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Author Topic: Putting a Sissy in his Place  (Read 64480 times)

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Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #7 on: January 09, 2016, 12:18:51 PM »

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


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 pen-is.

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 childish 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 coc-k 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 suc-k 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 pen-is 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 animal while he lay trapped in his crib, the soggy wet diapers embracing him only verifying his proper place in the house. suc-king 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 pen-is 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 pen-is 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.



Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #8 on: January 14, 2016, 11:32:53 AM »
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 circ-umstances 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 coc-k 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 Frank's growing erection. By now, it was tenting his underwear and Ethan feared Megan's intentions.

Slowly peeling Frank's boxers down, she revealed the biggest coc-k Ethan had ever laid eyes on. It was truly massive! Her hands looked small as she gripped the wide base of his shaft, unable to span the huge circ-umference.

His fearful eyes darted from the big bulbous tip to Megan's mischievously grinning face.

"M-Mommy--please--please don't make me do it," he pleaded desperately.
Frank had his hands on his hips, looking god-like, as he stood arrogantly before the weak sissy.

"You've got about five seconds before I pull those wet diapers down and put you over my knee," Frank warned him menacingly.

Ethan gulped with fear--this guy looked like he could break him in two like a twig!
Hesitantly, Ethan leaned forward, unsure just how to proceed.

Without another word, Frank suddenly grabbed the back of his head and simply jammed his big coc-k into the sissy's quivering mouth.
Ethan squealed loudly, his jaws barely able to open wide enough to take in the gigantic head of the man's magnificent coc-k. His jaws were stretching and his lips made a tight seal around the big mushroom shaped head. It felt warm in his mouth and he felt it pulsing eagerly, throbbing with his need. Already, Ethan could taste the salty, pre-c-um that was oozing out of the tip and onto the back of his waiting tongue.

He struggled to back away from the monster being thrust down his throat but Frank maintained a steely grip on his head.

"Use your tongue, sissy boy," he barked sternly.

Scared to defy him, Ethan swirled his tongue under the throbbing underside of his manhood, slurping the sensitive gland that ran the along the front of his mighty sword-like shaft. Frank let out a sigh and he relaxed his grip ever so slightly but not enough to allow the sissy to escape.
Ethan's cheeks were bulging wide and he marveled at the fat girth of this man's member. Frank began pushing it in until it bottomed out against the back of the sissy's throat and he heard Ethan beginning to choke. Then, he slowly eased it out before plunging it back in again.

Meanwhile, Megan was grinning ear to ear and she took out her cell phone, happily snapping close up pictures of Ethan's mouth filled to capacity with hard man meat.

"This is right where you belong," she purred, "On your knees, with a big coc-k shoved in your mouth."

"Get ready Diaper boy," Frank said in a husky voice, "cause I'm gonna c-um in your mouth and you're going to swallow every last drop."

Ethan whimpered in anguish but his jaws were stretched to the limit trying to take in the massive shaft pistoning in and out of his warm, wet mouth.

Suddenly Frank held his breath and he backed his coc-k out just enough to keep the head in Ethan's mouth. With a loud roar, he blew his manly load, filling the sissy's mouth with warm, creamy semen. Ethan's eyes went wide and he squealed as he waved his hands in helpless desperation. Forced to swallow the sticky goo that was overflowing his mouth, he tried to back off but Frank held his head firmly as he sprayed another big load down his throat.

Megan clapped her hands with glee as her sissy hubby struggled with what seemed like a gallon of semen. No sooner did he swallow one load than another erupted into his eager mouth.

"Good job, coc-ksuc-ker," Frank commended the distraught pansy in a condescending voice, "Just keep swallowing."

Ethan was waving his hands in protest but there was little he could do.
The inside of his mouth was lined with a slick coating of c-um and as the gargantuan coc-k finally popped out his mouth, his tongue unconsciously licked his sperm covered lips.

"Don't worry--you'll get plenty of chances to practice. I always wake up with a hard-on and every time I stay the night here, you can count on giving me a blow job," Frank informed him.

Ethan was crushed with humiliation. It was bad enough that he had to tolerate his wife sleeping with another man (in his deluded mind, Ethan still thought he had some say in the matter), but now he had to get on his knees and suc-k this man's coc-k every morning? How degraded could he get?




Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #9 on: January 15, 2016, 03:51:35 PM »
Six months later...


"Quite struggling sissy..." Melissa sternly warned Ethan as she began firmly applying greater pressure to the big blunt dil-do positioned between his trembling cheeks.

