Twice Foiled Thrice Lustful

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Twice Foiled, Thrice Lustful

By Paul Calhoun

It's Halloween season, so I thought I'd bring back one of my most popular casts, though not in the way requested. Filip/Rachelle and Rob meeting is a romantic story, and Halloween is the season for tricky stories! So we have Delmore and Lerman once again trying to prank a friend with a girl disguise.

With the score so heavily weighted against Delmore, one can only wonder what the third installment will do to him...

“I don’t know what happened last time, but we’re sure to get Alfie with this!” Lerman said, hopping up and down as he tugged the rounded buttocks over his own behind. His cock bent backwards between his legs as the false vagina pressed up against it, settling his male organ into place beneath the labia and mound containing a fake passage.

“Yeah!” Delmore replied, pulling on the two sides of the body suit as his friend struggled to fit his thick, mannish arms into the slim ones of the suit. While Lerman was flexing his fingers to get them the last half inch into the manicured digits, Delmore forced the halves together and pulled the zipper up. He was careful not to exert himself too much, though, since he was wearing his best clothes in anticipation of going on a date as soon as he dropped Lerman off.

Lerman wrapped his new female hands around the attached breasts. “It’s too bad Katy has such small tits.” He lamented, squeezing, lifting and then letting go before making a few sudden motions to watch them move. “I’d love to play with a nice big rack when we’re done, but the prank’s the important thing.” He picked up the mask and examined again Katy’s button nose, high cheekbones, small pouting lips and almond eyes peeking out from behind her pixie cut bangs. Unable to wait another moment, Lerman slid it over the bald cap he was wearing and down until his face was lost in hers. Delmore helped to smooth it out and hide the seam while Lerman as Katy admired herself in the mirror they’d set up in Lerman’s room. After twirling, bending and making every facial expression he could think of — noting that Delmore was getting hard watching him make flirty moues at himself - Lerman turned to Delmore and said, “Do you have the clothes?”

The voice changer in the mask worked as expected and Delmore automatically replied, “Sure Katy.”

Lerman didn’t comment, but his own penis turned hard at the thought of how easy — and fun — this was going to be. “Great,” she said, making a show of putting on the panties in front of Delmore, easing them up her legs and patting her crotch to underscore how it showed off the smoothness of her pubic region. “And you’re sure that she isn’t going to be around?” Katy asked as she put on the bra.

“She’s going to be out all day.” Delmore replied, his eyes roaming over the body of his friend transformed into Alfie’s hot girlfriend as she put on a blue knee-length skirt, a tight navy top with a scoop neck and then sat down to put on open-toed sandals. He was sorry they hadn’t started sooner; he would have loved to have an hour or two with ‘Katie.’

Lerman intentionally spread his legs as he raised his feet to put on the shoes, watching in satisfaction as Delmore fought not to react to the view up her skirt. “Awesome!” Katy chirped. “I called Alfie earlier with the voice box on to tell him I wanted a nice quiet evening in and I set up the cameras yesterday.” She stood up and Lerman showed off how much he’d practiced in heels by walking with a deliberate hip swing past Delmore, then twirling on one heel around and leaning forward until her nose was almost touching his. The moment Delmore broke and looked down her top, she kissed him on the tip of the nose and turned back to the door. “Come any time you want.”

In the car, Lerman couldn’t help playing with his new body, rubbing her smooth legs together and absently lifting and squishing her boobs together. “I think the bra and shirt make them look bigger somehow. Rounder.” She twisted in her seat and lifted them again, mashing them against each other. “What do you think?”

“Uh, maybe,” Delmore replied, desperately trying to keep his eyes on the road.

“You know what else? This butt looks good and it’s really comfy.” She shifted her weight onto each buttock in turn, then bounced in her seat a couple of times. “I just hope they don’t burst when I’m getting hot with my boyfriend!”

