“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 ‘mommy’ 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 ‘mommy’ 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 ‘I 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 ‘mommy’ 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 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 crème 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 penis imprisoned inside it, and looked down on me with a smile.
“This was the best idea your mommy ever came up with—locking 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 cum?” Julie asked me as she gently squeezed my swollen balls.
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 masturbate 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 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 child, she took me down the hall to where my mommy was waiting. Actually, ‘mommy’ 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 breasts. 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 penis.
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 kowed 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 masturbating two years ago. Of course, I was masturbating 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 child. 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 squash 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 child 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 breasts 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 childishly, 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 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 cock 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 cock.
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 cock 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 cock out, only to shove it back in—even harder this time.
“Now you know who’s boss around here—don’t you Sissy-boy,” he stated breathlessly.
“Ye-yes—OOOHH!!!—yes 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 cock 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 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 cock 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 around my strap-on…I think it’s time we started letting you suck 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 cock 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 cock convulsing as he forced me to take his seed, emptying the contents of his big balls 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.
“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 ejaculation 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 breasts mashing against my upper chest 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 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 suck one of Heather’s boyfriends off. I drifted off to sleep with visions of big cocks stuffed in my mouth as I struggled to swallow load after load.