My first

I can not recall my first time dressing, but I was very young. I do recall I would wait for my mom to leave for work or a date and I would run to her room and dress up in her clothes..it was so much fun. After a few years of dressing I became pretty good at it and wanted more than anything to be with someone who liked me looking this way. One evening she left and I put on her sexiest outfits. I put on black panties with a rhinestone in the middle. Black hose with black garters, a black leather skirt, black lacy bra, black patent leather heels, an anklet, a red satin blouse, and an Eva Gabor blonde wig. I put on my make up with cherry red lip stick and blue eye shadow. I put on some perfume and some jewelry. I painted my nails red. I must say I looked amazing and now much older than my actual age at the time. I grabbed her Marlboro light 100's and lit one up, I felt amazing and terribly horny. It was dusk and the MHP I lived in had a community court yard that had a basketball court and soda machines. I decided to venture out for the first time to the court yard to get a soda and smoke a cigarette. I was beyond nervous. I walked over to the machine, trying to walk softly, but my heels made so much noise....no turning back now. I got my soda and felt that someone was approaching me from behind....I told myself to stay calm. I moved away with my drink, lit my cigarette and tried to act cool. I noticed a man about 35 approach the machine and he said hello. I replied in my most feminine voice, but it came out crackled from being caught and hoping he did not know I was not a girl. He came over to me and said his name was Carl and he had just moved in for a bit until he completed a construction project in town. I told him I was visiting a friend and that my name was Michelle. He asked if I wanted to come by his place to listen to music and drink a couple beers, I told him yes that sounded fun. We got to his place and he put on the radio and offered me a beer. I had never had beer, but trying to appear mature told him yes.I drank several and when I got up to use the bathroom felt a bit dizzy. When I came back from the bathroom he said do you want to watch some movies. I said sure, to my surprise he put in a porn tape, I will never forget it had Candy Samples in it. I sat beside him trying to not show I had an erection. He noticed and said he thought I was a guy dressed like a girl and he liked that. He placed his hand on my thigh and rubbed my pantyhose gently. He moved my hand to his crotch and motioned it to rub his already hard cock. He then motioned my head towards his crotch as he undid his jeans. OMG it was a huge mushroomed headed cock that was pre-cumming and hard as a rock. I placed my mouth on the head and like the porn star in the movie started going up and down on his cock. My cock was throbbing against the soaked panties as I did this. He stopped me and said lets go back to the bedroom. I grabbed his hand as he led me to his bed. He said that he wanted to fuck me and I told him I was nervous as I had only fingered myself and used a brush some..I was a virgin. He said he would be extra gentle. He lubed up my ass with vasoline and then his dick. He told me to push back on his cock as it entered slowly. It was so painful, but I was enjoying being a woman for him so much I did not care. After a few minutes the pain went away and the pleasure began. He thrust his hard cock in me and I accepted it willingly. He wanted to fuck me missionary now he said so he could kiss me as he fucked my now loosened hole. I lay on my back and felt myself cum as he fucked and kissed me, it was amazing. He then told me he was cumming and I felt a warm pulsating load go deep in me. I was so happy. We layed together cuddled and I fell asleep. I woke up in a panic as it was now daytime outside and I had to get home, hoping no one was at home or in the park yet. I gathered my things, kissed him good bye and ran home. I made it home and did not see anyone, but an older neighbor lady that looked at me disapprovingly. I continued seeing him the rest of the summer. we met and had great sex about 3 times a week, he taught me so much and after this I never stopped dressing up to please men and enjoy being a sissy so much now.