Delmore gulped and concentrated very hard on the road. Lerman decided it was safer to clam up and contented himself with admiring how pretty he was in the passenger mirror as well as winking and blowing kisses to people they passed, especially other young ladies. Watching their reactions, Katie thought that later she could cruise a few lesbian hangouts and get lucky pretty fast. When they arrived, Lerman took a deep breath — something both he and Delmore paused to look at — and exited the car with a ladylike swing of the legs. “Thanks for the ride!” She called to Delmore, just in case Alfie was watching. Her broad smile told everyone that she was about to go spend the evening and night with the man she loved.

The moment Alfie opened the door, Katy put her arms around him and kissed him deeply. “I missed you, hon,” she said.

“It’s only been a day!” He laughed, scooping her up and carrying her inside, kicking the door shut.”

Katy hung her legs over his arm and snuggled into his chest. “It feels like longer.”

Alfie bent his neck and Katy scooched up his body to share another long kiss. Alfie didn’t break the embrace as he set Katy down and sat next to her. Katy was inching over to drape her skirt over his legs so she could sit on his lap when a familiar voice broke in. “When you’re done seeing how far you can stick your tongue down my boyfriend’s throat, we can get on with this.”

Alfie’s sister Janet was standing, hands on hips, an expression of mixed annoyance and amusement on her fair, delicate features. She tossed her head, her back-length spill of black hair shining in the sunlight from the window and bouncing in the tight ponytail she habitually wore. Her slim figure seemed a little fuller that day and her voice was definitely not the high soprano it usually was.

“Aw, Katy,” Lerman said. “Just when I was starting to really get into this.”

“You’ll have someone else’s to borrow soon enough,” the false Janet said in Katy’s voice. “Not that you aren’t doing exactly what I would do if I wasn’t — you know — his sister right now.”

“So let me do you a favor and love him for you,” the fake Katy said, smiling invitingly to Alfie as she made no move to disentangle herself from him.

“We’re on a schedule,” Janet said, tapping her foot.

“Oh, all right,” Katy said. “I guess it wouldn’t look right for you to start in on him until all the ‘guests’ have left.”

“That’s right,” Maria said, entering behind Janet. She was curvier than both the other two combined and Lerman’s hidden erection began to harden again at the thought of what was coming.

Katy got up and quickly mouthed, ‘girl talk’ to the camera Lerman had placed earlier. He’d left Janet’s room devoid of surveillance and Delmore had agreed that he didn’t want to anger Janet and that it wasn’t likely any of the ‘prank’ was going to happen there anyway. He’d also set it up so that the microphones would be ‘buggy’ for the first few minutes, so that their conversation wouldn’t be heard. All Delmore had seen so far was the fake Katy come in, make out with Alfie and then have to go have a quick chat with Janet and his own girlfriend Maria before they left. He’d arranged to meet Maria outside Alfie’s house, so they’d have to ‘talk’ fast.

In fact, Janet was already pulling her mask off as she entered her room, Katy shaking out her short hair and dropping the mask on Janet’s bed. None of the women looked at each other askance as they stripped out of their clothes, even though one of them was a man underneath and would be again soon. Katy and Maria were all business as Katy put on the clothes her doppelganger had been wearing before and Maria put on the Janet mask and clothes. The fake Katy retreated to the bathroom to remove the bodysuit and mask. Lerman saw that the voluptuous suit and the mask with its light freckles and straight red hair was already waiting. He debated whether to concentrate or just masturbate until the erection he’d gotten from the act so far and the sight of who he was going to be next went away. It was a moot point since the decision distracted him enough for the hard-on to fade and he hurried to squeeze into the Maria suit before it came back.

Lerman loved the curves that he was taking on and wished he could spend more time getting used to them. Instead, he hurried along with changing into Maria, pausing only long enough to make sure the mask was a snug fit and blended well into the rest of the body. The real Maria — now fully dressed as Janet - ran her finger along his spine to check that there wasn’t a visible zipper and gave the tab a few extra pulls before hiding it under a self-sealing flap of skin. She laughed softly at the relief evident on her double’s face as she hooked the bra together and adjusted the straps so that her chest was well supported. Lerman knew boobs were heavy, but not how much of a difference underwear made. There wasn’t much point in additional cleavage or volume with Maria’s body. The fitted shirt and tight slacks showed off her hourglass figure and generous proportions well. Once clothed, the new Maria looked with solicitous concern at the real one disguised as the sister of the man she’d just pretended to be the girlfriend of. “How far is it OK for me to go?” She asked, worry evident in her adopted voice. “I love your body and I wouldn’t mind giving Delmore my all, but I don’t want to take this too far.”

