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Sarah and Jenn had previously met up with Jake due to a car accident, in where they apologized by bringing him home and thoroughly, well, fucking him. Later, they called him over again, and introduced him to their strap on, Jake enjoying the new experience, if not a bit surprised.
Every few weeks, the women would contact Jake and a similar story would play out. Occasionally they would meet up for drinks somewhere, or even a meal. But it eventually led back to their place, and schooling Jake in the finer points of pleasing a woman - well, two women - while also learning more about strap on play.
It was something that would come out sometimes, then more often, until it wasn't unusual for both women to emerge with smooth silicone bouncing from their crotch, or having them hidden under skirts to be a surprise reveal.
Sarah texted one late September day, as either were wont to do..
"Hey Jake! Been a couple weeks, but been busy, you know! Jenn and I have a Halloween party we are going to, though, and thought it would be fun for the three of us to do together! Come by Sat morn? We can get ready together, and it's that night. Say yes?"
Jake smiled as he read the text at work, feeling himself grow against his jeans just from seeing Sarah's name pop up in his phone. There wasn't much that he would turn down an invitation from these two women who had started to take over his social - and sexual - calendar.
"Of course! What is the costume? Should I pick one up? "
"Nope! ;)" came the reply. "We have it all set and will be so much fun!"
Jake shook his head, smiling. He'd be sure to be the focus of attention at any party with those two girls on his arms, he thought.
Saturday morning, he showered, thought about masturbating, but thought it would be best to be horny and ready for the ladies. He was supposed to be there by 9 am, and the party wasn't until later, so they must have a full day of fun planned ahead of time, he figured.
Arriving, he knocked as usual and Jenn let him in the door. God, she was beautiful. About 5'2", Jenn was an intoxicating mix of Eastern and Western features, olive skin, with dark hair streaked with purple. Still in pj's, her nearly C cup breasts bouncing freely behind the fabric as she waved her arms for him to come in.
Sarah walked from the kitchen, drinking a coffee. 5'11", she was taller than Jake in heels, though right now she was still barefoot also in pj's, though more revealing. Silk top with thin straps didn't conceal the hard nipples on her B sized breasts. Strawberry blonde hair draped over her shoulder, and her long tan legs extended out of very short silk bottoms that very much showed off the curves of her butt cheeks.
"Ok!" Sarah began, "first things first - shower time!"
"I just took a shower.." Jake, dumbly replied.
"No, no, no.. that won't do at all," Sarah replied. "Come on, we have to get you properly cleaned up!" She had a glint in her eye as she looked over to Jenn, who was smirking.
Jake shrugged and let the women lead him to the bathroom, where there was a large shower - big enough for them all, plus a seat.
Jenn, looking seductively over her shoulder, slowly let her bottoms slide over her ample backside, and then drop to the floor, as Sarah lifted off her top. Both looked at him with a look that said "Well?"
Taking the hint, Jake started shedding clothes as the water turned on to a nice temperature. Both ladies smiled at each other as they took in Jake's hard cock already at full mast.
"Somebody missed us.." Jenn drawled.
"Yes, quite! Some shower attention might be just the thing I need.." Jake replied.
Positioning in the shower, Jake went to kiss Sarah, who deftly sidestepped him. Then he went for Jenn, who instead grabbed him by his hardon and said "Now now.. prep first!"
Groaning, Jake acquiesced but not without trying to cop a feel or two, to giggles from the girls.
At their request over the past months, he had been shaving his privates, and then his ass. So he didnt think much of it when they said it was time for a cleanup, grabbing a bottle of foam.
Thry lathered his whole body, though, and he was enjoying the attention, not registering the tingling on his skin as anything odd. He was further distracted by Jenn, on her knees, face close to his bobbing head, as she wrapped one hand around him.
He couldnt hold back a moan, but Sarah next to his ear said "patience, lover" as Jenn began to slowly shave his crotch area with a safety razor.
Sarah lifted his arm, though, and moved in a razor towards his armpit, and Jake questioned her. Before he could protest, Jenn wrapped her lips around the head of his cock and sucked, making him shift into a groan.
"Just let us get you ready properly baby.." Sarah whispered in his ear, "Ok?"
Jake looked down into Jenn's eyes looking up at him, and nodded, dumbly. The razors and foam kept spreading over his body. Any time he went to protest, his bobbing hardon found its way into a hand or mouth, halting any resistance. Additional protests were met with a slim finger sliding between his cheeks and teasing his rosebud, which the girls had trained to love being penetrated. He was leaking by the end of the shower, and the girls had managed to remove every trace of hair beneath his eyebrows.
