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Underneath I went with a red lace thong and it’s matching strapless bra. I clumsily applied make-up like the woman at the spa had instructed me. It took a lot longer than I had imagined but the end result was worth it. I checked my look in the mirror and was damn impressed if I do say so myself.During the drive to his hotel I had many conflicting thoughts and emotions. After all I was a man less than 48 hours ago and yet I found the male aspect of my psyche often being lost in what I can only describe as feminine rational. Physically I was female and I felt the need to be as such but the male part of me was wondering if this was right. I wasn’t gay and had never had any inclinations to such so my mind was at war with itself. Ultimately I decided that anything I did while in this female form was not a reflection of my previous self. In fact I made a conscience effort to block out any male thought processes for the evening and by the time I pulled up to the Regal Inn I was 100%. 27 I believe. I was extremely depressed living in a shitty part of Kentucky. I was roofing and full of testosterone and emotions. I was an alcoholic wreck and needed to move, feel better, or something.I ran off in search of myself in more ways than one. I found an interest in Shemales shortly after I went down south to Tennessee.Long story shortened, I will finally meet and fuck an attractive transgender "Anna"I was drinking beer and standing around my hotel door in Lawrenceburg, TN one late afternoon when I saw 2 attractive females drive by my room and on down to another room at the end of the motel lot. Apparently they was having a party of some kind.I recognized both of the girls from school but wasn't sure if they did me. I just wanted them to notice me and invite me over. So I keep my attention on them. They both seemed interested in me and we eventually wound up drinking and hanging out for most of the night. I got drunk and flirted hard with "him" we made out in "her.
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