Heather’s Sissy

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Heather’s SissyHeather’s SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I’m not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it could be that he was upset about the date I was going on this evening. However, the result was the same. I pulled his diapers down and put him over my lap as I would any misbehaving c***d, and paddled his bottom until he was bawling like the big crybaby everyone knows he is.I say everybody, because Bobby’s unique situation is well known to all our friends, as well as my mother. It is especially well known to his babysitter, Julie, a girl just out of high school that is five years junior to him. That’s right, Bobby has a babysitter. Why would a 23 year old man require a babysitter, you ask? Because I don’t always have the time or inclination to change his wet diapers or put him to bed in his nursery, so I hired Julie to help out on occasions like today.But I’m getting way ahead of myself.It all started three years ago when I met Bob. I can’t say that he impressed me, either with his looks, or his physique, which I thought were rather pathetic, actually. I more or less tolerated him, since we worked together and he pestered me continually about dating him. Finally one day, I relented and we went out on a first date.He was quick to brag about how much money he had inherited and sure enough, he proved to be a big spender in the time we were together. Now, a girl needs security, and even though I, as a lingerie model, was being bombarded with propositions from plenty of hunky men, none had the financial backing that Bob did.Still, my girlfriends told me to dump the wimp (who they thought was nothing but a big sissy) and get one of the hot studs that were beating a path to my doorway every day. I was getting plenty of notice doing my modeling and if that were not enough, the skimpy outfits I liked wearing certainly got me more than just looks. I was also enjoying dating several men at once, sleeping with those that I thought were the sexiest and best looking.It goes without saying that Bob didn’t fall into that particular category, but on the other hand, I didn’t mind getting a steady stream of gifts including jewelry, clothes and eventually a new car, so for the time being, I decided to keep stringing him on for a while.This had the effect of giving him the impression that I had a serious interest in him, and before long, he went so far as to ask me to marry him.While most women in my position would have probably laughed in his face, I actually gave it some careful consideration and then came back with my own counter proposal. I would agree to marry him only if he was willing to abide by all my decisions. In effect, I would be the head of the house as well as our marriage. He would be subject to my will (since he had none of his own) and he would do my bidding, regardless of the circumstances. I wanted him to be absolutely clear on what I meant and expected.Of course, he readily agreed to these conditions but I don’t think even he knew quite what was in store for him.Up to that point, I had forbidden him any kind of sexual contact between us, beyond a peck on the cheek, which had the effect of making him very eager to consummate our wedding. However, on our wedding night, I told him I had other ideas in mind about our first night of sex and he nearly fainted when I introduced him to my eight inch strap-on dildo. If we were going to have sex, it was going to be on my terms I informed him. So despite his frantic protests, I humped his virgin a-s for an hour that night as he cried into his pillow.However, as the days went by, I still couldn’t bring myself to letting him enter me in the conventional manneróhe just didn’t appeal to me in that way. He, on the other hand, could think of nothing else, and he was getting horny as hell, continually begging me to give him some kind of relief.One day, I came home from work early, only to discover him mast.r-bat.ng to some pictures of busty women on our computer. While I am quite well naturally endowed in that area, I didn’t believe for one second, his story about trying to say that he was fantasizing about me while doing his dirty deed.My reaction was swift and immediate. Bob is both physically smaller and psychologically inferior to me, so I had little difficulty in forcing him to do whatever I wanted.I yanked him over my lap and proceeded to blister his butt with my hairbrush, scolding him like I were his own mother.It was then, while he lay over my lap sobbing like a baby, that I had my epiphany. What Bob needed was not so much a wifeówhat he needed was a mother, and one that was not afraid to be both strict and harsh when necessary. His immature behavior required constant discipline and I decided then and there to be his new mommy.I realized that the first thing I needed was a decent paddle. As he was drying his eyes, I told him to get dressed because we had some shopping to do. I took him down to my favorite fetish store and with the help of a very pretty salesgirl, we picked out a stout wooden paddle that would serve my needs (and Bob’s bottom) quite nicely. As I looked him straight in the eye and slapped the hard oak paddle against my palm, I informed him that I wouldn’t hesitate to use it if I ever caught him mast.r-bat.ng or misbehaving again. You should have seen the look on his