Lesbian sex stories > A High School Bet
By Jessica Erotica
Her First Lesbian Sex,
Lesbian
Orgies | Girl
for Girl | Lipstick
Lesbos
*** This story was originally posted in three parts on Literotica five years
ago. I have just discovered this site and I have therefore decided to resurrect
it for a new audience here. It contains lesbian sex and male to female
crossdressing. Do not read this story if you are offended or not turned on by
this. ***
Part One - A High School Bet
Jesse and Jessie Sinclair were two of the most popular kids in school. Twin
brother and sister both the sexy brother and sister were tall and thin with
shoulder length blond curls and bright blue eyes. Unbeknown to the rest of the
school they were also two of the kinkiest people in the whole town.
One day Jessie lay, lounging, on a sofa at their house, bored. Her 32 E tits
were just about held in by a tight pink top which cut away to reveal her awesome
cleavage. She was wearing a very short pleated skirt which covered very little
of her gorgeous long silky legs as she draped them lazily over the arm of the
sofa.
"I"m bored with school these days," she was saying in her sexy voice, "We need
to make it more interesting."
"What do you mean?" replied Jesse from where he sat on a chair opposite her.
"I mean we should have some fun, a bet."
"On what?"
A wicked grin spread over Jessie"s luscious pink lips, "You know Lizzie
Nichols?"
"Yeah, little quiet girl, dark hair?"
"My sources tell me little Lizzie"s still a virgin," Jessie continued to grin
sexily.
"So?" Jesse still didn"t get her point.
"So, I propose we bet on which of us will be first to take little Lizzie"s
virginity?"
Jesse now finally cottoned on and his own good looking face spread in a
similarly wicked grin: "You"re on, what shall we bet?"
His twin sister smiled even more and said, "Simple, whoever wins can have the
other perform whatever forfeit they want."
Jesse was deeply pleased with this. He didn"t suspect Lizzie Nichols of
harbouring any lesbian tendencies and felt he could easily triumph in this bet
and then, and at this he had to stop himself rubbing his hands with glee, he
could get Jessie to do whatever he wanted. To Jessie he just said: "Deal."
***
Lizzie Nichols was quiet and shy. She tried generally to go unnoticed by people
and it normally worked. Although had she been more confident and popular Lizzie
could definitely be described as attractive as it was she was mostly ignored.
She was small and thin with reasonable sized breasts, she knew plenty of girls
who stuffed their bras to get attention but Lizzie would do anything to avoid it
and kept her 32 C tits covered by big sweatshirts. She had short-ish dark hair
and dark brown eyes and her face was very soft and innocent. Lizzie had been out
with a couple of guys before and certainly hoped to have sex someday, but, as
Jessie had found out, she was still a virgin. Despite her good looks her shyness
kept her back when looking for guys. She deeply wished she could be more like
Jessie Sinclair who had been her friend when they were kids and now was popular
and outgoing.
She never talked to Jessie really any more which is why she was shocked to look
up from her reveries whilst taking books from her locker to see Jessie standing
there smiling at her as Lizzie closed the locker. Jessie leant nonchalantly
against the next locker smiling. Her perfect white teeth standing out against
her tanned face. It was summer and Jessie was wearing very little, a red midriff
bearing boob tube covered her popular breasts and beneath that she wore a short
denim skirt which showed off her long sexy legs. Her blue eyes sparkled. Lizzie
looked at her with a hint of envy, seeing how sexy her former friend was.
"What do you want?" said Lizzie, slightly suspicious.
Jessie"s face was disarmingly friendly as she smiled at Lizzie, "I was just
thinking how we never seem to talk or hang out anymore Lizzie. What happened to
our friendship?"
"We haven"t really been friends since grade school. You"ve got all your parties
and popular friends now."
Jessie"s face softened, looking hurt, "Please don"t be bitter Lizzie. I know we
haven"t got on as well as we might lately but I"m trying to make it up to you.
Look, I"m sorry and if you"ll accept my apology we can start over again.
Please?"
Lizzie looked into her former friend"s deep blue eyes and beautiful face and
knew she didn"t have it in her to be bitter at Jessie, "OK," she said.
The sparkle returned to Jessie"s eyes and her brilliant smile lit up her
attractive face again. "Thankyou Lizzie, I knew I could count on you. That"s
what I like about you, you"re so forgiving. How about we go for a burger after
school and catch up."
