Please Fuc My Ass

Once I hit my late teens I knew I had to try cock at some point. When I was drunk I craved it, especially hung over. I wanted to be dominated and didn't put it together that I was a bottom. There were a few instances where I would watch gay porn and masturbate. This caused some intense cumshot orgasms.

My first attempt to play with another guy was organised over craigslist, which I always use to find hard cocks. I had the house I shared with my girlfriend to myself and the urge had finally gotten too much to withhold. A guy in his early twenties came around and I let him in. We sat down on the couch with some porn on but the nerves got the better of me. I had to ask him to leave. He understood and left but returned very quickly trying to persuade me just to have a mutual wank, I couldn't as my nerves were shot.

Between this first experience and my next was a few years. During those years I continued to masturbate and eventually turned to anal play. I was going down the path towards cock. There were plenty of times where I organised a meet on craigslist but couldn't go ahead with it, my heart would be beating so fast each time.

I loved looking at the hard cocks that guys sent me pictures of and taking pictures of my hard cock and tight ass sending them back. I used to masturbate on webcam to a gay chat room, this was so hot knowing I was being watched and sometimes told what to do.

My first anal experience with someone else was with a hooker. I always tried to think that I just wanted a girl with a strap on to fuck me not a real cock. I rocked up and asked for her to use a strap on on me. It was roughly 4-5inchs and it felt great finally having someone else controlling my anal pleasure.

I striped down and was lying on the bed looking up at a gigantic mirror on the roof, I thought this would be awesome to watch my self get fucked in. There was also a mirror at the end of the bed so I could watch myself get fucked like a slut.

The girl came into the room and put them on the strap on, I was excited and so horny. She lubed it up and got me to be on all fours facing the mirror. I could feel the cock rub up against my ass lubing my crack, I was pushing back, eager to be filled. When she finally stopped teasing my ass I felt the cock slide in. I loved it!. I immediately pushed back on it taking the whole lot, I had used toys this size before. She slowly started fucking me in and out of my ass. I could see myself in the mirror with her kneeling behind my ass fucking it.

She wasn't as dominant as I expected and I had to tell her to change positions, I rolled onto my back. She slide the cock back into my ass and I could watch it from the mirror above the bed. A big thrust in and I would moan, as she pulled out I would push towards it not wanting it to get away. I loved the feeling of the cock coming out of my ass and plunging all the way in. I was being fucked like a slut and it looked so hot. I was close to cumming!. I'd never cummed from anal play before but the sight of myself in the mirror getting fucked and not having any control over the big fast thrusts and the slow deep thrusts. I blew my load all over my stomach and she was surprised, she said she'd never made someone cum from a strapon before.

She showered me wanting to fuck again but I was wrecked, I couldn't please her and it wasn't what I paid for anyway, I had gotten my money's worth that day.

After this experience I just craved cock even more. The strap on that I was fucked with wasn't big enough, I wanted a cock that would be hard to take at first but fuck me like a slut once it got going.

Once again during the time between the strap on and my first real cock I continued to fuck myself with toys, even using my roommates toys and other items around the house. I have no idea how I was never caught!

I decided I needed to get this done, I booked a motel room so I would have privacy to organise guys coming over. I was able to get a couple to come over where I practiced sucking cock. It was awesome, I would be nervous but as soon as I started I got so horny. One of the guys had a great cock and I answered the door naked. I sat him down and started to pull out his cock immediately, getting right into it helps the nerves from building up. I started sucking his cock, slowly up and down with a lot of suction. I licked his knob and rubbed my mouth along the side of his hard cock. I was so horny that I had gotten this cock hard and now I was going to make it cum. I continued to suck it up and down until I started to taste pre-cum. I gagged, the taste was strong and I wasn't use to it. I sucked his cock putting as much into my mouth as possible one last time before taking it out and rubbing it until he blew his load.

I was too shy during these encounters to ask the guys to fuck my ass, thats what I really wanted. We would talk when organising it and I would always say I wanted to suck a cock hard and slid that into my ass but I never got it done.

