Sport Model
JL Williams
Bobby carefully placed the gym bag in the rear of his closet. He double-
checked the lock on the Nike bag, and as he piled boxes around his stash
he sighed. It seemed like he never got to dress very much anymore. His mom
finally got enough seniority at the hospital to work days. He should've
been happy to see her, and have dinner with her....but it took away his
time to dress. Bobby turned off the light in his closet and headed
downstairs to start dinner in his own drab clothes.
Bobby wondered about his fate as he started dinner. He was 5'6" and 120
pounds. He was popular at school. Despite his size he was a three-sport
athlete. He had finished eighth in the state cross-country finals last
year as a junior. He was picking up his running now this summer...hence
the spaghetti dinner. Even though he was short, he would be the starting
point guard this year on the basketball team, and it was going to be a
very good team. His first love, after dressing, was baseball. He would be
starting again this spring at shortstop. Not bad for a runt he thought.
His grades were good too-a solid B+ average. He didn't hold out much hope
for a division one scholarship, but five division three schools were
putting together excellent grant in aid packages and had contacted him. He
wanted to go away to school, but if worse came to worse, he could do like
his sister Grace, and go to the local junior college before going to
State.
Dinner was ready when Bobby's mom, Jean, arrived. She looked great in her
nurse's uniform, but she was tired. She had been a single mom since Bobby
was two and Grace was five. Her husband just didn't come home from work
that fateful day. He had some gambling debts, and foul play was always
suspected, but never proven. She worked to raise her kids and was proud of
her success.... and theirs.
She kissed Bobby on the cheek and thanked him for making dinner. She
poured herself a glass of wine, sat down and started asking him about his
day. Bobby said that he had gotten out early at the golf course and was
done caddying by 2:00, he came home and shot hoops and "stuff"...the
thought of what he secretly meant by "stuff" made his cock twitch. Bobby's
mom worked in the emergency room at the area trauma center hospital, so
she always had great stories. They talked about their days until dinner
was over. Jean, Bobby's mom, insisted on cleaning the kitchen after
dinner. She asked if he was going out. He said no he had to get up early;
there was a tournament at the golf club the next day and Mike Williams was
picking him up at seven in the morning. Jean said she worried about him
not going out more, but he said he was busy enough. They were both in bed
and asleep by ten o'clock that night.
Friday morning dawned clear and warm for a July day in the Midwest; but
Bobby was up before that. He got in six miles before six AM. This Friday
would be a perfect day for golf. After his run Bobby was feeling great. He
took a hot shower, ate some breakfast and bounded out of the house to the
sound of the horn of Mike's car. They had been friends long enough to be
comfortable to just listen to the radio on the short ride to the club.
The caddy master liked Bobby; and he knew that Bobby needed the money, and
that he was dependable and always polite. The caddy master gave Bobby a
good loop, one that would give Bobby a great tip whether he won the three
day tournament or not. Bobby and Mike wound up in the same foursome that
was great for Bobby, which meant he wouldn't have to wait around for a
ride home, or worse have to walk, if Mike left early. The idea of getting
a car was one that Bobby knew was out of the question.
After their round Bobby and Mike cleaned the members' clubs, and headed
off for home. Mike dropped Bobby off in front of his house. Bobby begged
off going out with everyone that night, using having to get up early and
get his Saturday long run in before caddying as a pretext. Actually his
mom was going into the city to go out with some old high school friends
and wouldn't be home 'til late. He could dress tonight!
When Mike pulled up in front of Bobby's house there was all kinds of
activity going on next door. There was a moving van and a couple of
unfamiliar cars. Bobby remembered that the Simon house had sold, but he
didn't know that today was move-in day. He told Mike that hopefully there
would be beautiful triplets moving in next door. Mike laughed, and said
they'd have to be really beautiful to look better than Cindy. Mike had
dated Cindy for two years and Bobby thought that Mike was right. She was
drop dead beautiful. Before Bobby could get his gear out of the car, Mike
had called Cindy. Mike yelled that the cheerleaders were back from camp,
and Cindy would be able to fix Bobby up tonight. Bobby thanked Mike for
that but he really needed to sleep and run in the morning. Bobby knew that
Mike would be hanging with the football team tonight. Despite Bobby's jock
status, the football players, at least the core Neanderthal group, tried
to bully him. However, Bobby had enough friends on the team to keep them
at bay, but he always felt uneasy around the Paul Taylor group.
Bobby walked over towards the movers. He spotted a woman in her early
forties directing the movers, and went over to introduce himself. She was
his new neighbor Rita Wilson. She seemed very nice, and was impressed that
a teenager would introduce himself. She called out two names. Bounding out
of the house was Pete Wilson. Bobby recognized him. He was the starting
quarterback at State two years ago, and destined to be a number one pick
in the NFL draft until he trashed his knee in the Cotton bowl.
Pete said hi to Bobby and turned to his mom and said they were just about
done. He added a nice to meet you kid, turned and with only a slight limp
bounded back into the house. Pete passed someone who looked to be Bobby's
age. He came out of the house at a snail's pace. He had body language that
screamed, "Let me be anywhere but here!" Rita called to him, "Tommy don't
dawdle, there is someone here I want you to meet."
Tommy was almost six feet tall and very handsome. He would have looked
even better if he hadn't been scowling. His mom introduced them to each
other, and they discovered they were the same age. Bobby immediately knew
why Tommy was scowling, Bobby thought about how horrible it would be to
transfer schools in high school, let alone your senior year. Bobby tried
to be friendly, and even offered to fill Tommy in on school, but Tommy
would have none of it. He mumbled something about it being nice to meet
Bobby and wandered back into the house.
Rita tried to apologize for Tommy, but Bobby said not to worry. He
understood. He said he wouldn't want to switch schools in his senior year
either. Rita thanked Tommy, and asked where his parents were. He explained
about his household, and said he was sure his mom would stop by tomorrow.
With that, he headed home...to dress....but by the time he got home; he
was paranoid about his new neighbors coming over. He wasn't sure what he
should do. He puttered around the house for a while, and then as soon as
it was dark he couldn't resist the siren call of his bedroom.
He donned his favorite panties, nylons and garter belt, but kept them
hidden under a pair of jeans until almost nine o'clock. Bobby then put on
his sister's prom dress, a strapless slinky number in shocking pink. Bobby
crammed his feet into the matching shoes, and applied a little make up. He
did what he could with his hair, but it never looked like he wanted it to
look. Bobby waltzed around his sister's room secure in knowing the doors
to the house were locked and the shades and curtains in his sister's room
were drawn. Bobby imagined he was dancing with a handsome man, one who
would take him in his arms and take his breath away with hot steamy
kisses. One who would late take him to bed and make sweet sensuous love to
him. When it came time for the love making in Bobby's fantasy he carefully
hung up his sister's dress, and donned one of her satiny baby doll
pajamas. Bobby lay down on her bed and masturbated as he thought of this
faceless lover taking him, and Bobby taking him into "her". As always once
he came stripped off the clothes, put every thing carefully away, and
removed the makeup.
