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Jessie and Lizzie’s Prom

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Booty Shake

This story is the third and final part of my story that began with “A High School Bet” (in “First Time” section) and continued with “Jesse’s Forfeit” (in “Transsexuals and Crossdressers” section). Although it may exist as a standalone story it may help to have read those stories first to understand what has happened up to this point.


The prom was the event of the senior year at River Falls High School where eighteen year old twins Jessie and Jesse Sinclair and Jessie’s best friend Lizzie Nichols went shopping for prom dresses. Nobody at school knew it yet, but because of the strange events of the past few weeks Jessie would be taking Lizzie as her prom date, whilst Jesse was going as his female alter-ego Julie with Brock, captain of the football team. It was for these two faintly odd dates that the three of them picked out prom dresses the week before the big event.

A week later and “Julie” waited anxiously for her date to arrive, biting her perfectly manicured red finger nails with nerves at the thought that Brock might, knowing her secret, pull out of the date all together. She was dressed in a long powder blue dress with complex spaghetti straps. Beneath this a tight lace corset stuffed with fake silicone breasts turned Jesse’s masculine body into Julie’s hourglass figure, her cock was strapped down and hidden beneath her panties, stockings and garter belt. With Jessie’s help she had worn her black curly wig up in a fancy, attractive style and had applied rather more understated make-up. Looking in the mirror Julie flattered herself that she was a deeply attractive woman and Brock would have to be mad to turn her down.

Still despite this Julie still sat there anxiously waiting for her date to show up. Seeing this Jessie knocked her gently over the head:

“What are you so nervy about Julie?” she said, “You know what’ll happen to him if he doesn’t show,” she waved a video at him. It was the one on which they had recorded an obviously endowed Julie sucking Brock’s cock. They were now using it as a safeguard to make sure Brock showed up on his date.

At that moment the door bell rang and in came Brock himself. Dressed in an immaculate white tuxedo Brock cut quite a charmingly attractive figure and Julie was very proud to be turning up on the arm of such a gorgeous gentleman. Brock handed her a fancy blue corsage, and, taking her by the arm, escorted her out to a white stretch limo. Brock had really gone all out to make an entrance and Julie really appreciated this.

As Brock and Julie drove off in their limo Jessie went up stairs to finish getting herself ready and helping her date Lizzie.

Lizzie sat in front of the mirror, wrapped in just a small white towel her smooth legs dangled seductively from her stool. Her shoulder length dark hair was in curlers and she was applying some mascara as Jessie walked in. Looking up Lizzie was delighted by the sexy appearance of her friend and date. Jessie was dressed in a strapless pink silk dress which pushed up and enhanced her already massive breasts. She was also wearing elbow high pink silk gloves and high pink pumps. A silver necklace pointed down to her impressive cleavage and Lizzie felt a desire to bury her face in it, the sight of her sexy friend was making her quite worryingly wet. Jessie’s already long blonde hair had been given hair extensions so it fell sexily all over her shoulders and her blue eyes sparkled with pleasure.

Lizzie’s own eyes lit up with love, she couldn’t think of anyone she’d rather share this special evening with than her gorgeous best friend. Thus far the only sex that the two girls had managed involved Jessie eating her friend out. Lizzie knew Jessie wanted more and she felt tonight she might finally be ready for it.

“You look gorgeous,” Lizzie said to her friend.

“I know,” Jessie said, giggling and giving Lizzie a little model-type pose, “Now it’s time to get you ready for our big entrance.”


Jake Leeds watched as a huge white limo pulled up outside the school, out stepped Brock Stewart, captain of the football team, dressed in a show offy white tux. Brock walked around to the other door and opened it, holding out a hand to help his date get out of the car. Emerging from the limo was one of the most gorgeous girls Jake had ever seen. A tall leggy girl with gorgeously extravagant black curls in a sexy powder blue dress.

Jake walked over to introduce himself, feeling himself a little abashed and tongue tied in the presence of such a beauty, finally he held out his hand and managed to speak:

“Hi I’m Jake,”

“Hi,” she replied in a deep, sensual voice, giving him her hand daintily.

At that moment Brock stepped in:

“This is Julie, Jessie Sinclair’s cousin,” he said.

That would explain why she looked a bit familiar.

“Ah,” said Jake, a beaming smile on his face, “So your the blow-job girl.”

Julie blushed a crimson colour that made her look even sexier. Brock gave Jake a quick frown as he took Julie by the arm and escorted her in.

