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