shame at the memory.
Waiting on the front porch, Kaitlyn rang the doorbell.
“Stop slouching,” she chided him.
The door opened and a tall, stunning brunette stood before them, an imperious look on her face as she placed her hands on her curvy hips.
“You must be Kaitlyn and you,” she said with disdain, “must be Tommy.”
The latter withered under her intimidating, steely gaze and the effect was all the more pronounced as she practically towered over him in her high heels.
She was obviously a woman who was aware of her looks and standing before them in a snug, skin-tight blouse, she thrust out her big, round breasts proudly.
Stepping outside briefly, she snatched Tommy by the wrist and pulled him inside the threshold. Before he knew what was happening, she had picked up an oval-shaped wooden paddle from the table stand and brought it down with a loud, resounding CRACK! against his bottom.
“OWW!!” he cried out in shock and pain.
Kaitlyn grinned with satisfaction.
“Looks like you’ll be in good hands,” she said.
Directing herself to Tommy, the woman addressed him sternly;
“My name is Jana, little boy, and you will address me as ‘Miss Jana’ or ‘Ma’am’—got it?”
“Y-Yes Ma’am,” he quivered fearfully.
“I’ve dealt with plenty of sissy bedwetters in my time, so I know exactly what you need;” she told him firmly, “diapers and strict discipline.”
Tommy’s face flushed bright red with shame and his lower lip trembled in fear.
“Thank you so much for taking him on short notice,” Kaitlyn told her as if she were dropping her 3 year-old off at daycare.
“I’ll see you tomorrow evening,” the statuesque beauty said, closing the door as Kaitlyn got back in her car, her spirit now as light as a feather.
Turning back to Tommy, Jana looked him hard in the eye as she wagged her perfectly manicured finger at him like he were an errant child.
“Let’s get something straight—sissies like you that wet their beds belong in diapers—diapers and plastic panties. So that’s our very first order of business.”
Taking him by the hand she led him stumbling into her house, past the living room and down the hall.
“Wha-wait!” Tommy stammered, “I’m not gonna wear d-diapers—you’re crazy.”
She hauled him into a softly lit room that looked more like a baby’s nursery than a bedroom; it contained a large, oversized crib, a pink dresser and a mesh-sided playpen, as well as fuzzy stuffed animals and toys for toddlers. The room also had a strong odor about it, like stale pee, something Tommy was all too familiar with and his cheeks reddened in embarrassment that this was where she was taking him. 
His bedwetting had been off and on when he’d first met Kaitlyn, but since she started openly cuckolding him, it happened nearly every night now.
Without a word, she took a seat on the only chair in the room, swiftly unzipping his pants and yanking them down past his knees.
“Stop it! Stop it!” he cried, flailing his hands in a pathetic attempt to prevent her actions. Before he knew it, she had flung him over her lap face down, and he kicked as he felt her fingertip at the back waistband of his pee-stained underwear.
“Let me go!” he wailed in desperation as he felt them being pulled down, exposing his soft, quivering cheeks.
Just as the last word left his lips, Jana brought the hard wooden paddle down, making a blistering impact on his bare bottom. Tommy kicked wildly now in panic as he cried out at the top of his lungs.
In desperation, he tried to rise up but she easily held him in place with her free hand as her other wielded the wooden paddle. It seared a scarlet imprint across his tender cheeks, swiftly followed by another and another. Tommy waved his hands around helplessly and he immediately burst into tears. This was no erotic spanking but the real deal—a scalding punishment that was going to make it difficult for the weak pantywaist to sit down for several days. 
Who was this woman? he frantically asked himself as his bottom was quickly transformed into a five-alarm fire.
Tears were streaming down his face now and he bawled like a child. 
And yet, Jana showed no signs of stopping. She had a terrific swinging arm, from years spent on the tennis court and she used it to good advantage, swatting his lily soft cheeks fiercely again and again with her unforgiving paddle. It flattened his buns harshly and they danced miserably underneath the avenging instrument. Each cruel slap of the paddle reddened his swollen cheeks further as he cried like a baby.
