He wasn't the first to have taken my anal cherry. That particular honour, if it was an honour to him, was a bully in my high school. I was fifteen at the time, and was walking home after having a fight with another student. He'd been putting out rumours of me sucking off an older student, which I'd denied calling him a faggot wanna be. He'd attacked me, but surprisingly I won the fight.
The short cut wasn't one I normally took, but I didn't want the older brothers of the guy who I'd fought with, to find me and beat me up. If I'd known what would happen, I might not have taken that short cut.
Brian was waiting along the track I was on. He later told me he'd cut across the field to be in front of me. It was a hot afternoon and I was sore from punches which had landed in my ribs and face. When I rounded the bend in the track, I saw him stood there with his cock out. There was no where to run and I couldn't have out run him knowing who he was.
I walked the ten or so paces upto him and tried to skirt around him. But Brian told me to stop and to attend to him.
His dick wasn't fully erect, but I knew it would get very big, because Brian was the older student who I'd sucked off before.
His cock felt that familiar in my mouth, I instantly began to take it as far as I could, after I'd suck to my knees. Brian wanted me to give him head, because he said it had turned him watching me beat another student up. The two years age difference wasn't the only difference. Brians physical stature was larger than mine and his sexual development had very much surpassed mine too. His nine inch cock was the first cock I'd sucked and it is still the largest cock I've sucked or been fucked by.
He was fully hard by the time he told me he was going to fuck me. I was scared and not a willing partner at first. Pushing me over, he climbed onto me, removed my clothing fully (I didn't struggle too much) and had me kneel up. In the four months I'd been sucking his cock after school, he'd not once shown any kind of feelings towards me, only a sexual lust to have me swallow his cum. So it was strange to feel his mouth on my asshole, and his tongue lapping away at my rear. Without meaning to, I became erect and Brian saw it. He asked me if I was a faggot. The smile I gave him and my words only resulted in me getting a punch to the ribs that were already sore. My grunt seemed to spur him on and without any warning, Brian thrust his cock hard into my asshole.
It was the worst pain I'd ever felt, but Brian held onto me as I tried to move away and then I felt him thrust into me again, going deeper inside my body. The pain didn't stop, but it didn't worsen either. Holding me tightly as he leant over my back, Brian said "I'm going to fuck you now, so enjoy it boy". I'll never know if it was his words or just the fact my body had become semi accustomed to his huge cock, but as he began to fuck me, my senses began to focus on the warm pleasurable feeling that had started in my ass and my cock. Before I knew it, I was backing onto his dick and Brian had started to hammer my asshole. A couple of minutes later it was all over. Brian unloaded up my ass and I was left on the floor as he withdrew from my ass, got himself together and stood up. There was no glorifying orgasm on my part as he didn't fuck me long enough, but I didn't know that then. When he'd told me to keep our liason to ourselves and I knew Brian had gone, I took hold of my six and half inch hard cock and masturbated until I came all over the dirt track.
That was the last time I took his cock in my asshole, although I did suck his cock on and off for another few months until he and his family moved to a new city.
My life moved on, as did my sexual tastes. And I soon discovered the delights of girls, their breasts and their beautiful pussies. My cock had grown to it's now full seven and half inches and I soon learnt how to use it to pleasure girls and latterly women.
I married last spring to a beautiful person. She's a very good looking woman, who totally floats my boat. Sexually we're very good together and we have sex at least three times a week, depending on work commitments. It is those work commitments which have lead to my second gay experience and the fulfillment of something I knew was missing in my life.
Steve is a manager of a company which supplies the company I work for. He's married like me, and also like me he'd had a fight when he was a young teenager. The reason he'd had the fight was to remove any doubt with his peers that he might be gay or bisexual. He did that by attacking me.
At our offices he came in and spoke to me as I was the only person left. We remenissed about our stupid fight and he confessed he'd only attacked me to fend of suggestions he might be bisexual. When I asked him if he was, he said "So you think Brian only had your mouth to fuck". We talked about Brian, our schooling and then I told him about what had happened the day we'd fought. There was no build up to our kiss, it just kind of happened, then knowing the offices were empty, I lead Steve upto our senior managers office and onto his leather couch.
A whole new chapter in my life opened up, as did my asshole for Steve's seven and half inch cock, a cock which looks remarkably like my own.
We've comntinued to see each other for sex and I now enjoy fully the pleasure of being fucked. I cum every time when he's fucking me and I know because we're both married and want to remain that way, it is going to last. My wife still means everything to me and I still love fucking her as often as work allows. It's just I now have the one thing that was missing in my life, and that's a guy I can have oral and anal sex with. And one who wants to have me pleasured too.

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