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Another Holiday with Leslie.

Posted by: Age: 35 now, 15 then Posted on: 3 comments
7 likes 1100 views Category: Masturbation Male-Male Tags: new friend, sleeping together, nocturnal events, swimming in the sea

A surprise invitation to an unexpected, but enjoyable, holiday.


Life, we are told, is full of surprises and certainly, the story I am about to tell came as a great surprise to me. I found myself in a sexual encounter coming from a source I hadn't even suspected. The Benton family, as I'll call them, lived on the other side of the road from us. There was Mr. and Mrs. Benton, a son, Leslie, who at the time of this incident was 15, the same age that I was then; and there was Barbara, the daughter, who was grown up and no longer lived at home.

I'd known Leslie for some time, but wouldn't say that he was a close friend. We went to different schools, but we did sometimes meet up. We'd helped each other with bicycle repairs and had been on a few evening rides together. Once or twice, we'd helped each other with homework problems; and on a few occasions, we'd gone together to the local swimming pool. This is why, having seen him naked, I knew that Leslie was circumcised. He was a stocky lad, dark haired, dark eyed, and a rather cheery soul. The Bentons were keen and enthusiastic members of their local church, a very “happy-clappy” fellowship (and there's no criticism implied in that description). Leslie also seemed enthusiastic because he played guitar each week in the church's worship band. That's why I never expected a sexual encounter with him.

At the beginning of the school summer holiday that year, and quite unexpectedly, Mrs. Benton one day approached us. She asked if I'd like to accompany them for a week's holiday to their seaside bungalow because Leslie's school friend, who'd planned to go with them, had backed out for family reasons. Well, I got on well with Leslie, so I said, yes, I'd be delighted to go. My family was not going on a holiday until the last weeks of the school vacation. So, on the appointed day and with my suitcase packed, I joined the Bentons for a two-hour drive until we arrived at their seaside bungalow.

The plan was that Leslie and I would sleep together in a double bed in the second bedroom. That first night, about 10:00 pm, he and I retired there. We undressed and clambered into bed, me on the right and Leslie on the left. For some time, we lay side by side chatting away, planning what we intended to do in the coming days. How long we talked I don't recall, but eventually I fell asleep. Imagine my surprise, therefore, when I suddenly awoke to feel Leslie gripping my right hand and dragging it across his body! Suspecting there might be something interesting afoot but not quite knowing what or how to respond, I pretended to be still asleep. Very slowly, so as not to awaken me presumably, he gently laid my hand on his own lower body; once it was there, I realized that his pajamas were open wide. I could feel his pubic hair, AND that he was rigidly erect!

He waited for perhaps a minute, and then he slowly wrapped my fingers around his hard shaft. As he was cut, I could feel its shape and vein-pattern, and that it was throbbing. Then he began to move my hand up and down. Clearly, we wanted me to wank him! But not wanting to betray that I was awake, I did nothing. Well, to be truthful, I didn't really know what to do! For some minutes, he kept moving my hand up and down, and then waited to see if I was going to respond. I wanted to, but so surprised was I to get this from someone I thought to be “religious” that I did nothing.

Then, and very slowly, Leslie managed to maneuver my left arm around his back and placed my left hand on his buttock, which was bare. By this time, he'd worked his pajama trousers some way down his legs. Not understanding what he really wanted, I continued to do nothing.

When this latest action failed to achieve whatever it was Leslie wanted, he reached over and put his hand inside my pajama trousers and started to squeeze my penis. As he did so, he began again to move my hand up and down his own. Frankly, I was so surprised to get this sort of reaction from “churchy” Leslie that I was confused. I still did nothing.

This performance went on for some minutes until, at last realizing it wasn't getting him anywhere, Leslie released my hands and turned over with his back to me. For a couple of minutes, he lay still and then I realized he was masturbating. He'd decided he would have to satisfy his own urges. To be honest, I was disappointed as well as confused. I'd have been happy to oblige him, but his actions had been so surprisingly unexpected that I'd simply not known how to best react.

The next morning, Leslie made no reference to what happened the night before, and I thought that might well be the end of it. I was wrong!

The next night, we again went to bed at about 10 o'clock, undressed, and climbed in. Like before, we talked for a while and then, really to see if anything would happen, I pretended to get sleepy and to doze. As before, Leslie did nothing for some time. Then he prodded me hard in the chest, to see if I was asleep I suppose. I realized that there was more to come, so I obliged him by not responding.

