Written by Flying Guy

Gay
15 Aug 2011


From number 9 I forgot to mention one last detail – when all was done she sprang up excitedly, saying “I did it” Like a child who’s just scored a point!

I should perhaps also confirm that the essence of every story is true, name s of course have been changed and of course I can't remember everything that was said each time word for word so I've "reconstructed" the sense of what was said but in the overall picture, everything is pretty much exactly as it happened.

Anyway – on to number 8 in my journey down memory lane. It’s funny, and enjoyable; how the process of writing each one intensifies my memory and brings back details that I had long forgotten. This next represents a very significant first for me. We jump forward in time some 15 years, I’ve been married, divorced and, if truth be known, still a little sorry for myself. It was an acrimonious parting and I was still feeling a little beaten up. I wasn’t sleeping well and was confident that I was pretty unattractive and no woman would be interested in me ever again. Hell, it’s a phase some guys go through after divorce. I now recognise it sounds pathetic – but then, at the time, I probably was… a little.

Another sleepless night saw me up with a cuppa and mooching around aimlessly on my PC. I didn’t know what I was doing but I was just killing time. The Internet was pretty new to me and I was just exploring, looking around different search engines and that’s how I discovered Internet chat. I clicked on a few different chat sites and must have created a hundred different identities in different places. But then I settled on one. I chatted to Bored housewives in Idaho, students in Canada and husband searching teens in Asia. I moved about as I became more familiar and settled on a UK area which had several rooms in it – some of them were geographic and others interest based. In my locality I chatted to a few people – mainly a few saddos like me unable to sleep. I made small talk with someone who I felt sure was a child pretending not to be so when the chat got fruity I moved on. Deciding what room to try next my eye was caught by a gay section, I clicked in out of curiosity. That long ago chance mention by a former lover had lived in my mind and occasionally surfaced in minor moments of fantasy. No harm in talking to a couple of gays I thought. Despite the fantasy thinking and the occasional sexy small talk that had turned on my wife the reality of sex with men was a long way from my thinking – in fact the idea vaguely repelled me on a conscious level.

It was a UK room and I got a lot of instant interest in instant messages asking what I was looking for and other questions I didn’t, then, understand. Once they realised I was less than a novice they soon left me alone. I chatted with a few less predatory people, and explained in the main room and in a few private messages that I was low key curious, sleepless, killing time and so on. Someone asked where everyone was from – most were somewhere in the UK but a few in the US, a couple in Canada, there was an expat in the far east and when it was my turn to name my town, another message appeared in the window saying “hey, me too”

The next thing I knew a private message opened up and we began to talk about where we were and it turned out we were just about 3 quarters of a mile apart.

“Do you fancy coming round for a drink? We’re both sleepless so we might as well keep each other company”

Panic surged in me and he said not to worry – he wasn’t planning to seduce me. So I saw my hands typing – OK.

I was given the address which I knew well and said I’d be there in about 30 mins.

It was not without trepidation that I rang the doorbell. But a youngish guy with cropped hair answered the door, he was wearing a dressing gown and he said, “Hi, come in”

I brushed past him, said thanks and he ushered me into a living room, shutting the door behind him.

“I’ve only got wine, white OK”

“Lovely, thanks”

He went into his kitchen and returned with a bottle and two glasses. It turned out he was a nice guy, we chatted about everything and anything and the wine helped me feel relaxed – whatever else was happening, this was better than being lonely at home and sleepless in bed.

He said that he had a mate who had recently been through divorce too and that he’d seen him feeling much as I did now. Just give it time was his advice – I would alter learn that he was right but, it was all new territory for me.

I must have dozed because the next thing I knew he was sitting on the arm of the chair beside me with a hand on my shoulder. “are you OK”?

I was of course embarrassed – how rude to fall asleep like that.

“Look, why don’t you have a shower, it will help wake you up and relax you a bit – the bathroom’s through there and I’ll open another bottle”

I was in a bit of a trance as I wandered obediently to the bathroom. “There’s a fresh towel on the third shelf” he called.

For some reason I didn’t lock the door but left it slightly ajar as I undressed and stepped into the hot powerful stream of water. He was right, it did make me feel a little better.

