Being a short man in a tall man’s world had been one long, 27-year string of disappointments for poor Michael. From being bullied at school to being passed over for promotion after promotion at his modest job in the accounting firm, it seemed the only attention Mike ever got was the kind he didn’t want. The worst of it all, though, was being all the ladies’ “best friend” but never their lover. No, Mike’s only contact with females throughout the adult portion of his life was when they were sobbing on his shoulder the morning after a much taller, more handsome man would treat them wrong the night before. Well, that and his occasional thrill on Pervert’s Row at the local strip club, tucking dollars into the girls’ G-strings or, even better, the ankle straps on their spike heels. Sometimes they even let him put the bill in his teeth and let them take it with their voluptuous breasts, then give him a face full of said breasts. It seemed to be his destiny, to be that lonely, slightly awkward loser with the decent apartment and decent job, wasting most of his nights trying to get noticed on Fetbook, and the rest emptying his wallet at the strip bar, going home with sticky messes in his boxers after those oh-so-beautiful women let him touch them.
Well, that was his life before he met Sally. That’s when absolutely everything changed. When she popped in with a private message on his Fetbook page, Mike’s entire world turned upside down. This wealthy, tall, dark-haired, athletically built vixen swooped into his life and systematically fulfilled every little fantasy he’d ever had in the whirlwind that was their first few months as a couple, and he willingly let her push him beyond his outer limits into fantasies he never even knew he had. In short, she was perfect.
Of course, there was a reason Sally was perfect. Unbeknownst to hapless little mikey, as she called him, Sally had been watching him for a long time. Owner of said strip club, she knew all her regulars, and little mikey was an object of interest from the first day he awkwardly sat at the bar and watched those girls from a distance. The longing in his eyes was as obvious as the nose on his face. When she found his profile on Fetbook, it was almost hysterical to her how predictable he was; lonely pathetic little wimp looking for a Mistress to abuse and humiliate him, to let him worship her feet, to make him into a pet for her amusement. They were everywhere on that site, and the few that worked up the nerve to approach her got flat rejected with a referral to a professional Domme she knew. Because most of them just wanted one night of wild beatings and humiliation and then go back to their stupid little lives until they felt that itch again. Little mikey was different, though. Watching him in the club all that time, she knew he was different. He would follow her to the ends of the earth just for the chance to lick her heel.
And in reality, all his little shortcomings fit perfectly into her desires. His “problem” with premature ejaculation was perfect. He never begged to put his little winky inside her, and in return she taught him well how to service her with his mouth, his fingers, the many toys in her collection. And he absolutely loved it when she shamed him over the messes he made; his full-body shudders as he groveled for forgiveness for being so pathetic were like candy for both her sweet tooth and his own. But even after she convinced him to give up his job and his apartment to move in with her and be her house slave, there were places Sally wanted to take him that he wasn’t going to go without a little help. Fantasies she had that she was determined to make him fulfill. But that was just a matter of timing. Patience. And Sally had plenty of that.
They’d been living together four months, and Sally had “little mikey” trained into a nice little routine. He abandoned his job at the accounting firm happily as part and parcel of moving in with her. They slept in until noon, and he’d get up, fix her breakfast in bed (he was quite a good little cook, to her surprise), and sit dutifully at her feet while she ate, massaging her ankles and calves. She’d get up to shower and do her makeup, and he’d stand at the ready in the master suite, holding her towel while she teased him with seductive poses and noises behind the steamed-up sliding glass door, turning his head when she was finished. (He wasn’t allowed to look at her naked body unless she explicitly gave him permission; his backside had taken many welts for that transgression.) Once she was dressed and ready for work, she’d give him a list of rooms to clean top to bottom while she was gone, with the promise of her strap on his backside if they failed to pass inspection. And they rarely passed inspection. She was pretty sure that was deliberate on his part, though. There was always something obvious, something a complete idiot would have noticed, left untouched while the rest was immaculate. So, when she arrived home from work, there would be the inspection, then his beating, and then he would, sans clothes, serve her supper at the table while he whimpered and groveled and kissed and massaged her tired feet in between fetching her wine. And later, depending on what mood struck her, she would take him down to the dungeon and abuse him until he cried out the little safe word she gave him (No more, Mommy!) and make him clean up his little messes on the floor under her St. Andrew’s Cross. Or she’d lie on the bed and make him please her long into the wee hours of the morning, until he collapsed from exhaustion. On her off days, she’d dress the both of them up in properly coordinated leather and take him to the BDSM club to parade him around on all fours, beat him, and humiliate him in a more public forum. She knew he loved that more than anything else; she had to put a cock ring on him to keep him from ruining his leather shorts, a fact she made sure everyone there knew.
And she pushed him farther and farther toward what she wanted out of him; he went under the laser to get rid of his pathetic little beard because she didn’t like being tickled by hair when he went down on her. He agreed to undergo bi-weekly Brazilians when the alternative was sleeping in a cage at the bottom of the bed “like the hairy little animal you are”. And he hadn’t cut his hair since he moved in. By September, he was as androgynous as could be, a just over five foot tall little boy-girl, his wispy blond locks in a little cascade on his shoulders. He was ready, and it was time for her to make a little magic happen. After all, what better time for a little magic than Halloween, for a witch of Miss Cassandra “Sally” Divone Nenet’s caliber?
~~2"Can you believe it? We’re gonna have our first Halloween together!" Sally asked coyly, as she cuddled Mike’s shivering form, stroking his naked back as she brought him out of his sub-space. Aftercare was paramount when taking care of a pain slave, and Sally was every bit the expert caretaker as she was the sadist when it was time to discipline him.
“Mmmm,” Mike replied absently, just barely becoming aware of her words again, the adrenaline subsiding, replaced by her tender touch.
“We have invitations to an absolutely enormous party, you know,” she continued. “So many of our friends will be there!”
Mike flinched a bit when she said that; that phrase was all but code for “Mike’s going to get flogged in front of a crowd.” Terrifying, yet incredibly stimulating. He hadn’t realized how much of a turn-on humiliation was until Sally introduced him to it. “Fun,” he managed weakly.
“You know what would be extra fun?” Sally cooed. “How would you like the chance to switch for the night?”
That got his attention. “Wait… what do you mean?” he said, popping his head up from her bosom.
“I’m sure you’d just love to pick out my costume for me, and be in charge the whole night, in front of all those people, wouldn’t you? No safe words, no nothing, just little mikey playing Big Man Michael, and Miss Sally being just little sally?”
His eyes widened as she spelled it out, and visions danced in his head. He knew exactly what he’d want to see her in; he’d fantasized about it since the first time he laid eyes on her. No leather that night, no, not at all. He gathered his thoughts… she wanted an answer, no doubt. “How… I mean… what… do I have to do?”
“Well,” she chuckled. “First you have to prove that you’re capable of being a Master. How about going a whole week without any discipline?”
“But that’s not fair!” he protested. “All you have to do is make up a reason!”
Her face darkened noticeably. “When have I ever disciplined you and you didn’t deserve it?”
“I… uh… never…” he replied weakly. Truth be told, the rules were all laid out. All he had to do was follow them. Except he wanted her strap on his backside. NEEDED it. He felt unwanted, unloved when Sally didn’t discipline him.
“So what makes you think I would be so unjust as to do it just to win a bet?”
“I… you wouldn’t, Miss Sally.”
“Of course I wouldn’t. Now apologize for making such a slanderous accusation!”
Mike slunk, trembling, down off her lap and onto his knees in front of her. “Forgive me, Miss Sally. I’m a horrible, ungrateful boy, undeserving of your love and care and affection. Forgive your unworthy slave of his transgressions.” It was a well-rehearsed line, and the words came easily.
“You are unworthy, ungrateful, and pathetic. But I will forgive you once again, little mikey, even though you deserve nothing less than to be cast from my sight!”
“Please, Miss Sally!” he begged. “Punish me however you see fit, but don’t send me away!”
Now would usually be a time he would be disciplined, but he’d just spent two hours on the rack; he was in no shape to take another thrashing. “No no, little mikey,” she said, grasping his head and pulling him gently. “Come back to Miss Sally’s bosom. All is forgiven.”
He climbed back up and buried his face in her chest as she stroked him. “So does little mikey want to try to be Master for a night?” she whispered.
“I… I would like that,” he whimpered back, his breathing starting to even back out.
“Then we’ll start tomorrow,” she purred.
“What… happens if I don’t make it?” he asked, almost as an afterthought.
“Well of course, if I win the bet, I get to pick your outfit, you get to be the slave, no safe words, no limits. It’s only fair, don’t you think?”
“Of course,” he replied sheepishly.
