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I told her we had met a few women at the bar and had drank with them until closing. The one he was interested in was going across town and he was headed in the opposite direction, while the girl I liked, was going to the same area of town as me and we split a cab. As we waited I told my buddy I'd try and get this woman to come home with me and that I would sleep with her. He bet me a hundred bucks I couldn't do it and said if I did, to get her panties as proof! This was all bullshit of course, as I had been out by myself the night before, but Teadora didn't know that! I told her the woman shot me down and I had the cab drop her off at home. Anyways, I told her it was a strange request, but if she would give me the panties she had on, I'd win the bet and more importantly, save face with my friend! My stomach was doing flips as Teadora looked at me wierd, before breaking out laughing! I laughed as well and when she asked if was joking I said no, I was serious, but she didn't have to if. It started to hurt, he was slowly pushing his cock deeper and deeper. The pain kept increasing, he was 1/3 inside me and he pulled out. He spit some more and then pushed it inside. I was in alot of pain, I said "its ripping me apart" He was halfway inside me. He stopped allowing me to rest and started stroking my cock. After my pain decreased he pushed again. He was almost completely inside me, i stopped him again. He let me rest again for some time, He said "Its almost inside just a inch or two left" He spanked my ass. He caressed my chest and also spanked my ass to divert the pain. After 5 mins the pain was decreased and i gave him the go signal. He pulled his cock almost out till the tip and gave a powerful thrust inside. I screamed "Ow ow ow" He said "It completely inside now you will start to enjoy" He then slowly pulling his cock inside and outside. It still hurt but it was slowly decreasing. After 10 mins of pounding, i started feeling the pleasure. My cock was growing hard.
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