I was partnered up by the time Grindr came along, thank fuck. But about 20 years ago, I was mid-20s, living in a small city on the West Coast that had no gay bars, and rarely any good prospects on Craigslist. I was desperate for cock and so, late one night, I headed down to a park area that I knew to be a cruising spot. Sat in my car for a while until I saw a dude sort of loitering nearby, completely obvious what was up.
He was older maybe 10 years older than me, not super hot but not obviously disgusting - balding and dressed in bland clothing, looked and dressed like an insurance agent or a public schoolteacher. He worked his way over to my car, and I said, "Get in if you want." He did, we drove to a more secluded area and he pulled out his dick. It was shaved, which I didn't care for, but decent sized, so I went down on him. After a few minutes he said, "Let's go to your place." I stupidly obliged.
We get to my house. In the light, I notice his features are a bit ... harder looking than initially realize. But we're there. He asks if I have any porn, so I pop some Bel Ami in the VCR (sue me, I was in my 20s). He asks if I have any straight porn, I say no. We take our dicks out and start fondling each other a bit, but he's staying soft at this point and seems listless and not into it. I want to at least get an orgasm out of this, but realize I have to pee. I tell him I have to go to the bathroom and will be right back, step out of my pants, leave them lying on the floor and leave the room.
I come back and he's fully dressed again and standing in the living room. "I'm going to head out," he says. OK, I'm actually relieved at this point. I lived in a semi-rural area, and ask if he wants a ride back downtown or somewhere else. "No, I can get home," he says, and quickly leaves.
He's gone. I pick my pants up off the floor. Ohhhhhhh fuuuuuuuuuuuck. My wallet is gone from the back pocket. I rifle through my house, thinking maybe it wasn't in my pocket. But I knew it was. The fucker stole it!
Weird coda: maybe two weeks later, my credit cards canceled, my new driver's license on the way, etc. - a padded envelope arrives in my mailbox, my name and address scrawled on the front with a Sharpie. It's my wallet!! With everything still in it except the maybe $8 in cash that was inside at the time. So weird.
Given that I brought a petty hood inside my house, things could have turned out a lot worse, I guess. But I always had this small fear he'd show up back at my place some night. He never did.