Sally had every intention of keeping her little promise, to only discipline him when he actually earned it. But she knew just as well as Mike did how needy he was, how desperate he was for her attention and affection. She wouldn’t need to break that promise. To Mike’s credit, he definitely went the extra mile that day. But the harder Mike tried to please, the less interest she showed. She barely acknowledged the elaborate breakfast of Belgian waffles with fresh-squeezed orange juice alongside her coffee. She caught a bite to eat at work, and coldly announced she wasn’t hungry for the admittedly gorgeous-looking Quiche Lorraine he prepared for her. Her inspection of the rooms on his list was quick and silent; not even offering the slightest compliment for the touches he added, like fresh flowers in her office, and she didn’t even bother inspecting the on-suite, which wasn’t even on that list, but that he’d meticulously scrubbed top to bottom. And to top it all off, she retreated to the bedroom and shooed him away, declaring she was tired and wished to be left alone.
Mike was devastated. What had he done so wrong that she would shut him out like this. He choked back tears as he stared blankly at the laptop screen, at the special Halloween costume he’d picked out for her that day as he waited for her to come home. She didn’t even want him to pleasure her, or even massage her back while she slept! And he dare not ask, no, that in and of itself was an infraction of the rules! Mike’s purpose was to pleasure Sally; it was for Sally to decide what Mike needed and deserved. He had to try harder, do more, because clearly his mistress was displeased with him.
And try he did. The next day he was tireless, cleaning the entire house top to bottom, fixing Eggs Benedict for her breakfast and a thick, juicy ribeye steak with creamed spinach and roasted fingerlings for supper. But she showed no interest whatsoever. She spent the evening in her office, and when she came to bed, she banished him to the dreaded cage.
The next day, it was more of the same. He worked relentlessly all day, cleaning, cooking, doing laundry, and once again she devastated him by coming home late, ignoring the elaborate dinner, isolating herself from him. Few words, no physical contact at all. Mike was bewildered as he lay in the cage again, trying his best to keep his tears silent. At this point, Halloween was an afterthought, the promise of being Master for the night pie in the sky. He wasn’t even sure if she still cared for him at this moment, and that terror trumped all other thoughts, desires, needs. Trembling, weeping, and panic-stricken, he accidentally bumped the cage door as he shifted his weight.
“Be quiet down there!” she shouted. “How dare you wake me?!” Of course, she wasn’t sleeping, she was just silently relishing the mental anguish she was inflicting on him. Physical punishment wasn’t the only path for the sadist. And for sure, he was near his breaking point already.
“I… I’m sorry Miss Sally,” he whimpered, trying to stifle an outbreak of sniffles.
No answer. Mike couldn’t take it anymore. “Please, Miss Sally, what did I do wrong?! Why can’t I sleep in your bed?!”
“Come out of that cage!” she snapped, flipping the light on. He knew what was coming now, but it didn’t matter. He needed it. Damn the costume party, he needed it. He crawled out and knelt on the floor beside her. “What is the rule about Mistress’ instructions?” she asked, more calmly, but still very stern.
“Miss Sally knows what is best for us. We are never to question her judgment,” he nearly whispered, his head down.
“What do you suppose Miss Sally should do about this, little mikey?”
“I need… to be disciplined, Miss Sally.”
“Yes, yes you do,” she said, feigning a solemn tone. “Get Miss Sally her strap.”
He cringed a bit, but at the same time his heart warmed at having her undivided attention again, something he’d been starved of these last few days. He went to her closet and retrieved the pink-handled, heavy leather implement from among her various implements of discipline, laid it on the bed at her feet, and got back down on his knees. “Up here,” she scolded. “Assume the position.” Quickly he stripped naked and laid down on the bed next to her, face down. As he braced for the coming physical pain, he found himself very suddenly erect.
Of course, Sally anticipated that outcome. “Where is your towel, little mikey?” she demanded.
“I… I’m sorry Miss Sally,” he fumbled, scrambling off the bed, embarrassed as his erection stood out in front of him like a flagpole as he walked by her toward the on-suite. He returned with a dirty towel he retrieved from her laundry basket and was most dismayed when he saw what was in Sally’s hand.
She smiled as she held up the little ring. “Stand right here, little boy,” she commanded. He complied, and she grasped the tip of his penis and squeezed. It wasn’t painful, but it was definitely humiliating for Mike as he watched it quickly sag and shrink back to its normal, pathetic self. She lifted it up and cinched the cock ring snugly just above its base. “This is not fun time, this is discipline time,” she said calmly, taking on a motherly tone. “Little mikey doesn’t deserve fun time right now, does he?”
“No Miss Sally,” he mumbled. That little ring, he hated and loved it so, stealing away his manhood, his sexuality, but at the same time exciting him with the humiliation of her taking total control of every aspect of him.
“Now, assume the position.”
He spread the towel out on the bed, lay across it, and braced himself, this time decidedly less comfortable with the blood flow futilely straining against the cock ring, the base of his penis swelling painfully while the rest remained flaccid. There would be an orgasm in his near future, but it would be a painful one, like when she milked him, not at all pleasurable like when he was strapped to the St. Andrew’s cross.
A loud crack and searing pain across his bottom snapped him out of the thought, and he whimpered in spite of himself. Then came another, and another. The blows continued as he gritted his teeth and struggled against the inevitable tears.
She was silent as she moved, efficient, deadly accurate, working inch by inch from the very top of his hind quarters down to the tops of his thighs, watching carefully as the angry welts rose up, listening to the changes in his vocal responses. Down in the dungeon, during “funishments”, she’d often draw blood, but not tonight. Tonight it would end when the heaves began, after he’d made his little cummies and was sobbing like a proper little boy should after his Mommy spanked his deserving little tush. She heard him gasp a bit and tense up, letting loose a whimper, and she knew what had happened. She knew just as well as he did how unpleasant those orgasms were, but she had to maintain the appearance that this was discipline, even though she knew well how much he was starving for the attention. Finally he broke into sobs, and she stopped. As she strode back to the closet and hung the strap in its proper place, she cooed, “Now, what does naughty little mikey say?”
“Th… thank… you… Miss… S… Sally… f… for caring… enough… to… to correct me,” he blubbered into the towel, his entire body shuddering under the intensity of the pain he’d just experienced.
“Poor baby,” she continued as she sat back down on the bed, running her fingers through his hair, rhythmically massing the back of his head. “You’re just such a little mess, aren’t you? It’s so hard for little mikey to be a good boy, isn’t it? Poor, poor baby… But don’t you worry, Miss Sally will always be here to help, teach you how to be good. Yes she will, baby. Yes she will…”
It wasn’t too much later that he finally fell asleep exactly where he lay. And Sally’s head was filled with plans and preparations for what was to come, just a few weeks away. A simple bet was the final step toward him being the perfect slave. Well that, and a little magic.
3Mike had earned himself quite a few more such spankings over the course of the next month as he begged and pleaded with Sally to tell him what her plans were for Halloween, but she was steadfast, teasing him with only the promise that he was going to absolutely love what she had planned. See, Sally knew about his other little fascination, those little Asian girls with their elaborate Victorian outfits he fawned over. And she intended to indulge it for him. On her terms, of course.
Finally the big night arrived. Halloween fell on a Monday that year, which was fortuitous, because she could close the bar for the day and not worry about losing much in the way of cash flow. And since the big party didn’t start until nine in the evening, there was plenty of time for more teasing that day. Mike was practically in panic with anticipation of what she had planned, and at five o’clock, after a light lunch, she left him to clean the kitchen while she dressed.
Mike was absolutely in awe when Sally resurfaced in a stunning, floor-length, long-sleeved black Victorian dress that flared from the waist, with subtle powder-pink accents at the hem, ringed with pink bows at the knee. How could she have known of his Lolita fantasies? And stranger yet, what else did she have planned? He’d imagined her in this very dress the first time he saw it, on his arm as he donned a steampunk three-piece suit in all black, a monocle in his eye and a rakish top hat, the two of them strolling through the crowd, all eyes on them, admiring their finery.
“You like?” she purred, knowing the answer.
“It’s… you’re beautiful, Miss Sally,” he stammered. “Perfect.”
“Of course I am,” she laughed. “Are you ready for yours now?”
“Y… yes Miss Sally!” He stood straight, and she spotted a subtle tremor in his hands.
“Turn around,” she said. He complied, and she swiftly applied the blindfold. “Now you stand right there while I get everything ready, and I’ll be right back to collect you.”
“Y… yes Miss Sally…” His nervousness was delicious, and Sally was quite certain he’d already made a mess in his underwear. No matter.
The outfit rustled subtly as she pulled its hanger from the closet and hung it on the corner of her vanity. She opened a box she had tucked into the back of her closet several weeks ago, ripped loose the packaging on the first bag, and lay her hands across the items within, whispering the all important words:
“The two become one, and the one becomes all,
As pleasure combines with the irresistible call,
Desires to merge, and barriers to fall.
As above, so below.”