face! And you can bet that as he was blushing furiously, the salesgirl was laughing her a-s off!Later, when I got home, I did some work on the computer myself, searching the net for a foolproof chastity device to prevent Bob from playing with himself again. I decided then and there that Bob wasn’t ready for the privilege of cumming so it was time for me to control that part of his life as well.I found what I wanted online after hours of careful research. The CB-3000 seemed to be the perfect combination of practicality and security. I ordered one and gladly paid the next day shipping charge.Two days later, it arrived, and I ordered Bob into the bedroom while I brought in a basin of ice water with a washcloth in it. He was very curious and a little bit concerned about what I had in mind but I merely informed him to do as he was told without giving him any details. Meek as always, he bowed to my superior will and followed me into the room. I had him strip down and then told him to sit on the edge of the bed. Knowing how small his pen-s is, I was concerned that the CB-3000 would be too big for him, allowing him to escape for some unauthorized masturbation. I removed nearly all the spacers and got the contraption assembled as he watched with interest, thinking foolishly it might be something he’d enjoy. If only he had known!As a matter of fact, when I began fitting his c-ck and balls into the device, he naturally began to get excited and I found it was necessary to chill his genitals with the ice cold washcloth. That put a hold on his ardor, at least, long enough to get him fitted into the restrictive chastity restrainer. He whimpered like a little baby when it became obvious what the device was used for and he begged me profusely not to subject him to such measures.However, I was firm in my resolve and in no time I had his tiny little package locked away securely with a titanium lock where it couldn’t get into any more trouble. I pocketed the key and made a mental note to take it to work with me the following day to keep it forever out of his grasp.Thus, cut off from his masturbatory misadventures, Bob was completely controlled and subject to my whims. Initially, I decided on a once per week release for him, subject to the satisfactory completion of a long list of chores I made for him every Sunday. This drove him mad initially, but between the sexual deprivation, and my vigorous use of the paddle, Bob soon fell into line.Now that we were living together, I came to realize that my friend’s initial assessment of Bob as a sissy, was dead on. This was confirmed when I allowed him to c-m while wearing a pair of panties that he was swooning over one night. I could tell he was very excited by them while I was sauntering around the house, in them and little else, so I suggested he mast.r-bat_ for his once a week orgasm while wearing them himself. I could tell from his enthusiasm that he was enthralled by the idea although I think he regretted showing his cards so readily. After he had finished, and I had locked him back into his CB-3000, an idea began to form in my head that would be intended to both excite and humiliate Bob. I liked the idea of keeping him constantly horny, while depriving him of any means of satisfying himself. This tended to make him even more subservient and servile than he already was. It seemed like a natural step that he should be subject to further humiliation at my hands so I decided to take things further by making him dress in panties and feminine nightwear while doing his chores. This would serve as a constant reminder to him what his role was and who the real head of the house was.And yet, it was a good friend of mine that suggested I take it yet a step further.One weekend afternoon, my friend Alyssa was visiting and Bob failed to show her the proper respect that I demand of him toward the superior sex. I responded immediately by pulling him over my lap and giving him a good spanking right in front of her. During his tearful apology that followed, Alyssa pointed out what a baby he seemed to be and she even started talking to him as if he were an errant two year old. I was rolling on the couch with laughter but Alyssa told me that a big baby like him should be wearing diapers, not the sissy panties I made him wear. At first, I didn’t take her seriously but the more I thought about it, the more I liked the idea.I curtly dismissed Bob and together, Alyssa and I formulated a plan for transforming Bob into Bobbyóa sissy baby who would wear diapers and dresses from now on.As usual, I kept my plans to myself and I spent another long night, ordering all kinds of things over the internet. At first, I ordered just the basics; cloth diapers, plastic pants, several dresses and onesies. The next day, I picked up diaper rash crËme, baby powder, diaper pins, and some other items that I knew would be necessary for an overgrown toddler.By the end of the week, I had a good starting wardrobe for Bobby, and when he came home from work, I met him at the door with the paddle in my hand. He went through a range of emotions from his initial anger, to frustration, to fear, and eventually, to resignation. şişli escort Nonetheless, I felt it was prudent to start his new lifestyle with another good hard spanking, just to further cement our new relationship. So despite that fact that he was in fact willing to meekly submit to my intentions, I