As a big fellow I don't have the pulling power that some other chaps have, I have to revert to calling in or picking up prostitutes. It hurts me even when the ladies of the night turn there nose up at me. So I jacked that in. So the last few years have been self abuse, I have amassed a collection of toys for my pleasure.. Tenga Eggs, Fleshlights and even the rubber arse and pussy moulds you can get from Anne Summers. But doesn't even come close to human to human contact. I needed that again but something different. I don't know what it was that triggered my feelings for a man, as I don't find men attractive or feel the need to be in there company. I started watching TS porn, was really getting into it, there are some beautiful TS's about and I was cumming hard and fast, this was new and exciting. It opened up many doors in my mind, there is more to sex then a man and a woman and on from there I was watching full gay porn, taking particular interest in "Casual Encounters" "Grindr hook ups". This was amazingly hot, total anonymity. The thought of someone pleasuring me and leaving. No kissing, no chit chat and no let downs, just pure pleasure. I couldn't get enough of this, watching porn and reading stories. I was masturbating any chance I had at home, at work, even at the football in the toilets. What surprised me most is I wanted to be fucked, I wanted to receive the strangers cock, I wanted my hole to be left in a spunky mess. Considering I've never even had a finger up my arse I think it's strange that I would want that done to me. Maybe it's my Sub nature. I started to experiment with my hole, spending more money online buying anal trainers, lube, duches, butt plugs. I spent a fortune but I didn't care. The ejaculations were immense, I have never been a heavy cummer but I was spewing cum without even touching my cock. My collection of toys were impressive but I knew what I needed. It was a Friday night, got back from the pub early was a bit tipsy but horny as hell, as most are after a few drinks. Opened up my laptop and glanced through my favourite videos. I found the one I wanted. My mind was ticking, the booze gave me extra courage. I turned off the porn and got onto Craglist.. Looked at some of the adverts, I had butterflies, I was so excited but so horny. I posted an advert, it went something like.... "Heavy Virgin seeking no strings stranger cock!" Sounds terrible but it had the desired effect. I had an email after an hour, was just about to give up when the phone went off. I exchanged a few emails. I told him the situation, I said I will be in my room, naked, bent over my bed waiting.. No foreplay, just straight anal penetration. I gave him my stats so he knows what to expect, his reply was.. "I don't care." I took that as a compliment. So I rushed around cleaned my room, showered, washed my hole with the dueche. I was so nervous, I almost emailed him not to come over but I knew I had to do this. I left the door on the latch, went upstairs to my room, threw some condoms on my bed, a towel and the lube. I didn't ask this guy how big it was so I quickly rubbed some lube into my hole. I stood patiently, then I heard the door open, my god, my heart was racing, the door slammed, I heard him come up the stairs, I took up my position on the bed, I kneeled down at the end then bent over, I was facing the mirror so I could see it all. Then he creeped into view. Not a word said, he was about 6ft, White, average build, couldn't see his face. He stripped naked. He was playing with his cock, I gulped as it was quite a size on a semi, he said "I'm gonna go easy.. Do you want me to wear a johnny?" I replied "it's up to you." He said "Bareback it is." He grabbed the lube, poured a bit into his hand, rubbed onto his big cock, at this point it was fully erect. Then he rubbed his fingers into my hole, I was hoping he was going to finger me to get me ready for his huge member but no such luck. He spread my cheeks and rubbed his cock on my hole, nervousness turned to excitement, my cock was so hard and was going to cum at any second, he has hardly touched me and I'm already on the edge. The rubbing turned to prodding, felt amazing. He said, "if it hurts, just say." I nodded. It put me at ease, it relaxes me as I felt the first few inches, it didn't feel like any of my toys, the size, the heat... Then a few more inches, it started to feel uncomfortable but I rode the pain, he was getting into his stride, within no time he was balls deep, the pain was subsiding and was starting to reap the benefits. I started to moan, I could feel I was about to cum, I was trying to hold back but I couldn't he was going faster, in a rhythm, his balls slapping, grabbing of my shoulders, he was squeezing and I was cumming, uncontrollably, my hole was contracting with him inside of me.. He was loving it, he was moaning now then he quickened again, he said "where do you want it?" And I replied "in me!" So the pace was fast, he was starting to grunt, then I felt it, I cannot describe the feeling of a man ejaculating inside of me but it has to be second to cumming. We were both breathing heavy. I could feel his cock shrinking inside of me. He pulled out, got dressed an he was out of there. I laid there for about 20 minutes after he left, the cum was dropping out of my hole and onto my balls. I was in shock I think, I couldn't believe I done it. After I cleaned myself up and had a drink.. I was already planning my next encounter.