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I hesitated for a minute, "Fine, why not?" I said, "what is the bet?" Let's bet on who'll be the maid of this room for the evening." he said."It's my room." I told him, almost offended."Yeah, well, you were the one who brought it up. Plus, you always boss me around when I'm here." he said, "Whoever's smaller has to wear this maid lingerie that this chick left in my room the other night, and be the winners maid." Okay, fine." I said, hesitantly, as he started pulling down his gym shorts. I pulled down mine, revealing my laughably small bulge, which was already growing from my excitement and nervousness. He pulled his boxers down, letting his already twitching cock slide out from underneath. It was huge, even though it wasn't fully hard yet, I could tell it would dwarf mine. "What are you waiting for, dude?" he teased."Nuh, nothing." I stuttered, before pulling down my boxers, revealing my 3 inch cock, already nearly fully hard from how nervous I was. He stared at it, and smiled a. Without a second thought, Damien unzipped my skirt and let it fall down to my ankles. He pulled down the pantyhose and panties that were hiding my asshole and let his cock tentatively touch my ass opening. "You have such a virgin little ass," he said, slowly pushing his cock inside me. I gasped. The dildos were one thing, but a real cock was an entirely different thing. His cock was warm against my ass, and larger than the dildo I had been using. I was scared to have it rammed into my ass but excited at the same time. "Just take a deep breath," Damien said, slowly pushing the head of his cock into my ass. Just as he instructed, I breathed deep. The initial head, although larger than the dildos I had been using, was larger than I was used to, it wasn't too bad. My ass we being stretched, but I knew what to expect. Damien slowly pushed more of his cock into my ass, and soon he had his balls touching my ass cheeks. I could barely breathe. I had never had such a large amount of anything.
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