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(She is so cool!) I took a hot bubble bath and shaved what little hair I had on my legs, underarms, and pubes….just in case, you know. I assured her I would be with Ray and she was OK with it all. Mom was aware of my crossdressing for some time and she was resigned to the fact that I was transgendered, so I told her all about my outfit for the party and she was only concerned for my safety. Ray was picking me up at 7:30 and I wanted to be sure and look extra special for my coming out to the world. I already had a sexy white bra and panties! Those next few weeks I was a little nervous but excited to be dressed as a slutty nurse in public and in front of Ray and the other people at the party! I almost chickened out when the day finally arrived but I stuck to the plan and started getting dressed around 5. “So you’re dressing as a girl? “Yeah, is that OK with you?” “I guess.” He said, than added “That, I have to see.” That night I went online and found a sexy nurses outfit at a costume shop and bought it along with a pair of white high heel platform peep toe pumps, white seamed stockings and a white lace garter belt. Ray gave me a funny look and said “Male or female nurse?” “Female of course, silly boy” I replied. I held my breath and I said that was perfect, and blurted out that I would go as a nurse. He decided on dressing as a doctor, since he was starting pre med in the fall. Ray gave me a ride home from school that day and we talked about what to wear to the party. I tried to think of how I might tell Ray about my little secret but just couldn’t get the nerve to say anything to him when one day the opportunity fell from the sky! A mutual friend of ours, Sandra, the rich bitch slut in town, invited us both to a Halloween party she was having, and right away I knew this was my chance. Ray had always jokingly called me his little fairy friend so he knew I was probably bi or gay or something but he always made sure I knew he wasn’t by telling me about all the girls he supposedly fucked and how horny he was for pussy all the time.
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I hoped I could live full time or mostly so after graduation, and I went out to the mall a few times dressed as Lisa and I met maybe 10 or 12 guys on line that I hooked up with and blew so I was pretty confident about how great I looked as a slutty chick as well as my oral talents, judging by the compliments I always got. Entering my senior year of high school and dressing for several years already I was beginning to get a little more daring in my crossdressing. As much as I wanted to be with him I didn’t want to risk our friendship. Ray was often the object of my fantasies when I dressed, but I as straight as an arrow and I was always afraid he would freak if he knew about Lisa. Ray was big and strong and cute as hell and I had a secret crush on him since 9 th grade. Ray lived next door to us since we were kids and is the same age as me so we grew up together. (At least that’s what I thought at the time.) One of my best friends was a good looking guy named Ray. Even most of my best friends had no clue. I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.Īt that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa.