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 dont pretend to understand it but I have grudgingly tolerated it, so long as he does it when Im not around. However, that doesnt 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 shed 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.
Dont 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 cant fathom why Heather puts up with a sniveling sissy like you who likes to play with his penis. 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 sucking 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 were 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, Its going to hurt like hell and before Im done, youll 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 Id make him prance around in front of this stranger and thatd 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 ˜Maam”is that understood?
Ye-yes Maam, he replied quickly, his voice shaking with fear.
Good. I enjoy making bedwetters and masturbators cry and I can see that youre both. Are you getting scared, little boy?
P-please dont do this, Maam, he quaked.
Barb slapped the palm of her slim open hand with the paddle which sent a shiver through Bob.
You look like youre 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 Maam, he mumbled miserably.
Im 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 Ill see to it you get what youve got coming. Feel free to kick your feet and cry your little eyes out”most little sissies do.
Bobs lower lip was trembling nervously and he looked very much like a frightened little boy, caught by his mommy. I could see that Barbs force of personality was enough to cow him completely without even laying a finger on him.
Okay Mr. pantywaist”its 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 cant have you howling and bawling at the top of your lungs. Therefore, Ive brought a little something to keep you quiet while I settle accounts on your bottom.
She produced a large penis shaped gag that had a strap on either side and a buckle at one end. Standing up, she positioned the blunt end of the cock at Bobs lips.
Open up, Sissy, heres a nice big cock for you to suck on while Im blistering your bottom.
No”no-- he backed away and whimpered but Barb was too quick for him. With lightning movements, she shoved the rubber penis past his protesting lips and immediately ducked behind him to secure the straps in the buckle. Bobs eyes widened in panic and he squealed loudly through the fat cock 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 Bobs protests came out only as weak incoherent whimperings as he was forced to suck 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 Barbs 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 hed 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 penis 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 didnt let up for an instant and his bottom quickly went from pink to red, to a flaming, cherry crimson.
SMACKK!! SMACKK!! THWACKK!!
Bobs 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 couldnt 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 penis from Bobs 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-maam, he blubbered between sobs.
You see that Heather? Thats the kind of spanking you need to give him when he misbehaves. I dont stop until his butt is blazing red, hes crying like a baby, and hes 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 sissys 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 didnt 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 husbands unimpressive genitals. Barb deftly slipped Bobs shriveled penis into the stubby, clear plastic tube that was shaped like a cock 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 penis 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 thered 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 penis 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 didnt take long to realize that he was trapped and trapped good. Short of the key (or a powerful saw), there was no way hed 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 dick 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.
Thats right Sissy”your masturbating days are over. From now on, youll only cum only when Heather allows you to.
I-its 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.
Ill decide whats fair and what isnt, you little pansy.
I hope your last little masturbation session was a good one, because itll have to last you quite a while, Barb told him.
How long should I make him wait? I asked, suddenly intrigued by the power shed given me.
Id 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 hes 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 dildo by hand”I can show you how when the time is ready.
But wont he get an orgasm if I do that?
Oh no---dont worry about that. His chastity device will stay on the whole time. Hell leak a fair amount of semen but hell never get the explosive relief of an orgasm that he craves so badly. There wont be any satisfaction and itll 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 didnt take this step long before. And its the perfect solution for little sissies like Bob here who cant stop masturbating. Now he can look at all the porn in the world and it wont do him a bit of good. In fact, itll 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?
˜Thats up to you. Some women go for once a month¦and some dont 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, Ill have to give that further thought¦
Okay Baby Bobby”its 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 wasnt 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.
Ive decided that from now on”youll put your diapers and baby clothes on the minute you get home from work. Itll 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 youve always wanted”to wear your sissy baby clothes around the house without restriction. And now you can do it every day”you just wont be able to masturbate in them anymore.
Barb and I giggled at Bobs 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 penis, 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.
Im so glad you liked it! I think youll agree that its just what all sissies who cant stop masturbating need”dont you think?
Bob said nothing until I prodded him in the ribs.
Yes, Maam, he replied gloomily.
Good, I said with a smirk. Now give Aunt Barb a kiss and then its 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...
Chapter Two
I thought I should report back on the wonderful success Ive enjoyed after placing my husband Bob, under strict chastity control. I took this extraordinary step four months ago due to Bobs compulsive masturbating problem. Ive used a CB-3000 chastity device on him in that time and its been nothing but a godsend, worth every penny I spent on it. With his little cock securely locked away, he can no longer play with himself and his orgasms are now solely controlled by me.
I owe a debt of gratitude to my good friend Barb, who got me started with this and shes been a constant mentor ever since. I even gave her the key to his lock for the first three months so that I wouldnt be tempted to give in to Bobs constant pleading and whining. However, truth be told, that behavior only lasted the first two weeks--after that, my usual response was to put him over my lap and give him a sound spanking.
Bob is required to wear his diapers and baby clothes when hes home from work and all day on the weekends. Oddly enough, this used to be a particular fantasy for him, but rest assured”its now his constant, bitter companion, ensuring he stays perpetually horny and frustrated. Before I put him into chastity, hed masturbate with his diapers on and then once hed gotten his rocks off”hed take the embarrassing, childish outfits off. Now, he never gets his rocks off and the baby clothes stay on. I couldnt have thought of a better way to make sure he was constantly teased if Id hired a full time stripper!
I dont require him to use his diapers for their intended purpose, unless Im angry with him for some reason. Under those circumstances, its not unusual for me to make him go for several hours before I change his wet diapers for him. I dont feel any sympathy for his situation, since this was his perverted fantasy in the beginning. Granted, back then, he was able to play with himself freely, whereas now he cant even touch his penis at all, but thats his problem, not mine.
A few of my other girlfriends have seen how I treat Bob (I call him Bobby now) and its always a terrible source of embarrassment for him to be seen by one of them. They have no pity for him either and they delight in teasing him mercilessly. They also have my permission to spank him if hes been rude to them and some have taken me up on it with great vigor. Poor Bobbys spent a number of afternoons with his nose pressed into the corner while his bottom blazes from a stinging spanking at one of their hands. Most of them are quite eager to see how far they can push him and he knows better now than to argue with them.
