This took a lot of convincing and a lot of drinks. She went first telling me she prostituted herself when she was young and would take on multiple par...ners.We talked a bit about hers then it was my turn to confess. I told her that I had cross dressed most of my life on and off. She was shocked at first then laughed saying no way you do that. I assured her that I did and was feeling a bit embarrassed about it. She said I want you to prove it or I don't believe you. After another drink and a lot. We didn’t waste any more time.She asked me to get the bottle of lube from her bag, and I didn’t need any more instructions. I made her be on her four with her ass raised a little by placing a pillow under her. I looked at that nice ass and thought how lucky I was to have her. She was getting impatient and asked me to just put it in.She needed to feel inside. I applied the lube on her asshole and slowly started inserting my fingers there. God, she was tight as fuck! It took a while until I could. More

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