And with that, Sally took one of these suddenly very magical objects and laid it along with a tin, a pump bottle, and a tube on her nightstand and went to retrieve her little slave boy.
Mike had stood dutifully in the kitchen where she left him, blindfolded and nearly overcome with anticipation, fear, and excitement over what his Mistress had planned. And, contrary to Sally’s thoughts, while he was painfully erect at the moment, he had managed to control himself, though with some difficulty. Standing perfectly still like this was helping, but the thoughts running through his head weren’t. Sally in that stunning black and pink dress, smiling seductively at him. Oh, that he could have been strong enough to contain himself and won that bet, the things he’d have done with and to her. Of course, Mike didn’t have it in him to be as severe as Sally, but still, he’d certainly have enjoyed her going down on him, a treat he hadn’t experienced since before he moved in with her and became her full-time slave. He’d have her blindfolded and naked on the bed, tied to the posts, while he stroked and teased her with the flogger, whipping her into a frenzy. But he’d be in control. She’d be the one begging for release, for permission to orgasm, and he’d hold that power in his hands.
“Little mikey, time to get dressed for the party,” came her seductive whisper in his ear, and he shuddered his way out of that delightful little fantasy. Her hand grasped his firmly, and he walked behind her as she led him back toward the bedroom. “Did someone make messes?” she cooed.
“No Miss Sally,” he replied confidently. Oh, he’d come right to the edge, for sure, and it wouldn’t be difficult for her to push him over it in the state he was in right now, but dammit, he’d controlled himself!
“No?” she replied, genuinely surprised. “What a good little boy!” she cheered. Mike warmed with pride as Sally stood him at the foot of the bed. “Time for little mikey to get naked!” she chuckled.
Mike quickly stripped, including his underwear, even more puzzled at what she had planned.
“Little mikey loves Mommy’s Lolly dress, doesn’t he?” she whispered as she nudged him down onto the bed.
“Yes Miss Sally,” he replied, confused at her new self-reference. Mommy? What’s that about?
“Of course he does,” she continued, grabbing the pump bottle of lotion and the tube of rash cream. “Lie still now, let Mommy take care of you.” Mike’s eyes widened behind the blindfold as she worked the strange but familiar-smelling substances into his nether regions and around his thighs, then rolling him on his side and doing likewise with his bottom. His erection had weakened considerably in the confusion, more than a little fearful of all this sudden sensuality, and baffled by the smells he couldn’t quite identify.
The next thing he felt was a cooling sensation on his buttocks, followed by another very familiar smell wafting to his nose. By the time he heard the fateful rustling of plastic, the puzzle pieces began to fall into place, and panic shook him as he realized she was taping him into an incredibly thick disposable diaper which now was latched snugly around his middle. “Mommy, please, no more!” he cried out, invoking the safe words for the first time in months.
“Uh-uh. Remember our bet, little mikey, no safe words tonight,” Sally cooed softly. “You’re mine, to do with exactly as I please. Mommy needs her little baby to stay clean and not make messes everywhere tonight, so this is what the baby is going to wear. Understood?”
Mike’s face was red-hot with humiliation on a level he’d never imagined possible, and to his surprise, his erection returned with a violent vengeance. Terrified to move, he whimpered, “Yes Miss Sally.”
“Nope. Tonight, my name is Mommy, and that is how you’ll address me.”
“Y… yes Mommy,” he stammered.
“Good. Now for the rest of your costume! Stand up, baby.” Mike complied silently, trembling as the thick padding beneath him rustled in response. A much louder rustle came from the vanity, and his mind reeled at the possibilities. Sally grasped his leg and picked it up, causing him to nearly lose his balance, and plunked it in the middle of a huge amount of material. The other leg followed, and he began to realize that the mountain of satin she was sliding up his legs had no pants. Worse yet, it didn’t stop at his waist. He was near tears as his arms were guided into the puffy short sleeves of what he now realized was a very elaborate dress, one that, as near as he could tell, ended just a few inches below the bottom of his… the diaper. She intended to take him out like this? He wobbled as his brain started to shut down from the stress of it all, and Sally caught him.
“What’s wrong, baby?” she cooed.
“Miss…. Mommy… I don’t…” he was afraid to answer. Would she punish him for complaining? Would she somehow make this even worse than it already was?
“No safe words, no limits,” she whispered in his ear. “Mommy knows what little mikey wants, what he needs, and what he can handle. Tonight, little mikey is going to be little michelle, an adorable little baby girl who isn’t potty trained. And Miss Sally is going to be Mommy, and we are going to be the absolute life of this Halloween party. Aren’t we?”
“Y… yes Mommy,” he whispered.
“Good. Now it’s time for Mommy to do little michelle’s hair and makeup so she can be super adorable. And little michelle going to keep her eyes straight ahead until Mommy’s all done, or else little michelle’s going to have to be disciplined right before we go to the party, and little michelle doesn’t want that, does she?”
“No Mommy!” he said, much more assertively. His diaper rustled as he flinched, but it was just Sally taking his blindfold off. He faced the window, his eyes locked straight ahead, fighting with all his strength not to look down as Sally began to tug his hair this way and that, brushing and tying and humming merrily. He felt thin strips of cloth drape down his temples, teasing his imagination even further as Sally appeared in front of him with a makeup kit, dabbing on his cheeks, on his eyelids, and finally applying lip gloss to his trembling lips before she stepped back and smiled approvingly. “Hands out,” she insisted. He held his palms out to her, and she turned them over. He knew what she was about to do even before the powerful smell of nail polish wafted up to his nose. She was quick and efficient, hitting the nails with a blow dryer to speed the curing process before turning her attention to his feet, sliding long knee socks up his calves and buckling what thankfully were some sort of flats onto his feet.
The anticipation was killing him, but his eyes stayed fixed on a tree outside the window, examining its twigs and branches and leaves as she worked. She popped up, looked him up and down, and smiled broadly. “Perfect!” she declared. “Little michelle ready to see how pretty she looks?”
No, he wasn’t. But he was. Desperate to see, but terrified. “Yes… Mommy,” he whimpered, trembling as she took his hand, stood him up, and walked him into the closet, turning him to face the full-length mirror. What he saw was horrifying, humiliating, and erotic beyond his wildest imagination. There stood a girl of not much more than nine, blond hair in adorable little pigtails tied up in pink ribbons that cascaded down just in front of her ears, with blushing pink cheeks, soft purple eye shadow, and candy pink lips, all of which perfectly coordinated against the pink satin romper that cascaded down her chest, with little purple teddy bears dancing along its hem, which landed just above her knee. The little girl in the mirror’s bottom lip trembled as her eyes darted around, noticing all the subtle details of her outfit, from the puffy white sleeves of her blouse to the delicate pink bows on her knee socks and the bright brass buckle of her pink Mary Janes.
And Mike’s erection strained against his padding. Painfully. Agonizingly. The little girl in the mirror shifted uncomfortably, and her diaper rustled in response, but not as loud as her romper dress as it twirled subtly with each of his movements.
“Aren’t you the prettiest little thing?” Sally said as her face appeared next to the blushing little girl’s face, Sally’s hands clasping on her shoulders while Mike felt the weight of anvils drop onto his. The little girl’s knees buckled a little, but she kept her feet.
“Yes… Mommy…” the girl mouthed as the words escaped Mike’s lips.
“No no, tell me what you see, baby.”
“I’m… a… pretty little girl, Mommy,” the girl said, in Mike’s voice.
“Yes you are. Oh, and look – even your little underwear is coordinated!” Sally reached down, and the little girl fidgeted as the front of her dress came up to reveal a huge pink diaper, with little silhouettes of princesses in dresses, purple and blue, with little purple and blue stars and hearts dancing between them. “Don’t you love your new underwear, baby?” she whispered, pressing her hand against Mike’s manhood and stroking up and down.
The girl in the mirror bucked and strained at the touch, her mouth gaping subtly as her eyes widened and rolled back, and seconds later, Mike came.
Almost immediately after the orgasm was over, to his horror, Mike peed uncontrollably.
Sally grinned widely as Mike’s diaper first began to twitch and spasm, then slowly warm and swell. The spell had taken effect, but the real magic was just beginning. And, thanks to his delightfully thick and noisy underwear, Mike would be blissfully unaware of what was happening.
“Oh my, did my baby girl have an accident?” she cooed. “Does she need her little diaper changed already?”
Mike was still entirely too stunned to process the situation, and he automatically responded, “Y… yes Mommy!” His orgasm had been powerful, nearly mind-blowing, but as shocking as the loss of bladder control was, the sensation that accompanied it had eclipsed the ejaculation. He nearly passed out from the intensity of the feeling of hot urine pouring out of him, spilling down the front of his member, and being absorbed by the thirsty padding surrounding it, which swelled in response, heightening the pleasure. And now, confused, terrified, but overwhelmed with an endorphin rush like he’d never experienced before, those were about all the words he was capable of forming at this point. His legs wobbled as Sally led him out of the closet and back to the bed.