Feeling both cautious, nervous, slightly excited and extremely hopeless I wrapped the towel around me and went back to the front room, he was on the sofa with a new bottle on a small table beside him.

I made a decision at that moment. I would not start anything and I would not kiss him but I might not reject some other advance.

We chatted a little more and I felt myself relax even more and become a little fuzzy.

The next stage seems quite hazy looking back. But before I knew it he was kneeling in front of me and slowly and deliberately opening my towel. “Some girl is going to be very lucky when you get back in the saddle” he said with a smile.

“But I’m not even hard” I replied, almost apologetically.

He said nothing but leaned forward and gently flicked his tongue across one of my nipples. Then, settling back down on his haunches he began to massage my feet. He worked very slowly up the while lengths of the outside of my thighs and back down. He repeated the process up the fronts of my legs and back down. I knew what was happening next – he delicately stroked all the way up the inside of my legs, slowed down at my thighs but continued until, with delicate fingertips he oh so gently stoked my scrotum. That was the moment that my little used tool of recent months sprang to life.

He smiled and gently repositioned me so I was lying along the length of his sofa as he kneeled beside me. He then did with his lips and tongue exactly what he had just done with his fingers. This time over my entire body, last of all he did it to my now straining penis but keeping only to my scrotum and shaft, the head he left alone completely, For that I was curiously both grateful, and regretful. Quite apart from the physical and sensual feel of another persons touch my mind was also racing with the unthinkable doubts about my sexuality.

Now his massages became a little more intense as he rubbed harder and over my whole body. he reached somewhere and came back with a bottle of massage oil, Lavender and T tree I seem to remember, he poured some into a large spoon which he held briefly over a candle – I was worried about it bursting into flames but he seemed to know what he was doing. Gently he told me to turn over.

It seemed like an eternity, I hear a rustle and a chink of bottle and spoon. And then right between my shoulder blades I felt an instant warmth, he was dribbling warm oil onto me and I could feel it’s hot silky touch working it’s way down my spine. I was amazed that such a small ladle could contain enough.

But the line of oil drew itself down my back – and continued until I felt the warm glow between my buttocks and there it stopped.

Finger tips next – firm and with even pressure tracing a line through the oil from between my shoulder blades up to the top of my neck and back down again. Up and down going al the way up and part of the way down. With each repetition the finger tip pressure moved a little lower down my spine. Lower until it reached the very top of the cleft between my cheeks and, there it stopped, the fingers were removed and I was again left very still, wondering what was to happen next.

I heard him adjust his position and then whole hand was at my shoulders, kneading and pummelling – it was both rough and gentle which I know makes little sense but it was physically a very pleasant experience – so much so, and so relaxing that I was aware that my erection had subsided fully.

Again the hands worked their way down my back, then over the outside of my buttocks and back up. Gradually, deliberately he began to spend a little more time at my buttocks and then that’s where they stayed. Moving ever closer to the cleft and then after an age I felt the slightest and briefest touch against my anus. I started as though a bolt of electricity had gone through me, but within seconds it happened again, a little firmer, and a little longer.

I knew I had always liked it when girlfriends and then my wife had touched me there. My mind said it should be different if a man did it, my body said otherwise. And I felt my erection return with a vengeance underneath me., so much so that I had to adjust my position to accommodate it. This he took as encouragement, he took advantage of the lift of my bum and the resultant slight parting of my cheeks to rest a finger there. It wasn’t moving; it just lay there, right in the middle of my hypersensitive anus applying gentle pressure.

Turn over again, I was instructed by a voice that seemed a million miles away. I paused for a moment; aware that to turn would be to reveal a painfully large erection. Come on, said the voice, and slowly, almost reluctantly, I did. That’s gorgeous, he said, and with methodical precision he placed the most delicate of kisses right on the very tip of my cock. Which responded instantly with a spasm.

I looked dow and saw the first tiny droplet of pre-cum gather at the slit on my gland, he noticed it too and touched a finger tip to it and traced a little circle around the eye. I gasped.

“Would you like me to make you come?”

I nodded.

