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I decided to just lie on my bed with the butt plug in me, stretching me to give me some time before inserting its big brother. 15 minutes later my ass felt completely fine and I knew it was time. I lubed up the big one and as soon as I took the smaller one out of my ass started to insert its big brother. The first few inches went in very easily, until the fat part (6 inches in diameter) started to push against my ring. Oh my God, the pain shot through me. I found it easier to lie on my side with one leg pulled up to my chest, gently pushing fat boy into my ass. My whole body was tingling and my little clit was beginning to dribble my sissy cum, with a final push, the butt plug entered my ass, and I smiled with the achievement. I knew then that I had proven I was worthy of being Daddy's little sissy bitch, he could have my boy pussy any time he wanted. My chest swelled with pride, this was my role in life. Again I lay on the bed this time for about an hour feeling how I was stretching. The feeling was fantastic, the nylon was silky smooth and teased my dick when I walked around. When my mom was at work, I'd go through her underwear drawer and slip on a pair. I loved how it made my dick feel and go all day till just before she came home. My friends and I were talking one year about a party at the local hotel and if we were going to dress up and go. They spoke about going as football and baseball players, movie heroes and villains. I thought that was so generic, and didn't want any part of it. While at home wearing my moms panties I got the idea of going as a woman. I called my cousin and she thought It was funny as hell to see me dressed as a girl. I had a stringy body, with feminine features and no facial hair and little body hair. So a week before Halloween I met her at a used clothing store. She picked out a dress and shoes, some jewelry and a hand bag. I asked her " what about lingerie ". She said " used, gross ,If you really want to, I'll give you some of mine.
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