Lizzie looked a little sceptical for a moment before finally saying, "Alright,
see you at the fountain at four."
"I"ll be there," smiled Jessie before hurrying off down the corridor, her
sandals clicking on the tiles and her hips swaying in the little skirt that
showed off her pert ass.
Lizzie watched her leave and then turned away to walk to her class, a huge grin
for once on her own face. As she turned to walk off, her head again in the
clouds, Lizzie almost bumped straight into Jesse Sinclair, Jessie"s twin
brother. Lizzie tried not to smile again at the weird situation that had her
meet the two siblings, one right after the other. She looked up at tall Jesse,
into his bright blue eyes, the twin of Jessie"s but not so sparkling.
"Sorry," Lizzie said looking down and hoping to continue on her way with nothing
more.
"No, I"m sorry I startled you Lizzie," replied Jesse, "I was sort of looking for
you actually."
Lizzie just looked back at him with a confused expression. Jesse began to run
his fingers through his long blond curls and looked slightly embarassed.
"You"re not going to make this easy for me are you?" he said, "OK, here goes.
I"ve been quite attracted to you for a long time but have been too shy to just
come out and speak to you so I"ve had to admire you from afar."
"YOU were too shy to ask ME out?" said Lizzie, incredulously.
"A lot of people think I"m like this cool, confident guy," Jesse was saying,
looking bashful, "But when it comes to asking out a girl I really like I"m just
as nervy as the rest of them."
Lizzie continued to look at him, faintly disbelieving, as he attractively but
nervously tossed his hair away from his eyes.
"So about we go out after school today?" said Jesse.
Lizzie couldn"t believe it one of the most popular hunks in school was asking
HER out. Then she remembered she"d agreed to hang out with Jessie after school.
"This is really weird," she said, "But your sister"s already asked to hang out
after school and I can"t go back on my promise."
Jesse"s attractive face darkened and he frowned, "I wouldn"t trust anything my
sister wants you to do."
With that he turned and strode angrily away down the corridor.
"Another time then?" called Lizzie after him before muttering to herself,
"another time then?"
For a few moments she thought on the bizzare coincidence that had her talking to
both twins immediately after each other. Was Jessie really not to be trusted?
Was she trying to break up any potential relationship with her twin? Or was it
Jesse she couldn"t trust? Was he really trying to stop her friendship with
Jessie? Lizzie shook her head to banish these thoughts. She was a trusting
person and didn"t want to think badly of either of them.
***
That day after school Lizzie met Jessie and they went to the diner near the
school to have burgers and a chat. Lizzie couldn"t remember a time when she"d
had so much fun and laughed as much. She and Jessie actually had a lot in common
and Jessie had a wicked sense of humour. Sometimes Lizzie felt her friend could
become a little too insulting about other people but she still found herself
laughing at almost everything she said. When Jessie laughed she tossed back her
luxuriant blonde curls and showed off her perfect white teeth in a way that made
Lizzie quite envious. Throughout the meal in fact Lizzie couldn"t help but stare
with admiration at Jessie"s impressive, large breasts.
At one point Lizzie decided to bring up the subject of her odd meeting with
Jesse earlier that day. She felt totally at ease and comfortable in Jessie"s
company that there was no question about trusting her. So she told Jessie about
the whole meeting.
"And he said not to trust anything you wanted," she concluded.
"That"s odd," said Jessie, her beautiful smiling face for a moment confused, "I
don"t think I"ve done anything to offend him. Tell you what, I"ll go home
tonight and ask him about it."
There was a pause for a few minutes in which both girls just sat eating their
burgers before Jessie said: "So, you"ve been asked out by one of the most
popular guys in school, what do you think?"
"To be honest, after he stormed off I don"t know if we"ll ever go out. Anyway
I"d be really nervous, I"m not good with guys."
"What you need to do is not be so shy. You need confidence and the first thing
is to look confident. You"re an attractive girl, I wouldn"t hide everything
you"ve got under baggy sweatshirts and jeans. If you want guys to like you
you"re gonna have to show off your assets."
"I"m not sure I"m really up to that," Lizzie replied.
"Don"t worry I"ll help. Tomorrow, after school, we"ll go shopping for a new sexy
wardrobe."