Until later that night, a guy emailed me saying he wanted to fuck my tight ass but not show faces. I was up for anything by this point. I slipped some cards into the doors so they wouldn't lock and lubed up my ass and waited on the bed with my ass facing the door, wearing a little miniskirt I had found. The guy entered and started rubbing my ass, once again I pushed back just wanting a cock to enter it. Once I felt the cock against my ass I let out a moan, finally a real cock! He pushed inside my and it felt about 5inches long. I could easily take it from the lube. It felt awesome he was fucking my ass and I didn't even know who he was. It didn't last long until he pulled out and started rubbing my cock vigoursly. I didn't really enjoy it but he was determined to make me cum. I thought about the cock being in my ass again a slow pull out with a fast thrust in over and over until i was pushing back on a cock pounding in and out of my ass. Eventually I blew onto the bed and with this the unknown male rubbed his cock covering my ass with cum. He left and I felt like a slut and went to shower. The feeling during these encounters is so intense that afterwards I can't believe what I've done. This was the first time a real cock was in my ass but it only last a couple of minutes, not long enough to get a good rhythm or to stretch out my ass properly.

I couldn't keep going to motels so I decided to risk meeting up with a hard cock at home. My roommates were away but they could easily come back as they were very impulsive. I had been drinking and took some pictures of my ass sliding off chairs and the edge of the bed. It looked tight and fuckable. I was ready to replicate my last encounter so I mentioned that I would be ready on the bed as they walked in. I was able to get three people to come over one after the other. I was being used like a slut but once again each encounter fell short of my expectations.

I decided to use the services of a T-Gril. I found an add online and had the money to spare. This tranny was hot, and I thought she'd be nothing like the photos when she rocked up. I answered the door and she looked exactly like a girl. We sat on the couch making small talk and having a few drinks. I was nervous and didn't know how to start. She took control kissing me. This eased my nerves and my cock started to grow. She knew what I wanted from the text messages and she moved to the bedroom. Lying on her back she pulled out a cock easily bigger then mine. About 7.5 inches when hard and not much less then that when I started sucking it. I crawled onto the bed in between her legs and put the cock in my mouth. It tasted great and I could feel it start to get hard. I licked the front up to the knob and the sucked as much as I could. I was trying to take the whole cock in my mouth but it was too big. I kept sucking it before she stopped me and asked if I wanted to be fucked. Finally!. I rolled onto all fours and she tried to push her big cock into my ass. I had been fucking myself with a tiny butt plug all day and had the other cocks try to loosen me up but it wasn't working. She ended up going soft before she could push into my tight ass, still like it had never been fucked. She apoligised and said after she met some more clients she would come back and finish me off.

Later that night I went to the casino to meet my T-Girl, I thought this was a good idea at first because I had such fun the first time. Being out in public made me paranoid though and I wasn't very good company. She noticed this and suggested we go back to her place to have some fun. In the cab we started making out. We arrived at her place and went up to her room where she jumped on the bed and pulled out her cock. She ordered me to suck it. I once again took this cock into my mouth sucking it up and down and licking it everywhere I could. It felt great to be away from home doing this and I put all my cock sucking skills to work. I was moaning and so hard myself that it hurt.

She stopped me and told me to go on all fours again. Once again my ass was just too tight, however, she went to get lube. After putting lube on her hard cock she pushed right into my ass. I had never felt so full and immediately let out a groan. It finally was the cock I was after. She started fucking me slow and I was overcome with ecstasy that I couldn't even do anything except moan in pleasure. I've never been vocal during sex but this time I couldn't help it. As she started to pick up the pace I pushed back, I was moaning and begging for more. I told her to fuck my tight ass. This was a completely different side of me, I was being fucked so hard and I loved every bit of it. She would slow down and then fuck my ass so hard I could barely stay on my hands and knees.

She then rolled me over onto my back and slide her cock right into my ass. My eyes were rolling back in my head and all I could do was moan in pleasure. As her cock pushed in I moaned as it slipped out I begged for more. This was by far the best position, we then changed again and I tried riding a cock for the first time. I was so exhausted that I couldn't get a rhythm going and struggled to do it. This didn't last long before I was flat down on the bed with her ontop fucking my ass. I don't know if she blew in my ass or not because I was so overcome with pleasure I didn't know what was happening.

After she finished I still hadn't come and asked to fuck her but she declined. We fell asleep together before I woke up and left.

I haven't had my ass fucked since this experience but when I do I hope they can fuck me as well as the tranny.