This story is the second chapter two my earlier story "A High School Bet" which can be found in "First Time". Although this story works ok as a stand alone story it may help to have read my other story first.
Jesse Sinclair felt slightly awkward and worried. He'd made a bet and lost and now he had to face the forfeit dreamt up by his kinky twin sister Jessie. Both seniors in high school it was now a couple of months until the eighteen year old twins were to graduate. In the hope of livening up these final couple of months Jesse had made a bet with his twin sister that he would be the first to take the virginity of innocent girly classmate Lizzie Nichols. The fact that in front of him sat Lizzie, with her arm around Jessie's slender waist, was testament to Jesse's failure.
They had agreed that the winner of the bet could make the other do whatever they wanted as a forfeit. In his arrogance Jesse had assumed that this would enable him to have his wicked way with his twin sister. Now, however, the tables were turned and he had sat there nervously as Jessie and Lizzie had left the room to discuss his fate. Now he tried to calm himself, after all what's the worst that could happen? he thought as he saw a wicked grin grow on his sister's face.
"We want you," said Jessie, her beautiful blue eyes turning briefly to Lizzie to make her complicit in all this, "to have oral sex with one of the most popular kids in senior year."
That doesn't seem bad at all, thought Jesse with relief, frankly he'd expected more from his kinky sister than this feeble forfeit. But Jessie wasn't finished yet.
"And we get to pick who the person is. Do you agree? Although of course you have to, it's your forfeit."
"OK, fine," said Jesse still with relief.
"OK then," Jessie looked over again at Lizzie and grinned showing her perfect white teeth, the shorter girl grinned back, "We choose Brock Stewart."
Lizzie giggled briefly as Jesse's face fell, mortified. Captain of the football team, Brock was the ultimate jock, popular, muscular and fiercely insistent on his straight sexuality. Brock and Jessie had dated briefly before they mysteriously broke up and Jesse wondered briefly if this wasn't just Jessie's way at getting back at him but also at Brock. Strangely Jesse's first thought wasn't disgust at the idea but a feeling that it wasn't possible.
"You'll never get Brock to agree to fuck a guy," he said.
Jessie let out another perfect grin, "That's ok, we'll just have to get him a girl then won't we?" she winked at Lizzie who giggled again as Jesse's face fell in further shock.
Jessie was an honourable person and when he made a bet he had to carry through with it, whatever happens, this is what he told himself as he stood in the shower, totally naked before his gorgeous sister and her girlfriend. Once he was showered Jessie eagerly rubbed hair removal cream all over his body and then let him shower it off, taking with it all of his body hair to leave his long legs as smooth as his sexy sister's. Lizzie and Jessie let him dry off, saying that they'd meet him in the next room.
Walking into the next room, Jessie's bedroom, Jesse saw laid out on the bed a black lace corset and panties, stockings and a garter belt and a low cut red party dress. Standing behind him Jessie tightly laced him into the sexy black corset, forcing his waist to become narrower to create a feminine hour glass figure. Jessie couldn't help but feel a little aroused as Lizzie slid his now smooth legs into the black lace lingerie panties and enclasped his semi-erect cock in them. Jessie then helped him fasten the garter belt as Lizzie pulled up his black silk stockings. The feel of the silk against his smooth legs sent an electric thrill running through his body as he tried, he felt succesfully, to hide his growing arousal from the two attractive girls running their hands over his increasingly feminine body. Into the C cup of Jesse's corset his sister slipped a couple of convincing silicon breasts and topped it off by slipping his sexy red dress over his head. As the dress fell around him Jesse felt more sexy than he had in a long time.
Next Jessie sat her twin brother at her make-up table and began to apply slutty red lipstick and rouge to Jesse's soft feminine features. Jesse was shocked to see his face transformed before him until he looked the spitting image of his sexy sister. Walking over to the full length mirror he was greated by the sight of a gorgeous girl in a sexy red dress and black silk stockings. The feel of the lace and silk against his hairless skin and the sight of blonde bombshell in the mirror was too much for Jesse and he could no longer hide his growing hard-on.
Jessie noticed this and put one arm around her brother's shoulder and began to run her hand over his crotch. "I think she likes it," she said smiling at Lizzie, "Don't you Julie?"
Jesse could only nod, supremely embarassed by the whole situation, but knowing that worse was yet to come. His parents were away for two weeks and Jesse and Jessie had the house to themselves.
"For those two weeks," Jessie told him firmly "You will live as Julie, you will learn to dress, speak and act like a woman until you can fully charm and seduce Brock. Once the stupid jock has cum in your mouth then you're free from your forfeit and can go back to doing whatever you want.
Two weeks later and Jesse and Jessie's parents were to return two days later. That day at school Jessie had forced his brother to go and get Brock to date their "cousin" Julie. Jesse had no idea what his sister would do if he failed but he didn't want to think about it.
In the showers after basketball practice, both Brock and Jesse were on the team, Jesse decided to talk to him. He couldn't help but notice the muscular jock's eight inch cock as they showered alongside each other. He began to think about how he would take the large beast in his mouth and was horrified to find his own cock becoming erect. He had to turn and quickly grab a towel to wrap it around his waist as he and Brock got out of the showers.
"I have found the perfect girl for you man," Jesse was saying.
"Why should I let you set me up?"
"Wait till you see the picture I've got of her, she's my cousin," Jesse said, taking from his bag a polaroid that Jessie had taken of him in a dark curly wig with bright red lipstick and heavy, slutty make-up. Jesse found the photo deeply sexy and arousing and was sure Brock would too.
Brock paused, obviously attracted by the girl in the picture, "She's not like your bitch sister is she? She certainly looks like her."
Jesse drew Brock into a conspiratorial huddle around the photo, "I've heard she likes to give head on the first date."
Brock grinned, "You're on."
"Great, she'll meet you at the diner at seven tomorrow."
Brock turned to get dressed and Jesse breathed a sigh of relief, both at achieving his mission and at the fact that Brock hadn't noticed his hairless body or his continued arousal at their close proximity.
That evening Jesse returned from school and went upstairs to dress as Julie. He found Jessie already there on the bed, as he walked in she and Lizzie were liplocked in a passionate embrace. For the last two weeks Jesse had barely seen Jessie and Lizzie apart from each other. Outside they maintained the image of being best friends but at home Jesse always caught them making out. As far as he knew they hadn't got any further than the oral pleasuring Jessie had given her little girlfriend to win the bet.
Jessie looked up from the kiss as he walked in and removed her hand from stroking Lizzie's smooth thigh beneath Lizzie's short skirt. Lizzie gave Jesse a look of faint annoyance and disappointment at his breaking them up. Jessie however smiled eagerly at him,
"Good, you're home," she said as Jesse stripped off his male clothes and Jessie began to lace him into a pink corset with white lace and Lizzie put his cock into pink silk panties, "You've got one more important girly lesson."
Jesse slipped into a pink summer dress with a short skirt and low-cut white lace bodice before putting on his curly black wig and applying some slutty make-up. Finally admiring himself in his sexy girly form in the mirror.
"You can walk, talk and act like a girl," Jessie continued, "But now we're gonna teach you to suck cock like one."
With that she brought out an eight inch strap-on dildo to which Lizzie gave a look of surprise almost as great as Jesse's. Jessie turned to Lizzie and said:
"Can you strip off honey? I need your help with this."
Lizzie stripped out of her clothes to reveal her sexy little body, pert breasts and enticing pussy. Jessie helped Lizzie get into the strap-on before getting to her knees in front of her girlfriend's impressive prosthetic cock.
"Now Julie, I'm gonna show you, then you can copy."
