Believe me, it’s toughest to tell him a no. He placed the condom on his dick and applied lubricant on his dick and my ass hole. He tried a lot but his dick didn’t go in.At one point we both started laughing at this. He started fingering me with one and then two fingers. Then tried with his dick again. This time his dick went half in tearing my ass. I began to shout on him to take his cock out but he asked me to wait. He began kissing me on my neck and back.After a minute or two the pain reduced and he again gave a push. This time his dick was completely inside. I again shouted in pain. He waited for a minute but continued licking my neck. Then started fucking me. He was going slowly, with time pain reduced and pleasure was on heights.We both were moaning loudly with thumping noise filling the room. I asked him if he can fuck me in missionary position so that I can see him fucking me. He then turned me and placed my legs on his shoulders and began to fuck me. That way he was looking. She wouldn't explain more, but Tim trusted her, so he hadgotten dressed in his sexiest lingerie, his best red dress, shoulder-lengthblonde wig, 3" heels, and stockings, and come over.A small square opened on the center of the door and he heard a woman ask,"May I help you?" Yes, I'm Tamara. Lydia sent me."The woman's voice almost immediately took on a hard edge. "Ah, yes. Comein," and with a very snide tone, she added, "little girl."As the door opened, Tim sighed. Lydia had probably told her about hiscross-dressing, thinking she was someone to be trusted. But Tim had had todeal with a lot of prejudice about his cross-dressing, both from men andwomen, and had learned to tolerate the crap. He could tell already that hewas going to get more than his fair share from this woman before the nightwas over.Part of him felt that he should turn around and walk away, but he had toldLydia he would come, so he walked through the door and followed the womandown a short hall to a small.
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