My first time as a Femboy CD

My mom worked 2 jobs to support us and my sister worked and also was out a lot on dates so I had plenty of alone time to dress up. I searched the internet and found videos on how to apply make up in many different styles, I liked the gothic style the best when I first started dressing, and I would practice walking and talking and acting like a girl around the house until my little cock was about to burst and then I would masturbate over and over until I was spent and exhausted. Then when I was 14 something strange happened, my masturbation fantasies turned from me being dressed as a “sissy girl” and having sex with girls and thoughts of my sister touching me as I was dressed as a girl to my friend David.

I guess you would call David by best friend. He was almost 2 years older than me and lived with his grandmother in the apartment unit right below mine. I had known him since I was 10 and we hung out often. You would think if I was going to start fantasizing about another boy sexually I would have picked some athletic jock, but that was not the case. For some reason that I could not explain when I was 14 I started fantasizing about David sexually when I dressed. I fantasized that I was his girlfriend and I would suck his cock and I even fingered my own butt thinking of David fucking me there. After I came I was embarrassed and ashamed of myself for fantasizing about him sexually and would question myself until I got aroused again and then I would once more think about being his girlfriend. But why him? I could not understand it.

David was a nerd. I don’t mean a glasses wearing skinny nerd with an inhaler who got beat up often, but he was a nerd and really into fantasy stuff. He was taller than me, my sister said he was nice looking but not her type (David had a huge crush on my sister), and very shy and somewhat reclusive. He preferred to stay inside reading a fantasy book about elves and magic or playing Dungeons and Dragons (okay I played with him sometimes and soon that became a sexy game for us to play), or fantasy video games.