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15 People Share Their Craziest Hookup Site Stories

15 People Share Their Craziest Hookup Site Stories

by Ayoub Mask

People usually get their expectations way too high when they start using hook up sites,  which is really not the ideal thing to do considering the general reputation these websites tend to have. It's a really huge gamble that people are willing to take, completely ignoring all the red flags that they stumble upon along the way. At the end, life is all about taking risks, but that doesn't mean you shouldn't take all the necessary precautions that will help you avoid a world of trouble, like perhaps getting murdered in cold blood and instead you'll just end up with some crazy stories you'll never be able to forget.

Found on AskReddit. via ThoughtCatalog


1. We use Craigslist to plan threesomes 

“Am a bi male (that’s simplified but will do) in a hetero relationship with a straight girl for the last 3 years. Mostly on vacations, but sometimes locally we will use Craigslist to find a guy for a three-way.

I’d honestly say we are average looking, but usually get dozens to hundreds of responses, (80% or more are immediately discarded). We’ve had 2 what I would call successful one-night events, a couple of kinda awkward encounters, and one ongoing FWB that got a little weird at the end.

Cheaters do abound, and we won’t help someone cheat, that we know of. It’s actually kind of interesting how many people are upfront about it.

Occasionally we have posted an ad and just go “well, haven’t gotten anything in a hundred responses that sounds good” so we just go on our way and take it down.

We do get some of the kinda creepy “well, I’m not bi or gay, but I guess I can do guy on guy stuff so I can play with the girl.” That to me is pretty sad and desperate and not what we want.

So, long story short, usually works out, some hiccups, some meets that have started in public and end up with no connection, some last minute cancellations, but never had a 

2. We went to the zoo

“So…Tinder? Yes, it turned into one of the best night/days of my life. I was new to the country and didn’t really know my way around anywhere. I was bored at the hotel and I had just got my new phone SIM. Decided to try out Tinder as it was in the top 5? apps at the time. Met up with a girl and a group of her friends a few hours later and they took me around the clubs in town. Night ended in sex and in the morning everyone made pancakes and they took me to the zoo. I thought it was time to leave after the zoo but they invited me to play beach ball midday.

TL;DR New to town, used tinder, had sex, received pancakes, went to the zoo, played beach ball, still friends.”

3. Free BJ booth 

“I used Craigslist, and found a private glory hole in someone’s house. I went there like 10 times and she/he was amazing.

It was most likely a dude but I am pansexual so it doesn’t bother me one way or the other. Not knowing is what makes it exciting though. I’d like to pretend they were a MtF trans. That’s the dream.

For those who want to know how it went down, I found the post on Craigslist, so I sent them a message. They had a plywood slab set up in a doorway. It had a hole in it that was covered with duct tape so you wouldn’t get a splinter. It was set up between their laundry room and kitchen I think. They would tell me what time I could come over, and they left the door to their laundry room unlocked. I would come in, stick my dick in the hole, and enjoy.”

4. It was fun and the sex was okay

“I did, in 2002, right after I separated from my husband. A friend told me to check out Lavalife. I was in my late 20s and after being with the same guy since before I could legally drink, I felt that I was owed some one-night stands.

Met one guy and made out in a Burger King parking lot. That one went nowhere.

Met one guy who spent the night twice, so I guess he was a two-night stand. After the second night, he dropped off the planet. No way to know for certain, but I think that guy might have been married.

One guy was great in bed (and the shower, and the couch), but was not a dude I could have a conversation with. Had a massive schlong, too. Like, it was fun for a night but only a good idea when I was really drunk.

One guy was interesting, but had the tiniest dick ever.

And that was it. Shortly after Tiny Dick Dude, I met the guy who I later married. And thus ended my experience with Internet hook ups.

Tl;dr: wasn’t killed, wasn’t raped, had okay sex, don’t regret anything with the possible of the exception of the tiny dick dude.”

5. It was a huge waste of time

“I tried them out. I won’t even use OKC anymore (guy). Hitting up seedy bars in bad neighborhoods feels way less filthy to me.

