Putting A Sissy In His Place free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
“Stand up straight–quit slouching,” Mrs. Campbell snapped, as she carefully adjusted the wide, silky pink sash from behind Ethan.

They were facing a full length mirror and he was cringing with shame as he beheld his humiliating, girlish reflection. Mrs. Helen Campbell, his domineering mother-in-law, was fitting him for a new dress that she had just finished, and to his chagrin, it was even shorter than her usual ones. That is to say, it barely came down past his waist and when she tied the big satin sash in the back, it only pulled the frilly hem even higher.

He stared down at the glossy pink Mary Janes that were his normal footwear now, and his knee-high schoolgirl socks, which left his baby smooth, hairless thighs completely exposed.

But to be sure, the worst and most shameful part of his outfit was the fat, bulky diaper swaddled around his hips and the infantile shiny white nursery print plastic panties surrounding them. Ethan knew from his years of constant bedwetting just how necessary they were, but he bitterly resented having to wear them during the daytime, like an incontinent toddler.

Ethan’s hair, which tended to be on the long side, had been combed out into two little girl-style pigtails, with flouncy pink bows that matched his babyish dress.

They were standing in his nursery, a room that only four months previously had been a spare room used just for storage. Now, with the help of some contractors that his wife Megan had hired, it had been converted into a full-blown nursery for a baby girl, albeit, a rather large one.

Everywhere one looked, it shouted out toddler femininity–from the gauzy pink curtains, to the white and pink walls with their nursery print design of giraffes, diaper pins, and building blocks. A large pink dresser stood in the corner, it’s top lined with dolls and baby toys. Next to it, was a crib with high sided rails and a mobile above it that played c***dish nursery rhymes whenever Ethan was put to bed.

A low but sturdy changing table was next to it, and the stacks of thick, fluffy diapers alongside attested to the only underwear the big sissy boy was allowed anymore.

Between his mother-in-law and his wife, the two of them had filled the closet with a vast assortment of cute dresses, onesies, and romper suits, all in soft, babyish pastel colors.

Hanging from a couple of pegs next to the door were two menacing Spencer paddles, one in solid oak and the other in clear lexan–instruments of punishment Ethan was all too familiar with, and they were used without hesitation to make sure he toed the line. His mother-in-law was particularly strict with him, and when she babysat, she ruled the nursery with an iron hand. Defying her was out of the question, and with either paddle, she could bring Ethan to tears in mere moments. He lived in constant fear of being bent over her lap to receive another humiliating and painful lesson at her hands.

Behind him, Mrs. Campbell was taking her time, fussing with the wide satin sash and tying it into a pretty, fancy bow. It was obvious that she had spent a great deal of time and effort in making this dress, what with the lacy accents and little bows in profusion. It looked like something a little girl would wear to Sunday school and it had a built in petticoat underneath that flared out the hem.

Ethan squirmed in place and shuffled his feet, wanting this mortifying experience to end as soon as possible.

Helen hadn’t liked Ethan from the day they first met, nor had she made any attempt to hide her disdain for him ever since. When she first took in his petite, almost feminine stature, and his soft-spoken nature, Mrs. Campbell was certain he was nothing but a big sissy. But it was when she learned of his chronic bedwetting habit, that her worst suspicions were confirmed.

She still remembered the tearful call she had gotten one day from her daughter, in which Megan had let out all her frustrations and dissatisfactions regarding Ethan. It had been the second time that week that she had woken up to wet sheets and she was at her wit’s end.

“Sounds to me like he needs diapers,” her mother had quipped caustically.

At first, Megan was taken aback by such a radical solution but after encouraging her to make a call to Ethan’s mother, she began getting a much clearer picture of the man she had married. To her horror, she learned that Ethan had been wetting his bed all through his teens and his mother had taken what she thought was a very sensible solution of putting him in diapers every night.

In fact, it was not until he had moved out of the house that diapers and plastic panties stopped being a regular part of his nightly routine.

That afternoon, Ethan’s mother paid her a visit, bringing over several boxes of his diapers and supplies. Megan was amazed as she unloaded stacks and stacks of thick cloth diapers, plastic panties in every color and style, baby powder, diaper rash cream, safety pins, and a waterproof changing sheet–everything a baby still in diapers would be in need of.

That night, Ethan was in for a huge surprise as his gorgeous wife laid out a trio of diapers and yellow translucent plastic panties, telling him it was either that or he could sleep on the floor. Needless to say, Ethan was quick to cave in and for the first night in several years, he slept soundly, knowing he was once again safe and protected.

The next morning revealed the wisdom of her plan, for his diapers were soaking wet, as they were to be every following morning thereafter.

While this had solved the problem of wet sheets at night, the room soon began to take on the smell of a baby’s nursery; the pungent, sour smell of pee-soaked diapers permeating the air despite the large rubber bin supplied by Ethan’s mom. This was something Megan had no intention of tolerating, and she immediately moved Ethan into the spare room, although not before putting the waterproof mattress cover on the bed he would be sleeping on.

Megan’s 27th birthday was later that month, and her mother gave her a wooden paddle as a gift, saying that she was sure she could find a use for it. At the time, Megan had laughed it off, thinking of it as no more than a gag gift, but as time went on, she began to think of it in a more serious light.

There had been numerous times when she had walked in on Ethan, only to discover him playing with himself as he looked at pictures of big breasted women on the computer. In the past, this has resulted in some very vocal arguments and a contrite, shame-faced Ethan.

But later on at work, as Megan pictured her husband wearing his nightly diapers and babyish plastic panties, the idea of a c***dish punishment seemed all too appropriate for him.

Two weeks later, she came in one afternoon to find Ethan masturbating again. Snatching up the paddle, Megan grabbed Ethan by the ear and threw him over her lap, giving him the spanking of a lifetime. Fueled by anger and determination, she paddled him until the tears were streaming down his face and he was bawling like a baby. After that, she put him in his diapers and forced him to wear them the rest of the day as an additional shaming punishment.

It was not long after that, that their sex life–such as it was, was severely curtailed by Megan. She had become tired of this pathetic, ineffectual attempts to satisfy her, and between his minuscule penis, and his tendency to prematurely ejaculate, the amount of orgasms she had experienced with him was exactly zero. While this had become a source of irritation and frustration for her, Megan was hardly the type of person to take it lying down.

After spending several hours online doing some research, she soon found what she was looking for. A company called Sissies-R-Us sold a variety of male chastity devices and she carefully selected the one that had the highest rating for security.

If her bedwetting husband couldn’t satisfy her–she was going to make damn sure that he went high and dry as well.

When the device arrived two days later via FedEx, Megan excitedly opened the package and spent some time getting a thorough understanding of how it worked. That evening, as she was preparing Ethan for bedtime, she took out the device and began installing it on his prepubescent-sized genitals, explaining that his inability to satisfy her meant that enforced chastity was going to be a part of his life from now on.