still felt it would help set him down the right path, if he started it with a sore and stinging bottom.With tears in his eyes, I pinned him into his first diaper, after which I made a little ceremony of cutting up all his underwear. He looked absolutely ridiculous as he stood before me, sniffling, while I pulled a pink pair of plastic panties up and over his thick, bulging diaper.From that day forth, I made Bobby refer to me as ëMommy’. He didn’t like it, that’s for sure, but I told him he’d just have to get used to it. I also decided I had been far too generous with his orgasm schedule and I decided to double the time he was required to wait between them. Now, instead of one every week, I increased it to one every two weeks, which later got increased further to three weeks. I just didn’t feel that an immature sissy like him was entitled to such an adult pleasure. Of course, this made him even more subservient than before and our unequal relationship only became even more lopsided in my favor.It was then that I decided it was time to start seeing other men. And by that I mean, real men, not sissies like Bobby. It was absurd to think that a woman of my needs could be satisfied by someone like him and I was still being swamped with offers from good looking men. I really enjoyed flirting with them, even when Bobby was nearby, just so I could make him feel inadequate (which is exactly what he was). During the first year of our marriage, I didn’t take it any farther than that, but I soon found myself needing the strong arms of a real man around me. In addition, it had been many months since I had been sexually satisfied and I felt it was time for me to take care of that need as well.I started dating some of the guys I was meeting and although I think Bobby was getting suspicious, I never told him any details about my evenings. I just sent him to bed early, got myself made up and put on my sexiest outfit before leaving for the night. Bobby would be sullen and sulky when I got back (usually the next morning) but I found that after I administered a nice long enema, it usually put him right back in his place. And of course, I liked to threaten him with extensions to his period of chastity if he didn’t straighten out his attitude to my liking. On a couple of occasions, I also felt it was necessary to give him a good, hard spanking just to help clarify things again for him. By then, he was one contrite sissy!As my time became more and more tied up with the men I was dating, I found I had less time (and inclination) to spend with Bobby, changing his diapers, disciplining him, and releasing him from his CB-3000 for his once-every-three-weeks orgasm. That’s why I hired Julie, the perfect solution to my predicament. With Bobby’s bank account, I had plenty of money to hire this sexy heartbreaker from next door to keep an eye on things while I was gone. I wasn’t worried in the slightest that she’d make a move on himówith his big, bulging diapers and dresses, he looked absolutely ridiculous! I gave her full authority to discipline and punish Bobby whenever and however she saw fit and I was pleased to see how quickly she slipped into her new role.Bobby would often complain to me later that, in addition to the innumerable humiliations she had subjected him to, his new babysitter had refused to grant him his one, rationed orgasm. However, my usual reaction was to simply shrug and tell him he’d have to take it up with her. Julie had little but disdain for the overgrown baby and she was only too happy to deny him any sexual pleasure he might feel he was due.Unfortunately, the poor sissy’s balls were getting swollen from all the accumulated semen so one day, I decided to have mercy on my hubby. Using a slim vibrating dildo, I was able to ëmilk’ all his fluids from him while still depriving him of any orgasm or release. It’s the kind of job that requires patience but it’s the perfect solution for sissies who need to remain chaste as he does.As I was saying, I found less and less reason to keep my dates a secret from Bobby. The fact was, he was in denial of his state of cuckoldry and I thought it was time he faced up to it. One afternoon, while I was changing his wet diapers (he seemed to have lost all control over his bladder during the last few months), I decided to tell him exactly what I was going to be doing that night and with who. And that brings me back to the beginning of this tale but I’ll let my husband explain what happened next…’Come on, Bobby,’ Julie chided me from the doorway of my nursery, ‘Its time to get you ready for bed.’Daylight was still streaming through the windows as I pouted in silence and trudged reluctantly down the hall to where she stood, arms crossed over her sexy, ample chest. Julie had been hired by my ëmommy’ to serve as my babysitter, during those frequent times when she had better things to do, rather than watching over me. Julie was a young girl, just out of High School, where she had been the cheerleading coach for three years. With a trim, athletic body and gorgeous face, at five years my junior, it was extremely embarrassing to have her ordering me around. But then I suppose that’s why Heather, my ëmommy’ had picked her for the job. And I knew better than to question her authority as Heather had given her full permission to discipline me as she saw fit, a fact she used quite often to her advantage.As I walked