Date: Thu, 25 Apr 2013 01:18:10 -0500
From: jon gaynokla <gaynokla@gmail.com>
Subject: chris likes to dress up m/t, t/b
chris likes to dress up
by Jon,
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little slow but picks up later. My other stories are at the bottom of the
story... all of them are different styles, so enjoy them. You can e-mail
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My next door neighbors Betty and Steve are always at my house, along with
their teenage son Chris. They come over for cookouts, parties, and to just
hang out and talk. They even asked to use my garage to hide a new 2013
Toyota Prius hybrid that they bought Chris for his 16th birthday. During
his party, they told him they were running out of ice and to run to my
house for more. I always keep some in my garage freezer just for parties
or other emergencies. He complained the entire time he was leaving the
party, saying that the birthday boy shouldn't be doing any work. We all
laughed as he left knowing full well that he would find the car wrapped
with a large red ribbon and "Happy Birthday Chris" written on it.
Not even three minutes later, we all heard a loud scream. Then my garage
door opened, we heard a car start up and out Chris came in his new car. He
pulled into his driveway and all his friends and family ganged around it to
help celibrate his excitement. I had never seen him so happy.
As the party wound down, Chris told his parents that he was going to take
Amy, his girlfriend for a ride. I figured they would ride around a little
bit and then head to the lake to make out. I am not too sure how far they
have been but I would guess the way Amy would sometimes run her hand across
Chris's upper, upper thigh that she was familar with what his pants hid
inside them. She was already 16, only about 5'3", maybe 100lbs of very
beautiful girl. She had long straight blonde hair, small but very firm
breasts that she liked to show off with very tight, low rise shirts. She
had a great head on her shoulders and liked to crack jokes, often at
Chris's expense. She adored Chris and was liked by all.
Chris was very similar and close in size to Amy. He stood maybe an inch
taller than Amy, his hair was brown that he always wore in a long ponytail,
and he probably even weighed about the same weight. His body was toned and
slim, he was into running so he was not as muscled as most teenagers. He
was just as smart as Amy and took her pranks and jokes in stride. He was
always touching Amy and would often give her quick little kisses. Over
all, they were a very cute couple.
The next week Steve found out that his job was sending him to Africa to
help open a new medical clinic and he would be gone a month. Betty was sad
that he would be gone so long till I suggested that she accompiny Steve and
take a well deserved vacation. I told her that since Chris was now old
enough to drive, he would be fine by himself and that I would be here if he
needed anything. I know what you are thinking dear reader and no, I was
not interested in getting Chris alone so I could have my way with him.
Maybe if he was gay, but he wasn't and he seemed to love Amy, so all I
would have to do was make sure she went home at the right hour. Seemed
easy enough.
Steve and Betty left on schedule and Chris was in and out of his house the
first week they were gone. He told me one day that he was helping Amy
babysit. She babysat for a few families, most had two, sometimes three
kids ranging in age up to a few years younger than her but they didn't have
the ability to take care of thier younger siblings. I guessed that meant
that Chris and Amy got to makeout after the kids went to bed and even got
paid for it.
Then on tuesday evening Chris came by for some advise. He would sometimes
ask me for my perspective on things that he didn't feel comfortable asking
his dad about, although it had mostly stopped as he got older but since his
dad was out of the country, I figured he just needed to talk. He looked a
little distracted and seemed to kind of have a hard time focusing, so I
told him to relax and spit it out.
"Well, you know I have been helping Amy babysit and the other night we were
at the Johnson's house watching Cindy and Bobby. We were having a good
time and Cindy wanted to play dress up," he started, "she wanted all of us
to play although Bobby refused. She dressed me in her mom's clothes and
then told me that since I was already dressed that I would have to take my
clothes off because they were causing problems with her mom's clothes. So
I went into the bathroom and removed my pants and shirt, putting the dress
Cindy gave me back on. Then I returned and she insisted that I needed
makeup. I let her put makeup on me and then she took my ponytail down
saying that all I needed now was shoes. She found a pair that matched the
dress and I put them on." Then he just blanked out for a momment.
"Ok," I said, "is that all or is there more? Playing dress up with Cindy
is normal and she probably had a great time with you."
"Oh, she did. She was very happy and told me how good I looked, so I
turned and looked into a mirror that was on the wall. I was stunned. I
wasn't sure who I was looking at... I mean, I looked like a girl. I stared
at myself for a few minutes before Amy told everyone it was time for bed.
I turned to help clean up and saw that Bobby was staring at me. I told him
to go get ready for bed and we would say goodnight as soon as we had things
cleaned up. I then went into the bathroom and changed back into my clothes
and washed the makeup off my face."
"Ok, I still don't hear anything sounding like something you need help
with. It sounds like you are great with kids." I told him.
He looked a little shaken as if thinking of something horrible but then
started back with his story. "After we said goodnight to the kids, we went
down to the sofa and started to make out. Amy was really hot and all over
me. I pushed her off me and asked why she was trying to rape me. She just
laughed and told me she was all hot and bothered because of the way I
looked in women's clothes. I just stared at her till she laughed again and
asked if I had noticed Bobby afterwards. I told her I had seen him staring
at me but that was all. Then she went into great detail telling me how
beautiful I am as a woman and how sexy. She noticed Bobby staring at me
with lust while he was rubbing his crotch. I told her she must have been
mistaken but she assured she wasn't. Bobby must be going through puberty
or near it cause she said he was hard and lusted after me. Then she told
me that the thought of Bobby having his way with me as a woman was what
really had her juices flowing. Then she stripped me and was all over me.
I felt used. I mean, I love her and I love sex but I didn't feel she was
having sex with me, for me... if that makes since."
"I totally understand what you are trying to say. You felt she was living
in a fantasy instead of being in the present with you." I looked at him
watching his expression before going on, "I understand what you are going
through but everyone gets lost in fantasies at times, it's part of life."
"But you don't understand.." he stammered, "I got lost in it as well. I
WAS sexy in that dress and hell, I wanted to fuck me. Then I realised that
I wanted more than that... I wanted to feel what it was like... to umm.. to
be the woman in that dress being touched and fucked by a horny young boy.
I started wondering what it would have been like if Booby had come on to me
and if I had let him... do things... to me. Since that night, I have been
jacking off to that thought a lot. Hell, even Amy knows I was thinking
about it... that night while she was on top of me, riding me, she kept
talking all sexy like about how hot it would be to see Bobby or other
little boys loose their cherries in my ass as I was dressed in women's
clothes and how hot it would be to be fucked by me dressed up... I mean I
am straight. Right? I don't know. I, I want you to help me... if you
would that is... I want to dress up and feel what it feels like to be a
woman."
Then he just looked at me like if I said no, his world would end. "What
would you like to do exactly?" I asked seeing his face light up as big as
it did as when he got his car.
"I want to buy some clothes but I don't want to do it alone. Would you go
with me and help me buy some, for someone else that is, if anyone asks.
And some underclothes as well."
"Of course I will." I said.
"I will need makeup and shoes and ummm... then when I am ready... Would
ummm would you, you know... fuck me?"
Previous stories: the dates are where I found them in the archives.
gay:adult/youth: doing the wash -october 11, 2012
being used by zach -january 23, 2013
liquor store -march 15, 2013
bike brothers -march 31, 2013
gay:incest: dad's son dave -october 14, 2012
bisexual:incest: losing it -march 3, 2013
gay:adult/youth i dream of billy -april 2, 2013