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By (user no longer on site) OP
over a year ago
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I was 18 when I first had sexual contact with another man, this is the true story of how that happened.
Up to that point although i'd had the odd gay sex fantasy I considered myself straight but on a holiday to Torquay that was all to change and then some. Having got separated from my group of friends I found myself lost wandering the streets around midnight. I stopped two guys, around late 40's early 50's to ask directions.
One a balding slim shortish well spoken guy, bid goodbye to the other guy and then he said he was going my way and would point me in the right direction as it was near where he lived. I really should have suspected something when the other man winked and sloped off as Roy introduced himself and we struck up a conversation.
After the usual why when who he asked if I had a girlfriend (I had) and told me he was 55 and separated from his wife as he had just spent two years in prison for fraud and had lost his business and home and was now picking up the pieces of his life. I asked how prison was and his reply started to reveal his true intentions towards me.
He said at the start the thing he most missed was contact with women especially his wife as he had always had a healthy sex drive. However it was wasn't long before he discovered sex with other men was just as good if not better at times than with women and he was now a confirmed bisexual and a phrase that stuck with me, "Your body's your body Mark and theres plenty of more ways to have fun than just women". It was now clear where this was heading but did I have the guts to let it continue, while wanting to instigate something now with a stranger who I would probably never meet again I was unsure how to handle the situation so just mumbled "Well each to their own i guess?" and continued walking.
Then to my suprise and somewhat disappointment I then turned into the street I was staying but by now I didn't want to go home as my latent bi feelings wanted to let this guy know I was interested and available if he wanted me. My sane side won out though and i said thanks i'm home now and turned to walk away damning myself for not having the guts to make my first gay sexual contact, something remember I had fantasised about and here was it was as a reality if I had the courage. I might never get the change again so could have kicked myself as i walked away. Luckily Roy wasn't giving up that easily.
He called after me then said "Mark, you're a real nice lad, I don't want to pressure you but i've taken a real liking to you and wanted to know if I could take you somewhere to have some fun, may you will let me wank or suck you off" Boom! A man wanted me for sex, I was up for it of course, my cock already hard from the anticipation so I readily agreed to let him suck my cock (still being a virgin i'd only ever been wanked off by girls before) but asked where we could go.
He led me to a small park a few hundred yards away then into some bushes. Still lit by streetlight i could clearly watch him as he undid my belt unzipped me then pulled my trousers and pants to my knees. He was now on his knees as he released his own now rigid cock commenting to me not to worry it was for him to wank himself while my cock was in his mouth he wouldn't make me do anything I didn't want too.
I was apprehensive never having done this before but was soon at ease as he pulled back my foreskin and slowly licked the head of my cock putting his tongue in the slit as he passed. After a minute or so he took it full in the mouth while he rhythmicly ran his hand both up my shaft and his own in time every now and them kissing my balls too. He'd stop every few minutes and comment what a nice cock i had for a young lad and on more then one occasion asking me how old i was, I now realise me being young was a major turn on for him, he being a fiftyish guy me a slim athletic good looking lad not yet 20. He was not alone, the major turn on for me was seeing my younger cock in an older mans mouth as he wanked himself below moaning with the pleasure of it all.
This lasted for around ten minutes but whether it was latent guilt or a little too much to drink, and although my cock was so hard it ached, i just couldn't come. I mentioned we might try something else, i had no idea what but when Roy stood up nature took over. There in front of me was an erect cock maybe around seven or eight inches long not as thick as mine slightly tapered but i wanted it. I asked Roy can I, he replied "Oh yes Mark, do what you want with it" so i reached out to hold my first hard adult erect cock. I slid my hands down the shaft to cup his balls, he gasped as i squeezed them. I took hold of my own cock and rubbed it all over his cock and balls, I could feel him getting harder and harder.
Then something deep inside me triggered and I knew what i had to do. I was quickly on my knees with Roys cock in my mouth and it only took a few strokes before i felt him shudder and I was tasted his thick spunk as it spurted into my mouth. Did I swallow, you bet i did then stood as Roy kissed me full on the mouth to taste himself while his hands wandered back down to my still aching cock to rub over his spunk covered dick.
I still knew i was nowhere near coming but did not want the night to stop so asked if there was anywhere else we could go. He said no pressure but theres a big bed at my place. A short walk later we were at a beachside apartment naked in his bed doing what guys do to each other. I was not ready to try anal sex, at least not yet, but we had long hot mutual fun long into the night and when i did finally come it was an orgasm like never before, him wanking me hard while his cock was in my mouth once more. I was hooked.
Although somewhat sheepish when i woke sober the next morning Roys open bathrobe as he brought me coffee soon had the mutual sucking and wanking starting again and i returned on subsequent nights to learn more technique from my experienced teacher, even to take part in a threesome with Graham the man who had been with Roy on that first night and who it turned out was Roys fuck buddie. They told me they'd often pick up other guys on holiday, inhibitions go out the window when you are away from home. This was one inhibition I didn't want to leave on vacation so on returning home I sought to find other like minded men to repeat the experience and more. Much to my suprise it was easier than I thought and it wasn't long before i engaged in other acts with various men of all ages. Roy gave me number and I met him a couple of times in London hotels over the next few years but we lost contact after he finally got back with his wife.
It took me a couple of years before i had the courage to combine my crossdressing, which I'd been doing in private for a few years, with sexual contact with others, and that only by accident, but that's a story for another day. Sometimes though I still like to go out in my male persona to enjoy what happened on that first night, man to man, cock to cock.
So Roy if you are still out there thanks, you taught me that sex between men is enjoyable and fun and i'm still practising what you taught me and loving it.
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