When I was in college I was dating a beautiful girl who was sexy but a little prudish. We often spent weekend nights together in my little apartment (which was over a garage in the student rental area of town.) We would put on records and kiss and make out for hours at a time - pretty serious kissing, as far as it went. I was hard practically the whole time, but never had much relief until she left and I could jack off. We didn't discuss sexual things much. She would have been shocked to know how much I masturbated - three or four times a day most days.
Over the summer we finally advanced to sleeping in our underwear together, and once in a while I would get to feel her tits through her bra. One night when we had been kissing for a long time, I managed to manoeuver my body on top of hers. My hard cock pushed out my briefs and was lodged against her panties. I kept my mouth on hers, tonguing her pretty deeply, and slowly slid the length of my cock along her pussy, two layers of underwear between the flesh. At first she let out a little gasp of pleasure, but she pushed me away and said, 'no, we can't.' I rolled off of her in frustration, and lay on my back with my hands behind my head.
The lights from outside shining in the room were enough to illuminate us a little. I pulled off my underwear and said, 'I have to let this guy breathe,' not caring if she were offended by the sight, and secretly hoping she would be either aroused enough or feel sorry for me and do something with it. It was definitely the first time she had seen my cock, albeit in poor light; but it was enough to tell what I had. She let out another little gasp and said, 'It's so big!' It was big - she would have been shocked again to know that I had measured it with a ruler and that it was exactly eight and a quarter inches. She said, 'I can't imagine that ever going inside me!' I'll bet, I thought. But I could, and I often did. In my jackoff fantasies I had squirted the inside of her pussy hundreds of times, not to mention cumming all over her tits and down her throat. But now I was hoping for a handjob - all she would have to do was stroke it up and down a few times, and I would paint the ceiling with my cum. Already, in the dim light, I saw a drip of precum peak at the top and slide down. 'It looks so hard,' she said, and kind of put her hand on my thigh near it. I quick scooted so that my cock would be where her hand was, but she giggled and moved it away.
We then played a little cat-and-mouse game where I moved my hips and she moved her hand trying to avoid touching my dick. Finally she let herself 'lose' and she loosely held my shaft. 'Oh fuck,' I thought, 'here it comes!' 'Ooh,' she said, 'it's so hard, but the skin is so soft!' She then lightly ran her fingers along the shaft, and then up over the cap. I sucked in some breath sharply and said, 'Ohhh.' She pulled her hand away then and started to talk about her family vacation! She was leaving the next day for two weeks in Europe with her family. I couldn't believe it! There was precum flowing out of my dick, and she was done for the night. I almost jerked myself off right there. I didn't say anything back, and she fell asleep soon after that. I could have beat off then, but I was still hoping something would develop.
I awoke with the sun streaming in the apartment, I was lying on my back, no covers on. She was standing in the middle of the room with her clothes on, ready to leave. My cock was in a half-hard, heavily-weighted phase, snaked across my leg. Without attempting to hide myself, I went over to the bathroom, shut the door and pissed. I would jerk off after she left. I put on a pair of gym shorts and carried her bag down the outdoor steps to her car below. She gave a lingering good-bye kiss on the steps that got me half hard again. I waved to her as she pulled away, the outline of my boner already showing in my shorts. I walked up the steps and had my shorts down and was in the bathroom almost right away. Just a quick squirt in the sink for now - I could linger over the memory of her touching my cock later. Right now I needed relief.
Even as I was just about to start stroking, there was a knock at the door. Shit! She had forgotten something. I quickly wrapped a towel around my middle, but it wasn't very effective. Well, she would have to deal with it - and the more she knew now, maybe the better. But when I opened the door, it was Mike, a guy who lived in the apartments in the main house. He was holding out a pan of mine that he had borrowed the week before. 'Hey,' he said, 'I saw your girlfriend leave and I thought I'd ...' his eyes went to the tented front of the towel, and he said, 'Wow!' And then he looked up at my eyes and said, 'I thought that beautiful girl would have taken care of that problem!' He said it in a good-natured way, so I just smiled back and said, 'She's a beautiful girl who *doesn't* take care of these problems, so I have to.' Mike laughed easily and leaned against the door. I didn't know him too well, but he seemed like a cool guy. So I explained awkwardly how she had gotten me all hot last night, even to the point of slightly playing with my cock, without getting me off, and that was why I was dying.
Mike stared in disbelief and said, 'You mean she had a hold of your dick and wouldn't jerk it off? Was it good and hard?' Now it was my turn to laugh, 'Hard as steel and dripping precum,' I explained. 'Jesus,' Mike said, 'It's getting me hard just thinking about it,' and he tugged uncomfortably at the front of his shorts where a visible bulge was growing. I started telling him the details, how I had rubbed my cock on her panties, how she had asked about the size, how girls didn't understand anything about a guy's need to get off a couple of times a day. As I spoke, the towel slowly fell away, and there I was taking to him with my cock pointing straight out, a string of precum extending almost to the floor. 'Damn,' he said, his eyes glued to my dick. Without a word, he pulled off his own shorts, and went onto his knees as I went onto mine. I put the towel on the floor between us. He put his hand on his cock and said, 'Girls have no idea how we need to cum,' and he started stroking slowly.
I lightly touched my dick - it wasn't going to take much. 'Yeah,' I said, 'I'm going to cum, finally.' 'Me, too,' said Mike. I stroked and said, 'I wish this was her giving me a handjob.' 'Me, too,' Mike repeated. He then looked like an idea struck him. 'Hey,' he said, 'get back on the bed just like you were last night when she was touching your cock.' I got up, walked over to the bed and lay down on my back, my hardon pointing to the ceiling. Mike got in next to me. 'Close your eyes,' he said, 'and pretend this is her.' I did, and he lightly touched my dick. It felt great. He ran his fingers lightly along the shaft and up across the top of my cock. I let out a small groan, but this time the hand did not pull away. Very lightly, the fingers and the palm loosely gripped my shaft, and then slowly moved up and down. The top of his hand grazed across the crown of my dick, and the sensation of rising cum shot through me. 'Oh God,' I moaned, 'Oh jack me off, make me cum, oh please.' The pressure of the hand increased just slightly, pulling the skin of the shaft up and down with gentle strokes. The speed increased a bit. This was a hand that knew what a cock enjoyed. The speed and intensity increased a bit again, the circle of thumb and forefinger tightening slightly as it rubbed up and down over the head of my cock. 'Oh, yesss ...' I breathed out as a preliminary squirt shot out, thin and strong; 'Uhhh' with the next, a massive explosion of white cum, a missile that flew high in the air. By the time the white goo splashed on my stomach, the next squirt was on its way, then another, and another, and all that time, Mike kept pumping like a pro. He slowed as the squirting stopped, but he kept at me until I was milked out and my hard, hard cock was just slightly less hard.
'Thanks, man.' I said, with a great feeling of relief. Mike smiled and lay back. He didn't demand anything, but I immediately did the same for him. He hadn't been in my state for quite as long, so it took him a little longer, but not too much. He unleashed his load all over both of us. We lay there for a while, laughing at what had happened. We talked about girls, about beating off, about all kinds of things. Within 20 minutes, we were jacking each other off again. It was a great summer.