Upon casino şirketleri entering into the dance hall Brock, in his bright white tux, and his gorgeous date certainly turned many heads as they began to slow dance close together. Julie felt safe and happy in Brock’s strong arms as she pressed her fake breasts against his chest. She could already feel his semi-erect cock pressing against her thighs, at the same time she could feel her cock straining against its restraint. As she leant her head on his shoulder she whispered seductively in his ear:

“If we go somewhere more private I can help you sort that out.”

Jake watched Brock and Julie quickly leave the dance floor and go out the door, he guessed what they were doing and walked over to a couple of other friends on the football team to talk to them.


Meanwhile whilst all the attention had been on Brock and his sexy date another limo pulled up outside and out stepped Jessie Sinclair, gorgeous popular blonde and favourite for prom queen. Her entrance slightly usurped by her sexy cousin, now all eyes turned to Jessie as she stepped out the car in her pink dress. Everyone had to admit she looked gorgeous and they all strained to see her date, about which there was a lot of mystery.

Jessie walked around to the other door and opened it. There was a hushed moment of anticipation before out of the car stepped Jessie’s best friend Lizzie Nichols. Lizzie looked great dressed in a black halterneck dress that showed off her cleavage with her whole small body looking sexy and enticing, if anyone was going to challenge Jessie for prom-queen it would be Lizzie. The crowd waited for the sexy girl’s dates to step out of the car but nobody did. Jessie and Lizzie linked arms and walked into the dance hall whilst everyone looked on a little confused.

For a moment Lizzie stood on her own and she was approached by Steve Cooper, a jerk who thought all women wanted him.

“Flying solo tonight Lizzie?” He leered, not attempting to hide the fact that he was staring right down her dress, “Well, we can take care of that.”

Steve reached out to her and Lizzie was for a moment struck dumb. She’d come with such confidence as Jessie’s date but now she couldn’t bring herself to say it and just backed away from Steve’s outstretched arm. Steve was about to say something more when Jessie reached in and grabbed his arm.

“Back off jerk, she’s with me,”

“All the better,” Steve grinned uglily, “You two gorgeous girls shouldn’t be dateless on prom night.”

“We’re not dateless,” said Jessie, loud enough for everyone to hear, “Lizzie is my date, and I couldn’t think of a better one.”

There was a hushed shocked silence around the hall as Jessie took Lizzie’s hand and they walked into the centre of the dance floor to slow dance together. The rest of the room barely moved, staring open mouthed at the couple. As she danced in Jessie’s arms, her body pressed against Jessie’s curves, Lizzie felt happier than ever before. She looked up with admiration into Jessie’s blue eyes and, in full view of the whole school, pulled Jessie’s face towards her and planted a kiss on her full red lips.

As the two girls locked in a lengthy, sexy kiss the whole hall stood in stunned silence. A couple of guys drooled with lust but mostly they looked on disapprovingly. However Lizzie was oblivious to it all, she didn’t care who knew how much she loved and cared about Jessie, and here, wrapped in her lover’s arms she felt nothing could harm her.


Julie and Brock found themselves now in a deserted dimly lit corridor of the school, nobody would come here, they were all too busy at the prom, staring at Jessie and Lizzie. Brock pushed Julie against the wall and started to kiss her, his hands on her pert girly ass, Julie could feel her own hard cock straining against its strapping, she was really turned on as Brock pushed her to her knees and unzipped his pants allowing his own hard erect cock to spring forth.

Julie needed no further invitation as she began to go down on the well hung football star, taking the length of his cock in her mouth and sucking him off. Soon Brock felt his knees buckle and huge streams of cum burst from his dick, filling Julie’s gaping awaiting mouth as she swallowed it all, desperate not to stain her sexy blue dress.

Brock was about to put his pants back on when they heard a voice:

“I thought I’d find you two here,” it was Jake accompanied by a couple of other members of the football team. “Now’s the time to see if Julie’s really the cock sucker you said she was.”

Julie was taken back at this suggestion that she would like to suck Jake’s cock. She still clung on to vestiges of her straight identity as Jesse and the thought of doing this to another man than Brock made her slightly sickened. She looked up at Brock who had reddened with embarrasment.

“Come on Brock, you know that’s how it is on the team,” Jake was saying, unzipping his pants, “Remember how I let you screw Kelly and Sarah, casino firmaları well now it’s my turn.”