Janet kissed Maria chastely on the cheek. “That’s sweet of you, but don’t worry. Delmore’s been spending all his time preparing for this little joke of his and I’m not really feeling very charitable towards him. Do whatever you like with him.”

Maria grinned. “Thanks, girlfriend!”

Janet laughed and gave her replacement a half-serious high five. “We’d better go.” She said. “Delmore’s going to start wondering what we’re doing in here.”

“You mean something like this?” Katy pulled Maria towards her and Lerman was subjected to the same style of kiss that he’d given to Alfie a few minutes earlier. “Just getting you primed,” she said coquettishly.

“Do you think Delmore’s going to notice that Alfie’s sister is a little — umm — bigger than before?” The new fake Janet asked as they walked out.

“Nah,” Katy said. “He’ll have his eyes glued on me and Maria.”

“You more than me,” the new Maria said, practicing being annoyed with Delmore. “I bet he’s going to spend our whole date checking the cameras on his phone.

“Well, he won’t want to miss the surprise,” Katy said, giggling.

“He doesn’t have to worry,” Maria said, a slightly sadistic smile on her face, “he won’t.”

Maria and Janet picked up their purses on the way out, waving to Katy as she closed the door. Janet peeled off across the lawn — the real Maria didn’t want to get too close to her boyfriend in the mask in case he recognized her body — leaving Lerman as Maria approaching the car. Lerman was worried that his ‘girly’ trained motions might resemble his Katy persona too much, but after a few steps he decided he didn’t have much to worry about. Maria’s body was so different that everything about her gait was changed by it. Things that looked cute on Katy looked like an invitation when done by Maria and she didn’t have to work hard at all to swing her wider hips. Stopping next to the car, she popped a hip and tapped her shoe on the pavement. Delmore got the idea and opened the door for her. Maria smiled easily as she slid in next to her boyfriend, kissing him hello before they drove off.

“Did you have fun with Katy?” Maria asked, trying to sound both interested and ironic. Lerman didn’t actually know if Delmore had told Maria or if she’d found out.

“Aw, don’t be jealous, babe!” Delmore said. “I was just giving her a ride. Besides, you know it wasn’t really Katy anyway.”

That answered that question. “Yeah, I bet it was even better.” Maria said, pouting. “Getting to see her naked on your friend there while you terrorize another. You’re so immature.”

“What’s wrong?” Delmore said. “It’s not like I’m ignoring you or anything. We’re going out, aren’t we?”

“Yes we are.” Maria patted Delmore on the knee. “Just don’t get too wrapped up in that little joke of yours while we’re out. I want you all to myself and not watching your genderqueer mate snogging poor Alfie while you film it.”

“He’s not queer!” Delmore said while Lerman tried not to laugh at how he was getting Delmore to defend him. “It’s just a prank, sheesh.”

Lerman thought he might be laying it on thick, but he reconsidered. Maria and Delmore seemed to be constantly bickering. Lerman guessed it somehow helped their relationship. So he kept up his snarky comments about himself and Delmore kept defending him to who he thought was Maria. They pulled up to Maria’s place and she waited for Delmore to open the door for her. “Thanks, hon.”

Lerman had to fish around in Maria’s purse a little to find her keys and when she went in, Delmore immediately sat down and turned on the TV. “I’m not going to take that long.” She huffed.

“Yeah, I bet.” Delmore replied.

Lerman found that Maria had laid out an outfit for their date on the bed and left a note on top of it. The fake Maria shimmied out of her pants as she read it.

‘Hope you’re seducing my boyfriend and he isn’t suspecting anything. Just a head’s up that he has a power fetish and so a lot of my outfits are made with trick seams. Just so you aren’t surprised when he literally tears your clothes off as a form of foreplay. I rarely get to have my own back, though, so when it’s time for his ‘surprise’ don’t hesitate to be as rough as you like with him. Have fun!