Saturday morning dawned as a repeat of Friday. Bobby had run twelve miles
by the time Mike was scheduled to pick him up. Mike was right on time and
they headed to the country club for the second day of the tournament. Once
again Mike and Bobby finished at about the same time, so Bobby got a ride
home. Mike said a bunch of the kids were going to Katie White's house that
night for a party. Did Bobby want to go? Since Bobby knew his mom would be
home, and there was no chance of dressing, he said sure. Mike said that
the party would start at about 8:00 and he'd meet Bobby there. Bobby
bounded out of the car and as he looked up he saw him mom talking to their
new neighbor.
Jean and Rita were laughing and getting along like old friends. Bobby
walked up and they greeted him warmly. Bobby's mom was pleased because he
had been so polite and outgoing yesterday. Jean and Rita asked him about
the golf tournament, and he said it was fine; his "loop" had a chance to
win some serious money, which would transfer into a good tip for him. Jean
asked what he was going to do that night. He told her about the party at
Katie's house. Jean said they would be eating with Rita and her family,
and maybe Tommy would be interested in going to the party and meeting some
of his soon to be classmates. Bobby absently said fine, and headed into
the house to clean up. After seeing Tommy yesterday, he was sure he
wouldn't go.
Dinner was terrific. Mrs. Wilson was a great cook. Pete was a lot of fun
and he seemed interested in Bobby's athletic ability. Only Tommy was
quiet. Sullen really, he ate quietly and looked at Bobby like he was a
dangerous intruder into his home. Jean suggested that Tommy go to the
party with Bobby, and Tommy flatly refused. He excused himself from the
table and went to his room. Mrs. Watson tried to make excuses for her son,
but Pete cut her off. He said that Tommy was being a brat and that he'd go
up and take care of the "little shit". Out of nowhere, Bobby said, "Pete
if you don't mind, maybe I can help. Let me go up and talk to Tom." Both
mothers were impressed, and Rita Wilson thanked him profusely.
Bobby wandered up to Tommy's room; it was the only one with the door
closed. He knocked, and called Tommy's name. "Go away!" Was the response
to the knock. Bobby ignored this and brazenly entered. Bobby saw Tommy
laying face down on the bed. He appeared to be crying. Bobby walked over
to the chair by the desk and quietly asked why he was taking this move so
hard.
Tommy said that Bobby wouldn't understand. Has Bobby asked the question
again, he was given the same answer. Finally, after an awkward silence,
Tommy shot up and blurted out that he was gay. He said that his mother and
brother brought him out to this God forsaken suburb to get him away from
his friends in the city and to make him straight by making him live in
this "white bread" environment.
Bobby sat there stunned. He couldn't believe it. His mind was racing.
Finally he said you know it won't work. You are what you are. In fact
there is a school sponsored GLBT group. I know the president and would be
happy to introduce you to him.
Now it was Tommy's turn to be shocked. He was totally surprised by Bobby's
reaction. He thanked Bobby for the offer, but he felt he needed more time
by himself before meeting new people.
Bobby said that he just wanted the time to feel sorry for himself. The
president and his boyfriend would be at the party tonight. Tommy should
go, and if he really didn't like the party they could leave. Tommy
reluctantly gave in, and agreed to go. Bobby said he would pick Tommy up
at 8:15, no sense being too early. He said just wear shorts and a golf
shirt.
When Bobby told the women that Tommy was going Mrs. Wilson hugged Bobby so
tight she almost squeezed all the air out of his lungs.
As Tommy and Bobby walked to the party, Tommy did all the talking. He
explained how his dad, now divorced from his mom, couldn't understand why
he wasn't like his brother. His brother called him an embarrassment. His
mom tried to understand, but she couldn't. So she decided that moving to
the suburbs would "cure" him. Bobby listened, and silently empathized with
him.
The party was in full swing when they arrived. Katie's house had a huge
back yard and her folks had put a temporary dance floor in the middle of
the lawn. Her folks were at the entry point of the yard, and Bobby
introduced Tommy as a new kid in the school to them, and then brought him
around to his friends, both the boys and the girls. Finally, they happened
on Jack Moore and Bill Jackson. Bobby introduced Tommy to them and added
that Tommy only came to the party to meet them. Jack and Bill got the
idea, and Bobby left them to talk.
Bobby found Mike who was talking to three of Bobby's running mates on the
cross-country team. As the night wore on, he danced, talked to a bunch of
other folks and kept an eye on Tommy. Tommy seemed to be smiling and
animated as he talked to Jack and Bill. Bobby smiled. He was glad to have
introduced them. But his smile faded as he saw Paul Taylor and four of his
football buddies half stumble into the party. Bobby looked desperately for
Katie's parents, but they must have gone into the house. The Neanderthals
headed straight for Paul and Jack, and Tommy. Bobby instinctively headed
to the confrontation. He could hear "faggots" as he neared them. Tommy
stepped up to confront Taylor, but Bobby cut in front of him. He told the
middle line backer who towered over him by at least nine inches, to leave
these guys alone and as a matter of fact if they were smart they would
leave the party period.
Paul Taylor leaned down into Bobby's face and sneered. Well look who we
have here the runt jock he said through his beer breath. Are these faggots
your friends? Bobby sneered back that they were and they were better
friends and better people than him and the knuckle dragging jerks he was
with. Paul stepped back to hit Bobby, but Katie's dad called and demanded
to know what was going on there. Bobby looked toward Mr. Green. Paul
didn't stop; he caught Bobby on the side of the head, and knocked him out
with one punch.
When Bobby came to, he found the party over. Tommy was sitting with him
along with Mike, Cindy and the Greens. Bobby found out that the cops had
come and had taken Paul Taylor and his buddies to the police station. Mr.
Green had called Bobby's mom and she was on her way to get him.
On the way home Tommy thanked Bobby over and over, but also said that he
could take care of himself. Bobby said it was his responsibility since he
invited Tommy. Jean wanted to know what started the fight, and Bobby said
that Paul Taylor was drunk and wanted to pick a fight with the new kid.
Bobby insisted on caddying the final day of the tournament, and was
waiting for Mike at 7:00 Sunday morning. Luckily Sunday was an off day for
running 'cause Bobby still had quite a headache. Mike cruised up to the
curb right on time. He whistled softly as he saw the shiner and bruise on
the left side of Bobby's face. Bobby asked him not to make him laugh
'cause he had a headache, and his face really did hurt.
The day went by with a minimal amount of comment, and Bobby's loop came in
third. Good enough for a lot of money, money that Bobby would give to his
mom for his college fund.
On the way home Mike was on his cell phone the whole ride. Evidently Paul
Taylor had acted up at the police station. He was still in the holding
cell, and it looked like he was in jeopardy of being kicked out of school.
The rest of his friends were released and looking for Bobby. Mike looked
over to his friend and suggested that he go on vacation for about six
years. Paul's friends were bad, but once Paul was out of police custody he
would really be looking for Bobby...to do some permanent harm. Bobby was
nervous, but he tried not to show it. He said Paul got in a lucky punch,
and next time the outcome would be different. He knew he didn't believe
it, but he had to put on a brave front.