So Lizzie went home that night happier than she"d been in a long time at the fun
she"d had with Jessie that afternoon. She smiled to herself at the prospect of
spending more time with her the next day. Jessie was gorgeous, funny and popular
and Lizzie admired her and hoped that by spending time together she could be
more like her.
***
The next day Lizzie met Jessie after school again and Jessie whisked her off to
the nearest shopping mall. That day Jessie had introduced Lizzie to all her
popular sexy friends from the cheerleading squad and talked about how great
Lizzie was. From then all the cheerleaders and popular girls would say hi to
Lizzie and make conversation with her and so Lizzie seemed to everyone at school
to be more popular.
That afternoon Jessie was still thoroughly amusing and entertaining and again
Lizzie hardly remembered when she"d laughed so much, but she was also very
helpful in finding Lizzie a new sexy and attention grabbing wardrobe.
"First thing is," Jessie was saying, "that you"ve got gorgeous breasts if you
don"t mind me saying. You can"t hide them away, you"ve got to show them off,
it"s the best way to get a guy"s attention. Just look at how much attention I
get from guys just because of these."
As a result of this Jessie took Lizzie first to an underwear store where she
showed Lizzie push-up bras and how they could enhance her tits. Jessie came into
the fitting room with Lizzie as she tried the bra on which Lizzie didn"t dare
comment on. As her friend brushed her hand across Lizzie"s smooth skin helping
to fasten the bra Lizzie felt a tingle of pleasure run through her body and her
exposed nipples get hard. Fortunately she felt Jessie hadn"t noticed anything.

Impressed with the effect the bra had on her breasts Lizzie decided to buy it
and Jessie continued to take her round fashionable clothes stores until Lizzie
had quite a full sexy wardrobe. All the time Lizzie felt so comfortable and
entertained in Jessie"s company. She had no idea why Jessie had suddenly decided
to be friends with her but she was very glad she did.
***
The next day Lizzie shocked people at school and drew many admiring glances from
guys when she turned up in her new sexy clothes. Her 32 C tits now stood proudly
out in a push-up bra and she wore a black halter-neck top that showed off her
cleavage. Beneath this she wore a knee length denim skirt and heels that made
her short frame slightly taller. To top this off sh had styled her hair in a new
sexy way and now wore pink lipgloss and some understated make-up. As she walked
to class Lizzie felt many eyes on her sexy body and surprisingly she didn"t feel
embarassed. Jessie was right, her sexy clothes had made her feel more confident
and as she walked now she gave a sexy sway of her hips as she"d seen Jessie do
and this encouraged even more open mouthed staring from guys she"d thought were
out of her league before.
Just before she came to class Lizzie ran into Jesse again.
"Hey Lizzie," he said, "You look great." Lizzie felt herself blush under her
make-up, "listen, I"m sorry for the other day, I just don"t feel you should let
my sister push you around. Anyway, I"d still love to have that date some time."
Happy that her sexy new look was already paying off Lizzie agreed to go to a
movie with Jesse the next Tuesday, that gave her six days to get Jessie"s advice
and guidance on how she should behave. She walked into class with a grin on her
face, feeling a lot happier and more confident than ever before.
"You know, you should smile more often," Jessie had said, "It really makes you
look good."
***
Over the next week Lizzie spent all her time with Jessie and her friends, it was
fun and entertaining and Lizzie felt on top of the world. Jessie"s friends were
quite nice and fun, but it was Jessie herself with whom Lizzie felt really
great. She was beginning to feel Jessie liked her a lot too as Jessie would
spend more and more time with her than with her other friends.
Lizzie didn"t want to admit it, even to herself, but she began to wonder whether
her attraction to Jessie was more than just friendship. Sometimes, accidently,
Jessie would brush her hand or her breasts against Lizzie"s skin and Lizzie
would again feel that electric tingle of arousal. She found herself when nobody
was looking just getting lost, staring at her friend"s cleavage and her
beautiful face and long legs.
Over the week Jessie continued to give Lizzie helpful advice, not just on dating
her twin but on guys in general and Lizzie was forever grateful for this as much
as her attractive friends entertaining sense of humour. One day, it was the
Monday of the week of Lizzie"s date they were talking about this and Jessie
said.
"Do you mind if I ask you a personal question?" Lizzie shook her head, she felt
totally comfortable and trusting towards Jessie, "You"re still a virgin aren"t
you?"
"How did you know?" said Lizzie.