Brock turned pleadingly to Julie, “Please, Julie, just do this for me this once.”

Julie saw she was stuck, there was nothing she could do so she resigned herself to the situation, secretly a little curious about what cocks other than Brock’s would be like. As Jake dropped his pants Julie couldn’t help but laugh at the size of the little four inch fully erect cock that emerged.

“Suck it bitch,” said Jake slapping Julie across the face with his little dick.

“Don’t speak to my date that way,” Brock was saying as Jake backed down a little.

Julie easily took Jake’s little dick right inside her mouth and began to suck him off, clearly from the moans and groans of pleasure Jake was enjoying this and Julie felt her hard cock telling her she was too although she didn’t enjoy the emptiness given by the fact that Jake’s cock was much smaller than Brock’s.

Julie could see the other two guys had dropped their pants and were beginning to jerk themselves off. Instinctively Julie reached up her extravagantly manicured hands and began to jerk off the other two cocks whilst continuing to suck on Jake’s.

Very quickly Jake came to a climax and blew his load into Julie’s mouth, it didn’t taste nearly as great as Brock’s cum but Julie still savoured it and swallowed making sure none of it stained her beautiful dress. She let Jake’s little, further shrunken, cock slide from her mouth and took the heads of the other two in instead as she jerked them off to a climax, the two guys almost simultaneously cumming into her eagerly waiting mouth as she struggled to swallow two loads at once.

Finally she had finished with all three of them and they efficiently put their pants back on and walked off back to the main hall whilst Julie stood up with Brock’s help and straightened out her blue dress.


Lizzie held Jessie in the kiss for what seemed like forever, savouring every moment of her perfect happiness before finally having to come up for air. She stared lovingly into her friend’s eyes for ages, Jessie’s blue eyes sparkled back with love and happiness reflected from Lizzie’s own.

Their moment together was broken when they were pulled apart by Kelly Simmons:

“Don’t you think that’s a bit much,” Kelly said obnoxiously, “I mean, what are you trying to say here. Lesbianisms a bit last season isn’t it?”

Lizzie could feel the anger boiling up within her as she desperately just wanted to reach out and slap Kelly. Jessie, noticing Lizzie’s anger, held out a hand to stop her and spoke calmly to Kelly:

“I’m not saying anything, this is who I want to be at the prom with, this is who I care about and I wouldn’t have it any other way.”

Then, with Kelly looking a little put out, Jessie slapped her, hard, so she flew back a few steps. Everyone stared for a moment before Kelly made a quick exit and everyone laughed. Lizzie looked up into Jessie’s eyes, it was those sparkling, laughing eyes that she’d fell for first and smiled:

“Thankyou,” she mouthed as Jessie leant over for another kiss.


Brock and Julie were walking back to the hall when Julie stopped for a moment outside the girls’ toilets:

“I’ll just go freshen up a bit and I’ll meet you back in there,” she said, her make-up and lipstick smudged by her cocksucking.

As Julie re-applied and touched up her make-up whilst admiring herself in the mirror she realised her cock was still hard and straining against its restraint, not wanting a repeat of her first date with Brock in which its elastic restraint had snapped Julie decided to sort this out.

Walking over to one of the stalls she locked the door and sat down on the seat of the toilet and pulled up her dress revealing her panties and stockings beneath, she quickly unclipped her stockings and dropped her panties to the floor. Unstrapping her cock it sprang free, hard and erect, and she began to jerk it off. It didn’t take long for her experienced hands to bring herself to a climax, spewing her milky white juices into her hands.

She began to lick her hands clean of her tasty juices, savouring the pleasure of it, when she heard someone come in. Two other girls stood in front of the mirrors touching up their make-up. From the sound of their voices Julie recognised Jessie’s good friends Lucy and Sarah.

“What is Jessie doing?” Sarah was saying, “Does she realise how this is going to affect her reputation?”

“I don’t think she cares,” was Lucy’s reply.

“God, nobody’s going to look at her in the same way, she’s lost it, she’s not even going to make prom queen after a faux pas like that.”

“Maybe she really does want to be here with Lizzie,”

“Either way it’s disgusting, I don’t know what she thinks she’s doing, it’s an insult to all of us as her friends.”

“If you were really her friend you wouldn’t care who she’s with. I think it’s great that she feels able to express herself like this, good for güvenilir casino Lizzie,”

“I never liked Lizzie that much,” Sarah concluded and strode off, slamming the door.

