My best friend Andy and I talk about sex all the time. We know all about one another's experiences, likes and dislikes, and habits in general. We know we both masturbate like crazy. We know we've done it in the same room, in the dark, at the same time before falling asleep, and it's been ok, but we've never been really deliberate about it, and we've never actually seen one another do it.
There are a few things Andy doesn't know, however. He doesn't know that I love the sound of his masturbating more than anything in the world. I lay awake many nights waiting to hear him stroking himself. It's almost always the same sounds: First, the creaking-clicking of the lotion bottle open and closed. Next come the snaps on the pyjama pants he always wears, one, two, three and then I know that his beautiful cock is out and he's beginning to give himself the most incredible pleasure. That sweet, slippery rhythm of his puts me in a trance, and my own hands do their work automatically. Sometimes I jerk myself quietly, concentrating so I can come at the exact same moment he does. Other times I want to let him know that we're sharing the same intense pleasure and I let out the occasional grunt or heavy breath.
One thing for sure he will NEVER get to know. I have never felt so guilty about anything, and maybe never will. One afternoon, three years ago, he left me alone in his room while he ran over to a neighbor's. I was really horny, and everything in the room, his clothes, his bed, his smell, made me imagine his jerking off. I went crazy and started digging through the mess for any little bit of evidence. In between the bed and the wall I found them, the pyjama pants. I undid the snaps, running my hand over the crotch, as if he were in them, then quickly put them back in their place. Then it hit me, of course!
Under the bed I found exactly what I had never hoped to touch, a pair of beautiful boxer shorts, crumpled and stiff with dried cum. I shook as I sniffed them and was practically screaming at myself not to do what I was already beginning to do. Not knowing how long I had, I freed my throbbing cock and began rubbing it furiously with my best friend's cum-loaded underwear. I was thrusting in and out of the fly hole and feeling like I was going to explode. Something made me panic, though, perhaps it was knowing that he could return at any moment; perhaps it was wondering how he might freak out when he went for his cum rag later and found it soaked with what he knew couldn't possibly be his own spunk. Some of my pre-cum was already leaking onto the boxers so I immediately put them back and finished myself off into the garbage can. That was one guilty orgasm. How could I betray my best friend like that and invade his privacy like that? He knows me better than anybody, but he doesn't know he's my greatest fantasy.
Reading some of the stories here have made me think though. Someday I might just ask him if we can masturbate together, out in the open, no sneaking, no guilt. Someday maybe. For now, I breathe his name when I come, and I never feel guity about that.