<3 Maria’

Lerman smiled with Maria’s face at the sentiments on the note. “All right, girlfriend,” she said softly. “I’ll give him everything you want me to.”

The outfit she’d left was a classic little black dress with a straight, knee-length skirt, sheer hose and pumps. She’d pinned a pair of clip-on earrings that looked like regular piercings as well as directions on how she usually applied evening makeup. At the bottom of the pile was a stylish purse which the fake Maria transferred all the things from the day purse into. She checked herself out, unable to resist taking a few pictures of herself turned so that both her bust and booty were on display, uploading them on Maria’s phone with the tag ‘guess who has a date tonight!’ In fact, the sight of herself made Lerman look with longing at the drawer he knew she had a few of her toys in. Much as he’d love to settle in with a vibrator between her legs, her eyes slit shut in ecstasy as she massaged her drop-dead sexy body, he knew where it would go. Long before he’d had enough, she’d open her eyes to find Delmore with his hands on her boobs, squeezing as he got on top of her. Since Lerman’s pair had no feeling, he wouldn’t notice and Delmore would assume that Maria was intentionally letting him have a feel and take that as an invitation. They’d never get out in time, miss their reservation and his comeuppance would be ruined. Giving herself one last practice look of lust, Maria opened the door and went back into the hall.

Lerman had never practiced with a skirt like the one Maria had given him and her copy and her first steps out of her bedroom were hesitant. When it came time to join her boyfriend, she pulled her shoulders back and strutted towards him, deciding that if she played sexy, he wouldn’t notice any minor clumsiness. If his erection hadn’t been at full strength from the modeling session, the look she got from Delmore would have done it. She allowed a slow, lingering kiss before taking his hand and pulling him towards the door. “We’ve got reservations, remember!”

Lerman loved that she now had someone who looked at her that way, opened doors and bought her dinner while still thinking himself the lucky one. As they ate, Lerman pretended to know all the things Delmore talked about, buoyed with every successful lie just as much as by the high quality wine her boyfriend had ordered for them. Her fun at Delmore’s expense and the sensual delight her body gave her with every movement - and even sitting still - wasn’t enough to get Delmore off the hook, though. The relationship he was pretending to be a part of would be nothing without a few jabs, and the fake Maria jumped on Delmore every time he even tried to glance down at the feed where Alfie and Katy had progressed much faster through their evening and were already going up to bed when dessert arrived.

Not that Delmore was completely fixated on his prank. He spent at least twice as much time with his hand roaming over her leg, occasionally creeping up under her skirt to her upper thigh. Lerman thought they both deserved a little sexual pleasure from this, so he allowed Delmore’s hand to go even further as the meal progressed. Delmore looked surprised and ecstatic that Maria was letting him be so bold in public, and he froze when he felt a delicate, long-nailed hand on his crotch. After all, Lerman thought at Delmore massaged his fake pussy beneath the sexy underwear, Maria should give as good as she was getting.

When Maria went to the bathroom — an adventure in itself as Lerman learned on the fly how the suits worked on the toilet and how a woman cleaned herself — she returned to find Delmore hunched over the screen, Katy and Alfie evidently engaged in some spirited bedroom activities. “That’s it, turn it off!” Maria said. Delmore started guiltily and Lerman almost gave himself away by laughing at his misfortune. Maria’s expression barely twitched and to cover herself, she held out her hand. “Now give it to me. You’re not allowed to have it back for the rest of the evening.” Delmore reluctantly parted with his means of seeing the ‘prank’ unfold and Maria dropped it into her purse. Bending over so that her seated boyfriend could see all the way down her cleavage to her panties, she smiled slowly. “Now, if you’re so desperate for a bit of fun, let’s go back to your place. I’m sure I can be better than some silly joke.” Neither of them saw the stares Maria was getting, her butt revealed through the clingy fabric of the skirt as she bent over. They were too busy looking at each other, though for completely different reasons.

