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 would make it law for effeminate boys to have their first orgasm this way.I think that’s what kept me interested in dressing up. That rush, heart-pounding, feeling of having the right colorful panties on. It’s like no other feeling ever. I was confused about my orgasm. I saw precum come out of my dick before but the orgasm was a feeling I never had before. It hurt a little bit but it felt soooo good. He was barebacking me, and I had the fleeting thought that I hoped he was clean, as I felt the new sensation of unsheathed cock inside me. He must have been uncut, because his skin seemed loose, and I'm ashamed to say that my ass walls were intrigued by this loose friction. He spun me around and pushed me on my back, and I tried to rise again. He backhanded me across the face and wishboned my legs and pushed in to the hilt of his dick again. His mouth and teeth went to my nipples, and I grabbed his shoulders and tried to push him off me, but he was too strong for me, and the beating he had given me had weakened me. I dug my fingernails into his shoulders and he grunted and caught me in the chin again with his fist.I must have blacked out then, because when I woke, he was under me, the full length of my body running along his, his strong arms wrapped around my chest and his cock still buried in me from the rear. We were hit with a square of light, as the door opened, and another man.
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