I got married pretty young, so I never really had a “wild phase” chasing different women. I basically went all in on one girl, who’s now my wife, and thankfully it worked out. But I’ve always been curious… what’s the most over-the-top, ridiculous, or just plain wild thing you’ve done to get laid? I feel like I missed out on some truly unhinged stories?…
What’s the most unexpected or extreme thing you’ve ever done in pursuit of sex?
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I had a great “wild phase” in my 20s. But at one point, I did quit my job, packed a suitcase, and got a one-way ticket to Japan with no job or visa in order to meet a woman lol
Went to that part of town to meet.
Drove 6 hours in January in the American Northeast during ongoing snowstorms in a car with a broken heater. I think I might’ve done some minor nerve damage to my hands, they’re way more painful in the cold than they used to be.
By the time I got there I was so sick and full of snot that she didn’t want to do anything physical anyway.
Went to a low income area and paid an obese girl $20 to grab her boobs and she jerked me off
Paid for an international flight to the other side of the continent
Meet someone online and drove across state lines when they were home alone. Oh wait, wrong sub.
Went to Canada for spring break to hook up with WoW guild mate
Not me, but a guy i know stole his brothers 69 Pontiac gto and drove from Bartlett, Illinois to Knoxville Tennessee in an effort to have sex with some lady he met online.
Met some good friends along the way.
I went to a girls house and had sex, while her husband was at work and there was a thin sheet between us and their daughter. Before the downvotes and vitriol, I was very young, very stupid, and it has ruined me for all future relationships. I have extreme paranoia and trust issues. I aways think that my wife is cheating, but luckily I never say anything to her, she can do as she pleases, I just stew about it and wait to hear the news that she’s leaving me. I have a lot of female friends but I’m also paranoid that I’ll look like I’m cheating.
I once managed to start a Convo with someone who used to post nudes on a website. I was and am still 99% sure she was not a real person / pretended to be something she was not. But still I was desperate back in those days. She said she lived not so far away from me and we agreed on a time and place. It was a park in the middle of paris. I went there and she did not show up, which was not surprising. What surprised me is that she kept answering after that and tried to set me up a second time.
One time I drove to another country so I could pay to have sex with a woman I wasn’t attracted to.
I almost walked through a plowed farm field in the pitch black of night.
At the edge of the field, I was starting to walk in but was stopped by a rattlesnake who squared up and warned me.
I lept like a cat and got the fuck up out of there.
Was on a business trip and matched with some woman on tinder. She was twice my age which was cool. Drove an hour over to the house and she asked me to go through the garage door. I thought that was weird so I left. Turns out that it was some guy pretending to be a woman and attacked and killed a man the next day. I found out on the news and I contacted the local police. Had to testify in court and he was sentenced. Scary shit.
In a desperate effort to woo the girl who I was hopelessly in love with, I bought her four new tires for her shitty little Buick Century because she was rolling around on bald-assed tires.
The next week, she drove all the way from Texas to Florida to move in with an older guy.
A year later she came back and we officially dated for awhile until she decided she wanted to be a party girl and a bar fly.
I walked in the middle of the night about 3 miles then snuck into my girls house, the only way in was through the main door so she left it open I walk in and then had to hide behind a sofa because her dad was coming. I don’t know what I was thinking.
Met a chick who was, by all estimation probably struggling with chronic mental health issues. I assumed mania of some sort but in hindsight, maybe she was a bit delayed. I’m not sure.
She was 26, I was 29. We went to her house to fuck and her mom was there, I met her mom, all good. Went downstairs, had fairly loud sex then her mom kinda awkwardly gave me cookies on the way out.
Odd fucking experience overall. Did repeat
These are separate stories:
Made sure my layover in her country was long enough to for us to meet each other for the first time.
Took a bus from one end of the island to the other, spent the night, went back (I lived in New Zealand at the time).
