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A Literotica Halloween Story Contest 2024 Official story. All characters are over 18. Feedback welcome, as always.
The house seemed far too big for just one person. Sometimes Sara thought it was too big even for two, especially since Kevin had started sleeping in a separate bedroom, and now that he was overseas, she felt as though she was rattling around in this huge old house like a pea in a whistle.
She didn’t blame Kevin for choosing to sleep apart. He was a hugely successful lawyer specializing in defamation cases, but his job was frequently stressful and his insomnia almost legendary. About a month ago, he said he’d found a therapist who was helping him calm down and sleep at nights — at least, on nights when he didn’t have to be up at ridiculous hours for a zoom meeting with someone in another time zone — and Sara had started to hope they might start sharing a bed more often. Not that their sex life had been particularly exciting even before he was made a junior partner, but it had been comforting. She was his second wife, a former fashion model, and knew she was regarded by his colleagues as a trophy in much the same way as the penthouse and the Maserati. She owned her own small business, but she felt like a figurehead there, too, with the office manager doing their job so effectively she doubted anyone would notice if she stopped turning up at all.
Sara got out of bed and wandered into Kevin’s bedroom. He’d mentioned that his therapist had given him a headset that played some sort of ASMR that helped him relax and sleep, and she wondered whether he’d taken it with him. It wasn’t on his nightstand or in any of the drawers, so she walked into his closet, and did a double-take when she saw a pair of hot pink stiletto heels amid his shoes. She picked these up and stared at them, realizing that they were too large for her — not that she would have willingly worn anything in that shade, even in her early days as a model — but they looked just big enough to fit Kevin. She searched quickly through the clothes on the shelves, and found a pleated pink miniskirt, a pink wig, a headband with cat ears and a matching tail, a pink choker with SLUT in brass letters, black stockings printed with the same word, a suspender belt, a flesh-coloured vest with deflated breasts, and a lacy bra that could easily have accommodated two pumpkins.
Though amazed, she carefully put every disturbing item back exactly where she’d found it, and tried to rationalize the discovery. She could tell that the clothes were relatively new, not something from Kevin’s law school days. It was only five days before Halloween, and the law firm occasionally held parties exclusively for the employees, no spouses invited, so she tried to convince herself that Kevin had bought the costume for a Halloween party, either for himself or for a more recent recruit — male or female – who the senior partners wanted to humiliate.
She wondered for a moment whether to mention the find to Kevin when he called, and decided against it: as he wasn’t expected to return in time for Halloween, it seemed possible that the costume would never be worn and might be discarded without them needing to discuss it. If not, she could confront him after he returned.
She stepped out of the closet, and noticed an object under the bed. She blinked, knelt, and picked it up. It was a headset, with an on-off switch and a knob. Curious, she switched it on and listened. She had to strain her ears to hear any sound at all, and turning the knob didn’t seem to make much difference to the volume, so she slipped the headset on. She could hear a very faint rhythm, rather like a heartbeat, and what might have been a voice murmuring softly, but she couldn’t make out any words. It did cancel out other noises and silences in the house, which was somehow soothing after the shock of finding women’s clothes in Kevin’s closet, so she left it on as she headed for bed.
*
Luna had dressed as Elvira, Mistress of the Dark, for her eight o’clock paypig, and (unlike the Vampirella and Morticia costumes which were also frequently requested on Halloween), it was comfortable enough that she left it on while she waited for her eleven o’clock, who’d also expressed a desire to be dominated by Elvira. Like Cassandra Peterson, Luna was actually a natural redhead (though only her best-paying clients ever had the privilege of seeing her heart-shaped rose-red pubes), but she had a large collection of wigs, and the waist-length black hair was reserved for her personal use, not for her crossdressing clients.
Halloween was always a busy day for her; as well as her regulars, she had extra bookings from occasional clients who used the day as an excuse to crossdress in public in sexy Halloween costumes, and subs who wanted a last chance to make cummies before they locked their sissy clitties in chastity cages for No Nut November. Kevin had texted on the 25th to say that he wouldn’t be able to keep his usual appointment, but would pay for her time anyway, so Luna and her apprentice, Xin, were startled when the bell rang. Luna walked over to the monitor and did a double-take when she saw the figure standing at the door. The heart-shaped face was unfamiliar, though the cotton candy pink wig, cat ears and choker looked like the ones she’d sold to Kevin. “Who’s there?” she asked cautiously.
“I’m your slutty bimbo slave, mistress,” came the reply. “Can I come in, please?”