My mother also knows how I treat Bobby and shes been right on board the whole way. She never thought much of him from the very first time we started dating”telling me he was nothing but an immature sissy--so I guess she had seen this coming. When I informed her Id put him into chastity and diapers”she felt vindicated and she said it was entirely appropriate.
In any event, he spends at least one day on the weekends over at her place, cleaning and doing chores while dressed like an oversized toddler. She insists that the bathroom is to be strictly off limits to him and she usually begins his day by giving him a long, hot soapy enema. After he releases that in the toilet, the door is locked from the outside and anything else that needs to do get done, gets done in his diapers. That means hes usually wearing a very wet diaper by the end of the day. He knows he wont get changed until his assigned chores are completed so hes motivated to get them done as quickly as possible. However, even under the best of circumstances, this usually takes him about six hours so hes often quite wet and eager to be changed. However, my mom doesnt tolerate any sloppiness on his part and any chores that havent been completed to her satisfaction result in an immediate trip over her lap for correction. Shes a very determined spanker and she can reduce him to tears in less time than it takes to read this sentence. To make matters worse, this is all the more painful for Bobby when his bottom has been wrapped in the clammy confines of his wet diapers for several hours.
Full time chastity has been very hard for Bobby, although perhaps its more accurate to say that its been very difficult for him, not being able to be hard! Its been four arduously long months since hes had an erection and I know the lack of orgasms has been murder for him to endure. He went from masturbating freely to three orgasms a day, to zero for the last 120 days so its been a real ordeal for him. This has left him constantly frustrated and edgy, sometimes resulting in bouts of crabby moodiness. However, once again, Ive found the wooden paddle to be my best friend”I simply pull Bobby over my lap, pull his diapers down, and blister his bottom until hes compliant and ready to be my perfect little boy again. After reducing him to tears, he never fails to come around to my way of looking at things.
I simply love it”between the chastity, diapers, and regular use of the paddle”I win all the arguments!
Still, its not a completely dry existence for him since Ive started milking him once every month.
Barb and I went out and bought a sturdy strap-on dildo that Ive gotten quite a bit of use from. She recommended that I find the fattest one I thought hed be able to take and then get the next size larger. She said a sissy can always take a bigger cock than either you or they think they can. The first day I put it on, he nearly fainted with fright. Even after getting him stretched out beforehand with a thick buttplug, Bobby squealed and howled when I first thrust it into his pouting bottom.
I gave him a good long session with it, wearing him down until he was a quivering mass of emasculated sissiness. Afterwards, I found a large wet spot in the front of his diapers where the pre-cum had leaked through so I knew I had accomplished my mission. And true to Barbs word, the poor little sissy was still desperately horny afterwards, having been deprived of a powerful orgasm even though his juices had been milked completely.
Of course, since his cock was locked away, that didnt mean there was any reason I had to be without one. The strap-on worked admirably once again, this time secured around Bobbys hips. He looked comical with this giant dildo strapped over his fat diapers and plastic panties but it was wonderful for me to be filled for once with such a magnificent cock. Bobby had never amounted to much in that department and after enjoying this monster, I was determined never to let him put his own little penis inside me again. And it was the height of frustration for Bobby because he was using his own movements to make love to me, even though his own tiny dick couldnt feel a thing. As I was treated to orgasm after shattering orgasm, poor Bobby had to keep pumping away, hoping in vain for some kind of relief that would never come.
I particularly enjoy riding on top, where he can see my big breasts hanging over his face. They jiggle and sway within the confines of my bra, just inches from his face, which has the poor sissy beside himself with lust. I no longer let him touch them although hes free to stare and drool at them. This makes him nearly cry from the frustration of not being able to cum, which delights me to no end.
Ive also found the strap-on to be quite useful for obedience training.
Bobbys always been very sensitive about appearing as anything but heterosexual. However, now that I have a nice big cock of my own, I enjoy making him get on his knees before me, to suck it like a horny slut. He makes quite a sight, his lips wrapped around such a beast, and his cheeks spread wide trying to accommodate the mammoth shaft. He slobbers helplessly as I make him take it in as far into his throat as possible. I take my sweet time, making him practice his technique, teasing him and telling him Im getting him ready for the real thing. Over the course of several months, Ive turned him into quite an accomplished cocksucker, forcing him to practice until its second nature for him. This is devastatingly humiliating for him and I find myself wondering more and more if maybe I should make him go down on one of my gay friends. It would certainly be interesting to see him shamefaced and embarrassed as hes forced to swallow a mouthful of cum¦
After four months of this torture, it was finally time for Bobby to get his one, rationed orgasm. He had been counting the days and hours that whole last month and I dont think he slept a wink the night before.
On that fateful day, he was beside himself with excitement and he kept pestering me to find out by what method he was going to get it. I just told him hed have to wait, but early that evening, I told him to put on his most babyish outfit with his frilliest baby dress.
He was only too happy to comply, and when he emerged from the bedroom, I knew hed put a lot of thought into his ensemble. He was wearing cute pink barrettes in his hair which had been combed into two short pigtails giving him a decidedly little girl look. He had on his favorite pink and white baby dress, trimmed with miles of delicate eyelet lace. It had a very short hem (as do all of his dresses) so that his big, bulging diapers and plastic panties were clearly in view. He had picked out a frilly pair of soft ruffled rumba panties to wear over his diapers and knee high stockings with flouncy pink bows on the tops. Lastly, on his feet, he wore his glossy pink mary janes with their silver buckles.
Well, my little Miss Priss”dont you look spectacular tonight! I said brightly.
He blushed in embarrassment but I could also see he was tremendously excited and looking forward to the upcoming event. I had arranged to have some music playing in the living room and unknown to Bobby, Id invited a number of my girlfriends over to be entertained by the coming spectacle. The music had served to cover their arrival so my little sissy was still unawares.
Do you have the key? he asked breathlessly. He was already starting to pant and I smiled down at him with maternal patience.
No Babykins, grandmas got it, I said, using the nickname Id given to his strict, no-nonsense mother-in-law.
Bobbys face creased with doubt and disappointment.
B-but how am going to get released then? he asked worriedly.