I didn’t really do anything extreme here to get sex, but I did hook up with a staff member at my college while I was a student. She was quitting anyway so maybe that’s a cop out. But back in college it was a pretty sweet story to tell.
breakfast lunch and dinner id wanted to see how many dates ,i knew would end in sex i could have in a day.
Ive driven across state lines for a weekend get away. honestly doesnt seem that crazy to me, because well i thought everyone was doing that since no one seemed to want anything serious anyways.
my rice purity score is 14
I got a college degree…
Got married at the age of 22 having only known her for three months. It’s worked out fantastically for the last 25 years, but it was still ‘crazy’ considering how badly it could have gone.
Drove six hours to play “just the tip” with a girl at a Christian college. Ill never do that again lol
Booked a hotel room for a potential ghost. We met on reddit and chatted a bit. We decided it would be cool to meet in person, I was traveling anyway and jokingly said we could meet there. She agreed, I showed up to the hotel and it was a real person, just like I had been chatting with. 1200 miles, of the most anxious flight I had ever been on.
I lost 85 pounds.
Tried taking a girl on a date: we met at a subway station and I had parked my car in a gated lot nearby. I did not realize that the parking lot was about to close. By the time I had taken her to my car it was locked down. There were however some not-too-sturdy hedges and rose bushes on the side of the parking lot. I drove my car straight through them and proceeded with the date as planned.
End result: some paint damage, I lost my virginity to her, we became a couple, and a year later she cheated on me. Let’s call it a learning experience.
My boss is a plumber and told me a story about when he was recently divorced in the early 2000’s he flew to New Jersey in January to meet up with a rich summer customer for a weekend fling. On the way there he was stranded in a snowstorm layover in Chicago and met an interesting flight attendant who brought him home with her.
Brought him back to the airport the next day after some hanky panky and sent him on his way to meet up with the woman he originally went to visit.
I drove 2 hours because of traffic . Only to be disappointed. She lived with her mom . 😆
Paid a hooker. But i was on so many drugs i couldn’t get it up.
My girlfriend was a virgin and a year younger. When I was a senior and she turned 17 she decided she was ready. We had no place to go so we parked in a cemetery and got in the back of my mom’s Buick park avenue with light blue tufted seats. We left a bloody spot about the size of a dinner plate that never came completely out.
I don’t even necessarily think it was me trying to get laid but I joined a Christian group in college just so I could make friends who didn’t want to drink all the time. There were a ton of single women in the group and ended up dating one. It was a fun time but didn’t work out in the end. Stopped going as soon as we broke up as it was way too awkward. Made a ton of good memories though so worth it in the end.
One guy I had a huge crush on used to used to walk three miles to my house at night, climb into my window and smoke me out, just for some mediocre head. 😅 Several times.
Ive flown to other country, only finding most wont go past 5 miles.
Became a vegetarian. Waited 6 months. Got her in bed, ate a steak when she left and broke things off. I was in my 20’s.
I flew to another continent to meet a woman….twice.
Solicited the services of a prostitute
Got a loan to go to Beirut from San Diego. Only got a hug
I was straight laced, single, and focused on career/finances in my 20s. Looking for inspiration in this thread for letting my hair down in my 30s (though idiom falls flat since I’m bald 😅)
Went skiing with a chick I was interested in neglecting the fact that I (a) had never skied before and (b) thought the appropriate gear too take to the snow fields was jeans, t-shirts, a couple of jumpers a pair of old boots and a shitty old sleeping bag.
I have never been so bored, so wet and so cold in all my life.
And that early going home bus ride home was a nightmare.
Edit: Oh and I found out she was on her period the whole time we were there and being a student, I ran out of money after the first night of drinking.
I’m desperately afraid of blood. Had previously dated a girl and it didn’t really work out. Reconnected a couple years later and realized we couldn’t be a couple due to major life goals that competed, but we still were attracted to each other. We had a whole thing planned out where I would take her virginity and then she had to give me the news (knowing that become faint having my blood drawn) that her period had started on the day of.
We decided to do it in the pitch black in the back of my car. No blood seen. Had sex. Did it again a couple times sans blood.