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My absolute hottest experience was with a random dude off CL .. I went further than I thought I would
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Remember Craiglist personals? God, I miss those. This happened to me just a few months after my divorce (from a woman), at a moment when I was re-evaluating almost everything about my life. I decided to indulge my curiosity, nervously and with great secrecy, to find some like-minded dude to, at the very least, watch each other jerk off. Maybe something more.

After a lot of false starts, flakes, and the rest -- why oh why aren't there more normal people out there? -- I connected with this attached dude who lived downtown. Turned out we shared similar tastes in porn (schoolgirls, MILFs, huge cocks naturally, sloppy BJs, gangbangs), had similar situations (curious, a bit experienced, but with a lot of guilt, discretion, safety guarantees needed), and similarly filthy minds (our texts got really, really, INTENSELY heated with open-minded fantasies I'm not sure I can repeat here).

After a few weeks of texting back and forth, and exchanging cock pics but not face pics (I was game, but because of his live-in GF, he was understandably nervous, and there was no way I was going to pressure him that way), his GF had a weekend out of town. (Oh yeah, he was comfortable enough to share clothed pics of her for our fantasy pleasure ... god, what a fine piece of ass. A true ginger beauty that got me hard instantly.) So, tonight was going to be the night. I was nervous as hell. Hard as a rock. I made my way over there, with both of us agreeing to just watch some porn, watch each other, no touching.

I get to his condo, and he's nervous as hell. But also happy to see me, as I can soon tell by the bulge in his jeans. We agree to throw on some porn -- our absolute fav clip, a Brazzers scene of Faye Regan and Nikki Rhodes as schoolgirls in a threesome -- and we nervously pull out our dicks. Mine is a nice cut 7.5 cock, a bit veiny, with a perfect mushroom head, if I do say so myself. His is a bit shorter, but a little thicker, and most importantly: cut like a beauty.

We both start jerking, going slow and steady as to nut bust a load, which I know at this point could happen any second if I lost control. We inch closer to one another. He asks if I mind whether he takes his shirt off, too. I say, sure, why not? I do the same. I'm a hairy motherfucker, but this guy (he's Asian) is nearly hairless. Chest cut like movie-star abs, almost. I admit, I don't usually give a shit about what a guy looks like body-wise -- I'm just here for the cock -- but I was intrigued. He seemed to dig my body, too. So much so that he asked if he could touch my chest. I say go for it. Well, I whisper it more like ... at this point, my throat is pretty dry, I'm so horny and nervous and excited all at once. My cock is throbbing. The porn in the background is just distant noise.

I feel his warm hands going across my chest, almost petting me, rubbing my chest hair like fur. Then he begins to gently run his fingers along my nipples. My god! I don't even say anything, don't ask, but move my hand over and grip his cock. Without exchanging a word, he does the same -- one hand jerking me, the other flicking my nipples. We're close now ... closer than I've ever been to another man. I can smell him, nearly taste him. We lock eyes. And then he asks if we can kiss.

Whoa. Again, I never ever had desire to kiss a dude. But at this point I'm locked in. Why the hell not, I say to myself, and we go for it, all the while our hands pumping each other ... slowly, again, because we both know we'll explode soon. The kissing was ... pretty damn good. Like a woman, but slightly rougher, or less delicate at least. It wasn't AMAZING but it was interesting. And the entire experience of it ... the kissing, the nipple play, the jerking ... it added up to something close to mind-blowing.

We kiss a bit more forcefully now, really letting our tongues gnash against each other, our mouths aggressively smacking into each other, and then I can feel it start ... I can feel my cum about to rush out. I pull back and say I'm going to fucking cum, and he says, "fuck yes, me too." I shoot a giant rope onto his chest, and then more. Honestly, I'm not a huge cummer, but this feels like the biggest load of my life. Not one second later he does the same, most of it landing on my dick, too.

We both fall back, exhausted, laughing. We cool down. There's an awkward tension in the air. But then we have a beer each, both of us back in our underwear (boxers for me, boxer briefs for him). And then I ask about his GF, and we get hard right back again. And the story goes on more from there, which maybe I'll one day share.

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2 years ago