My first time as a Femboy CD

I hung out with him a lot and soon would just stare at him as he played a video game and would stare at his crotch wondering what his penis looked like and what it tasted like and if his cum tasted like my own. When we played D&D we were sometimes joined by 3 other boys from I really did not know well. Only one went to the same school as David and myself. They were “nerds” also but nice except for a boy named Derrick. He was a jerk, at least to me. He went to some private school and when we played he would always make crude comments about my female character, like "have her come suck my cock" etc. I started using female characters and the seemed to like that and we had fun placing my female character in sexual situations. I would get so horny as we played and I knew they did as well. We were teenage boys after all and sex was a focus in our life. One day when alone with David I told him of my crossdressing secret and figured he would not mind since he is into fantasy and all that he would just think of it like a costume or something. I would not try to seduce him of anything, that would be too weird anyway since I was not gay just confused and I knew he was not gay by the way he looked at my sister all the time. I just figured it would be fun to be dressed as a girl and play a D&D game with him or something. I knew he would not tell anyone and I trusted him.

I did not just dress and surprise him, but instead I talked to David and told him what I wanted to do and he laughed and said that was cool. He was really into cosplay and comic book and fantasy conventions anyway so he just thought of it as a form of cosplay.

The hard part was to decide what to wear. I could not “borrow” any of my sisters clothes and needed some of my own, but where to get it. I decided online for the clothes and then s store for the underwear. Online was tricky since I was only 14 and had no credit card, but then another idea hit me. My sister was 16 but she had a debit card with her bank account and I talked her into letting my use it after I gave her the money out of the savings I had accumulated from birthdays and Christmases.