Every woman I’ve met online has never mentioned protection. NEVER. It makes me cringe when I think about the sheer amount of herpes on Tinder alone. I’ve had one ‘date’ rip my condom off immediately after telling me she’s not on the pill.

Even with a condom, it still feels like Russian roulette, because everyone using these sites seems to think nothing of regularly fucking strangers bareback….And unless everyone’s using condoms, you may get the joy experiencing another man’s cream pie/unholy milkshake all over your junk.

Overall, it’s been a waste of time. Lots of mediocre sex. Some sex so bad I wish I could unhave it.”

6. It helped me grow as a person

“I signed up for PlentyOfFish after I broke up with my last boyfriend and had lost a ton of weight. I was originally trying to actually meet guys to date, but it ended up turning into just a bunch of hook-ups. I met a lot of guys and had a lot of one-night stands. I also ended up with a few FWBs.

Honestly, I went wild. I don’t regret it at all because I got to have sexual experiences that I would never get to have now with my husband. It helped me improve myself in terms of sex and pleasing men, as well as myself. I also feel it helped me grow as a person. I grew too attached to some of these guys and had my heart broken a few times. I came out all right in the end, though.

Some of the guys I used to hook up with do contact me out of the blue, but I’m married and about to have a kid, so it’s really weird. I just make polite conversation and then never speak to them again lol.”

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7. Craigslist gangbang

“Met a couple on Craigslist where the husband was wanting people to gangbang his wife. I’ve never done anything anywhere close to that before, and while I have talked to the couple a few more times, the timing hasn’t worked out for me to do it again. The chick was decently hot, probably late 30’s or so and a personal trainer with an amazing body. Both she and her husband were very nonchalant about the whole thing and it was one of the most energizing experiences of my life. We text back and forth occasionally and I hope to one day get that opportunity again. 10/10 would recommend.”

8. My first time was on Craglist 

“Last summer I had just reached a point where I was in the best shape of my life, really had been working on my looks and appearance and I was about as tired as you can get about still being a virgin. I’d put some posts up on Craigslist a few times in the past but they weren’t very serious and didn’t have much on them so there’s no real surprise that I didn’t get any responses.

This time I was very straightforward on what I was looking for, had a good picture of myself and made it a point to refresh my ad every 3 days. After a couple refreshes I got a got a reply from a woman who basically said I was a fake and demanded we swap proof pictures. (She had a huge thing for redheads.) She was a very fit, mid-thirties but still had a really cute geeky kind of look to her. We met for coffee about a week after she messaged me and spent an hour talking about Game of Thrones and The Walking Dead since I’d mentioned it in my post on Craigslist (Put a favorite show in your subject line). If I was reading this I’d probably be like, “yeah that happened.” I got extremely lucky.

One thing I remember vividly was how there was this stuck up, snobby looking woman sitting with her husband in the cafe at the table next to us the entire time we were talking. The tables were situated so the woman I met had her back to the snobby old woman’s back, I thought for a second the snobby lady’s neck was literally going to snap the way she spun around to look at us when we finally talked for a little bit about sex and what our expectations were from each other.

I met up with her another week later at her place and the rest is history, people talk about how awkward their first time was but honestly it felt very natural and relaxed for me, no nerves at all. Her attitude towards sex and the whole situation made it really easy to just enjoy myself and focus on the experience. I’m not saying I was amazing in bed but she liked me enough to bring me back almost every weekend for the rest of the summer so I learned a lot, turns out I got a skill for giving head and that probably helped with the repeat invites. As far as first times go I honestly don’t think I could have asked for a better time or person to experience that with and I’m really grateful to her, we still text each other occasionally about Game of Thrones and The Walking Dead.”

9. I contracted chlamydia...

“I was in my early 20s and had just had a kid. The mother and I lived together but were not dating and had separate bedrooms. I found it impossible to date under those circumstances, so I followed one of those links and ended up on sexsearch.com. I believe I paid $30 for a month.

I can’t remember how many random people I talked to. Mostly they didn’t reply, because I didn’t want to use my picture on the website. When I found the woman I went to prom with on the website, it reaffirmed my caution. (I didn’t message her.)