Mike dropped Bobby off and waved good-by. Mike liked Bobby a lot, but he
made the mental note to put some distance between himself and his friend
for a while...his physical well being would depend on that. When Bobby
entered the house he found his mom on the telephone. She motioned for him
to sit down. When she hung up she said that she was talking to the police,
they wanted him to press charges. Bobby said no. He said that it would
make things worse. It was just a high school fight, and it should end
there. Besides, he knew this went to court Tommy would get dragged into
it, and he didn't want that. Jean, asked him to reconsider. Then she
changed the subject. She asked how he did caddying, and he gave her the
money to deposit. She then suggested he go to bed, and get some rest. He
agreed.
The next few weeks were actually uneventful. Paul heard that Bobby was not
going to press charges, and while he boasted that it was because Bobby was
afraid of him, he also stayed away from Bobby. Not because he was that
smart, but because the football coach threatened him with the beating of
his life if he did anything else stupid this summer.
Bobby noticed that Mike was becoming scarce, and he wound up spending time
talking to Tommy. It turned out that Tommy was bright, funny and very
interesting. He regaled Bobby with tales of the big city, and Bobby said
they needed to make a road trip. Tommy agreed, and said if Bobby didn't
mind, his mom would feel much better letting him go to the city if Bobby
went with him. That was on a Sunday night, and the plan was to head into
the city Saturday night, if Tommy could get the car.
Monday the golf course was closed and Bobby's mom was at the hospital. It
was a cold and rainy day that was all right in Bobby's mind 'cause he was
going to spend most of the day dressed. After running in the morning, and
having breakfast, it was time to transform. He took his time. He took a
bubble bath, and then he shaved what little hair he had on his legs and
arms. The rest of his body was hairless already. He took out his Nike bag,
unlocked it and decided that since this was the first time he was dressing
without the shiner from Paul, we was going to go all the way. He took out
the nail polish, which he rarely used, and did his toe and finger nails in
soft pink. Once they dried he put on his garter belt and nude hose. He
then donned a black bra and inserted the two breast forms he had bought
through the mail. He put on a robe that his sister had left behind and
went into the bathroom to put on his make up. Forty minutes later he
emerged. Bobby was happy with the work he had done. The lipstick matched
his nails, and he felt like he had done his best work on his eyes...ever.
He had combed his hair into what he called his Lorrie Morgan look. He
added the clip-on earrings from his stash and the choker; he had a passion
for chokers. He then went to his sister's room. He knew exactly what he
wanted to wear. He went right for her black dress. He had to tuck his
erection down before he put it on. He loved the dress. It fit him, and he
always felt sexy in it. He put on the three inch black patent leather
shoes and turned to look into the mirror.
Bobby sighed, he loved dressing, and it was so relaxing. His plan was to
spend the next few hours dressed, for now in the sexy black dress, and
later in the scanty baby doll pajamas, and while dressed in them, he would
masturbate. Then reluctantly he would remove his make up and nail polish,
and return to being "the runt jock". He frowned as he thought how that
comment from Paul had stuck with him. Bobby decided to head downstairs and
get something to drink. He walked down the stairs with the confidence of
someone who has done it in high heels many times. When he hit the landing
the front door burst open, and Tommy entered, without knocking and his
coat over his head to keep the rain off of him. When he pulled the coat
down he saw Bobby, frozen in terror.
Bobby couldn't move. Tommy couldn't either. Finally Tommy said, "Bobby you
are beautiful. Don't worry, I love the look." Then he smiled. Bobby
couldn't believe it, but he started to cry. Tommy moved to his new friend,
and put his arm around him, and walked him to the living room, and gently
sat him down on the couch. Tommy positioned himself across from Bobby and
sat on the footstool. He handed Bobby his handkerchief and reiterated how
pretty he looked.
It took Bobby a while to compose himself, and he finally thanked his
neighbor for being so understanding. Tommy laughed, and told him that
everyone had their little secrets. Some, like the two of them are a little
more out of the ordinary. Then Tommy peppered him with questions. How long
had he been doing this, was he gay, had he gone out of the house dressed,
did anyone else know, and on and on. Bobby quietly answered all the
questions. He said he'd been doing it for a long time; he was no different
from the rest of the cross-dressing community...at least what he knew from
the internet, he had never gone out of the house, and he didn't think he
was gay.
Bobby finally felt okay with Tommy, and Tommy told Bobby not to worry, he
wouldn't hit on him. He explained that he was a "bottom" and that he and
Bobby would probably wind up fighting for the same man. That got a laugh
from Bobby. They wound up spending the rest of the morning talking and
laughing. Bobby even fixed lunch for the two of them. Finally Bobby said
he had to change, and clean up. Tommy said he'd come by after dinner he
had a great idea for Saturday night. Bobby, kissed him on the cheek and
held Tommy's hands, and gave him the most heart-felt thank you he had ever
said to anyone. Bobby quickly went upstairs, masturbated and transformed
himself back into a boy.
Bobby finished preparing dinner as his mom entered the house. She kissed
him on the forehead, and after putting her coat away joined him for
dinner. She asked about his day, and he honestly told her that he and
Tommy spent a lot of time talking. He also mentioned that Tommy asked if
he could go into the city Saturday night. Jean said she worried about
driving so far. Bobby persisted, and Jean finally relented. She said if
Tommy could get the car, she would let him go. Bobby thanked her and they
cleaned the table together. Bobby offered to wash the dishes, but Tommy
rang the bell before his mom could say anything. She said, "You've done
enough, go!"
Tommy was flush with excitement. He couldn't wait to tell Bobby his plan.
They went up to Bobby's room, and he laid out their Saturday. First, they
would leave at one o'clock. Tommy had talked to two of his friends in town
who were teenaged cross dressers, and they would help Bobby with his
transformation. Then that night there was a dance sponsored by the local
teen adjunct of GBLT in the city. They could go to that and have a great
time.
Bobby was too shocked to answer. First this was the most animated he had
seen Tommy. Second, Tommy was talking about Bobby going out in public
dressed as a girl!! He couldn't do that, could he? Suddenly, Bobby felt
himself getting caught up in Tommy's enthusiasm for this plan. Bobby
opened his mouth to say "no" he couldn't possibly do this, when the word
"yes" came out of his mouth. Tommy was so pleased he hugged Bobby. He said
this would be so great. He said he couldn't wait for Saturday to come.
Bobby could wait. He was scared and was going to tell Tommy he couldn't do
it. But as the week rolled on Tommy kept his excitement level to the point
Bobby couldn't tell him no. On Friday, Tommy told Bobby he didn't need to
bring anything. He told him that Gina and Jeri were very excited to meet
him and to work some magic on him. He also told Bobby that the dance that
night would be fun; it was the first dance in quite a while so it should
be well attended. Bobby nodded dumbly. He was trapped, and while he was
sure this would be a bad idea, deep inside him he was excited. He finally
asked if he shouldn't bring make up or shoes, or something. Tommy said no
the girls were going to have everything.