Ethan had been weak-willed all his life, and he was not unaccustomed to being bullied around by those around him. Nevertheless, this was a line in the sand he felt compelled to draw. There was simply no way that he could imagine a life without having orgasms at his whim, and this alarming device spelled an abrupt end to all that.

He argued loudly and vehemently but soon found himself in the familiar position over Megan’s firm lap, getting a blistering spanking with her paddle.

He was still crying uncontrollably as she secured the device around him and snapped the lock shut.

“Your first period of lock up will be three months,” she explained flatly to the whimpering sissy, “that will break up your cycle of masturbating and get you used to a life without erections or orgasms.”

Her words brought on a fresh torrent of tears from Ethan who had begun pulling and tugging at the device, desperately hoping to extract his tiny little penis from it.

“And now,” she told him firmly as she looked him square in the eye, “it’s time for your diapers and plastic panties, you big sissy,”

That had been the turning point for the couple, and the balance of power had shifted irrevocably and forever into the hands of Megan. In the subsequent days, she became bossy and more authoritative with him, dictating how everything in his life would be, from how much computer time he could have, to when his bedtime would be. Arguments were quickly resolved with Ethan being bent over Megan’s lap for a well deserved spanking. In fact, the paddle had become so useful, that Megan soon added another one made of lexan to her collection.

One day, Ethan was foolish enough to be disrespectful towards his mother-in-law, who was visiting for the day. He soon found himself across her knee, his pants around his ankles as she used the new lexan paddle to teach him a painful and humiliating lesson in manners. It was a sorry, sobbing, pantywaist that made his apologies to Helen as he tearfully rubbed his blazing bottom.

As humiliating as this was, it was even worse when her friends were around and Megan made no effort to hide their unequal relationship. She frequently dressed him down in front of them, ordering him around like a servant, and showing everyone who it was that wore the pants in the house.

Ethan had always had a submissive streak through him and he seemed completely unable to stand up to his controlling wife. What little respect her friends had had for him, quickly vanished.

Nor was his bedwetting kept a secret, and soon all of Megan’s friends knew about his humiliating nightwear of diapers and plastic panties. Frequently, she would lead him back out of his room after being changed, to be paraded before her guests like a toddler fresh out of his nursery.

To be sure, they felt absolutely no sympathy for the weak pansy.

Often, if he hadn’t been changed yet, they would tease him beforehand, asking him, ‘where are your diapers, sissy?’ or, ‘looks like someone isn’t wearing his protection yet’. The snide comments were always accompanied by giggles and smirks from her brazen, mocking friends.

The endless humiliations were difficult for Ethan to bear, but perhaps even worse, was his inability to satiate the gnawing sexual desires he felt. He had been a chronic masturbator all his life and having that taken away had left him constantly horny now and desperate for satisfaction. The first two weeks of his chastity were maddening for him, but it only got worse as time went on. Being married to a woman as sexy as Megan meant he was constantly being aroused by her presence; every time he saw a flash of her big, pillowy breasts or her long silky legs, he was beside himself with desire.

He had tried everything he could to extricate his little member but the device had proved to be infallible.

Bed times were another source of frustration for him, as he used to take advantage of his soft, fluffy diapers every night to play with himself. He recalled with longing, splashing his little load into the waiting folds of the absorbent Birdseye cloth and then drifting off to blissful sleep. And since they were always completely soaked by morning, there was never any chance that Megan was going to catch him.

But now–all that was impossible.

His diapers seemed to mock him, teasing him with their multiple cushiony layers while he rubbed himself furiously to no avail.

Often, he would have dreams of Megan, sauntering around the house in her sexy lingerie and heels and he would wake up in a state of frenzy, beads of sweat upon his forehead. He would reach down into his diapers, and for the millionth time, yank and tug at his chastity device in futility.

He had tried making promises to Megan, that he would redouble his efforts to please her, but she merely laughed at him and told him to get used to it. She wore the key to his chastity device on a delicate necklace around her neck, deliberately teasing him with it. Every time Ethan gazed at his wife’s deep cleavage, he was forced to look at the key that could free him from his implacable penis prison.

And all this time, it was Megan’s mother-in-law who kept pushing her to take the next major step with her sissified hubby.

“Megan, there’s absolutely no reason why a woman of your looks should have to live a sexless life,” she had explained, “Go out and find yourself a real man–start dating again. With your body, it would be like shooting fish in a barrel.”

Megan had listened in silence every time she and her mother had this conversation.

“How about your doctor–isn’t his name Frank? He’s incredibly handsome and so tall–he would be a perfect match for you. You know you could have him in an instant if you just sent him the right message.”

Megan nodded her head slowly, considering her mom’s words while in her heart she knew the older woman was correct. And how she had longed for the embrace of a big strong man, one that could sweep her off her feet and fulfill all of her considerable sexual needs.

When she thought of her regular doctor, it always sent a flutter of excitement through her being. He was gorgeous, and the idea of getting him in her bed made her wet with desire. She had never felt that kind of attraction for anyone.

Her marriage to her diaper-wetting husband had been so unsatisfying and here was finally the chance to make things right.

It didn’t take long to achieve. Flashing her pretty auburn eyes and dropping several seductive hints, it only took a routine visit before the masculine doctor asked her out on a date.

Megan was a beautiful woman by any standard but that night, she took special care to make herself look as ravishing as possible. Wearing a plunging, low-cut cocktail dress that showed off her generous bosom and long, shapely legs, she chose a strappy pair of tall high heels to complete the outfit. She styled her long, luxuriant chestnut hair in an elegant style, with pretty tendrils hanging down to frame her high cheekbones.

Before she left, she pinned Ethan into his nighttime diapers and sent him to bed early with strict instructions that he was not to get up or there would be serious trouble. He was fussy and he peppered her with anxious questions about where she was going but she remained coy, telling him only that she was meeting with a friend. Seething with jealousy, Ethan pouted petulantly but put up little else in the way of resistance–he didn’t want to be sent to bed with a sore bottom.

Closing his bedroom door behind her, she placed a small piece of clear tape on the door so she would know if it had been opened during the night. If that tape wasn’t still in place the following morning, Ethan could count on taking a trip over her lap for a long, painful session with the paddle.

Megan’s date with Frank, as expected, went fabulously, and she followed it up with others, until she started spending the night at his house. Frank was a complete gentleman and the polar opposite of Ethan as a lover. To her surprise and delight, his cock was everything she could hope for–8 inches of thick, heavenly glory. He showed Megan how fantastic sex could be and she would always leave his place completely exhausted but satisfied.

She knew it was inevitable that she would have to tell Ethan of her romantic liaisons, and she debated how best to do it until one day she got an idea. Once again, the Internet proved invaluable, and as soon as she found what she was looking for, she placed an overnight order for a particular item.