“My goodness, isn’t it lucky Mommy decided to get her baby girl new underwear for this party!” Sally scolded playfully as she gently pushed Mike back down onto the bed. “Your pretty new dress would be ruined, wouldn’t it?”
“Yes, Mommy,” came the meek, unsure reply.
She flipped the skirt up and ripped the tapes loose as he lay there, limp as a ragdoll. “Oh my my my,” she said. “What a mess my baby girl has made! Maybe Mommy needs to get the cock ring tonight, or we’ll be changing diapers all night long, huh?”
“No Mommy!” he pleaded, panicked at the idea of having to wear that accursed thing.
“Aw, it’s okay, baby,” she soothed as she took a cool wet wipe and cleaned up his rapidly sagging penis, stifling a laugh as he shivered at the touch. “Mommy’s not going to spoil your fun tonight, as long as you’re a good little girl.”
“I’ll be good, Mommy! I promise!” Desperation had driven his voice to a near squeak, and it was a struggle for her not to burst into peals of laughter.
“You’ll be a good what?” she prodded.
“I’ll be a good baby girl!”
“Alright, then. No nasty cock ring for my sweet little baby Michelle. Just a nice clean diaper to keep her little messes where they belong.”
For Mike, this was just yet another round of conflicting feelings rolling into the raging storm within his mind. He hadn’t even begun to process the fact that he was to be paraded about like this in front of God knew who, likely a large number of Sally’s friends and associates. But the idea of spending the next seven or eight hours strapped in a cock ring while experiencing this previously unfathomable level of humiliation, knowing how excited he was already getting by it, was unconscionable. So there was relief as Sally changed his… the diaper, but the fact that it was being replaced by another just like it, one that he would have on at the party, one that was at great risk of being exposed, considering the length of this… oh god, this DRESS, this dress that looked like it belonged on a kindergartner going to her first fancy party… His thought pattern spiraled out of control once more, and his mind feebly grabbed hold of the only comfort available, that of the soft, dry padding Sally was now wrapping around his middle. Comfortable, soft, like a great big hug around his crotch. Clean. Dry. Comfortable…
“Now, if you have to go potty again when we’re at the party, Mommy expects you to ask, baby,” Sally’s admonishment stunned him out of his thoughts again. “Just because you’re wearing a diaper as part of your costume, doesn’t mean Mommy wants to be changing wet and dirty diapers all night,” she added. Of course, that was exactly what she already knew she’d be doing, but he didn’t need to know that.
“Yes Mommy,” he mumbled.
Mike was too much on autopilot, Sally decided. She needed to snap him back into the present. She sat him up and flipped the hem of his dress back down, spreading it across his thighs. “So, what does little michelle think of Mommy and baby’s costumes?” she prodded.
“I… I…” Mike could scarcely process the question, never mind answer.
“Is Mommy pretty?”
“Yes! Mommy’s very pretty! I love your costume, Mommy!”
“Is baby michelle pretty?” she asked slyly.
“I… yes… I’m… pretty too, Mommy…” he offered with much less conviction.
“Yes you are, baby,” she encouraged. “Do you like feeling pretty?”
The noise in his head suddenly quieted on this singular question. Do I like this? “I… I don’t know, Mommy…”
Sally was determined. With an arm around his waist, she pulled him back to a stand and took him back to the mirror in the closet, standing beside him smartly. “What do you see, baby?”
“I see…” Mike knew the answer, but forming the words was hard. Admitting it was hard. “I see a beautiful Mommy and…” he trailed off.
“And an adorable little girl.”
“That’s you, baby. How does it feel to be an adorable little girl, with a pretty dress that matches her Mommy’s dress, all ready to go to a party?”
Indeed, the pink accents in Sal… Mommy’s dress set off perfectly against Mike’s bright and colorful outfit. He was adorable. He wasn’t really Mike anymore, at least not where anyone could see, he was Michelle, an adorable little girl who just peed in her diaper and enjoyed it. And enjoyed her Mommy changing her diaper, and very much enjoyed being in a dry, clean diaper now. And he was positively terrified of what the evening held in store for him. But in this strange moment, in this brief calm amid the storm, he finally found an answer to this question.
“I love you, Mommy. Thank you for my pretty party dress… and my pretty new underwear… and for cleaning up my messes for me…”
“You’re very, very welcome baby,” Sally said, wrapping her arms around him and kissing him on the cheek, careful to avoid the heavy blush she applied earlier. “Mommy loves baby michelle too. And Mommy and baby michelle are going to have so much fun tonight! You just wait.”
And at that moment, he knew his answer was the right one.
5Two hours later, as Sally led him out to the Escalade, wobbly, slightly bow-legged, and back to being a nervous wreck, Mike wasn’t so sure of that answer anymore. Sally touched up his makeup before they left, reassuring him the whole time that this was going to be the most fun Halloween party ever. But deep inside, he was quite sure that fun she spoke of would be had by others, at his expense, far more than he would be enjoying himself.
Of course, Sally knew otherwise. Yes, her little pet was going to be humiliated tonight, but that was largely going to be his own doing. Between the magic she had woven and the plans she’d already made with other party-goers, little mikey was going to have the time of his life in between the blushing and the self-consciousness. And, Sally felt certain, little mikey was going to take rather well to being little michelle on a more permanent basis.
“Wait… what are we doing here?!” Mike protested as they pulled up in front of the strip club. It wasn’t long ago he’d been a regular here; the last thing he wanted was to be seen like this by people that might recognize him!
“Relax, baby,” Sally chided. “It’s a private party. Invite only. None of your little drunk friends from back then will be here, only our best customers, the girls, and us.”
“Has Mommy ever harmed you, baby?” she cut him off swiftly.
“You are going to have the time of your life tonight, baby, so long as you play the role your little costume is supposed to convey.”
Truth be told, he felt like a scared little girl right now, vulnerable, afraid. “I… Yes Mommy…” he stammered.
“Mommy’s not going to let anything bad happen to you tonight, baby. I promise.” She turned his trembling chin to face her. “Do you believe me, baby?”
“Y… yes Mommy…”
“No you don’t,” she scolded gently. “What has been the nature of our relationship up to this point, Michael?”
Mike was stunned at this very sudden and very serious question. “You… you’re the Domme, I’m the subbie,” he ventured.
“It’s much more than that, and you know it,” she replied curtly.
“You’re my Mistress, and I am your slave,” he admitted. “I live to serve you.”
“Yes, and every step that we’ve taken together on that journey has involved me showing you secret desires you never knew you had, right?”
"Tonight is a very special night, Michael. Not only are we dressing up in fancy clothes and going to a party, but the very nature of our relationship is different tonight. Tonight, instead of servicing my needs and desires and forgetting your own in exchange for my affection, I am taking care of your needs and desires. Tonight, in exchange for making yourself vulnerable, for willingly giving me control over every aspect of your being, you will want for nothing, and I will give you pleasure without pain, and I will show you more secrets in your heart that you didn’t know were there, but I always have.
“Do you remember what you saw in that mirror today?” she continued.
“Yes… Miss… I mean… Mommy… I mean…” Mike was confused by the way Sally addressed him, but more overwhelmed by her words, the realization of how she had been treating him since she taped that first diaper around his middle.
“What did you see, baby?” Sally said, leading him back where she wanted him to go.
“I saw… a pretty little girl…”
“You didn’t see a man dressed up as a little girl?”
“That’s right. And neither will anyone else at this party, so long as you be that little girl tonight. Be the little girl who needs her Mommy to do everything for her, and no one will ever know that little baby michelle is really little mikey, Miss Sally’s slave boy. And just for tonight, Mommy will spoil her little girl rotten. How’s that sound?”
“I… I think I’d like that, Mommy,” he managed. Well, he liked the parts about Sally taking care of him, and he liked the idea of her spoiling him for a night anyway. Be the little girl in the mirror. It was a simple request. The little girl in the mirror was wearing thick diapers under her party dress because her Mommy didn’t want her to have accidents and make messes. And she’d already had an accident and made a mess that evening. So clearly she needed them. Her Mommy was right.
“I have one more thing to add to your little costume,” Sally said, reaching into her purse. “I think you’ll find it very helpful to calm your little nerves and remind you to be that adorable little baby girl.” Out came a pacifier, with a white mouth guard and a powder-pink ring. Attached to the ring was a delicate-looking strip of lace, and on the other end of that strip was a pastel purple suspender clip. Mike blushed deeply, but didn’t argue as Sally attached the clip to his collar, leaving the pacifier to dangle at his chest. “Now, when you feel scared, or nervous, or excited, or confused, you just suckle on that, and it will help you calm down. I promise. Right now, though, we don’t want to muss up your pretty pink lipstick unless we absolutely have to, do we?”