Jake felt that any touch on his cock would surely make him cum, as the ladies let him out of the shower, dried him, and began rubbing a strawberry scented lotion all over. On his now hairless skin, it was almost transcendent, making him shudder with new pleasure.
"That was amazing," Jake said, ignoring the very girly lotion's scent, and trying to get a hold of one girl or the other, unsuccessfully. "But you've got me crazy worked up.. and I am sure you both could use some attention.."
"Baby," Jenn said, finishing massaging lotion into his thigh, "I promise to take care of you.. but first we want to prepare for the party.."
"Please?" Jake wasnt beyond begging right now, drips of precum clearly making a mess on the tiled floor. "I promise to put myself in your hands, but oh, god, look at the state I am in!"
Sarah and Jenn shared a look, and Sarah spoke up, grabbing something black off the counter.
"How about a nice handjob from Jenn.. BUT, while she does, we use a new toy.." She held up what Jake knew to be a medium sized butt plug.
Not being a stranger to them toying eith his ass, though never using a butt plug, Jake, in his horny state was game "Yes, sure, yes, please..."
"Hands on the counter," Sarah commented, and he did so, sticking his butt out, and then felt Jenn's hand wrap around him.
She slowly stroked down, and at the same time, felt Sarah slide the lubed plug up and down between his cheeks. The next stroke down, he felt the tip pressing against his hole, and groaned in pleasure at both sensations.
The next stroke, the plug began to enter him, and on the upstroke, Sarah slid the plug back out. In, out, down, up, it went, until Jake was moving his hips and the girls hardly moved.
"Oh god.. I'm gonna cum.." Jake moaned and Sarah pushed the plug home, Jake pushing back against it, and Jenn releasing his cock. Jake groaned at losing Jenn's stroking, but he was too far gone and the plug hitting home pushed him over. Hips bucking, his cock swelled and spurted, Jenn catching his seed in her hand before sucking it into her mouth.
Pulsing still running through him, his ass clenching around the plug, Jenn stood and kissed him deeply, cum still in her mouth. Still horny from the ruined orgasm slowly running through his body, he just kissed her back, letting her push his cum in his mouth and swallowing.
Slowly falling to his knees, Jake tried to catch his breath.. ".. not fair.. not fair, fuck.."
Both girls giggled. "Oh, please.. you loved it," Sarah replied.. "and we have to build up to the really good stuff, anyway!"
Both women hugged him, lifting him back to his feet, naked bodies warming his skin, tingling, and he felt his half hard cock pulse again.
"Now, you promised to do whatever we said.. so time to start getting ready.." Jenn said.
Now, he wasnt sure he promised that, but his mind was a bit foggy. "Ok, ok, whatever you ladies want" he agreed.
"Yay!" they both cheered
" Ok, you can take care of us while we tell you all about our costume idea!" Jenn continued, dragging him into the bed room and pushing him back on the bed.
"So," Jenn began, as she climbed onto the bed and began to straddle Jake's face, "we decided to be sexy and risky.."
Jake' vision was taken up with the swollen shaved lips of Jenn, already slightly parted and wet. He was skilled at this part, having had the girls ride his mouth multiple times, and eagerly licked his tongue through her lips, tasting her sweet tanginess.
Jenn's hands in his hair, Sarah started to explain...
"So, we thought it would be fun to all go as sexy princesses..."
Jake couldn't respond, as Jenn ground down on him right at that moment and was suddenly cumming.
He thought, though, that the women would look awesome as princesses. So he would be the prince in their sandwich? That sounded like fun. And Jenn cumming definitely was partly related to Sarah' reveal.. so Jenn must be super hot about the idea.
As Jenn came down from her orgasm, Jake lightly licked her clean, her mewing above him. As she lifted up, he began to say "That sounds so hot and amazing.. count me in! I look forward to.."
Sarah cut him off, though, pushing him back down as she straddled him next. She had a blue garter belt on, with blue thigh highs attached as she pushed her wet pussy into his chin..
"So glad you agree!" she squealed, her legs pinning his arms down. Sarah had a slightly different taste than Jenn, but also intoxicating. And the nylons against his newly smooth skin tingled pleasurably as she started to slide back and forth over his lips and tongue.
