I’m 28 now. I have been interested in women’s clothing as long as I can remember. I can
remember when I was around 7 my sister caught me trying on a pair of her panties that I stole
out of her room, I don’t think she ever told on me about that. As I grew I was always stealing
pantyhose, dresses, skirts and etc from mostly my family and my friends sisters. I wasn’t really
turned on by guys, but when I would slide those sexy pantyhose over my legs, I would find
myself fantasizing a friend of mine catching me in drag and us fucking. I have never told anyone
close to me that I cross-dress occasionally.
After I was out on my own, I started dressing up a lot and wanting to go out all
dressed up. So sometimes late at night I would get all dolled up and go drive around, mostly in
the country. Well one night I got all dressed up. I put on a little black dress, black stockings, 5
in heels, make up and a long blonde wig. So I got out in the country and was driving for a while
feeling really sexy and my cock was hard as a rock. I was driving down this country road that I
had never been on and BAM all of a sudden I heard my tire blow and my car pulled it’s self in
the ditch. I got the car out of the ditch but still had a flat. I remember my heart was beating so
fast and I was scared as shit being stuck out in the country dressed in drag. I hurried as fast as
I could to get my jack and spare out. But when I pulled my spare out I found that it was pretty
much flat. Oh fuck I said to myself pounding my hands on the trunk. Right then I seen
a truck turn from a side road really close to me and the trucks headlights shined right on me
standing there in my dress. The truck pulled up beside me and the driver rolled down the
passenger window and asked if everything is ok. I wanted to say yes but what was I going to
do. So I confessed and said hell no in as much of an feminine voice as I could. I explained the
situation and the guy said get in and that he would give me a ride home. So I got in and he said
his name was Rick. I said mine was Christine. Right when I said my name he looked at me closer
and was like are you a dude. I about started to cry and said yes. Rick said I really don’t know
how to respond to that. I felt so out of place, I told him how to get to my house. The ride was
quite but I could feel him looking at me constantly.
We pulled up at my house and I started to get out and told him thanks, he asked if I
had any beer. Yeah actually I do, do you want to drink a few I asked. He said that he would
like to. So we went in and I told him that I had to get out of these clothes cause I felt
awkward. Rick said don’t do that, I think you look sexy. I was shocked, didn’t know what to
say. So I sat down on my love seat and Rick sat right down beside me. We drank a few beers
just bullshitting about dumb stuff. All of sudden Rick put his hand on my thigh and started
rubbing it. I asked what he was doing and Rick replied I never been with a cross-dresser but I
want to fuck you badly. I told him that I hadn’t ever been fucked and would like him to be my
first.
He started to kiss me shoving his tongue in my mouth, still rubbing my leg. I started
rubbing on his cock through hi pants. I could feel his cock getting bigger and bigger. He said do
you want suck my cock, oh yea I replied. I undone his belt and unzipped his pants, pulled out
his cock. It was about 8 in. and thick. I knelt down in front of him and put my lips on the head of
his cock and started licking the head. I then started licking up and down his shaft, kissing and
licking all over his cock and balls. I went back up to the head and went down trying to engulf his
entire cock, I choked. I continued sucking his cock and he put his hand on my head and started
shoving his cock in my mouth. Gagging me over and over. Rick stood up and told me to take off
my dress. I took it off and he shoved his cock right back in my mouth. Standing over me he was
face fucking me bad, gagging me constantly, I could feel my spit dripping off my chin all over my
chest. Rick said you’re a good little bitch aren’t ya. Yes I replied anything you want baby. Rick
said good now stand up. He pulled my panties down and my cock flipped up, being so hard. He
pushed me towards the love seat putting me on all fours in the seat. He grabbed my lube out of
the table drawer and covered his cock and his fingers. He shoved two fingers in my ass. I
screamed and jumped. Rick was shoving his fingers in and out of me not being gentle. I want
your cock in me I told him. He put his cock up to my clitty and started slapping my clit with his
cock. He then stuck his head in and started slowly easing in. Rick got all the way in and pulled
out and shoved it in hard and started fucking me hard. He had a hold of my hips not letting
move away from him. His cock in felt so damn good, I could feel the blood going to head, I was
getting so hot. I looked down at my cock and could see some cum dripping off of it. Rick then
flipped me over putting my feet over his shoulders and leaning into me putting my knees above
my shoulders. God this feels so good I told him, I want you to cum in me baby, please cum in
me. Rick started slowing down but shoving it in hard, then all of a sudden he moaned real loud
and I could feel the warm shot of cum in me. He pulled out and backed up, I jumped up and
started licking all the cum off his cock while stroking my cock. It only took seconds before I
came.
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