She meant to teach this simpering sissy a lesson he wouldn’t soon forget and the first lesson was unquestioning obedience to her absolute authority.
At last, the terrible punishment was over, and Tommy lay across her lap, sobbing uncontrollably. Jana set the paddle down calmly, carefully replacing a stray strand of hair that had fallen out of place. 
Dipping her hand into a jar of Vaseline, she immediately stuffed a thick dollop into Tommy’s virgin back hole. This was followed by a large dildo enema nozzle which she coated thoroughly before positioning it at his shy back entrance.
“Spread your legs, sissy boy,” she said firmly.
Tommy submissively did as he was told and he was soon rewarded with the fat rubbery cock head of the nozzle being pushed insistently at his anus.
“No—please!” he sobbed, “It won’t fit!” he wailed.
With a determined push, Jana thrust it past his puckering sphincter, making him cry out in anguish and pain. The nozzle was very fat, and it stretched his tight passage to the absolute limit. She briefly allowed him to get acclimated to the monster cock before slowly pushing it in further.
“I know a sissy like you has little or no control, so while I expect you to wet your diapers like a child, I don’t want any number two accidents. I’m going to give you a nice, warm, soapy enema that’s going to clean you out, which is just what you need,” she told him.
Tommy moaned weakly as the titanic shaft was slowly pushed deeper and deeper into his rectum, until finally all nine inches of the rubbery invader were buried inside of him. He gasped audibly, feeling very emasculated as he tried to adjust to the feeling of his passage being stretched to capacity and the huge, thick cock filling him up.
Releasing the clip on the long hose leading to the bulging red rubber bag hanging on a stand, a strong torrent of warm, soapy water surged into Tommy’s defenseless bowels.
“Ohhhh!” he moaned helplessly.
“This is exactly where a bedwetting sissy like you belongs—while your wife is out getting satisfied by a real man, you’re bent over my lap, your legs spread, with a nice, fat dildo giving you the soapy enema you deserve,” Jana told him. 
Tommy whimpered in shame.
She knew precisely how long to keep the clip open before shutting it off and letting the soapy water settle into her captive. By working patiently, she could give him a much more thorough purging than he might otherwise be able to take. And she was going to ensure he got every drop that was coming to him.
“After this, I’m going to pin you into some nice, fluffy diapers,” she said eagerly, “Won’t that be nice?”
Tommy moaned weakly, unable to respond as he struggled to contend with the growing cramps in his belly.
“Because you really do need diapers,” she continued, “Wouldn’t you agree?”
Feeling totally defeated now and completely at her mercy, he murmured his agreement.
“Say it, sissy boy—say you belong in diapers and plastic panties.”
With his back passage stuffed with a big, fat rubbery cock, Tommy was in no position to argue.
“I-I belong in d-diapers and plastic p-panties,” he whimpered.
Jana smiled with satisfaction, having used her cell phone to capture his humiliating confession on video. There’s another clip that will be getting uploaded to my website, she told herself.
“Don’t you worry, sissykins, the only time your diapers will be coming off will be for another enema—which you’ll be getting tomorrow, or for diaper changes, or another good, hard spanking. I won’t hesitate to paddle you again so you’d better do as I tell you—without question, do you understand me?”
“Y-Yes, Ma’am,” he whimpered.
Tommy moaned again. His belly felt completely full and he struggled weakly to get up off her lap.
“Oh no, not yet, baby boy, not until you’ve taken every last drop,” she said as she held him down and patted his stinging red cheek consolingly. She smiled as she looked down at the thick rubber cock shaft buried inside him, his little hole stretched tight around it.
Tommy had to endure the treatment for another excruciating ten minutes until Jana was satisfied no more water was available.
“Alright little sissy baby, you can go release that,” she told him, “When you’re done, you can come back here and I’ll get you dressed for the day.”
Tommy felt so humiliated as he limped down the hall to the bathroom. Worse yet, was the expectation that when he returned, she would be pinning him into a set of daytime diapers, as if he were some incontinent toddler.
Finally, some twenty minutes later, he came sheepishly out of the bathroom to find Jana in the nursery, texting someone on her phone.
