I spent the summer of 1983 in New York with my dad and stepmom. I was 18 and was in between my freshman and sophomore year of college. I had a cool job as a bank messenger on Wall Street and plenty of time on my hands. I used that time to hang out in Times Square which, at that time, was porn heaven. Many hours were spent looking at all kinds of loops in the peep booths. Everything from guy/girl, lesbians licking and sucking sweet pussies to shemales and crossdressers. I had seen my first shemale photo spread a couple years before in an issue of Hustler and was instantly intrigued and turned on by what appeared to be a hot female with a thick cock. I first wondered if I was gay, but I knew I was just much more sexually open minded than most and I just enjoyed the visual.
After one day of indulging my fantasies, I was getting a hot dog near the Port Authority bus terminal when this slender black chick approached and started a conversation with me. She told me that I was cute and wanted to know if I wanted to hang out with her. Still being a virgin and still shy around girls, I immediatley said yes. Now mind you, I was very nervous about going with her-although I was just spending the summer, I did grow up in New York until I was 14 and I knew the dangers of the city very well but let’s just say that the bl**d was in my lower head and not my upper head.
She had a little place a few blocks away-it basically was a room. Once we got there, she started kissing me and I was instantly hard. I heard her tell me to take off my clothes, and before I knew what I was doing, I was naked and lying on her bed with a raging hard on. She came over to me and immediatley started sucking my cock. The feeling was one that I could not even begin to describe and it did not take very long for me to blow my load into her mouth. This took her by surprise and she got up and went to the sink and spit my load out. I was embarrassed and thought that I had pissed her off because she did not say anything and had her back turnd to me. After a few moments she got undressed with her back still turned to me. When she turnd around, I got the shock of my then young life-she was a slender built crossdresser with a long thick cock! I was stunned, but so aroused that I could not speak. She came back over to me and started to kiss me again. I did not know what to do. In my mind I wanted to feel her cock in my hands just to see what it felt like to hold it but I was too scared to do so-hell I was scared to touch her. As I was still in my aroused/confused/scared state, she turned me over on my stomach. I felt her fingers near my virgin asshole and then I felt a cold wetness on my anus. The next thing I felt was this intense pressure as she started to slide her cock inside of me. It hurt at first but was not too bad. Once she got all of her meat into me, she started moving in a back and forth rhythm, moving faster with each stroke, but not pounding me. My senses were all over the place-I was wondering if I should like it and what would it mean if I did? I tried not to concentrate on the pressure in my ass but on feeling her body against mine and her breath against the back of my neck. That feeling made me relax and really turned me on. This must have caused my ass to relax a little bit because her motion changed slightly and she thruster just a little harder. I then felt her breath quicker against the back of my neck and her body quiver and stiffen. She then moaned and I felt her cock twitch inside of me as she shot her load into my no longer virgin asshole. My cock was rock stiff underneath me as she came.
She then got on all fours and said that I could fuck her. For some reason when I tried to put my cock in, I went limp. It was if i remembers that this was a guy in drag at that point and it killed my hardon. Without saying a word, I came from behind her and laid back on the bed. She blew me again and I immediately got hard and came once again. She then got me back on my stomach again and took me once again, depositing another seed in my ass.
Once we finished, I got my clothes, dressed quickly and left. I was reeling from what just occurred. I my ass felt squishy so I went into a public restroom stall and when I pulled down my underwear, it was full of her cum. I took them off, threw them away, wiped the rest of her cum out of my ass, got on the Subway and went home. Once home, I quickly ducked into my room and got in the bed. I told my dad and stepmom that I had a long day and was tired. Once in bed, I ran the events back through my mind and the feeling of my ass full of cock, her body against mine and her breath against my neck was enough to get me hard. It did not take long for me to blast another huge load of cum and I drifted off to sl**p.
As I write this 30 years later, it seems like this just occurred yesterday. While that was the only time I ever took cock in the ass, it was not the last time I played with a shemale/tranny/crossdresser. Thanks for reading this and allowing me to tell a story that I have never shared with anyone. There will be many more to cum!