Technically speaking, that title is wrong. This is not an account of when I lost my virginity to another man but it's the tale of the first time I had real sex with someone of the same sex as me.
If I am going to be brutally honest, my first gay experience happened at boarding school when I was no more than 9 or 10. A friend (a couple of years older than I was) and I would secrete ourselves in the toilets in the changing rooms when nobody was around and we would fondle and suck each other. We never got round to full sex as neither of us really wanted to. I wasn't even capable of ejaculation at that age and it really it meant nothing to me.
Since that time I grew up, I became sexually aware, I lost my virginity to a girl the same age as I at the age of 15 and I was fascinated by anal sex. I would spend ages with a dildo in my butt even while I was going out with the first love of my life and we would have sex whenever we could. But this never stopped me from sticking a dildo inside me.
Fast forward 3 or so years to after I had moved out of home and into the local YMCA. I got friendly with a known gay guy called Johann. We were in my room at the YM talking and the conversation got around to gay sex, I confessed that I had always fantasised about it and wanted to know what it really felt like to have a cock inside me, fucking me, cumming in me. Needless to say he agreed to show me the "ins and outs" so to speak.
I lay down on the bed face down and he took up position behind me. Please bear in mind that I had been practicing with a dildo for about 3 years so I was no stranger to having something in my arse, I knew how to make things fit, I knew the techniques to make it easier and I knew that I shouldn't have done it without lube but I was too horny to stop.
He spat on my arse in an effort to make things slightly easier. After lubricating his cock I felt him push it inside which hurt a little but that was down to a lack of lube more than anything else.
His 7 inch cock was firmly embedded in my ass as he started his thrusting into me. This wasn't exactly what I was expecting but it was what I wanted. I was enjoying it as my cock was being forced onto the bed but I knew I wouldn't cum like this.
After about 10 minutes I felt his cock spasm as he pumped his seed into me and he collapsed on top of me.
Up until now I had no concept of either top or bottom as I fancied myself as both. This was when I learned the crucial difference as when I tried to fuck him I couldn't insert my cock into his ass because he was so tight.
We gave up that idea and he went our separate ways after he fucked me again and deposited another load of cum to join the first.
I was left feeling vaguely disappointed not having fucked him in return, however I was enjoying the feeling of his double load of cum trickle out of my ass. I scooped some up on my fingers, rubbed it over my cock and jerked off until I came.
As I said at the beginning however, this story is not about that encounter but the encounter that I regard as the first true man on man sex I had.
I was 30, married to a wonderful woman whom I still love dearly; the only problem is her sex drive which I'm afraid to say is considerably less than mine. The good news is that she knew it was less than mine and did allow me to play away from home when I felt like it as long as I abided by a few simple rules.
The arrangement worked for both of us, I got to have sex, she got to have first dibs and if she didn't want to, fair enough.
She had gone away for a few days to a friend's house in another county and I was home alone and free to play. I'd had a profile on a popular gay dating website for quite some time but never met anyone from it; I suppose I was still getting over my nerves.
That evening I started talking to a guy who was regular and wanted to know if I could come over for some fun. It took an hour of persuading but I finally relented and arranged to meet him at his place. I took a quick shower, checked myself over in the mirror to see if there were any outside hints of madness and left.
10 minutes later I pulled up outside his house, knocked and was let in. He would have been in his late 30's, quite tall and slightly attractive. He offered me a drink and we sat and chatted. We spoke about my experience and he was a little disgusted at the way I was treated. He put down my reticence to my past experience.
We chatted for hours and it was by mutual agreement that we wouldn't head upstairs for this `fun' we had planned, mostly because of my nervousness. I left at gone 2AM having spent a good 4 hours there and not once had I even unzipped my fly. We did however agree that I would come over the next day a little earlier and see where we went from there.
I was very unsure all through the day if I could go ahead with the plan but sure enough I turned up at 8 o'clock having showered again with a semi hard-on.
He answered the door in tracksuit bottoms, a T shirt and slippers. I could see that he too was sporting something in his trousers as they tented considerably. We sat together on the same couch (previously we sat apart) he with his legs spread apart a bit and me with mine straight out. We chatted for a while and all the time I was conscious of the hard on in his trousers just inches away from my hand. He put his hand on my thigh and I suddenly realised in horror that my hard on was now completely gone.