When it arrived, Megan led Ethan into his room and told him to undress. At the same time, she removed her blouse and slacks to reveal a sexy push-up bra and satin panties. Putting her high heels back on, she told Ethan to bend over his bed, which by now, had begun to smell strongly of stale pee. As he assumed the position, wondering what his exciting wife had in mind, his nostrils were assailed once again with the shameful smell of his c***dish incontinence.

While his back was turned to her, Megan slipped into the sturdy harness of the large strap-on dildo she had ordered, cinching up the straps around her shapely hips to make it secure. She had purposely bought one who’s length and girth matched Frank’s impressive cock.

When Ethan looked over his shoulder to see what his wife was doing, he gulped hard.

“Wha-what are you d-doing?” he quaked nervously.

“Don’t worry baby,” she told him, “I’ll be gentle with you.”

Taking a dollop of Vaseline, she eased her finger into his back passage, working it around until she could fit two more fingers in. Then she dipped the blunt head of the dildo into the lubricant and pressed it against his puckering hole.

“No-no-no,” he whimpered as he tried to squirm away.

Megan slapped his ass hard and threatened to use the paddle if he didn’t quit struggling. That threat was sufficient to make him settle down as she firmly began applying pressure to his back hole. Whining like a little girl, Ethan fidgeted nervously but he squealed loudly when Megan finally pushed the fat head of the dildo past his defeated sphincter.

However, true to her word, she allowed him to get accustomed to the tremendous girth of the phallus before pushing it further in. Ethan moaned helplessly as he gripped the sheets of his bed, struggling to contend with the big, fat, rubbery invader stretching his virgin hole to the limit.

In and out, Megan began slowing pumping her chaste, sissy husband. He was gasping and whimpering, his eyes half shut as Megan initiated a tortuously slow rhythm with the leviathan dildo. To be sure, he felt emasculated and filled to capacity by the monster inside of him–he had never experienced anything like it in his entire life!

Conversely, the huge shaft reminded Megan of Frank’s enormous cock, slipping in and out of her own juicy hole. The thought aroused her tremendously and she began plunging the dildo in with greater enthusiasm.

“You feel this cock, Ethan? This is what every woman needs,” she told her helpless hubby, “this is the kind of cock that I need, and you are totally unable to give it to me.”

As he moaned and squealed like a little girl, Ethan knew just how right she was.

Her excitement level was increasing and her breathing was becoming more rapid. The thought of finally telling Ethan about her wonderful lover was really turning her on.

“That’s why I’ve decided to get it from someone else.”

Ethan’s eyes opened wide as he listened to what she was saying. He felt like his wife had just poured a bucket of ice water over his head.

“I’ve been dating my doctor, Frank…” she paused for effect, “and for the first time since I met you–I’ve finally been satisfied. He has a big, thick cock like this, and he’s reached places you never have.”

She emphasized her remark by plunging the massive rubbery phallus all the way in until it bottomed out, making Ethan squeal helplessly. His legs kicked and he tugged desperately against the sheets but with Megan’s 120 pound frame against him, it was impossible to escape.

“He has such a fabulous, huge cock, and he definitely knows how to use it,” she growled as she ground the dildo hard against Ethan.

“He’s not a bedwetting sissy who wears diapers like a toddler,” she added, gripping his narrow hips firmly with her long-nailed hands. He was forced to endure the full length of her shaft, stretching his aching hole with the mighty cock.

With that, she began a much more aggressive rhythm, pumping Ethan forcefully with the strap-on and bucking him physically against the bed. He slapped the mattress and groaned but he could do nothing to prevent her mercilessly pounding his ass.

Meanwhile, Ethan’s prostate was being vigorously massaged with the big, slippery shaft and even while he struggled to contend with his wife’s shocking announcement, a number of complex feelings were surfacing that were somehow feeding into his arousal. The physical stimulation was hard to ignore and for some reason, the submissive streak inside of him was starting to combine in an unexpected way.

By now, Ethan was two months into his three month chastity sentence, and every day had been an agony of horniness and sexual deprivation for him. The fact was, he was desperate beyond belief all the time now, and totally unable to satisfy his need. Now, as he looked up at the full length mirror in front of him, he could see the look of firm determination on his gorgeous wife’s face. She had never looked so strong, confident, and beautiful. As she pumped him ever harder, he felt to his shock, the beginnings of an orgasm bubbling up and he moaned again helplessly like a little girl.

Megan partially pulled out her monstrous dildo, only to forcefully ram it back in even harder.

With that, Ethan shrieked out, as he came explosively in his chastity device. He gasped and gulped as he groaned in humiliated orgasm, realizing his own lack of self control had shamefully betrayed him yet again.

Megan collapsed on top of him, burying the dildo to the hilt inside Ethan who was still panting for air.

As he slowly began recovering from his eye crossing climax, Megan eased out the dildo, quickly replacing it with a soft, but fat buttplug. It was specially designed to fill him up totally, yet its narrow neck made it impossible to expel.

“Okay,” she said with a smug grin, clapping her hands together for emphasis, “It’s diaper time!”

Deep down, Ethan knew he was utterly incapable of satisfying his wife. For that matter, as a woman, she was clearly out of his league anyway. He had always wondered how he had been so lucky to get her as a wife and now he was realizing the false economy of that relationship. She was beautiful and sexy and still young enough to turn heads everywhere she went–it was absurd that she should do without sex indefinitely.

Nevertheless, as she powdered and pinned him into his thick, bunny soft diapers, he felt ashamed and humiliated at his inadequacy, to say nothing of the emotional turmoil that had left his head spinning. As she pulled his pink plastic panties up his slim, hairless thighs, it only made him feel more pathetic and c***dish.

From that day on, Megan no longer made any attempt to disguise her dates with Frank. Ethan knew without being told what was happening as he watched his wife carefully putting on her makeup and doing her hair, preparing for a long evening of sex and multiple orgasms with her hunky man. His chastity device guaranteed that he would never be a part of that again. He wanted to put his foot down, and tell her that she was his wife and not someone else’s but the paddle was never far away. More often than not, when she told him to pull his pants down and get across her lap, he simply didn’t have the backbone to stand up to her.

Nevertheless, there had been several evenings before a date when she had been required to re-assert her authority, spanking him to tears before pinning him into his diapers for an early bedtime.

That had been three months ago, and perhaps the strangest thing of all, was the subtle change that had evolved in Megan’s attitude towards Ethan. As he gradually began to accept his subservient role, becoming less of an obstacle and an impediment to her sexual pleasure, she began looking at him again with warmth and affection. This was all welcome from Ethan’s perspective, who had thought he had lost his wife irrevocably.

And then, once again, his mother-in-law interceded in their lives, encouraging Megan to make yet further changes. One night, after Megan had put Ethan to bed, the two of them were sipping wine in the living room.

“Do I understand correctly that he hasn’t had a dry night in months?” Helen asked her daughter.

Megan nodded her head with resignation. “He’s no different than a two year-old infant. He wets his diapers every night without fail.”

