So it was a weekend and I helped him to dress up in a red dress with matching heels and panties. I made his hair in a high ponytail and he had shaved all his body hair. I helped him apply the makeup and he looked so much like a pretty girl. He was very happy himself. So we went out to a LGBT friendly bar and went on to dance. A couple of butch girls, wanted to dance with him but I didn't let them. He was all mine for the life. He even got a few looks from the other men and gurls around. We had tremendous sex that night.After that night, it became a weekend ritual. After a couple of years, he had a wardrobe of his own and even allowed me to take him to a salon and get his hair cut in a feminine style but still would wrap his hair in a bun at work. We soon had a lot of Cross-dresser friends and even a few lesbian girl friends and we would hang out a lot on the weekends. Life was going pretty good.One of our friends, a cross-dresser himself, asked me if I wanted to earn a lot of money. His hands were all over me and mine him as we kissed then I felt that feeling again, that pressure at the entrance to my arsehole. My god he didn't think he could fuck me with that monster between his legs did he. My body moved without me asking it too. My legs opened wider and I bent so as too give him better access. It was like my body knew what too do. I felt him try to push in and it hurt. I could feel my hole opening to try and take him but he was just too big. Well that's what I thought until I felt something like a pop and he was inside me. Not much. I couldn't see but I was guessing just the head of that a****l was in me. It felt like I would be ripped in two but his kisses had me turned on so much I could feel my own cock grow harder and harder.He slowly rocked on me and I moaned out load. It hurt but it felt so good at the same time. More and more of him was sinking inside me then he was at the same point as the dildo. The bit that had hurt. The dildo hadn't hurt too bad. It.
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