He felt who must be Jenn slide something around his waist, mostly distracted by Sarah. Then Jenn was at his feet, and rolling something soft up his legs. God they felt so sensitive now, after shaving.. they must be those leggings princes wear, he thought.
Both legs now, up to his knees, and then Jenn started pulling whatever it was higher, while at the same time tracing her fingers lightly, and very eroticly feeling, up and down over the tights.
"Fuck yes," Sarah exclaimed, distracting him, as Jake somewhere registered straps down his thighs and ass being fastened to the.. not princes tight. But Sarah hand in his hair, and her suddenly cumming took his focus as she slowly rode out her orgasm.
Jake began to recover and move, to be stopped by Sarah slowly rolling her hips, indicating her going for a second, and Jenn's mouth sliding down over his leaking cock at the same time.
Teased for so long, Jenn didnt have too much work to do, even with Jake's mind half focused on trying to please Sarah again and sometimes gasping for breath, her occasionally sliding her ass over her tongue and pressing down, moaning loudly as his tongue pressed into her rosebud, which tasted slightly of vanilla.
Jake moaned into Sarah's ass as he exploded down Jenn's throat, as she sucked and sucked him, toying with the plug, and pretty much emptying him.
As he fell soft from her mouth, he felt her doing something, but Sarah started cresting above him, stealing his focus as she squirting a little, forcing him to swallow quickly.
Sarah slowly removed herself from him, but quickly pulled him into a kiss, keeping him slightly off base. Breaking the kiss, she looked deep into his eyes.
"We are so happy you're on board with the costumes.. just thinking about it made us both so fucking horny, it took all our willpower not to just forget it all and spend the day fucking. But dressing up and going out is going to make later tonight and tomorrow the best sexy time ever!"
Sarah's eyes sparkled, as did Jenn's when he looked down towards her, melting him a little.
But he was brought up short when he looked down his body to see a deep dustry pink garter belt around his waist, attached to matching thigh highs. His brow furrowed in further confusion at something pink he couldnt quite see between his thighs.
"Oh my god, we are going to be the three sexiest princesses at the party for sure" Jenn gushed at Jake. " I am soooo excited!"
Dumbfounded, and recovering slowly, information started to drip into Jake's brain.
"Uh.. ladies.. umm.. I'm not so sure about this..." he began.
They both looked at him, faces crestfallen, making him feel like a total heel.
"But.. but you agreed before.."
"You were all into it.."
"Just wanted to get his rocks off.."
"Be nice, we were horny too.."
"But he promised!"
"Right? God I could have cum again thinking of it.."
"What changed since this morning?"
"Yeah.. we got everything.."
"thought you'd love the surprise.."
"doing it for you, too.."
The women's exasperated comments shot out towards him, over each other, mixing, a garbled litany of disappointment and recrimination.
Jake, barely up onto his elbows tried to wave his hands for a pause.
"Wait, wait wait..." Jake started.. and the girls slowly stopped to look at him, their disappointment clear on their faces. Jake tried to remember back. He remembered agreeing to something, but wasnt clear. They did only mention princesses, so he obviously misunderstood. He could try to explain, but they both looked very sad. "I obviously misunderstood.." he began, as Jenn simply collapsed, depressed, on the bed with a huff.
"But.." he restarted, and Jenn's head shot up, looking at him hopefully.
Jake was trying to work things out in his head while he spoke..
"I know you both put a lot of thought and time into this... it is Halloween... I never really was a costume person.. it could be funny, and you both obviously think it is sexy, I dont know if it's weird for me because, well, *princess*... or just I never did costumes..."
he paused, huffed, shrugged and fell back on the bed.
Both women were a flurry of talk...
"so, that means yes, you will? that is so amazing and awesome and you're going to love it.. please? yes? tell us it is a yes.. oh my god, you'll be amazing, we are going to kill it.. Sarah did so much research.. Jenn paid atten to all the details.. ok, fine, team effort.. really it will be so amazing.."
"Ok, ok, ok.." Jake put his hands up. The girls quieted. "Yes, you win" which got a huge yay, and hugging.
"But let's not surprise me like this again?"
" You are all in? Will dress and do what we say?" Jenn asked, tentatively..
"Fine.."
"Seriously.. everything, no protests from now on?" Sarah asked more forcibly...
"Yes, ok..." Jake conceded.