Saturday dawned gray and rainy. This made it easy for Bobby to skip
caddying. He was up early for his long run, which gave him a lot of time
to think. He couldn't do this and he would tell Tommy that he'd go to the
city and the dance, but dressing was out of the question. Still, when he
got home even though he couldn't take a bath, he scrubbed and shaved
everything he could in the shower. He came downstairs to see his mom
finishing her coffee. She looked up and smiled. She said since Bobby was
going to be gone all day, she was going to see Grace at school. She said
she was going to stay over at Grace's apartment, and she'd be home by noon
or one o'clock Sunday afternoon. Bobby tried to hide his glee. This meant
he didn't have to worry about getting home early. Jean said she was ready
to go, and at noon she pulled out of the driveway.
Bobby was outside by five to one. He couldn't help but bring some "stuff"
(he wasn't going to dress, but just in case he changed his mind). He had
earrings, his ever-present choker, a pair of panties, nylons and a garter
belt. Tommy backed the Wilson's car out of the garage. Rita Wilson came
out and told Bobby how glad she was that he had made friends with Tommy.
She felt so good that Bobby was going into the city with him. Bobby felt
his stomach churn. He was embarrassed and felt like a fraud. He wasn't
helping Tommy, he was abetting his condition; but Bobby also knew there
was no "cure" for Tommy or for him for that matter. Bobby mumbled a "no
problem", and climbed into the car.
Tommy saw the change in Bobby's demeanor and asked what was wrong. Bobby
told him about what his mom said and Tommy replied, "Bobby, this is a
great adventure for you. I am so excited to be doing this. This is partial
payback for your kindness to me. Promise me you'll just have fun...no
guilt allowed." Bobby promised.
At 2:20 Saturday afternoon Tommy rang the doorbell at his friend Gina's
house. Bobby thought he'd faint. They heard "they're here!" squeals before
the door opened. The door flung open and there stood Gina. She was a knock
out. She grabbed Tommy and hugged him. Then she looked at Bobby, and
exclaimed, "She's cuter than you said!" Bobby blushed furiously and tried
to say something, but no words came to him. Gina took him by the arm and
practically dragged him into the house. Inside the house was Jeri, a
statuesque beauty who after hugging Tommy welcomed Bobby as excitedly as
Gina.
Once inside the house the two girls motioned for the boys to sit. They
told Tommy that he was free to go after he took them to the store. Tommy
knew that already, this afternoon had been meticulously planned. The girls
then explained to Bobby that they were in reality both boys. Jeri was like
Bobby his folks didn't know, and he only dressed on the weekends with
Gina. Gina on the other hand lived here with her mother who knew,
completely understood and as Bobby would later discover actually
encouraged her. They also explained that Gina's father, who was divorced
from Gina's mom, was spectacularly wealthy and had no idea what Gina spent
every month on her credit card, so they were going to transform
Bobby....their treat!!
Bobby protested, but the three of them wouldn't hear of it. They finally
dragged Bobby upstairs and got him into a pair of girl's shorts, a tank
top and sandals. They put some rudimentary make up on him and said, "We're
off to see the wizard!"
Ten minutes later they were in a small ladies boutique at the entrance to
the mall. Gina and Jeri knew the saleslady and introduced "Bobbi". The
next thing he knew he was in a dressing room with her being measured.
Bobbi was torn between excitement and complete fear with side trips to who
knew where. Maggie, the sales lady, did her best to calm Bobbi, he found
himself actually shaking. Gina and Jeri were at another store making
decisions on Bobbi's outfit for the dance.
Maggie wrote down the measurements. She then had Bobbi sit at the manicure
table. Gina and Jeri had left instructions for the color-red. They figured
Bobbi could be subtle later; this was a coming out party. Maggie struggled
with Bobbi's trembling hands, but finished her job. She then did his
toenails in the same bright color. Bobbie was practically transfixed by
the sight of his digits. He moved as if in a trance as Maggie moved him to
the chair where she would do his hair. It was a little long for a boy, but
too short to do much with, but Maggie did her best to give him a feminine
look. She then worked on his make up. She knew the "girls" would make her
work a little more dramatic later, but Bobbie would look great in the
mall.
Maggie finished as the girls erupted back into the store. They were so
excited to be doing this; they were unable to control themselves. They
burst into the back room, and immediately started gushing over Maggie's
work. After being critically reviewed by Gina and Jeri, Bobbi was finally
allowed to look at Maggie's work. He couldn't believe it. He really looked
like a teenage girl. He couldn't take his eyes from the mirror nor could
he stop smiling. Jeri stepped forward to put some clip-on earrings on
Bobbi; Gina paid and extravagantly tipped Maggie.
Now it was time to head into the mall. The girls grabbed their new girl
friend and pulled her out of the boutique into the crush of the mall.
Bobbi was afraid at first but walking between Gina and Jeri he gained
confidence with every step. The girls took him from store to store. Armed
with the right measurements Bobbi soon had a several sets of bras and
panties. He had four dresses and several skirts and tops. The most fun was
the shoe store. The shoe salesman was a teenage boy and while Bobbi was
reasonably well behaved, and Jeri was okay, Gina tormented the young man
unmercifully. Gina kept leaning forward showing off the fact that she was
not wearing a bra, and sitting in a very unlady like position while he was
putting shoes on her. In all the girls bought fourteen pairs of shoes.
Bobbi couldn't believe she now had four pair of her very own shoes....even
if she would have to leave them at Gina's.
While Gina once again paid, Jeri called Tommy to pick them up. The girls
carted their treasures through the mall, Gina flirting shamelessly with
the few teenage boys who crossed their path. Tommy was waiting for them
when they exited. He had a boy in the front seat with him. The girls knew
him, and with the exception of Bobbi everyone kissed everyone else. Tommy
introduced him to Bobbi, his name was Kevin, and he was obviously Tommy's
boyfriend. The girls piled their purchases into the trunk, and then all
three piled into the back seat. Bobbi was wedged into the middle of the
back seat. He was smiling. Jeri had his arm around him, and whispered in
Bobbi's ear that if he thought buying things was fun, wait until they
started trying things on.
Bobbi had no chance in keeping up with the multiple conversations in car.
Gina was so excited to have a new toy in Bobbi; Jeri wanted to talk about
their purchases; Kevin was asking the girls about the dance that night.
Tommy and Bobbi or was it Bobby, he/she was losing his/her grip. Once
again the girls were dropped off, and Tommy promised to be back at 8:00 to
pick them up. That left them just over two hours to get ready.
The next hour was a blur to Bobbi. Gina and Jeri had him in and out of all
the outfits they bought and all the possible combinations of them as well.
Finally, without much input from Bobbi they settled on a red low rider
mini skirt and a pink colored cami top that boldly showed off her navel;
and for shoes...three inch sandals. Jeri handed her a small red shoulder
purse to accent the look. Bobbi protested that the outfit was too skimpy,
but Gina laughed and said Bobbi should wait until (s)he saw the finished
product. With that they girls hustled him into the bathroom and began the
magical transformation. They even added a red choker to accentuate the
look. By the time they were finished with Bobbi and themselves...Jeri was
in a slinky metallic electric blue minidress and Gina was wearing a white
tube top and a green mini skirt...it was 8:00. Gina and Jeri took Bobbi
with their hands over her eyes to the full-length mirror and said what do
you think?