Convinced I was asleep, Leslie rolled down the bedclothes and then wriggled around until he'd pushed his pajama trousers well down his legs. Then he turned towards me and felt inside my pants. Once he'd located my penis, he began gently to work on it. My penis obliged him by erecting quite quickly! Once he'd managed that, he slid my foreskin back and forth, obviously to ensure that, even asleep, I was aroused. He then half turned away, so that his back was turned towards me. Reaching back, he found my right hand and slowly drew it across and around his body until he could place it on his own (very!) erect penis. He then partly lifted himself off the bed and reached back under his body with his left hand until he found my left hand (I was lying on my left side). Taking a firm but gentle grasp on my hand, he drew it towards his buttocks and, after holding it there for a few seconds, he found my middle finger and pulled it towards his anus. Now I realized what he wanted, and what he'd wanted the night before! He wanted my finger IN HIS HOLE! I gulped in surprise, but I didn't resist.

So, with one hand, he drew my left middle finger between his buttocks and held it there. At the same time, with his other hand, he wrapped the fingers of my right hand tightly around his erect penis! Believe me, all this was some maneuver. Once I'd realized his plan, I co-operated and aided him to do exactly what he wanted. I'll always remember his reaction when he eventually got about an inch of my middle finger inside him: gasping quite loudly but, in a croaky, barely audible voice, Leslie whispered, “Yes, that's IT!”

Next, he turned towards me, almost on to his back, thus trapping my finger firmly in place. Then, with his now free left hand, he took hold of my right-hand fingers (wrapped around his penis remember!) and began to slide them up and down his hard shaft. Reaching across with his right hand, he went inside my pants and started to stroke my penis, itself throbbing by now with excitement. I figured I could now respond in the way he wanted. I reasoned, he'd think anything I did would be the result of him wanking my penis; after all, I was “asleep.”

So there we were, each wanking the other; and thus, engaged in what Leslie clearly wanted, surprising though this was to me. I suppose it went on for five or six minutes. I found it MOST enjoyable, and, clearly, so did Leslie! It was, I realized, probably going to result in my cumming too, whatever Leslie himself achieved. I just hoped he brought me to climax before he blew because I thought that, once he'd cum, he'd probably stop working on me. I'd be left aching for it unsatisfied. Fortunately, that didn't happen: just as I was beginning to feel those exciting stirrings deep within, Leslie quietly croaked, “Oh, yes, oh, yes!” His penis hardened and throbbed and, with a gasp, he shot his load across his body; and that was enough for me: I blew mightily inside my pajama trousers!

As soon as Leslie had recovered from the rapture of cumming, he released my penis (which he must have realized was wet and sticky!). Then he pulled my left hand away from his bum, and took my right hand off his own now slackening but very wet and sticky penis. For some minutes, he lay there just recovering, and then he slipped out of bed, got some paper tissues from his suitcase and wiped himself dry. He then pulled up the blankets, turned over and. With a few minutes, his deep, steady breathing told me he was sound asleep and VERY contented!

I was contented too, but also very wet and sticky inside my pajama pants. Waiting until I was sure Leslie was sound asleep, I stole out of bed and into the bathroom. I used toilet paper and I made myself as dry and comfortable as possible. Once back in bed, I too was soon asleep.

The next day, Leslie made no reference to what had happened, but I'd realized he was up for it as much as I was. If we could come to some sort of 'arrangement', then we could have a great time together without the need for any subterfuge and trickery. That afternoon, Mrs. Benton provided the opportunity. It was a very hot day and she turned to Leslie and said, “Why don't you take Tom down to Ashby Creek [not its real name] and have a swim? You know there's hardly anybody ever down there, so you'd have the place to yourselves.” I indicated that I thought that was good idea as it would give me time alone – and no doubt naked – with Leslie. In that situation, could we not come to that 'arrangement' that would ensure that we'd be, shall we say, more 'intimate' with each other? And so, it was decided.

Armed with swimming trunks and towels, we walked the mile or so to Ashby Creek. We quickly undressed, put on our trunks and plunged into the sea. As I've said before, I'm a good swimmer and enjoyed it greatly, and so did Leslie. For perhaps an hour, we really had a ball. Then we came out of the sea and walked back to where we'd left our clothes. There was, indeed, no one else there but us. I decided to make my move. Without any warning, when we were both naked, I flicked Leslie's bum with the edge of my wet towel. I timed it beautifully and caught him right on the curved of his right buttock. There was a crack like a whip and Leslie yelled because I'm sure it really stung. Immediately, just as I'd hoped, he spun round and lashed out at me with his towel. Soon we were capering around, cutting and slashing at each other like a pair of naked, but grinning, gladiators. Then, of course, as one would expect, the battle became more hand-to-hand, and we were soon rolling about together, still naked of course, in the warm sand.

