A Sissy Gets Punished
My husband Bob was sitting on the couch in our living room, fidgeting nervously, and for good reason. Two days ago, I had caught him red-handed, masturbating to porn on our computer at home. This had not been the first time I had caught him but I was determined to make sure it was the last.
In addition to being a compulsive and frequent masturbator, my husband also has a strange and kinky fetish for wearing diapers and baby clothes. I don’t pretend to understand it but I have grudgingly tolerated it, so long as he does it when I’m not around. However, that doesn’t give him carte blanche to masturbate and he knows internet porn is strictly forbidden.
When I caught him this last time, I was furious and I stormed out to go visit a good friend of mine who is very strong willed and supportive. She listened to my story and told me she’d come over and “straighten things out”, whatever that meant. All I told Bob was that she would be coming over and as his punishment, I wanted him to wear one of his sissy baby outfits. He was at first, very resistant but I sensed a part of him was also turned on at the prospect of being humiliated in front of another woman. Little did he know what was in store for him!
Bob was sitting there, wearing a pink and white gingham baby dress, lacey anklets and mary janes, a thick diaper and frilly nursery print plastic panties. He looked completely ridiculous and I watched him biting his lip anxiously as we waited for my friend to show up.
At eight pm sharp, we heard the faint sound of high heels approaching down the hallway of our apartment building, followed by a sharp knock on the door. Bob nearly jumped out of his dress and I saw him make ready to bolt for the bedroom to hide.
“Don’t move so much as an inch!” I warned him firmly as I went to open the door.
Barb stood there in all her regal superiority, a very attractive and successful woman of twenty-seven. Her long brunette hair was piled into a neat, businesslike bun on top of her head which, like the rest of her outfit, made it clear she was on a serious mission. She wore a grey skirt that hugged her slim figure and a white blouse buttoned loosely around her torso. Underneath she had a tan halter top which clung tightly to her proud, voluptuous bosom. In her five inch high heeled sandals, she stood a good deal taller than I.
“Thank you so much for coming over,” I said as I hugged her and invited her in.
She smiled briefly but warmly at me and then her gaze fell on Bob severely.
“And you must be the little sissy masturbator, Heather told me about,” she said disdainfully.
Bob hung his head in shame and his face burned red as he withered under her iron stare.
Dropping her bag on the floor, she stepped over to look down at the pathetic form of my husband, cringing like a sorry little girl in his pink baby dress and diapers.
“Stand up Sissy, and let me have a look at you,” she ordered him brusquely.
Unsure of himself, Bob looked first at me and then up at Barb who was glowering down at him with her well manicured hands on her hips in a stance of typical female superiority. Reluctantly, he slowly stood up although he still fell short of her towering presence. No doubt the fantasy image he had kept in his mind of parading around in front of other women was beginning to fall apart as he struggled to cope with depth of humiliation he was feeling now. Certainly Barb had no more empathy for his fetish than I did and her stare was making Bob wilt. She looked him up and down, shaking her head in disgust.
“For the life of me—I can’t fathom why Heather puts up with a sniveling sissy like you who likes to play with his p_nis. Just look at yourself! A grown man wearing diapers and plastic panties like a baby. And that dress! You look like you belong in a nursery suc-king your thumb and playing with dollies!”
Bob was crushed with shame and he stared miserably at the floor.
“Heather, can you bring a straight backed chair into the living room please? We have some business to take care of,” she asked me as she crossed her arms over her ample chest. It must have been twice as devastating for Bob to be seen like this by a hot woman he could never hope to get in the outside world--she was way out of his league.
“Well,” she said firmly as she looked him squarely in the eye, “today we’re going to teach you a lesson as to what happens to little boys that like to play with themselves.”
When I placed the chair in the room, Barb sat down slowly, gracefully, and purposefully, smoothing the folds from her sleek skirt. Reaching into the bag she had brought with her, she produced a long, rectangular wooden paddle with two rows of holes drilled into it.
“I intend to give you a hard spanking, Sissy-boy,” she warned him evenly, “It’s going to hurt like hell and before I’m done, you’ll be crying like the big baby we both know you are.”
Instinctively, Bob began rubbing his fat, diaper-covered bottom, not realizing anything like this had been planned for him. He probably thought I’d make him prance around in front of this stranger and that’d be it but I had much more in store for him than that.
“Heather…do I have to--” he began, but Barb cut him off abruptly in a tone that could shred metal.
“You will address her as ‘Mommy’ and myself, as ‘Ma’am’—is that understood?”