“I think it’s time you started treating him like the big baby he acts like,” her mother replied.

Megan sat up straight and faced her mother.

“What do you mean?”

“If he’s going to act like a baby, you should start dressing him like one. Let’s get him some outfits for the big toddler he really is. You should dress him in rompers, diaper shirts, onesies, and hey–why not little girl dresses?”

Megan giggled to herself.

“And now that you’ve got a real man in your life, it’s time to convert his room into a proper nursery fit for a big baby.”

Megan was clearly intrigued by the idea and her mind raced as she considered the possibilities. She could easily picture her weak, simpering sissy of a husband, toddling about in a nursery complete with a crib and a playpen. And he could be contained, controlled, and restricted in the same way a real baby had to live. It was the perfect solution.

In addition, there was a part of Megan that actually liked the idea of caring for a baby, albeit an adult one. Due to medical reasons, Megan knew she would have difficulty trying to conceive and it occurred to her that this might, in some small part, satisfy her maternal instincts.

“I love it!” she said at last, her voice filled with enthusiasm, “A bedwetter like Ethan needs a crib to sleep in, so that will be the very first thing I get for him.”

“I can easily make outfits for him on my sewing machine that will fit, but I also think they should be made purposely to humiliate him,” her mother added, “I’ll make them in a prissy, feminine style to emphasize what a big sissy he is.”

“Ha ha!” Megan laughed, “Mother! You’re outrageous!”

Together, they conspired and planned, mapping out the future of her diapered husband who was contentedly sleeping just down the hall.

The next day, Megan placed a call to a contractor with instructions to make a crib, playpen, and a stout changing table, large enough to accommodate an adult, albeit, a petite one. Over the course of the next three weeks, these items were gradually added to Ethan’s evolving room. He watched with concern and consternation as the room began to take on a distinctly infantile character, with nursery print wallpaper going up and a pink dresser installed. Over time, it accumulated a large collection of rompers, diaper shirts, and a large assortment of panties, all cut generously to accommodate his ever present, big, thirsty diapers.

One day, Megan and her mother came into his nursery with a pair of scissors. With great ceremony, they cut up his remaining pairs of underwear and threw them in the garbage, putting a final and permanent end to his adulthood.





Helen finally finished tying the bow in the back of Ethan’s baby dress and she stood behind him, looking critically at the finished product. Making a few adjustments to the frilly hem and the short, puffy shoulder sleeves, she smiled down on the diapered sissy.

“I think it’s adorable,” she exclaimed proudly, a big smile appearing on her face.

Just then, Megan stepped into the room, looking stunning in an expensive, dangerously low cut evening dress. Her big, beautiful breasts were practically spilling out of the top and in her high heels, Ethan was forced to look up into her pretty face. As usual, the act made him feel weak and inferior to his fabulous wife, particularly so, since by comparison, he was wearing a frilly short dress and his fat, embarrassing diapers. The vast difference only reinforced his c***dish status to her.

“Well–you look spectacular!” her mother gushed in admiration, “Frank is going to love that dress.”

“I think so too,” she replied giddily, “I just got this bra in today–look at how much support it gives me.”

Peeling away the spaghetti straps, she modeled in front of them, beaming her gorgeous, infectious smile.

Ethan gaped at the blatant sexual display before him, his tiny little penis quickly stiffening within his tube. He gulped hard, and his mouth went dry as his breathing quickened.

“And how is my little diapered sissy boy this evening?” she asked cheerfully.

Ethan swallowed hard again as he stared first at the two massive globes within her lacy push-up bra, then to the key to his chastity device dangling between them, and finally up at his wife’s ravishing face. Her eyes glittered with excitement and it was painfully obvious she couldn’t wait to see her boyfriend for tonight’s date. Ethan had never seen her so enthusiastic and he was consumed with equal parts jealousy and desire–right now, he wanted Megan more than anything. His tight chastity tube was feeling horribly restrictive and he craved release like never before.

“I’ve just finished this cute little ensemble for him,” her mother explained, “What do you think?”

“I think it’s absolutely darling,” Megan said appreciatively, “my baby has a pretty dress of her own to wear tonight.”

She gave him a playful wink and reached down to pat him on his thickly diapered bottom.

Ethan’s heart was beating wildly as he gazed lustfully at his sexy, unattainable wife. His impotent penis was throbbing painfully, fighting in futility against the restraining tube it was imprisoned in as he took in her flawless body.

Seeing the focus of his attentions, Helen slapped his diapered bottom harshly and pushed his pink rubber pacifier into his gaping mouth.

“Silly sissy–that’s not for you. She’s going out on a date with a real man, not a bedwetting pansy that wears diapers and dresses.

“Look at you,” she scolded him, her voice taking on a cutting edge.

With her hand, she forced his head to turn and look back at his humiliating reflection in the mirror. It had the effect of destroying what little confidence he had remaining. There he was, wearing a dainty baby dress with lace and ribbons galore, a Peter Pan collar and puffy sleeves, thick diapers and waterproof panties, his sissy knee socks and glossy pink Mary Janes.

“You’re not a real man–you’re a sissy!” his mother-in-law added, giving his fat bottom another condescending slap.

Her firm hand landed with a dull thud.

Ethan hung his head in shame, as he often did when Helen berated him but Megan was smiling with satisfaction. She loved how strict and controlling her mother was with Ethan–the perfect babysitter for the diapered sissy.

“If you’re a good boy for grandma, maybe I’ll give you a session with the strap-on tomorrow,” Megan promised with a flirtatious wink.

Under the circumstances, that was as much as Ethan could hope for anymore, but although his opportunities for an orgasm were few and far between these days, being pumped with a big dildo while still locked in his chastity cage seemed like small consolation. This seemed all the more so as his eyes wandered over the breathtaking form of his smoldering wife–the same wife that would soon be wrapping her legs around another man’s waist as he thrust his cock into her eager, wet pussy.

“Come on, Sissy, it’s your dinnertime,” Helen said, interrupting his daydreaming as she took hold of his wrist and led the dispirited pantywaist out of the nursery.

Taking him into the dining room, she helped him into the oversize highchair and secured the strap around his waist, locking the buckle that was purposely behind him and out of his reach. Then she slid the large plastic tray in front where it clicked shut against the sides, further imprisoning him. If that were not enough, two strong velcro straps were soon wrapped around his wrists, completely immobilizing his hands and arms.

Thus fully secured, his mother-in-law busied herself in the kitchen, preparing his dinner.

There was little Ethan could do, other than to swing his Mary Janes and look around the room bored.

Before long, Megan came out and grabbed her keys, striding over to look at her babified hubby, now trapped in his highchair. Helen had tied a large plastic bib around his neck and the playful character of Barney adorned the front.

“Where are you going for dinner tonight, Megan?” her mother asked solicitously.