He was bent over her lap, with his thick diapers unpinned and pulled back between his smooth, girlish legs. His baby dress and petticoats were piled around his torso and a look of dire concern was on his face.

"Oh! No, Grandma--its too big!" he squealed as he helplessly waved his hands in the air.
"I know its bigger than your usual nozzle, but a sissy like you can take it--spread your legs wider and relax, it will go in much easier for you if you just submit."

The nozzle, which resembled a very large, lifelike rubber coc-k, was attached to a long white hose that ran upwards and ended at a glistening red rubber enema bag, hanging from a hook that was bursting with two quarts of hot, soapy water.

Ethan's bottom was still showing some residual markings from a hard spanking he'd received the other day and he was reluctant to say or do anything in opposition to his strict, domineering mother-in-law.

"Come on sissy--be a good boy for momma," she urged him in her usual kind but condescending tone. 
Whimpering and bunching his fists, Ethan did as he was told, submissively spreading his legs wider and trying to relax enough to allow the rubber leviathan to get past his puckering, reluctant sphincter.

"Theeere you go," she said with satisfaction as she finally pushed the big, bulbous head inside him, making him squeal loudly.

"OHHHH!!" Ethan cried as his eyes went wide.

"There you go," she said again, twirling the slippery fat rubber nozzle around inside him before slowly pushing it in farther.

Ethan's tight hole was stretched to the limit as the huge nozzle was pushed in even further and he moaned weakly. While it was true that he had become somewhat used to being invaded like this, either from Megan's strap-on dil-do, or his mother-in-law's usual enema nozzle, this one was much bigger.

Melissa pushed it until it bottomed out, eliciting more girlish moans and squeals from her weak-willed, sissy son-in-law.
She smiled to herself when she thought of what Megan had in mind to announce to him later today and this emasculating enema seemed like the perfect prelude to that meeting. She had found that a good soapy enema always left Ethan feeling a little more subdued, compliant, and submissive, and willing to accept further humiliations more readily. She had in mind to make him wear his biggest, fattest butt plug during the meeting, which would only further embarrass him.

They were in Ethan's nursery and Melissa could see the look of angst on his face, reflected on the wall mirror across from them. She toyed with the nozzle a bit and then plunged it back in all the way before holding it there steady.

"Ready, baby Ethan?" she asked cheerfully.

The poor sissy found he was never ready to receive his enema but of course, it was truly a rhetorical question. He was going to get his purging whether he was ready or not.

Sure enough, without waiting for an answer, his mother-in-law released the clip on the hose and hot soapy water surged unhindered, deep into his bowels.

"Unnngg," Ethan grimaced.
He clenched and unclenched his fists, gasping as he tried to deal with the feeling of fullness that was quickly developing inside him. Glancing up at the mirror, he saw his mother-in-law with her usual, smug, superior expression on her face. She was wearing a pretty white blouse that she had purposely unbuttoned to show off her deep cleavage but at the moment, that was the last thing on Ethan's mind.

Open and closed, taking her time, she carefully manipulated the clip, watching him squirm and waiting until she thought he could take another dose of the warm, sudsy liquid before opening the clip again.

When she had first started administering enemas to him nine months ago, he had barely been able to take a quart, but since then, she had learned that by stretching out the process, and patiently making him take it over a longer period of time, a much greater quantity of the soapy water could be taken in. And she wanted to make sure he took in every possible drop for a nice, full, punishing enema.

Melissa often used these sessions to scold him for his shortcomings or some failure on his part with the housework, which had become his primary task in the household. Bent over her lap and completely at her mercy, Ethan could do little more than squeal and moan helplessly as she scolded him like an errant child.
Today, however, she decided to use it to give him some rare praise.

"Frank tells me you've become quite the little coc-ksuc-ker," she remarked while she was waiting for the water to settle inside of him.

Ethan moaned and squirmed on her lap, trying in vain to get comfortable.

"Yes, he says you're the best coc-ksuc-ker he's ever had and that you can make him c-um in less than five minutes now...that's quite an achievement," she remarked sardonically.

Sensing that he could take some more, Melissa undid the clip and another powerful surge of soapy water gushed into Ethan's waiting bottom.

"He says he looks forward to his mornings here when he knows you'll eagerly slurp and suc-k on his big coc-k, anxious to swallow his huge loads of creamy c-um."

