First time was about five years ago. I had always been attracted to women and dated women. Love a hot redhead with some freckles...If only the Little Mermaid was real. At some point I decided to watching some gay, tranny and bi porn online out of curiosity. I have always appreciated a good looking and well built guy, but never in a gay way. More out of a want to work out more. One day I had been watching some porn, a little of everything and decided to meet up with a guy. I figured you only live once and you don't know until you try it. A few weeks later I got up the courage to post on craigsl... Continue»
I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She was a smooth slim tranny and she loved to suck cock and get fucked and that's exactly what I was looking for. I was also curious about playing with and sucking her cock as well and she was into that too. Before long she gave me her address and phone number and I told here that I would be there in 30 minutes. I had a rush come over me as I contemplated actually going through with this. I had a couple of more drinks to build up the courage and reduce my inhibitions. I really really wanted to go through with it but still wasn't sure I I really could. I wrote down the directions and her number and off I went. She lived in an apartment building near the train station and when I got to the parking lot I called her. She had a sexy voice with a chinese accent. She told me where to park and gave me instructions on which door to go to where she would buzz me in. At this point I was shaking with anticipation and was still contemplating backing out. It was a good thing that I had a buzz or else I probably would have. So I entered the building and she buzzed me in. I took the elevator to her floor and knocked on the door. When the door opened, I couldn't believe it. She was so fucking hot. Probably about 5'6", 120lbs, nice smooth complexion, black thigh highs, garters, heels and a lace top, oh and a wig and all the make up too. She smelled very strongly of perfume and her place was well kept. She looked me up and down and approved with delight. I stand 6' tall with an athletic build at about 185lbs and very clean cut. My cock was now throbbing as she e****ted me into the bedroom. There was some tranny porn playing on the tv and candles burning. She then asked me to get undressed. I stripped down completely nude. My cock was raging. She was laying back on the bed and I straddled her face and buried my cock in her mouth. She took it like a champ. It was at this point that I reached back and felt a cock other than my own in my hand for the very first time. Her cock was very nice, probably about 6" and fairly fat. Now she (her name was Sarah by the way) started to really take charge. I was a bit surprised as I was more expecting her to be submissive. She had me lay down on the bed and we went into a 69 position. she straddled my face. Another first for me! I was actually sucking a cock and it tasted so good! Sarah was going to town on my cock and working her way down to my asshole. She started tonguing it and working a finger in. So I did the same. I really worked her tight little Asian asshole good with my tongue. Oh, she introduced me to poppers too, so at regular intervals we would both take a hit. It brought things to a whole new level. After a while of sucking eachother's cocks and tonguing and fingering our assholes I wanted to fuck her. This is when she really started to get more aggressive. She started making me beg her to let me fuck her so that's what I did. She really wanted me to fuck her bare, but I refused. She almost wouldn't let me fuck her with a condom but she finally did. Her smooth asshole was so fucking tight. I fucked her for a while but she said that it hurt too much. Then she wanted to fuck me! I couldn't believe that I was going to get fucked too but it was so hot that I couldn't resist. She entered me missionary and it hurt a bit but we each took another hit of poppers and she slid ritght in. She was fucking me for a while before I realized that she had taken her condom off. I was a bit nervous, but it was so hot I let her keep going. She was pounding my ass and feeding me poppers every few minutes. It felt so great. After what seemed like forever she ended up busting the biggest, hottest load of cum right up my virgin asshole. She buried her cock balls deep up my asshole and I milked her for all she was worth. I could feel her hot cum pumping into my asshole. It was so fucking hot! She pulled her cock out and demanded now that I fuck her bare and seed her ass so I did, but only after she ate my semen filled ashole out! I then bent her over doggy style and squeezed my cock into her tight, smooth little asian fuck hole. She moaned and demanded that I fuck her hard and deep. I could feel her cum dripping out of my own asshole and down my leg while I was pounding her hole. I couldn't take it any more and I must have busted the biggest nut of my life. I hope her neighbers weren't home as we both lost complete control. I stayed in her asshole for a couple of minutes and finally pulled out. Looking at her wet, worn out asshole dripping with cum was fucking hot. I then got dressed, said goodbye and went on my way. I hope you enjoyed the story of my first experience with a tranny. Let me know and I will share my second experience!