Bobbi was completely prepared to say that he couldn't go out dressed like
this. That is until he saw himself in the mirror. When the girls removed
their hands he almost fainted. He was astounded. He couldn't believe what
the girls had done. He actually got tears in his eyes. He hugged the girls
and was gushing thank you after thank you when the doorbell rang. It was
Tommy and Kevin.
Jeri ran down to let the two boys in to the house. She made them wait in
the foyer until Bobbi would come down the stairs. Gina came first and
announced the coming of Bobbi, "her greatest creation". Gina and Jeri made
trumpet sounds and Bobbi came out of the bedroom and down the stairs.
Kevin whistled loudly and Tommy burst into applause. Tommy couldn't
believe his next-door neighbor looked so wonderful. Bobbi tried to look
serious but he couldn't stop smiling. He hugged Tommy and thanked him for
bringing him to the city.
The five teens piled into Tommy's car and headed to the dance. It was
being held in a church gym not far from Gina's house. Tommy parked the car
in the lot and they headed in, the boys first and then the three girls.
Gina, Jeri and Bobbi made quite an entrance. They turned every head in the
place, even the chaperones.
Gina and Jeri were in charge and introduced Bobbi to everyone they knew,
which Bobbi surmised was everyone. Meanwhile Tommy was busy seeing all his
friends and Kevin was sticking close to his side. The DJ started playing
some songs the kids could dance to and Gina pulled Bobbi on to the dance
floor. Bobbi always considered himself an okay dancer...for a guy, but now
in three-inch heels and a mini skirt he never felt so self-conscious in
his life. But the longer he was out there the less and less self-conscious
he felt. Soon Bobbi had forgotten everything but that he was having a
wonderful time.
Finally, the DJ played a slow song and Bobbi and the girls were heading
off the dance floor, but Tommy stopped Bobbi, and asked her to dance.
Before Bobbi could say no, Tommy had her in his arms. Bobbi smiled up at
him and saw Tommy smiling down at him. Tommy said that he was happy Bobbi
was having fun and this was just the first of many weekends they could
spend in the city like this. Tommy also said that the plan for tonight was
for Tommy to stay at Kevin's house, and that Bobbi could stay with Gina
and Jeri. Tommy would pick Bobbi up at nine o'clock Sunday morning. That
was fine with Bobbi, but he asked if staying over was okay with Tommy's
mom? Tommy said his mom was okay with it since it would be late and that
Bobby was there with him. Tommy hugged Bobbi and kissed him on the cheek.
Then walked Bobbi, like the true gentleman Tommy was, back to the girls.
Bobbi danced with a group of girls for at least an hour. Some of the girls
were cross dressers and some were lesbians but they had one thing in
common, they were all having a great time. When the DJ played slow songs
the lesbians and the boys danced together. Bobbi's mind was like a sponge.
He prayed that he would remember every bit of this night. At about ten-
thirty the DJ played another slow song and Bobbi was heading off the dance
floor when he was gently tapped on the shoulder.
"Excuse me, would you like to dance?" Bobbi turned and saw a six-foot tall
very nervous young man desperately hoping Bobbi would say yes. In an
instant Bobbi remembered what it was like for her; rather him, to ask a
girl to dance and he/she smiled and said, "I'd love to".
Bobbi put her hand out and he tentatively took it. He led her to the dance
floor and gingerly took her hand, put his arm softly around her waist and
they started to dance. Before she could ask his name, Bobbi noticed he was
a very good dancer. She looked up to see his smiling face and, smiling
back at him, Bobbi asked his name.
He stumbled around for a second, and then said, "Jeff". Bobbi smiled again
and asked if that was his real name. Jeff looked shocked, but he said it
was. Bobbi couldn't believe how in control she was. Here she was the first
time dressed in public, and had this nice looking boy as nervous as anyone
she'd ever seen. She said, before he could ask, "My name is Bobbi, and
it's my real name too."
Jeff said he was going to be a senior at a high school not too far from
Bobbi's. Bobbi knew a lot of kids from there...cross-country runners,
basketball and baseball players, but he was reticent to ask Jeff if he
knew them. Bobbi merely said he was going to be a senior as well. When the
music stopped, Jeff asked Bobbi if he wanted to get a Coke. Bobbi again
said sure and they headed to the refreshment area.
Compared to the gym this part of the church was almost too quiet. Jeff
grabbed two cups of diet coke and brought them to the table that Bobbi had
selected. After a couple of minutes of silence, Bobbi asked Jeff if he
attended many of these dances. Jeff said no, this was his first event. He
added that he was really nervous about coming, but his mom suggested that
he attend. He then asked Bobbi, if she was a regular. Bobbi said no, this
was her first as well, and she came with a neighbor, her mom didn't know.
Pretty soon the two teens were talking and laughing about all matters of
things. First and most important to Bobbi, was Jeff asking Bobbi about
cross-dressing. Bobbi was glad Jeff knew that, but was secretly
disappointed he knew she was a guy (she really lost track of what he was
saying when she thought about the intermixing of pronouns). It turned out
that Jeff was very involved in theater and student council. No one at his
school knew he was gay. He had been battling his emotions for years.
Finally he went to his mom, and she got him some help. His mom had family
in the city and he was staying there tonight. Bobbi told him how he was
involved in sports and he had been battling his cross-dressing since
puberty. He then added that he didn't have the courage to tell his mom.
Then he added that he was having a great time tonight.
Jeff asked Bobbi if she'd like to dance again. Bobbi nodded and smiled.
Jeff took her hand and led her back to the gym in time for another slow
dance. Jeff took Bobbi into his arms with exponentially more confidence.
He held her tighter and moved with more confidence. Bobbi first reaction
to this new found confidence in Jeff to be a little scary, but soon she
relaxed and let him lead. Jeff moved gracefully and Bobbi found herself
with her head on his shoulder. She caught herself and as she tried to move
she felt Jeff's hand gently caress the back of her head. She laid her head
back on his shoulder and felt a kind of dreamy existence take her over.
She felt totally lost in the moment. This was the real life version of her
fantasies while dressed at home. She closed her eyes and without thinking
put her arms around Jeff's neck. He reciprocated by putting his arms
around her. Jeff softly stroked her hair, and as he did pulled her even
closer to him. Bobbie was suddenly very aware that Jeff was sporting a
hard-on. T heir dancing slowed to mere swaying to the music. Bobbi
dreamily looked up to see an equally enamored Jeff. When their eyes met he
kissed her.
Bobbi was stunned. She started to protest, but that only opened her mouth.
The next thing she knew Jeff's tongue shot was in there! She was all set
to pull her head away; this was too gay, when she found herself massaging
his tongue with hers. Jeff cradled her in his arms and Bobbi moaned. His
brain/her brain, Bobbi's brain had come close to short-circuiting. She had
to stop this but she was totally aroused. She wanted to take this further,
but knew, or thought she knew, she shouldn't. Bobbi broke off the kiss,
but she didn't back away from Jeff. Instead she buried her head in his
shoulder and held him even tighter.