Ethan blushed with bitter shame. He hated having to get on his knees for his wife's lover and submit to giving him blowjobs like a cheap hooker,  but he'd already suffered several blistering spankings over the larger man's lap and didn't want to experience another one again. To Ethan, five minutes of degradation (and the humiliating, demeaning comments that followed) were well worth avoiding the pain and suffering of one of Frank's hard paddlings.

"Its good that a sissy bedwetter like you knows his place and has finally found something that you're good at," she said, sounding almost genuine in her flattery, "To be sure--your place in this house is on your knees, with his big fat coc-k, balls deep in your mouth.
"What's it like when he blows his load down your throat? Do you have a hard time swallowing it all? He says you don't gag anymore so you must have really mastered the skill."

Ethan was moaning and squirming--most of the rubber enema bag was empty now and he could feel the volume of warm water distending his belly and giving him cramps.

"If you were more of a man, maybe you'd be in the other room, making love to my daughter. Instead, you're in here, with your diapers pulled down, bent over my lap getting a long soapy enema....I'd say you're right where you belong, wouldn't you?"

Ethan lay there and moaned weakly until his mother-in-law pushed the dil-do in to prompt him.

"Wouldn't you?" she asked again more forcefully.

"Y-yes ma'am," he squeaked, "This-this is where I belong."

Melissa rewarded his submissive obedience with another surge of soapy water.

Ethan gritted his teeth and swallowed the groan escaping his lips as he reflected how true her words were. He had gone from being 'the man of the house', to being the baby cuckold of the house, subject to daily humiliations and punishments at his cruel mother-in-law's hands. She had become his primary caretaker, although it was questionable just how much caring she did. Since Megan had become more and more deeply involved in her affair with Frank, Melissa had assumed the role of Ethan's babysitter and guardian, changing his wet diapers and dressing him for the day, feeding him in his highchair and putting him down in his crib for his naptime.

Finally, the last soapy suds disappeared into Ethan's bottom, but Melissa held the nozzle firmly in place, just to make sure. Ethan whimpered weakly, praying silently that she would allow him up to release the churning liquid in his bowels.
At last, to his utter relief, he felt the wide, slippery nozzle easing out of his aching hole, along with his mother-in-law's admonishment not to let any leak or he'd be right over her lap again for a blistering spanking.

Precariously, Ethan limped off to the bathroom where he spent the next ten minutes expelling the punishing liquid.


Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #10 on: January 17, 2016, 12:47:26 PM »
After he returned, he found his mother-in-law once again seated in the only chair in the room, a stool that served as Ethan's spanking chair. Next to her on the changing table, was a tall, fluffy stack of diapers awaiting the emasculated sissy.
She beckoned him over impatiently, holding a large pink butt plug in her hand.

"Over here, Ethan," she said as she took his hand and briskly guided him back over her lap.
He recognized it as his biggest one and he put up his other hand in protest.

"No Grandma--please--not that one."
Ignoring him as she always did, she firmly pulled him over her lap and forcefully spread his legs as Ethan whimpered miserably. Taking a big dollop of Vaseline, Melissa pushed it up inside his hole and then positioned the imposing butt plug at his quivering anus. Fortunately, it had been stretched pretty thoroughly by his new enema nozzle so that when she began pushing the butt plug in, his sphincter was quickly defeated.

"OHHH!!" he cried as the fat plug slipped inside him, filling him completely.

"That's my sissy boy," she commended him as she patted his cheek and helped him over to the changing table.

Handing him his baby bottle of milk, she busied herself slathering his bottom with a sticky coating of diaper rash cream before powdering his hairless groin and tummy with baby powder. Looking down at the diminutive pink chastity cage imprisoning his little pen-is, she smiled again at her own resourcefulness. That tiny nub would never experience an orgasm again now that she was in charge of him, she thought with satisfaction.

Ethan studiously tried to ignore his mother-in-law's big breasts swaying within her unbuttoned blouse as she reached past his head to get his diaper pins but he was unsuccessful. Nevertheless, he had discovered that so long as he didn't actually stare at them for more than a few seconds, he wouldn't suffer too greatly. It was those long periods of boring inactivity spent in his playpen, when his eyes would wander and fixate on her busty profile, that he would start to feel the pain in his tiny pee-wee.
And it was made worse by the fact that his diapers were so soft and fluffy--just brushing his hands against the slippery plastic front of them brought back pleasurable memories of his previously unrestrained masturbating habit, before chastity had been forcefully imposed upon him.