When I have an erection, it measures 8 inches long and apparently is nice and thick. When I don't however you can almost fit it into a thimble it's that small. I didn't want him to think I was challenged in that department but my rising panic didn't help matters so to take his mind of it (at least that's what I told myself) I placed my hand directly on his hard cock and started stroking. He felt big, very solid and it was quite strange looking back at it, sat on this couch stroking a stranger's cock through his trousers and wondering what to do next.
That decision at least was taken out of my hands. After stroking his cock for a few minutes he hoisted his arse into the air and pulled his trousers down and his long cock popped out. It was about 9 inches in length but thinner than mine. I knew it was longer than the largest dildo I had experimented with but I was willing to give it a try. I continued to stroke it for a while, feeling the velvet texture of his skin as I repeatedly pulled his foreskin back and forth over the knob.
He asked if I wanted to go upstairs and after a moment's hesitation I agreed. On entering the bedroom I gawped at the bed, it was a huge double with a brass head and foot board and looked large enough to have an entire orgy on let alone just the 2 of us. We both undressed, even though I still had a distressing lack of hard on and I crawled onto the bed to join him. Not knowing what to do I resumed my stroking of his cock, running my fingers down to cradle his ball sack. I felt his hand on the back of my head bidding me to suck him. It wasn't as bad as I thought it would be there was just the sensation of warmth and size. I must have been doing something right however because he started moaning and moving his cock in my mouth. There was no chance that I was going to be able to take all of his cock as I wouldn't perfect my deep throating technique until much later in life.
As I was lying there sucking this cock he reached around and started playing with my ass trying to insert a finger into my hole. At this point I was still quite tight but I knew the techniques required to take his finger and cock if I had sufficient lubrication. He seemed to either read my mind or he figured it out for himself as I soon felt the cool dampness of a plentiful supply of lube being spread all around my puckered entrance.
After that his finger slipped into me almost easily and I was glad I had cleaned myself out before coming. Soon I was writhing and pushing back onto him as he entered me with a second, the whole situation was turning me on like mad.
After a few more minutes of sucking and fingering I knew I had to sit on his cock so I pulled my ass off his fingers and positioned myself over his hard on. He asked me if I was ready to take him and I mumbled that if I didn't do it now I probably wouldn't do it ever. Saying that I started to lower myself onto him slowly, feeling my hole stretch open to accommodate his hard cock and when the head had entered me I slowly sank onto his cock until I felt it hit the back of my ass and I knew there was more to come.
I started riding his member clumsily and was generally making a complete hash of things but he was apparently enjoying himself as he started to push up into me. I could feel more and more of his cock entering me but all the time knowing that I still hadn't managed to take all of it yet.
This carried on for maybe 10 minutes until he sat up, gently pushed me onto my back and climbed on top of me, my legs bent and spread as he nestled between them. Now he started pushing into me with slightly more earnest and I felt him bottom out inside me, occasionally causing me to wince in pain as his cock hit the back of my rectum forcing it to lengthen.
He did notice my pain so he tried to keep it shallow and settled into a nice fucking rhythm. Slowly but surely more and more of his cock was sliding into my arse and I was loving every millimetre of it. I was surprised to realise that I could now feel his balls against my arse as they swung and slapped me, the pushing of his crotch was forcing me up the bed and I just lay there and took it. He told me to spread my ass cheeks apart which I did on one of his out strokes and when he came back in it was deeper than he had ever been before. His moans were echoed by mine as he started hammering my ass, his voice going hoarse and just at the point of his climax he withdrew and sprayed his cum all over my hole and balls.
He fell sideways to recover and I couldn't help touching myself, feeling his gism coat me and sliding 2 fingers straight inside me. I had never felt so open before and my ass was feeling extremely used but I was all too ready for more. As he was lying on his side I noticed that he cock did get softer, but not that much. It was still at least 8 inches in length and lost none of his girth. By now mine was rock hard and standing as proud as it had ever done so I contented myself with playing with my dick with one hand whilst finger fucking my man pussy with the other.