The girls clapped and got up, pulling Jake to a sitting position. Which made him notice the weight between his legs felt off. Looking down, he saw his balls, but only a little pink nub. "Uhhhh.." he began, pointing..
"Oh! That is Jenn's" Sarah started. "If you are going as a princess, you have to be a princess! Plus you can't be swinging around a hardon under the skirts we have."
"It is called a chastity cage" Jenn continued... "and I spent a good chunk on it, making sure it is one of the most comfortable ones that are made. We were worried about a bulge showing, so got the enclosed smaller one, which is why I measured you a couple times in the past, and you can pee in it and everything!" Jenn was beaming at her choice and work she put into picking it.
Jake tentatively touched it, poking, prodding. The ring went around his balls and cock, and seemed snug, but not uncomfortable. The "cage" was more like a pink dome that reminded him of Sarah's larger clit with retracted hood. He couldnt feel anything through it.
"Ok, let me get my garters on too, and then we can dress together the rest of the way!" Jenn continued to talk, sounding super excited.
Jake continued to poke around the cage, as Jenn pulled on her purple garters, which matched the streaks in her hair. Then both girls sat next to him on the bed and handed him a piece of pink lace.
"Panties.." Sarah explained, pulling her own blue lace thong up her legs. Jake mirrored Jenn, one leg in, and then pulling them up while standing. Both ladies adjusted his thong, full and lacy, with think bands, even the thong part.
With the cage, it looked like he had full puffy lips under the panties. The thong cradled and slightly pressed the plug. They must have taken all his sizes, as it fit perfectly.
Three waist cinchers came out, and after Sarah and Jenn both seemed to easily get theirs on, they set upon Jake. That process was altogether a different case. Sarah pulled on laces, while Jenn held him, pulling the opposite direction. He gasped in surprise, which was probably a mistake as Sarah pulled and cinched it tighter. Short of breath, they instructed him to breathe from his upper lungs, not stomach.
*smack* Sarah hit his ass. "I always thought you had a sexy bubble butt, but damn, girl.. with you having a waist, your hips and ass just pop!"
Rubbing his butt, he offered a pained thanks. The cincher had a little lace skirt edging, and looking down his body, at least waist down, he was taken aback that it, indeed look like the bottom half of a woman. Even more surprising is the tightening in his crotch he felt as his cock apparently was trying to get hard. Was he turning himself on?
"So, tops are next buuuuut.." Sarah began.. "since you don't have anything naturally, I had to figure it out. " Holding up two breast forms, "so I went between me and Jenn.. figured we would all be close that way!"
Jake was about to protest, but held his tongue, remembering his promise and also figuring they were right.. he couldnt go flat chested.
"Ok, lay back, and we'll get these on.." Sarah started, then seeing Jake open his mouth the question, added "yes, so they go on with an adhesive, and we have the removal stuff. But this way, I can blend everything to your skin tone and it will all look natural."
Jake let himself be woman-handled, lay back and let Sarah put the forms on. The middle was slightly indented and he felt his nipples get slightly pulled up, a bit like those vacuum tubes they had used on him before. After a few minutes, Sarah started on blending the edges with different tools Jake couldn't recognize. After 20 minutes, Jake looked down, and was hard pressed not to think his head was now on a woman's body.
Jenn flicked his new boob's nipple and he swore he felt the flick against his own. At his look, she said "Yeah.. we went high end. Theres a little electrode that connects them so you can actually have near real feeling! Awesome, right?"
Taken aback a little, Jake could only mumble a yes in reply. Things were snowballing and he wasnt in control anymore he realized. He felt his trapped cock pulse somewhere below his stomach.
The skirts were hardly that. Yes, the other women wore the same outfit in a different color, but a breeze would show their panties for sure. Or a robust walk. Pushup bras and a tight top, all matching the dusty pink color, There were opera gloves, but those were for later. Next was the makeover.
To Jake's credit, he did begin to protest when they started in on his eyebrows. But he was quickly consoled that it would all be easy to reshape and not be obvious until they grew back in a bit more. Hair was styled, promises made that the minimal cutting wouldnt show, and then extensions were woven in with varying shades of pink.
Makeup, and nails took at least another 2 hours. Thigh highs came off to paint toe nails a matching pink, before they were replaced and heels came out.
Earrings were clip ons. Matching jewelry - necklace, rings, bracelets, an anklet were all added before Jake was allowed to see a mirror. Based on what Sarah and Jenn looked like, though, they were artists.
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