He massaged my inner thigh and worked his hand in again cupping my balls, and pushing on back to my anus. The finger tip again and the gentle pressure, gradually building until – I felt that single finger push inside. I groaned involuntarily as the finger pushed a little deeper and is thumb massaged the outer side of my hole. Keeping his finger moving he leaned forward and began to lick my balls and then with aching gentleness the length of my shaft stopping just short of the sensitive end. Then he did it again, and again to the top, the underside, the edge. All the while keeping up the pressure on my arse which he teased with continuous in and out movements with his finger. He sat back a little and used his free arm to re-arrange my legs, which he pulled further apart as he sat watching my cock, continuing to finger-fuck my anus. All the while rubbing my ring with his thumb as though he were pinching it between the finger inside and the thumb outside.

Now he just sat and watched me respond to his probing. He paused, picked up the oil again and I gasped as I felt a little trickle of it, onto my scrotum and down to his hand. “time for a third finger I think” he said almost casually – “Christ, I thought we were still on one”

With that I could feel my self being stretched, it was slightly painful but the pleasure was intense. I was awash with a wide mix of feelings ranging from self-revulsion – I was doing something that I “knew” to be wholly wrong, but I was thoroughly enjoying it. A few girls had fingered me in the past, and I’d thought that was good but this … this was a finger fuck, almost a hand fuck, on a whole new level. It was abundantly clear that he knew exactly what he was doing, it was equally clear that he enjoyed it. With incredible gentleness, he eased his hand out and lifted his weight a little and shucked off his dressing gown, His skin was as smooth as any girls and he obviously looked after himself – not a beefcake by any means but certainly well toned and not an ounce of flab. I was both impressed and a little jealous as I looked down at the slight paunch which I had long talked of losing but never quite got round to. He stood and eased down his bright white and very tight briefs. And I was for the first time in my life confronted at close quarters with another man’s erect penis.

Another overwhelming rush of mixed feelings, fear that I was about to lose control, disgust that I was so attracted to looking at it, curiosity and echoes of every family dinner I every remembered in which some homophobic line of humours had been discussed, I had grown up with an innate dislike of the very nature of homosexuality, and here I was, naked and turned on with another naked and turned on man. Confused just didn’t come into it, In the past there had been some fantasy about it – even talking about the possibility with girlfriends as a fantasy but, reality – well that was scary, and just a little bit exciting.

“OK” he said as his pants slid down his legs to the floor “you don’t have to do anything with this if you don’t want to, you’re in control and we stop any time you want” he went on to explain that he’d only taken off his undies because his own erection was getting too uncomfortable.

“Thank you” I replied because, looking into his eyes I could see that he really meant it. “Let me show you something different” he said. I don’t think I said anything at all but nodded in a dumb and accepting way, part of me wanted to stop, part of me knew this had already gone further than I intended but part of me, that part that had knowingly gone in the middle of the night to a gay man’s house for a … ’drink’ , that part, wanted more. On a purely biomechanical level, I really needed to come it had been so long. Perhaps that need was what encouraged me in the first place.

Muttering a few quite instructions he had me sit up on the sofa and slide down so that I was just hanging over the front. Whilst gently stroking and caressing my legs he positioned himself between them. On an impulse I reached out and touched his penis, which felt hot, smooth and strangely pleasant. He gasped a little at my unpractised touch and closed his eyes for a second, breathing deeply. Then he kneeled down, down and I watched as he was now lying partly on his front and propping himself up somehow. He grabbed a pillow from the sofa and lifted my hips, and placed it under the small of my back. For a minute, I thought he was going to tr and fuck me and I really wasn’t ready for that, and I tensed myself up. “Just relax’, he said, “Don’t’ worry, I promise it’s not what you think”

I felt his hands beneath my thighs and I felt myself being manipulated into the position he wanted, my buttocks were parted and then an erotic bolt - ran through my entire body. Something like I hadn’t known since my first real orgasm in that car all those years earlier. All I could see was the top of his head behind my proud member as he probed my anus with his tongue. I had never even begun to imagine that men did that,

This was awful, this was disgusting, this was a depravity such as I had never thought possible, this was sick – but above all, it was amazing and wonderful.