Eventually, I had Leslie pinned, face down, on the sand. I was astride his legs which I had securely held between my own legs. Grasping the bottom of his rib-cage with my fingers, I started to tickle him and, as he squawked loudly, I slowly moved my hands down until I was on the front of his soft belly and could already feel his pubic hair. His struggles, I noticed, became less, and so I pressed on downwards and inwards. Soon I could feel his penis and, jokingly, I said, “Well, would you believe it! I've found something really interesting down here.”

“That's my one and only private cock,” Leslie chuckled, “and isn't available to strangers, except on special days!” To which I replied, “But I'm not a stranger. We've slept together for two nights. Surely, I've got privileges! And isn't this a special day?” Leslie replied, “Well, if you put it like that, I suppose you're right.” (I realized, at that moment, things were going to pan out as I'd hoped.)

At this point, I released him and he turned over on to his back, but made no attempt to get up or cover his nakedness. (It did flash through my mind that my remark about our sleeping together did perhaps make him wonder if I'd known about the two previous nights' events. He made no reference to it though and, actually, never HAS referred to those two nights.) I reached forward, took hold of his package, and said, “D'you know, I've never really examined a 'cut' dick!”

We were both covered in sand, and the 'cut' dick in question was covered in abundance. I reached across to one of the towels which was nearby and used it to flick away as much sand from Leslie's penis as I could. He made no attempt to stop me and, by the time I'd finished, his penis was beginning to enlarge and stiffen. I realized that, yes, I had crossed a line: from now on, it was going to be “open season” for sex between Leslie and me.

I lay beside him and put my arm around him and, reaching down, took hold of his penis and began to rub it. It felt strange not having a foreskin to manipulate. I didn't let that cramp my style. After a moment or two, Leslie asked, almost shyly, “Have you ever done this before?” and I told him, yes, I had. I told him that I'd had a friend called Brad, and we'd been wanking buddies for a couple of years. I asked him if he'd a regular friend, and he said, no, no one special; though he did have a number of “one-night stands” with school mates.

After a couple of minutes, and I remembered what he'd wanted on the two previous nights. I asked if he was enjoying it, and if there was something else he'd like? Without hesitation, he told me, so I slipped my left hand under him and penetrated him. He tightly closed his eyes and arched his back as I went in. Then he gasped and said, “OMG, Tom, that's just it!”

Manipulating him both front and back, I soon had him writhing and gasping with pleasure. He was thrusting his hard, pulsing penis into my right hand as though his life depended on it. I was truly enjoying what I was doing, and really wanted to see him blow a huge load. After about five more minutes, he did just that. With a yell of joy, he fired his first load so high that, had there been a seagull passing over, he'd have shot it down.

I carried on until he ran dry and his penis began to slacken, and then I let him relax. As he lay there, breathing heavily and contentedly, I was greatly tempted to kiss him. I wasn't sure if he was into that, so I didn't. While waiting for him to return to normal, I wiped the sand off my own package and began to stroke myself. I REALLY wanted it!

At last, realizing what I was doing, Leslie sat up and indicated I should get close to him. When I did, he told me to kneel. As soon as I was in position, he knelt beside me, on my right side, and took hold of my throbbing rod and began to slide my foreskin back and forth. Though he didn't have one of his own, Leslie knew how to work it. (Was it one of his school buddies, himself 'uncut', who'd taught Leslie this?) He also placed his left hand on my buttocks and held it there throughout. He made no attempt to penetrate me as I'd just penetrated him.

He didn't have to penetrate me because his wanking technique, which was sometimes fast and sometimes slow, was enough to get me groaning with approaching rapture. That rapture was a few blissful minutes away. When it hit, I'll swear it began in my feet and swept through my body to my head. Happily, it lingered longest in my hard and throbbing penis. From that appendage, I shot half a dozen ropes of semen far out across the sand.

Leslie kept going until all the ecstasy had ebbed away, and then he just held me until I could breathe properly again. After that, still with sticky dicks, we lay side by side on the warm sand. We said very little, but I'm sure we were both thinking that our remaining nights together were going to be, well, memorable, to say the least. On one of those night, though still making no reference to what he'd done on our first two nights, Leslie did confess that he'd earlier fancied me from a distance. That was the reason why he'd invited me on the holiday when his school friend dropped out. This certainly explained his actions on our first two nights!

After a time, we went down to the sea and washed ourselves, well each other, actually. Then we dressed and walked back to the bungalow.

Our remaining nights were indeed well worth remembering. Once we were back home, we occasionally met up to give each other pleasure. That continued, off and on, until we both left for university. Sorry to say, we lost contact during our student years and we've never met up again. That summer holiday will remain forever vivid in my memory.



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