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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 would make it law for effeminate boys to have their first orgasm this way.I think that’s what kept me. I started in a very businesslike way, but when I moved on the chair and my legs opened a bit – for just a second – he couldn’t remember what he was saying, and had to ask me to read back what he had said. It was all I could do to keep from laughing at him and the look on his face was priceless. By the time the letters were done and I took them back in for him to sign, I was getting very horny. As I stood there watching him sign the letters I was almost dripping wet and as I put the letters down he asked me to come around his desk because he said that I had a typo he wanted to show me. Now there’s no need for me to come around his desk but he asked so I did, and he was right I had a wrong letter in one word so I said I would retype it. Then he said for me to wait and he would check the other 16 pages in case I needed to fix another ones as well. As I stood beside him his hand next to me went down to his leg and slowly moved over towards me, then up my leg. I didn’t.
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