Anyway, I finally found someone who had pictures that I couldn’t believe were possibly real. She was REALLY, REALLY good-looking, thin, great smile. We started a conversation, and though there wasn’t much substance, we moved toward the inevitable ‘we gon’ fuck’ moment while I looked for any signs that it was a bot. I think I decided I believed she was a person when she reminded me she owns a gun as we were meeting up.

So we agreed to meet at a park in the middle of the night. Now, I very easily could’ve been murdered, and I was aware of that at the time, but I hadn’t had sex in like a year so at that point I was basically ready to die. But seriously, never underestimate how fucking stupid someone is willing to be when they want to have sex. Anyway, I drove and parked and met her on the sidewalk, and what the fuck dude she was as hot as her pictures. Just fucking gorgeous.

We went into the park and laid down a blanket she had brought and, yeah, we had sex. And she told me to tell her I loved her, so I did, and that was my first inclination that something might be kinda fucked up here.

We finished and left just as it was getting light in the morning, with each other’s phone numbers, and she called me a few weeks later and asked me to come over to her house. It was at this point that I learned she had three kids of her own (though I could kinda tell from stretch marks), and through talking to her, I learned that she worked at a phone sex hotline. She apparently would leave work super horny a lot of the time, including the night she met up with me. What I didn’t learn at that time was that she still had a boyfriend and that he lived with her.

So I come over to her house, and the kids are gone, and we have sex. And this becomes something of a regular thing, and I should fucking know better because she keeps peeking out windows and telling me to leave quickly, but it’s good sex other than her insisting that I tell her I love her the entire time, which, yeah, it’s hard to have sex with someone on the regular without developing feelings, so I didn’t feel so bad about it after a while. Have I mentioned I’m a scumbag?

So, one time we’re having sex, and I hear the door starting to be unlocked. I’m like, ‘Who’s that?’ And she panics and says, ‘My boyfriend.’ And I’m like ‘What?’ The door opens and this beefy Asian dude comes in and says, ‘Are you [my name]?’ Dude straight up knew my name. I said ‘Yes.’ She’s stammering that we’re just hanging out and nothing’s happening. (We had our clothes back on by the time he came in and were sitting on opposite sides of the room.) This dude proceeds to walk up and start punching me in the head.

Here’s the weirdest thing. I’m not sure if he sucked at punching or if it was adrenaline, but I didn’t feel a damn thing. He was just bouncing my head around with his fists and I was sitting there with my arms up in a feeble defense and he was just going at it. I made literally no attempt to fight back because, on some level, I was aware that I was fucking this dude’s girlfriend and this was, y’know, a pretty appropriate reaction on his part. Eventually he stops punching, I think because I’m just standing there, not reacting at all to his punches, and he’s hyperventilating with the meanest look on his face I’ve ever seen. I say, ‘Okay, I’m gonna go.’

I walk out the front door, she leans out after me and says, ‘I’m sorry, we can’t be friends anymore’ and closes the door.

I believe it’s like two years before she called me again, to tell me that she was depressed and lonely and wanted to meet up, and it somehow came out that the dude who had punched me, the father of her children, had been killed in a hit and run and that she was now a stripper. So, we did it one last time for old time’s sake. She dropped a bag of crack on the floor of my living room and then asked if I wanted it. I was like ‘No thanks,’ and that was when I decided definitively not to hook up with her anymore.

Also, she gave me chlamydia.”

10. A pretty good three-way 

“My girlfriend at the time and I signed up for an AdultFriendFinder account to look for someone to have a three-way with (MFM, no guy-on-guy). We weren’t just going for sexual attraction, though, but also looking for someone that we wouldn’t mind hanging out with someone around our own age. We couldn’t find anyone that fit our bill 100% (and anybody whose first contact with us was a dick pic was automatically out, since we had a line in our profile clearly stating we didn’t want to see dick pics), but we did find a guy who was about 10 years older who was chill and not pushy. We ended up meeting up in public, then went back to his place, hung out for a bit, then spit-roasted the fuck out of her.

It was pretty good. We all used protection, nothing went wrong. It was a lot of work just to find someone we actually felt comfortable with, though.”

