I don't know why I've been afraid to ask friends if I can jack them off...we both end up loving it!
I am generally straight in my sexual preferences, but occasionally I am overwhelmed by the desire to play with another man's cock. This probably is the result of having played with my best friend's penis from the onset of puberty until he (but not I) had a full tuft of hair surrounding his balls, and he ejaculated gobs of cum over my hand.
I was ashamed in my teen years to admit to masturbation and certainly not to wanting to stroke another boy's penis, even though secretly in my warm bed I recalled certain boy's cocks I had seen in the locker room and brought myself to orgasm imagining that I held, not my own, but the other boy's cock in my hand.
It wasn't until college, with my own apartment and both freedom and secrecy, that I allowed my urges to spring forth again. I cautiously mentioned masturbation in casual conversation with other guys, and, after many pointless hints dropped too many different boys, found myself engaged in actual talk about jacking off with a boy in one of my classes. That weekend in invited him over to my apartment on some pretext, and continued the conversation, with one goal in mind. That goal was achieved late at night, when finally he asked (I was too scared) if I wanted to jack off, and we both took down our pants. Once I saw his naked crotch, covered with thick red hair, and filled with huge balls and an attractive, swollen cock, nothing could stop me from holding his penis in my hand.
It felt so different than my first friend's little stick, and his orgasm was powerful and massive. I remember little of the event, really, except the raw strength of his cock in my hand. For the next year though, I got to know and explore the amazing landscape between his legs, and my touch on his cock became delicate, strong, smooth or hard, as his cock demanded and craved. Although sometimes the urge was overwhelming to have him strip for me and offer his cock for masturbation, he came to my apartment only when he wanted, or craved, my touch.
There have been others, only a few, and none so exciting as my college friend, but recently the urge struck me again, and my wishes were unexpectedly fulfilled by someone who I secretly masturbated thinking about, but I never imagined would actually allow me to touch his cock. This man is a consultant to our firm, and I meet with him almost weekly at his home/office. He has always been friendly, and appropriately business like, but when I unexpectedly visited him on a weekend, he was in shorts that showed signs of cum or precum, and was noticeably different in other ways, flushed face, distracted, a little nervous, and exceedingly friendly. His handshake was soft and, now that I think of it, sexual. I immediately felt horny, and all the while we did our business, I could not get thoughts of touching him out of my mind.
After we finished our work, he offered me a beer and we chatted a while. I had the presence of mind (or desire) to turn the conversation to photography, a shared hobby, and from there to photographing nudes, and he became more and more animated. He had a large collection of his ex-wife, which he pulled out and showed me. She had a tremendous body, and was an awesome model, and when I said that, he lamented that she was gone, and said now he can only jack off to her pictures. Bingo, the JO word struck me like lightening, I jumped to say more, and a hurried, nervous, whirlwind exchange followed. Within ten minutes we were sitting naked on his couch. He became calm, slow and gentle, and I relaxed, except for the burning desire to reach over and grab his cock. He was very well endowed, something I'd already noticed, but what I wasn't ready for was the size of his balls, which were as big as any I ever imagined, and his light pubic hair not shaved, but thin and wispy, making just a faint ring around his gorgeous equipment. He talked continuously and quietly about sex and women and whatever as we stroked, and I fell into a comfortable and very sensual kind of edging. On the tip of my lips, though, was the urge to ask if I could masturbate him, but I couldn't bring myself to say it.
Suddenly, he was about to cum, and he let go of his cock, trying hard to regain control in order to continue edging. He held his hands away and for the longest time, his cock stiff in the air, quivering on the verge of ejaculation. I reached over and grabbed his balls, squeezing them hard, and he let out a large grunt as he returned from the edge. I held his balls, hot in my hand, for at least a minute, and then began stroking him. In a short while, he was out of his mind horny, squirming on the cushion, but I gripped his cock tight and held him on the verge of orgasm for another half an hour before the urge overcame me to feel his hard, red, sore cock twitch in my grip, and with a few quick strokes, he began to ejaculate gobs and gobs of cum, moaning without stopping until finally he was quiet. I stood and quickly masturbated myself to orgasm, adding my cum to his on his belly.
We've met four times since that weekend, and now we allow time at work to jack off together after we're done. Sometimes he won't let me touch him, but when he does, it means he's really horny and his balls are full and ready to shoot, and I'm always willing to help. I forgot how much I crave holding a cock in my hand, and I'll never do without again.