I wasn't happy to get a window seat instead of the aisle I prefer, but I was mollified a bit when I saw the cute guy they put in the middle seat to my left. He was real young (I learned later he was a college freshman), thin, with dark blond hair, beautiful blue eyes, and perfect white teeth. I definitely wouldn't mind flying next to this guy!
I slipped my shoes off, pulled the blanket over myself, and napped for about an hour after the plane took off, and woke up realizing my left leg was pressing up against his right leg at the knee. It felt nice and warm, and although he looked to be sound asleep, I couldn't help wondering. Of course, I really WANTED to wonder . . . but why wonder when you can experiment?
I slowly extended my lower leg, carefully feeling for his foot. Because of the blankets over our legs and the narrow coach seats, I couldn't see anything, of course, but I figured if I moved slowly enough I could always pretend I'd just brushed him accidentally in my sleep. As I moved my leg, I felt myself getting hard.
After what seemed a long time, my toes finally found the heel of his foot. I'd wondered if he'd kept his shoes on, but as I slid my foot next to his, I could feel his warmth through his sock. I let my foot rest there for a bit, and looked over at him. His baby face was unperturbed, eyes closed. He had the most peaceful, innocent - adorable - look in his sleep.
I decided to live a bit more dangerously, and I slid my foot back along his, then around the heel, and back up the far side of his foot. This brought my whole leg into contact with his, my knee slightly under his, both calves pressed together, and my left foot nestled against his right. The warm pressure felt very nice, and I was very hard.
Then he moved. He made a small noise, pulled away from me a bit. I pretended to be asleep, rolled over to the side a bit, pulling away from him, heart pounding. He looked my way briefly, then down at his watch, and closed his eyes again. I waited a moment expectantly. And then I felt his knee press against me again. So maybe I'd surprised him, but he didn't seem to mind it.
A bit more boldly, I slipped my left foot back under his leg and up against his right foot. Again, I felt the full contact along our legs, but this time he didn't move. I slipped my left hand under the armrest and touched his thigh. No response. I stroked my fingertips along it - rather awkwardly, because the armrest was in the way. Still no response. I lifted the armrest and, making sure the blankets fully covered me, rested my hand on top of his thigh. He adjusted himself in his seat a little, but that was it. I moved my hand down to the inside of his thigh. Nothing. I gripped his thigh, stroking the inside with my fingers. Could he REALLY be asleep? He DID look at his watch, didn't he? I let my hand slide slowly up his thigh until my thumb touched his crotch. Heart pounding, I slowly slid my hand up onto his crotch. I could feel how hard he was in his jeans.
I relaxed a bit and squeezed his erection a bit through the cloth. Then I slid my hand further up until I found his belt buckle. Slowly, I started to undo it. He still lay there, breathing softly. While I fumbled a bit with the thing, I looked past him at the lady in the aisle seat on his left, but she seemed completely asleep too. The lights were dim and the plane was dark except for one or two people reading.
I got the belt undone and then undid the button on his pants. As I unzipped him all the way down, he shifted a bit, opened his eyes, and looked at me. I put my hand under his shirt and felt his tummy. It was completely smooth - just the way I like it. Then I slid my hand downwards, under his shorts, and around his cock. He smiled and closed his eyes again. It was too tight in his pants for me to do much with it, but I squeezed and fondled his dick for a little bit anyway.
Then I pulled out my hand and tried to slip it under him. He made a puzzled noise, and then lifted up a bit to let my arm go under. I gripped his pants and shorts from both sides and pulled them down almost to his knees. He kept a grip on his blanket so I didn't expose him, and then we returned to our previous positions. I let my left hand explore his body for a while. He was incredibly smooth above the waist, and I liked feeling him up there. I reached as high as his nipples and fingered both of them, before returning to his cock. He kept real quiet.
Now I could actually jerk on his cock, and he used his free hand to lift the blanket just high enough that it wasn't obvious what we were doing - not that anyone was up and about to see anyway. I jerked him for a while and then explored his bare thighs for a while. I fondled his balls, and even reached down far enough to just touch his hole, an action that brought yet another noise from him - couldn't tell if he liked it or not.