“Frank’s taking me to this really expensive place uptown–I hear it’s really something,” she replied excitedly, “But to tell you the truth–I can’t wait for dinner to be over so we can head back to his place and I can have fantastic sex with him again.”

“Megan!” her mother chided her with mock anger.

Her daughter giggled and bent down to kiss Ethan on the cheek who was pouting in silence.

“Don’t worry baby, that’s nothing you need to concern yourself with anymore. You just try to keep your diapers dry.”

To think that that one c***dish task was the only responsibility he had anymore!

Feeling extremely frustrated, Ethan’s lower lip puffed out as he sulked and his gaze once more dropped down to the long line of tantalizing cleavage disappearing into Megan’s elegant evening dress. To be sure, all he had to look forward to was a messy dinner of baby food, followed by an early bedtime in his crib.

“And looks like grandma has prepared a yummy dinner for you tonight of Chef Boyardee,” she enthused as she shared her mother’s grin.

Bringing over a bowl of the steaming canned pasta, Helen set it down on the pink tray in front of Ethan.

“Well, be a good boy for grandma tonight, sissy,” Megan instructed him again before sauntering out the door, her sexy high heels clicking loudly on the parquet floor.

Ethan sighed heavily, his disappointment plain on his face.

“Din-din time!” his mother-in-law announced, bringing his attention back to the present situation.

She scooped up a big spoonful of food and quickly shoveled it into his mouth.

“I’m so glad Megan has finally found a real man that can satisfy her–aren’t you?” she asked in a tone of voice deliberately intended to goad him.

Ethan could hardly respond as his mouth was full of Chef Boyardee noodles but he shook his head in disagreement.

“You should know that it was me that encouraged her to cuckold you–in fact, I’m the one who told her to start flirting with Frank,” she told him, twisting the knife even further in the wound, “He’s so much more of a man than you’ll ever be. And now he’s satisfying Megan every chance he gets.”

Although his mother-in-law was 15 years his senior, the years had done little to detract from her obvious beauty. And while she was no longer as slim as Megan, one could certainly see where her daughter got her impressive bosom. Helen had known from early on that Ethan had a weakness for big breasts and she purposely made a point of wearing snug, low cut tops to tease him with. Today was no different, and she was wearing a plunging, scoop neck, fitted top, that clung temptingly to her full bosom, an effect that was not lost on Ethan.

Unlike many older women, Helen had chosen to keep her hair long, and while it had a few grey streaks in it now, it still looked lustrous and full. Today, however, it was tied behind in a look of stern severity.

She still resented Ethan for trapping her daughter in marriage and as a consequence, she took every opportunity to punish and humiliate the chaste sissy, every chance she got.

Ethan swallowed the food in his mouth and glared back at his mother-in-law, the anger rising in him. He was tired of being pushed around by her and he couldn’t stand her constant, condescending and demeaning attitude.

Taking another heaping spoonful of noodles, Helen shoved it into his mouth before he could utter a reply.

“AWGFF!” he squealed, twisting his face away. Some of the messy noodles didn’t make it and they spilled down his chin to plop onto his baby bib.

Ignoring the mess on his face, his mother-in-law continued taunting him.

“Did you see that sexy outfit she was wearing? Wow! What man could resist that?

“By the way–she told me the other day that she stopped taking her birth control. And I know Frank doesn’t wear a condom either when he makes love to her.”

Ethan’s temper finally snapped. He spit out the food in his mouth and flailed his arms furiously with all his might. Unfortunately, the velcro straps were made for just such a display of infantile fury and it achieved him nothing.

At the same time, his rage manifested itself in another, completely unexpected way, and the floodgates of his bladder suddenly opened up, inundating his diapers with a strong surge of hot, insistent pee.

“You’re a bitch!” he shrieked, “I hate you!”

His glossy pink Mary Janes kicked impotently beneath him.

Helen set down the spoon with calm deliberation as she looked down at her captive, diapered sissy struggling against his bonds a mere foot away.

“All done? Because you’ve just earned yourself a nice, hard spanking,” she informed him matter-of-factly.

Ethan twisted and tried to escape, thrashing against the straps around his wrists with all his strength as he continued kicking but it got him nowhere.

Turning on her heel, his mother-in-law strode down the hall towards his nursery where the paddles were kept.

Knowing exactly what was coming, Ethan redoubled his efforts, wriggling and fighting against his bonds but it was no use. By the time Helen returned, he was resigned to his punishment and his head sagged in defeat.

He grew nervous now as he watched her reverse the routine by which she’d originally put him into his highchair. First, she undid the velcro straps and removed the tray table before going behind him to undo the lap buckle.

He always found her calm, cool demeanor the scariest of all her moods–instead of yelling at him, she kept her emotions in check and barely raised her voice. Ethan knew from experience he was really in trouble.

“I-I’m sorry,” he apologized contritely, “I didn’t mean what I said.”

“Ethan, that little tantrum just earned you a trip over my knee and an early bedtime,” she told him firmly as she led him over to an armless chair in the kitchen.

The effeminate sissy whimpered and whined, pleading with her in a desperate, but futile attempt to dissuade her.

“Please–I really didn’t mean what I said,” he blabbered, “I think it’s good that Mommy has a man that can satisfy her.”

At this point, he was willing to say anything to avoid the painful spanking he knew with absolute certainty was only moments away. His mother-in-law had gotten the lexan paddle and he knew it produced much more of a sting than the wooden version.

“That’s good, because you’ll have the opportunity to tell her yourself,” she replied cryptically as she took a seat and set the paddle down next to her.

Ethan stamped his feet in frustration. It was all so unfair!!

Reaching her fingers inside the elastic waistband of his plastic panties, Helen tugged them down past his trembling knees, only to discover the pee-soaked cloth in the front of his diapers.

“Ethan–did you wet your diapers?!?” she demanded angrily.

With all his stress and anxiety, Ethan had been totally unaware of having wet himself but now that it had been called to his attention, he looked down with shock and shame, realizing he had indeed peed his diapers without even knowing it.

His face blushed a bright red and he looked away as he bit his lip in angst. This was a totally new loss of control for him and as bad as his nightly bedwetting was, this was a much worse development.

“I asked you a question, sissy boy,” Helen snapped at him.

Turning to face her dark features, his cheeks burned with humiliation as he slowly nodded his head.

“What is the matter with you?” she rebuked him, “You really are a big baby, aren’t you?”

His eyes brimmed with tears as he struggled to think of something to say.

“You never cease to amaze me. Just when I think you can’t get any more pathetic–you go and prove me wrong.

“Wetting your pampers during your dinner like a little toddler–you should be ashamed of yourself!”

She scolded him like a naughty little boy.

With that, she yanked him over her firm lap and swiftly unpinned his soggy diapers. Ethan let out a sob of despair and he bunched his fists as he suddenly felt the cold air upon his soft, bare bottom. Waves of fear and panic made him shiver as she carefully set his diaper pins aside–he knew just how hard his mother-in-law spanked and he fought back the tears filling his eyes.