He certainty couldn't complain that they were uncomfortable. The fact was--secretly--he loved wearing his bunny soft diapers. But putting aside the embarrassment of actually using them, he found them to be a double edged sword. On one hand, they made him feel safe and secure, but on the other, they constantly teased him with their soft, spongy layers.

Melissa selected a pretty yellow pair of Disney Princess-themed plastic panties and gathering the leg holes together, worked them over Ethan's feet and ankles. These were a favorite of hers, since they had three cute white plastic rows of bouncy ruffles sewn across the top half of the seat. Working them over his fat, bulky diapers, she ran her fingers around the elastic waistband, making sure all the soft Birdseye cloth was contained inside.

"There--no need to worry about you wetting yourself and leaking now," she said as she powdered between his legs, "Now you can play until naptime and I'll change you then."

Ethan bit his lip in embarrassment as he unconsciously glanced once more down his mother-in-law's deep cleavage. It was becoming harder and harder to keep his diapers dry, even during the daytime. Often, he would have what he called 'accidents', particularly if he were surprised suddenly, or scared in some way. It was always humiliating having to ask Melissa for a diaper change during the day, and more often than not, she'd make him wear his wet diapers until naptime or bedtime, just to spite him.
Ethan was at a loss to explain his increasing loss of control during the day, but his mother-in-law seemed to expect little better from him.

"I think we'll leave this top on you today," Melissa remarked as she began putting his glossy white Mary Janes over his feet. Made of soft, fuzzy fleece, the top matched his panties and had the humiliating script; 'Bedwetters wear diapers' on the front.

It was all the same to Ethan these days, who obviously had no say in how he was dressed anyway, and he took Melissa's hand as she led him out of the nursery and into the kitchen where Megan was making coffee.

"Morning mom--would you like a cup?" she asked solicitously.
"That would be great, she said as she helped Ethan climb awkwardly up into his highchair. As soon as he'd settled into the seat, Melissa moved the step stool away, leaving Ethan's feet unsupported. The sissy shifted     in his seat gingerly, the fat butt plug inside him making him feel invaded and serving as a constant reminder of his lowly position in the household. After securing his wrists and waist strap, his mother-in-law busied herself feeding the captive sissy. Today, she was particularly haphazard with his feeding and his mouth and chin were soon caked with the slop of his breakfast.

Megan was fully dressed this morning and she wore a low cut sweater that clung to her mouthwatering bosom. Ethan presumed she was going somewhere, because she was wearing tall, high heeled pumps with a pair of silky slacks that were hugging her perfect figure. As usual, she looked very adult, while he looked like the epitome of a sloppy-faced, helpless toddler.

Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #11 on: January 21, 2016, 03:57:57 PM »
Suddenly, the front door opened and Frank came in, followed by a woman Ethan had never seen before. She was smartly dressed in a feminine pant suit and her expensive sunglasses lent her a very sophisticated air--in fact, everything about her exuded style and class.
Her hair was pulled back and arranged in an elegant manner, and she immediately strode across the room to get a better look at Ethan.
 
Even though by now, Ethan had become somewhat used to being exposed before others, each time it was someone new, he found it to be an excruciating experience. Removing her sunglasses, the woman came up to him and looked down on the squirming sissy, the disdain obvious on her pretty face. As the fat butt plug ground deeply into his back passage, Ethan helplessly felt his diapers suddenly growing wet and warm and he blushed furiously.
With his Mary Janes swinging uselessly, he struggled pathetically against his wrist straps and looked around the room, as if seeking help from Megan or his mother-in-law.
 
Reading the script on Ethan's chest, the woman smirked condescendingly.
 
"So--this is your little bedwetter," she remarked scornfully, "I can certainly see why you put him in diapers and found yourself a real man."
 
Ethan whimpered as he felt another strong surge of hot pee flooding his diapers. This was SO humiliating!
He tried desperately to stop the flow as his bulging diapers happily absorbed all his panic-induced pee.
 
"I have to confess that a part of me didn't believe you, but now that I've actually seen him for myself, it all makes perfect sense," the woman said as she turned to Frank and set a satchel she had been carrying down on the kitchen table.
Melissa stepped forward and shook the woman's hand.
 
"Ms. Milani, I'd like you to meet Ethan Grant--Megan's sissy hubby," she explained, "Yes, he is a chronic bedwetter and masturbator--or rather I should say--a former masturbator. Since he's been in strict chastity for almost a year now, he's been prevented from being able to play with himself like he used to.
"Needless to say, with his tiny, baby-sized pen-is, he was completely incapable of satisfying Megan--or any woman, for that matter."
 