"I just notice these sorts of things. Don"t worry, I"m your friend, I won"t tell
anyone. It"s just that you"ve got to realise Jesse is obssessed with sex and he
might only want to date you to get into your panties. Just remember you don"t
have to do anything you don"t want."
"Thanks," said Lizzie.
***
"I want to call off the bet," Jessie was saying, voice raised in argument with
her twin.
It was seven in the evening of the Tuesday of Jesse"s date with Lizzie. Jessie
and her twin were arguing over their bet.
"You can"t just call it off, you"ve agreed to it. You know I"m gonna win, little
Lizzie doesn"t stand a chance tonight and you"ve just helped me with all your
efforts to make her sexy."
"I don"t want to be involved in this any more."
"Why not? Just because I"ll win, don"t worry I"ve got plenty of forfeit ideas
for you," Jesse grinned wickedly.
"It"s not right," Jessie was saying, "I don"t think we should corrupt her.
Lizzie"s a sweet innocent girl and I want no part in it."
Jesse burst out laughing, "I can"t believe it, you"ve actually fallen for her.
Well this will make it interesting when I fuck her till she passes out. You know
you can"t pull out of a bet now, you"ve given your word."
Jessie looked at the floor, head bowed, knowing Jesse was right. Jesse grinned
wickedly.
"Tonight your delicate little beloved will be corrupted for ever."
He laughed and walked out of the house on his way to pick Lizzie up, leaving
Jessie despondent.
***
Lizzie arrived at the door in a little pink baby t-shirt, tightly showing off
her curves and revealing her belly button and a knee length skirt. Her dark hair
was again teased into a sexy style and she wore more shiny pink lipgloss. Jesse
had to admit that his sister had taste Lizzie was both sexy and innocent. He
smiled to himself thinking soon he"d strip her off that innocence.
The movie was not that great but Lizzie did enjoy Jesse"s company although
sometimes she felt him getting a little too close for comfort. He had put his
arm round her which she enjoyed she felt safe and happy, but she wasn"t so sure
when he put his hand on her bare knee and began to stroke her thigh. She moved
his hand away, it made her feel uncomfortable. Although Jessie had her hand on
Lizzie"s thigh a lot for some reason Lizzie felt far more comfortable with
Jessie than she ever did with her twin. At one point Jesse leaned over to kiss
her but Lizzie pulled away.
Despite these moments Lizzie had fun on her date and generally enjoyed Jesse"s
company, although not such hilarious fun as his twin Jesse still entertained her
and made her laugh and Lizzie didn"t think twice when he invited her in and sat
her on the couch.
Jesse handed Lizzie a drink and she took it but before she could drink any he
leant over to kiss her. This time Lizzie didn"t resist and she felt happy as
Jesse placed his lips on hers and forced his tongue into her mouth. Lost in the
joy of the kiss Lizzie didn"t immediately notice that Jesse"s hand had pushed up
the little pink t-shirt and was feeling her breast. The other hand was running
under her skirt, inside her thighs towards her panties.
Realising this Lizzie pushed him away. For a second a look of anger passed over
Jesse"s attractive face and Lizzie was reminded of his reaction when he had
first asked her out and she"d told him about Jessie.
"I"m sorry," she said, "I"m just not ready for that yet."
Lizzie thought he would sit back, understanding, but at the back of her mind she
remembered what Jessie said, "he might only want to date you to get into your
panties." At that moment she felt herself pinned down on the couch by one of
Jesse"s strong arms.
"I"m afraid you don"t get to choose here," he said, unbuttoning his jeans with
his other hand to release his erect cock.
He began to push up her skirt again with a triumphant leer on his face. Lizzie
felt scared and shocked by what was happening but again Jessie"s words came to
her, "you don"t have to do anything you don"t want to." This gave her strength
and she brought her knee up into his groin. As Jesse rolled back in pain she
slapped him and ran, straightening her skirt as she went, tears welling up in
her dark eyes and mascara running across her cheeks.
As she ran from the house Lizzie ran straight into Jessie who was just coming up
the drive. Jessie was dressed in a tiny pair of denim cut-offs that showed the
full length of her tanned smooth legs and a pale yellow blouse with some off the
buttons undone to reveal her cleavage. Lizzie looked through the tears into
Jessie"s deep blue eyes.
"What"s wrong? What"s happened?" Jessie said, instantly concerned at the sight
of Lizzie in tears.
