My Early Years Part Three – Shemale Erotic Story
Sunday, April 8th, 2007I continued wearing pantyhose and meeting men for
a few months and one night my friend from work
told me that I should dress up as a girl and that
I would be knockout. We talked about it and he
helped me buy clothes, wigs and all the other
things I needed.
Part 2
I started looking through Transvestite magazines
and found a crossdresser newspaper that had the
address of clothing stores in the city and in
other cities. One of the stores was on Mission
street in the Castro District and I started
thinking about going there to buy clothes. I found
the store and drove around for a while trying to
make up my mind to go in or not. I finally made up
my mind and went in but I was very nervous
especially when the lady working there asked me if
I needed any help. I told her no and looked around
quickly and left.
I told my friend at work that I went to the store
but left without buying anything because I was
nervous. He asked if I wish now that I had bought
something, I said yes of course, and he mentioned
that the store was for crossdressers and I should
not be nervous. The lady at the store was very
nice so I decided to go back soon. I went back on
Friday and went in to look around again and saw
many nice shoes and clothes and stockings. The
same lady was there and she asked if I needed help
and I said I was just looking. She remembered me
and told me to relax and look around and to let
her know if I needed help so I felt a little
better. I found some very nice shoes that I liked
and she came over to help me find my size. She
came back with the black pumps and asked me if I
wanted to try them on but I said no. She then
asked me if I was new to this and when I said yes
she told me that I should try them on to make sure
they fit ok and I can walk in them so I agreed. I
sat down and she handed me a stocking to put on
but I told her I didn’t need one and took off my
shoe and sock. I was wearing pantyhose so I
slipped the shoe on and it felt great so I asked
if I could put the other on and she told I should
walk in them. I put them on and walked around and
they looked great. The lady told me to pull up my
pants and look at my legs in the mirror and I
thought they looked great and she agreed so I
bought them
I didn’t say anything to my friend because I
wanted to surprise him so I went over to his house
and hid the shoes under my rolled up jacket and
put them on the floor by the couch. When he went
to the kitchen for a soda I told him I was going
the restroom and picked up the shoes. I went in
and took off my pants and shirt and put my high
heels on. I went back out wearing the shoes and
pantyhose and he really liked the way I looked and
we were soon kissing and his hands were all over
me. His cock was very hard and I took his pants
off and sucked him for a while then I stood up and
bent over in front of him so he could see my legs
and ass and he tore a big hole in my pantyhose and
was fucking me real hard and for a long time.
After we finished I told him about all the nice
clothes I saw in the store and he suggested I
start buying some so I could dress up for him. He
even gave me money to buy a sexy dress and told me
he would send his wife to visit her sister back
east so we could spend the whole weekend together
as man and wife. I loved hearing him say that and
his cock got hard again so I laid on the bed
between his legs and sucked him slowly for a long
time before he came in my mouth.
I went shopping a week later and bought a dress
and garter belt with stockings. I had never worn
them so the lady at the store helped me put them
on. I can remember how excited I was to be in the
dressing room wearing the stockings over my
pantyhose(I don’t like panties) with the high
heels she let me use. I bought a black dress that
was a little above my knee but she suggested I
have it hemmed shorter and she would send it out
if I wanted. I really liked they way it looked
real short so I had her send it out for me. During
this time my friends wife became very sick and
they ended up moving back east so he never got to
see me dressed as a girl.
Part 3
I continued buying clothes and wearing them when I
was alone at home but I would hide them in the top
of my closet so no one would find them. My
favorite thing to do was to dress up in my
pantyhose, garter belt and hose and heels while I
drove around the city. It was very exciting to
have men in trucks pull up next to me and see my
legs. One night I got dressed and took my shoes
with me (in a gym bag) to drive around and I went
to a part of Oakland where there are many big rig
trucks because the drivers could easily see me all
dressed up in the car. I drove around and decided
to pull my pants off and put on my heels. This
always gets me excited so I drove around and let a
few guys look at me then I headed down a quiet
street because I wanted to walk around outside my
car. I parked and looked around before I got out
and walked down the street. This was great and I
felt so sexy in my garter, hose and heels so I did
this for a while until I saw a truck a few blocks
away so I got back in my car and left. I drove
around some more and I had one truck driver pull
up next to me and he followed me all over. I
didn’t know if he was mad or liked me so I pulled
away and I could see him flashing his lights at me
and waving for me to come back. I was horny so I
turned around and drove back by his truck and he
stuck his head out his window to say hello and
tell me how nice I looked. I thanked him and he
wanted to talk to me so I said ok and parked
across the street from his truck. He came over and
was telling me how much he liked my outfit and
seemed like a nice guy so I was ok when he started
feeling my thighs and cock. We kissed and I got
out of my car and we both kissed and I felt his
cock through his pants. He told me he wanted to
take me into his truck and have sex with me so I
reached in my car and got a pack of rubbers and he
was rubbing his cock on my ass while I did this.
We went in his truck and he had a small room with
a bed in it so I helped him take his clothes off
and I put the rubber on his hard cock. We sucked
each other and he then turned me over on my knees
and tore my pantyhose so his cock would go into my
ass. It was very long and felt great going in and
out. He was real rough with me and fucked me real
hard but I liked it a lot. He fucked me for a long
time until he said he was cumming so I quickly
turned around and pulled the rubber off. I jacked
him off until he shot his cum on my chest and legs
while I sat in front of him. We both spread his
cum all over my body and I was so hard that he
sucked me and let me cum in his mouth. After we
finished he gave me a rag and I cleaned up and
left. This was the first of many hot times with
truck drivers and the good thing is that they are
the nicest guys I have ever met and the guys with
the biggest cum loads.
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