“Ye-yes Ma’am,” he replied quickly, his voice shaking with fear.
“Good. I enjoy making bedwetters and masturbators cry and I can see that you’re both. Are you getting scared, little boy?”
“P-please don’t do this, Ma’am,” he quaked.
Barb slapped the palm of her slim open hand with the paddle which sent a shiver through Bob.
“You look like you’re going to cry before I even start, Sissy. And your prissy little outfit certainly befits your personality—do I need to check to see if you wet your diapers too?”
“No Ma’am,” he mumbled miserably.
“I’m going to see that Heather continues to administer the same kind of discipline from now on so you can look forward to a future of many, many sound spankings. Whatever you imagined this would be like in your perverted little fantasies you can just throw out the window. I spank for one reason and one reason only—to punish little sissies like you. We both know you need this paddling and I’ll see to it you get what you’ve got coming. Feel free to kick your feet and cry your little eyes out—most little sissies do.”
Bob’s lower lip was trembling nervously and he looked very much like a frightened little boy, caught by his mommy. I could see that Barb’s force of personality was enough to cow him completely without even laying a finger on him.
“Okay Mr. pantywaist—it’s time to pay the piper. But we have just one last thing to do before we get started,” she said as she reached into her bag.
“Because you live in an apartment, we can’t have you howling and bawling at the top of your lungs. Therefore, I’ve brought a little something to keep you quiet while I settle accounts on your bottom.”
She produced a large p_nis shaped gag that had a strap on either side and a buckle at one end. Standing up, she positioned the blunt end of the coc-k at Bob’s lips.
“Open up, Sissy, here’s a nice big coc-k for you to s_ck on while I’m blistering your bottom.”
“No—no--” he backed away and whimpered but Barb was too quick for him. With lightning movements, she shoved the rubber p_nis past his protesting lips and immediately ducked behind him to secure the straps in the buckle. Bob’s eyes widened in panic and he squealed loudly through the fat coc-k filling his mouth but his screams were quickly reduced in volume due to the size and design of the device. He struggled in vain to stop Barb from securing the buckle but she merely slapped his hands away, continuing her effort without difficulty. In seconds, the gag was cinched in place and Bob’s protests came out only as weak incoherent whimperings as he was forced to s_ck the giant rubber phallus filling his mouth.
“There, that should keep you quiet,” she said as she took her seat again.
I giggled to watch Bob paralyzed with confusion and fear, fumbling around awkwardly trying to undo the strap. With his arms over his head, his dress was pulled upwards and Barb took advantage of his distraction by tugging his nursery print plastic panties down around his skinny legs, lowering them until they were gathered around his ankles. My husband was too occupied with his gag to do anything more than offer token resistance to Barb’s efforts and without warning, she suddenly yanked him over her lap. He squealed again like a little girl and I knew I was going to thoroughly enjoy this.
Like an expert, Barb removed the pins securing both sides of his diaper and pulled the thick cloth back between his legs, exposing his pale, round buns. Thus exposed, she wasted no time in swinging the wooden paddle down with a loud, harsh slap that filled the room like a thunderclap. Bob jerked convulsively and his eyes just about flew out of his head in shock and surprise. Howling from the sting, his right hand shot back to try and protect his defenseless bottom.
“Thank you,” Barb said with a smirk as she snatched his wrist with her left hand making Bob realize he’d been tricked.
Without waiting any further, Barb began spanking him in earnest, wielding the paddle with fierce, blistering swats. One cheek, then the next, then she mercilessly spanked both cheeks with punishing swats of the hard, unyielding wood on his soft, quivering flesh. Barely ten seconds into his punishment, Bob burst into tears, sobbing through the thick p_nis that was filling his mouth. At last, I felt I was getting some satisfaction for the pain and humiliation he had put me through.
Barb didn’t let up for an instant and his bottom quickly went from pink to red, to a flaming, cherry crimson.
SMACKK!! SMACKK!! THWACKK!!
Bob’s feet kicked wildly but they were tangled by his plastic panties around his ankles and he struggled in vain to escape his painful punishment. His face was wet with tears and he howled incoherently from behind his rubber gag. Barb slowed her pace only enough to be able to better take aim at the tender sides of his cheeks which has thus far, escaped the direct attention of her terrible paddle. Hard, biting slaps rained down on his unprotected fanny and he squirmed helplessly trying to avoid her next swat. Of course, with her holding his right hand firmly behind his back, there was no escape for him and his bottom suffered swat after stinging swat. Very soon, the curved sides of his soft buns had been blazed with the same kind of fiery inferno as the rest of his bottom and Barb returned her attention once more to the center.