When the song ended she looked up into Jeff's eyes, god they were a pretty
blue, and said, "Oh my God Jeff, we need to talk." With that she grabbed
his hand and pulled him back into the refreshment area. Bobbi found an
empty table and sat down. Jeff looked nervous, but Bobbi took his hand and
said, "Jeff, I really like you, and I really liked that kiss. But this is
moving a little fast for me. I am really confused right now." Then she
started to cry. Bobby never cried. But here she was crying. Jeff came over
to her side of the table and put his arm around her. He started to say he
was sorry for kissing her, but she put her finger on his lips. She said
she was glad he did, but she was so confused right now.
Jeff held Bobbi for a while, and then Bobbi looked up and kissed Jeff. No
tongue this time, but a kiss that held both passion and thanks. She then
took Jeff's hand again and they reentered the gym and danced some more.
During a break Jeff asked Bobbi for her telephone number and email
address. She gladly gave them to him and asked that he call her next week.
Jeff promised he would.
Soon it was last dance, and once again it was a slow song. Jeff and Bobbi
held each other tight. Jeff stroked Bobbi's neck and hair as she did the
same to him. When the song ended, they looked into each other's eyes and
once again kissed, this time Bobbi opened her mouth out of desire not
shock.
Jeff walked her over to Gina and Jeri; they were smiling broadly as the
two teens approached. Bobbi introduced Jeff, and just that fast they were
saying goodbye. Bobbi got into the back of Tommy's car with Gina and Jeri.
She wasn't prepared to talk, but Gina was peppering her with questions.
The girls had seen Bobbi and Jeff kiss. They also had seen them holding
hands in the cafeteria. For some reason Bobbi felt okay telling Gina and
Jeri, but she didn't want to talk about it in front of Tommy and Kevin.
Bobbi softly said she'd fill them in at Gina's. The girls understood, and
shifted their attention to Tommy and Kevin. The boys said they had a
blast, and as they pulled up in front of Gina's, Tommy said he'd pick
Bobbi up at 9:00 am.
The three girls piled out of the car and into Gina's house and straight up
to her bedroom. Gina and Jeri started to undress while Bobbi stood there
with a dumb look on her face. Finally, Jeri said it was bedtime and she
needed to get out of her clothes, makeup and into her nightie. Bobbi
nodded and reluctantly took off her clothes. The girls gave her a lesson
on makeup removal. Soon Bobbi was sitting on the floor in a royal blue
baby doll pajama set. She still felt wonderful, but knew her time for
dressing, at least for now, was coming to an end.
The three girls sat and talked for hours. Bobbi never felt so at ease in
her life. She told them about how Jeff was such a nice guy; how surprised
she was when he kissed her; and to the squeals of delight of Gina and Jeri
how wonderful it was. She also told them that she gave Jeff her telephone
number. She said she needed help, and wanted to know what she should do.
Gina and Jeri were good about relating their stories about first kisses
and first boyfriends and even first sexual experiences. Bobbi sat
transfixed. He knew all about what they were talking about but only in the
abstract. These two girls had done everything!
Bobbi thanked them for their help, and while he tried to stifle it, he
yawned. Gina jumped up and said it was time for bed. The girls got up and
Gina insisted to Bobbi that they all sleep in her bed. Soon enough Bobbi
knew why.
Once in bed Gina and Jeri attacked Bobbi. They had the pajamas off in a
shot. While Jeri was working from the bottom, sucking Bobbi's toes and
nipping his instep; Gina was kissing Bobbi passionately. Bobbi tried to
resist for a minute but soon caught up in the body worship the girls were
lavishing on his body. He was squirming and moaning. He never felt so
wonderful in his life. Gina moved down on Bobbi and was now sucking on his
nipples. Jeri had moved to the back of his knees. Bobbi was totally at
their mercy. He did make a half-hearted effort to try and do something for
the girls but they would have none of it. Gina told her to simply enjoy
it, and so she did. The two girls met at Bobbi's dick. They took turns
licking and sucking. Bobbi gasped when one of them put two fingers in her
butt. It felt foreign at first but wonderful within seconds.
Speaking of seconds within seconds of the dual assault on his manhood he
came. It was the most intense and fulfilling orgasm of his life. He felt
like he had cum all the liquid in his body. The girls didn't miss a drop.
They sucked him until he couldn't take it any more. Then they slithered up
him and both gave him tonguey and cummy kisses. At that moment Bobbi loved
them both. He hugged them and pulled them close to him. The girls then
turned their attention to each other and preceded to sixty-nine each other
until they came. Then the three sleepy girls all entwined in each other's
arms fell into blissful sleep.
Gina's alarm went off at 8:00 am. Bobbi knew he had to get up but the
girls wouldn't let him go until he got a good morning blowjob from Jeri.
While she was busy with Bobbi's dick Gina was making out with Bobbi. Bobbi
wanted to do something for her. He reached down into her panties and
started to stroke her dick. Gina moved closer so Bobbi could take care of
her, but Bobbi had made a momentous decision, he wanted to please Gina
like she pleased him. So he took both hands and pulled the cute blonde up
onto his chest. Gina looked down at him and asked if he was ready for
this. He nodded his head and pulled her forward. Bobbi opened his mouth
and Gina was in him. Bobbi sucked for all he was worth. He was worried
that he wasn't doing it right. Gina sensed it, and as she caressed him
soothingly told him he was doing great. Suddenly Gina grabbed Bobbi's head
and said, "Oh baby, I'm going to cum, do you want to take me in your
mouth?" Bobbi nodded and experienced his first taste of fresh cum.
Moments later, while Gina's dick was still being massaged in Bobbi's mouth
he came in Jeri's mouth. Bobbi was once again overcome with emotion. As
the girls repositioned themselves on either side of Bobbi, he fought back
tears. He was so happy. He wanted to quit school and live here with Gina
and Jeri. He wanted to find Jeff and have him hold him while they danced.
The last thing he wanted to do was to get dressed in his Bobby clothes and
go home. But that is just what he had to do. He kissed both girls and got
out of bed and headed for the shower. He turned to see Gina going down on
Jeri. My god, he thought those girls were insatiable
Bobbi emerged from the bathroom as Bobby. He was really sad. He thanked
the girls again and again. Gina said there was another dance in two weeks.
She said all of his stuff would be here waiting for him when he came back.
Then she added except for one outfit. Bobby looked at her quizzically.
Jeri handed her a bag, she said that there was an outfit in there for
Bobbi to wear next weekend when she went out with Jeff. Bobby started to
protest, but the girls just laughed and said, we have a bet....we are sure
you'll be going out next weekend. Bobbi started to protest again, but he
heard Tommy's horn blow out front.
The girls walked outside to see Tommy. They thanked him for giving them
Bobbi for the night. Tommy smiled broadly as Bobby blushed. In unison,
they said see you in two weeks. To waves and wistfulness Tommy backed out
of the driveway and headed towards the suburbs.