Dont worry Sissy, Ive already invited her over to unlock your chastity device, just come into the living room.
He had an anxious expression on his face but it changed to open shock when he saw the handful of women waiting for him in our living room. They greeted him enthusiastically and he blushed furiously at the unexpected audience. Bobby was about to turn around and bolt for his bedroom when he glanced down and saw the Spencer paddle I was holding in my hand.
This is just so there wont be any trouble out of you tonight, Bobby, I told him, a tone of warning in my voice.
I scooped up Bobbys rubber cock pacifier and stuffed it in between his quivering lips, causing a ripple of laughter from the gathered women. Bobbys face was the color of a red apple as he sucked feverishly on the fat dildo in his mouth. He knew better than to spit out his pacifier once Id put it in but it also showed just how submissive hed become and he blushed even deeper.
He looks like a natural, one of my friends snickered.
Ill bet thats not the first cock hes sucked, commented another.
We should get John over here, suggested another, Ill bet hed love to have that big cock of his sucked dry by Bobby.
Looking around in a panic, Bobby appeared as if he were on the verge of tears.
Dont worry Bobby”theyre just teasing, I assured him, although Im not sure he believed me.
Mom”would you like to do the honors? I asked my mom who was standing nearby with a smirk of satisfaction on her face.
Okay, but this goes against my better judgment--I think your little sissy masturbator here should go another four months before hes allowed an orgasm, she opined as she bent down and began tugging his flimsy rumba panties down and off his fat, bulging diaper. Bobby was deeply humiliated but he stood there passively as my mom brought his panties down around his ankles, followed by his white plastic nursery baby panties. Putting her hands on his shoulders, she sat him down on a chair that had been placed in the center of the room.
While Bobby sat there in shameful silence, my mom unpinned his diapers and pulled them down in front, draping them over the front of the chair.
Not wet yet, I see, she commented dryly, how unusual.
The other girls giggled but now they leaned forward more closely to better see the CB-3000 he was wearing that was typically hidden within his diapers.
Removing the key from her purse, mom inserted it into the small padlock on the front of Bobbys chastity device and unlocked it, taking the lock and putting it aside. Grasping the clear cock tube portion, she gently jiggled it free and lifted it away, exposing Bobbys shriveled penis that was clearly affected by his present embarrassing circumstances. With a few more movements, my mom had removed the cuff ring and freed his captive wiener.
Despite the stares of all those around him, Bobby was very intrigued by what was happening and I sprinkled a generous amount of fragrant baby powder on his rising erection. Before long, it had reached its glorious full length of two and a half inches which caused another round of chuckles from the gathered guests. Pulling his diaper back up, we pinned it snugly in place and followed that with his nursery print plastic panties.
He was about to reach down and pull up his rumba panties when my mom put the toe of her shoe across them, holding them in place around his ankles.
No”leave them down there”I think it makes you look like a naughty little girl, she smirked.
Bobby couldnt say anything with the pacifier in his mouth and he was clearly confused by what was going on.
Okay Bobby, I told him as I put my hands on my hips and looked down at him, Were going to give you the opportunity to do what it was that got you in trouble in the first place”except this time, you wont get paddled. Heres a porno mag you can use to whack off with. Ill put it on the floor here so you can imagine youre with one of these slutty women in it.
I placed the magazine down on the floor in front of him and spread it open to a section that contained a number of glossy photos of scantily-clad women with impossibly big breasts.
Bobby looked around uncertainly, not sure what to do.
Go ahead, Sissy, I prompted him, Do what comes natural--you know you want to.
He shook his head, the angst written all over his face, unwilling to humiliate himself even further in front of all these women. I waited a moment, but then when it was clear he was too ashamed to perform for us, I decided to up the ante.
Of course, if youd like, I can follow grandmas advice and simply lock your naughty little penis back up for another four months¦
Bobby shook his head in a panic, seeing his options now being reduced to the lesser of two evils.
Then youd better get started, I told him, Im going to give you three minutes to get your little deed done¦starting¦now!
Bobbys eyes went as wide as saucers as he realized he was up against a time limit now. There was no chance to debate the matter”he had to either start masturbating in front of everyone or hed have to go without cumming for who knows how long.
In two minutes and fifty seconds, Im going to pull your diapers down and put your chastity device back on, whether youve cum or not, I informed him as the others giggled merrily.
Bobby lost no further time in waiting. His hands shot down to the front of his plastic covered diapers and began stroking furiously, hoping to be able to beat the clock. As he did, my friends began noisily taunting him, encouraging him like it was an Olympic race. This only further distracted him and I could tell he was having difficulty doing what would have been easy any other time. Rubbing and fondling the crinkly vinyl crotch of his diapers, he tried to close his eyes and ears to the humiliating catcalls surrounding him and concentrate on what he was trying to do.
One minute, twenty seconds, I announced out to more giggles.
Several of the girls took their cell phones out and began taking snapshots at the hapless sissy shamelessly playing with himself before them. Here was a grown man, wearing a pink dress and diapers, mary janes and sissy socks, masturbating openly while his rumba panties were tangled around his ankles. It was beyond comical”it was freaking hilarious!
Opening his eyes again, he looked out at the cackling women surrounding him, calling out condescending comments that only served to further inhibit his efforts and cause him more difficulty. Bobbys face was red with concentration and a bead of sweat trickled down the side of his forehead while all around him, the girls snapped more shots and made fun of him.
Fifteen seconds left”youd better hurry Bobby! I called out above the ruckus filling the room.
His face contorted as he sought to reach that elusive pinnacle that under any other circumstances, he would have reached two minutes ago. Rubbing himself for all he was worth, Bobby masturbated as if the Devil himself were timing him. With his mouth filled with a big rubber cock, he breathed heavily through his nose as he stroked himself with self indulgent abandon.
Times up! I announced suddenly as the girls clapped their hands with glee and satisfaction.
Bobby kept rubbing himself but mom and I quickly wrestled his hands behind his back where she held them in place. Struggling desperately against her, Bobby squirmed and squealed, frantic to achieve his one promised orgasm but my mom was far too strong for him.
Sorry Sissy, she said unsympathetically as she gripped his wrists tightly from behind him, looks like youll just have to try harder next time.
