As a young catholic boy I always prayed I would have a women’s body. I would wear my sister’s clothes and masturbate in my bedroom. I have been a closet cross-dresser for a long time.
In my early twenties I rented my own apartment. I would buy from Fredericks of Hollywood catalogue for my outfits, bras, shoes, wigs, breast forms and thongs. I would also shave my body to be smooth like a female. I would hide my clothes and outfits so my girlfriend would not find them. She had her own apartment but has a key to my place. She worked as a Dj for a local radio station. She would do nights out for the station and dress for these nightclubs. She is slender like me.
While she was away I dressed up like a sissy. I put on her tight red dress which fit quite tight and I looked hot. I would take my dildo out and fuck my ass with it and masturbate. I have never been with another male nor have I been out in public dressed.
This day I did not hear her come in. With my face down in my pillow and ass up fucking myself, I hear her say “That dress looks better on you than me.” I turned around and there she was, standing in the bedroom doorway. I turned red. She said “don’t be embarrassed stand up let me see.” So I did she asked turn around let me see backside. Then she told me I needed make-up. Took out her cosmetic bag and went to work on my face.
I looked fantastic! She told me I pass for a female and told me that I can keep the dress, but I have to pay for it. She said lets go make some $. Went for a ride downtown, I didn’t ask a thing at this point still wondering what she was up to. We drove to the shady part of town and pulled over at a street corner. She told me to get out and walk this block from corner to corner till someone picked me up. What do I do then? I asked. She said “ask them If they want to party and earn your $40. She said she will follow the guy and pick me up when I came out.
Only 5 minutes later a black college student pulled up and rolled down his window. I said Do you want to party? He said yes get in. Drove to his college apartment and went in. He told me to go in his bedroom. I than heard the apartment door open and heard him talking to his roommate.
