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Richard shifted behind me and I felt the tip of his cock press against my asshole. I did my best to relax knowing it would only hurt more if I struggled. I was still tense and I felt Richard rub my back. I was surprised at his gentleness but was shocked back into reality when I felt his cock press past my tight hole. I grunted and whimpered again as Richard moaned. He held himself there just the tip of his cock inside my ass. After a few breaths he pulled out rubbed the head of his cock against my wet cunt then pushed the head of his cock back into my asshole. He repeated this a few times then when he was satisfied I was lubed up enough he pushed a bit deeper it still hurt and I yelped. "Please no," I whimpered, "You're too thick I can't take it."Richard rubbed my back again and said "Shhh just relax and take it slut, and trust me you're gonna love it."I lowered my head again and as I did Richard forced more of his cock into my ass. I try not to jump but the pain takes over and my. "Well, I was very excited at the thought, as I had been dressing for years but I'd never confided that to anyone. So, casually, I mentioned that another friend, Melissa, had recently said it wasn't fair that women could wear skirts & pants but men could only wear pants. I told Kim how I had assured Melissa, who everyone knew I had a crush on, that if she would marry me, I would be glad to address this inequity by wearing the wedding dress. Melissa had promised me that if we did indeed marry, she's be glad to wear the tux and she'd love to see me in the wedding dress. We had laughed it off, but Kim said that she thought it would be fun to dress me up sometime to surprise Melissa. I said okay, figuring nothing would come of it. Shows what I know.A few weeks later, I was driving home from a club and as I went by Kim's house, I saw her sitting on her front stoop. I stopped and joined her. She told me that her parents were away in Europe and she was waiting for Angela, who lived.
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