A Jock Strap for Jenny

by Kozmik Alaska

Jenny had been planning her adventure for months. It was the last week of
summer vacation. Jenny had turned 18 that August and was ready to begin her
senior year in High School.

She knew that turning 18 was a big deal, carrying with it a lot of
responsibility. So Jenny wasn't surprised that when her parents decided to go
to Niagara Falls for a second honeymoon, the left her to mind the house.

Jenny received a lot of presents for 18th birthday, but the most special
present she got was her parents telling her that she could get her hair cut,
short. Real short. She was to get it cut this very special weekend. You see,
Jenny had plans for the weekend, and they involved a boy. Not just any boy,
but a real soul mate. His name was Rick, and well, you'll see.

Around lunchtime on Friday, Jenny's mom and dad packed their suitcases into
the car. Jenny's mom, always the worrywart, must have spent an hour reminding
Jenny to "not let anyone in the house, leave the porch light on, don't talk
to strangers, and on and on and on. Jenny's mind went on autopilot as she
replied "yes, mom" for the twentieth time. Jenny stood in the living room as
her parents were getting ready to leave.

"You have the phone number of our motel, Jenny?" Jenny's mom asked.

"Yes, mom." Jenny answered.

"Well, so long then"

"Yes, mom, er, bye mom. Love you. Bye dad"

Jenny's mom gave her a confused look. "Jenny, wake up! You're day dreaming
again! Sometimes I wonder where your head is, girl"

"Sorry mom, just excited about getting my hair cut" Jenny gave her mom a
good-bye kiss. "Have a great time!"

Soon the old Chevy station wagon made it's way down Bay Street. Jenny waved
as it disappeared around the corner. She walked to the edge of the sidewalk
and made sure that it was well out of sight. Breathing a great sigh of relief,
she went back in the house, and locked the front door behind her. Cautiously
she went up the stairs to her bedroom.

Jenny walked over to the window in her bedroom and checked once again to make
sure that her parents where really gone. She then pulled the blinds shut.
Jenny opened the drawer to her desk and took out a screwdriver. Carefully she
removed the back of the left speaker of her stereo system. Out tumbled several
pairs of jeans, a sweatshirt, some boy's shirts, and a pair of boy's running
shoes.  Jenny set the clothes to one side and replaced the speaker's back.
Next she moved to the back of the right speaker of her stereo. Out tumbled
several pair of boy's jockey shorts, several undershirts, some athletic socks,
a can of shaving cream and a razor. After replacing the back of the right
speaker,
Jenny stacked her cache of goodies on her bed.

Jenny stripped off her clothes and tossed them, balled up, into the corner.
She hadn't shaved her legs or underarms in a while and stood there admiring
the dark fuzz that was growing on them. Picking up the jockey shorts she
smiled a mischievous grin. She handled them as if they where a king's robes.
Once again, she sighed, but this was a sigh of pleasure. Bending down she
slipped the jockey shorts up her legs. She then adjusted them on her waist.
Next Jenny stuffed a sock down the front of the jockey shorts to simulate a
healthy male bulge between her legs. Smiling she rubbed the bulge with her
hand.

Next Jenny took an ace bandage out of her top drawer. She wound it around her
chest in order to flatten her already small breasts. Jenny remembered the
taunting she used to take from some of the girls in gym class because she
wasn't well endowed. That was just fine with her, though. Next Jenny pulled
an undershirt over her head and tugged it down over her now flat chest.

Picking up the can of shaving cream and the razor she went down the hall way
to the bathroom. She paused for a moment to admire herself in the full-length
mirror on the bathroom door. Aside from the slightly feminine hairstyle,
Jenny looked like any other teenage boy getting ready to shave. 

She stepped up to the sink and wet her face with warm water. After that was
done she shook the can of shaving cream and spayed some of its contents into
her hand. Jenny spread the foam on her cheeks and neck and was sure to get
some under her nose. Finally she wet her razor and began to shave her face.
She smiled and hummed a happy tune as she did this, her boyish duty.

With her face now shaved, Jenny splashed some of her dad's Old Spice
after-shave on her cheeks. The cologne stung a bit, but felt refreshing.
Now she was ready to complete her transformation.

Back in her bedroom Jenny put on a pair of athletic socks. She then put on a
boy's shirt. Funny, she thought, how boy's shirts buttoned opposite from
girl's shirts. Her mind drifted back to the first time she tried on a boy's
shirt. How odd it felt to button it on the other side. Now she was quite used
to it. Next she put on her boy's jeans and running shoes. Jenny had now
become Rick.

Although Jenny had dressed in boy's clothes on many other occasions, today
was to be a day of firsts. She remembered the first time she wore jockey
shorts. Now she had a habit of wearing boy's underwear quite often. She
chuckled as she thought about what people at school would think if they would
sneak a peek up her denim skirt and saw the "Y" front fly of her white boy's
briefs. Today was to be special. Today, for the first time, Jenny was going to
go out to the mall as a boy. Today Jenny was going to get a boy's haircut.
And today, Jenny was going to buy her first jock strap.

Jenny stuffed a boy's wallet in the back pocket of her jeans, before leaving
the house and walking to the bus stop. Nervously she waited for the 1-F Mall
Express bus to arrive. What if someone recognised her? Damn where was that
bus. The minutes dragged by. Finally the bus arrived. Climbing aboard she
grabbed a seat near the door.

At the next stop a lady got on. She asked Jenny, "May I sit here, young man."
Jenny smiled and answered in her deepest voice, " Yes, Ma"am."