Finally I got back to just stroking his cock. This was a bit awkward to do left-handed, but under the circumstances I didn't have to be all that skillful. He was cut, but with enough loose skin to make jerking him easy. Not all that big either, but still a fair handful. I never jerked anyone off on an airplane before (or since!) so it was a thrill by any standard.
Then I felt him shudder and felt his dick stiffen just before he shot all over his stomach and (I think) the underside of the blanket. I kept stroking him until he touched my hand to stop.
I looked at his face and saw that he was panic stricken. Half-naked on a plane with cum all over you and a strange man's hand in your crotch, I guess I can understand that. I leaned over and whispered in his ear, "Hold still and let's get you cleaned up."
I pulled my hand out, licked some of his cum off, and then fished my bag out from under my side of the seat. I keep a box of tissues out of the bag, so I pulled out a handful and reached under the blanket (which he was still faithfully holding up) and gently cleaned him up, carefully holding his now-ultra-sensitive cock out of the way. I tucked the used tissues back into my bag and then pulled his pants back up, reversing our earlier operation.
I heard him sigh with relief as he buckled and buttoned himself, then settled back into his seat. At this point, I started to make small talk with him. He was pretty nervous at first, and I suppose the incongruity of talking with a man who just jerked you off as though nothing had happened was a little much, but he was pretty good natured, and we chatted comfortably after a minute or two.
Then I put my hand back on his thigh. He stumbled over a word, but kept going and made no effort to stop me. I slid my hand further, and, noting that he hadn't put his shirt- tail back into his pants, put my hand up under his shirt and rested it on his tummy, letting my little finger go into his naval, which was still wet with his cum.
Despite this, I kept up our conversation, learning (as I said) that he was a freshman at the local University, that he'd lived in the area most of his life, that he'd been visiting his girlfriend who was attending a school back east, etc. From time to time I'd move my hand a bit on his stomach, or I'd wiggle my finger in his naval. After a bit, he placed one of his hands on top of mine, gently holding it against him. I smiled and whispered, "I think this would be a good time to visit the restroom in the back of the plane."
"You mean, together?"
"Yeah. Can you climb over her without waking her up?"
While he negotiated this maneuver, I pulled a small tube of lube from my bag into my pocket and then followed him. No one was near the row of toilets at the back of the plane, so I opened one and we both simply got into it. I carefully locked the door.
It was pretty crowded with two in there, and I motioned him to sit on the seat, which he did. Then I undid my own jeans, exposing an erection that had been wanting attention for quite a while now.
His eyes got big as I stepped between his legs and put a hand behind his head, guiding my cock into his mouth. But he didn't say much more than "um" and if he resisted at all, it was very little. He did close his eyes.
I don't think he did more than suck me gently - almost like he was sucking a large straw, not giving a blow job - but we'd been at this a long time now, and I was very, very horny, so I shot almost instantly. He made some unhappy noises as I filled his mouth with what felt like a really large load of cum, but I held tight to his head, and whispered "don't make a mess on your shirt," so he ultimately sat there quietly.
"Milk it down with your lips so it doesn't drip." I slowly pulled my dick out of his mouth. He looked around wildly, realizing he couldn't stand up to spit and couldn't spit it onto the toilet seat. "Just swallow it." With an effort, he complied, but looked up at me rather unhappily. I stroked his hair and smiled at him. "That was great!"
I dropped my hands onto his shirt and started to pull it up. "Raise your arms" I pulled his shirt off and got my first actual look at that hairless torso. I felt him up, enjoying that natural smooth feel. This boy definitely didn't need to shave his chest! "Undo your pants again." I really liked the way he complied with almost everything I told him to do. I wondered if he was that way with the girlfriend he'd told me about. "Okay, now pull your knees up to your chest." I pulled his pants and shorts all the way to his ankles. I debated stripping him completely naked, but decided against it. He was already semi- erect again.