Picking up the light but very strong paddle, Helen swung it upwards and brought it down as hard as possible across both his exposed sissy cheeks. The sting was shockingly, painfully intense and it took Ethan’s breath away. His eyes went wide and his mouth opened as he gasped for air, unable even to cry out. However, by the second blistering swat, Ethan found his voice.

He bellowed out at the top of his lungs, kicking wildly as the third and fourth swat landed in quick, scalding succession. Desperate, frantic tears spilled down his face now, as he pounded the floor with the palms of his hands. His soft, curvy cheeks danced merrily under the hard, angry swats of the Spencer paddle while his mother-in-law continued her punishing assault.

Distinctively different from the wooden one, the lexan paddle seared his tender flesh cruelly, producing bright red patterns across his defenseless bottom. The sting was unlike anything he had ever experienced and he sobbed bitter tears of pain and indignation.

For Helen, who deeply resented her pansy son-in-law, she saw this as nothing more than what he deserved for his many inadequacies, although his tantrum during dinnertime had provided a welcome excuse to put him over her lap. Now he was getting a humiliating and c***dish punishment, fit for a bedwetting pantywaist in diapers.

Suddenly, she stopped the spanking, and laid the paddle upon his burning, inflamed bottom. Ethan lay sobbing in his vulnerable position, his bright red bottom fully exposed and his plastic panties tangled around his ankles.

Taking out her cell phone, Helen quickly dialed her daughter’s number and let it ring.

“Hey mom–what’s up?” Megan answered brightly.

“I’m putting you on speakerphone,” she told her daughter, “Ethan threw a temper tantrum during dinnertime and he earned himself a trip over my lap.

“Say hi to mommy, Ethan.”

She held the phone lower and the spanked sissy could barely utter a word that was intelligible, such was the intensity of his sobbing.

“Now Ethan, I thought I told you to be a good boy for grandma tonight,” Megan said with mock gravity.

Before he could reply, the paddle swooped up and came smashing down again across both his singed cheeks, making him howl out in agony.

“WAH-HAH-HAH!!!”

“Tell her what else you did during dinnertime, you little bedwetter,” his mother-in-law snarled.

Trying to reign in his crying, Ethan sobbed and swallowed hard.

“I-I-I w-wet my diapers, Mommy!” he wailed piteously.

He felt utterly ashamed at his announcement.

“Wait–What??” Megan asked incredulously.

“That’s right, the little sissy wet his diapers without even knowing it during dinnertime,” Helen said for him, “Looks like he can’t even control his wetting during the day now.”

Ethan’s wet cheeks burned with humiliation.

There was a pause and they heard Megan giggling in the background.

“Okay,” she said, “you guys are on speakerphone too, now.

“Tell me what you just said, Ethan,” Megan giggled again.

Ethan wasn’t sure what was going on and he hesitated, suspecting she was trapping him in some way.

The paddle came down and left another stinging, angry rectangular pattern across his soft bottom, causing him to shriek loudly and kick frantically.

“Answer her,” Helen prompted him.

“I-I wet my d-diapers during dinnertime,” he wailed tearfully.

This time he heard two voices laughing, one female and the other, male.

“Ethan, meet Frank, my boyfriend and lover,” she said with a proud but smug tone.

Ethan’s face flushed as he realized his humiliating punishment was being witnessed by his wife’s bedmate. Not only that, he had just admitted one of the most shameful things he had ever done to both of them. His cheeks and chest, already a bright red, only blushed a deeper crimson.

“Hey, sissy boy,” a baritone, manly voice said.

Ethan sobbed deeply with shame–this was the most mortifying experience of his entire life!

“He has five more swats to go–would you two like to listen?” Helen asked them.

“Absolutely!” Megan replied as her boyfriend laughed deeply again in the background.

Five more times, the paddle slapped the sissy’s bright red bottom harshly, producing more tears and sobbing along with his helpless kicking.

He was crying uncontrollably when his mother-in-law finally lifted him up.

“Well, I have to go now. I need to change his wet diapers and then I’m putting him down in his crib for an early bedtime,” Helen explained.

Megan giggled and said her goodbyes, ending the call.

As Ethan stood on wobbly feet, bawling his eyes out, Helen looked her sissy son-in-law up and down with disdain.

“You’re nothing but a big baby,” she said, shaking her head, “It’s diaper time for you, followed by beddie-bye time.”

Stopping in the kitchen to retrieve a bottle of warmed milk, she led the sniveling pantywaist back to his nursery. Once there, she sat him down on his changing table, gave him his bottle, and then reached into her purse for something.

“I think it’s time we upgraded your chastity device, sissy boy,” she said as she brought forth a small pink cage-like device made of steel.

Ethan wiped his arm across his wet face and stared anxiously at the diminutive object, certain the change wouldn’t bode well for him.

“This one is different because it has a small, flexible shaft down the center that goes up inside your pee hole. It’s even more secure than the one you’re wearing which is just what a little masturbator like you needs.”

Reaching in her purse for a spare key, she bent down and unlocked Ethan’s chastity device, removing the pieces and cleaning his tiny, shriveled penis with a baby wipe. Despite himself, he started getting hard as he began gazing at his mother-in-law’s full cups, stretching her top in an arousing display before the deprived sissy. Even though he bitterly resented her pushing him around all the time, he couldn’t help but be turned on by her big, sexy breasts.

As soon as she noticed his little nub growing, she stopped what she was doing and shook her head.

“That is absolutely pathetic! Just look at this silly little thing,” she said, pinching his short, thin shaft between her fingers, “You look more like a four year-old than a man down there. But then, I guess it kind of suits your prissy personality.

“Did you know that Megan never had even one orgasm with you?”

His mother-in-law never passed up an opportunity to make him feel inadequate.

She shook her head in disgust as his under-sized penis wilted under her belittling comments.

“Nope. This little thing needs to be kept locked up and deprived of erections,” she said as she began fitting the snug cuff ring of the new pink device behind his sack.

“See this inner shaft?” she said as she offered him a view down the inside of the chastity tube, “Every time you try to get hard in the tube, it will become increasingly painful until you go soft again. It was especially designed for sissies like you who don’t deserve sexual pleasure. Now, no matter how hard your mommy pounds you with her strap-on, you still won’t be able to cum. I wanted to make absolutely sure you wouldn’t be capable of having another orgasm again.”

Ethan choked back a sob of anguish. To think even that last avenue of pleasure was to be taken away, however small and infrequent it was.

Placing some lube on the tiny stainless ball tip of the shaft, she positioned it before his quivering penis.

“Okay baby, this will go inside you easier if you are just a little bit erect. Can you help momma to make sure you won’t be able to have any more orgasms? Go ahead sissy boy, stare at my breasts and fantasize about them while I insert this into you.”

