How I became a sissy crossdresser!

My older sister encouraged my crossdressing.

I was about 13 when I first became inclined to wear women’s clothes. I would find my mom’s bras and panties in the laundry room and try them on. Every time I did this I would get an instant erection….we’re talking hard enough to cut glass. I had learned to masturbate a few months earlier and took advantage of every opportunity. My 16 year old sister was a popular cheerleader, and so were most of her friends. One day when my parents were at work and I knew that my sister and two of her friends were at the bowling alley, I slipped into her bedroom and tried on various outfits…panties, bras, high heels, and even her cheerleader uniform. I was wearing a pair of her bikini panties and a cute little bra and admiring myself in her full length mirror and stroking my hard little dick frantically when Pam (my sister) and her friends came walking into the room. They had returned home much earlier than I expected. I could have died right there! All that I could do was run into her bathroom, slam and lock the door, and start crying. I just knew that Pam and her friends would tell everyone at her school what a pervert her little brother was and how they had caught him yanking his little dick while dressed like a girl. As it turned out, I was very lucky. Pam swore her two friends to secrecy and they agreed to never tell. After her friends left, it took her almost an hour to coax me out of the bathroom. I was so ashamed that I couldn’t even look at her. But she sat beside me on the bed and told me not to be embarrassed. That my feelings were not in any way perverted but could very well be natural. Crying my eyes out, I told her how much I envied her and her friends and how much I had always wanted to be like them. The truth was that I really really wanted to be a girl. Well, Pam understood. Instead of selling me out to our parents, she agreed to help me and for the next few years she encouraged me to crossdress and helped me buy several wigs and even taught me how to do my makeup and how to walk in high heels. I live my life today as a woman…yes, my parents eventually found out. They were not happy about it, but Pam and I have remained close. Last year, one of Pam’s boyfriends tried to hit on me when she wasn’t around, and even though I would have been very happy to suck his cock and let him fuck me, I stayed true to my sister. I told her about his advances and she dumped him soon after. I owed her too much to betray her.

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