Bobby was on the verge of panic and a tear trickled down the side of his shocked face. I pulled his plastic panties down and unpinned his diapers, exposing his pulsating hard-on that was trying even now to get the necessary physical stimulation.
You had your chance, Bobby. It looks like youre not ready to have an orgasm yet, I said as I picked up the cuff ring of his CB. Bobby whimpered and was trying to plead with me but the rubber dildo in his mouth made everything incoherent to his listeners. He shook his head violently and blinked back a set of tears as he struggled fruitlessly against my mom.
Maybe another month or two of chastity will make you more eager next time, I said as I closed the cuff ring around the base of his genitals and slipped the pin through. Tears were coming down his cheeks now as I took the cock tube and pushed his unwilling penis into it. Without being able to rub it any more, his dick withered and began going limp, even as he flexed it, trying in vain to get his pending orgasm.
Poor little sissy, I consoled him as I mated the three pins together, mashing his penis in and closing the CB together, Looks like youve got another long, horny month ahead of you...or two.
As I slipped the lock through the end of the pin, I pushed it closed and smiled down at Bobby, his penis once more securely captive and impotent and his balls still swollen with unreleased cum.
Several of the girls came over and bent down to give him a kiss on his cheek, granting him a generous view down their tops as they did. Whimpering miserably, he stared desperately at their breasts as I re-pinned his diapers.
Stand up Sissy, I ordered him, so I can pull your plastic panties up.
Meek as always, he did as he was told, standing up while I pulled and tugged at his snug vinyl baby panties to get them over his fat diaper. Moving my thumbs around the inside of his elastic waistband, I worked them up and around, ensuring that none of the cloth was left exposed. He stood there sucking on his pacifier as I reached down and brought his frilly rumba panties up his legs, slipping them over his shiny baby pants.
Well, its Bobbys beddie-bye time, I announced to my friends, You guys dont have to go, but I have to tuck him in for the night.
The girls all waved him goodbye as if he were a child, some patting him on the head affectionately. He slurped noisily on his pacifier which had become well coated with his slobber while hed been masturbating. Hanging his head, he trudged down the hallway after me, me leading him by the hand.
I wasnt sure how long Id make him wait again for his next chance to cum, but I thought two months sounded good for a start. I was really starting to enjoy this power shift in our house, with me being in absolute control over my sissy husband.
It was time now to consider the next steps in my domination over him.
Chapter Three
It had been five months now since Bobby had been allowed to cum and hed finally become accustomed to not being able to masturbate. That doesnt mean he was happy with the situation”he wasnt. He desperately missed the old days of being able to pleasure himself whenever he wanted to, instead of being controlled by me, his strict wife. But as far as Im concerned, thats just too bad”sissies in my house dont get to play with themselves, and they dont get to cum. What they do get”is harsh, unremitting discipline and daily doses of humiliation.
I could see that he was leaking pre-cum almost constantly now, leaving a telltale gooey spot in his diapers, the only exception being when he got his once-a-month milking. He found the experience to be maddeningly frustrating because I did my best to tease him while I slowly massaged his prostate with the Aneros dildo tool. I usually dressed in a something very low cut, as I know he loves to gaze at my big breasts and imagine Ill let him touch them again. Of course, the only part of my body I let him touch any more is my pussy, and thats only with his tongue. Its simply amazing how skilled a man becomes at oral sex when hes been deprived of his orgasms!
Anyway, I was starting to think that maybe I should allow Bobby a chance to earn an occasional orgasm, so long as it was a rare and done in a manner I approved of. After all, I didnt want him to forget what they were like”and the memories would serve to torture him during the times in between.
I told him that if he could get through one of my spankings like a real man”Id grant him a wonderful orgasm. I made it very clear though, that I meant I would tolerate no crying whatsoever. If he cried like a baby (which is his usual reaction), he wouldnt get to cum.
Knowing those rules, and knowing how hard it is for him to keep from crying, Bobby went two days before his horniness finally got the better of him.
Mommy? he asked one evening before his 8 pm bedtime.
I was sitting in the study, quietly reading a magazine when I looked up to see him with a look of mixed feelings on his face. My husband was wearing one of his usual baby outfits, a pastel blue gingham dress that showed off his thick diapers and plastic panties.
Yes, Bobby, what is it?
Um, I was wondering¦ he began uncertainly, You remember the offer you gave me about cumming the other day?
I set my magazine down and looked him squarely in the eye.
Yes, I do.
Um, well, I was sort of wondering¦ he stammered shyly, Do you think we could try it tonight?
Are you ready to try and take a spanking? I asked him evenly.
Uh-huh, he said, ashamed to have to ask his wife for such a humiliating method in order to be able to be released from his chastity device.
Very well. I want you to ask me for it, I told him.
Bobbys face reddened and he stared at the floor, trying to find the courage to say the words. I know he hates it when I go out of my way to humiliate him but theres absolutely nothing he can do about it.
He paused and licked his dry lips before tentatively beginning.
M-Mommy? Will you please give me a spa-spanking? he quivered.
Yes I will Sweety, I told him nicely, Go and fetch your paddle and meet me back in here.
He shuffled off to get the dreaded Spencer paddle that I use to discipline him with, while I took a seat in a straight backed chair.
When he got back, I was ready, my short skirt pulled back and my high heeled feet placed slightly apart to take him over my lap.
P-please”please dont spank me hard, he whimpered pathetically, the fear showing in his voice.
Youll get the same spanking you get every time you go over my lap, I told him sternly, without a trace of sympathy.
I think he was having second thoughts about this”he probably suspected Id give him only a moderate spanking so hed have an even chance of taking it without crying”but I had no such intentions. He was going to get every slap of the paddle, and as hard as always, as he did when he needed to be punished for a real offence.
Before he had the chance to change his mind and back out of it, I tugged his plastic panties down off his diapers and past his knees.
Over mommys lap, I told him sternly as I took his wrist and pulled him over.
He squealed in fear and repeated his earlier request.
Please Mommy, please dont spank me hard”I want to c-m tonight! he whined.
If you start acting like a man”maybe youll get to, I admonished him as I unpinned his bulky diapers and pulled them back between his twitching legs.