“Good,” she said putting the phone down, “Now that that is out of your system, it’s time we get you into your sissy diapers.”
Tommy made a valiant effort to stop her but his arguments were soon stifled by the large baby bottle of warm milk she put to his lips, forcing him to drink it while she undid the rest of his clothes. He was mortified when she took his other hand away that had been shyly hiding his tiny package. Jana smirked knowingly when she held it in her creamy hands, her gaze admiring the secure steel chastity device that prevented Tommy from any sort of erections or masturbation.
“This is exactly what you need, isn’t it?” she goaded him, “I’ll bet a sissy bedwetter like you used to play with himself all the time, am I right?”
Tommy blushed with shame, in large part because she had painted such an accurate picture of him. Truth was, he used to masturbate constantly, first in High School, when his mom would diaper him before bed, and then later in the first year of his marriage to Kaitlyn, before she had decided he needed permanent chastity.
“No,” he quickly lied, although it was obvious she could see right through him.
“The important thing, is that your little sissy stick is locked up for good now, so you can rub your soft diapers all you want and you won’t be able to cum,” she said as she sat him down on a thick stack of Birdseye cotton cloth that she’d laid upon a raised changing table covered with practical waterproof vinyl.
Tommy lamented just how true that was. Since his sexy wife had stopped allowing him any relief, he was constantly frustrated and horny, and completely unable to do anything about it. Trying to think of ways to circumvent the device and allow his tiny little penis the opportunity to cum were never far from his mind.
Needless to say, Jana’s big, curvy breasts were maddening to look at, stretching her top in the most exciting and erotic way. As Tommy’s gaze lingered on her busty profile, his little package twitched in a futile attempt to get hard, however, the stubborn steel cage kept him confined to a modest 3/4” in length.
With his back on the table, Jana grasped his ankles and lifted them over his head, exposing his red, swollen bottom. She had just dipped her free hand into the Desitin, when the front door opened and a quick knock followed.
“Hey Jana—you in here?” another female voice called out.
“Back in the nursery,” she replied, holding Tommy’s ankles all the tighter as he struggled to escape.
The sissy squealed with dismay, just as a young woman stepped into the room, a growing smile on her face as she looked down at the trapped pantywaist holding his baby bottle and getting his red bottom smeared with diaper rash cream.
Like Jana, she was very attractive, with long, flowing blonde hair and a slim figure.
“Did I come at a bad time?” she asked, although her tone of voice suggested she was perfectly happy to walk in on this degrading situation for Tommy.
“Oh, not at all. I’m just putting this bedwetting sissy into his daytime diapers,” she replied casually.
The woman burst out laughing and then she caught sight of Tommy’s little caged penis.
“No wonder you wear diapers,” she remarked as she shook her head, “that is one tiny shrimp dick.”
Tommy’s cheeks blushed hotly and he tried to respond but Jana pushed the rubber nipple of the bottle back in his mouth, cutting off whatever he had planned to say. The woman giggled at how docile he was and how easily Jana was able to control him.
“And it looks like this sissy got his bottom spanked,” she observed pointedly.
“Yep,” Jana quipped, “For some reason, he thought he was going to be able to get away without wearing diapers today.”
“Ha ha!” the woman laughed.
“Yeah, fat chance of that,” Jana agreed.
Tommy’s face was beet red as these two women basked in his intense humiliation.
Setting his legs down, Jana began sprinkling his front area with lots of baby powder.
“While sissykins here is getting pinned into his daytime diapers, his wife is with a real man, getting all the hard cock she can handle,” she explained to her friend.
The blonde giggled as she looked down on Tommy’s blushing face.
“Sorry baby boy,” she said in her most condescending voice, “It’s pampers for you today; diapers and rubber panties.”
Tommy kicked a little in mute frustration as Jana pulled the bunny soft cotton tightly around his hips and pinned it closed snugly. The cloth was much thicker than his usual bedtime diapers, with a prominent center section down the middle and the bulk of it forced his slim legs apart in a very baby-like manner.
