Amy becomes a Boy
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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.