How I Joined The Mile-High Club

He was wearing a crumpled kind of casual jacket over a plain ‘T’ shirt, with grey track-suit bottoms and trainers. He was in front of me in the queue and every time the queue moved forwards in its snaking fashion leading to the check-in desks, we passed one another and I got a good look at him. He looked a bit fed up. Strange, considering that he was presumably going on holiday.

He was about 5’ 9” and slim, with a tousled mop of light brown hair which made him look like he had just got out of bed. His eyes looked as though they might be blue or grey but it was difficult to see them, as he tended to look down all the time. I suppose this, coupled with his slouching stance, made me think he was miserable. Or maybe he was still just a teenager and hard to please.

As he walked along, I could see what I was sure was an outline of something down the left leg of his track-suit bottoms that swayed slightly as he moved forward, enough for me to decide that he was not wearing tight underpants!
His parents didn’t talk to him much in the queue but he pushed the luggage trolley along behind them. However, I noticed that, when they got to the desk, there was some conversation with him about the seating arrangements. I supposed that his parents were just making sure they were all seated together.

It was another hour or more later that I saw them again, at the boarding gate. By this time, he was sitting beside his father and listening to his i-pod. There were a few spare seats on his other side and I approached and sat down leaving a gap of two seats next to him. However, to make sure nobody was going to spoil my view, I put my shoulder-bag on the seat next to me.

He was slouching forward at this point, quite oblivious to me and absorbed in his i-pod. He had taken his jacket off and I now saw his bare arms, covered in soft hairs. As he leaned forward, his ‘T’ shirt rode up behind him, revealing his spine and the waistband of his underwear; at this angle, side-on, I couldn’t make much out but it was a plain blue elasticated band, below which was the hint of colourful cotton. He was wearing boxers; so he wasn’t quite a “freeballer”, but close enough!

Eventually we got up to board the plane and the queue I joined moved ahead of him and his parents in the next one. So I lost him again.

The seats in our bit of the plane were in a 2-4-2 configuration and I had got myself a seat by the window on the right-hand side. My row was the back row of this section, so there was a partition behind.

Having settled down, I was reading the details of the in-flight entertainment and stuff like that when I saw him again. He was heading down my gangway and my stomach did a little flip-flop as he stopped at the seat next to mine and plonked his bag & jacket on it. I pretended to be paying no attention but as he rummaged in his bag, I couldn’t wait for what I knew would happen next.
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As his stretched up to the overhead locker, his ‘T’ shirt pulled up and I got the most fabulous view of his tummy, revealing and the “treasure-trail” of hairs down the middle, leading to the blue waistband of his boxer-shorts. And as he pushed his stuff in the locker, I got the best view yet of that delicious item down his left leg, as the material stretched tightly across it, revealing the beautiful outline of his balls and a more-than-respectably-sized cock.

Meanwhile, his parents it seems had seats across the aisle but two rows forward. That was what all the talking was about at check-in! There was some interaction between them at this point but he just seemed to grunt or mumble and turned away to sit in his seat, seemingly happy to be on his own away from them. I gave him a brief, polite nod and smiled at him as he sat down next to me. And we both then ignored each other. But it was difficult not to keep glancing across at his thigh, to get another look at his equipment – which to all intents and purposes had disappeared from view. So that was that; or so I thought.

The “ice-breaker” opportunity happened just a few moments later as we were taxi-ing and he seemed to be straining forward to look out of the window quite intently. Impulsively, I asked him if he wanted to change seats with me and sit by the window. I said I didn’t really mind and that he seemed to be far more interested in seeing out than I was as I had done it so many times before. He looked at me for a moment longer than was comfortable, enabling me to see into his grey eyes; then he looked across and down the aisle towards where his parents were sitting and said, “Well, if you’re sure…”. I told him to be quick about it, as we were taxi-ing and the stewardess would tell us off for unbuckling our belts while she was still giving us the usual safety drill.

So we swapped seats quickly; him standing up and shuffling across in front of me as I pushed-up the centre arm-rest and slid across behind him. In the course of this 5-second manoeuvre, I not only got another glimpse of pale flesh and the back of his waistband but my face came precariously close to a pair of deliciously round buns as he passed across in front of me and my hands inadvertently brushed against his legs, as a jolt of electricity went through my whole body. I had actually touched him! Well, his track-suit bottoms at least!
Now I had him between me and the window, on my right side, with the aisle to my left and a partition behind us both.