I pulled off my own shirt, dropping it into the floor on top of his, and I fished the lube from my pocket, setting it on the sink before pulling my own pants down to my knees. I held my hands out to him, helping him up, which brought him right up against me, into my arms, pressing our dicks together. I took this opportunity to kiss him, sliding my tongue into his mouth. Again he made his soft muffled expression of surprise, but, again, he let me do what I wanted. I kissed him for a while, one arm around his shoulders and the other in the small of his back. I enjoyed feeling his naked warmth against me, and I enjoyed feeling his silky smooth skin under my fingers.
"Turn around and lift the lid. I'm going to try to make you shoot in there." He stumbled around, leaned over the toilet to raise the lid, and then stood back up. I wrapped an arm around his waist, grasping his still-sticky cock and started slowly stroking it. With my free hand, I picked up the lube and squirted some into his crack, then started rubbing it up and down across his asshole with my finger.
"How's that feel?"
"Good." He whispered.
I kept working his cock and his asshole at the same time. Eventually I had a finger all the way inside him, which I started slowly sliding back and forth. Then I stopped stroking him, put some lube on my cock, and started sliding it up and down his crack. Finally I positioned my dick against his asshole and pressed gently, one hand gripping my dick, the other wrapped around his chest and gripping his shoulder.
"Is this safe?" He made no move to resist me, just the simple, soft question. I kept increasing my pressure.
"Anyone ever do this to you before?" I felt my cock slowly starting to slide forward into him.
He simply shook his head no. I kept a tight grip on him, and controlled the speed of my entry. VERY slow and easy.
"I didn't think so." I smiled. "Yeah, I'm safe. Just try to relax and enjoy it." Not very responsible of me, I know, but it was the truth, and for some reason I really, really wanted to bareback this boy. Anyway, the head was far enough in that I didn't need a hand on it to guide it, so I let the other hand go to his crotch. He had started to lose his erection, but immediately perked up on contact with my hand.
"Easy, easy, easy" I whispered into his ear. A millimeter at a time, I felt myself slowly, slowly invading him. No protests, no spasms, I silently complimented myself for doing a first-rate job with him. As I felt the head of my cock enter his anus, I nibbled his ear and whispered, "almost there." I heard him breathe a little heavier as I slid up his chute and then deep inside him, but no sharp intake of breath or tensing to signal serious pain.
I realized he had his head to the side watching us in the mirror. I thought it was interesting that watching a man take his anal virginity turned him on, and from the feel of his cock in my hand, he was very turned on.
Once I was as deep as I could go, I started slowly pumping him with short, deep strokes. Abandoning his cock for a bit, I held him tightly with both hands on his hips. He braced his hands against the wall, leaning forward and gripping one of those handholds. As he loosened up, I started pumping him faster and taking longer strokes.
This was really heavenly, and although I'd just cum not long before, I soon felt myself tumbling over the edge into another orgasm, filling his rectum with another load of cum. Once I was done, I slid as far into him as I could go, took a shuddering deep breath, and said, "God, that was good." Then I kissed him on the back of his neck and reached back down to his cock, still fully erect.
He shot almost immediately, mostly into the toilet.
I carefully pulled myself back out of him, and told him to sit on the toilet. He did so, but I saw he had that frightened look in his eyes again. I calmly pulled my shirt back on, then pulled up my shorts and jeans, adjusted my hair in the mirror, etc. I got my pants fixed again, washed my hands in the sink, and told him to wait a bit, then come back to the seat. "Keep my load inside you, if you can. I like thinking about how it matches the one in your stomach." He blushed bright red and I grinned some more.
I carefully stepped out of the lavatory. Still no one around. I heard him latch the door again, and I walked calmly back to my seat. The girl in the aisle was still asleep, and I stepped over her and back to my place. After a minute, the boy came back and did the same. We both leaned back and tried to sleep some more, my leg hooked around his, and his hand in mine.
As we approached the airport, I asked if he needed a ride, but he looked a bit concerned and told me he had friends coming to pick him up. When they unloaded the plane, he got separated from me, and disappeared into the crowd.
--The End