“Good girl. You sit right there and Mommy come get you, okay?”
And with that, Sally exited the driver’s side, swiftly came around to the passenger’s, and, to Mike’s surprise, hoisted him off the seat, plunking him on his feet next to her before closing the door. She grasped his hand and tossed the keys to the waiting valet, who chuckled a bit before climbing in and driving off. “Baby walk with Mommy, or shall I carry you?” she teased.
“I’ll walk, Mommy!” he squeaked.
The bouncer at the door smiled broadly as he held it open for them. “Good evening, Miss Sally,” he boomed in a deep baritone voice.
“And to you, Travis,” she replied, tucking a twenty into the pocket of his smart black button-up shirt.
“Thank you, Ma’am,” he said as Sally led Mike through the door. She set an easy pace for him across the lobby, thankfully, but even so he found himself stumbling as he tried his best not to waddle in the thick undergarment, feeling very self-conscious as he and Sally were fawned over by the hostess. He recognized Jennifer immediately, recalling the fantasies he’d even had about her before Sally swooped into his life, and inside he worried that she remembered him as well, despite Sally introducing him as her cousin and assuring the striking beauty that “she” was indeed of legal age, despite the costume.
The music from inside the bar was booming as Geoffrey stepped aside and opened the door for the pair, and Mike suddenly felt very lightheaded as they walked into the chaotic scene. His knees buckled, and the world began to spin.
“Michelle? Are you okay?” Sally’s worried voice rang in his ear.
“I… I’m not sure… Mommy…”
"Healing thoughts sent in flight,
bring the brightest of blessings this very night,
Surround my child with healing light,
As above, so below."
The words whispered through Mike’s mind as he opened his eyes and found himself sitting on a couch just a few feet back from Pervert’s Row. Sally sat to his left, an arm around his shoulder, her other hand on top of both of his, which were in his lap. To his right, another woman he didn’t recognize, in an elaborate fairy costume complete with wings and a tiara atop her straw-colored hair, had her hand atop Sally’s. A third woman, donning tiger stripes and painted-on whiskers across her ebony cheeks, was at his feet, her hand atop them all. These couldn’t be dancers who worked here, unless they’d been hired in the six months or so since he became Sally’s pet, since the last time he’d been in this building.
“Well hello there, cutie-pie!” Sally cheered as he opened his eyes. Smiles and chuckles surrounded him as he began to get a grip on his surroundings. “Did someone get a little dizzy?”
“Yes, Mommy,” he managed, which brought delighted squeals from the other two women.
“Oh my god, you are just so freakishly adorable! I want one, Sally!”
“Me too! Where on earth did you find her?!”
“Hush, ladies, the poor thing is just getting her little bearings!” Sally scolded. “Michelle, I want you to meet my very special friends, Suzanna,” she paused, and the one directly in front of him offered a little wave, “and Rachelle.” The one to his right grasped his arm and gave it a squeeze. “They were very helpful when you had your little spill back there. Can you say hello?”
“H… hello Suzanna… and Rachelle…. thank you… for helping my Mommy take care of me…”
That resulted in another round of squeals, not to mention two hugs that seemed awfully close to inappropriate to Mike, both women pulling his head directly into their chests as they praised him for being such a polite little girl. Mike looked nervously at Sally, fearing some repercussion for such sexually forward behavior, but she seemed unfazed by it. Of course, he found himself with another erection as a result, and couldn’t help but squirm a bit as the two women took their leave, flitting off into the crowd together laughing and joking. This was really the first chance Mike had to get a look at the crowd. The first thing he noticed was that the vast majority of them were female. There had to be a hundred or more people in here, and he could count the number of men that weren’t employees on two hands! Some of them he recognized; he’d seen them on stage plenty, but most were complete strangers, with or without masks, in their elaborate costumes.
A waitress appeared out of the midst of the crowd, a tall brunette in an absolutely perfect replica of a Playboy Bunny outfit. She greeted Sally with respect, but fawned all over Mike, just like the others had. “So what are we drinking?” she asked after she’d gotten a pinch on Mike’s cheek, making him blush again.
“Cosmo for me, Maker’s and coke for this little cutie,” Sally replied, leaving Mike stunned. He hadn’t drank bourbon since he was a regular here; at most he’d have a glass of wine with her when she allowed it. How did she know that was his usual?
“Oh my goodness, what’s a little angel like you doing drinking a big grown-up drink like that?!” the waitress chirped. “Sure you wouldn’t rather have a Shirley Temple?”
Mike shook his head with a cringe. “She’s very fussy,” Sally offered, “and she’s in the party mood tonight, isn’t she?” Sally turned to him expectantly.
“Yes Mommy,” he mumbled. Once upon a time, getting this much attention from so many beautiful women would put him straight over the moon, but dressed as he was, under the watchful eye of his Misstress… or… Mommy, he felt like he was under a microscope, and in the back of his head there was still a nagging voice that said they all knew, they all could tell that it was the grown man everyone knew as Mike underneath all these ruffles, and they all knew what he had on under the dress, too.
Of course, Sally knew what was rattling around in Mike’s head as well. But she had bigger plans in store, plans that necessitated getting a few stiff drinks in him, before the party could hit its… climax.
Half an hour later, just after the waitress brought their second round, Mike finally seemed like he’d settled down a bit and at least gotten accustomed to the steady stream of party-goers greeting Sally and complementing them on their costumes, some more emphatically than others. It was time for the second act of this little play. She stood up and smiled down at him. “Alright, baby, Mommy has a little thing she needs to take care of. You be good girl while I’m gone?”
Mike was horrified. “Wait, where are you going, Mommy?!” he whined.
“The girls are going to dance for our VIP guests tonight, and I need to emcee for a little bit. I won’t be gone long, I promise.”
“But… what if I have to go to the bathroom?” he whisper-yelled, trying not to make a further spectacle of himself.
“Oh don’t worry. If you can’t wait until Mommy gets back, she has spares in her purse,” She patted her large handbag sitting next to him on the bench, kissed his forehead, and strode off through the crowd, then reappeared climbing the back stares onto the tall podium, thirty feet above the floor below, a number of girls following after and lining up at the stairs leading down onto the lighted stage. Morbidly curious, Mike peeked into the bag. Sure enough, there at the bottom lay two huge diapers and a travel-pack of wipes. He closed it up quickly and very self-consciously tugged at the hem of his dress. He tried to close his legs, but the bulk between them was far too massive for that to be comfortable. Crossing them was no help either, so he sighed and took a sip of his drink, blushing fiercely as he looked around the room.
“Ladies and gentlemen!” Sally boomed into a wireless microphone, and the crowd quieted. “I want to thank you all for coming to our quiet little get-together here tonight. Hope everyone’s enjoying themselves!” A loud cheer erupted in response. “Wonderful! Well, of course, here at the Atlantis, it wouldn’t be much of a party if we didn’t have dancers, would it?” More rowdy approval from the crowd. “Then by all means, let’s hear it for Mandy and Melissa!” Another cheer rose, and the twins he’d seen grace this stage so many times together strutted down the staircase in matching sea-blue two-pieces with feathered masks across their eyes. Whistles and catcalls rose up from Pervert’s row as the two girls went into their well-rehearsed routine, and Mike, for the first time all night, managed to forget himself a little bit as he sipped his drink and stared at the beautiful bodies writhing in sync on the twin poles at center stage, then taking their turns attending to the dollar-waving men and women on Pervert’s Row.
Sally’s watchful eye remained locked on her fidgety little charge as she called off several more acts, a parade of women strutting down to the stage, working through their various routines, collecting their tips, then exiting directly into the crowd to offer their attention to those who weren’t close enough to get a proper show. She smiled as he went rigid when she called the next name, “Tiger Lilly!”
Aiko, or “Tiger Lilly”, wasn’t your average dancer, and while the crowd always found the Asian girls exotic and tipped them well, was hardly an average Asian girl. Tall, well-busted, and very toned, her acrobatic act on the pole was as big an attraction as her forceful dance routine, projecting her aggressive femininity that made the horny toad regulars melt in their seats. Of course, there was only one such “regular” in this crowd, and both Sally and Aiko were well aware of this fact. So while Mike trembled in his little dress and pigtails, Aiko locked her eyes on him during her entire set, save the few minutes she spent gathering up bills off the stage floor before exiting.
Mike, meanwhile, was transfixed while Tiger Lilly danced. He felt those eyes burn a hole straight through his middle, this powerful woman who molested him so many nights at home in his bourbon-soaked fantasies. And then, as she strutted down the side-stairs off the stage, the unthinkable happened. He quickly realized, he wasn’t just imagining Tiger Lilly staring at him, she really was, because she came straight for him once she hit the floor, in her leather bikini bottom, the top having been discarded during her routine, and her fishnets and knee-high boots. He trembled as she closed in and bent down to his eye level, a few tiny inches from his face.
