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One Christmas Stan came out of the closet during the Christmas holidays. We were all proud of him. Most of his friends weren't surprised as he had always been discrete about that part of his life. I remained friends with Stan after I divorced his sister although we rarely hung out any more. But one night I got together with him and a couple of friends and he joked about how one time he cross dressed at a Halloween Party at a gay bar and was the spitting image of his younger sister. Everyone laughed and the conversation turned to other things. There was no smoking allowed inside the house we were at so Stan and I went outside to smoke. While we were outside Stan suggested that he come over to my house and dress up like his sister. He told me that I wouldn't believe it. "Sure, sounds like fun." I said, knowing that Stan had always been reserved around his close friends about his sexuality.So, I didn't really know what to expect but didn't figure anything sexual would happen and just. "Do you want this?" I heard him whisper, his mouth on my ear, the tongue slipping in and hot breath on my neck. I lifted my ass and said: "Yes." He had never tried penetration before so I was totally surprised - and hot as a bitch in-heat on her wedding night.As so, the fuck began. He took his time slowly pushing that cock into me. We had to stop a couple of times as I adjusted the inner muscles to accomodate the width and the length. It had been many years since I had been penetrated. But fuck, it felt good - the slight pain and "filled" feeling. He showered kisses on my neck as he pushed further.When I got to my comfort level and he got balls deep, he began slowly plunging in and out. I felt so fucking good. I surprised myself by spreading my legs and raising my ass as high as I could. I simply ordered him to "Now fuck me! Own me! Make me your bitch!!" And then the real prostate massage began.He lifted my hips with both hands and plowed it until I felt like rag doll impaled on a.
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