11. Crazy weekly gangbangs 

“I (male) was on Fetlife, and I answered a request seeking guys for a gangbang. I got in contact with the host, he sent a picture of the girl who was super hot, then he sent me a time and an address (at a hotel). I showed up along with six other guys and we collectively banged the shit out of this hot blonde. It was actually incredible, like living out porn. She had a guy with her so she wasn’t just by herself. Everyone wore condoms and was very safe and respectful. And everyone was so friendly!

After this initial gangbang I got put on ‘The List.’ The GB organizer would send out emails when he had girls interested, with details about time, place, pictures, and what was on/off limits. Over the next six months I went to about 10 gangbangs before getting over the whole thing. That was only a fraction of the women who were actually interested in GBs, sometimes I’d get three emails a week, apparently lots of women have this fantasy. Organization is the most difficult part, you have to organize the schedules of 10 people and get a hotel reserved in a central location.”
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12. The results were different depending on the platform 

“I don’t know what you exotic stories you expect, but it’s actually what anyone would expect it to be for gay guys. I’ve used Craigslist and Gaydar, both years ago, and it’s worked in two ways. On Craigslist I once offered an extra concert ticket and found a guy who was to become a years-long friend. On Gaydar, I found someone to show me around a new city, we hit it off but not sexually—another friend. But I also met several guys who almost literally did not want to talk at all, just fuck. Exchanging names was too much for them. I found it tiresome after just a few times.

Then there’s Grindr. I haven’t personally used Grindr more than a few hours to see if there’d be interest, as I was/am in a committed relationship, but I’ve seen people have lots and lots of fun—just chatting/flirting, exchanging pics, hanging out and going dancing with friends, or just meeting up to fuck (or do other sexual activity). Grindr users seem more OK with themselves (at least the ones with faces in their pics) and not embarrassed or ashamed or rushed like Craigslist users were. So they’re more willing to become friends with benefits, with the amount of ‘friend’ and the amount of ‘benefit’ much more flexible. I would use it if I found myself single again.

Straight people may have drastically different results.”

13. It's a miracle that I didn't contract an STD

“I (female) used OKCupid to hook up with about 30 guys in a two month period, some of them multiple times but mostly not.

I ended up ditching the site for a short-lived, unfortunate relationship with one of the guys and went back after my next, current, wonderful relationship became open and turned my account back off about a week later when I realized why I was glad I’d left the site:

It’s made to be an addiction. You get all the sex and/or human connection you want, but these sites are based on a quantity model. As in to have any hope of finding quality, unless you beat the odds, you have to play by quantity. You have to go on as many dates as possible to have one really, truly good one.

Not that most of the dates were bad. Just that you have so many mediocre or fine or pretty all right dates that you start to forget what a good one feels like.

Now I’m a classy slut so I almost always vetted these guys with food or coffee before taking them back to my place, so I got really good at small talk. By the end of two months I started loathing all of them. I remember sitting in a cafe, staring at the steam from my coffee cup, listening to a guy I liked well enough (we both liked books by the Lost Generation and bad horror movies) talk about his relationship with his mom, which I had started by bringing up my mom, and I realized how fucking bored I was. I didn’t give a shit about his mom or anybody else’s. I caught myself actively waiting for him to stop talking so that it would be my turn again, because this was the third guy this week I’d heard talk about his mom and he just cared so much more than I ever could. And I said to myself, ‘this isn’t me; I can’t be this shitty to people.’

I got over 1000 profile views a day on OK Cupid. I got on average messages from 30 different guys a day. Even winnowing out the ‘hey bb wunt sum fuck’ messages that left me with at least 5-10 prospects a day, and I wasn’t being all that picky at first. Then I started being picky, but only about looks, because I realized after 20 or so first dates that I had no way to figure out how our personalities would really mesh until I met him in person, so I decided, screw it, I’ll just try to cut down on the overwhelming number of meaningless, shallow interactions by only having them with the exceptionally hot guys. I hated myself for that, too.

