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I was trying but now on day three it was still hurting, and I was still too chicken to attempt it any further because the sharp pain was not going away. I talked to Rich on the phone and told him what was happening and how I was still unsure because of the pain. He laughed and told me that the pain would go away, and I would ultimately feel natural with it, that he would be gentle and that I had already told him how badly I wanted this, so I needed to keep trying. Day three was when I succeeded. I didn’t have to work until the evening so I got up early in the day and rolled over in my bed, reaching for the bottle of lube that he had given me I pumped a handful and began to rub it around my pink asshole, moving my hips as I did this on my stomach with one leg up I inserted a finger in and this didn’t hurt at all, I felt warm and left it in there until my body relaxed and I could begin sliding my finger in and out slowly. After several minutes of this I felt my hole begin to numb a bit. He went into the bathroom and got his lube and came out and was lathering his cock while I was licking my wife's pussy. I felt him place the head of his cock against my asshole and he told me to "try and relax and don't tense up" I did what I could but I felt him enter my ass and immediately let out a thunderous groan. He eased it in at first but than started pumping faster and faster, My attention wasn't eating my wife's pussy anymore but the huge cock I had slamming my ass. I felt like I was gonna pass out from the pain but at the same time it felt really good. My wife was looking at him telling him to "fuck him harder" and he did. she held my face so I was looking into her eyes and she wiped away the tears I first had when he put it in. He was moaning loud as he pounded my ass. He pulled out of me and I sighed in relief but a part of me wanted him to keep going. He told my wife to bend over next to me and she did, I heard him lube up his cock again and soon he was sliding his.
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