Rubbing his smooth buns with the paddle, I brought his attention to the large mirror on the opposite wall.
Bobby, I want you to look up in the mirror so I can see your face. If I see any tears, youre chastity device stays on. Understand me?
Ye-yes Mommy, he quailed.
With that, I wound up and brought the paddle down harshly, searing his bottom with the full impact of the hard oak and flattening his cheeks painfully, however briefly. It was a loud, crisp smack and it filled the room, even as Bobby howled out in reply. Looking at his face, I could see him gritting his teeth, desperately trying to maintain his composure. I smiled briefly at him, then gave him another resounding slap, right where the delicious curve of his bottom reached the top of his thighs. He kicked his feet wildly and cried out again, but came short of actually crying.
Youll notice I left the window open Bobby, I said, pointing with my face at the curtains swaying in the evening breeze, So you can be assured the neighbors will know youre getting punished tonight.
I saw the look of panic cross his face and I smirked at his embarrassing plight. Then I delivered two, well placed swats, one on each cheek. He seemed to think I would stop with each one so just to throw him off balance, I brought the paddle back down again, extra hard across both his buns.
OW! OW! OW-WOW-WOW!! he hollered and he bunched his fists together, beating them on the floor as he struggled mightily to keep from crying.
Look in the mirror, Bobby, I commanded him as I held the fierce paddle over my head.
Down it swooped again to land squarely on his reddening rump.
SMACKKK!!
That was the straw that broke the camels back. Like a dam bursting, Bobby burst into tears and began sobbing uncontrollably like a baby. Once again, I had succeeded in breaking him and I wasnt about to stop there. I continued the spanking, swatting his defenseless cheeks with unrestrained enthusiasm. Even though Bobby had been a perfect little boy over the last week, I felt a good hard spanking would help to show him who the boss was--and always would be, in this house. That--and I feel a good cry is good for a sissy from time to time.
He bawled and banged his fists on the floor as I continued swatting and slapping his blazing bottom with the cruel paddle. I knew the neighbors fully approved of the way I disciplined Bobby and his cries, mixed with the sound of the hard, unforgiving oak landing on his bottom would be like music to their ears.
Looking in the mirror, I could see his face was wet with tears, a clear cut case of his defeat if ever that was one. At last, I stopped and set the paddle down. His loud sobbing filled the room as I pulled his diapers back up and pinned them into place.
There, There, Baby, I said as I helped him to his feet, Mommys all done now.
I pulled his plastic baby pants up his shaking legs as he cried unashamedly before me.
Standing up, I tugged his panties up and over his bulging diapers, effectively sealing the inferno inside so hed be forced to endure the heat while he lay in his crib.
There, there, Little Baby, I consoled him as I drew him over and put his head against my full bosom, You didnt quite make it that time, but theres always next time.
His shoulders shook as he sobbed at the thought of never getting to cum. I knew it was all the worse for him as he pressed his face against my breasts, staring hard at my deep cleavage.
And now its beddie“bye time for my little Sugarplum, I told him, Go brush your teeth and Ill meet you in your nursery with a warm bottle of milk.
Still crying, he blubbered a ˜yes mommy and waddled off down the hall as he rubbed his blistered bubble-shaped bottom.
Chapter Four
By now, Bobby had become used to my unquestioned authority over him and he knew that any disobedience on his part would be met with swift and immediate punishment. I found that enforced chastity was also making him more compliant and submissive to me and arguments between us were now a thing of the past as he was forced to defer to me in any and all matters of consequence.
Despite my offer to allow him to c-m if he could get through a spanking without crying, he still hadnt succeeded and with the exception of his monthly milkings (which only left him more horny and frustrated than ever), he hadnt experienced an orgasm since I first caught him masturbating to porn on our computer, six months ago. To be sure, life was a torture for him, having to wear soft diapers and frilly baby clothes nearly all the time but not getting any relief for his constant, gnawing horniness. For my part, I enjoyed teasing him as much as possible, wearing small, sexy tops that showed my big breasts to great advantage and short skirts to showcase my legs. Often, Id see Bobby staring at my cleavage or drooling at my high heels, lusting after something he could never have.
After several months of going without real sex myself, I decided that I should start dating again, since being married to a diaper-dependant sissy isnt exactly my idea of a sexual fantasy. I was totally up front with Bobby about it, telling him that women have sexual needs that simply cant be ignored. Its just not the same for sissies who wear diapers”they dont need orgasms like real men do, I explained to him.
Of course, the first time I informed him of my plans, he threw a tizzy fit and began shouting at me like a cranky five year-old. And I, like any responsible mother, responded by taking his diapers down and pulling him over my lap to soundly paddle his sissy bottom. And just to make sure thered be no more trouble from him, I called Barb over to baby sit him while I was gone. She showed up while I finished getting ready and I explained his rules to her.
He gets his diapers changed at 7:45 and a bottle of warm milk before he has to get ready for bedtime. Make sure he brushes his teeth and then put him down in his crib because at 8 pm sharp, the lights go out in his nursery.
If he whines or complains, just take him over your knee and paddle him until he learns his lesson.
Also, please let me know if he misbehaves so I can discipline him in the morning myself, I finished.
Bobby pouted angrily as I explained his restrictions to Barb but he knew better than to disobey her”he was all too familiar with her formidable spanking arm.
Barb thoroughly agreed with my decision and she thoughtfully reminded me to remove my wedding ring before I went out”something I almost overlooked!
Dressed the way I was, in a slinky black dress with a plunging neckline and stiletto heels, I got plenty of attention at the club where I met my friends. I danced with several good looking men and then late that night, I met Hank, a tall, solid built guy who worked in the lumber industry. What a change it was to have his big, muscular arms holding me tightly as we danced. On one slow number, I felt his massive erection pressing against me and I blushed as I imagined him using it to satisfy me. What a difference that would be from my own pathetically endowed husband!
I gave him a long slow kiss to make sure he was clear of my interest and he was delighted to get my cell phone number before we parted for the night.
I was floating on air when I finally got back home that night. Barb was reading a book and she asked how everything went. After I excitedly told her about Hank, I asked how Bobby had been.