The crazy thing is, I went into this thinking I was going to learn a lot about having sex. All I really learned was how to have bad sex, or pretty okay sex. I never had truly amazing sex during these hook-ups. It was, above all, mediocre. These guys would all kiss poorly, likely sloppily, and there was lots of lead-up to the sex, but I wouldn’t call it foreplay; rather, it was an extended make-out session where we tested how far the other person was willing to go, and once we were both naked it was ‘okay time for the main event: penis in vagina!’ I gave a little head here and there when requested or I felt like it but I never received head (I asked a few times and they’d give a few half-hearted licks before saying ‘I can’t wait’ and going to the p-I-v). Then, I swear to God, every one of these guys became a literal jackhammer. They went for, above all, SPEED. They fucked me as fast as they fucking could. Not as hard as they could, not as well as they could; fast. I had to stop myself from laughing at it so often. I felt like a masturbation tool. One that was worshipped like a goddess and treated like a human being, just… They all had sex like they were masturbating into me. Because they didn’t know a thing about how to have good sex from anybody’s perspective but their own.

And don’t get me wrong. Most sex with most people is bad the first time. You just don’t know how the other person works. So a word to the wise guys out there: The first time you fuck a girl, do everything as slowly as you can. Get to the sex slower. Rub her clit first, very softly and slowly. Eat her out a little. Kiss all the way down her body. When you get to the p-I-v, don’t be a jackhammer. Like Tenacious D says, fuck her gently. Move slowly, every movement of every muscle made with intention. It will be amazing, for you and for her. She will call you back. You’re not going to be able to be a porn star that first night. But you can be sensual, and fucking great.

I met all kinds of guys. Guys who were in the game the same way I was and just wanted a few rounds of Smash Bros before bouncing their balls off my clit while they doggie-styled me. Guys who stuck to missionary with a passion and were heartbroken—literally—when I wouldn’t return their calls after a one-night stand that was a walk in the park with a joint, a movie in bed and some sex—the first day we met. Guys everywhere in between. But in the end there were so many guys that they all just felt kind of the same. I liked a lot of them a lot and would have probably dated them a while in more classical circumstances but there just wasn’t any real spark. And I was glad I had gotten the sex out of the way so quickly. Once that question was answered it was easier to see them for who they were instead of who I wanted them to be, the personality-judgment-equivalent of fucking them with the lights off so their body looks however I want it to look.

Would I go back in time and do it all again? Hell yeah. Would I do it again now? No fucking way.

My final lesson: WEAR A FUCKING CONDOM. FUCKING DO IT. I got tested for STD’s after all of this and somehow miraculously caught none and that’s a miracle because I never used a condom because I’m on the pill and he never brought it up. And I always thought I was the kind of person who would be like, ‘duh, of course I’d always use a condom! STD’s are scary!’ AND THEN I NEVER DID AND THAT FUCKING TERRIFIES ME. And none of them did either. Even though they were all very smart guys. Most of them didn’t even ask if I was on birth control. GUYS. WE HAVE TO BE SMARTER ABOUT THIS, OKAY?”


14. I foud my husband through them

“I used to be on ALL the gay hook-up sites I could find when I was single. Usually had a great time hanging out drinking and whatnot, then of course the sexy time after.

It didn’t always end in sex, a few of the guys I met I actually made great friends with, some of my best friends still to this day.

One guy specifically I connected really well with. He fit right into my social circle and quickly became one of the BEST FWB a guy could ask for. Neither of us was looking to date or anything serious, but we just couldn’t help ourselves.

At one point we realized we were getting attached he even told me ‘we’re gonna have to stop having sex, I think I’m falling in love with you!’ Well, I had been falling for him for some time at this point and once I realized he was falling for me I wasn’t going to let it go.

A few months later he moved in, a few months after that I purposed, a few months after our 1-year anniversary we got married. He’s my best friend, my lover, and partner in crime. When we argue (which is rare) it’s only about something one of us said the other took the wrong way, and it’s always worked out before bedtime.

I never thought I’d find anything but sex as I’d been hanging on those sites and then using the apps every time I was single over the course of 16 years or so. Hey, who knew? I’m just glad I hung in there. Neither of us have ever been so happy with every aspect of our life’s due to the support we provide each other and the love we share.”

15. I used Craigslist to find older women

“33yo male, I’m into older women, like middle aged or more, always have been (sorta). I’ve found and met up with 4 over the years, all from Craigslist, 3 resulted in sex with 1 becoming a relationship.

