Let me start off by saying I'm straight. I'm very attracted to women, but feel absolutely no attraction to men.
When I was younger, I always had a fascination with anal sex. I don't know why, but from when I first started looking at porn on the internet, I was always looking for anal sex. The odd thing was, I wasn't so focused in on the penetration of all the tight asses (although I enjoyed that as well), I really loved watching the girls faces as they took big dicks in their asses. They usually had fake expressions as they took it in the pussy, but they became all serious when something was getting shoved up their back door. They looked very focused and nervous as it began pumping into them, faster and faster...and then the ecstasy they seemed to be in when they got use to it, and it began to really pound their hole.
After quite awhile of exploring this (I guess you could call it my fetish)...I began to go further into it. I started to realize that I was more turned on by thinking of what it must feel like to take it in the ass, than to give it to someone in the ass. I refused to consider guys because I know I am straight...so this lead me to shemale/transsexual porn. While I enjoy it all...I really get off on the transsexuals who are tops. I swear, I still believe there is nothing hotter than a top transsexual giving it to a guy...and for some reason, I really love it when its pretty rough. The slamming of the bodies, the fact that the guy is just getting used to get the tranny off...just a hole to pound as hard as they need to get off...for whatever reason, I found this ridiculously desirable.
Well, it really got to the point where I was only looking at this kind of stuff to get off. I felt a real need to act on it. I'm pretty shy around women, and had not had sex yet (22 years old). The thought of a woman doing me with a strap-on would work for me, but I just cannot see myself ever asking a woman to do that to me. The thought of meeting a shemale would also be perfect, but I figure my chances are quite slim on that as well. So, I figured that meeting a guy would be my best chance.
There are a lot of ways I could meet with a guy for sex, and sex only without anyone knowing. I figured me being a virgin would be a pretty good draw. I also figured that if I was going to go through with this, then I would really prefer to do it based completely off my hottest fantasy. What was that you might ask? Well...it really involved me having no control...and being used anally for as long and hard as the giver was willing. I posted on a couple sites exactly what I was looking for...someone dominant, someone a top, and someone willing to use a virgin bottom roughly. Preferably tie my hands behind my back so I would be pretty helpless...then bend me over something, or put me flat on the bed before using me.
I had no real specifics on body type or age or anything. Like I said, I wasn't going to be attracted to them anyway. If anything, I'd probably prefer they be not of huge endowment given that I wanted to session to be rough (them slamming their whole body weight into me with each penetration of my hole).
After several conversations, which usually led to me saying I'm interested, but never following through (I wouldn't make a date...doing that then not showing up would be a terrible thing to do)...I finally got up the courage to follow through. I had only been signed up with Squirt for a couple weeks when someone messaged me and described pretty elaborately what he would do to me...using specific requests I had made in my profile into his scenario. I decided it was finally time to follow through with this...and setup a date to meet him at a hotel that he had picked out.
Now, when I say I was a virgin...I mean it. The only thing that had been inside of me was 2 of my fingers. I had done it in the shower a couple of times. I never got all that deep, and well, 2 fingers are not that wide. I used an enema on myself the morning of (we were going to meet at noon)...and shaved all my hair on my ass, balls and around my dick. This was the first time I had ever done this...and I was really turned on by how it looked. I was getting really nervous, but there was no turning back...I had to go through with this. I checked my e-mail and found one from him just like he said there would be...with the room number in it.
When I arrived at the hotel, I knew what the plan was. He had told me that he would be in his car while I went into the room first. I was to take off all my clothes and put the handcuffs that were on the bed onto myself (behind my back)...then lay face down in the middle of the bed. As I was doing this...I could feel my whole body shaking. Fear or anxiousness...I wasn't sure. After clicking the handcuffs on I began to consider how risky a thing this was to do. I quickly dismissed it and told myself that this would only lead to me living out a very hot fantasy and that was it. I assumed the position on the bed and waited. It only took about 5 minutes until I heard the door open.
We had corresponded for a few days before we agreed to meet today. He had asked me specifics about all my fantasies, and things I wasn't so interested in. I had told him that in the future I wanted to try being a part of a group. Having several guys use my ass for a long period of time really sounded hot. I had told him about my interest in cross-dressing, and being used like a girl. I also expressed my lack of interest in giving oral or kissing. For me, it was really just about getting used up the ass roughly. However, if they made me give them oral...I guess there wasn't much I could do given the fact that I was tied up.
I heard the footsteps leading to where I was on display (face down on the bed, arms cuffed behind my back). I kept my eyes shut, a little overwhelmed by the moment. I could hear his clothes rustling as I assumed he was removing them. As the rustling stopped, I felt him pull me by my arm so my head was over the edge of the bed. I opened my eyes and found his semi-limp dick directly in front of my face.
