1. Road to Ruin


    Date: 9/29/2015, Categories: BDSM, Fetish, Author: klammer, Rating: 100, Source: xHamster

    Jamie's Road to Ruin Part I am about to tell a story that is true. It was my first experience but it shaped my life forever, not necessarily for the better. As a c***d, I used to fantasize about being a woman, but never acted on it. Anything &#034gay&#034 freaked me out. In any event, I was very closeted and repressed. And very awkward around women I was attracted to, but seemed to be able to make a lot of female &#034friends.&#034 Years ago when I was in my twenties, a female friend of mine, Karen, tripped and fell and cut her chin open. One of her girlfriends, Kathy, loaned me her car to give Karen a ride to the hospital. After taking my friend Karen to the hospital and getting her stitched up I drove her home and then drove the car to a bar that had bands that play jazz where Kathy was, so I can return the car. I had expected Kathy to have the courtesy to drive me home but she didn't want to do that so I was kind of stuck. I decided to hitchhike home. After a brief period of time, a fairly conservative looking guy picked me up and asked me where I was going. I gave him directions and off we started. I suppose I should describe myself. In those days I have very long hair which reached down to the middle of my back. I was tall and very slender. Jerks used to shout at me from their car windows &#034are you a boy or a girl?' In any event, my rescuer was a fairly large and burly looking guy, but seemed friendly and we had a pleasant time talking. In those days, I lived in a ...
    college town and hitchhiking was a viable means of transportation and a good way to meet interesting people. He asked me if I needed to get home right away and I told him not necessarily. We stopped at another bar he was familiar with and listened to a live band this guy knew about. It was a country and western band, which wasn't really my thing, but they sounded pretty good. It didn't seem like a shitkicker bar so after my initial anxiety, I was reasonably comfortable. I remember my benefactor kept saying of the guitar player &#034he plays a mean guitar doesn't he?&#034 He said that many times and I think he was pretty d***k by then. We got back into his car and he then asked if I wanted to stop at his house for more drinks (he said it was close by and that he would drive me home after that). I was pretty blasted at that point, having been drinking all night. I said ok, and we talked some more, then, after a few minutes as we were driving, he asked me if I had ever sucked a cock. Out of the blue, as we had not talked about anything sexual all night. I was very nervous, and felt butterflies in my stomach like never before, but at the same time, I became pretty excited (and as I said, I was really d***k). It had been something but I had fantasized about for a long time but never had acted on. I have always had fantasies of being a woman, or at least playing that role with a man. When I looked at porn, it was always straight porn, but I loved watching cocks and cumshots more than ...
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