1. Road to Ruin


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

    not a very good lubricant as I was about to find our the hard way) and smeared a handful on my ass. He then mounted me missionary style and I wrapped my legs around him as he entered me. You read all of these stories that say that anal sex hurts at first and then the fuckee loosens up and it feels ever so good? I am sorry to say that it hurt a lot at first and just got worse. I had a d***ken guy fucking the hell out of me and he would not stop until he came. I think that it took a very long time both because he was d***k and it was his second shot of the evening. I wasn't sure what to do, and I was in pain, so I reached around and put my finger in his ass and at the same time, started sucking on his nipples. That seemed to do the trick as he started grunting and I could feel him shaking all over as he bred me. After that, we both kind of passed out. I woke up a few hours later. He was still lights out. I had sobered up a bit and the reality of what I was doing hit me and I was in a panic. I tip toed to the bathroom, wiped off the rest of the lipstick, put on my clothes and left. As I sobered up, I was pretty freaked out. It had been my first experience with a man and as a k** growing up, the worst insult anybody could throw at you was fag. And here I was, completely emasculated, but really turned on by it. I was not sure of what that meant, or the consequences of my actions. I had bl**d in the toilet the next day when I went to the bathroom, but I was scared to go to the ...
    hospital. It took about four days for my butt to stop hurting. I masturbated a couple of times every night reliving the memory of that evening. I did not know my new friend's phone number and wasn't sure if I wanted to, or should, ever try to contact him again. I was not sure what my reception would be. At the same time, I was fascinated with the role I had played. I went back and forth about the experience, but what it did for me was to start me on the road to my slow transformation. I shaved all my body hair off, including my armpits and legs. I mail ordered some panties and got some nail polish from the store and started wearing panties under my regular clothing and also started painting my toenails. It turned me on to think about having that secret as I went about my regular business. I also bought a bra and some breast forms and would put them on when I was alone. But I was scared to venture out with those on. Since the time of my first experience, I spent a bit of time troubled by what happened. On the one hand, it turned me on like I had never expected. On the other hand, I was experiencing a lot of conflict with my sexuality. I will say in those days, that I would have more than a bit of anxiety thinking that I was gay. I was more than a bit ignorant of the transgender scene, which was non-existent in my home town as far as I knew, and the internet was not as sophisticated as it is now. It may sound odd, or contradictory, but I guess I convinced myself that if I was a ...
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