past her, she reached down and slapped the thick, plastic covered seat of my diapers, just to emphasize her point. Today I was wearing a short diaper shirt (the one that said ëI love my diapers’ on it), my pink Keds sneakers, and my usual diapers and plastic panties, exposed as always.My bottom was still burning inside the thick folds of my cloth diapers and the vinyl waterproof panties that snugly encased them conspired to retain the heat of my most recent spanking. It had happened earlier when I had protested my ëmommy’ going out on a date tonight while I, on the other hand, was being made to go to bed early. Normally, I was allowed to stay up until 8:00 pm but today, I was being sent to bed at 7:15. Julie had been called over to help my mommy get me ready since she needed to prepare for her date and she didn’t want me pestering her.With my lower lip pushed out in stubborn defiance, I waddled past Julie and, still sulking, plopped myself down on the changing table, a low, vinyl covered table where all my diaper changes took place.’Come on, Sissy,’ she told me impatiently, ‘We don’t have all night.’I said nothing as she began peeling my clinging plastic panties off of my diaper and down my legs, snaking them off of my feet and setting them aside. My diapers were wet, not soaking wet, but wet enough that I was grateful for the change, especially since it would be a long time before morning. And the added moisture had made my mommy’s spanking sting all the more when she had enthusiastically applied her oak paddle to my damp, tender bottom. As Julie peeled the heavy wet cloth away from me, she saw the deep red color of my cheeks and she tried to suppress a giggle.’Look’s like someone got his little bottom spanked,’ she remarked with a smirk.I looked away in humiliated silence, knowing there was nothing I could say to reduce my indignity.’Well don’t you worry, Little Sissy,’ she told me as she began rubbing cool diaper rash crËme against my stinging buns, ‘I’ll make sure you get lots of this tonight.’True to her word, she smeared a big handful of the sticky stuff across my punished bottom, rubbing it all over with her lovely, manicured hands.With the long nail of her index finger, she flicked my CB3000 chastity device with my tiny pen-s imprisoned inside it, and looked down on me with a smile.’This was the best idea your mommy ever came up withólocking this tiny thing away, so you wouldn’t be able to play with it anymore. Sissies like you need to be kept under strict chastity,’ she told me in no uncertain terms.’How long has it been since she’s allowed you to c-m?’ Julie asked me.I blushed and looked away.’Six weeks,’ I mumbled sadly.Julie chuckled as she wiped my crotch area with a baby wipe.’That’s right…wasn’t it at your birthday party?’ she inquired.I nodded my head, reliving the devastating humiliation all over again in my mind. My mommy had made me mast.r-bat_ in my diapers in front of several of her girlfriends with my rumba panties pulled down around my ankles. They had laughed and teased me mercilessly, much to my chagrin, although in the end, I had nonetheless succeeded in splashing my insubstantial load into the soft, comforting folds of my diapers.Julie was eyeing the ruby red color of my buns and she shook her pretty head at me.’Looks like your mommy’s settled who’s boss in this house again, hasn’t she?’ she said with another superior smirk.I nodded my head in humiliated silence as she raised me by my ankles and tucked a thick stack of fresh diapers under my sticky rump, positioning them evenly underneath me.’She wears the pants and you…wear the plastic panties,’ she chuckled to herself as she pulled the thick sides up snugly to pin them. I bit my lip and looked away as she pushed a big, pink headed safety pin through the soft cotton and secured one side, then the other.Pulling open the drawer next to the changing table, she began sifting through the various waterproof panties to find something for me to wear.’Let’s see, what shall we pick out for a diaper-wetting sissy who’ll be spending another long night in his crib…?’ she asked herself.’Here we go,’ she said brightly, ‘How about these?’She held up a pink pair of nursery print plastic panties with white lace sewn around the leg and waist holes. They were very babyish and designed for no other reason than to humiliate me.Gathering them in her hands, she worked my feet through them and began snaking them up my skinny, hairless legs.’These are perfect for mommy’s little bedwetter,’ she assured me in her condescending tone as she worked them over the spongy soft bulk of my diapers, ‘and they should keep your crib mattress dry–all night long.’Running her long nails around the elastic waistband of the panties, she worked them around until they completely sealed the bulging cloth.I hated having to wear these embarrassing diapers but it was just one of the many indignities I had to suffer.’There,’ she said as she removed my diaper shirt, ‘Now we just need a nightey and then you’ll be all set.’Standing up, she went over to the closet where she sifted through my extensive wardrobe of dresses and baby wear until she found a pink gingham şişli escort bayan nightey with a super short hem. Bringing it over, she dropped it over my head and I dutifully raised my arms to assist her.’Go brush your teeth now and then you can say goodnight to your mommy,’ she told me.’Yes Ma’am,’ I