In this article, we asked some of our readers to share stories of the wildest things that they have done in their lives. Enjoy reading!
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I once had sex with a stranger. I was at a bar, there was dancing, there was alcohol, and after a few too many beers, I saw this freakishly tall guy.
Even in heels, I only barely reached up to his chest. I don’t know why, but for some reason I really wanted to know how it was to have sex with someone that tall.
It was not good.
I was very, very drunk by the time we got to his place, and as we were going at it, I could only think that it was the worst sex I’d ever had.
So I did the only thing I could think of – I told him. He wasn’t really sure what to do at that point, but at least he stopped.
As I ran out of his apartment with my clothes in my hand, I realized that I had no idea how to get out of his building complex.
I ended up having to climb a fence to get out. It taught me a valuable life lesson about hooking up with strangers – you can always be honest and leave if it’s bad.
I’m hardly famous. I’m in the USA, I travel a bit, so state didn’t really matter.
I went to bars mostly to socialize, I’d talk to women, men didn’t matter to me, I went to have fun and make people have fun. I never really bought anyone drinks, nor did I ever ask for sex.
I asked my girlfriend that started as having sex with a stranger why she did, which she said she’s never had sex with a stranger before and it’s out of character for her.
She said it was a combination of my charm, humor, looks and talent.
My talent she was referring to was that I used to bring my guitar and sing to outside bar patios as long as the bar said it was okay.
I mostly did improv, singing whatever in the moment. If a woman came over and flirted I’d improv a song about her to flirt back.
My girlfriend found me too intimidating to approach when I was singing possibly due to the fact I hold eye contact with people until they look away, I’m not sure.
Other times I would not have my guitar, I’d just talk with whoever approached me about whatever they wanted to talk about.
Nights with strangers usually wound up talking for a bit, then they would either bluntly or shyly asked if I wanted to walk them home or share a cab, I’d say yes always. I’m the kind of guy that takes free candy from strangers.
The walks usually ended with me getting invited in, I rarely declined.
The cab rides would usually end with me saying I can get dropped off first if you want and they would ask to stay over.
We’d end up having drunk sex, wake up in each other’s arms and have the most awkward mornings at times.
Having to ask for each others names after hours of sex and passing out together was quite awkward and never really became normal. Even if I got used to it their awkwardness took over it ever becoming normal.
Most of the time after properly introducing ourselves they would say something similar to again some time, we’d exchange numbers, I’d head home or offer to drive them home after breakfast and hanging out. I’d meet the same used to be stranger and we’d be FWB for awhile.
I wasn’t really into relationships at the time so they would move on as would I.
A lot of them through over the years are still really good friends, we regularly chat and hang out, though now that I am currently seeing someone we’ve all dropped the benefits part.
I was in this club and the night was coming to an end.
I had observed this relatively good looking girl dancing all night, when everyone was about to leave I approached her and asked if she wanted to come home with me. T
o my surprise she said yes, and there I was 20 min later in bed with her.
She was the freakiest girl I have ever been with. I even tried anal for the first time and my dick hurt for about a week.
Never knew her name or where she came from until I saw her a year later at a dinner party with her fiance.
We both didn’t recognize each other at first, and when we did, needless to say it was the most AWKWARD moment ever.
My best friend in high school would date a new guy every few weeks.
She would always want to hang out with me, but also her new guy, so she would invite me over, and when I got there, surprise!
Her guy would be there, with a ‘friend’ for me.
After half an hour of awkward conversation, she would disappear with her guy into the bedroom and the remaining guy and I would avoid eye contact as the sounds of passionate coitus filled the house.
I slept with a few of them just to break the awkwardness.
I once made out with my Uber driver.
That particular day I had to get to a place to have my mobile phone repaired. I got a decent looking but fun filled lady as my Uber driver and there was an instant connect between us.
We chatted on wide range of topics. It was half an hour ride, and when I alighted, I wanted to ask her for her number but did not have guts to . Left it as it is and just said bye, turned back couple of times just to say bye.
And again when I booked cab for my return I got the same person. One thing lead to another then I started touching her thighs .
I slid my hands into her jeans and felt her ass. This continued for few more mins and on a calm street we parked the car and we started to kiss. Then we left for my home and had the hell of a session.
Besides the hundreds of strangers I slept with in sex work, yeah I have, many times!
One night stands are half the fun of being single.
I can go out, see someone I like, pull them and fuck them.
I then get to leave afterwards, everyone wins.
I met a guy in a gay club once. He kept looking at me, I looked back. I told him I wanted him to fuck me, then fuck off. So he did. It did nothing for me as I am gay, but I thought I would anyway, just for the hell of it.
I’ve had sex with countless girls in gay club toilets. I once had a one night stand with a straight girl that I pulled by sharing cigarette smoke with her by inhaling it into my lungs, then putting my lips to hers and blowing it into her lungs.. She took me home that night.
Stranger sex is my favourite type of sex, outside of a relationship.
I would rather that, than a regular fuck buddy as it keeps it different every time.
I’ve had a few one-night stands in my day, but for this response, I’ll stick to one.
I was hanging out with a new friend, drinking around my neighborhood, and he was relatively new to the city, so I recommended places he should patronize.
Sure enough, as it was nearing 1:30AM, one of of the places was an afterhours nightclub that didn’t serve booze but played house music till 4AM. I let him know it was hit-or-miss; sometimes the DJs were exceptional, other times it was a bit amateur blah-blah, blah – he wanted to go.