Throughout the next couple of hours, on and off, I chatted to him. I made my remarks fairly “throw-away”, so as not to make too obvious my sexual interest in him. We talked about i-pods and computers to begin with, but later I did manage to find out that his name was Ben and he was 19; his “father” was in fact his step-father and he didn’t like him much – largely (I figured) because he had replaced his estranged real father, who he mentioned more than once. His older sister was married and living abroad in Germany………well, you get the idea; it’s not important now. I earned a few extra points off him when they did the drinks round; instead of wine with my meal, I asked for a lager (the same as he had ordered) but I deliberately never drank it and gave it to him instead – he seemed to think that was “matey” of me. They say you get children’s approval with chocolate – but a young man’s is bought with booze!

The most interesting “development” was when he fell asleep for a bit after the main meal; not surprising, really, after two beers! His legs were stretched out in front under the next seat, having the effect of stretching the front of his tracksuit bottoms. At last, I saw that bulge again, still down his left leg but so much closer to me now. I was sure it was bigger than before, and I stared at it, mesmerized by it; until I saw it twitch. Was that my imagination? It happened again – a little twitch! Oh God, that did it; I was juicing myself by this point, just looking at him. I nearly came then and there in my seat! They say that a young man thinks about sex every few seconds and this young man was certainly thinking about it now, in his sleep! I wonder what his dream involved. No matter. He was semi-erect, that’s what matters!

I desperately wanted to touch him – well it actually – but I didn’t dare. Instead, I feigned sleep myself and allowed my leg to fall softly against his outstretched left leg. I contented myself with this for a good few minutes while he offered no resistance, and in my mind, I came about three times thinking about him and that still semi-erect organ lying just inches away from me.

Then he woke, drew his legs up and started shuffling. I realised he was unpacking his blanket, which he then arranged across himself, pulling it up over his front with both his arms inside under the blanket. Now my view and the bodily contact were lost and I thought, “Oh well, it was lovely while it lasted”.
While he lay back there, he now had the head-phones on and was watching something on the view-screen in front of him. However, after a few moments, I realised that the blanket wasn’t entirely static. I could tell that his left arm has resting on his leg but his right hand seemed to be near his genitals – you know, the way all men do. But there was a tiny amount of movement down there – almost undetectable (except to the eye of an expert like me!) and it was definitely a gentle but repetitive movement. He was pleasuring himself! Mind you, I could hardly expect otherwise; he was 19, had just had 2 beers at 55,000 feet and had just woken from a sexy dream with a semi. He was bored and horny!

It was decision time for me. If this continued unabated, he was surely going to get frustrated and seek an outlet. He would most probably get up and go to the toilet and wank off in there. Was I brave enough to follow him? Indeed, was it even practically possible for me to “muscle-in” with him without anyone seeing or without me causing a scene? He was hardly likely to invite me, was he? There was only one thing for it.

I slowly and deliberately slid my arm over the centre arm-rest and into the gap between the side of his seat and his leg, presently covered by the blanket. He was awake, so I figured his reaction to this would be instantaneous, one way the other. And I was right. As the side of my arm touched him, he started. But he didn’t do anything – he just sat there, as if nothing was happening. It was possible he was terrified and didn’t know what to do. As he sat there, I slid my hand under the edge of the blanket and turned my palm until it rested against his thigh. He still didn’t move. I spread my fingers across his outer thigh until – electricity! My little finger made contact with the little finger of his left hand on the top of his leg. With just this contact, I stroked his finger and, to my amazement, instead of pushing my hand away, he slowly turned his head toward me and looked at me, full in the eyes. I looked back at him, with my heart pounding in my ears as his eyes flicked down to where my hand now rested, and then back to mine. He slowly turned his head away, breathed-in deeply, lay his head back and closed his eyes. As he did so, his little finger began “playing” with mine. It was his consent.

After a minute or two of this, I began to wriggle my hand under his hand and onto the top of his leg. He kept his hand over mine and it felt warm and sweaty. I gently squeezed his leg and felt a reciprocal twitch of his leg muscles, as his hand squeezed mine. He knew what I was up to and he liked it!

Still covered by the blanket, I moved my hand across to the inside of his thigh. As I did so, he lifted his left arm under the blanket and gently placed it down in the gap beside his seat underneath my own arm. Meanwhile, his right hand, which had been over his genitals, he used to adjust the blanket over himself, lifting it gently across until it came to rest across his stomach. The position was now perfect; with my elbow resting against his pelvis, my hand came to rest on the now quite hard bulge down his trousers, which I caressed, pushing my fingers down into the gap between his legs, filled by his balls. As I proceeded to slowly massage his organ through the material of his track-suit and boxer-shorts, I could feel him throbbing in the palm of my hand. Whether he was doing it deliberately or involuntarily I don’t know but every time I stopped massaging him, he seemed to signal with a pulse through his tool, while the fingers of his right hand gently stroked my arm. I decided to take it to the next stage.