The first was 59 (I think), I was 28. We initially met for breakfast, then went back to her place for sex. This led to weekly meetings that lasted 3 or 4 months before she decided to completely stop talking to me. I think I got too close, but she also had her own issues. She had similarly cut off several people in her life including her sister and her parents who both died before she ever spoke to them again. The sex was all right and I learned a lot about women. I was only into men up until that point but had always been curious about women, specifically older women, and she was my first. We didn’t use protection as there was no chance of pregnancy, which was not smart, but I don’t regret my time with her, only the way it ended.

After a yearlong dry spell I met another woman at 29, she was 64 very fit and had implants (they were rock hard). She was crazy but not cut-your-dick-off crazy. She had this need for cock, she almost exclusively would come by to blow me which consisted of her almost desperately gorging herself on my cock trying (successfully usually) to get me to cum three or four times in a row. I ate her out a few times and we had maybe eight or nine thrusts worth of vaginal sex but for her it was pretty much all about fellatio and her doing things to me. She had all kinds of toys, mostly vibrators she liked to tuck here and there while she blew me. She would also often ask if there were any weird things I’d like to do to her. She’d often suggest things like putting a speculum inside her to spread her open, and using other toys on her. She moved several states away after a couple months and before things could get too freaky.

The third one a few months later was an erratic late 50s woman whose life revolved completely around her dog, it was one of those service dogs that soothe the elderly and the terminally ill. She had some kinda semi regular spot on the local news with her and her dog. Anyway we never had more than a couple dates and it was pretty clear to me that any other human in her life would have to compete with that dog and that likely had to do with why she was single. She was also the daughter of a fairly famous singer from the 60s. She lived with her and I got to meet her, her bathroom was full of old pics of her mom with like Sammy Davis Jr. and other celebs of the time. Hallway had gold records and whatnot, pretty surreal. Her mom who I shall not name, once told me ‘good luck’ with regards to our dates. Ha.

Last one was later that same year after I turned 30. She’s 29 years my senior and we’ve been in a loving relationship for almost 4 years. I intend to be with her until she leaves this earth. I’m an atheist and have always been a huge skeptic, but I felt almost right away like we had known each other for centuries and that feeling was mutual. Life is a crazy fuckin’ ride, and the rules of society are not set in stone. Do what’s right for you.”



16. I had plenty of options 

“Met 3 guys (that I fucked) and I think 4 girls? I’m a lesbian, wanted to see if I liked guys, so I got with 3 guys from these apps. First guy I got lucky, he was so great at sex. I was like I might actually be bi, I kept seeing this guy for a month until I hurt his dick on accident while riding him. Gave another guy a try and it was so awful he was being so pushy until I was like fine, clearly he wasn’t used to getting some cause he didn’t know where my clit was and he came within like 5 mins, couldn’t get me very wet. Third guy I actually liked, foreplay was great and he made me cum, then when we ‘fucked’ he lasted like 3 mins. Even he was shocked and I was like uh, it’s all right. Didn’t feel like fucking again and I’m sure that I’m gay from those experiences.

From the girls I met, those are interesting. Two of the girls I got with were clearly straight girls that were experimenting. They told me they were bi and when I got with them they also could not find my clit, and didn’t do anything that felt good. So now I’m weary of getting with a straight girl, and if I do, I need to know that she masturbates with her hands, otherwise when she’s trying to get me off she won’t even know what feels good. So another girl was just a hookup, but I liked her, never talked to her again though ’cause I got with her on vacation. Last one, well, actually the first person I fucked from Tinder was actually my first time with a girl, took things slow like one would with dating, things were going so well with this one, I liked her a lot and was feeling optimistic, started catching feelings. But later she told me it wasn’t fair how she’d been treating me, and that she had a girlfriend, and she was cheating with me. This kind of pushed me off the deep end, I went a little crazy temporarily, I started smoking more weed than ever, and got fucked up 3 days straight on Nyquil…clearly my reasoning wasn’t great in this time so I said a lot of shit I shouldn’t have and she basically thought I was insane and told me that. So yeah, basically average experiences. I’m addicted to the weirdness of meeting people off apps.”

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