We got there, paid the cover, and witnessed numerous kids hopped up on molly or coke. Some others were drunk, and then there were the sober dwellers.
They stick out. I’ve been to this club and it certainly can enhance the experience but tonight we were only moderately drunk.
Anyhow, we both got to dancing, the music was decent, but the real hope was to hook up with some girls. At least that was my assumption for him. For myself, I was indifferent.
We danced with a couple of club girls playing the ol’ “desire me but don’t act desperate it’s a turnoff” game…but he kept striking out.
Maybe our pupils were too small for their tastes. After an hour or so, he decided to skate.
After he left, I stuck around to see if the music picked up and see if this girl who kept making eyes at me was interested or not. While posted against the bar, a voice snuck up from below,
“Are you a gigolo?”
Right in my chest area was a cute little woman with a sweaty sheen on her forehead. Now I’m 6′4″, and I had to turn my head all the way down, so she must’ve been 5′2″.
I grinned and told her no, if I was a gigolo, I’d be a terrible one as gigolos need to make money and judging from this crowd – there was, at best, some drugs and tightly rolled bills. Not enough to pay the alimony.
She heard none of it but was fixated on me.
I was still making eyes with the voluptuous brunette across the bar, who now seemed a bit perturbed at my new acquaintance.
An acquaintance that was now groping me. Without any permission and with little attention.
She grabbed at my waist, tried to throw her hands around my neck, touched my chest, and talked as close to my face as possible, the kiss close proximity… but I was coy. Standoffish. I had eyes for the brunette.
“So you just stand there with that ‘I have a big dick’ pose?”
When I first moved here, here being San Francisco, statements like these used to rouse me. They don’t any longer (and I don’t have a big dick, above average but nothing spectacular) so I kept my cool with a smile. Shortly after, I saw the brunette leave.
She gave me a half scowl-half smile. I took it in stride then turned my attention to this persistent woman hovering beneath.
The change in attention was enough for her to ask me where I lived. I said close-by and she probed my personality with more strange statements like “do you just come here to pick up women?” (fair) “are you sure you’re not a gigolo” (yes), and the one that would be oft repeated throughout the night: “I’m not desperate but…”
After a short chat, we were headed to my place. I’m a writer, so in circumstances like these, my writerly curiosity gets the best of me (even if I’m not turned on).
And, at this point, I was more curiously assessing this woman who was headed to the house of a total stranger, who was 6′4″, long-haired and bearded — What type of issues does this young woman have?
During the walk she asked,
“Are you a serial killer? You’re not gonna kill me are you?”
I smirked and said she’s free to leave whenever she wants, this isn’t going to turn into an episode of Dexter. I watched her personality shift quite a bit.
From flirty, to offensive (now repeatedly asking if I was gay), to self-righteously comedic (jokes she thought were funny).
Again, less than an hour ago I met this woman, and now she was headed to my place. We had also kissed a bit and she asked how strong I was. While waiting for my response, she wrapped her arms around my neck.
So I picked her up and pinned her against a nearby wall and we made out. My hands firmly grasping her ass. Her legs, tightly wrapped around my waist.
Yet, I was still strangely detached. She, on the other hand, was moaning loudly.
I found all this much more comedic than erotic…especially hearing passersby quickly shuffle past.
When we got back to my room, she complained it smelled like coconut oil. It did. I use that shit all the time.
Then she repeatedly said we were not going to have sex, “…I’m not desperate for sex.” “We’re not going to have sex, I’m not desperate.” I complied, as I was again more interested in what kind of crazy this complete stranger had in her, less inspired for a good fuck. (i.e. Blood was flowing up, not down)
Soon enough, she was naked.
My hands rubbing in between her thighs, my fingers on her clitoris. She began making exhibitionist type moans and groans.
She kept banging her arms against my bedroom wall. So much so that I asked if she could be a little quieter because I have roommates.
She didn’t like that and made a little girl type shrug, pretending she didn’t want any more “intimacy” (again, she wasn’t that desperate). I’ve been with enough women to know this ploy. So I just laid down next to her and told her “goodnight”.
Five minutes later she asked why I wasn’t naked. I teased that I thought she didn’t want to have sex and she responded that she just wanted a naked body next to her. Soon enough, we were back at it.
This time she was fervidly undoing my belt. I chortled to myself, as I knew she’d be disappointed when she finally saw my dick because it wasn’t erect.
And sure enough I watched the disappointment register across her face as my flaccid penis was revealed.
She quickly inserted that she wasn’t to blame for the “dangling meat”. So I rolled beside her and pretended to sleep.
Moments later, her naked butt was rubbing against my groin and her hand was reaching for it.
At this point, I realized she wasn’t particularly good in bed, as she grabbed at my penis and moved it like she were rattling a pom-pom.
I laughed again and then grabbed both her hands, placing them behind her head and got to work…
To round off this story, she came, I did not.
We didn’t have sex, no condoms, but she rubbed her vagina on my erect dick (yes, it finally woke up) until my urethra hurt mid-pee the next day (not burned).
I learned she was 34, which shocked me because she looked mid-20s, and had a 7-year old daughter.
After she came, she asked me to come by her place the next day to meet her daughter for their “Sunday Garage Sale”, skeptically, I asked
“Do you think that’s a good idea…?”
We never saw each other again.