“That one’s being doing her voice training exercises,” remarked Xin, who wore a sexy parody of a mad scientist costume: a translucent white lab coat, black thigh-high boots and long black gloves. “Sounds like a real woman.”
Looks like one, too, thought Luna. Either they weren’t wearing make-up, or it was done so expertly as to look completely natural. But what would a woman be doing here, now? She didn’t currently have any female clients. “Check the garage,” she told Xin.
Her apprentice walked over to the laptop and logged into the security camera. “Red Maserati,” she said. “Isn’t that what Penny drives?”
Luna nodded. Xin always referred to the clients by their female names, for fear of making a slip; Kevin’s was Penny, though they sometimes changed that to Peggy when they were using their strap-ons. But while the person standing outside the lift door might be wearing Penny’s sissy accessories, they didn’t fit them well, and Kevin/Penny stood 6’6″ tall in her pink stilettos; the person outside was at least four inches shorter.
Luna stared at the small screen, wondering what to do, for long enough that Xin turned around and asked, “Could Penny have given her slot to someone else?”
“Not if she knows what’s good for her,” Luna growled. “And I don’t appreciate Halloween pranks.” She un-muted the microphone and said, “Wait there. And no playing with your clitty.”
“Yes, mistress. I mean, no, mistress.”
“Good girl.” She muted the microphone and walked over to the laptop. “That’s Penny’s Maserati, alright. Give me a second.” She searched for news images of Kevin until she found some of him with his wife Sara. “Take a look at the face in the monitor and tell me if you think it could be the same person.”
Xin walked over to the screen, then returned. “It looks like her,” she agreed, “but why would Penny send her wife here?”
“I don’t know. This is weird even by my standards. Unless…” She walked back to the monitor, un-muted the mic and asked, “Have you been listening to the audio recordings like a good bimbo?”
Sara beamed. “Yes, mistress! Every night, like you told me too.”
“That’s my good bimbo slut. You can play with your clitty now, but don’t come.” She muted the mic, and turned to Xin. “Okay, that explains how she knew when to turn up and what to wear, but I don’t remember saying anything about this address.”
Xin shrugged. “Ask the Professor.”
“I will, tomorrow, but what the fuck are we supposed to do now?”
“Let her in?”
“What?”
“The Professor will want to know how effective the conditioning was, won’t she? The bimbofication is only supposed to last as long as it takes her to get here, go home, and go to bed; she’ll be back to normal once she wakes up, for the rest of the week. And she may be expecting the same treatment Penny gets.”
Luna looked at her suspiciously. Xin’s major was in theatre arts, but she was doing a minor in abnormal psychology to help her with method acting. “And what if she snaps out of it in the middle of a session?”
“I don’t think that will happen. And even if she does, I don’t think she’ll go public; it would be too embarrassing.”
“It’ll be even more embarrassing for Penny! And not good for us, either.”
“Penny’s a high-powered lawyer, right? That means pre-nup. His wife’d lose everything if they divorced.”
“People have risked more for revenge. A lot of women don’t like knowing their husbands enjoy being sissified.”
“But some do,” Xin replied. “It gives them a handle, and not just the obvious one. How many of our clients do you think get a spanking after they get home? Or have to clean up the house like sissy maids or 50s housewives? Or let themselves be cucked, or worship their wives’ feet or clits or assholes, or give them expensive presents as a way of saying they’re sorry?”
“Well…” Luna knew of many cases where this was true, including several where the women made the bookings for their husbands or bosses, one who made her husband describe what Luna had made him do then regaled him with stories of how her well-hung lover had fucked all of her holes, and a few who took their subby hubbies out on shopping sprees the day after their sessions to buy expensive clothes and jewelry for themselves while the men — sometimes in business suits and sometimes in drag – bought themselves girly lingerie, sissy fetishwear, perfume, cosmetics, sex toys and femdom porn.
“So we could just tell her to go home,” Xin continued, “but that might backfire, and I think it would be at least as safe to let her come in.” And much more interesting, she added silently. “But we should probably leave the cameras running, just so we have a record. The professor will want to see it, and it may be useful to have evidence that will back up our story.”
“I’m starting to wish I hadn’t let you talk me into this experiment.”
“How much more are the clients you gave the headsets to paying you now?”
Luna sighed. “I’ll let her in. But I hope to hell you’re right.”
*
Sara walked into the room and immediately dropped to her knees, then flipped up the back of her miniskirt and prostrated herself, revealing that her tail was attached to a butt plug buried in her asshole, just as Kevin had learned to do. “Thank you, mistress,” she said. “How may your slutty bimbo serve you?”
