A friend’s dad, topping a straight construction worker & exposing an intelligence officer: Gays share their wildest Craigslist hookups
These confessions have us shook.
Mark
Oh, the magic of Craigslist…
You never knew what you were gonna get!
Before geolocation apps, there was the personal section, where cruisers shared their stats, “A/S/L” and little else. The anonymity was part of the fun: few activities are more adrenaline-pumping than showing up to an unknown location to meet an unknown man, with only a grainy image of his member to go by.
How about we take this to the next level?
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While the intercourse wasn’t always epic, the stories certainly were!
With Grindr’s well-chronicled downfall, we thought it was the perfect time to look back at the halcyon days of the early aughts before the orange demon app. We’re thinking dialup, AOL emails, Mapquest.
The whiff of nostalgia is strong, just like our lack of shame! This week, we asked Queerty readers to their most memorable Craigslist hookups. Here’s what they had to say…
What was your most memorable Craigslist hookup?
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“At the time, I was recently divorced from a woman and lurking gay forums for life advice… until I discovered Craiglist personals. Turns out, there’s quite a few former heteros looking to hookup. I met this man in his 50s. It was raining and we met in front of a bar, but decided to go somewhere in his car. Next thing I know, we’re in a hotel room and I’m smelling the most delicious perfume on him (Terre by Hermes), and this buttoned-up guy is going down on me in a super small shower. He is still with his wife, so I stopped hooking up with him. But he helped me understand that I DO love men!” — Alexis in Montreal
This Craigslist story has it all: DL married men, a rainy meetup, lascivious acts. It’s time for us to find our own small shower–we need to cool off! We’re glad that Alexis’ Craigslist era set him straight… on the fact that he loves guys!
“The guy wanted to hook up but did not have a picture. He was 33 and had just ended a 13-year relationship, so I was wary. I gave him my email address, and one morning he messaged me that he was attending a business meeting across the street from where I lived. Could he stop by for a minute and meet, and if I liked him, we could get together that night? I agreed.
“About an hour later, he knocked on the door, and when I opened it, I about fell over. He was ripped; you could literally see his six-pack of abs through his tight shirt, and he was hot as hell. He told me he was having dinner with his mother that night and would be at my place around 9 p.m. At a quarter to 9, he called apologizing that he was running late and arrived at 9:30 p.m. … It was one of the absolute hottest hookups ever. It was the first time in my life that I had basically non-stop sex for eight hours.” — Michael in Miami
Wow. It sounds like Michael’s hookup certainly enjoyed his dessert… and then stayed for breakfast, lunch and dinner! Once again, this Craigslist tale hits all the notes: business meeting, hotel room, initial moments of doubt. Trust was paramount; Michael had no way of knowing this guy was actually going to show up. But he put himself out there, and then put out for eight hours.
We’d say that’s quite the ROI (we figured we’d keep with the business theme).
“I once answered an ad looking for guys who were down for group action at a suburban hotel. That led to monthly encounters of from about 10 to 20 really nice and hot guys who would do their thing starting at 6:00 p.m. We would call the organizer’s number starting at 5:00 p.m. for the room number. No attitudes. Just hot, uninhibited fun.” — Joe in Seattle
It seems like Joe and his pals were early adopters to Sniffies. We love! Perhaps they can receive some complimentary merch?
“I was in my mid-20s and snuck out of work one day to meet a business traveler in his hotel room. He was mid to late 30s and his photos were really hot—hairy, nice build, handsome. I got to his hotel and knocked on the door of the room he told me. I was really thrown off by the fact that the guy who answered the door wasn’t him. But he was also hot, so I went in. My Craigslist friend was on the bed getting pounded by another guy. So my hookup with one came with a two-man bonus. It was my first group. I never made it back to work that afternoon, and actually stayed in touch with one of the surprise men. We made more good Craiglist memories.” — AC in Chicago
There’s just something about Craigslist, hotels and group bangs that go together… like Thanksgiving and apple pie. ????
“It was Winter 2004 and I was visiting family back in my rural hometown. I posted an ad on the m4m Craigslist personals section. A guy claiming to be 30, mostly straight but with a ‘bi top side,’ was on a construction project from Alaska and staying in a motel with coworkers, so he couldn’t host. Pics were exchanged and he was very hot. To make it happen, I got a cheap motel room for the night. He came over and we went a couple of rounds, hung out for a couple of hours and had a very good time. He ended up being the ex-boyfriend of [information redacted].” — Ricky in Perry, Florida
We published Ricky’s story because it’s entertaining–hot construction guy, Alaska, cheap motel room–but omitted info about his (alleged) partner’s identity because we don’t want to get sued! (FWIW, we checked out Ricky’s hint, and it doesn’t add up. Fun story, though.)
