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.
He pushed himself against my lips and I reluctantly agreed. I figured the quicker I could get him hard, the quicker we could move on to what I was here for. I wasn’t really all that enthusiastic, but I allowed him to pump into my mouth…fucking it to some degree. I didn’t really use my tongue or anything, but I did gag a little as he started to fully harden. At last, he pulled out, and I was pretty relieved that we were done with that part…I didn’t enjoy it in any way.
I watched as he reached for his pants that were on the floor and removed a condom from the pocket. I thanked God that he followed through with his promise to use protection (which I demanded). I only just now realized how he could have chose not to use it and there would really be nothing I could do to stop him. He slid it on as I looked over his dick for the first time. It wasn’t all that big…thank goodness. I would guess it was around 6 or 6 and a half inches at the most. I felt this would be the perfect size to allow someone to really pound me without killing me.
He walked up behind me and said his first words. “You ready for a plowing honey?”
A little bit ashamed, I didn’t speak…but just nodded my head up and down. I felt his body weight shift onto the bed behind me. He pulled my legs apart and moved in-between them. He placed and hand on each shaved cheek and spread them apart. Then I felt it…No, not his dick, but his tongue. I had told him that I could only imagine how great rimming would feel in one of our previous e-mails…and now he was doing it. His tongue was taking long drags from just below my balls, to the top of my crack. He did this 3 or 4 times before settling on my hole and licking hard against it. I let out a moan as I had never felt anything this good…Hell, I had never imagined anything could feel this good.
After about a minute or two of this, I felt two of his fingers sliding in my crack. He decided to skip just one finger, and pressed them both against my virgin hole. It was definitely tight, but he was able to get them inside of me. He only pushed them about half way in, before pulling them almost all the way out…and then back in to the same depth. He was doing this very slowly, and it was really feeling quite great. It actually felt better than when I would do it to myself…although I couldn’t say why. I tried to squirm back a little bit to get more inside me, but he spanked my left cheek…he said he wanted to be able to get his dick inside me, but he still wanted me to be very tight. With that, he removed his fingers and shifted his weight.
He placed his hands on my lower back, and pushed down…supporting most of his weight with them. I then felt his dick begin to slide around my smooth crack. It brushed against my hole for a second, but quickly slid past. Then, suddenly he slammed his bodyweight down onto me. My heart fluttered before I realized he had not penetrated me. He did this several more times…teasing me until I said it. “Please…just fuck me…please…”
I could almost sense his smile. He removed one hand from my back and positioned his cock right against my virgin hole. I felt the pressure and began doubting whether I could take it…he was about 2 and a half fingers on top of 2 and a half fingers thick. I pushed back and felt him slide in. He took his time as he slowly worked it deeper into me…stopping when I would take a deep breath in. I would definitely feel pain each time he pushed a bit deeper…almost like there was nowhere else it could go…like he was pushing against something inside me…but, as he slowly worked it in, the pain lessened. I was a little shocked as I felt his balls touch my cheeks. It wasn’t nearly as bad as I thought it would be.
What I felt most of all was complete fullness. Its hard to explain, but it felt like he had filled my ass as much as it could take, and it tingled…in a good way. Just having him inside me felt good, and he wasn’t moving or anything. Then…he did move. He started to slide himself out, still going slowly…until he was about half-way out, then he pushed in, a bit faster this time. I moaned real loud to let him know that I was feeling good, and he could start to use me how we had talked about.
With that, I felt his hands move to either sides of my shoulders, as he hovered over me. As he started to withdraw his cock again, the only part of us touching was his knees forcing mine apart, and his dick inside me…As only the tip of his dick remained inside of me, he came crashing down again. Now, this did in fact hurt a bit. I think when he did this, it pushed him deeper into me than he was before. Unfortunately, from the position I was in (stomach flat on the bed…arms secured behind my back), I couldn’t move…let alone pull away. He ground his hips into me aggressively…keeping himself in a bit deeper than I was comfortable with. I think I probably would have said something at this point, but I didn’t have a breath in my body. His initial slam had knocked the air out of me and I was struggling to regain it.
He began withdrawing again as I trembled a bit in fear…wondering if this was going to get out of hand. He crashed down into me again, but did not take the time to grind this time…instead choosing to withdraw immediately and slam into me again. When doing this, I would only feel a twinge of pain when he was fully inside of me…but he was withdrawing so fast, it was quickly replaced by the great feeling of the fucking. I was continuously feeling the extreme pleasure of the fucking, followed by the slight twinge of pain of the penetration every time he reached his deepest inside of me.
He was really giving it to me. All I could hear was the incredibly loud smacking of his thighs against my ass as he plowed into me from directly above. He removed one hand from my side every so often to spank my ass…a little harder than I probably would have preferred, but I was in no place to argue. The pain of the fucking was not subsiding, but neither was the pleasure…I think between the pleasure of the fucking, the idea that I had no control over anything that was happening, and the fact that I was finally living out my fantasy…my mind began to accept the pain as payment for all the pleasure. Hell, I was willing to take it as long as he could give it.
Speaking of that, he had been plowing my now non-virgin ass for a good ten minutes before giving signs of slowing down. He started to finish each thrust with a very rough/aggressive grind into me, which extended the pain of each penetration. He also started taunting me during the grind, before slamming another thrust into me….
*grind* (me squirming in pain)
“You’re a dirty ass-slut aren’t ya?”
*grind* (me squirming in pain)
“You want to be my personal ass-whore don’t ya?”
This repeated for a couple minutes before a final slam and grind was followed by a loud incessant moan rather than a taunt. I could feel his dick spasming inside me as I assume he dropped a huge load. He spanked me harder than ever before withdrawing completely from my used and abused hole.
My mind was racing as my breath finally began to recover from its almost 20 minute hiatus. I heard him get up and dispose of his condom before returning to me. I had expected him to get dressed, unlock me, and head out like we had discussed. Instead, he sad down next to me, and asked me how I liked it. Ashamed, I admitted that it was incredible. He then asked if I was interested in going for another round. Stunned, but still very much turned on, I agreed.
He then told me that he had some stuff in the bathroom that he wanted me to put on while he recuperated. He unlocked the cuffs and I quickly scurried toward the bathroom, shutting the door once inside. I was stunned and very excited to see what was waiting for me…