Luna closed the door and looked at Sara’s shoes: not the pink stilettos she’d ordered Kevin to buy, but what looked like genuine Louboutins. Most of the rest of her costume fitted her badly; Kevin was broad-shouldered and barrel-chested, while Sara was almost as skinny as in her fashion model days. “Let’s get those clothes off you first,” Luna replied, “and fix your makeup. You don’t look nearly slutty enough for my taste… yet.”
“I’m sorry, mistress.” Sara replied. She began unbuttoning the white blouse, revealing even more of her enormous inflated breasts in the lacy black bra. She unzipped the skirt and pulled it down to her ankles, then unhooked the bra.
“No,” said Luna as Sara started to unbuckle the choker that concealed the collar of the silicon vest. “Keep the collar and the boobs. Busty sluts are the best sluts.”
“Yes, mistress. Thank you, mistress.”
“Now the suspender belt, the stockings and the shoes. And the ears. You can keep the wig.”
“Yes, mistress.”
“Do you remember your name, slut, or are you too much of a bimbo?”
Sara looked confused for a moment, then smiled. “I’m a complete bimbo, mistress. The only time my head isn’t completely empty is when there are cocks in my mouth.”
That was another line Penny had learned to recite, and Luna nodded. “You’re slutty Suki,” she improvised. “Can you remember that?”
“I’ll try, mistress.”
“Good slut. Whenever Mistress Xin or I call you Suki, you will do exactly as we say. Do you understand that?”
“Yes, mistress.”
“Good. Now take the tail out and give it to Mistress Xin, then sit on that chair.”
Sara/Suki obeyed, wincing slightly as she pulled the butt plug out of her asshole. The plug wasn’t much thicker than a thumb at its widest, except for the flange that held the tail. Xin grabbed the tail at its midpoint, and carried it into the bathroom, returning a moment later pushing a trolley bearing Luna’s makeup kit. “I’m going to make you look as slutty as possible,” said Luna, grabbing a scarlet lipstick. “Like a porn star who’s just about to do the biggest gangbang scene in her career.”
“Thank you, mistress!”
“You love being a slutty bimbo, don’t you, Suki?”
“Yes, mistress! I love being your slutty bimbo slave!”
“Good. Mistress Xin is going to pump up those fake boobs of yours to maximum size while I do it, and I want you to imagine how many men would have to jerk off over you to cover those boobs with come.”
Suki blinked, then grinned.
“You like that idea, don’t you?”
“Yes, mistress!”
“Good. I don’t have any men here, but we’re going to have a lot of fun tonight anyway.”
It took nearly ten minutes before Luna was satisfied with the make-over and asked Xin to bring a mirror so that Suki could look at herself. She squealed as she saw her face; Luna had used make-up to give her lazy bedroom eyes, accentuate her cock-sucking lips, and generally make her look like a cheap sex toy whose purpose could not have been more obvious if she’d had ‘slut’ written on her forehead and ‘fuck me’ on her cheeks. Her nails had been painted Barbie-pink, but ‘bimbo’ was written in paler pink on the nails of one hand, and ‘slut’ on the other, followed what looked at first glance like a heart, but Suki stared at it for a moment and realized it was actually a woman’s ass. She giggled in delight at her mistress’s cleverness.
“Now everyone can see that you’re a slutty big-boobed bimbo slave,” Luna purred.
“Thank you, mistress!”
“I think we should take some photos. First, I want a big slutty smile to show everyone how happy you are being a slut.”
Xin walked over with a digital SLR and took several headshots before Luna was satisfied. “Now, I want you to try to turn those blowjob lips into a perfect circle, as if you were a cheap blow-up sex doll begging to be fucked in the face. Yes, that’s good. Now, how big was the biggest cock you’ve ever sucked?”
Suki blinked. She had vague memories of having sucked several cocks of different sizes and colours over the years, but she’d never measured any of them. “I don’t remember, mistress,” she said, and repeated, “The only time my head isn’t completely empty is when there are cocks in my mouth.”
“Of course. There shouldn’t be anything else in a fuckdoll’s head. But don’t worry, we’ll give you a cock to suck on soon.”
“Thank you, mistress!”
“But we’d better get you dressed first. Bimbos and fuckdolls aren’t smart enough to dress themselves properly. If they didn’t have mistresses to dress them, they’d just walk around naked all the time with their big boobs and their slutty fuckholes on display and accessible to anyone who wants to use them. And while that might be fun for a while, it would just get them into all sorts of trouble. Besides, there are ways to dress you that make you look even sluttier than just being naked.”
