kinda long, but... I like this story...
The setup: I'm a bi high school girl. For a number of years I've had mostly guy friends; I wouldn't really say I'm a tomboy, but my interests are more like those of young males so I flock to them. Naturally, like any teenagers, we talk about sex and masturbation a lot, but I usually don't fool around with my friends, because to them I'm 'just one of the guys.'
About a year ago, we took it into our heads to have a 'contest' as in that episode of Seinfeld, in which we would see who could go the longest without masturbation (and, again as in Seinfeld, relying only on 'the honor system'... I mean, how else would we do it?) Not that we thought jacking/jilling off was wrong or anything; just a fun competitive thing, like who can hold his/her breath the longest (for me, those things are about the same timespan.) Actually, our rule was no orgasms period. Since we weren't betting money, we figured it would be pretty honest play as no one had anything to lose but a little pride.
About five days into this contest, I was at the movies with my friends. One of my female friends, who was not in the contest but did know that I was, started messing with me for the sake of making me lose. She kept taking her fingers and stroking the insides of my thighs up and down with delicious, torturous slowness. Whenever she'd pause briefly, I'd start yelling at her (in a good-naturedly grumpy sort of way) but while she was touching me all I could do was sigh and moan softly. She found all this very funny and continued unrelentingly. I felt like liquid fire was spreading through my legs and stomach; I could feel how slippery my neglected pussy was getting, and my clit throbbed for attention. She got a little bolder and massaged my crotch through my jeans. Losing control for a moment, I thrust my aching loins at her with a groan. She stopped, still laughing. I was both relieved and disappointed. I took a few deep breaths, and the evening proceeded as normal.
That night, she and several of my other friends (including the boys in the contest) came back to my place to hang out. There came a time when we were all laying in the dark listening to music, a common activity for us. One of my guys, one I found extremely attractive, but a very sexually inexperienced one (which attracted me even more) was laying by my side, head-to-toe with me. Partly in lust, and partly for the sake of 'making him lose' as my other friend had done to me, I decided to have some fun. I lifted up his shirt a little and started rubbing his belly. I dragged my fingertips lightly across his smooth skin, making little circles around his bellybutton and tracing the curves of his ab-muscles. He lay still, but a deep, slightly ragged sigh let me know he was very aware of what I was doing. I nudged at the band of his boxers with my wandering hand, inserting my fingers millimeters inside to make my intentions clear. 'Having fun?' he said calmly. 'Yes,' I said, knowing this was him saying, 'Go ahead.' I mimicked my girl-friend's motions, stroking and tickling his inner thigh. He writhed slightly, but we didn't dare do any more than that until my other friends had gone.
Enter fifteen minutes later, when the room had more or less emptied. I moved my hand to his crotch, rubbing, feeling his bulge. He moaned very softly. As I felt his erection through his jeans, I got dizzy with arousal. I felt empowered, in control. I was even more turned on when I looked at his face. His eyelids were half-closed, and his eyes were rolled back in pleasure. 'That's really good,' he said, seemingly to himself, as I massaged his hard-on. I unbuttoned and unzipped him very slowly and peeled down his pants and boxers. His chest rose and fell rapidly now. This boy was quite small of stature, but he had an intact erect penis at least six-and-a-half inches long. I was surprised. I cupped his almost-hairless balls gently in my hand, petting them like little animals. Still rubbing them with one hand, I ran one fingertip delicately up the underside of his cock, trailing off at the tip. He grunted restrainedly. I then used all my fingers to stroke upward on his foreskin and head, repeating a soft pulling motion, as though drawing him to greater lengths. He moaned and spread his legs spastically, as though begging for more. I could feel him throbbing in my hand. By now I was ready to have an orgasm myself; I'd never been so horny in my life. I stroked him up and down, sliding his foreskin up and down over his head, enjoying the precum spilling over my fingers. When I thought he was about to come, I abruptly stopped and took my hand away. His breath was ragged; he stopped mid-groan and looked at me questioningly. I very slowly and softly started the stroke again. 'Oh God,' he grunted through gritted teeth, 'I'm gonna come.' But I kept at the slow pace for another twenty seconds or so, until he was going so crazy I thought he might start crying, at which point I started jerking firmly and quickly again. The look on his face when he came was the most erotic thing I've ever seen. His mouth was open in a silent scream, and his eyes were closed in a pleading sort of expression. He shot a huge load of cum onto his chest; it dribbled onto his neck and belly, and I'd licked most of it off before he'd recovered from his mind-blowing orgasm. I took his hand, kissed it gently, and said 'Thank you for sharing that experience with me.' He gave me an affectionate 'what-the-hell?' expression, and I helped him up.
We called the contest a draw. None of us could take it anymore, least of all me. You can bet I masturbated myself silly that night (a story, perhaps, for another time.)