“I really enjoyed hooking up on Craigslist. The most memorable one is easy. A guy posted that because of his condition, he was unable to jerk it. He wanted someone to come by and give him a hand. His picture was cute and his grainy d*ick pic intrigued me, so I replied. He lived in a condo downtown that was not too far from my office, so I figured why not? When I went to meet him, he was wearing sweat pants. He offered me a drink and then adjusted his chair so he was kind of laying flat. I lowered his pants and took his big d*ck in my hand and gave it a wank. I asked if it was OK if I jerked myself off, too, and I [ejaculated] right after him. Ended up going to see him a few times. He was really sweet.” — Michael in Chicago
That sounds like love at first wank! We’re glad that Michael’s generosity paid off…
“I met a guy on Craigslist who was bi-curious! We hooked up at my place and he wanted to top me. At one point he made the comment, ‘You look like you’re really enjoying this.’ I said, ‘I am.’ Then he decided he wanted to try bottoming. After warming him up, lil’ straight boy couldn’t get enough. After 30 mins, he wanted to try riding me for round two. Oh, the good ol’ days.” — David in League City, Texas
Is there anything more tantalizing to a gay man than taming a straight horse, and finding out he’s a big bottom? We think not!
“I met up with someone anonymously at about 2:00 p.m. The guy said he could host. I get to the place and it’s a mansion out in the woods. The guy comes out and he [works there]. He lives in a room at the back of the garage. We start fooling around. It’s rather impersonal, so I take a chance and try dirty talking with him in Spanish. We had been talking in English up to that point, and he’d been better at communicating when we were texting. He lights up at the dirty talk, and is like, ‘You speak Spanish?!,’ and starts getting more into it. I swallow him and he has me curl up in his arms for a little cuddle. It was very sweet. That was the thing with Craigslist was that it could be ANYONE and there could be these wild boomerangs in expectations—for better or worse. Luckily better in this case.” — Zane in Santa Rosa, California
Exactly. On Craigslist, it really could be anyone. Bonus points for the midday hookup, too. That’s real decadence!
“Oh, mine is fantastic. Back in the day, I had posted an ad on CL and got a response that was generally interesting on its own. But the kicker was that he had sent me my own X pic. I was actually flattered that someone else thought my headless photo was hot enough that it would work for them as well. Somehow, the conversation actually continued (with a weird moment where he insisted that it was his own pic) and we met up. Turns out, he was absolutely my type. We met up and the sex was fantastic. Still in the top 10 of compatibility in bed.
“In our pre- and post-coital chatting, he was cagey about who he was. We were both attached to others (he was married to a woman). But somehow, it seemed more than the usual ‘straight guy trying to be anonymous.’ He mentioned that he used to live in D.C., and then commented that he knew some folks in the intelligence community. It raised an eyebrow.
“The next time we got together, I made note of his license plate number. Basic Detective 101. Within 15 minutes after he left, I found out everything about him, just using available web resources. I had read about this a-hole. While not a household name, he had been extremely high ranking in one of the U.S. intelligence services. Much more than just ‘knowing some folks.’
“I sat on what I had found for about a year. His politics were completely opposite of mine, but the sex was really, really good. Electric and passionate in a way I’d never had before or since. So I kept my mouth shut. Which was hard, to be honest, as he, over time, would mention things like where he worked, went to college, etc. All I could think was, ‘Yeah, I know.’ I probably could have figured out who he was just from triangulating those comments. He was incredibly bad at keeping a cover.
“After about a year of play, upcoming moves and job changes for both of us made it clear that our time was pretty much over.
“With nothing left to lose, I texted him, just to see what would happen. Of course, he freaked out and immediately wrote back, arranging for a special trip to my part of town. We met for drinks where he ended up telling me, unprompted, his side of all of the stories I’d read. Of course, in his versions, he was the good guy (he wasn’t). He asked me how I figured it out (I was vague), but he told me I was the first guy to have ever figured it out.
“Oh, no, dude. I was just the first one who told YOU they did. We haven’t talked since that meeting.” — Sean in Minneapolis
OK… this story has too much! From our vantage point, the guy wanted to be caught. For a high-ranking intelligence officer, he didn’t seem to hide his identity very well, right down to showing up in his actual car. Nice sleuthing, Sean! But we think the specter of getting busted may have been part of his thrill.
“I was chatting with someone in my area for a week. We were both apprehensive. I was 19 and he was older. One day, we decided to meet and hook up in the restroom of a local park. It turned out to be my friend’s dad. I was hooking up with his son at the time! The dad was shocked, but we were both horned. We hooked up all summer through the winter until his son found my school ID in his dad’s car. It was crazy for a few months. The dad finally came out and got a divorce. Now the son identifies as straight and the dad is gay. Go figure (and yes, he had the better d*ck). Those were the days.” — Daniel in Pasadena, California
Another classic… the friend’s dad! Apparently, it doesn’t only happen in cheesy adult vids. With tales like these, it’s probably a good thing Craigslist shut down its personal section. Nobody needs that!
“I replied to an ad from a super hot guy who showed his ripped torso in his listing. I knew he would get a ton of replies, so to stand out I didn’t proposition him. I teased him with a comment instead. “You seem cocky, boy.” He replied with an LOL, we traded emails, eventually met up, and eventually married.” — Johan in Minneapolis
On second thought… never mind! Sure, on Craigslist you could match up with your friend’s dad. But you could also meet the love of your life.
Like we said, the intrigue was the fun. It seems like Johan played his hand right.
Related
Andy Cohen on hooking up before he was famous: “Craigslist was Grindr before there was Grindr”
Andy Cohen also disclosed what his physical type is in a man.
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