“Thank you, mistress!”
“What costume should I get?” asked Xin. “Slutty cheerleader? Slutty bride?”
“French maid.”
“Latex or lace?”
“Lace. Black. With slut stockings in her size, and pink pleasers. And a seven-inch dildo for her mouth. A black one.”
Xin nodded. She retreated into the enormous closet, and returned moments later with everything Luna had asked for. “Suck on this while I dress you, Suki. Xin’s going to take some more photos. Don’t worry, we’ll send you copies that you can look at while you play with yourself at home.”
Suki licked and sucked on the dildo while Luna dressed her like a doll in a black underbust corset that lifted her Z-cup boobs, with suspenders for her stockings. She added a frilly white French maid’s cap, a diaphanous black skirt even shorter than the one Suki had worn coming in, a lacy white apron that didn’t quite cover her cunt, and sparkly pink stripper heels. To complete the set, Xin brought her a feather duster, a bottle of anal lube, and the smallest inflatable vibrating butt plug in her collection.
Luna spread Suki’s cheeks and looked appraisingly at her asshole, which had closed up since she’d removed her butt plug. She applied a dollop of lube to the little rosette, and gently rubbed it around the hole, then rubbed more onto the rubber stopper on the end of the feather duster and began slowly inserting the duster into Suki’s ass.
Despite her mouth being full of fake cock, Suki gasped at the unexpected intrusion. She hadn’t had anal sex since long before she’d married, back when she was still trying to get listed with the more prestigious modelling agencies. She hadn’t enjoyed it then, and putting the butt plug in her asshole earlier that night was done purely out of a sense of duty instilled in her by the hypnotic recording. Now, part of her mind told her that this wasn’t right, this wasn’t who she was. Another part, slightly louder and more convincing, countered that maybe that wasn’t who she was this morning and maybe it wasn’t who she would be tomorrow, but it was who she was now and who she wanted to be — a bimbo slut who took it up the butt. The gasp became a giggle as Luna slowly and carefully slid the handle of the feather duster deeper and deeper into her bowels until all six inches were buried inside her and Xin took photographs.
“I’m going to ask you a question, so take the cock out of your mouth,” said Luna, “even though you don’t want to. What is a maid’s job?”
Suki tried to think. “To serve her mistress?”
“Yes, that’s good, but how does she serve her?”
“By doing whatever her mistress wants?”
“A maid’s job is cleaning,” said Luna. “Do you see that coffee table there? I want you to dust it.”
“Yes, mistress.” Suki reached around and grabbed the feather duster, then froze when Luna said sternly, “Did I tell you to take that out of your butt, slut?”
“No, mistress, but…”
“Leave it in there. You don’t need your hands to hold a duster. Now put that cock back in your mouth where it belongs, and go and dust that table.”
Suki walked over to the table, the duster still sticking out of her ass, and after a moment’s thought, twerked her way around the table, feeling the duster’s handle moving around distractingly in her ass. When she’d completed a lap of the table, Luna nodded and told her she could stop. “Lie face-down on the table.”
“Mmm, mmm-mm.”
Luna withdrew the duster from the table and tossed it to Xin, who caught it by the feathers. “Nice ass,” the dominatrix said, “but a slut like you should have a tramp stamp saying something like ‘Staff entrance’ or ‘Free admission’. I suppose we’ll have to improvise.” She grabbed a scarlet lipstick and wrote ‘ATM HERE!’ just above the top of her butt crack. “Now, I’m going to put a vibrator in your slutty little asshole to give you a gape that a porn princess would be proud to show off.” She grabbed the inflatable butt plug, slathered it with lube, and slowly pushed it into Suki’s ass until the widest part of the cone had slipped through her sphincter, making Suki gasp around the dildo in her mouth. Luna switched the vibrator on, on the slowest setting, and said, “This is a special toy for anal sluts like you. It doesn’t just vibrate, it gets bigger every time you come. You can play with your clitty if you like, and you have my permission to come.” She was intrigued to see how this would work on a woman: the subliminal instructions in the audio recording told the listener that they couldn’t orgasm without permission, but once that was given, the next time they heard Luna say ‘come’, they would — voluntarily or otherwise, depending on the level of humiliation or frustration Luna thought they wanted. Some of her clients would be edged for nearly an hour; others would be told to ejaculate almost instantly. She wondered how many orgasms she could give this bimbofied fuckdoll before moving onto the next step.
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