“Are you being a good little girl?” she asked him seductively. Mike mouthed a few things, but all that came out were gasps, so he nodded his head nervously, his erection raging inside his diaper. “I bet you’d rather be a naughty one, wouldn’t you?” she asked, looking up and down his chest. Mike shook his head fiercely. “No? Then I guess I’ll just have to be naughty by myself, huh?” A rapid nod. “Here, have your little binky, baby, while Tiger Lilly gets naughty on you,” she said, picking up the pacifier and tucking it into his mouth as she mounted his lap, shoving her ample breasts into his face as he suckled furiously on the nipple and whimpered both his appreciation for this attention and his fear of Sally’s repercussions later. Her hips ground against his thighs, and she massaged his face with her tits first, then grabbed him fiercely by the chin and licked his forehead. “What a good little girl you are,” she whispered in his ear before licking it, which drove him half out of his mind. Without warning, she reached under his dress and, as he cried out in protest from behind his pacifier, grasped the front of his diaper and began to grind it up against him. He squealed as she pressed her tits back into his face, hot humiliation amplifying the intensity of her sexual aggression, but to his shock, she didn’t back off, she didn’t even seem phased at his underwear. “Wittle baby like it when I do that to her?” she asked, pressing the soft padding hard against his throbbing member and stroking it while her whole body moved in rhythm.
If Mike hadn’t just had an orgasm a couple hours ago, he would have probably had one immediately right then and there, if not sooner, but instead Tiger Lilly just worked him over, teasing and stroking and grinding and squeezing until finally it happened. Except something was very wrong. Last time, it seemed as though he started peeing as soon as he was done. This time, he wasn’t even finished before the flow began, and it seemed to heighten his orgasm even further, causing his whole body to shudder as his diaper grew hot and swelled. He whimpered and squeaked behind the mouth guard, biting down hard on the nipple as Tiger Lilly whispered, “Guess you were a naughty little girl after all, weren’t you? I knew you could do it. I’ll see you later, pretty little baby girl.”
And with that, Aiko dismounted him and left him there. Breathing heavy, with beads of sweat and Tiger Lilly spittle running in rivulets down his cheeks, Mike couldn’t even begin to process all the things that were wrong with what just happened. He dropped the pacifier out of his mouth and drained the half-full drink sitting next to him, safe and sound in its little cup-holder, and his waitress appeared seemingly from nowhere to replace it with a full one. “Th… thank you…” he stammered, taking a sizable swig and setting it down.
Sally, meanwhile, smiled from her perch on the scaffold and nodded approvingly. “Oh, little Michelle, the fun is just beginning for you, baby girl…”
Mike finally got his wits about him after another drink, and he returned his attention to the girls on stage, though he was far less engaged now, his diaper rapidly cooling and the stickiness from his orgasm still pressing against his skin, which was decidedly uncomfortable, powder and cream or no. He’d managed to get his dress back down before anyone had seen the diaper, or at least if they had, no one had taken any notice of it. The swollen mass between his legs pressed them even farther apart now, to where he had no choice but to spread them in a decidedly unladylike fashion. As a result, he found himself fidgeting with the hem of the dress quite regularly, pulling it down in his lap, praying no one could see the embarrassing underwear, especially now that it was wet.
Meanwhile, Sally was drinking this all in with sadistic pleasure, watching the pitiful thing’s eyes dart to and fro, making himself completely obvious with all his grabbing and pulling. She was so fixated, she had to continually remind herself to keep at least one eye on the girls so she didn’t miss her timing on announcing the next one. By the time the waitress brought Mike his fourth drink a mere thirty minutes later, Sally decided he was ready for another round of something else. She whispered something to the tall, buxom blonde standing third in the line, then stepped out to announce her.
Mike’s eyes bulged as that name was called; Svetlanna, the Moscow Mistress as she was known, was a nearly burly woman, formerly a competitive weightlifter, though she had long stopped her bodybuilding routines in favor of allowing her once-ripped physique to soften a bit, presenting a well-chiseled but still feminine appearance. Most of her act was demonstrations of her strength, regularly and effortlessly dragging denizens of The Row up onto the stage to be used as her playthings during her act, climbing the pole and hoisting them up with her under their arms while she held on with her legs. Oh, and the girly boys all loved when she’d incorporate bodybuilding poses into her act. So did Mike. He used to dream of her having her way with him, pinning him to the bed, tossing him around like a rag doll while he helplessly submitted to her whims and demands. All those little fantasies came rushing back as the fierce blonde stormed out on stage and began her performance.
It took a little doing to get Svetlanna here tonight, on account that she had moved across the country several months before, but for Sally it was worth every second of what was about to happen. The woman’s routine was short and sweet, skipping over her usual drafting of volunteers, and when she exited the stage, she too made a beeline straight for the trembling sissy. Sally’s only regret was that she didn’t add a wireless mic to her little slave’s costume so she could hear the exchanges.
“Vat in the world is a dainty little girl like you doing in such a place?” Svetlanna demanded in Mike’s ear as she straddled his lap, a fistful of his collar locked firmly between her fingers.
“I… I…” Mike couldn’t even form words at this point, his mind reeling as this incredibly powerful woman leered in his face.
“I should take you over my knee for being such a naughty thing! But you’d like that, wouldn’t you?” she growled low. Mike could only nod his head as he trembled under her grip. She shoved him back into the seat and slapped him across the face with her tits. The force of the blow took Mike by surprise, and he cringed a bit, even as his member, barely recovered from being molested by Tiger Lilly, jumped right back to attention.
“Oh yes, you’d just love it if I took you right up on stage and spanked your naughty little bottom in front of all these people, wouldn’t you? That’d be the thrill of your life, wouldn’t it?”
He shook his head fiercely in panic. No, the last thing he wanted was to show what by now had to be two hundred people his soggy, diapered bottom.
“Vhat’s wrong, naughty little girl? Are you worried someone might get a peek at your naughty little lady parts?” She pushed right past his trembling hands in his lap and made a grab between his legs, catching a squishy handful of plastic. “Oh, so you’re vorried about everyone finding out what a little baby you are, is that it? And a very wet little baby from what I can tell. Perhaps Mama Svetlanna should take you to the back and change your soggy little diaper for you?” she sneered as Mike helplessly gaped, mouth wide open, trying to form words. “Vood you like that, little baby girl?” She began rhythmically pressing the sodden mass against Mike’s raging erection as she continued, “Oh, yes, I’m sure you’d love for Mama to take your nasty diaper off and spank your naughty little bottom, wouldn’t you?” She slapped his thigh hard enough to elicit a yelp. “Varm that little ass right up, make the baby cry, then put a clean diaper on her, maybe make her stand in the corner for a while. But first, I should take that dress right off you and take you up on stage, show everyone vut a nasty little baby girl you are. How’d you like that, baby?” Another fierce slap, but this time Mike’s head was swimming as he neared yet another climax as she continued to grind the padding forcefully against him. His breath came in staccato gasps as she leaned in and bit his ear lobe. “That’s it, baby. Make Mama a big mess in your filthy little diaper. Go ahead. Do it. Come for Mama,” she chanted low. And Mike did exactly as he was instructed. Except…
Mike would have looked down if he hadn’t been pinned to the back of the bench by this hulking beauty, because between his legs, something bizarre was happening. What he felt was the intensely pleasurable sensations of an orgasm, but all that was coming out of him was hot urine, first in spurts, then in a steady flow, warming the sodden mass right back up. “Vut a nasty, nasty little baby you are,” Svetlanna sneered. She lightly slapped his cheek as he gasped for air. “Pissing in your little diaper while Mama tries to play vit you. Horrible, nasty little girl. You just wait, Mama will be back, to give you exactly vut you deserve, little brat.” She slapped him again, harder, then dismounted him and stalked away, leaving him in a heap on the bench, dazed, confused, drained, and humiliated, with his dress hiked up more than enough to show off his swollen plastic underwear to any passer-by who cared to look. Realizing this last part rather suddenly, Mike scrambled back into the most modest sitting position he could muster, pulling his skirt down and draining the last of his drink in hopes of steadying his fraying nerves. The booze was definitely getting to his head, but at this point, all he could do was pray Sally would get back here soon, take him into the back somewhere, and get him out of this disgusting diaper. Dear God, what would she do when she saw this much piss? She might force him to wear these things longer than the duration of this party! Worse, with the messes he’d made, she might put that horrible cock ring back on him as well! He shuddered at how angry Sally typically became when he came without permission. No, whatever reaction she had to his spew all over himself would surely be far worse. She’d thrash him for that, and there wouldn’t be any aftercare at all. Self-pity rose up in him as he accepted another drink unbidden from the waitress, dreading another night in the cage, probably more, unable to get comfortable on account of the welts he’d have on his backside.