He pouted and cried a little bit after you left”˜kept whining that it wasnt fair and everything¦so I decided to give him a nice, hot soapy enema before bedtime and that really took the wind out of his sails, she giggled. By the time he finally finished releasing it, it was about 7:30 so I just decided to put him to bed early. He pouted some more while I put him in his nighttime diapers”he had wet himself earlier--and then I gave him his bottle while I was tucking him into the crib.
And I havent heard a peep from him all night, she finished, clearly pleased with her work.
I thanked Barb profusely for her help and she assured me shed be happy to do it again in the future so I could be free to date Hank.
That was a month ago and since then, Ive been to bed with Hank at least twice each week. To my delight, I found out that he is as well endowed as he is good looking and I swore I was going to be split in two the first time we had sex. I lost track of how many orgasms I had that night and I never realized that sex could be so fulfilling. Unlike my husband, who would quickly cum within the first two minutes only to leave me high and dry, Hank had tremendous staying power and he pounded me until I was sore but satisfied.
Bobby soon found out about Hank but there was nothing he could do about it. I told him I was going to continue to date other men and that was that. He could either put up with it or leave (without the key to his chastity device, of course). And on those nights that I went out, Barb was only too happy to treat his moodiness with a hard spanking or a lengthy enema, so he had little choice in the matter.
After a while, I decided to involve him in my dating to a small degree”I allowed him to pick out my outfit for the evening and brush my hair while I put my make-up on. He was so worked up from not being able to cum that he was desperate just to see me in my lingerie while I dressed for my date. Often, he would cry with frustration as I adjusted my bra in the mirror or put another coat of wine colored lipstick to my lips.
Just remember Bobby”you are the one who chose diapers and baby clothes instead of regular sex, I liked to tell him.
And always it was the same with him¦when would I allow him to cum again or when would I allow him to be a proper husband¦
Sissies dont need to cum, Id tell him and hed run from the room in a childish huff befitting his status.
One night, after another wonderful date, I was feeling a little tipsy and I asked Hank to come home with me. It was very late and Barb was already asleep on the couch when we stumbled in. I put my finger to my lips to quiet Hank and then pulled him by the hand down the hall. Opening Bobbys nursery door as silently as possible, we entered as softly as cats and I brought him over to see my husband blissfully asleep in his crib. I stifled a giggle as I saw him lying prone, the baby blankets tangled around his waist and his thumb in his mouth like a little baby. His shiny plastic panties were thus exposed and the moonlight coming through the window reflected off his bubble shaped bottom. Reaching down, I slipped a finger under the elastic leg opening of his baby pants and felt the cool wetness of his diapers”they were soaked as usual.
With a sharp slap on his bottom, I woke up my sissy husband who sat up with a start. He was shocked and surprised to see me with the large, hunky man next to me and he tried unsuccessfully to cover himself with his baby blankets which only caused us both to laugh out loud. Barb had put Bobby into a short pink and white nightey with puffy sleeves and a lace collar and he looked like a little toddler girl trying to hide from monsters that had come out from his closet. Around his neck was his rubber c-ck-shaped pacifier and I quickly stuffed it into his mouth as Hank snickered down at him.
Even though it was still semi-dark in the room, I knew Bobby was blushing furiously, unable to explain why he was wearing diapers, a pink nightey, and sleeping in a babys crib.
Looks like mommys little sissy wet his diapers again, I observed as I tried to keep from laughing.
He stared back at me, his eyes pleading as he looked nervously at Hank and then back to me.
But then, I guess thats all your little wee-wee is good for, isnt it? I said tauntingly.
Would you like to see a real cock? I asked him rhetorically, since I knew he couldnt say anything with the fat dildo filling his mouth.
Hank here, has a monster that would shame even the rubber one youre sucking right now, I told him.
The drinks Id had were making me feel naughty and a little bitchey so I decided to push Bobby some more. Reaching down, I unzipped Hanks pants and slowly pulled them down, teasing Bobby with a sexual act he could only dream of. Sliding my long nails inside his boxers, I pulled them down Hanks huge thighs and looked over at Bobby. He was fascinated by my new boyfriends massive organ, even though it was still quite flaccid. Even limp, Hank was longer than Bobbys was, even when he was erect.
Getting on my knees, I slowly took his cock in my mouth, making sure Bobby could see every detail. He clung desperately to his crib bars as he watched in frustration as Hank grew harder, his big cock quickly filling my mouth and stretching my cheeks out. Up and down, I deep throated Hank while he moaned deliriously with pleasure. Bobby sucked his own pacifier as his own little penis grew hard in the strict confines of his chastity device. I can always tell when his wiener is bearing painfully inside his tube because he starts pawing fruitlessly against the front his diapers, trying in futility to relieve the pressure.
I stopped Hanks blowjob long enough to stand up and lower the side bars of Bobbys crib, taking him by the hand and sitting him on the floor next to me.
Okay Bobby, youve had plenty of practice”its time you tried the real thing and put all that hard work to the test, I told him.
He looked at Hanks big boner that was glistening in the dim light and shook his head nervously.
Come on, I ordered him, You know that this is what all sissies love to do”have a nice big cock fill their mouth.
I grasped his pacifier and popped it out of his mouth as Hank positioned his hard-on before Bobbys face.
No Mommy”please-- he stammered fearfully but Hank abruptly shoved his cock into Bobbys mouth before he could finish his sentence.
Bobby squealed and gagged as Hank rammed his big monster deep into my husbands mouth. His eyes were as wide as saucers as he struggled to keep from choking, the big meaty tool stretching his cheeks to the limit.
There you go Bobby”show Hank just how talented you are when it comes to sucking cock, I giggled.
He struggled and squealed helplessly as Hank placed his big hands behind Bobbys head to guide him up and down his mammoth shaft. Saliva was dribbling down Bobbys chin as Hank drove his thick pole deep into his throat, forcing him to take every glorious inch of his organ. Bobby whimpered helplessly, too much of a wimp to try and stop Hank from humping his mouth.
I was absolutely loving it and it was a big turn-on watching Bobby get so completely humiliated.
Soon, Hanks big balls were slapping Bobby on the chin and I could hear his breathing growing heavier.