Shaking out a pair of pink nursery print plastic panties, Jana worked them over his feet and up his smooth, hairless legs until she reached the bottom of his bulging diapers.
At the same time, Tommy was treated to a breathtaking view of his babysitter’s cleavage as her big breasts swung before him. Nevertheless, her sexy desirability only made his humiliating experience that much more acute.
“Up,” she ordered him tersely.
Tommy obediently did as he was told while Jana fitted the waterproof panties around the thick layers of Birdseye cotton with crisp, maternal precision.
“Such a big sissy,” she remarked as she shook her pretty head in disdain.
Tommy blushed in shame and he sucked all the harder on the big rubber nipple filling his mouth.
All his life, Tommy had been pushed around by beautiful women like Jana and he had never had the backbone to stand up to them. Today, was just one more example. But by far, this was the most humiliating experience of his entire life. As much as he wanted to defend himself, he shuddered at the thought of taking another trip over her lap again.
Removing his polo shirt, she swiftly replaced it with a frilly, ruffled confection, an adorable baby dress of pink, yellow, and white, with a large Peter Pan collar and short, puffy sleeves.
“There, that’s much more suitable,” she said with satisfaction.
He had lost his shoes during his spanking so Jana removed his socks and replaced them with delicate, white lacy anklets. In moments, she was fitting a pair of glossy pink Mary Janes on his feet to complete his look.
“Okay bedwetter boy, stand up and take a look at yourself,” she said as she took his hand and led him over to the closet with mirrored doors.
His bottom was still stinging and throbbing painfully inside his fat, fluffy diapers and he sniffled as he took in his humiliating, babyish reflection. The frilly dress did nothing to hide his shameful diapers since the hem barely came below the elastic waistband of his plastic panties. 
Having his hand held like he were a child, Tommy felt like a toddler; the tall, very adult looking Jana next to him in her snug blouse, skirt, and sophisticated heels, and he in his baby dress and prominent diapers. And to make matters worse, her smug friend stood on his other side, snickering at his humiliating outfit.
“This is how you should be dressed all the time, like the big pantywaist that you are,” Jana told him, emphasizing her point with a hard swat to his fat, diapered bottom.
“Ow!” he whined and he pouted under her steely gaze.
“Alright sissy boy, time for your punishment assignment,” she said as she led him over to the mesh sided playpen, “Take the crayon and pad and write ‘I promise not to wet the bed’, two hundred times.”
Tommy frowned in dismay as he stepped awkwardly into the padded enclosure and sat down, wincing in pain as his sore bottom touched the soft vinyl covered floor of the playpen.
He started immediately working on his lines and the two women shook their head at his childish display before walking out of the nursery.
About a half hour later, Tommy was on his 65th line when he started shifting in his seat, trying desperately to find relief for his full, aching bladder. It had been all morning since he had last gone and all that milk was having a predictable effect on his system. Finally, he couldn’t hold out anymore and he called out to his babysitter.
“Um...Miss Jana?” he said as he gripped the padded rail of the playpen.
A few moments later, she came into the nursery, standing over him and crossing her arms over her big, curvy bosom.
“What is it, sissy boy?”
“I hafta go pee-pee, can I use the restroom please?”
“Nope. The bathroom is off limits to you,” she said with brusque finality, “Looks like you’re just going to have to wet your diapers, like you do every night,” she told him firmly.
Tommy blushed anew at her stern, condescending appraisal of him.
She was so strict!
Reaching down, she pushed a large pink pacifier into his trembling mouth and then, turning on her heel, she strode out of the nursery like a queen. 
Tommy shook his fists impotently, feeling more like a helpless baby than ever.
Finally, he couldn’t take it any longer and he whimpered as a torrent of hot pee flooded unstoppable into his soft, fluffy diapers. Gazing across the room, he sighed with frustration as he saw himself in the playpen, soaking his sissy pampers like an incontinent toddler. The pee kept coming, one strong wave after another but fortunately, between the thick cotton layers of Birdseye and his snug plastic panties, the deluge was contained. 