With the fat butt plug stuffed inside him, and his warm, wet diapers embracing him, Ethan felt vulnerable and inferior. He blushed with shame as Ms. Milani looked him over critically and shook her head, the disapproval written all over her pretty face.
 
"You smell like pee, powder, and pampers," she remarked in a superior, patronizing tone.
 
Megan sauntered over to Frank and wrapped her lithe arms around him, reaching up to give him a passionate kiss of greeting. His big hands roamed all over her slim, curvy body as he kissed her back enthusiastically. Ethan blushed again and looked the other way, embarrassed to have his shameful cuckold status so blatantly demonstrated.
 
Finally, Megan released her embrace of Frank and turned to face Ethan.
 
"We have an announcement to make," she said with a smile.
 
Rather than looking at her daughter, Melissa turned to face Ethan, as if more interested to see what his reaction would be.
 
"Ethan, you are a pathetic excuse for a man. I have no idea why I ever agreed to marry you, but thankfully, Jordan here is going to take care of all that.
"I need a real man--not a sissy who can't even keep his diapers dry."
 
Walking over to look down at her cowering husband, Megan reached underneath the plastic tray and stuck a finger inside the elastic leg band of Ethan's plastic panties.
 
"Oh my god--you're wet again?? Can't you even control your wetting during the day now?" she demanded.
 
Ethan blushed hotly as everyone in the room stared at him.
 
"It-it w-was...uh, an accident," he stammered as she squirmed in his seat.
 
"You should paddle this little sissy when we're done," Megan said as she turned to face her mother.
 
"I'll be happy to make him cry," Melissa said as she crossed her arms over her impressive chest and looked down at the sniveling sissy, "Jordan--if you've ever wanted to see a sissy bawling his eyes out like a baby, stick around."
 
"I'll do that," she said as she began taking papers out of her satchel and arranging them on the table.
 
Mirroring her mother's pose, Megan crossed her arms and looked down at Ethan.
 
"Well sissy, you don't have many choices around here but today you have two. I can have our marriage annulled and have you tossed out in the street, or..."
 
Tears misted Ethan's eyes and he held his breath...whatever else she was going to offer couldn't possibly be worse than what she just suggested.
 
"Or...Frank has generously offered to let you move in with us, into a separate wing of his mansion. There, mom will be fully in charge of you--she has shown a real knack for how to handle bedwetters and sissies like you, so I know you'll be in good hands. She'll make sure you get all the diapers and discipline you so obviously need.
"Don't worry--I'll still come in and take you with my strap-on from time to time. Or maybe Frank will decide to pop your cherry...he's mentioned your little sissy bottom might need a big hard coc-k from time to time."
 
Ethan squirmed as he considered his choices, the intrusive fat butt plug only adding to his discomfort.
 
"And after our marriage is annulled, I will become your legal guardian--the inheritance you received last year will all go to me."
 
Ethan swallowed hard as another strong surge of pee saturated his diapers.
 
"Well--what's it going to be sissy boy?" she demanded.
 
"I-I...I wanna live with you," he whimpered weakly, his cheeks burning with the shame of his capitulation.
 
"Very well," Ms. Milani said, "I have everyone else's signatures--I just need Ethan's."
Bringing over a sheath of papers, she placed one of them on the highchair's pink plastic eating tray.
 
"This one recognizes that your marriage was brought about under false pretenses and should be annulled. Obviously, Megan thought she was getting a man out the arrangement but we both know that couldn't be farther from the truth. Just sign here," she said pointing to a place on the lengthy doc-ument.
 
Ethan sniffled and accepted the proffered pen, scribbling his signature on the line.
Placing another paper before him, she pointed at another line.
 
"And this one gives Megan complete rights over you as your legal guardian...I was able to find some ambiguous mental clauses that speak to your...immature behavior and childlike disposition.
"By signing this, you forfeit all your legal rights and won't be able to do so much as get a library card anymore without Megan's approval."
 
Ethan cried softly as he submissively signed his name to the doc-ument, shamelessly handing over everything to his wife. Ms. Milani shook her head at his spineless display--it only confirmed in her mind that this is what he truly deserved.
Meanwhile, his mother-in-law had left the room to retrieve the paddle for his promised spanking.
 
"And lastly, this doc-ument relinquishes control over the inheritance you received last year. It now becomes the sole property of Megan."
 
"Don't worry baby--" Megan smirked, "I got you a piggy bank and your new allowance will be fifty cents a week."
 
