My first time - Sex Stories

My first time

I was a 20yr old virgin the first time I had physical sexual contact with another person - besides the light petting a (male) cousin and I got into when I was 15, and the french kissing sessions I had numerous times with my best friend's s****r. For the first time, someone was gonna touch my cock in a sexual manner and I was going to explore them too. For a couple of years, I had "played" around on the local phone chat lines that you sometimes still see on late night tv. These were free to call, totally free for women, and limited to men. It was also around this time that I had discovered my parents porn collection - specifically Peter North. His cock, was incredible and his cumshots amazed me over and over again.....if not for my fascination with boobs, I might have been gay by 18. So anyway, back to the chat lines - there was one I "experimented" with, man-line I think - geared towards gay and bisexual men. It was totally free, so I spent a few nights on there, chatting it up with guys etc.....then I realized there was a Transexual connection on there. This was always a fascination, the idea of a chick with boobs AND a cock. This was how I discovered I was bisexual. So one night, after spending a few hours at the local strip club, I came home somewhat buzzed, and headed straight to the phone, and man-line's tranny section. I had it set in my mind, that I was gonna try a tranny. I lucked out, there was one on there that was very open to virgins, and she could tell that I ...

... had no experience. She invited me to her place for some intimate fun. I was in no state of mind to say no - so I blindly agreed to drive downtown to her place. Reflecting back, I was very fortunate that this was a legit interaction, and no foul play occurred. So I arrived at her place, she greeted me at the door with a sexy lace outfit, invited me in. The mood was already set in her apartment (candles, light music, musky smell of eroticism and blankets covering the couch), and she offered me a drink and suggested I get "confortable" on the couch. She returned, and asked if I minded if she put something on the tv for a little inspiration, to which I readily agreed. So she put in a bi-sexual porn movie, and we proceeded to watch for about 15-20 minutes. About this time, she suggested I get more comfortable - I needed little encouragement after this, as I immediately shucked off my jeans and underwear, as well as my shirt. To my surprise, I was totally comfortable getting naked in front of this stranger, seeing as how I was always conscious of my size in public places. She was delighted to find my little cock already at attention, and she proceeded to strap a condomn on my hard cock. Next thing I knew, my cock was disappearing in and out of her warm mouth, and much to my delight, I was able to control my orgasm. We took turns between making out and her going down on me, until she asked the inevitable question - "how far do you want this to go". By this time, it was clear that she ...