Finally, he finished and he was momentarily afraid to sit back down again for fear it would leak. Slowly, he waited for the pee to seep back into the absorbent seat of his diapers as he sucked feverishly on the rubber pacifier filling his mouth.
With a sob of shame, he slowly sat down in the playpen, the warm, sopping wet cloth squishing against his bottom. 
The humiliating smell of pee surrounded him as he resumed his work on his punishment lines, wondering idly what his wife was doing right now. He could easily imagine her, her top thrown aside in haste as she straddled her boyfriend’s body, rising up and down on his mighty shaft in just her push-up bra, as she moaned with delight. He could picture her, her boyfriend’s big cock thrusting deeply inside of her while Tommy’s little one was safely locked away in a steel chastity device. 
The thought of it made his tiny penis throb in angst inside its confining, restrictive prison. He took a moment to put his crayon down and rub frantically at the fat, cushiony front of his soggy diapers. They felt wonderfully soft and pillowy but his penis flexed impotently inside his cage.
It was so frustrating!
His wife was free to have as many orgasms as she wanted and here he was, confined to a baby’s playpen, wearing a soaking wet diaper and writing punishment lines with a crayon. To be sure, whatever shred of dignity he had before was gone for good now.
He had finally finished his hundredth line of ‘I promise not to wet the bed’, when he heard conversation coming from down the hallway.
“Is he in here?” a man’s deep voice was asking.
Tommy froze in fear and he felt a squirt of panic-induced pee add to the saturated cotton layers of his diaper.
Stepping through the doorway, a tall, muscular man with his shirt halfway unbuttoned stepped into the room. He beamed down on Tommy’s cringing, blushing form, looking him over lecherously as he casually stroked the front of his pants.
“Mmm, I love sissy bois,” he remarked as he slowly stepped over to the playpen. Jana was right behind him and her smirk said everything.
“This little sissy wets his bed, so I’ve got him in diapers while I babysit him,” she explained.
The man grinned as he undid his slacks and let them fall around his ankles. At Tommy’s eye level, the man’s monster cock bulged threateningly from inside his boxers.
“I haven’t cum for a week and my balls are aching for relief,” he said breathlessly, “Your sissy mouth is just what my cock needs.”
As he stepped closer to the rail of the playpen, his massive dong flopped out of his underwear and Tommy put his hands up in protest, the pacifier falling out of his mouth.
“N-No—wait! I-I’m not gay!” he cried.
“You’re a sissy, and all sissies love to suck cock,” the man said as he gripped the back of Tommy’s head and forcefully shoved his huge, stiffening member into the diapered pansy’s gaping mouth.
“MMMPHH!!” Tommy squealed as the huge man-meat stretched his jaws apart as far as they would go. His tongue tasted the warm flesh filling his mouth, and unconsciously, he ran it across the sensitive underside of the titanic shaft.
“Mm, that’s good, cocksucker, suck Daddy’s lollipop,” the man said in a husky voice.
He began thrusting it in as far as it would go until Tommy gagged before pulling it out a few inches, but always keeping the fat, mushroom-shaped head in his mouth. Tommy slurped and sucked, deeply ashamed to be degraded like this.
Jana had moved to the side of them, and she was taking pictures with her cell phone, chuckling to herself with each incriminating shot.
“I’m sending these to your wife right away—I’m sure she’ll be delighted to see her sissy bedwetter being put in his place by a real man.”
Tommy choked as the man rammed his enormous cock deep into his throat but with his head being held in firm, strong hands, he was totally at the man’s mercy.
His jaws were starting to ache from being stretched so far and he prayed desperately that the man would at least pull out before he came.
“Well sissy, I think you’ve found your true calling in life,” Jana remarked, “You could never satisfy a woman but your warm, wet, and willing mouth is going to make a lot of horny men happy.”
Tommy’s cheeks flushed with renewed shame as he sucked on the pulsing monster about to explode.
Just then, the man gasped abruptly and his eyes screwed shut as he blasted a thick, sticky load of semen into Tommy’s waiting mouth. The sissy squealed helplessly and tried to escape but the man had a vice-like grip around his head. He swallowed the gooey load, only to be rewarded with another one that threatened to drown him. The man shuddered as his big tool throbbed and spasmed, sending gobs of his man juice into Tommy’s eager mouth.
