We never jerked off or anything. We just watched it out of curiosity. That was my earliest memories of porn. One time, I was in my parents’ room that had mirrors on the wall. While watching House, I saw my mom had a bin of my step sister’s clothes. She was about 16 at the time so it was all skimpy, mid-drift shirts and silk panties. It was like the mother load of clothes for a beginner crossdresser. That was my first memory of crossdressing. I must have been 13 at the time. I don’t remember what I wore but I remember the feeling. I had the hardest erection ever and I started playing with myself. I was staring at the mirror for like 50 minutes just jerking off non-stop. When I orgasmed, it was like 4 years worth of cum. It was my first orgasm. I think because my first orgasm was connected with crossdressing, my brain probably associates the pleasure of orgasm with dressing up like a girl. This is what we sissies call destiny. I was destined to be a sissy. If I could have it my way, I. I was so enamored with my girl side. I felt more than able to pass as a girl – at least at night. Now it would be about courage and having the common sense to do this safely.I was in my own personal heaven with my new independence and privacy. I had a reliable used car and easy access to downtown Boston. I was now suddenly free to be all of whomever I was. When I moved in, I realized just how much of an accumulated cache of female clothes that I had kept hidden back home. All these female garments almost equaled my male clothing in amount! Thankfully my new apartment had two closets. Perfect for the guy going to school and for the girl who hoped to go out in public on weekend nights!By mid-August I had already twice daringly visited a rather notorious alternative bar in Boston as my femme self. I was even learning to drive with my high heels on in my car. I knew I would soon visit this scary but transgender accepting place again. In doing so I so wanted to be as pretty and as.
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