I knew that part of me felt right and fulfilled being feminine and feeling his cock respond – it was powerful and erotic and all oh so feminine. I jumped back onto the dating line as soon as I could and started looking for my next man. After a few days I struck up a conversation with a guy named Tony. He was very experienced and very much into gurls like me. I arranged to meet him in the lobby of his apartment building. He told me to wear stockings, panties, and bra under my normal clothes – no socks so that my stockings would be visible to him. I was to bring heels and a dress in a bag.When the day came I made sure to be at his building a little early and sat in the car more aroused than I had ever been in my life waiting for the time to come. At the appointed hour I got out, opened a button or two on my top (until my bra was visible if I leaned forward) and headed to the lobby. He was waiting and, to my surprise, kissed me openly in front of the guard. We rode the elevator up to. We had a friendship before our first sexual encounter. Granted it wasn’t a strong friendship, but it was a friendship nonetheless. Unlike Jimmy, Clint was fairly nice and not against sharing a bed. Some days I’d grab us coffee the next morning and we’d sit in bed talking about the night before or other various aspects of our lives. By no means was the sex regular but I spent quite a bit of my free time at his apartment when our schedules allowed. Clint had an intense anal obsession. He was so anally focused that we had never engaged in vaginal sex. I found it odd and wondered to myself if he was bisexual or even gay, but didn’t dare bring it up to him for fear of ruining our friendship. One outcome of our friendship was learning more about anal stimulation and orgasms, both for him and myself. He taught me how to finger his ass while giving him a blow job - which he said led to incredibly intense orgasms. Alternately, his fingers were incredibly adept at finding my.
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