Ethan could have and should have resisted something that clearly wasn’t in his best interests but he was so weak-willed and submissive, he willingly did as he was told, staring hungrily at her big bosom in the stretchy top. Besides, with her warm hand around his little penis, he was completely helpless to his desires. Softly squeezing his shaft, it started to grow again and she rewarded it by carefully working the ball tip into his urethra and down inside him.

“There…that’s a good boy…just what a little sissy needs,” she commended him.

“Oh!” Ethan squealed, unaccustomed to the strange feeling as the cool steel slipped into him.

“Say hello to your new best friend,” his stern mother-in-law said with satisfaction as she watched the stainless shaft slowly disappear into his penis. At the same time, the head of his wiener gradually grew closer to the end of the short chastity tube until it couldn’t go any further. Mating the pins on the cuff ring with the matching holes in the tube, Helen closed the device, trapping his penis within and compressing it even further. Now the poor sissy’s pee-wee was trapped tighter than ever!

Slipping a small titanium lock through the front, she clicked it shut with a crisp and audible snap.

“There,” she said again, “that’s much better. See how it’s even shorter than your old one? It looks like a little pink thimble on you.”

She giggled with amusement.

Ethan gazed down in dismay at his diminutive caged penis, still trying to get used to the strange feeling of having something inserted into his shaft.

“Wha-what about when I hafta go pee?” he asked anxiously.

“Oh, don’t worry about that–you’ll wet your diapers just like you always do–in fact, you may find its a little harder to hold back now. Although after seeing you wet yourself today during dinner, I think you’ve already gone past that stage.”

Ethan didn’t like this development at all but all he could do was to bunch his fists in frustration as she firmly grasped his ankles and swung them over his head, slathering his bright red bottom with Desitin. He whimpered weakly and nursed from the warm milk in his bottle as she laid his legs back down and powdered him thoroughly with the Johnson’s.

“That’s mommy’s little bedwetter,” she praised him as she pinned his fat cotton diapers snugly around his hips, “How does it feel to know that while you’re being put into your diapers and sent to bed in your crib, another man is having wild, passionate sex with your wife, hm?”

Ethan blushed with shame and sucked feverishly on his baby bottle. He always tried hard not to think about what Megan was actually doing when she was gone but his mother-in-law insisted on reminding him of it all the time. But now, with his little penis compressed in this cruel new chastity device, he felt even more powerless and inadequate.

“It must make you sad,” she said unsympathetically as she shook out some yellow translucent baby panties, “But then–this is really where you belong; pinned into some nice, thick diapers and plastic panties like a baby so you can sleep uninterrupted in your crib. You must be very happy that you don’t wake up in a pool of pee anymore.”

Much as Ethan hated it when his mother-in-law derided him like this, he had to admit she was right, even though it crushed him to accept it. And though he could barely admit it even to himself, a small, secret part of himself drew comfort from being safely swaddled in the bunny soft, bulky diapers every night. He no longer gave his nightly bedwetting a second thought.

Ethan winced as she worked the plastic panties around the bulky Birdseye cloth–his bottom still stung terribly from the after effects of the lexan paddle and the snug elastic leg bands cut into his throbbing, punished cheeks. Not only that, he was certain the lingering pain was going to force him to sleep on his stomach in the crib tonight.

Powdering between his thighs, Helen put away his diapering supplies and went over to his dresser to retrieve a night top for him. Quickly selecting a lemon yellow fleece one, she brought it over and after removing his fancy dress, dropped the baby soft top over his outstretched arms. This one had a cute motif of a teddy bear in diapers across the chest and some script she had personally sewn on it saying ‘Diapers–a bedwetter’s best friend“.

“This is certainly true, isn’t it, Ethan?” she said as she showed him the front briefly.

He had been so humiliated when she had first presented it to him months ago, so she had begun making a habit of putting similar phrases on the rest of his jammies.

“Beddie-bye-time!” she announced unnecessarily as she helped him into his crib, pulled his fuzzy pink blankets up and starting the mobile above his head. A nursery rhyme began to play softly as she put his pacifier in, raised the side rail of his crib and clicked it closed.

Ethan clutched his favorite teddy bear in his arms and tried to ignore the painful stinging of his cheeks within his diapers. It didn’t help that his snug plastic panties trapped the scorching heat inside, making his humiliating punishment impossible to ignore.

Walking out the door, his mother-in-law turned off the light switch and tuned to face him.

“Nightey-nite, baby Ethan,” she said pleasantly before closing the door behind her.



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



Ethan was fast asleep in his crib, blissfully dreaming of Megan again…he was watching her on her big bed as she masturbated with her fingers and moaning in glorious ecstasy. His excitement level was rising steadily, like a kettle on a stove, and his eyes roamed over her beautiful, sexy body, drinking in her luscious curves. But just as he was really starting to enjoy the show, at the same time, he began feeling a corresponding pain growing with his penis.

Drifting into uncertain wakefulness, Ethan began to gradually become aware of his surroundings. For one, the moaning he had been listening to was not in his dream, but rather coming from his wife’s room next door. The pain he had felt was also real, and it emanated from the cruel new chastity device his mother-in-law had fitted him for earlier that evening.

He grimaced as he shifted in his crib, feeling now the soggy warm wetness of his diapers that were surrounding him. He took small consolation that there would be no danger of leaks, what with the triple layers of Birdseye cloth and two thick soaker pads in the middle. That, and his big plastic panties ensured his bedding would remain dry, except on nights when he really wet heavily. Feeling carefully all around him, he confirmed that every square inch of cotton was completely saturated and the c***dish smell of pee drifted up under the baby blankets.

He was distracted by the sound of Megan gasping with pleasure in the room next over. The walls in the house were somewhat thin and it seemed he could hear every little nuance of the sex taking place only several feet from his crib.

To be sure, Ethan had never heard his wife moan like this. She was crying out in ecstasy as her new boyfriend plunged his big cock repeatedly into her welcoming pussy.

Ethan felt his cheeks burning with shame and humiliation that she was brazenly having sex just next door to him and making no secret about it. Obviously, she knew full well that he would hear it, and it would excruciatingly drive home his place of subservience.

His rubber pacifier was still lodged firmly in his mouth and he began to suck on it desperately, clinging tightly to his teddy bear for comfort as he heard another man’s deep grunts in the other room. The headboard was banging rhythmically against the wall as Megan’s cries became more urgent–clearly, she was getting closer to climaxing.

Ethan felt his little penis throbbing within his chastity tube and it ached painfully. He tried to think of something else–taxes or sorting laundry, but Megan’s sex-filled voice kept intruding insistently. His member swelled against the inside of the tiny tube and he moaned in agony. Even the residual soreness of his bottom was forgotten as his pecker fought against the invading shaft inside of him.