Jana was snapping more pictures as the diapered sissy struggled to cope with the firehose his lips were wrapped around. He swallowed again and again, the creamy spunk coating his tongue and throat with some dribbling out the side of his mouth. The man shoved it in farther just as he blasted yet another batch down Tommy’s larynx.
Finally, breathing hard, the man pulled his big, slick cock out of Tommy’s gaping mouth.
“Oh hell ya,” he said, his breath heaving as he recovered from his multiple orgasm.
Tommy’s cheeks flushed red and tears of shame misted in his eyes. He couldn’t believe he’d just sucked his first cock and swallowed load after load like a cheap whore.
“Your wife is happy to learn that you enjoy sucking cock so much,” Jana informed him with a grin, “And she says you’ll get plenty of opportunities with her boyfriend.”
Tommy grimaced at the thought of debasing himself again, even as he licked his lips of sticky semen.
Later on, lunch was served to Tommy while he sat, strapped securely in an oversized high chair. This was followed by another large bottle of warm milk, after which he finally got his soaking wet diapers changed. At 1 pm, Jana tucked him into the crib for his afternoon nap and predictability, he wet his diapers once more while he was sleeping. Fortunately, Jana didn’t spank him, but she did stuff a fat jelly buttplug inside him at changing time. Tommy was forced to suffer the emasculating feeling of fullness for the rest of the afternoon and early evening.
Dinner was more unappetizing baby food and another bottle of warm milk, after which Jana let Tommy play with some stuffed animals and blocks until bedtime at 7:30. By that time, Tommy had soaked his diapers again, so it was a trip to the nursery for a change before being tucked into the crib for the night.
Tommy was awakened the next morning as Jana squeezed the thick seat of his plastic-pantied bottom, feeling his pee-soaked diapers and shaking her head in dismay as she looked down upon the shame-faced sissy.
“You really are just a big baby, aren’t you?” she remarked with disdain.
She pushed another bottle of milk between his lips as she led him out of the crib and over to the changing table. After removing his soggy wet pampers, she sat down on the edge of the crib mattress and took Tommy over her lap for his morning enema. He knew better than to argue with her and this time, he obediently spread his legs to take in the mammoth dildo nozzle. What followed was a lengthy, humiliating, and uncomfortable process as Jana slowly emptied the nearly bursting red rubber bag of warm, soapy water deep into his bowels, all the while, lecturing him for his childish bedwetting habit.
It was a subdued, compliant sissy that came back into the nursery a half hour later, having released two quarts of sudsy water from his insides. He found Jana waiting for him, just as she was cinching up a tremendous strap-on dildo around her curvy hips. She had removed her skirt and the massive rubber shaft was strapped against the front of her lace panties.
Tommy quailed in panic and he almost wet himself right in front of her.
“It’s time for you to learn how to take cock like the big pantywaist that you are,” she said firmly as she forced him to his knees and bent him forward over the crib mattress. With his face now against the mattress sheet, he found himself surrounded with the shameful smell of stale pee.
“Please...please don’t,” he whimpered weakly as she kicked his feet apart, exposing his shy back hole again for her dark intentions. His tiny little caged penis hung beneath him, useless as ever. Kneeling behind him, Jana squeezed a tube of nursery Vaseline into his puckering anus and then she coated the fat head of her dildo.
“With your little sissy penis locked up, this is the only sex you’re ever going to get. Better get used to it,” she said with a harsh slap on his still-pink, right bottom cheek.
Feeling the huge latex cockhead pushing against his hole, Tommy squealed in fear and moved up against the crib mattress but there was no escaping her determined strap-on. She maneuvered it right where she wanted it and pushed firmly, popping it past Tommy’s defeated, trembling sphincter.
“OOHHHHH!” he cried in anguish as he slapped the top of the mattress.
Jana smiled as she gripped his pink buns, slowly pushing the veiny, fat dildo in and watching it sink deeper and deeper into Tommy’s rectum.
