My first time having gay sex

I want to tell you all the story of my first and only time having gay sex. My situation: I am a 20 yr old boy who has a wonderful girlfriend and have been with her for 2 and a half years. I love her very much but I have always had thought about "what it would be like to try the other side". Ever since I started ************ when I was 12 every so often, maybe once a month I have fantasised about seeing a man naked. When I started watching **** it was nearly always women who I would look at, but just that odd occasion I would look at men doing it. It was mainly curiosity more than anything else.

Anyway, back in November last year I found a website for meeting other people for sex and or relationships. At first I just window shopped at the women. There always something really exciting and sexy about seeing pictures of women in erotic poses who live in your area. After a while I started looking at the photos of men and transexuals. The transexuals turned me on (well, some of them) because they genuinely looked like women. I looked at some of the men and read their profiles. One of them was a 52 year old man who's profile read "divorced man looking for discreet sex with younger men". I thought to myself for a moment "what if I was to explain to him I am bi-curious and looking for my first time".

This got me very excited, especially since I hadn't even planned to try such a daring thing. I sent him a quick message telling him my situation, that I had a gf but I was curious to see and feel what gay sex is like. He reassured me he was very discreet and understood my situation. He hadn't long started exploring other men. Now most of you will think 'why go with an old man' but the thing is there's something reassuring about an older man. Younger men are more open about their sexuality, I was only curious and didnt want my name spread around the gay hotspots around town.

We arranged for me to go to his house late at night. When I got there his house was in a row of 5 houses, his being slap bang in the middle. His front garden was overgrown though and it was dark so I was pretty confident no one would see me enter. I sent him a quick text to say I was in my car waiting outside. Without turning any outdoor lights or front hall lights on he opened his door. He was a tall, slim built man with short greying hair and minimalist frame glasses. He got out my car and walked into his house.

When I got it we introduced our selves and sat down in his front room. He asked about my bi-curious state, wondering why I was wanting to try gay sex. I told him how it's something I've thought about before but never taken seriously enough to explore until now. He then went on to say he likes a clean boy. I slightly blushed when I told him I hadn't had a shower since morning time before work. He said "that's not a problem. Let's go upstairs and have a quick wash." He lead me upstairs and firstly into his bedroom. It had a low-down double bed with no covers on it, a wardrobe and bed side cabinets either side of his bed. The room was lit by a single lamp in the far corner giving off a warm, yellow glow. He started to undress and I followed suit. All the excitement made me rock hard in seconds. We both stood facing each other, looking at one anothers completely naked body.

His penis was soft, but huge. I was embarrassed at the fact I had hard on before we had done a thing. He didn't seem bothered at all. He lead me through to the bathroom and turned on the shower. I stepped in and started to get soaking wet. What I was feeling at the moment was unbelievable. This man was looking at my hard d**k and naked body whilst I showered. He quickly joined me and we started to explore each others bodies. He made the first move and grabbed my throbbing c**k. I then grab his. Feeling another mans penis felt odd, but nice. He was still pretty soft. As he grabbed my penis with one hand his other hand went between my legs and between my bum cheeks. He started rubbing my arsehole. I felt so relaxed and happily let him explore. I then done something I never imagined doing. I got down on my knees, right infront of his penis and put it in my mouth. It felt unbelievable.

I was the one giving the pleasure, yet I was also feeling the pleasure. It wasn't in my mouth for long but I made sure to get my tounge all over it. I could have done it all day. He turned the shower off and he gave me a towel. Once we dried ourselves we went back through to the bedroom. I was probably the hardest I've ever been at this point. He lay on the bed, on his back and invited me over. He asked me to lie on top of him. He started cuddling me but I wasn't it to that sort of thing (weird huh). He then went to kiss me but I said I wasn't sure if I wanted to. For some reason hugging and kissing another man doesn't turn me on in the slightest. I lay on my stomach and he started to touch my body up and down, spreading my bum cheeks with the fingers on one hand, leaving a finger free to rub my anus. Then, all of a sudden, I felt his face pressed up against my a*s. He was licking my hole! I let out a loud groan of sexual pleasure. After that he went over to the bed side cabinet and took out a d*ldo. He asked if I wanted to try it. In my excited state I said "oohh yes please". I stayed lying on my front as he slowly worked the d*ldo way into my a*s.

Slowly but surely, after very very little thrusts, it went in nice and deep, with only a small part of the base not inside me. All this time I was moaning softly with pleasure. He then removed the d*ldo. I knew what was coming next and I couldn't wait! I pulled on a condom and positioned himself on top of me, and arm either side of me prolong himself up. He worked his c**k between my bum and slowly but surely started to push the tip of his penis against my anus. After a but of work my anus started to open up. Once this happened he pushed a little harder. By this time things were starting to get a bit sore. All of a sudden, with what felt like my anus muscle spazzuming, he pushed his d**k right in, so much so that I felt the front of his thighs press against my arse cheeks. The pain was intense, but the excitement over ruled this. I could feel what I presume was my prostate being massaged as he thrust in and out.

I was rubbing my d**k, feeling a sensation I had never felt before. After some more thrusting he took him penis out my anus and took the condom off. He must have been a seasoned pro at this because he hadn't came any. He spun me round on my front, and with both his arms he put them under my legs and lifted them into the air. He rested a leg on each arm so he could keep my legs in the air and started to suck my senseless. The whole time he sucked me he looked into my eyes. I was ready to explode! I was able to hold of just a little bit longer. He stopped sucking and started tossing me off, resting his c**k on my anus. I loved this and told him so. He started to w**k me faster and faster until finally, in the most pleasurable moment of my life, I shot my load everywhere! It was weird, because what had just been the most sensational moment I had ever felt lead to me feeling uncomfortable. All in the blink of an eye. I felt like I had done something I deep down, didn't want to try, but let my sexual arousal decided at the time. We got changed and said our goodbyes.

I haven't had gay sex since and I don't think I will, at least not for a long time. When I think back to it I don't regret doing it because it helped me decided what I am. I am in no way emotionally attracted to men, heck, I don't even recognise what most people would consider 'a good body' on a man. A woman I do. I could never be in a relationship with a man because I just wouldn't feel right. Like I said earlier, I don't like the idea of kissing and cuddling, Its not me. I am however, bi-sexual to a point, only sexual encounters, and I'm happy to accept that. But I'm not thriving to have another gay sex experience any time soon. I hope you have enjoyed my story. This is the first time I have ever told it.