At last, Megan cried out, her tremendous orgasm shaking the walls with its intensity. He pictured his beautiful wife, only a few feet away from him, breathlessly panting like an a****l while he lay trapped in his crib, the soggy wet diapers embracing him only verifying his proper place in the house. Sucking his pacifier, he angrily slapped his mattress and kicked his feet, feeling more helpless and inadequate than ever.

He thought they were finished, but then ten minutes later, Megan began softly moaning again. Ethan was shocked by her boyfriend’s stamina–he seemed superhuman!

Sure enough, Megan’s sexy voice grew in volume as her lover began all over again. Were they in a different position now? He had no way of knowing. Probably.

He pictured her on her hands and knees, her shapely bottom in the air as her stud pounded her from behind. The vision caused his penis to swell against his chastity tube and he winced again. This was a whole new torture he hadn’t considered. He tried to plug his ears but the urgent banging of the headboard and Megan’s cries of joy slipped past his fingers. Oh, how his little penis ached!

Ethan had to endure another half hour of their lovemaking before the house finally quieted down. Nevertheless, he tossed and turned for quite a while before he finally fell into a fitful sleep.





Warm morning sun shone into the nursery, diffused by the gauzy pink curtains in the window. Ethan could hear birds outside and the others moving about elsewhere in the house but he knew better than to get up. He was only allowed out of his crib when either Megan or his mother-in-law chose to come get him. Until that time, he was required to lie quietly, experiencing the unpleasant feeling of his soaking wet diapers surrounding him and clinging to his skin.

As much as he wanted to be changed, he dreaded the inevitable humiliating meeting with Megan’s lover. He couldn’t imagine being in more shameful circumstances than he was this morning. Greeting his wife’s lover while laying in his baby crib wearing wet diapers was going to be utterly mortifying, that was for sure.

At last the door swung open and Megan came strolling in, followed by her boyfriend. He was much taller than Ethan had expected and his handsome, craggy features revealed how much better looking he was too. He was wearing a pair of boxers and his broad, muscular chest was lightly covered in hair.

Ethan cringed and whimpered against his pacifier as his wife came over and lowered the rail to his crib.

“Good morning, sissy,” she said brightly, “It’s time for you to meet your new daddy.”

Ethan drew his Disney Princess blankets around him protectively, trying to hide his embarrassing baby outfit and diapers from the masculine stranger. With one hand, Megan pulled away his blankets and with the other, tugged him out of the crib, sitting him on the floor of the nursery before them.

“Ethan, say hello to Frank–you are to refer to him as ‘Daddy’ or ‘Sir’, at all times,” she told him, her slim hands resting on her curvy hips.

Megan never went nude around Ethan anymore and this morning, she was wearing a sexy thong and her breathtaking push-up bra.

Ethan blushed hotly, squirming in his seat as the big man looked down on him with a smug smile.

“Well sissy boy, now I can see why Megan wasn’t getting satisfied–looks to me like the only thing you could handle is jerking yourself off,” he said in a mocking, deep voice filled with confidence.

Ethan gulped with shame as his cheeks and ears burned red.

“He’s a little embarrassed because you pegged him exactly right–instead of trying to satisfy me, he used to play with himself every day,” Megan explained.

“I see your mommy made the right decision–putting you back in diapers and chastity, you certainly don’t belong in a man’s world,” Frank observed dryly.

Megan giggled as she boldly looked down at her intimidated sissy husband.

“Ethan, why don’t you tell Frank here why you have to wear diapers and plastic panties.”

Sitting there with the soaking wet cloth surrounding him, he blushed furiously.

“Come on, baby boy,” she prompted him.

“It’s c-cause I’m a b-bedwetter, Sir,” he said, his shaking voice practically a whisper.

“Wow,” he said, shaking his head, “now I’ve seen everything.”

Megan began stroking her boyfriend’s big cock through his boxers and Ethan could tell it was enormous.

“And now it’s time for you to thank your daddy for making love to me and finally satisfying my needs,” Megan said with a smirk.

Ethan blushed deeper at her stinging words, swallowing hard nervously.

“Th-thank you, Sir…for…for pleasing my wife,” he stuttered haltingly. The words ‘my wife’ sounded so incongruous in the present setting.

“That’s very good, but I think there’s a better way for you to show your appreciation,” Megan said as she continued stroking Fran

Same as Putting A Sissy in His Place Videos

2 years ago
  • 0
  • 18
  • 0

Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
  • 0
  • 27
  • 0

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

1 year ago
  • 0
  • 23
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
  • 0
  • 17
  • 0

The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

2 years ago
  • 0
  • 10
  • 0

The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
  • 0
  • 19
  • 0

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
  • 0
  • 15
  • 0

Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
  • 0
  • 10
  • 0

Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

1 year ago
  • 0
  • 14
  • 0

Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
  • 0
  • 19
  • 0

Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

2 years ago
  • 0
  • 15
  • 0

Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

2 years ago
  • 0
  • 11
  • 0

Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

3 years ago
  • 0
  • 16
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

1 year ago
  • 0
  • 23
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

3 years ago
  • 0
  • 17
  • 0

She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
  • 0
  • 12
  • 0

100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
  • 0
  • 21
  • 0

Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
  • 0
  • 14
  • 0

Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

1 year ago
  • 0
  • 12
  • 0

A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
  • 0
  • 23
  • 0

407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
  • 0
  • 13
  • 0

Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

2 years ago
  • 0
  • 13
  • 0

Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
  • 0
  • 10
  • 0

Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
  • 0
  • 20
  • 0

Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
  • 0
  • 21
  • 0

Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
  • 0
  • 19
  • 0

Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
  • 0
  • 15
  • 0

My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
  • 0
  • 12
  • 0

Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
  • 0
  • 16
  • 0

My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
  • 0
  • 27
  • 0

Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
  • 0
  • 30
  • 0

Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
  • 0
  • 12
  • 0

My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
  • 0
  • 14
  • 0

Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
  • 0
  • 13
  • 0

The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

1 year ago
  • 0
  • 14
  • 0

Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
  • 0
  • 15
  • 0

Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
  • 0
  • 17
  • 0

Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
  • 0
  • 22
  • 0

Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
  • 0
  • 20
  • 0

Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
  • 0
  • 13
  • 0

A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
  • 0
  • 8
  • 0

Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
  • 0
  • 25
  • 0

Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
  • 0
  • 19
  • 0

I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
  • 0
  • 11
  • 0

My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
  • 0
  • 14
  • 0

Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
  • 0
  • 16
  • 0

Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
  • 0
  • 20
  • 0

Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
  • 0
  • 18
  • 0

Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
  • 0
  • 17
  • 0

A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
  • 0
  • 27
  • 0

A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

2 years ago
  • 0
  • 12
  • 0

The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

1 year ago
  • 0
  • 11
  • 0

Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
  • 0
  • 16
  • 0

Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
  • 0
  • 23
  • 0

A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
  • 0
  • 9
  • 0

Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
  • 0
  • 21
  • 0

Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

1 year ago
  • 0
  • 18
  • 0

Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

2 years ago
  • 0
  • 10
  • 0

I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

Porn Trends