By this time he had noticed that I was up and eager for more so was he and he turned onto his side. I flipped over so my back was facing him and lifted my leg for him to gain access to my hole again. I couldn't believe that his cock was hard enough again to fuck me after such a short period of time but he positioned himself behind me, held his cock to my hole and pushed it inside all the way to the hilt in one fluid movement. Again my education was continued as his cock ravaged my hole.
I pushed back onto him in time with his thrusts, pushing my ass out to him. This time there was no problem with depth as he frequently went from only the tip in me to fully encasing himself in my flesh time after time after time. At some point he rolled me over so that I was face down on the bed, my ass being pummelled and my cock mashed into the sheets. Again I pulled my ass cheeks apart so he could get deeper which he appreciated. Since he had already cum once I wasn't expecting him to do it again (I cum once but it's generally huge when I do) so when he picked me up onto my knees, told me to hold onto the footboard and hang on I did just that.
The hammering I had received before now paled into insignificance compared to the onslaught my ass took, I was holding onto the brass for grim death and shoving my ass back against him, his cock would slip out of me completely only to be slammed back in a fraction of a second later, never missing its mark and always ending up right inside my pussy. I have never cum from anal sex before or since but that was the closest I ever got. I kept telling him to "cum in my ass, I wanted to feel his cum in me, breed me, I want it" over and over until I felt his cock swell within me, I heard him grunt and his cock slam back into me only to stay there as he dumped his seed into my hole.
I felt him jerk over and over as his cock emptied itself into me. We both collapsed onto the bed spent him empty and me full. At this point I still hadn't cum but my cock was limper than previously probably from all the action my ass was getting, and it was sore but it felt so wonderful. I could feel his cum trickle out of me as his dick started to shrink until it was too small to be held by my hole and the extra lube from his balls only exacerbated the situation.
After we had calmed down I mentioned that I needed to cum and I'd really like to do it with him in my ass, something that he was only too happy to oblige me with.
Once he was hard enough again I lay on my back and lifted my legs, he lay on his side with his cock back to my pussy and simply eased it inside me. I was already playing with my cock so I reached down with my other hand and felt my ass where his manhood was planted. I could feel my ass grip him as he pulled out as well as it cave in as he slid back inside me. I started pushing back at him, pumping my cock and squeezing my ass around his tool and we were soon going at it again like demented rabbits. I found that if I lifted my ass a fraction as he pushed inside me his cock would rub over my prostate gland causing electric shocks to course through my body. All this, his cock in me, my prostate and my hand wanking myself off had me to the brink or orgasm when I recognised the tell tale signs of his approaching point of no return too.
I tried to hold off but it was too late. I arched my back high at just the right point for his cock to hit my G spot right on the button and it was all over. I shot my cum high into the air for it to land onto my chest, great gobs of my cream gushed from me and I furiously wanked myself off. The net thing I knew was him clamouring to get deeper, my ass had clamped down onto his cock with my cumming that it had set him off too and he was slamming my ass whilst holding me tight in the throes of cumming as he shot the second load of cum my arse had in it that evening.
When we were both fit enough to move I looked over at the clock. The time was past midnight and I estimated that we had been fucking for about 3 hours at least. My ass was dripping cum, my chest was covered and both of us were soaked in sweat.
We showered together, he tenderly washed my ass and I washed his cock. We both dried ourselves and I announced that I had to go. He originally wanted me to stay the night but I couldn't as there was no-one to look after the animals as my wife was not there to do it in my absence.
We parted on the doorstep and promised to keep in touch. As I got into the car I knew then I was no longer a virgin and I could still feel his cum inside me.
That is how I had sex for the first time, sex is something more than a quick fumble and a shoot, its more than one person getting pleasure by dumping cum in someone else's ass ... sex is about 2 people giving each other pleasure, it's a mutual thing, it's a beautiful thing and it's something you look back on and say "Yes I'd do that again!"
As I said at the beginning, this is a true story recollected to the best of my knowledge. I have deliberately not given my name, nor the names or places of any participants for very good reasons.
I have published another story on here before and I will do so again soon so if you want to read more, please feel free to email yoric27@hotmail.com
p.s. needless to say, this work is licensed to me