SMACKK!! SMACKK!! THWACKK!!
Right in the center she landed three, especially harsh, punishing blows. This was certainly no fantasy spanking. He was getting everything he earned and then some! I couldn’t believe her stamina! She wielded that paddle like a professional racquetball player.
At last, she stopped and set her fearsome instrument down.
Reaching forward, she unbuckled the gag and pulled the fat, saliva covered rubber p_nis from Bob’s gasping mouth. With it removed, we could clearly hear his anguished sobs that were racking his body. Draped over her lap, his dress gathered around his chest and his diapers pulled back, he looked like a naughty toddler and he bawled like a baby. Barb released her clutch of his right wrist but he was completely defeated and in no mood to fight anymore.
“Well my little sissy masturbator—have you learned your lesson today?” she said in a smug, superior tone.
“Y-yes—yes M-ma’am,” he blubbered between sobs.
“You see that Heather? That’s the kind of spanking you need to give him when he misbehaves. I don’t stop until his butt is blazing red, he’s crying like a baby, and he’s ready to apologize.”
She emphasized her point by smacking him soundly once more across both blazing cheeks.
I nodded my head in agreement as Bob howled out anew, a fresh torrent of tears streaming down his face as he slapped the floor in pain and frustration.
“And now, its time to take care of your little sissy’s masturbating problem,” she said as she stood Bob back up on his shaking feet. He teetered uncertainly, his shoulders still shaking as he cried openly, his face beet red with shame.
Reaching back into her bag, Barb brought out a small, clear plastic device that I didn’t recognize.
“Know what this is?” she asked me as she held it our proudly.
I shook my head not knowing but Bob gazed at it through his tear-filled eyes and he backed up uncertainly.
“Yes, I can see that you do, bedwetter-boy,” she said, a sly grin on her face.
Bob had been making an attempt to hide his privates by holding his diaper in front of him but Barb suddenly snatched it away.
“Your masturbating days are over, sissy Bobby,” she hissed as she removed a large clear ring from the device and opened it up by spreading the device apart.
“Put your hands behind your back,” she ordered him harshly.
Still sniffling and whimpering, he meekly complied and she slipped the ring behind his ball sack to close it up snugly in place. She slipped a small pin behind and through the top of the ring and then brought the other half of the device up to mate with the ring. Intrigued, I stepped closer to see what it was that she was putting on my husband’s unimpressive genitals. Barb deftly slipped Bob’s shriveled p_nis into the stubby, clear plastic tube that was shaped like a coc-k but far too short to allow any kind of erection to be achieved. In addition, I could see now that it was deliberately angled downward to make it impossible for his p_nis to rise up when aroused.
There were three pins that acted to mate the tube with the ring and Barb fit the pieces together closely, showing the precision of the ingenious device.
“This is a CB-3000 chastity device,” she informed me, “It prevents naughty boys like Bob here from being able to get a hard-on or being able to play with themselves. And with this lock, only you will decide when, and if, he should get some relief.”
She inserted a small lock into the extended tip of the pin and snapped it shut with finality. Bob sniveled and wiped the tears from his face as he gazed down in distress and disbelief at what was happening to him.
“There, that should keep you out of trouble from now on,” she told him.
Walking over, I grasped the strange device and tugged at it, intrigued by the cleverness of it. And I could see that because of its design, Bob would have no problem wearing it under his normal street clothes so there’d be no need to remove it when he went to work.
“Go ahead Sissy,” Barb teased him as she suppressed a giggle, “see if you can get your little p_nis free.”
Fearing the very real possibility that he might never be able to masturbate again, Bob tore at it with a vengeance, tugging and pulling and doing everything he could to extricate his poor captive wiener. It didn’t take long to realize that he was trapped and trapped good. Short of the key (or a powerful saw), there was no way he’d be able to escape from this fiendish device. He whimpered pitifully as he saw the futility of it all but the physical movements had also conspired to make his di_k swell involuntarily. It soon grew to the limits of the plastic tube which was very little before it filled it completely and was prevented from any further expansion. Feeling this new form of discomfort, he clawed again at it desperately, unable to perform what was previously a basic function and his frustration mounted steadily.
Barb and I laughed and laughed as the awful truth settled over Bob like a funeral shroud.
“That’s right Sissy—your masturbating days are over. From now on, you’ll only c-um only when Heather allows you to.”
“I-it’s not fair!” he quailed as his voice came close to breaking.