I swung my hand and arm up towards his waist and slid the palm of my hand onto the naked flesh beneath his ‘T’ shirt. Then I slid my hand under the waistband of his boxers and back down towards his groin. As I made this move, I felt the first sign of resistance; his right arm came down to press on mine, as if to block this “entry” but I was too close to my prize to give up now and my hand was able to wriggle under the weight of his arm, into the warm hallows. The pressure on my arm relaxed; he was obviously excited and didn’t really want me to stop! I now felt the warmth of his groin and the matted bush of his pubic hair, his balls, soft but firm and already tight from his excitement, and his organ, now long and hard and dead straight down the leg of his boxers. I grasped it firmly. He was uncircumcised and with my index finger, I began teasing the flesh covering its tip.

I immediately discovered that he was already oozing pre-cum. He was definitely excited. And rock-hard. Between my index finger and thumb, I pulled back the skin to reveal the head and I heard him gasp involuntarily as my fingers now wrapped the swollen and slippery head of his tool. My thumb now played on the top-side of his organ while my other fingers tickled and teased the sensitive underside, gently rubbing his organ against the inside of his soft thigh, making it slippery with pre-cum. Every few seconds, I would just hold and gently squeeze his organ and feel his uncontrollable throbs as he became more and more aroused.

Here was a 19 year-old, with a stonking hard-on, fully aroused and dribbling pre-cum in my hand, breathing heavily now and swallowing hard. He wanted to cum and nothing was more important to him at this moment. He was breathing in short, stifled breaths and as I looked at the profile of his face, I could see his nostrils dilated. His eyes were still closed and he was relishing the moment. And I was now soaking my own briefs with the excitement! But suddenly, his right hand appeared out of nowhere to rest firmly on top of the blanket and my own hand underneath. Surely he hadn’t changed his mind all of a sudden, at this late stage? His hand pressed down hard and squeezed mine, and he whispered hoarsely, “No – Stop!” but my fingers continued their teasing motion under his grip and seconds later he let out a stifled gasp, as I heard him whisper, “Oh, shit…no…” and his whole body gave a shudder, arching deep into his seat as his head lifted forward from his head-rest, while his swollen, slippery tool suddenly exploded into the fingers of my hand – two, three, four, five, six times I felt the cum coursing down the whole length of his organ and out through my hand, all over his leg and into the cotton of his boxers. He was trying to cover-up his gasping for air by breathing heavily through his nose now but he still he hadn’t done – seven, eight, nine times I continued to count as his organ pulsed powerfully and jetted still more & more cum into my hand until at last, the pulses became less and less intense and he breathed-in in one big deep breath and let it out in final satisfaction, as his head gently fell back against his seat, his eyes still closed.

Wow! I turned my face towards his and, as I did, he turned and opened his eyes and looked at me. I smiled, a kind of soft smirk and raised my eyebrows at him. He blinked – and grinned a sort of slightly embarrassed little grin and then looked back at his view-screen. He still had his head-phones on! His hand was still clasped over mine under the blanket and my hand was still grasped around his soaking wet and still rock-hard organ. But it was running everywhere; all over his thigh, down his leg and in his boxers. I had an inspiration. In my left-hand pocket was a fresh handkerchief; I always carry one, though not really for this kind of thing! With my other hand I reached into my pocket and took it out and handed it across to him. He looked at it, then at me, and he took it from me. Beneath the blanket, I now felt his own hand for the first time inside his boxers and then felt the handkerchief, as it was placed across my hand and his soaking parts.

At this point, I felt it best to beat a discreet retreat, so I carefully withdrew my hand and arm from its sticky resting place, leaving an unfortunate gooey trail as I did so. He then used my handkerchief to discreetly clean himself up and, a few moments later, the handkerchief reappeared, now visibly quite wet and definitely “used”! He didn’t know what to do with it but I immediately offered to take it back.

But now I was the one who had to go to the toilet! I was soaked too and desperately in need of something! Needless to say, I took the handkerchief with me! When I returned to my seat beside him, he looked up at me and gave me a sort of coy grin and I smiled back. We chatted quite a bit during the rest of the flight, on and off, and I found out quite a lot more about him. But that’s perhaps for another story!