The two boys rode in silence for a while, and then Bobby started to thank
Tommy for a wonderful weekend. Tommy stopped him and said that he had a
great weekend too, and if it wasn't for Bobby he couldn't have gone to the
city. Bobby asked about the dance in two weeks, would Tommy be going?
Could they both go? Tommy said he had planned on it, and he smiled as he
added, I guess you had a good time. Bobby quietly said he had a great
time.
The boys pulled into Watson's driveway a little before 11:00 am. Mrs.
Watson came out to meet them along with Tommy's brother Pete. Mrs. Watson
wanted to know how they were and what they did. Tommy had a complete story
already made up. He talked about dinner and the movie and the friends and
where they stayed (one of Tommy's straight friends as Bobby found out
later). Pete was smiling as was Mrs. Watson. They felt like Bobby was
being a good influence on Tommy. Bobby thanked Tommy for driving and said
he looked forward to going into the city as nonchalantly as he could. He
also thanked Mrs. Watson for letting them go. He said it was fun and hoped
they could do it again.
Bobby headed to his house; he noticed his mom wasn't home yet. Once inside
he ran up the stairs to his room to see what the girls had packed for him.
He smiled. They had put the "little black dress" in the bag with sheer
black nylons, a garter belt, black bikini panties, a wispy black bra that
he didn't remember getting, breast forms, three inch black pumps and a
beautiful black choker that he knew he hadn't bought. Bobby carefully
carried the dress into his sister's room and hung it up among her things.
He took the undergarments, shoes and choker and carefully hid them with
his other stash.
Bobby headed back to his room to check his email. Like every teen he felt
he'd been out of touch for way too long...22 hours. He logged on and heard
the familiar sound of "you've got mail". He scrolled down to see if there
was anything good and halfway down the list was an email from Jeff. Bobby
clicked on the email.
Bobbi, thank you so much for such a great time last
night. I can't begin to tell you how wonderful you made
my first dance. I really hope you'll be at the next
dance, but I don't want to wait that long to see you
again. What is our chance of getting together this
weekend? I would love to take you out Friday or Saturday.
We could go out for dinner and dancing or dinner and a
movie. Please email me and let me know if I can call you
at home and we can work out the details. Thanks, Jeff
Bobby didn't know what to do. On one hand he was scared to death. He
couldn't start dating a guy. But the Bobbi part of him was so flattered.
Jeff had gotten in touch with him right away. Bobbi must have made a great
impression. While Bobby was thinking over what to do his fingers were
responding.
Jeff, I had a great time too. Here's my number, please
call so we can decide what to do. I am not sure which
night will work best for me, but I should know by late
Monday. Bobbi
Bobby hit send before he knew what he was doing. Oh God, I kind of said
I'd go out with him and signed it Bobbi. Bobby knew he was playing games
with himself. He wanted to go out with Jeff, and now he had to get his
mom's schedule for next week. He needed her to be out one night so he
could dress and go out with Jeff.
Bobby's mom got home around three o'clock. She was surprised to see Bobby
asleep in front of the television. He wasn't much of a TV watcher, but she
figured he had a good time with Tommy and was tired. She turned off the
television and let her son sleep. She woke him at 5:30 to let him know
that dinner was ready. Once he was awake she peppered him with questions
about the night in the city. Bobby found himself to be a good liar. He was
animated as he described events that never happened. Tommy had drilled him
on the car ride home, they wanted to be sure they had their stories
straight, just in case their mothers decided to compare notes, and Tommy
was sure his mom would want to verify his story.
Finally Bobby grilled his mom on her trip. She told him about how well
Grace is doing in school, that she may have a boy friend, but Grace
wouldn't tell her too much about him. Bobby asked, as nonchalantly as
possible what his mother's schedule would be the following week. She said
that she'd be working days Monday through Friday, and she would be off for
the weekend. Bobby tried to hide his disappointment. This meant no date
this weekend. Then his mom added that she would be going into the city
with two of her nurse friends. She laughed and said she'd be doing "a
Bobby" leaving Saturday and coming home Sunday morning. They both laughed.
Bobby was excited and scared. He rebooted his computer and with hands that
were shaking so violently he could barely type sent another message to
Jeff.
Jeff, Saturday works for me. You can pick me up at my
house, but you'll have to pull into the garage since it
would look odd for Bobbi to be leaving my house. Let me
know what time! I can't wait to see you again. Bobbi
About five minutes after Bobby sent the message, Jeff called him. They
talked for a while but the conversation was stilted and awkward. Bobby had
a hard time talking to Jeff about a "date". Bobby could sense the same in
Jeff. Nevertheless they worked out the details and each was committed to
going.
Bobby tried not to think about the date during the week. He did his
running and caddying as usual. The only times he thought about it was with
Tommy on Wednesday night. Tommy was excited for him, and admitted to being
a little jealous that Bobby was going out while he was sitting home. Bobby
suggested he call Bill and Jack and see what they were up to this weekend.
Tommy said he'd think about it. Gina and Jeri had sent emails with
suggestions and some very outlandish ideas. Plus, Bobby did get a couple
of emails from Jeff during the week and they were clever and funny. They
really helped Bobby from chickening out of the date.
Finally Saturday rolled around. Bobby was up earlier than normal to run
and to caddy and luckily got an early loop. This meant he'd be home in
plenty of time to get ready. Mike was in his loop and offered Bobby a ride
home. As they headed to Bobby's house Mike let Bobby know that Paul Taylor
was still seething at Bobby and was waiting to get him. Mike added that
he'd never seen Paul so angry and focused on anything. Bobby thanked him
for the information as he got out of Mike's car. Mike pulled away and
Bobby thought how Mike had stopped asking him if he wanted to go to any
parties. Paul really had a major influence on the social goings on in the
high school. Bobby shook his head and as he started for the house he saw
the garage door go up.
Bobby's mom was leaving for her trip into the city. She leaned out the
window of her car and kissed Bobby. She told him to have fun and then
added that he should behave. They waved to each other as she rolled down
the driveway and out onto the street.
Bobby tried to look nonchalant as he went into the house, but he was
smiling in spite of himself. The first thing he did was lock all the doors
and first floor windows. He didn't want another surprise while dressing.
Then he bounded up the stairs to begin his transformation. He had his
schedule plotted carefully in his mind. He started the bath first,
carefully adding scented oils to the running water. While the tub filled
he took out his razor, and got his makeup from his sister's room. Bobby
applied the shaving gel to his legs, and turned off the water. He
luxuriated in the tub, and when he was done he carefully cleaned it. He
didn't want to have the hair in the tub. Once he was satisfied with the
results, he dashed into his sister's room to begin dressing for his first
date. He was tempted to do something about the hard on that kept bouncing
up and down in the tub, but he wanted to stay as excited about this as he
could. It would have to wait. Bobby moved to his sister's vanity table to
apply nail polish and make-up.
He was going with the black dress, so his undergarments would be black as
well. He tucked his penis "down and under"..it was a painful process that
took a while. He put on the garter belt and carefully slid the sheer
nylons up his smooth legs. Bobby was becoming Bobbi in not just body but
mind. She smiled as she thought about dancing with Jeff again. Once she
had the nylons on and straightened, she slipped on the black lace bikini
panties.
