Becoming A Shemale Sex Story

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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 did not 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 did not 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 dont 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.

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