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I asked him if he thought girls and guys were attractive and he said yes. I had him lie back down on the bed, look at the pictures and start jerking off again. He was embarrassed but I told him I liked what he was doing, enjoyed his being dressed as a woman and that he was passable. I told him he really should be a she and that everyone would get excited seeing her outside and not know she was a he. He said he shaves everything and wanted to go out dressed and I said we would go out together. I told him I had fantasies about what he was doing and had worn some women’s clothes before and jacked off. I asked him if he thought my girlfriend was attractive and if he would like to wear some of her clothing and jerk off. He said yes and confessed he had worn other women’s clothing; actually he has a collection at his house. We talked about one of the neighbors that he had clothes from and she is attractive. We talked about having her and got really hot. I was rubbing my cock through my. I cycled between anger, sadness, and apathy for about two weeks. Then, something funny started to happen. Since I was no longer having sex regularly, once the sadness started to fade, I suddenly found myself extremely horny. Happiness and contentment had started to become a part of my daily emotional cycle, and now the crushing sadness made up only a quarter of my emotions, only when I was alone. But now, I was up, I wasn’t sad, I was horny. I needed to be fucked. And who better to do that than someone who had already done it so, so well so, so many times. Plus, I had a secret desire. One which I already knew he was into. I had cajoled him into telling me he was into BDSM the night before he dumped me, but unfortunately, I didn’t have time to let him know that was my thing and to try it out with him. I held my breath, simultaneously embarrassed and excited for his reply. Two minutes (120 eternities) later, he replied, “yes.” Relieved and already starting to get wet, I texted, “Can I.
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