replied submissively.Waddling into the bathroom, I gazed at the toilet that was forever forbidden to me and sighed. Soon, I would be in my crib, sleeping on a waterproof vinyl sheet, my teddy bear clutched in my arms. Somewhere during the course of the night, I’d wet myself heavily several times, as usual.After taking care of my scant business in the bathroom, I went back to the nursery where Julie was still waiting.I would have liked to take a pee in there but the only peeing I would be doing tonight would be into my thick, thirsty diapers.’All done?’ she inquired in her businesslike manner.’Yes Ma’am,’ I responded.’Okay, come along then,’ she said as she reached down and took my hand. Leading me like a c***d, she took me down the hall to where my mommy was waiting. Actually, ëmommy’ is a misnomer since in reality it was my wife, Heather, although she was my spouse in name only. She was sitting down on the couch, talking to someone on her cell phone and completely ignoring me as Julie walked up with me in tow. I waited patiently until she was finished and then she snapped the phone shut, dropping it into her purse.’All ready for bed?’ she asked in her curt, haughty tone. It was quite obvious who made the rules here and who had won our most recent argument. She had a habit of settling disagreements between us by taking me over her lap and blistering my bottom with her paddle. My fanny was still throbbing and sore as I stood before her, broken in spirit once again.’Yes, Mommy,’ I replied meekly.Heather was dressed in one of her sexiest outfits for her date. A short, snug mini-skirt and very high heels, with a matching halter top that clung deliciously to her big, round, swelling br.easts. I stared at them longingly, wishing once again that she’d let me touch them, as she had done when we first started seeing each other. But that was years ago now and our relationship was night and day from how it had been when we were dating. Now, she held all the cards and she lorded her authority over me relentlessly. Still, my tiny little member was pushing with all its might against the clear plastic cage in which it was held captive. The sight of her in all her sexy finery made me delirious with lust but my wiener was prevented from even getting hard. I shifted uncomfortably, unable to provide any relief for my aching, deprived pen-s.Turning me around, she lifted up the back of my short nightey to look at my fat bubble-butt, caused by the thick diapers I was wearing. Despite their thickness, we both knew they’d be soaked by morning.’Tonight, you’re going to bed with a very sore bottom, aren’t you Sissy?’ she stated emphatically.’Yes, Mommy,’ I mumbled.’Maybe that’ll teach you a lesson, next time you start sassing me,’ she continued.’Yes, Mommy,’ I replied submissively.I still hated it when she humiliated me in front of others, even though Julie had been babysitting me for the past year and a half.’I’m going to continue dating real men, whether you like it or not, Bobby,’ she said in her hard tone of voice, challenging me to oppose her. I knew she was daring me to argue with her, so she could show Julie just how cowed I had become but I didn’t dare talk back to her. My cheeks buzzed with shameful humiliation and I hated how weak I was acting.’Yes, Mommy,’ I answered, acknowledging her complete superiority.She stared at me with her hard, unrelenting gaze until I was forced to look away from our unequal battle of wills.’Come along, Sissy,’ Julie said as she took my hand, ‘Its beddie-bye time for you.’I sniffled in defeat and as I turned to go, the doorbell rang, signaling Mommy’s date had arrived. I trudged after Julie, afraid to face my wife’s date who, in all likelihood, would be ravishing her in the bedroom, later tonight. At the same time, I’d be lying in my crib, wearing another wet diaper, and unable to satiate my own ever present horniness because of the cursed CB3000 I was wearing. God, how I hated that thing! Heather had made me wear it, ever since she caught me mast.r-bat.ng two years ago. Of course, I was mast.r-bat.ng because she had cut me off from sex but that made little difference to her. It was her considered opinion that sissies didn’t deserve orgasms and she was going to make sure I wasn’t able to achieve one on my own. The CB3000 made quite sure that I couldn’t. Constructed from an ingenious and diabolical design, the CB3000 couldn’t be removed once locked and its restrictive shape prevented the male from being able to become erect. Heather kept the key locked away and sometimes I was forced to go months without any kind of relief. And being bossed around by two fabulously sexy females didn’t help my situation either.Heather led me back to the nursery, holding my hand again like I was a c***d. Behind me, I could hear the door opening and my mommy greeting her boyfriend both enthusiastically and amorously. At the same time, I felt my temperature rising in a sudden unexpected surge of anger. It was so frustrating! I had made her my wife and then she had turned the tables on me, turning me into her helpless sissy baby, making me sleep in another room, and denying me any means of satisfaction. The unfairness of it all burned inside me like a smoldering flame.I stomped my feet in anger, balling my fists as I felt my face flushing with rage.’What’s the matter, Sissykins?’ Julie asked sweetly, ‘Do you want your baby bottle?”No!’ I spat back viciously.Pushing her rudely aside, I stormed out of the room, filled with angry determination. There was no way I was going to stand another minute of this insanity!I found Heather–my wife, locked in a torrid embrace with some guy I’d never seen before. He was easily over six foot, and probably two hundred and fifty pounds of bulk and muscle. With my skinny and frail physique, he looked like he could squish me like a fly.Still, I was consumed with a jealous rage that I couldn’t control and I stomped into the room, yelling at the two who were oblivious of me. No doubt, Heather was confident that I had been put to bed and was out of her hair for the night.I knew I must look completely ridiculous before this man. Here I was, my pigtails tied up with two sassy pink bows, wearing a short, pink, little girl’s nightey, and my thick, bulging diapers and shiny plastic panties there for all to see. I was a picture of sissy-toddler fury. Both of them stood quite a bit taller than I and I felt like I was forcing a confrontation with my parents.’Stop it!!’ I shouted hysterically in my high pitched voice.Heather broke her kiss for a moment as she looked down at me (in her heels, she’s a good foot taller than I), with both shock and surprise. However, she recovered instantly, just as Julie was running out into the living room from the nursery.’I’m so sorry!’ she exclaimed apologetically, ‘He just ran out before I could catch him.’Heather regarded me coldly before delivering a sound slap to my cheek that actually had me seeing stars.’OOUCHH!!!’ I cried, and her unexpected response threw me off guard. I rubbed my stinging cheek and looked up at her with a wounded expression of hurt.’Looks like someone needs to get his bottom re-warmed,’ she growled menacingly.Before I could respond, she strode over to the table where she’d left the wooden paddle from before and scooped it up, clutching it tightly in her slim hand. My heart skipped a beat and I felt an icy knot of fear turning within my stomach. For a brief moment, I considered my options and I actually gave some thought to resisting her physically. However, my knees grew weak and as I saw the angry fire burning in her eyes, my fragile will crumbled. Filled with trepidation, I felt again like a helpless c***d in her stern presence and I trembled uncertainly.Heather reached over and snatched my wrist in her iron-like grip, taking advantage of my surprise as she hauled me towards her.I squealed with fear and lurched forward off balance as she took a seat in the only straight-backed chair in the room. Her boyfriend chuckled in amusement as he saw this hot, very sexy woman taking complete control over her errant husband to mete out the discipline he had just earned.Taking hold of the elastic waistband of my plastic panties, Heather angrily tugged them down my legs with short, jerky motions. I cried out in protest, shaking my head frantically and stomping my feet as my plastic panties went past my knees. I watched helplessly as her big br.easts jiggled within the tight, shiny fabric of her low cut top and I was momentarily mesmerized by their fabulous shape. It seemed that the closest I ever got to them these days, was whenever she took my diapers down to give me a spanking.I could see she was quite upset with me and I gulped with fear in anticipation of the consequences of standing up to her.’No…please!’ I pleaded weakly with her.She completely ignored me and after pulling my clinging plastic panties down around my ankles, she yanked me over her smooth, toned lap. Needless to say, Heather is blessed with long, firm legs and when she wears a mini-skirt like she had on tonight, the effect was breathtaking. However, I knew she hadn’t dressed like this for me and soon the biting sting of her paddle would be distracting me from her fantastic body.I gasped with fear as I fell forward, only just managing to stop my fall with my hands outstretched. My gaze fell upon the glossy, five inch high-heel sandals she had on as I felt her impatiently removing the pins from either side of my thick cloth diapers.’No! No! Please!’ I wailed piteously and I reached back to try and stop her. I was so mortified to be punished like this in front of not only Julie, but her boyfriend as well!Heather responded quickly by grabbing a hold of my flailing wrist and twisting it painfully behind my back, forcing me back down again to the floor against my will.’OUCHH!’ I wailed, ‘You’re hurting me!”That’s nothing like you’re about to feel!’ she snapped.I struggled helplessly, perched over her lap, but with the extra height of her high heels, I found myself losing my balance as my torso crept forward. With my diaper pulled back between my legs, my red, tender bottom was facing up, fully exposed and defenseless to her intentions. Glancing up, I saw Julie smiling down on me with satisfaction as she crossed her slim arms over her perky chest.I squirmed and made weak protests but they were abruptly cut off by the first searing slap of the paddle. Wielding it like a fierce weapon, Heather swatted me again, right in the center of my already punished cheeks. Two fresh new red oval marks formed over the previously crimson surface, re-igniting the inferno that had only been lying dormant.I howled in pain, kicking my feet wildly as if that would somehow alleviate the scalding fire being applied to my sensitive bottom. Bursting immediately