I have no idea how long that lasted, it seemed like forever and I was disappointed when it ended but he came up for air and told me to lay back along the sofa. As I did, I moved close to his twitching erection and paused to look. I’d seen guys in showers obviously but I was now two inches from a hard, glistening, pulsating male member. The tip shone with precum and the little ring of foreskin was half way back over the purple end. In a dream like trance I leaned those few inches and took the top into my mouth. It tasted fantastic! I had no idea what I was doing so I fell back on a technique I learned from my older lover of past years, I treated the head of his penis as though it was a clitoris, albeit a very big clitoris! I sucked rhythmically and flicked it with my tongue. I heard a few gasps and felt him rock back and forwards a little – I think he was resisting the urge to fuck my mouth.

He pulled away and thanked me but said this was my night; it’s an honour to be the first he said. I noticed as it pulled away that the foreskin was now all the way back.

With that I felt his hands touch me and massage their way back to between my legs as another great dollop of lube was placed on his hands and between my cheeks. Now I lifted my l hips a little and opened my legs to give him better access. And I felt my self being expertly probed and stretched again as I writhed and thrust my self harder onto his hand.

I was aware of a little pain but I was mostly aware of an acute pleasure I had never experienced before. “That’s four fingers” he said, “more than enough for your first time”

I think my only reply was a half laughing mumble of some kind.

Now I watched as, slowly, so slowly it seemed to take and age he leaned down, closer, closer and ever closer to my throbbing penis, I watched as his mouth opened wide and he lowered his head down over my cock the sight was very horny but I couldn’t feel much – he kept his mouth wide open so that my cock was inside but barely touching. Then I was enveloped by an amazing sense of cool pressure as with such delicacy he closed his mouth around me. Every BJ I’d had before had invoiced some pressure from tongue, lips or teeth but this felt like a butterfly was on me. And that’s all he did. Keeping his mouth open so that I could barely feel him he moved up and down over the length of my cock, I felt gossamer touches of tongue and lips but there as no pressure no overt sucking just a rhythm of delicate strokes over my head in time with the hand that gently pushed in and out of my stretched anus.

It started low and deep in me somewhere, I knew that I was going to come and that it was the kind of orgasm that I would not be able to control or hold back and I could feel it build from the soles of my feet to the tips of my fingers, I could feel my anus contract and squeeze his hand and all the while that delicate bobbing up and down of his head so that I could feel his mouth on me, but only just. It was welling up in me and I began to thrash, I reached for my cock to speed up the process but he gently kept my hands away and continued. It seemed to go on for ever but he was in complete control – my vision began to cloud and sweat was pouring from me, I was gasping and breathless and totally in his thrall.

He timed it to perfection because with just a little harder push into my anus it began, and the moment I began to shoot my come into his mouth he clamped his mouth tight and hard onto the swollen end of my penis. The effect was intense. I totally lost control of my body and bucked up and down, ramming my cock into his tightened mouth, I was aware of the pulsing of hi tongue as he swallowed each gush and as he did His hand seemed to do something different in side me, Gradually my thrashing stopped and I settled back down his hand gently eased out of me causing me to jump and shudder a little but he kept his mouth tightened over the end of my penis as the very final dribbles of my come were sucked from me. He ran his hands over and around my body as he kept his mouth in place, gradually reducing the suction and pressure but not letting go until I was completely soft. Then with a sucking pop, he spat out my now flaccid and spent cock.

I was too breathless to breathe but smiled as best I could as he shuffled us both around so he could sit on the sofa beside me. His still erect cock right in front of me. I felt almost duty bound to at least try and reciprocate so I reached out a hand. I had never made or even seen a man come before so had little idea what I was doing but assumed his cock would be much the same as mine so simply wanked him the way I would myself.

I had already had so many new experiences I wasn’t really ready for this one and continued out of some sense of politeness. From his point of view I must have been very clumsy and mechanical compared to his own delicate and practiced technique, but it seemed to have the desired effect as he soon shot onto his own chest.

The moment it was all over I was overcome again with awkward discomfort about what had happened and felt intense guilt that I had enjoyed it.

I quickly dressed and thanked him as he sat with an amused smile clearly enjoying my discomfort.

“You know where I am” he said as I made hastily for the door.

We did meet once more for a similar experience but after that we left each other a few messages on the chat site but somehow never again managed to be free at the same time, but I was lucky that my first gay experience was with someone so gentle and he started me on a new road that I’ve enjoyed as pleasant diversion every once in a while ever since


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