He did it for a dare. His girlfriend had a chrome one from one drunken girls night out, and when she called him a pussy for being afraid he lubed up that slim vibrator and let her push it into his tight butt. Then he screwed her for two hours until the buzzing in his gut pushed him over the edge. I don't expect she would have been so keen to have him try it out if she'd know where it would lead.
His name is Matt. He spends most of his day behind a computer in his office, but luckily for me he takes time every lunch hour to use the company pool and gym. He's kind of average-joe looking, but has great grey eyes and a big grin that lights up his face. Right now, Matt is sweating because he's on his back on the bed in his apartment with his hips tilted back over his chest. Right now he's staring into the eye of his hot hard cock, because Matt lost another bet and now his legs are up by his ears. He's not too flexible, but he's fit enough to handle being tied like this. The rules are simple. Up his ass is a slim vibrating prong, smooth at the next but slightly wider and bulbous at the head. If he stops gripping with his tight ass muscles, the dildo will slip out onto the bed. However, the switch to the dildo is in the neck of the toy. As long as he grips, the rubber invader shakes and twists against his prostate and sphincter. And every time it springs into action, he grips even tighter in reaction and draws the slim stick back up into his ass. Matt has been trying to relax his ass enough to get his butt free of that unrelenting pressure for about forty minutes now, and a patch of precum has formed on his chest. He can't get quite enough friction to cum either, and his brown floppy fringe keeps falling into his eyes which sting with sweat. He grits his teeth, determined to win, but then clenches ever tighter. He closes his eyes to enjoy the sensation then nods to me in defeat. I grip his six and a half inch cock at the base and lick hard along his balls. That triggers it, and he spurts into his face. When he's finishing spasming, he looks at me with dumb grin on his face.
We never would have hooked up unless his girlfriend hadn't got drunk on holiday and told me about Matt's little fetish at the bar. We were all getting hammered and telling stories that had got more and more dirty. She was flirting with me, I guess, but I wasn't interested in her. Not much later I helped Matt walk her up to the room they were sharing and dumped her unconscious form on the bed. She was okay, just dead drunk and would feel like shit in the morning. Nice girl. Matt and I went out onto the balcony and finished a few more beers. I don't believe in the magical transformation of the straight guy, but I do believe in the desperately horny straight guy. It isn't blind faith - I know he exists. Matt's girlfriend wasn't in any fit state, so an hour later I pulled out a pack of cards. In the pretence of poker, I won his shoes, socks, shorts and t-shirt. Two handfuls of suncream and I had him squirming in my hands, naked as the day he was born. His tight tanned body had the sexiest white strip where his shorts covered him. It was just two guys getting off, but I had a slick hand around his hard on and another up his ass crack.
So we got into playing games. He'd screw his girlfriend, then meet up with me later, down by the bar or out at the pool overlooking the beach. He liked seeing how long he could hold out before cumming and I was more than happy to oblige. Sun cream and a little sand made an unusually effective lube, and Matt spent more than one evening in a quiet corner of the beach with his short around his ankles as I made him pant like a bitch. Tonight he couldn't last the hour he bet me so he's going to spend an uncomfortable day tomorrow with a firm but flexible plug up his ass. But for now I have him on his knees, between my knees as it happens, with his arms tied behind his back. He would hold them there himself obediently, but I find that restraining him with one of his work ties adds a little something. I've slicked up his cock with a good handful of lube and his stiff prong occasionally brushes against the carpet. He has cock ring on (another of his girlfriend's purchases, I really must get around to expressing my appreciation to that fine young woman) and my hard dick between his lips. Neither him nor I are much into gagging when trying to deep throat and the angle is all wrong, so he's just running his tongue and lips around the top two inches of my dick. I'm watching TV and he has to stay there until the program finishes, swallowing my cum when I spurt. I reach forward and tuck a small ice cube from my drink into his tight ass portal. He twitches under my fingers and sucks harder.
I might let him cum again later tonight, but I think it might be more fun to visit him at work and crawl under the desk in his office to suck him dry when he's trying to make a conference call. Matt's a sweet guy and I'm going to enjoy every inch of him before he gets serious about his girlfriend.