Back in the heyday of Craigslist's NSA personals, I replied to an ad placed by an older male—I don't think the ad specified age—seeking a "young stud" to have a three-way with his ebony sex friend. No pictures in the ad, but it seemed real.

I threw my hat in the ring, cock and body photos attached (you can see in my post history as well), and I got a reply! After a couple messages he let me know the hotel , room number, and the time. It was a bit farther away than I'd anticipated based on the map shown in the posting, but the hotel was right off the highway so pretty convenient. I end up getting there much sooner than anticipated, at least an hour before our planned time, so I hit the sports bar in the strip mall across the access road. I always get a bit nervous when I do these kinds of things, so I order a pint of IPA to take the edge off. I've come straight from work, on an empty stomach, so you get that a good buzz before you even finish your pint, which is a feeling I enjoy. I'm a quick drinker, and the glass is empty with still a lot of time left, so I order another and do my best not to gulp it down too quickly. The clock hands on my watch are moving so slowly... Now I'm feeling pretty good and I'm ready to fuck!

Finally it's time, so I drive the 50 meters from this bar to the hotel parking lot. Walk in and head up to the room number and knock on the door. A tall, white haired dude in business attire, probably around my dad's age, greets me and asks my name, I guess making sure I'm the person he's meeting. I confirm and he says come on in, and apologizes that his friend isn't there yet. I guess she's running late. She's in town for a friend's... Bridal shower I think it was? And it had gone later than she expected.

Okay, so we wait. And wait. I've been stood up by women who chicken out of something like this. Also, I was once tricked where the men who invited me just wanted to do guy on guy and I don't think there was ever a girl who was going to come in the first place, so I was halfway thinking this old dude was gonna ask me to whip it out... But he didn't! He was really friendly and polite. We chatted about classic rock. He tells me she's on her way now. He's going on and on about something, I'm only halfway paying attention... Actually my eyelids are starting to feel a little heavy...

Knock knock knock!! My heart jumps, those loud ass knocks startled the shit out of me. Old timer opens the door and in walks tall, curvy, black woman with a pretty face, long, straightened hair, in a low-cut black dress, holding a handbag with flowers spilling out. She's probably right between myself and the older guy in terms of age. "I'm so sorry for keeping you waiting!" Honestly, I am kinda surprised that she even showed up, and now I'm very excited to get my hands on this sexy ass woman.

Old guy doesn't waste any time, "So should we get started?" Okay! She starts kissing him and moves my hand into her breast. I take it out of her dress, well it practically fell right out, and old timer does the same, so now we are sucking on her big, dark nipples... But only for a second, because now this guy is taking his pants off. I do the same. She takes off her panties and hikes up her dress, and starts sucking him while stroking me. Then she switches over to sucking me—and it's pretty great. "Damn, you got a nice dick!" ... You know, I never get tired of hearing that, lol. Wow, this old dude really is not into foreplay, because before she can even give him another suck, he's strapping on a condom and next I look he's already fucking her! She's moaning a little while she's sucking me, and he's pounding away.

Suddenly he gets off her and just stands there watching us. "Why did you stop?" I ask him (her mouth is full at the moment). "I came!" He tells me. Really? His cock still looks hard to me, and we hadn't been going very long, I can't really see any cum in the reservoir tip... Whatever! He takes off his condom and is getting dressed while watching us. I'm really, really enjoying this blowjob, to the point that I'm not even that interested in fucking. I'd rather just have my cock worshipped, and she's doing a fine job of it. After a few more minutes, I'm ready to cum.

"Can I cum on your face?" I ask her. She tells me no way, but she's nice about it. But I really like to see my cum fly, so I ask her,What if you jack me into mouth?" — "I ain't fallin for that one! You're gonna cum on my face."... She's onto me, lol.... I tell her, "You can aim it into your mouth!" But she says "You can't aim jizz." I laugh. There's some truth to that. I say to her, "Okay, okay, but you can't blame a guy for trying!" She laughs, and then starts sucking fast and hard, and it's not long before I'm pulsing and cumming into her mouth.

She swallows. She waggles my still engorged cock and says "You know I got some friends that would really like this. I'm gonna tell them about you." Sure! Please do!

Older guy is all dressed and ready to go. I start getting dressed, too. He tells her to enjoy the room, says we should all do this again sometime, says goodbye and leaves, and then I do the same. Guess she gets a free hotel room for the night out of this arrangement. She earned it.

Unfortunately, I never heard from either of them again. But it was a fun time!