Of course, Sally already knew what she’d be finding in that diaper. In fact, she knew more than he did. But let him squirm. Let him fear her wrath. Anticipation is half the fun, after all. She focused on finishing up the stage act, stealing occasional glances at him twisting around on the bench vainly trying to get comfortable with an inner tube full of his own piss wrapped between his legs, knowing the apex of little Michelle’s coming-out party was yet to arrive. And oh, when it did, it would be something for all involved to remember. But all that had to wait, sadly. And so Sally focused on trotting the girls out there, one after another. Forty minutes later, the first set was over. And act two of the transformation could now proceed.
The last girl left the stage to go troll for lap dance tips, which were surprisingly easy to come by; the women in attendance seemed to enjoy this sort of attention every bit as much as the scattered few men. Sally confidently strolled down the same stairs, smiling and waving and shaking hands as she exited the stage on the side opposite from Mike, content to let him stew in his own juices for a bit longer while she greeted guests and hobnobbed. She worked her way patiently around the perimeter before sidling up next to the still-blushing little whelp with a smile. She could see in his eyes that he was either outright drunk or not far from it. Perfect. Disinhibition would make things move just that much smoother.
“And did my baby girl behave herself while Mommy was gone?” she chirped.
He nodded. “Yes Mommy,” he offered weakly.
She feigned surprise. “Are you sure? You sure are acting like a little girl who got into trouble. Do we need to go potty?”
He blushed deeper, and his head dropped further. “No Mommy.”
She leaned in tight and whispered, “Does that mean we need a diaper change?”
“Y… yes Mommy.” She drank deeply of his humiliation, savoring his agony at this admission. But she wanted more.
“Then someone needs to ask Mommy nicely, unless that someone wants to sit in a wet diaper all night.” Her whisper was seductive, but with a subtle edge of menace, just enough to spur him into action.
He looked up at her with pain in his eyes, but her face remained steely. “I… I mean… M… Mo… Mommy…” he choked on the words, and she had to fight hard to suppress her smile.
“What is it, baby?” she said firmly.
“W… will… you… pl… please… change my… d… di… diaper Mommy?” Glorious. Even all the booze he’d soaked up couldn’t stop tears from forming in his eyes.
“Oh, don’t cry, baby girl,” she cooed, wiping them away with a flick of her thumb, “Mommy get you all cleaned up in a jiffy. Let’s see if we can find someplace nice and quiet.” She grabbed her purse, latched onto his arm, and nearly jerked him to a stand. “Keep your chin up, baby, unless you want everyone to figure out what we’re doing,” she admonished as she led him through the crowd into one of the private dance rooms.
“Now lie down, sweetie,” she instructed. He was very, very slow and deliberate, bouncing his eyes between her and the floor, and she knew why, but she doubted he was ready to admit it. “Unless we don’t want a diaper change after all?”
“I do Mommy!” he said quickly, dropping to the ground and lying back, eyes averted from her. She pulled the wipes, powder, and one of the spare diapers from her purse, reveling in his fear. He flinched as she ripped each of the tapes loose and pulled it down. He had certainly made a mess of himself, but she had to work at putting on a facade of shock.
“You weren’t a good girl at all, were you?!” she snapped, swatting him hard on the thigh.
“I’m sorry Mommy! The… the girls… they just came over and…” he begged.
“Oh sure, blame it all on the other little girls at the party!” she cut him off. “Dirty little thing! I ought to get my strap!”
“Please don’t, Mommy!” he groveled. “I’m sorry!” He covered his face with his forearms, cowering.
Another sharp swat to the thigh. “You should be sorry! Any other night of the year, I’d have you out there on the cross in just your nasty little diaper and a ball gag! Be lucky it’s Halloween, little girl!”
Sally was struggling not to laugh at this point as she quickly wiped down his now even smaller penis, paying special attention to the tiny, newly formed slit behind his tiny balls, which triggered a gasp from him and brought what was left of his dick to attention. She swatted his thigh again. “Nasty little thing, you think Mommy’s here to tickle your dirty little pee parts?!”
“No Mommy!” he yelped back, quivering. The erection subsided as quickly as it arrived, meekly disappearing into what now looked like the genitalia of a grade-school boy, certainly not a grown man.
She quickly finished the job, powdering him thoroughly and taping him up, tossing his used one in the trash casually. She softened her tone then, grabbing his arms and pulling him into her lap. “It’s alright, baby girl, Mommy knows how hard it is to be good all the time,” she whispered, rocking him and patting his bottom loudly and obviously. “Aren’t you glad Mommy made you wear diapers to the party?”
“Yes… Mommy…” he muttered. And truly, after all that happened, Mike was grateful. He was even more grateful to be in a dry, clean one now, but he was confused at how erratic Sally seemed to be behaving. At first he was sure she was going to savage him. Now she was suddenly all gentle again. His booze-addled brain couldn’t process her moods, not that he was any better at it sober, so he dismissed the thoughts and just soaked up the attention.
“Of course you are. Now, Mommy has to go and pay the girls, baby. Would you like to go back out and sit on the bench, or stay in here where it’s safe and quiet?”
“Could I stay here?” he asked hopefully. With the girls prowling around out there, and as forward as they seemed to be tonight, despite him not even having cash to tip with, the idea of accidentally crossing Sally again was downright terrifying.
“Of course you can, baby. Why don’t you go sit in the nice comfy chair and wait for Mommy to get back so we can go have fun together?”
As Mike quickly scrambled into the plush chair in the corner of the room, Sally packed the supplies back into her purse and stood up. “Now be good girl while Mommy’s gone, okay? I’ll send the nice waitress to get you another drink.”
“Yes Mommy,” he said confidently, “I’ll be good!”
I’m sure you will, Sally thought to herself as she strode out the door. Too bad there are so many naughty girls here who won’t.8
Outside, Sally waved to the waitress, who nodded her acknowledgment and turned back to the bartender. She made her down to the dancers’ dressing room. Of course, Svetlanna and Aiko were there, chatting, and they both brightened when Sally entered.
“Everything will be ready shortly; he’s in number four,” she said, grinning subtly. The two women nodded and returned her smile, and Sally flitted through to her office for another, more important meeting.
Mike sat in the plush chair, drinking his I-forgot-th Maker’s and Coke, relieved to be away from the plying eyes out there, away from people who might see, might recognize him, might know that there was a man under this dress and diaper. For half an hour, the only person he interacted with was the waitress, and to her credit, she was damned attentive, bringing him two more drinks while he sat there, half trying to gather himself, half trying to inebriate himself to the point where he no longer cared. The latter half was winning this battle, for certain. In fact, he was getting quite comfortable in the soft cushions, sinking deeper, forgetting his modesty, when the door burst open, shocking him into a rigid stance, his knees pulled together as far as he could get them, what with the bulk of the (thankfully now dry) diaper between his legs.
In walked Tiger Lilly, a seductive smile on her face, with Svetlanna directly behind, both clad in skin-tight leather one-piece bikinis and tall boots to match. What was left of his feeble penis stood straight at attention as they marched in.
“Oh look,” Tiger purred, “It’s the naughty little babygirl I left in a puddle tonight. Did your mommy come and change your little diaper for you, baby?”
“I… I mean… Uh…” Mike stammered, but Tiger didn’t wait for an answer, darting straight over to him, lifting his dress, and slowly running her hand up and down his crotch, eliciting a loud crinkle from there and a series of gasps from him. “Oooooh, you’re all cleaned up, aren’t you, baby?”
“Zho vee can make her all messy again,” Svetlanna mocked as she approached, grabbing Mike by the chin. “Dirty little zhing, she’d much rather be naughty and messy, vouldn’t she?”
“N… n….” was all he could manage. Sally had been kind the last time she’d seen the aftermath of these two in his diaper, but certainly she’d be furious if it happened again! His protests were interrupted rapidly by Svetlanna’s lips on his own, and her tongue in his mouth as Tiger continued to stroke the front of his diaper. He could do little other than squeak as Tiger’s hand worked her magic, pressing the soft fabric against his tiny but very stiff and sensitive member.
Svetlanna finally released him from her kiss and licked her lips. “Naughty little zhing, you don’t need kisses, you need spankings, don’t you?” Without waiting for a response, she shoved her chest into his face, straddling his lap as Tiger backed off.
“Hey, I was having fun there!” Tiger protested as Svetlanna easily manipulated poor Mike’s head around with the slick leather corset.
“Ve don’t vant zhe babygirl to go filling her little diaper back up right avay, do ve?” She trapped Mike’s face and, as if for emphasis, flopped it back and forth as he moaned and squealed underneath. “Zat’s right, little girl, tell the big bad tiger that she has to be patient!”
“I’m… mmmmf… thirsty!” Mike managed, desperately trying to find a way to back the two dominating women off him for a minute and collect his scattering, increasingly drunken thoughts.