Before long, he began jack hammering Bobbys mouth with hard, quick thrusts, until he stopped suddenly and paused, holding it about halfway out.
Bobbys eyes quickly went wide again as Hank bellowed out a groan and blew his thick, creamy load into the sissys mouth.
Finally, Bobby was getting what he really deserved. I also knew this was exactly what he needed to put him in his proper place.
Just do what comes naturally and swallow, Bobby, I whispered into his ear.
Dutifully, he gulped it down, only to be rewarded with another huge, sticky ejaculation being forcefully pumped into his mouth. Bobby squealed again and cum began dribbling down his chin as he struggled to keep up with the fire hose filling his mouth. Hank pulled out just enough to let him swallow again before driving his beast back into Bobbys mouth and blasting another creamy load deep down his throat.
Finally, he pulled his cock out and left Bobby gasping, his lips covered with sticky jism as he fought to regain his breath.
Be a good a sissy now and clean his cock Bobby, I ordered him.
With a sob, Bobby did as he was told, licking Hanks massive shaft even as more cum bubbled up from the hole at the tip.
That was wonderful, I exclaimed gleefully as I quickly slipped out of the skirt I was wearing. Watching Bobby be humiliated by my new boyfriend had made me incredibly hot and now I needed some satisfaction of my own. Sitting down on the crib mattress, I peeled my G-string off and flung it aside.
Okay, Bobby--You know the routine¦its Mommys turn now.
I made him bring me to three orgasms before I finally changed his wet diapers and put him back to bed in his crib, horny and frustrated like never before.
That next morning, Hank and I slept late, relaxed and satisfied with our new arrangement. I also knew that Id finally found where a sissy like Bobby truly belonged”down on his knees with a big cock in his mouth servicing my boyfriends.
Chapter Five
Normal 0 MicrosoftInternetExplorer4 /* Style Definitions */ table.MsoNormalTable {mso-style-name 0; mso-tstyle-colband-size yes; mso-style-parent 0in 5.4pt 0in 5.4pt; mso-para-margin .0001pt; mso-pagination 10.0pt; font-family:"Times New Roman";} It had been six months now, since Bobby had enjoyed the pleasure of an ordinary orgasm. And to my surprise, I found that depriving him of such a basic function had caused him to become even more submissive to me, making him more pliable and obedient to my whims. It would seem that when a male is prevented from that most basic of manly functions; being able to get an erection, it tends to have a feminizing effect on him, making him more prissy and less argumentative. In short, he bends more easily to the superior female will. I took full advantage of the situation and expanded my domination over him, forcing more concessions from him and restricting his freedom even further.
For one thing, I was openly dating other men now, while I left him home in his diapers to be watched by the babysitter of my choice. And just to rub salt in the wound, I insisted that he help me get prepared for my dates, running my bath, styling my hair, and selecting my hottest lingerie for my liaisons. I required him to pick out my clothes, with the knowledge that if they weren't sexy and provocative enough, he could expect a trip over my knee before I left. Thus, poor Bobby had to endure the frustration of picking out my lowest cut tops and skirts, then watching as I put them on in the most teasing manner possible, all with the knowledge that my date would be the one enjoying the view later on while he spent another night, alone, horny and frustrated.
I intended for this evening to be similar, but I also had a wicked idea up my sleeve. Informing Bobby of my evening's plans, I told him to meet me in my bedroom.
He came in, wearing one of his prissy, flouncy dresses, one with a lot of layered petticoats that fluffed it up, but that still showed off his fat, embarrassing diapers. I, on the other hand, was dressed only in my sheer push-up bra and panties. Sitting on the edge of the bed, I commanded him to pick out some lingerie and an appropriate outfit for me to wear.
Bobby was clearly in a state of angst and agitation; beads of sweat appeared at his brow and he kept wrestling with the front of his diapers, obviously trying to relieve the painful strain he was feeling from his poor, throbbing penis, struggling within his chastity tube to get hard. He stared hungrily at my smooth breasts, the naked lust in his eyes plainly apparent. Being completely consumed with his horny impulses, he eventually selected a shimmery black corset that I knew drove him wild with desire. It added to my already hourglass shape but it also plumped my big breasts into two impressive feminine mounds. It wasn't uncommon for Bobby to start begging me for relief during these times and I couldn't really blame him--his shortness of breath and fidgeting showed me just how frantically desperate he was to cum.
"I have good news for you, Bobby," I told him as I carefully pulled one of my silky charcoal stockings up my toned legs.
"Tonight, you'll have a date just like me."
Bobby's face registered his shock at such an unexpected event and at first, he was at a loss for words.
"You-you mean I'm...I'm going out on a date too?" he asked incredulously.
"That's right Sissy, we're going to a private party and you'll be meeting my friend Dahlia."
What I didn't tell him was that it Mistress Dahlia, a very strict dom that was known for crushing sissies like flies.
"Oh, thank you Mommy!" he gushed, "Thank you for letting me come with you tonight."
I'm sure he thought there would be an opportunity for him to be released from his chastity but he knew better than to ask for it directly.
"Now, now, don't get too excited," I giggled, "help me get dressed first so we're not late."
He responded enthusiastically and picked out a plunging, low cut top and a nice short skirt to show off my long legs. Lastly, I had him put my high heeled sandals on, and he buckled the tiny straps that went around my ankles, like a good little submissive sissy.
After making some small changes to his own outfit and picking out some shiny Mary Janes, I sprayed him liberally with his sissy perfume, a little thing I picked up from MommyScents that makes him smell just like a baby's nursery. Now, even a blind man would know what an absolute sissy he was from the sweet, pungent scent he was bathed in.
After a short drive, we arrived at Dahlia's substantial house. I informed Bobby that my date would be along shortly and after being invited inside, we made our introduction to the party's host, a cute young woman named Laura.
What followed next, I can barely describe without falling over laughing.
Mistress Dahlia walked into the room next, strutting regally like a queen in her black leather bustier, panties, and thigh high boots. She had such a commanding presence that even I drew in my breath in appreciation. She was quite a striking woman, with long, jet black hair and dark, piercing eyes. Seeing the haughty, imperious expression o
Bobby greeted her with friendly naivet--which she ignored, staring down at him contemptuously only long enough to be satisfied that here was a sissy who needed to be shown his place. Reaching down, she snatched his wrist roughly and jerked him forward, simultaneously slapping his fat, diapered bottom with a resounding thud.
