I made out with a trans person and had sex with another...

I do not think that I have ever had any kind of love life. To be honest I am not even sure if I have ever had a girlfriend or ever even been in a relationship but I can tell you I have had sex with women before and it was not that good. I always desired something passionate with a woman but the few women I have been with have always been nothing. I reflect on these women and I feel shame because I spent most of my interaction with them chasing them or feeling less then them. Sometimes I go out and I hope to meet someone and nothing ever happens....

One night I was walking home drunk and this woman was with a group of guys and they were walking a head of me she looked back at me several times and she slowed down so that she could talk to me. I do not think I am really a sexually aggressive person I would never assult anyone or hurt a woman but I am ashamed to say it has been years since a woman has touched me or even looked at me. She looked at me for a moment really looked at me and I grabbed her and held her against the side of the building and started making out with her... She kissed me back and was really into it I had a moment of clarity and thought to myself what the fuck am I doing.

After that she just looked at me and walked off. I was in shock from myself and by her because SHE WAS INTO IT. I walked behind her and I yelled at her to wait and she sat down on this bench. I was so drunk and to be honest so horny I thought it was a miracle someone was finally interested in me. She put her hands down my pants and as I looked deeper into her eyes I noticed that her was a him and I felt so terrible I walked off.

I came home went straight to my room my mind a blank and just put it as far back of my mind as I could and went to sleep. I live in a small town and I saw her/him again and every time I do its so strange I mention this because last weekend I went out with a friend and she/he was at the club and she/he did not talk to me but she/he was in my atmosphere the entire time just sort of hanging around me so much so that the person I was with mentioned it. I felt uncomfortable and left.

I do not know how you guys might feel about prostitution I think their are multiple sides to it I think their are some women that might actually enjoy it I think some women are tragic drug addicts that are stuck in it and I think some women just try to see it as a unusual job and I am sure their is a small number of women that find it empowering to have men chasing them. However you might feel about it I do openly admit that I have paid for it numerous times in my life as I said I do not get female attention. So this being said I have a terrible sex life I would say that a normal man would have sex at least once a month and I have gone years without sex. So I am heading home and I decide to get a prostitute... Once again I am crazy drunk and depressed and yes I want sex but it would also be nice to have someone to sleep next to.

I pick one up and she starts making out with me and that is strange for a prostitute they typically do not do that and I should not have allowed it but its been forever so I allow it. I look deep into her eyes and into her face and I can see that behind her voice she was a he and I did it anyway....

Right now I dont have any woman I am interested in my life but one and I don't think that we will work out in the end because she cheated on me several times but you feel how you feel and I do feel love for her so I still talk to her even though I know it will end in disaster. I don't know how I feel about myself I wouldn't say that I am gay I could never be in a relationship with a trans person because to be honest people will judge me more harshly then they already do and I'm just not gay.