“You are?!” Svetlanna cooed. “Vell here, baby, drink up your little drink!” She grabbed his cup from its holder in the chair arm and roughly pushed it to his lips, tipping it up quickly. Mike tried to gulp it down as fast as she poured, but he helplessly choked, horrified as his neck and the collar of the dress got soaked. “Look at zhis messy baby, spilling her drink all over herself!” the Russian woman spat as she jumped off his lap. “She needs a bib!”
“Well of course she does, trying to drink out of a big-girl cup like that!” Tiger scolded. “Poor baby! Svetlanna, go find the waitress and tell her to bring us a washcloth so we can clean her up!”
“Fine, zhen!” Svetlanna sulked. “Both of you better behave yourselves while I’m gone, or zere vill be trouble!” With that, she stalked out of the room, slamming the door behind her.
From Mike’s perspective, even as bewildered and intoxicated as he was, he was also pretty certain trouble was already here. If Sally walked in on this mayhem, god only knew how many nights he’d be spending in the cage with a backside full of welts. He didn’t have long to dwell on that thought, though.
“Now that mean old Svet’s gone, Mama Tiger can take care of you proper,” the towering Japanese woman cooed, sliding into the chair and pulling Mike into her lap.
“I… Tiger… I…” he stammered.
“Shush you,” she interrupted, shoving his face into her breast and holding it there as her free hand found its way back under his dress. “Mama take good care of the baby girl now.” He squeaked and moaned helplessly as she massaged the front of his diaper. “There, isn’t that nice?”
After what seemed like an eternity of Tiger’s teasing, a knock on the door gave Mike a breath of air. “We’re a little busy in here!” Tiger sang.
“Special delivery!” It was the waitress.
“Oh, come on in, then!”
The waitress came in, but to Mike’s horror, she carried a pink baby bottle with a huge, oversized nipple attached on her tray, along with the requested washcloth. “Maker’s and Coke for the baby!”
“Oh thank you so much!” Tiger cooed, taking the washcloth. The waitress offered a curtsy as she grabbed the remains of Mike’s last drink, depositing the bottle in the cup holder and sashaying back out of the room. Tiger unbuttoned the front of his dress and slowly and seductively ran the warm washcloth from his chin down to his hairless chest and back.
“Tiger… please…” he begged, squirming at the stimulating sensations.
“Oh yes, Mama Tiger knows, baby girl is thirsty!” She tossed the rag aside, snatching the baby bottle up and tucking it into his mouth as he protested incoherently. “Uh-uh, drink it all up, baby!” she scolded.
Mike had no other option, really, what with the nipple steadily leaking into the back of his throat. God, if Sally saw him in Tiger Lilly’s lap; drunk or not, he needed to get this over with. He sucked furiously on the huge nipple, gulping the drink down as fast as he could, while Tiger offered encouragement. He was nearly finished when the door suddenly burst open, and he squeaked, shutting his eyes in terror.
To his surprise, however, Mike didn’t hear Sally’s familiar voice. Instead, it was Svet’s booming voice, “So, I leave for five minutes and here you are spoiling the little brat?”
“Aw, she was just thirsty, weren’t you, you adorable little thing?” said Tiger, popping the now-empty bottle out of his mouth and showing it to Svet.
“Vell good, at least she von’t be making any messes on the change of clothes I brought for her,” said Svet. “I’m sure Brianna vould be quite upset if you spilled your drink all over the pretty dress she vas nice enough to let you borrow for the rest of the evening!” Mike lay there, mouth agape, as Svet produced a spaghetti-strap pink satin babydoll. “Now, let’s get her out of that soggy thing before her Mommy sees what a mess she made!”
And then Tiger turned on him. Begging, pleading, and squirming, Mike desperately protested as the two women restrained him and removed the Lolly dress, leaving him in nothing but the pink diaper on his waist. His head was swimming now, though what was left of his penis was fully erect, creating a tiny but very obvious tent in the front.
“Well will you look at this, Svet?!” Tiger cackled, stroking the front of Mike’s diaper while pinning him against the wall. “This little girl has parts she’s not supposed to!”
“And she’s missing some parts too!” Svet added. “Look at that pathetic chest!”
“Please…” he begged. “I don’t… I can’t…”
“Shut up, sissy boy!” Svet cut him off, forcefully shoving the discarded pacifier into his mouth and giving him a solid slap on the cheek. Tiger backed off just long enough for Svet to pull the teddy over his head and push his arms between the straps. She slid in behind him, and Tiger wrapped herself around his front, staring fiercely into his eyes as the two of them began to grind on him, his still fully exposed diaper crinkling away as he squeaked incoherently into his pacifier.
“That’s it, baby,” Tiger whispered as his breathing quickened, “make a nice mess in your little diaper for Mommy!” Her hand clenched around his member while Svet reached under to stroke behind his sack.
Then it all happened at once. His bladder let loose as he reached climax, and his legs went to jelly, collapsing backward onto Svet. Meanwhile, the door burst open, and in walked Sally, a wry grin on her face. As the pacifier fell away from his face, the room began to spin, and he dropped to the floor, still peeing as the scene began to fade to black. The last thing he saw was Sally’s smiling face above him. “Looks like my little girl got good and naughty tonight, huh?”
Ere the dawn of the morning sun
Let past and future become one
This Samhain’s mischief ne’er to be undone
As above, so below
Mike awoke with a pounding headache, the sunlight boring into his squinting eyes like a power drill. What a bizarre dream that was! Sally, Tiger Lilly, Svetlanna, and those other two women… what were their names?! They were standing over him in a circle and chanting as he helplessly wet his… diaper? And then the part where he grew breasts and a vagina! Then Sally carried him into the house and changed him, then put him in a…
His hand reached out and touched wooden bars, and panic filled him. He must still be dreaming… right?! Both hands came to his chest and touched soft satin, which covered two small but very sensitive mounds of flesh. His eyes shot open, and he started to sit up. A rustle at his groin, and the feeling of plastic between his thighs filled him with horror. Then his bladder began to empty, accompanied by a powerful tingling sensation that sent shivers through him. He couldn’t even concentrate to try and stop the flow of moist heat spreading throughout his crotch area.
Now he was fully awake, headache or no, and his eyes were wide as saucers as they darted around, trying to process the scene before him. He was sitting in what had to be every bit of a six-foot-tall crib, painted a soft pastel pink. He still had on that pink babydoll from last night’s party, the pacifier still attached and dangling from the collar, not to mention a now very swollen pink diaper underneath. The room itself looked vaguely like Sally’s parlor, only all the furniture he used to clean on a twice-weekly basis was gone, replaced by a giant changing table with a small staircase next to it, this crib, an armoire, and a mysterious lidded wooden box, all painted the same pastel pink as the crib.
“Miss Sally!” he shrieked, terrified and confused. “Miss Sally, where are you?!”
Footfalls, getting closer. The door burst open. “Well good morning, little mikey!” Sally was grinning ear to ear. “Looks like someone needs a change!”
“I… I don’t want to wear diapers!” he said, forgetting himself for a moment. “What’s happening?!”
“Oh mikey, you’ve said that every morning since you lost your bladder control,” Sally replied as she strode toward the crib. Strange memories began to fill his head, memories of wetting his pants, of doctors saying things like “nerve damage” and “urinary sphincter” and “atrophy”. But how?!
“But Miss Sally, I’m a…”
“Mikey, I’m tired of telling you, you’re not allowed to call me that anymore! What is my name?!” Sally threw her hands on her hips and stood back from the bars. More recall, now of Sally demanding that he call her Mommy since she had to change his diapers for him like a little sissy baby. Of Sally fucking him with a double-dildo while he lay face down on a puppy pad, pissing all over himself as he climaxed.
“I’m… sorry… Mommy.”
“That’s better. Now, would you to come out and get your diaper changed and get dressed, or are you going to sit in there and pitch a fit?”
“I… I want to come out… Mommy…”
“That’s much better, little sissy boy.” Sally stepped forward again, and Mike heard a motor whir as the bars began to slide down, collapsing to about a foot above the mattress. She reached out her arms, and he waddled forward on his knees and fell into them. She hoisted him out and onto his feet, and he knew what was expected next.
“But I used to be a man, Mommy. What happened? When did I grow breasts?!”
“My goodness, did you get bonked on the head at the party last night? You’ve always been a hermie, mikey. It was only after you had to start wearing diapers again that you started embracing your sissy baby side. I thought it was adorable, so I went along with it. Don’t you remember us picking out this furniture for you, shopping for toys to fill your toybox and pretty little dresses and rompers for your closet?”
Strange images filled his head. He helped her paint all this stuff! They picked outfits at some Lolita store online! What was it called? Angelic something… He remembered filling the toybox with stuffed animals, and a dollhouse, and…
None of it made sense, but the memories were there, as clear as if they happened yesterday…
Or last night…
- End -