"Come along you little sissy," she snarled, yanking him into an adjoining room with her.
Bobby squealed in despair but was forced to stumble after her, to receive god only knew what might be waiting for him inside. The laughter of everyone present filled the room as we watched his retreating form being led firmly and purposefully by Mistress Dahlia to his fate.
While my host gave me a glass of wine, we listened for a moment, hearing Bobby's plaintive pleading, followed by what sounded like a hard slap being delivered to his face. More pathetic whining and pleading followed as my host and I shared knowing looks and giggles. A moment later, we could clearly hear the distinctive sounds of a sissy's bottom being soundly paddled. This was confirmed by Bobby's loud sobbing and wailing as Mistress Dahlia proceeded to blister his bare bottom with a vengeance.
I'm quite sure this wasn't the "date" he was expecting!
"Come with me," my host offered conspiratorially, "We have a special viewing room where we can watch as things get even more interesting."
Thoroughly intrigued, I followed her to the room next door, which had a large window into which we could view what was taking place between Bobby and Mistress Dahlia. It was explained that we were looking through a one way mirror and my sissy husband would be unaware of our watching him.
When we came in, I could see that his diapers had now been haphazardly pulled back up and Bobby was on his knees, kneeling submissively before Dahlia. She was wearing a sturdy strap-on with a thick, flesh colored dildo, driving it deep into Bobby's stretched mouth as he whimpered helplessly, the tears still spilling down his cheeks. She was holding his head firmly as she rammed the huge object as far as it would go down his throat, causing him to squeal like a defenseless little girl.
Then, from the other side of the room, I saw a big, rough looking biker come in, dressed in black leather and a jacket, his bare, barrel shaped chest, thick with hair. Coming over next to Bobby, the biker unzipped his pants, revealing a growing hard-on that was amazing in its tremendous size. Pulling Bobby off the dildo that was nearly choking him, he immediately shoved his own erection into the sissy's mouth, hardly giving him a chance to catch his breath before forcing him to suck on his massive, meaty tool. Bobby squealed again, but before long, his head was dutifully bobbing up and down while the biker guided him with his big hands behind the sissy's head.
We watched with glee as Dahlia lubed up her strap-on and then got down on her knees behind Bobby. Yanking his diapers back down, she positioned the blunt head of her dildo at Bobby's puckering back hole.
"Open wide, Bobby," she declared, "'cause I'm coming in!"
She pushed it forcefully against his sphincter, but the huge size and Bobby's desperate squirming combined to frustrate her efforts. His Mary Janes were twitching and we watched as he tried frantically to pinch his spanked, cherry red cheeks together to deny her access.
Bobby squealed and carried on but with his mouth full of the big biker's cock, he was hardly in a position to resist. Dahlia slapped his blazing buns viciously, making him buck and squeal anew. I saw a fresh set of tears trickle down his cheeks as he fought a losing battle with her determined, slippery dildo. Finally, she managed to push the fat head of her strap-on past his defeated sphincter and she rammed it home without mercy. Shoving it in until it bottomed out, she gripped his hips tightly and held it in place, forcing him to take every rubbery inch, a smug, wicked grin on her face. Her long nails dug into his soft hips and as she looked our way, she gave us a cocky wink. Bobby's eyes went wide in angst but now he was getting drilled from both ends and there was no escape for the weak-willed sissy.
Just when I thought it couldn't get any better, a second big biker came into the room.
The guy who was jack hammering Bobby's mouth, soon climaxed in a mighty roar that filled the room, to say nothing of the creamy load that was pumped down poor Bobby's throat. He made several desperate attempts to swallow the huge quantity of sticky semen that was being forced into his mouth but at last, with cum dribbling down his chin, the biker seemed to be satiated. When he finally pulled his tool out, my sissy husband was gasping for breath and gooey semen was seeping down his chin.
Nevertheless, he was still being raped forcefully by Dahlia who wasn't about to let the sissy get away. With his legs spread wide to accommodate the monster dildo being shoved inside of him, he moaned plaintively as he struggled to keep his place on the floor.
Not giving him a moment to rest, the second biker gave his boner a few taunting pumps in front of Bobby's cum-smeared lips.
"Ready for your second helping?" he jeered down at the hapless sissy.
"No-no-please---" Bobby wailed--his one hand raised in protest, but to no avail.
Without waiting, the grinning biker shoved his hard, eager cock deep into Bobby's gasping mouth, choking him as he gripped his longish hair to prevent his escape. I watched in amazement as Bobby's cheeks were stretched wide to try and accept the gargantuan erection being thrust down his throat. I barely noticed as a third man entered the room and began coating the tip of his hard-on with KY. At a signal from Dahlia, she pulled her strap-on out and the third biker knelt down to take her place.
Bobby was only peripherally aware of what was going on behind him, but he soon learned their plans as Dahlia stood over him gloating and the biker thrust his fat, hard cock deep into Bobby's pouting rectum.
Now he was being pounded by two big strong men and there wasn't a thing he could do to stop them. I watched in captivation as I saw his little caged, captive penis swinging rhythmically and impotently with each pounding thrust he received from behind. Occasionally, a thin string of useless pre-cum would dribble down, swinging like a pendulum until it stuck against his leg, leaving him a little more drained but no more satisfied. I could only imagine what it must be like for him, getting banged silly by two big men with no means of getting any relief for himself. Nevertheless, this is exactly what Bobby needed.
It was at that point that I decided on permanent chastity for Bobby. With a simple piercing and the right chastity device, Bobby would never be able to cum again. I would limit his sexual experiences to satisfying others, much as he was doing right now. Of course, it goes without saying that I would make sure it was only men he would be satisfying the needs of. It seemed to me that this was the perfect solution for a sissy like Bobby--to keep him perpetually denied while forcing him to service real men.
And just then, my date arrived and I had to leave the party. Much as I would have liked to stay, I had my own hunky man waiting for me and besides....I knew Bobby was in good hands.