Meanwhile Julie had continued licking her hands clean of her cum, had strapped her now limp cock back down, put her panties and stockings back and stood up to straighten her dress again. She emerged from the stall just after Sarah had left. Lucy turned, surprised to see someone else here.

“Julie, hi,” she said, “I didn’t know there was anyone else in here.”

Julie smiled at her, “I’d like to thank you for sticking up for Jessie, you’re a real friend.”

Lucy smiled back as Julie walked over, “You’ve got a little stain on your chin there,” she said pointing.

Looking in the mirror Julie saw a couple of drips of her cum still on her face and quickly wiped them off, Lucy smiled knowingly at her and walked out of the room as Julie followed.

On arrival back in the hall Brock turned to her:

“What took you so long? They’re about to announce prom queen.”


“I don’t really mind that I didn’t win queen,” Lizzie said to Jessie.

“Neither do I, I’ve won something far more important,” she looked at her friend and smiled and Lizzie felt a warm glow of happiness.

“Besides,” Lizzie went on, “Didn’t Julie look great winning, she deserved it.”

“Yeah she and Brock make a lovely couple.”

They were standing beside the dance floor towards the end of the evening, watching Brock in his immaculate white tux dance close to Julie in her sexy blue dress, the newly crowned prom king and queen. Jessie was surprised to find herself genuinely happy for them, the old, manipulative, competitive Jessie wouldn’t have been at all happy. Lizzie had changed her for the better.

Lizzie felt that Jessie had changed her too, now there was only one thing she could think about, she leaned over to Jessie and whispered in her ear:

“I think we should probably make an exit while the night is still young, we’ve plenty more to do tonight. Tonight I want to go all the way.”

Brock saw Jessie and Lizzie leave the hall arm in arm and pointed it out to Julie. Julie leant over and kissed him on the lips:

“We should probably follow soon, there’s plenty more fun we can get up to this evening.”

She gave him a sexy seductive wink and sure enough, after that dance, they too left arm in arm.


Back at Brock’s empty house Brock threw Julie back onto the bed, passionately kissing all over her face and neck whilst stripping from his white tux until he was completely naked, his erect cock protruding enticingly from his body. Quickly Julie stood up and allowed her blue dress to fall to the floor so she stood before him dressed just in a white lace corset, panties and stockings. She looked totally gorgeous as she dropped to her knees again and gave Brock a passionate, wet blowjob. Just as Brock felt himself racing towards a climax however Julie stopped and let his cock fall from her mouth. Brock was put out for a moment.

“It’s prom night, don’t you want something more?” she said in her deep sensual voice, “Don’t you want to get inside my panties tonight?”

Brock’s eager look and erect member said more than he could in words as Julie unclipped her stockings and pulled off her panties, letting her own hard erect cock spring free.

“First you’ve got to get my pussy nice and wet and lubricated, eat me out.”

So Brock found himself on his knees licking around Julie’s tight round anus. Brock had never done anything like this before and just concentrated on the thought that he was licking a girl’s pussy and not a guy’s ass.

Julie moaned in pleasure as Brock’s tongue darted in and out of her anus:

“Oh god yeah, that’s it, come on, eat my pussy.”

Soon enough Julie got Brock onto his feet again:

“OK, that’s enough, now are you ready to pop my cherry?”

Brock threw her back onto the bed and pushed her legs wide apart. Julie pulled her cock and balls up to give access to her ass and Brock violently and eagerly ploughed in. The pain was far more than Julie had anticipated and she screamed out. However soon she realised these weren’t screams of pain but of intense pleasure as the hunky football star thrust in and out, robbing her of her anal virginity.

At first Brock began to play with Julie’s silicone tits through her lace corset but as he continued to thrust in and out he found himself, to his surprise, to begin jerking off Julie’s cock in time with his thrusting. Finally he could hold himself in no longer and he felt his cock explode in Julie’s ass with one final powerful thrust, filling her hole with his warm, sticky juices. This stimulation in her ass and Brock’s hands on her dick was all Julie needed to send her over the edge as well as she felt her body shake as her orgasm spread from her ass through her body until her cock too exploded. It was the greatest orgasm she’d ever had and she blew bucketloads of cum all over Brock’s chest and her own corset for what seemed like ages.


Lizzie and Jessie left the prom arm in arm, more people continued to stare at them but Lizzie was by now totally oblivious to it all as she stared into her friend’s shining blue eyes:

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