She watched eagerly as the defeated sissy signed away his rights to the staggering amount of money that he'd originally used to leverage his way into the marriage. Bitterly, he reflected how that deception had cost him!
 
His mother-in-law had returned, and was standing by his side now, the menacing long wooden Spencer paddle in her hand.
 
"And now, someone's going to pay the piper for wetting his diapers," she said as she began releasing him from the bonds of his highchair.
 

SissyShellyDC

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Re: Putting a Sissy in his Place
« Reply #12 on: January 22, 2016, 06:47:07 PM »
Ooooh, I love this story.  I hope you do a "six months later" jump.  When you did that with Barbara's Baby Girl, it was amazing!

Baby Bobby

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Re: Putting a Sissy in his Place
« Reply #13 on: January 25, 2016, 06:08:53 PM »
Ethan began crying openly now, his hands going up and waving in protest.

"No-no-no!" he wailed, stamping his feet in place. This was all so unfair!

Taking a hold of his left wrist with her free hand, Melissa jerked him forward and swatted him hard across his thickly padded, diapered seat. The sassy ruffles across the back of his plastic panties fluttered and then settled back down. 

"OWW!!" he cried out, causing the others to laugh at his weak, pathetic display.

With her commanding presence, Ethan didn't dare stand up to his intimidating mother-in-law. He was about to get his bottom paddled and he knew there was nothing he could do about it.

Calmly seating herself on the armless kitchen chair, Melissa reached over and began peeling his clinging plastic panties down off his sopping wet diaper. Tears of shame tumbled down Ethan's cheeks as the childish smell of pee once more surrounded them, proving to everyone how little control he had.

"Well...I think this seems like a very appropriate way to start your new life, with a trip over momma's lap for a good, hard spanking," she said as she took the sniveling sissy over her knee.
In no time, his big, soggy diapers were unpinned and pulled back between his legs, exposing his tender bare bottom for punishment.
Ethan's damp cheeks twitched and flexed as his sphincter nervously gripped the big butt plug lodged inside him, unable to expel it.

Without warning, the hard wooden paddle came down with a tremendous impact, loudly slapping both his soft cheeks and flattening them before swinging back up for another vicious swat.

Ethan howled out in pain and shook his fists in the air as the paddle rained down in rapid succession on his quickly reddening bottom. Kicking his Mary Janes wildly, he slapped the floor miserably as his mother-in-law gripped him tighter and smacked his blazing bottom repeatedly with even greater force. The tears streamed down Ethan's face to spill on the floor below him as he howled out with each nasty bite of the unforgiving paddle on his tender, scalded rump. The numerous air holes in the face of the paddle provided extra sting, while the hard solid oak ensured that the poor sissy would have difficulty sitting for days afterwards.
 
Melissa had a well deserved reputation for efficiency and she made sure every square inch of his backside received its proper share of the paddle. When at last she was done, his bottom was thoroughly punished, bright red and swollen.

Ethan was crying hard, his breathing coming in ragged gasps as she helped him up on his shaky feet and stood him before the others. Ms. Milani looked down unsympathetically at his now exposed, caged little pen-is before gathering her papers and putting them back into her satchel. With his plastic panties tangled around his ankles, Ethan stood and cried unashamedly like a baby before everyone, partly from the spanking but also due to having been legally reduced to the status of a toddler.
But to be sure, his humiliating display only confirmed to Megan, the wisdom of the choices she'd made.

"Come on sissy--its time for your diaper change," Melissa said authoritatively as she took his hand and led him out of the kitchen.
Ethan rubbed his scorched bottom as the tears continued to stream down his cheeks.

Now that his status had been confirmed, Melissa thought she would try and cheer him up a bit.
"Frank tells me he spared no expense and you can look forward to an totally fabulous baby nursery when we move in with them," she said enthusiastically, "Lots of baby toys, dollies, new outfits--everything a diaper-wetting, pampered princess could desire. Won't that be wonderful?"

Ethan shrugged helplessly. Now he was well and truly trapped.

"Of course, now that you'll be in the same house with him, I think you can expect to start off each day with his big hard coc-k in your mouth," she added.

Ethan sniffled miserably as he looked down at his own tiny little pen-is, locked away forever in its thimble-sized pink cage, never to be hard again.

"Oh, and I've found a babysitter to help me out when I have my own errands to run. I know you'll just love her--she's very pretty and well--let's just say you won't have any objection to her body," she said with a conspiratorial wink.

"Her name is Tiffany Johnson."



THE END

 

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