[/b]It was my late 20's... 27 I believe. I was extremely depressed living in a shitty part of Kentucky. I was roofing and full of testosterone and emo...ions. I was an alcoholic wreck and needed to move, feel better, or something.I ran off in search of myself in more ways than one. I found an interest in Shemales shortly after I went down south to Tennessee.Long story shortened, I will finally meet and fuck an attractive transgender "Anna"I was drinking beer and standing around my hotel door in. She turned over on the bed a little sweaty and breathing heavily, her pussy was dripping Robs thick cum onto the sheet, she took a few moments to gather herself and then looked at me “you going to finish me off?” she was sitting upright on the bed knees up and leaning back with her hands to support her. Now believe me when I say if you were to ever ask me if I would touch another mans cum the honest answer would be not a chance but when you’re in this situation with your dick pointing out in. She was very excited about them but I didn't ask why.Olivia wanted to check out double penetration videos since her boyfriend was eager to share her with his best friend and she was a little nervous about that."As you see from the picture," I said, pointing at the DVD case she held. "Your ass and cunt can more than adequately stretch to have a cock in each at the same time. I suggest you check out one of the Double Boom videos." They look a little rough," said Olivia."Yes, they are rougher," I. He stopped, then slid back away from my face. “I’m going to fuck you. Lube me up.” He handed me a tube of KY lube and I put it lovingly around his swollen cock. He leaned over and got a condom, unwrapped it and placed it over himself. I covered the condom with lube. Will moved down between my legs and lifted them up onto his shoulders. Expertly, he guided his cock to my anus and began working it into me. I relaxed and let his cock push into me, each time deeper, as he bent me nearly in half. My.
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