into tears, I began sobbing like a baby as she continued to slap my poor fanny with her hard, unforgiving paddle.SMACKK!! WHACKK!! CRACKK!! SMACKK!!!I wailed out at the top of my lungs as she applied her paddle to every square inch of my soft, cherry-red bottom. My eyes were filled with tears but I could still see that her hunky boyfriend was fondling a growing hard-on through his pants. It was bad enough that I was being punished in front of him but it was even worse that he was getting turned on by it!I was completely defeated and all resistance was gone. I lay there, bawling c***dishly, as she kept up an even rhythm, slapping each flaming cheek harshly to teach me a lesson I’d never forget.Finally, the blistering spanking was over and I lay over her lap, the tears streaming down my face in wet profusion. I tried to get up, only to feel strong, rough male hands pulling me up and off Heather’s lap. I had no idea what was going on but neither was I in a position to argue. Still crying loudly, I was made to bend over the table with my diaper serving as a cushion while I felt Heather’s boyfriend brusquely forcing my wobbly legs apart.’Its time you learned your proper place around here,’ he said in a husky voice.’Wha-what are-are you d-doing?’ I stammered fearfully between sobs. For a moment, I thought he might use his belt on my blazing bottom.Without responding he reached into the pocket of his jacket that was hanging over a chair and produced a tube of KY jelly.I didn’t like where this was headed at all and I tried to stand up straight but the guy simply pushed me back down, leaving my stinging, throbbing bottom sticking out and vulnerable. He positioned the tube right at my anus and squeezed nearly all its contents into my rectum.’No…please…please don’t,’ I begged of him between ragged sobs.He chuckled throatily and undid the buckle in his pants, causing them to drop like a curtain. To my horror, I saw that his boxers were tented in front by a massive erection and I gulped in real fear now.Although I had had a pretty limited sex life up to this point, I had never once considered doing anything with a man and now I was being forced to submit willingly. This man intended to take me from behind and there was nothing I could do about it. Nothing at all!Grasping my burning, crimson cheeks in his hand, he spread them apart as he positioned the fat head of his c-ck at my puckering hole. I thought there was no way that huge thing was going to fit inside me but I hadn’t contended with this man’s stubborn determination. With several hard pushes, he tried forcing the big blunt end inside me and I slapped the table in angst-filled protest. I begged him no but he only laughed and renewed his battle against my vulnerable sphincter.’Nooo!! Nooo!!’ I cried, but it was too late.All of a sudden, the man’s gigantic member slid past my defeated hole, plunging deeper and deeper into my virgin passage. My eyes crossed and I squealed loudly, sounding more like a little girl than a grown man.I was utterly ashamed as I clutched the side of the table, trying to brace myself while he patiently grew used to the tight embrace of my back passage. My face and chest were a bright shade of shameful red as he slowly slid it in as far as it would go. Bottoming out, he held his monster deep inside me, making me squirm in discomfort. It felt like he was splitting me in two and I squealed again, trying to escape, but he easily held me in place, grinding his hips against mine as he forced me to take every millimeter of his big, fat c-ck.Across the table, Heather and Julie smiled at me in wicked agreement. Whatever humiliation I had felt in losing to her earlier was paled by this experience. To have a hard, thick c-ck buried all the way inside me made me feel completely emasculated and humbled.My hole ached from being stretched so wide and in an effort to relieve the pain, I tried to spread my legs wider to accommodate him but it did little good.I moaned again as he pulled his hard, slippery c-ck out, only to shove it back inóeven harder this time.’Now you know who’s boss around hereódon’t you Sissy-boy,’ he stated breathlessly.’Ye-yesóOOOHH!!!óyes Sir,’ I replied between moans.I could feel his heavy weight against me and it was equally obvious I could do nothing whatsoever about it.I could see Heather reaching into her purse for her digital camera, and she pointed it at me, taking several humiliating shots just as her boyfriend stuffed his massive, rigid c-ck deep inside me again.’I want to make sure we capture this moment for all of posterity,’ she giggled, ‘I’m going to frame it and hang it up on the wall in your nursery, Bobby, so you’ll always remember what it was like when your virginity was taken.’I moaned weakly, helpless to stop this big brute from sodomizing me. After stretching me out and getting used to my snug passage, he began a long, degrading rhythm, in and out, going deep inside with every thrust. I lay there submissively, feeling every meaty inch of his monster c-ck as it plunged in, until it bottomed out, making me respond with my feminine sounding moans.’You’ve needed this for a long time, Bobby,’ Heather smugly assured me, as she looked down at me with her hands on her curvy hips, ‘And you’d better get used to it, because it’s the only kind of sex you’ll be getting from now on.’Tears of frustrated humiliation trickled down my cheeks as I looked up