Through the tears Lizzie managed to get out the story of how Jesse had tried to
force himself on her.
"You were right about him," Lizzie sobbed.
"I didn"t want to be," said Jessie.
She opened her arms and allowed her friend to fall into them as Jessie hugged
her affectionately. A wet patch appeared on her blouse as Lizzie"s tears
continued to flow as she pressed herself against Jessie"s ample bosom.
"You shouldn"t be alone tonight," Jessie was saying as Lizzie pressed against
her curvaceous body, "Come inside, I"ll look after you."
Lizzie smiled at her friend through her tears, relieved that she knew she could
trust and care for Jessie, as she followed her into the house. Avoiding Jesse,
Jessie led Lizzie up to her bedroom and they sat on the bed together. Jessie
continued to hug her friend as Lizzie continued to cry.
"It"s OK," Jessie continually re-assured her as she began to plant kisses over
her friend"s face.
Lizzie looked up from her tears into Jessie"s beautiful blue eyes. For what
seemed like ages but was actually just a few seconds they stared into each
other"s eyes. Then, slowly, Jessie took Lizzie"s head in her hands, and gently
planted a kiss on her inviting shiny pink lips. Instinctively Lizzie opened her
mouth and took in Jessie"s tongue, caressing it with her own and closing her
eyes, savouring the kiss. The feel of her friend"s fine breasts pressed against
hers was causing a feeling of arousal to run through Lizzie"s body and she felt
her nipples becoming erect.
They broke from the kiss and Jessie slowly slid Lizzie"s little pink t-shirt
over her head, all the time maintaining eye contact as Lizzie was lost in the
beauty of Jessie"s eyes and face. Then Jessie slowly unzipped and slid off
Lizzie"s skirt until her friend was dressed just in a white bra and little white
silk panties. Jessie again leaned over to kiss her friend as Lizzie was lost in
the joy of the moment. As she continued to kiss her Jessie unclasped her
friend"s bra and let it fall to the ground. Lizzie felt her free, pert breasts
even more erect and her virgin pussy become wet.
Breaking from this kiss Jessie bent down and began to plant further kisses over
Lizzie"s pert breasts with her luscious red lips. Looking down Jessie could see
a sexy red lipstick mark over one of her tits. She felt herself getting wetter
as Jessie reached down and gently ran her hands over Lizzie"s wet pussy through
her little white panties.
Finally Jessie knelt down in front of her friend as she sat on the bed. Lizzie
was now so wet that her white panties were almost see through as Jessie slid
them down her smooth legs to reveal Lizzie"s virgin pussy lips and a small
amount of fluffy downy pubic hair. Lizzie"s pussy was wet and her clitoris
erect.

Jessie paused for a moment and looked up into Lizzie"s eyes, her face, framed by
gorgeous blonde curls with her lipstick slightly smudged was the most beautiful
thing Lizzie had ever seen and as she looked down on Jessie she could see right
down her gorgeous cleavage through her open blouse. Looking up into Lizzie"s
eyes Jessie said again in a reassuring yet sexy purr:
"You don"t have to do anything you don"t want to,"
Looking down on her gorgeous friend, whose attractive face was inches away from
her erect clitoris Lizzie smiled:
"This is exactly what I want."
Jessie began to kiss around Lizzie"s swollen pussy lips as Lizzie moaned in
pleasure gradually Jessie began to lick along Lizzie"s slit before beginning to
suck on her friend"s erect clitoris. Lizzie moaned and groaned ever louder with
the expert pleasuring her friend was giving her as she began to play with her
own breasts. Jessie looked up at Lizzie, and was re-assured by her friend"s
expression of ecstacy.
Lizzie couldn"t hold her virgin self in much longer against Jessie"s expert oral
assault and with a final, extra loud, moan of pleasure she felt her body shake
with her orgasm, it felt like electricity running through every nerve of her
body as it shook with joy and she squirted her juices into Jessie"s mouth.
Finally, her orgasm complete, Lizzie colapsed, smiling, on the bed having just
received the greatest thrill of her life.
At that moment both she and Jessie looked up to see Jesse come in the room
applauding.
"Congratulations Jess, looks like you"ve won our bet after all."
"Bastard," was all Jessie could say as she slapped him.
Lizzie was heartbroken as she tearfully and quickly put her t-shirt and skirt
back on and turned to Jessie through her tears. She"d lost her treasured
virginity all just because of a bet.