Barb merely laughed at him but I slapped him hard across his tear-stained pitiful face.
“I’ll decide what’s fair and what isn’t, you little pansy.”
“I hope your last little masturbation session was a good one, because it’ll have to last you quite a while,” Barb told him.
“How long should I make him wait?” I asked, suddenly intrigued by the power she’d given me.
“I’d recommend a minimum of at least three to four months without any relief. That way he gets used to the idea of no longer being able to play with himself and it breaks the addiction he’s under now.”
“No relief at all?” I asked, trying to imagine what that would be like for him. It was a devastating sentence, but one which I was only to happy to apply.
“Perhaps a milking once a month, just to relieve the pressure of built up semen in his balls. You can do that simply by humping him with a good strap-on, or using a d_ldo by hand—I can show you how when the time is ready.”
“But won’t he get an orgasm if I do that?”
“Oh no---don’t worry about that. His chastity device will stay on the whole time. He’ll leak a fair amount of semen but he’ll never get the explosive relief of an orgasm that he craves so badly. There won’t be any satisfaction and it’ll actually leave him even more horny and frustrated than before.”
“Wow—I like the sound of this,” I said enthusiastically.
“Most wives and girlfriends only regret that they didn’t take this step long before. And it’s the perfect solution for little sissies like Bob here who can’t stop masturbating. Now he can look at all the porn in the world and it won’t do him a bit of good. In fact, it’ll only make him more frustrated than ever!”
I clapped my hands with glee.
“This is the best thing that has ever happened to us! Okay—how long should I make him wait after the initial four month period of denial?”
‘That’s up to you. Some women go for once a month…and some don’t let their husbands ever experience another orgasm again.”
I eyed Bob who was standing there with his head hung in defeat, no doubt soberly contemplating a life without masturbation or self gratification. It would serve him right if I were to forever deny him another orgasm.
“Hmm, I’ll have to give that further thought…
“Okay Baby Bobby—it’s been a long day for you and now its beddie-bye time. Lets get your diapers back on and you can say nightey-night to our guest.”
Bob pouted as I sat him down on his diaper that was waiting on the floor. He winced and fought back several tears as his inflamed bottom came into contact with the cloth but I wasn’t concerned. After a quick shake of baby powder, I pulled up the front and pinned the sides together snugly which again caused him to whimper in pain.
“I’ve decided that from now on—you’ll put your diapers and baby clothes on the minute you get home from work. It’ll help to serve as a reminder to you of when I used to let you get away with masturbating in them.”
“Excellent idea, Heather,” Barb commended me, “It will also serve to keep him constantly horny, long after this humiliating night is over.”
“My thoughts exactly,” I said as I pulled his pink plastic baby panties up his legs, “Just think Bobby--this is what you’ve always wanted—to wear your sissy baby clothes around the house without restriction. And now you can do it every day—you just won’t be able to masturbate in them anymore.”
Barb and I giggled at Bob’s predicament as he squirmed uncomfortably in embarrassment.
Standing him up, I slapped him on his thick, diapered butt which made a characteristic thud but caused him to yelp in anguish from his recent spanking.
“Go and give Aunt Barb a hug and thank her for her wonderful gift, Bobby,” I instructed him.
He was obviously in no mood to thank the person who had just paddled him so severely, to say nothing of the loss of access to his p_nis, but he had little choice. Waddling over to where Barb was standing, he embraced her stiffly and without affection.
“Thank you for the gift,” he mumbled dejectedly.
Barb grinned broadly and hugged him tightly, her hand dropping down to pat his well padded bottom in a sign of maternal superiority.
“I’m so glad you liked it! I think you’ll agree that it’s just what all sissies who can’t stop masturbating need—don’t you think?”
Bob said nothing until I prodded him in the ribs.
“Yes, Ma’am,” he replied gloomily.
“Good,” I said with a smirk. “Now give Aunt Barb a kiss and then it’s off to beddie-bye for you Baby,”
For a moment, Bob did nothing but then as Barb bent down, he blushed with embarrassment as she kissed him full on the lips, making him feel all the more like a helpless little infant. He squealed like a five year-old while she held him, forcing him to submit to her vastly stronger will. Releasing him, she spun him around like a child and slapped his bottom, sending him stumbling forward awkwardly.
“Yes, run along to bed now Bobby,” she said curtly dismissing him, “your mommy and I have much to discuss...”
THE END
� Betty Pearl's Sissy Stories 20.1
Topic: A Sissy Gets Punished (Read 85567 times)