Bobbi then went to work on her hair. She didn't want to wear a wig, so she
played around with it for almost an hour before she was happy with it. She
always called it her Lorrie Morgan look, but she had let her hair grow out
more than usual this summer, it was now kind of betwixt and between in
length. Finally she moved to her makeup. She made her eyes a little more
dramatic than the mixer in the city, and she made sure her lipstick
matched her nails. She was now totally Bobbi and she really wanted to
impress Jeff.
Jeff was to pick her up at 7:00, and it was now ten to seven. Bobbi
stepped into the black dress. It was strapless and very form fitting. He
inserted the breast forms into the dress and zipped it up. He finally
stepped into the almost 4 inch heels. Finally she added the choker. She
never felt dressed without one. She figured if he was going out somewhere
nice he was going to go all the way. Bobbi admired herself in the mirror.
She picked up her purse, added the necessary cosmetics and her id. She
carefully walked down stairs and hoped that Jeff would be on time. At two
minutes to seven Jeff called and said he was one minute away. Bobbi asked
him to pull into the garage, she was ready to go.
Jeff pulled into the driveway in a new Chrysler 300. He jumped out of the
car as Bobbi came from the house to the garage. Jeff was about to open the
door for Bobbi when he saw Bobbi. Jeff stopped dead in his tracks and his
mouth fell open. Jeff couldn't believe the vision in from of him. He
smiled and tried to regain his composure, Bobbi smiled and said "hi". She
walked to the car and without any plan to do it kissed him right on the
lips. Jeff recouped enough to kiss her back. Bobbi opened her mouth and
naughtily sucked his tongue. After a minute she broke off the kiss. She
looked up into his blue eyes and asked where they were going.
Jeff said that if she kissed him like that again they weren't going
anywhere; he would carry her into the house and make love to her all night
long. He then said there was a dance at his parent's club for the high
school seniors and college kids, a kind of end of summer bash, and they
were going there. Now it was Bobbi's turn to be stunned. He tried to say I
can't do that when Jeff put his arms around her and said, "Don't worry
about it, you pass wonderfully and no one will ever know."
Jeff was so convincing that before she knew it, Bobbi was in the car
heading to the country club dance. Jeff filled Bobbi in on what he had to
know to pull this off. Jeff then added that he didn't want to stay too
long and he didn't want to spend any time with anyone other than Bobbi.
Twenty minutes later Jeff gave the car to the valet and went around
helping Bobbi out of the passenger seat. Jeff took her hand and led her
into the club. There were about seventy couples, most of them older than
she and Jeff. They entered the dining room and Jeff picked up the table
assignment and whisked Bobbi to their assigned seats.
Bobbi found herself sitting with four other couples. They were all college
students and seemed to be okay. The girls professed amazement that Bobbi
was still in high school. Bobbi noticed one girl try to subtly keep her
date from staring at Bobbi. Jeff was a great date, he kept Bobbi in
conversations and he was very funny. It turned out that Jeff's family was
very very wealthy. He was right at home in this environment. Soon dinner
arrived and after dinner the band started. Since it was such a fancy place
the music tended to be less hip and much slower. This played right into
Bobbi and Jeff's desires. They staked out a corner of the dance floor and
hung on to one another during every slow song. The time flew by. During
the fast songs they talked about school, about college for next year,
about their families and Jeff and Bobbi found themselves becoming friends.
Then it was back to the dance floor for another slow song. Bobbi had her
arms around Jeff's neck and her head on his chest. She felt so feminine.
She loved this feeling and she didn't want it to end.
Jeff was smiling. He had a beautiful woman in his arms...and more than one
of his friends had told him so; but she was more than that, she met the
extra requirement that he needed, she was really a guy.
Jeff and Bobbi were pretty antisocial after dinner and at a little after
ten Jeff suggested that they leave. Bobbi agreed. She said she needed to
use the ladies room. She smiled as she entered what had once been
forbidden territory, she never even hesitated. She was Bobbi tonight, and
she knew that when they got back to her house, she wanted to ask him in.
She met two of the girls at from dinner table, and they talked for a few
minutes. The girls were all gushy over Bobbi and how wonderful she looked.
Bobbi thanked them and said she hoped to see them again soon. She, like
the other girls, fixed her lipstick, and exited.
Jeff had gotten the car by the time Bobbi exited the bathroom. He helped
her into the awaiting car, and they headed back to Bobbi's house. On the
way they talked about nothing and everything. The time passed, and as they
pulled into Bobbi's driveway she pulled out the garage door opener and
they cruised into the garage.
Jeff put the car in park and turned off the engine. Bobbi turned to him
and asked if he'd like to come in. Jeff smiled broadly and said
"absolutely".
Bobbi led him into the family room and asked if wanted anything to drink.
She went into the kitchen and retrieved two diet cokes. She returned to
the family room and sat onto the couch next to Jeff. Jeff took Bobbi into
his arms and stared deeply into her eyes. He gently caressed her face, and
then leaned forward and kissed her. Bobbi slowly lay back on the couch and
sighed as Jeff explored her mouth with his tongue. The two teens kissed
passionately for several minutes. Bobbi felt Jeff shift and he was now
lying on top of her. Jeff ran his left hand down Bobbi's leg and started
to caress her thigh through her nylons.
Bobbi moaned softly as they continued to kiss. Jeff was looking to move
their making out to the next level. He tried to reposition Bobbi so he
could unzip her dress, or at least get his hand under Bobbi's dress. Bobbi
knew this was a huge step, but she wanted more too. She wanted to be
treated like a woman and she was more than willing to let Jeff be the one
to treat her that way. She gently pushed Jeff up and broke their kiss. She
smiled at the horny teenaged boy and motioned for him to let her get up.
She stood over Jeff and slowly and she hoped seductively unzipped her
dress and let it fall to the floor. She stood now in here heels,
stockings, panties and bra. Jeff reached out and slowly slid her panties
down to her ankles. Bobbi couldn't keep her hard-on hidden any more. Her
dick sprang out in front of Jeff's face. Jeff gently kissed it, and then
stood up and removed his clothes. He moved in to kiss Bobbi and their
dicks rubbed against each other as they slowly and sensuously ground into
each other's pelvis.
Jeff asked Bobbi where his bedroom was. Bobbi hoarsely said upstairs.
Suddenly Bobbi was swept off of his feet and carried up the stairs. Bobbi
was doing his best to give Jeff a hickey as he climbed the stairs. Without
taking her lips off of Jeff Bobbi pointed to the left and they entered
Bobbi's room. Jeff gently laid Bobbi on the bed. Each teenager was
caressing and stroking the other. Bobbi was never so happy. Jeff had
Bobbi's bra off and was now sucking on his nipples. Jeff worked his way
down and was now kissing Bobbi's dick. Bobbi didn't know what to do, he
didn't want this to end, but she knew she was going to cum. She warned
Jeff, and he responded by speeding up. Bobbi came in torrents. She cried
out, she wasn't sure what she said but