"I thought you really liked me," she said tearfully to Jessie, "I thought you
really cared about me. But it turns out your nothing more than a cruel,
deceitful bitch."
Without waiting for a reply Lizzie ran again from the house in tears. Landing a
second, harder, slap across Jesse"s smug, grinning face that made her twin wince
with pain, Jessie took off after Lizzie, finally catching her half way down the
street.
"Lizzie, please can we talk," she said as Lizzie turned her back on her, "Let me
explain!"
The pleading tone in her voice and the sound of her tears and emotion made
Lizzie turn back towards Jessie. Sure enough there were tears and a pleading
look in her friend"s gorgeous blue eyes.
"OK, I only started to hang out with you because of this stupid bet," with that
Lizzie almost turned to walk off again, "At least hear me out," pleaded Jessie
as Lizzie stopped again, "I only hung out with you AT FIRST because of that, but
then I got to knowing how great and fun a person you are."
"Really?" said Lizzie through the tears.
"Really. I had such fun spending time with you. I really did care about you. I
even tried to call the bet off, and tried to warn you about Jesse. I never
wanted to win the bet. What happened in my bedroom there just happened. I never
planned it, I just wanted you to be happy. Come on" she pleaded, "Didn"t you
enjoy it? Didn"t we have fun together?"
"I suppose I did," said Lizzie, no longer crying.
"Then can"t you forgive me? I"d really love to be friends again, I"ve never been
happier than with you."
Looking into her friend"s attractive, perfect face and deep blue eyes Lizzie
knew she really cared about Jessie and couldn"t let her go even for this, she
knew she would forgive Jessie. A smile came to her lips ("you should smile more
often" Jessie had once told her) and she fell into Jessie"s arms and pressed
against her friend"s prodigious bosom. They locked lips in a passionate kiss and
Jessie knew that all was forgiven.
Breaking from the kiss Lizzie was pleased to see the sparkle of pleasure back in
Jessie"s blue eyes and her brilliant white teeth and luscious red lips spread in
a smile:
"And you know what. Because I won the bet we can take whatever revenge we like
on Jesse," she winked . . . .
Part Two - Jesse"s Forfeit
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 . . .
Part Three - Jessie and Lizzie"s Prom
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 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, 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 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:
"So," Lizzie paused for a second before giving a little smile, "Your place or
mine?"
They ended up going back to Jessie"s, knowing Brock and Julie would have gone
back to Brock"s place and Jessie"s parents were away once again, despite her
making a stand that evening Lizzie wasn"t entirely sure she could face her own
conservative parents with her current lifestyle.
When they got inside Lizzie sat down on the couch, suddenly as nervous as she
had been the first time. Earlier that evening she"d wanted to go all the way but
now she really didn"t know. Jessie sat down beside her:
"Are you ok Liz?" she asked, Jessie could always tell if something wasn"t ok
with her girlfriend, "You know we don"t have to do anything you don"t want, we
can just sit here and talk."
Jessie put one arm around Lizzie"s shoulder and began to stroke her gently and
softly like a child as Lizzie"s courage began to come back to her. Lizzie bent
and began to kiss her friend"s long bare white neck with gentle soft kisses
moving gradually down towards her breasts. Jessie reached behind her back and
slowly unzipped her tight pink dress, allowing her massive round breasts to fall
free into Lizzie"s waiting lips. As Lizzie planted kisses all over her friend"s
gorgeous round tits she felt herself getting hot and knew Jessie must be feeling
similar as her friend"s nipples were hard and erect.
Lizzie allowed Jessie to stand and drop her pink dress to the floor revealing
her pink panties and long smooth legs. Lizzie pushed her friend back onto the
couch, stripped off her panties so Jessie was dressed in just her long pink
gloves and pink pumps, and thrust Jessie"s legs wide open. Already Jessie moaned
with the thrill of Lizzie"s newfound eagerness. Although Jessie had eaten Lizzie
out, so far Lizzie had been too nervous to return the favour although she knew
Jessie was desperate for it.
***
Brock looked in shock down at Julie"s cum stained body and at the cum that
covered his own hands, suddenly he realised that for all her enticing sexy body
he had been jerking off a big hard cock. This realisation was followed on a
couple of seconds later by the even more shocking realisation that he didn"t
care. Not only didn"t he care but he was actually quite turned on by the whole
situation.