Inside, she was jumping for joy. She passed. She was now a boy!

Once at the mall Jenny headed straight the barbershop. Inside she sat waiting
her turn. She picked up a copy of Boy's Life magazine and sat engrossed in an
adventure story, until she heard a man saying, "You're next, fella."

"Oh, Thank you." Jenny replied.

Jenny climbed in the barber chair and the barber wrapped a cloth around her.
"What'll it be son?" he asked.

"Something short for school, but still trendy" Jenny replied. She knew that
she couldn"t get too carried away. Soon the whir of the clippers filled the
air as the barber trimmed Jenny's hair. She sat there filled with glee as she
felt the clippers on the back of her neck, and then trim round her ears. Then
the barber took out his comb and parted her hair in a very boyish style. When
Jenny looked in the mirror she couldn"t believe her eyes. A handsome boy looked
back at her.

She paid the barber and then decided to head off for her next big adventure.
Stopping by a big department store, she bought some jeans and few pair of
Calvin Klein jockey shorts. She could hardly wait to try them on and pose
like the guy on the box.

As she was making her way to the sporting goods store, nature came calling.
It was to be another first for Jenny as she entered the men's restroom. She
wished that no one was around so that she could have tried standing to pee,
but settled for sitting. After she finished she stepped out of the stall,
and almost bumped into a guy about her age coming into the restroom.

"Excuse me, " he said.

"Sorry" said Jenny, her heart beating wildly.

She nervously made her way back out into the mall. "Phew" she thought,
"That was close".

The sporting goods store was one level up so Jenny headed to the escalator.
When she got to the store, the excitement of buying her first jockstrap had
replaced the anxiety of the earlier moments. Confidently she strode to the
back of the store.

"Wow!" She though. "This is like heaven. Bike brand jock straps and they're
on sale."

"May I help you young man". An attentive sales clerk stood behind Jenny.

"Ah, er, yes. I need to buy a jock strap, and I'm not sure what size to get"
Jenny said."

The clerk asked, "Is this for you?"

Jenny replied, "Of course!"

The clerk then got out a measuring tape and measured Jenny's waist. "32
inches." He said, "That"ll be a medium."

"Well what about the.... ah...you know .....will it fit in the...ah..pouch."
Jenny asked nervously.

The clerk got a puzzled expression on his face and laughed, "Nobody ever
asked me that before! Unless you're over endowed or a girl, this should fit
just fine. And I don"t think you're either." the clerk said as he handed her
a jock strap.

Jenny took the package into her sweaty hands. "Ah, well I get no complaints
about
it, and, hee, hee, I'm not a girl. Thanks then."

Jenny pulled some cash out of the front pocket of jer jeans and paid for the
jockstrap then headed out of the mall. She got on the next bus heading home.
The cool evening air felt great as it blew through her new boy's haircut.

Once safely back home she sprinted up the stairs to her bedroom. She
hurriedly took off her shirt and pants. Standing there in just her jockey
shorts and undershirt she opened the box containing the jock strap. She took
off her jockey shorts and slid the jock strap up to her waist. Jenny adjusted
the straps in back, pulling them down over the cheeks of her rear. She
adjusted the pouch in front. Her mind was swimming and her heart was pounding
like a trip hammer. Boom Boom Boom.

Her hand slid down to the rough fabric of the jockstrap and she began to
massage her clitoris, or girl-penis as she called it. First she massaged it
quickly, and then slowed down, Her girl-penis stood proudly erect in the
jock. Jenny looked inside the jock. It was as big as it had ever gotten.

Now Jenny massaged it slowly and soon moans of ecstasy filled her bedroom.
She spied herself in the mirror, with her short hair cut, unshaven legs,
wearing a jock strap, standing there looking very much like a boy jacking off.
Soon she collapsed on her bed.

That night Jenny slept in just her new Calvin Klein briefs and a T-shirt. She
dreamed about the fun that she would have wearing her jockstrap to school or
under her swimsuit.

The next morning she awoke to sound of the doorbell. Still half a sleep she
went to the front door. Opening the door she saw it was the young man from the
mall that she had bumped into in the restroom.

"Hi" he said. He looked at the picture on the driver license in the wallet,
and at Jenny, standing there in her jockey shorts and T-shirt.

"Shit" Jenny thought, "My wallet!"

"I"m looking for Jenny Spencer. I found this wallet in the men's restroom"
the young man said.

"Are you Jenny Spencer?"

"Ah, yes, er no, ah you found my wallet!"

"So this IS your wallet, then?" the young man asked.

"Yes", Jenny's said taking it, "Thanks, bye!"

Jenny hurriedly closed the front door. Her heart was pounding. The doorbell
rang again. It was that boy.

"I'm a bit confused, If that's your wallet, then you must be Jenny Spencer,
the girl in the picture on the driver's license. Then why are you wearing
boy's underwear."

Jenny trembled.

"Its okay" the young man said. "I'm kinda like you, and I think I kinda like
you. Don't be afraid."

"Huh?" Jenny asked. Stepping inside the house, The young guy closed the front
door behind him. Then he turned his back to Jenny and began undoing his jeans.
Jenny noticed that he was wearing Chic girl's jeans, Then he dropped his jeans
and turned around. He was wearing a cute pair of pink lace Victoria's Secret
bikini panties.

"You see", He said, "I like to wear girl's underwear, and from what I see,
you're a girl who likes to wear boy's underwear. I think we're perfect for
each other"

And as the school year went by, they found out that this was very true.