to her pretty face to behold her superior look of confident satisfaction.’No…no…’ I begged her weakly as I panted from the enthusiastic humping I was receiving, ‘no…OHHH!!’Another hard thrust pushed me against the table as he buried his ramrod to the hilt, deep inside me.’And I think its time we allowed you to show off your talent for cocksucking too, Bobby,’ she continued in her wicked tone.I shook my head no but she went on, ignoring my plight.’Oh yes, you’ve demonstrated quite a talent when you’ve had your lips wrapped around my strap-on…I think it’s time we started letting you su-k the real thing.’I wanted to say something in opposition but her boyfriend had started thrusting harder. He was gripping my stinging cheeks with both his hands as he rammed his c-ck into me repeatedly. With hard, punishing thrusts, he hammered me from behind, slamming my body and making me dizzy from his efforts.And then, unexpectedly, he stopped.Clutching my stinging buns hard enough to make me cry out, he suddenly lunged forward and forcefully stuffed his battering ram all the way in, roaring as he came with boisterous gusto. I felt a warm infusion of creamy goo filling my back passage as he exploded in a tortuously long orgasm. Holding me in place, I felt his engorged c-ck convulsing as he forced me to take his seed, emptying the contents of his big balls deep within my rectum.Being pinned down and unable to move, I heard him gasping for air behind me as he slowly began to recover from his incredible climax. At the same time, my poor, aching hole was sore from being stretched so far and for so long. Quietly, I wept with shame. I knew only a true sissy would have put up with this and I shuddered at what I’d become.’Julie,’ he finally said between draughts of breath, ‘Get me a buttplug.’Julie winked at him and disappeared down the hall returning with my pink rubber plug and a wide smile on her face. Oh No…Slowly easing his flaccid member out of my hole, Heather’s boyfriend quickly replaced it with the thick synthetic buttplug, forcing my anus to remain stretched open, as well as trapping his ej-c-lation of creamy semen inside me.’That’ll help serve as a reminder to you,’ he informed me as he slapped my red bottom.I winced and sniffled as Heather came up behind me and began pulling the sides of my diapers up. Bending over me, she held the ends together and secured the safety pins, sealing me back once again in my infantile prison.’No…please,’ I begged her, but she only smiled down at me with that superior look of hers.’You’ve had a quite a night, Bobby. And now its time for your beddie-bye,’ she said as she retrieved my plastic panties. They must have come off while I was being spanked and she held them open for me patiently, while I inserted one foot after another into the leg holes. Slowly, teasingly, she pulled them up my smooth, shaved legs, drawing out the humiliating ordeal to further demonstrate her dominance and superiority over me. My face was beet red and I kept my eyes downcast but I could feel the stares of the other two as they watched me being dressed like a helpless baby for his bed.I watched her long, finely manicured fingernails as she circled them around my waistband, working the shiny waterproof panties over the bulky cloth diapers pinned around my hips. After ensuring that the panties completely covered my diapers, she let them go with a snap of the elastic. I was still looking down when she put her slender finger under my chin and raised it, forcing me to look into her dark, beautiful eyes.Without saying a word, her smile said everything between us. I would forever be her little baby, to be treated as she saw fit. My lot was to be obedient, compliant and submissive, to do without orgasms while at the same time, be prepared to service her boyfriends whenever and however she deemed was necessary.Leaning down, she kissed me tenderly on the lips and hugged me.’Nighty-night, Sissykins,’ she said sweetly.I felt her big, soft br.easts mashing against my lower chin and I yearned desperately to be able to touch them, if only just once.’Nighty-night, Mommy,’ I replied meekly, the defeat plain in my voice.As she released me from her embrace, Julie took my hand and led me out of the room, patting me gently on my thick, diapered bottom.’There, there, Baby,’ she consoled me, ‘Its off to beddie-bye now so your mommy can enjoy her date. But don’t worry, I’ll make sure you get to snuggle with your favorite teddy bear tonight.’I cried softly as we entered my softly lit nursery. Julie lowered the side to my crib and she gently pushed my pink pacifier between my quivering lips.’Awww, Sweetie,’ she said soothingly, ‘Its not so bad. At least now you’ll be getting sex again…it just won’t be with a woman.’She giggled as she tucked me in, handing me my teddy bear and bringing the baby blankets up around my chin.I heard the front door close as Heather and her boyfriend left the house, putting the final closure on my humiliating night.’Nighty-night, Sissy,’ Julie said as she waved goodbye to me from the threshold of the nursery.I sucked on my pacifier without thinking, wondering how soon it would be before I was required to su-k one of Heather’s boyfriends off. As I drifted slowly off to sleep, my mind was filled with visions of big cocks stuffed in my mouth as I struggled to swallow load after load.

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