Julie lay exhausted on the bed and was quite surprised when Brock bent down and
began slowly and leisurely to lick the cum from his body. As Brock"s tongue
lingered over Julie"s smooth thighs she could feel her own cock become hard
again and Brock took this as an opportunity to pounce.
Surprising even himself Brock grabbed Julie"s firm erect member with one hand
and began to take it into his mouth. Inexpertly, but eagerly and rapidly Brock
began to suck Julie off, bringing out sensual moans of pleasure from her pouting
dark lips. He felt her hard dick throbbing in his mouth and felt a little
disappointed when she withdrew it.
Still dressed in the corset that gave her large breasts and a perfect hourglass
figure Julie stood up and grabbed Brock with surprisingly strong arms and threw
him face down onto the bed. Before he was fully aware what was happening he felt
Julie"s cock thrusting into his tight virgin ass. He tried to struggle to escape
from her painful thrusting but soon he embarrassingly began to relish the
pleasure of how it felt to be ass fucked by this beautiful, well hung girl.
Brock couldn"t hold himself in any longer, the stimulation in his virgin ass was
too much and he felt an orgasm spreading through his body before her emptied
himself all over the sheets of his bed. As if this was some signal Julie too
threw back her long black curls and with one final, hard thrust filled Brock"s
waiting ass with her hot white juices.
Finally both collapsed, exhausted, on the bed in a pool of cum, wide grins on
both faces as the new experiences of tonight had certainly been entertaining
ones.
***
Lizzie paused for a moment, just staring at Jessie"s enticing shaved cunt and
erect clitoris. After that moment she dived in and began to eagerly lick at her
friend"s slit and relieve her throbbing urges in a way that tried to imitate the
pleasure Jessie had given to her. Jessie"s stylish blonde hair was thrown back
and she was sensually groaning with joy as her hands ran across her erect
breasts and played with her nipples.
"I"m cumming," Jessie screamed with joy as she squirted her juices into Lizzie"s
waiting mouth.
"Lizzie that was wonderful," Jessie said as her friend finished drinking her
juices and stood up, "You were great," Jessie smiled her brilliant white smile,
eyes sparkling, "I think you deserve to be rewarded for that."
Lizzie was still dressed in her cleavage enhancing black halterneck which she
let fall to the floor, her own eyes lit up with anticipation. Beneath the sexy
dress Lizzie wore a low cut black lace basque and black stockings.
Jessie walked over to her and took Lizzie into her arms, the girl"s erect
breasts pressed against each other as they engaged in a tongue wrestling kiss
while Jessie fumbled for the clasp on Lizzie"s underwear and let that too fall
to the ground showing off her friend"s gorgeous pert naked body. Lizzie could by
now feel herself really dripping wet as her pussy cried out for the relief that
she was desperate her best friend would provide.
As if able to read her friend"s dirty thoughts Jessie pushed Lizzie back onto
the couch and pulled out from behind it an eight inch double ended strap-on that
she attached to herself. She looked down at Lizzie and smiled re-assuringly.
"Come on Liz, now it"s time to go all the way."
Lizzie smiled back at her, feeling slightly nervous but eager to get the relief
of her friend"s strap-on inside her. Lizzie had been worried that it would be
deeply painful but as Jessie thrust the prosthetic dick into her pussy, deeper
than anything had ever been before, the extreme wetness of her arousal acted as
a lubricant and Jessie easily slid in and out of Lizzie"s tight pussy.
The feel of that hard prosthetic dick inside her and the sight of Jessie"s
gorgeous face in ecstasy at fucking her friend and her large wobbling breasts
which Lizzie began to play with all combined to make Lizzie more deeply aroused
than ever before. The shouts and screams of both girls" pleasure was enough to
wake up the whole neighbourhood as both raced towards a climax. Finally and
almost simultaneously both girls felt their orgasms grow. Lizzie felt her cunt
tighten around the rubber dick and her orgasm spread, shaking with pleasure,
through her whole small body.
Both girls continued to cum for what seemed like forever before Jessie collapsed
on top of her girlfriend"s beautiful little body. They lay like that for almost
an hour, happily content in each other"s arms. Lizzie"s head pressed against
Jessie"s massive chest. In those moments Lizzie felt she finally knew happiness,
and this was it, lying exhausted in her sexy friend"s safe arms. Truly this had
been a prom night to remember.
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