Jessie began to jerk off the prosthetic member whilst she bent over to kiss it, licking her tongue around the end of the rubber cock before gradually taking it, inch by inch, in between her full red lips and bobbing up and down. Jesse was getting quite turned on just watching this and he looked up to notice a smile of pleasure on Lizzie's sweet girly face.
However at this moment Jessie pulled away and thrust Jesse in front of Lizzie's rubber beast. First he just blankly stared, a little disconcerted, but then slowly, and a little inexpertly, he began to copy what his sister had just done. At first it felt weird but as he continued to bob up and down he began to enjoy the feeling of the firm, hard dildo in his mouth and he felt his cock, rock hard and erect, straining against his silk panties, already wet with pre-cum.
Jessie noticed this and pulled him away from his cock sucking.
"That's really great Julie, I knew you'd love it once you got started. Just one thing," she pointed to the huge bulge in his dress which betrayed his erect cock, "We can't be having this showing."
So Jessie decided that she would use an elastic strap to strap Jesse's member to his leg so he wouldn't disturb the smooth shape of his skirt on his big date.
Sure enough the next evening, having once again removed all his body hair to give him perfectly smooth skin, Jesse strapped his cock down with elastic whilst his sister laced him into a gorgeously sexy black corset with red lace and slipped in the fake silicon breasts. He slipped his ass into a matching pair of black and red lace panties and Jessie helped attach his garter. Once again a thrill of pleasure ran through his body as he slid the black silk stockings up his now smooth sexy legs.
Over this Jesse put on a little red leather dress with a skirt so short that the tops of his black silk stockings were easily visible if he bent over or sat down. To top this sexy outfit off he wore black leather stiletto boots and black leather elbow high gloves with his curly black wig and dark make-up and lipstick. Admiring himself in the mirror Jesse was pleased and attracted by the vision before him, in fact he felt his cock straining heavily against its elastic strap.
Suddenly, and painfully, the elastic snapped and Jesse's erect member sprang free, creating an unsightly bulge in the front of his skirt. Lizzie clapped her hand to her mouth, insistently straight Brock would never go for a girl with a huge bulge in her dress and it was already 6:45.
Jessie walked over and Jesse thought she would call the whole thing off and spare him. Instead she shocked both him and Lizzie by dropping to her knees, lifting the skirt to his leather dress, unclipping his stockings, pulling down his lace panties and putting her lips around his cock, rapidly Jessie sucked her twin brother off to a climax until his cock exploded in her mouth.
Making sure to swallow every drop of Jesse's cum so as not to stain his sexy outfit. Finally, having sucked him dry, Jessie let her brother's now limp cock slip from her mouth and pulled his panties back on, re-attached his stockings and stood up as Jesse re-adjusted his skirt. For ages he'd lusted after his sexy sister and now, without warning, he'd been able to cum in her mouth.
"Thank you Jessie," he said sincerly.
"We've got no time for that Julie," Jessie replied, "You've got a date to go to. Go on, make me proud."
With this she slapped Jesse playfully on his leather clad ass and sent him out, dressed as a woman, into the world for the first time. For a moment Jesse enjoyed the look of jealousy and annoyance on Lizzie's face before stepping out onto his big date.
Jesse Sinclair's cousin Julie was ten minutes late, but that didn't matter at all to Brock when he saw her. Looking even sexier than in her photo Julie walked over with a sexy sway of her hips. She was dressed in a sexy red leather dress which showed off her stocking tops and kinky leather boots and gloves. They both ordered burgers and sat in a secluded booth to eat them. Brock couldn't take his eyes off Julie's curvy body, long legs and deep blue eyes the same as Jessie's. He was completely absorbed in Julie and could barely pay attention to what she was saying in her deep sensual voice, so absorbed he was in staring at her.
Embarrasingly he felt his cock grow hard as she placed her leather gloved hand on his knee and began to feel up his thigh. Stopping where there was now an obvious bulge in his pants she caressed his crotch. Julie leaned in towards him and Brock expected her dark lips to plant a kiss on his, instead she whispered in his ear in her throaty sexy voice:
"Why don't we go somewhere a little more private."