“There,” she said slowly as she grinned smugly from ear to ear, “There’s nothing like a nice, big cock to fill your pussy, is there?”
Tommy gasped with the feeling of fullness, even as his eyes crossed from the discomfort. He felt like he was literally being split in two. He grit his teeth helplessly even as another long moan escaped his lips.
With long, languid strokes, Jana slowly pulled the massive dildo out before plunging it back in, grinding it against him forcefully as Tommy’s legs flailed behind him, kicking in his futile attempt to escape. The fat girth of the rubber shaft was bigger than Tommy’s entire package put together and he cried and wheezed as his passage was stretched wide and forced to accommodate her monster cock. Fortunately for him, the shaft was well lubed and despite its incredible thickness, it slid in and out of his sissy pussy with ease.
Jana gripped Tommy’s hips firmly, as she plunged her lady cock deep into the squirming sissy, eliciting desperate moans and cries of helplessness. At the same time, the rubbery shaft was rubbing against his prostate gland in the most tantalizing way and Tommy couldn’t help but moan partly from the shameful but pleasurable feelings he was starting to get from deep inside his bowels.
Secretly, he had always had a thing for strong, sexy women, and even though Jana felt nothing but contempt for him, he couldn’t stop himself from lusting over her. Looking in the wall mirrors, he saw the intense look of determination on her pretty face and he watched in awe as her big breasts swung within her snug top with every mighty plunge of her strap-on.
She was simply amazing.
“This is exactly what your wife is getting this weekend,” Jana lectured him between penetrating thrusts, “Plenty of good, hard cock—something you can’t give her, can you?”
Tommy shook his head, knowing just how right she was.
“That’s why your little penis is locked up where it can’t get in any trouble...since the only thing you can do with it is to wet your diapers like a baby.”
Tommy blushed in shame as she rammed the dildo in hard, grinding it as far as it would go and making Tommy squeal like a little girl.
“Sissies like you need cock—not pussy,” she snapped, “Say it.”
Tommy gasped but he knew it was pointless to try and resist her.
“I-I need cock...n-not pussy,” he whined.
“And you’re going to thank Mommy’s boyfriend for satisfying her like only a real man can. When they come over tonight, you’re going to beg to suck his cock—do you understand me?”
Tommy squealed again helplessly as she shoved the big, greasy dildo in to the hilt, holding it there as she waited for him to answer.
“Y-Yes!” he cried, “I-I need to suck his cock,” he whimpered.
“And then you’re going to tell him that you’re nothing but a sissy bedwetter who belongs in diapers all the time, day and night,” she instructed him.
“Y-Yes, Ma’am,” he replied dutifully.
“Say it!” she demanded.
“I-I need diapers d-day and night—OHHH!” he moaned again as she rewarded him with all nine inches of rubbery cock.
In his heart of hearts, Tommy knew he was totally defeated and that he would submit to whatever demands she made of him, now and in the future. And he knew he could count on being Kaitlyn’s chaste, sissy baby cuckold, forever denied sex or orgasms and that from now on, he would be dressed as a diapered toddler every day. 
Finally, someone had brought him to task for his misdeeds and he was getting his just reward for being dishonest—trying to deceive his wife with the idea that he was a real man, instead of the simpering, weak-willed, bedwetting sissy that he really was deep down.
Jana was going to make sure he was kept in diapers, dresses, and toddler outfits, befitting what a prissy pantywaist he was. 
And in those rare instances when he failed to toe the line—she’d be there with her wooden paddle to teach him a stinging, painful lesson in obedience.
A great story. Tommy was certainly put in his place; he was at some risk of petulance initially but soon had that knocked out of him.
A great story and lickle tommy sure now has learned his place.
Thanks for posting another of your fabulous stories!
Thank you for your wonderful story.
Although the pressure from the cage on my sissy clitty made it a painful experience.

sissy donna
What a delicious story, thank you!
Another Bobby special... poor tommy, even though all the naughty toddlers here are squirming and straining in their peepee cages imagining being him...

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