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Amy becomes a Boy
By Kozmik Alaska
Amy had a very loving caring and open relationship her friend Tom. Tom
was 19 he was already working with a travel agency. There were two
reasons why he liked this job, the first was that it allowed him to go
on trips for ad promotions, the other reason was that it paid well
enough for him to afford his own condo. Amy liked his job for three
reasons, the first two were identical to Tom's, but Amy's third reason
is where this story gets interesting...
Tom owned an award winning Persian cat named Elizabeth, and when Tom
traveled, he would ask Amy to stay at his place and take care of
Elizabeth. Amy enjoyed staying with the cat because it also provided
her with the opportunity to try on Tom's clothes. Her friend is always
buying new things, and because Amy was about his size, the clothes fit
very well!
On one particular Saturday, Tom called and asked her to stay for the
week. She showed up around 10 O'clock in the morning, and he was out
the door by 10:30.
Let me tell you a little more about Amy and her friend Tom. Amy was
very good looking with short sandy blonde California hair, she was
about 5'6" and weighed in at about 130 pounds. Oh yes, don't let me
forget the best parts, Amy has always been teased for two things.
First, she has a baritone voice almost masculine, and second, an almost
masculine body, nothing obvious, just strong features. If her friend
wasn't 3 years older than her, they could be considered twins. The
only obvious difference, (besides of course the male/female one) was
that Tom had a very manly bulge between his legs, his 8 inch cock.
It didn't take Amy long before she had taken a shower and headed for
Tom's closet. By 11:30 she had already put on a jock strap, Tom's
white jockey shorts and one of his muscle shirts and was in the process
of shaving the peach fuzz off her face when she heard a car drive up.
She panicked and put her female clothes on over the masculine underwear
thinking it was just somebody dropping by. Just about the time she was
10 feet from the door she swallowed in fear when Tom opened the door,
and said that the trip had been canceled, something about a problem at
the office. He had an interesting gleam in his eye when he suggested
that she spend the weekend with him anyway. He then left for the
agency, promising to return by 6. After he left she went into his room
and began removing her clothes when she caught herself in the mirror,
she could make out the lines the jock strap made in her jeans, she
could even see a little bit of the white elastic waistband of her
jockey shorts sticking out around the waistband of her jeans. She
could only hope that he hadn't noticed.
He came home as promised, right on time. She waited in the front room
while he showered and changed his clothes, then they went out to dinner
and discussed the problems at his job. When they returned to his
place, he suggested, again, that she spend the weekend with him, and
that she could sleep in the other bedroom. The second bedroom was
always ready for guests, so she decided to stay. They said their
goodnights and Amy went to her bedroom and began undressing. As she
pulled back the blanket and moved the pillow, she noticed some fabric
under the pillow. She pulled on it and found it to be a jock strap and
tee-shirt. The jock was white Bike brand jockstrap and the tee shirt
had the words 100% Stud printed on it. She noticed that they appeared
to be brand new but figured that they were Tom's. She carefully walked
to the door and peeked down the hall to Tom's room and saw that the
door was closed and the crack under it was dark. She turned out the
light, closed the door and went back to the bed. She pulled the
jockstrap up her legs and the tee-shirt over her head. As she adjusted
the jockstrap into place, she imagine that she could feel a cock and
balls between her legs. She was more excited than she had ever been
before, probably because this was going to be the very first time that
she would be in masculine attire while someone else was around.
She was just about asleep when she felt the door open and then the
light went on. In walked Tom, he was wearing nothing but his jockey
shorts. He was a real hunk. She asked his what he wanted (the blanket
was covering her boy's underwear). He said that he wanted to talk
about her wearing his clothes and even wearing his jockstrap right
then! She feigned ignorance until he pointed out the fact that she
hadn't shaved her underarms. Amy was about to have convulsions from
fear, when he started talking about how he had always suspected her
desires and that was the reason for having her stay over so often. He
always had a little bit of doubt, but that was thrown out when he could
see the jockstrap showing through her jeans. That night, while she
thought he was getting ready for dinner, he went into the guest room
and hid the jock under the pillow. He said that it was OK, and he did
not mind her doing this. He even said that he liked it. He also said
that she could come over anytime and he would help her if she wanted
him to. Amy was in shock, she just could not believe her eyes and
ears!!
Amy sat up in the bed and let the blanket fall away from her. Tom said
"You really do look handsome in that jock strap but tomorrow let's get
you a bulge down there. I'll get you a strap on dildo with balls to
wear." Amy was just about to the point of tears when they reached out
to each other and hugged. Amy could feel his flat muscular chest
against her small breasts, and his cock against her legs. It felt so
different than it ever had before. He must have noticed because he
turned his head and brought his lips to her and kissed her. He
released her and said, "I remember putting the jockstrap there, but I
did not put any jockey shorts under your pillow. Are you wearing
jockey shorts now?". "NO" Amy responded. He then stood up, pulling
Amy's hand with his. "Well, you can't be sleeping in just a jockstrap
without any jockey shorts. Let's go into my room and get you some."
Amy was glowing with excitement as she stood up to follow his. Tom
looked down at Amy's waist and whispered into her ear, "would you like
me to take care of that?" Amy looked down at the moist spot on her jock
and meekly responded with "OK". He began by bringing his hand up her
arm and then caressing her chest. He then lowered herself down to his
knees. He softly touched her pussy with his hands through the cotton
material. After a minute of this Amy sat back down on the bed. He
pushed aside the jock, baring her pussy, and began to suck on Amy's
hard clit as he caressed her unshaven legs. As he began to make love
to Amy with his mouth, Amy, in an obviously heightened excitement, came
with a force she had never experienced before. When he had finished he
climbed on top of her and kissed her. Amy could taste her own juices,
and she liked it. After a few relaxing moments, Tom pulled Amy up to
her feet, and said "Come on Amy, let's go get you some jockey shorts
for you to sleep in!".
They playfully ran into Tom's room and Amy went straight for the drawer
that contained all of his underwear. She selected a real masculine
pair of boy's underwear that would show off the bulge made by her jock
strap. Tom said "You have good taste Amy. I always feel really horny
when I wear that pair." Tom continued, "Have you thought of a name for
yourself when you are dressed? We can't go on calling you Amy, when
you are dressed so masculine!" Amy said "I haven't really given it much
thought".
"What would you think about the name Jimmy. I will bet anything you
look like a Jimmy when you strut out looking like a stud!" Tom asked.
"I like that name." Amy said.
Tom then said "Jimmy, why don't you come to bed. We can get some rest
and not be to tired for a big day tomorrow."
"You want ME to sleep with YOU, tonight?"
"I don't see why friends can't sleep in the same bed, Jimmy" Tom said.
Tom turned out the light as Jimmy climbed into bed next to his very
best friend in the world.
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