Brock could only nod and follow as Julie led him by the hand from the diner and back to the house where she was staying with Jessie and Jesse. Brock knew their parents were away and thought about what Jesse had told him about his cousin giving head on first dates, he smiled at the thought as Julie led him up to a bedroom.
Instantly inside the room Julie instantly grabbed Brock in a passionate embrace, locking their lips together she caressed his tongue with hers as Brock could feel his increased erection straining against his pants. Seeming to feel or realise this too Julie dropped to her knees and unzipped Brock's pants allowing his hard, erect cock to spring free.
Slowly at first Julie began to jerk him off with her gloved hand, Brock enjoyed the sensual feel of the leather glove against his skin as Julie began to kiss and lick the head of his firm cock before gradually taking it into her mouth and beginning to bob up and down on it whilst her leather gloved hands played with his balls and ass.
A man's man, Brock usually liked to be in control with a woman however he was totally in awe of Julie and her cock sucking and just let her get on with it as she eagerly and ever more quickly bobbed on his erect beast. Brock could feel himself nearing a climax as Julie reached to brush her black curls from her eyes . . .
. . . And brushed them right off her head, to reveal blonde hair beneath! But this wasn't half as shocking as what Brock saw when he looked down, noticing the impressive bulge in the front of "Julie's" skirt he suddenly realised she wasn't Jesse's cousin at all but Jesse himself. However he was now so far gone he couldn't stop himself and he felt his cock explode inside "her" mouth, covering "her" face and dress with his creamy juices. Brock felt shocked and embarrased by the whole situation and even more devastated when he heard a victorious feminine laugh.
He turned to see Jessie emerging from the wardrobe laughing, with her best friend Lizzie. Jessie was brandishing a video camera.
"Won't everyone at school be pleased to see the kind of girls you go for Brock," she laughed wielding the video camera.
Brock went red with shame, looking away from "Julie's" body, covered in his cum, the fact that he still found her sexy of even greater embarrasment to him.
"But, we can make your little secret disappear and give you the tape," Jessie continued, as Brock audibly breathed a sigh of relief, "All you have to do is take our Julie here as a date to the prom."
"What?!?" said Brock and Jesse simultaneously.
Brock thought for a moment. His reputation at school would be ruined if this tape got out, however nobody would suspect anything if he went to the prom with sexy Julie. Besides, even though he struggled to admit it to himself he was still kind of turned on by her, even knowing her secret, "I'll do it," he said.
Jesse thought for a moment. He'd fulfilled the terms of the bet and was free now. But if that tape got out then he'd be even more humiliated. Also he was beginning to enjoy the sensual pleasures that being a woman was giving him and felt perhaps he'd like to explore this further, "I'll do it," he said.
"Great," said Jessie, "Brock, you'll pick Julie up from here at seven thirty."
Later that evening and Brock had left, Jesse had gone to bed, exhausted after his big night. Jessie and Lizzie sat alone on Jessie's bed in silence. Lizzie was struggling to strike up the nerve to ask Jessie a very important question. She knew that Jessie still cared a lot about her popularity and reputation and that everyone else thought they were just best friends. Still Lizzie managed to steel herself up to ask the question:
"Jessie, would you be my prom date?"
For a while Jessie just sat in silence, Lizzie could see her beautiful blue eyes glazed over, deep in thought. Jessie stayed like this, thinking things over, for some time before finally her eyes lit up as if she'd made a decision. She turned to Lizzie and her beautiful mouth spread in a perfect smile that made Lizzie's heart jump before she'd even said anything.
"I can't think of anyone I'd rather go with or be seen with," she said smiling and, taking Lizzie in her arms, kissed her full on the lips, as Lizzie's mind slipped to her dreams of their future together . . .
To be concluded in the final chapter "Jessie and Lizzie's Prom".