Lerman was floating on air as Maria watched how her proposition had instilled a reckless haste in her boyfriend’s behavior. Before she knew it, Delmore had paid the bill and for the second time that day — but the first in that body — Lerman found himself swept off his feet into the hands of a strong, horny man. Delmore’s self-preservation kicked in long enough for him to set her gently in her seat before he tore off in the car towards home. Unbeknownst to him, there was a single camera in his bedroom that would record what was coming to him. Given what was on offer, he might not have minded.

There was no pretense at civility as Delmore picked Maria up again and took her into his house. No flirtation over coffee, no slow, sensual progress towards an evening’s climax. Instead, Maria was carried directly to the bedroom and Delmore jumped with her under him onto the bed. As predicted, her clothes were very swiftly removed in the most direct way possible, almost damaging the panties which had been made to look good, not be torn clean off. The garments were thrown into a corner, leaving Maria nude with Delmore straddling her. He removed his trousers first and Lerman was momentarily jealous at how Delmore had reacted to Maria before deciding that it was fine because for the time being he was Maria and he’d be having fun with that later. Wiggling out from under him, Maria took Delmore in her mouth and made sure he stayed ready as the rest of his apparel joined hers. Delmore’s eyes were wide with undisguised awe and rapture at this and Lerman guessed that it was rare for Maria to ‘debase’ herself by giving a blow job.

The remainder of their sex was fast, energetic and a little dizzying. Maria didn’t have to work at anything since she’d excited Delmore so much that he pumped her furiously , bringing Lerman and himself to orgasm with a technique that shook the bed and made Maria’s eyes cross. The real one hadn’t been understating Delmore’s love of manliness at all! Maria lay in a very feminine post-coital cloud, replete in her allure and the product of it. For awhile Delmore was content to cuddle with her, but when she pretended to fall asleep, he stealthily went to her computer and connected to the cameras again, catching Katy and Alfie in their own pre-sleep embrace. There weren’t any chairs nearby, so he had to bend over to use the mouse. Katy seemed to be getting another wind and Alfie was stirring when Maria opened one eye to see her boyfriend watching again. Now he definitely deserved what was coming. Soundlessly, Maria reached between her legs and fiddled inside her vagina until Lerman’s penis was free. It was dripping, but still hard, ready for action. Again, with as little noise as she could make — though it looked like Delmore was completely entranced by what he thought was Lerman in Katy in bed with Alfie — she spread some lube over the shaft sticking out of her, biting her lip against voicing how much she wanted to use it. Creeping up behind him, she massaged his waist and said in her sweetest little-girl voice, “honey?”

“Yeah, babe?” Delmore said, neither turning nor straightening up.

Katy and Alfie sat up, their arms around each other and waved to the camera. Delmore stiffened, but it was too late. “Surprise!” Tightening her grip and pulling him in at the same time as thrusting her hips with all her strength, falling backwards to add gravity to the mix. Lerman’s dick penetrated Delmore, the lube letting him go all the way to the base.

“Maybe third time will be the charm.” Lerman teased, still with Maria’s voice as the real one walked in, carrying the Janet mask. “He’s all yours,” she said to Maria. “I think I’ve softened him up nicely for you.”

Maria high fived her naked double, sauntering in and taking a crop from under the bed. “I’ll be the judge of that.” She said in a playfully menacing tone. She placed a box smelling of leather on the sheets. “I think we’ve only begun.”

“Is that an invitation?” The fake Maria asked, Lerman’s cock sticking straight out at the thought.

“Sure.” Maria said, tightening a strip of leather over Delmore’s wrists before he could recover enough to fight her.

A slow smirk spread over the fake Maria’s features. She picked up the Janet mask, sliding it slowly over Delmore’s head. “I think I have a few hours to spare. Maybe when we’re done I can put this away,” she tweaked her cock. “Then go and get that Katy suit back. I’m sure we can find someone who’d love to have three ladies like us for the night.”

“You — you,” the manly Janet sputtered.

The Marias both took turns cutting off his protests with their mouths. The fake one grinned as the real one went to work in earnest. “Third time’s a charm?” She suggested.

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