When was the most random time you had a sexual experience when you weren’t expecting one?

Back in my high school days I gave my best friend's sister a ride home from school. We both played sports so we were always at school late. She had her own car but had gotten into a fender bender the week prior or something like that. My friend had the bright idea to volunteer me as her transportation for a few days. I was a good kid and was fairly close with their parents so I imagine they didn't anticipate anything dirty happening.

Turns out she had a big crush on me. I had no idea because I was a dumbass teenage boy, obviously. Long story short, she made a move and we ended up having a LOT of sex in my tiny '93 Nissan 240sx

Girlfriends mom was in the hospital, we showed up and her mom dropped the bomb she had cancer. Gf said she needed to take a walk, we get to a hallway and she pulled me into the men’s bathroom and pounced.

My mom and brother died on the same day when I was 17. My girlfriend lived 2 hour drive away after moving away. She came to see me the next day. There's like 30 people in the house downstairs and we are up in my "attiic" bedroom. she forced me to the floor and rode me until I came. Took like 2 minutes. I really needed it. She said it was the only thing she could think to do. Meant a lot at the time for some reason. How many "sorry for your loss" can you listen to?

The night I lost my virginity. Went to a house party at a girls hpuse. Had a good time, and was getting ready to leave when she grabbed my hand and took me to her bedroom and had her way with me. I'm 55 and still think about it lol.

New Year’s Eve 1999 (Y2K). I invited a really attractive girl I knew (but never thought I had a chance with) to a bonfire party at my friend’s house. People were talking around the fire about what was going to happen if the world ended at midnight and I could tell the gears were turning in her head.

Around 11:45pm she whispered in my ear that we should go to the bathroom. In there she told me that if the world really was about to end she wanted to have sex with me first. Gave me head in the bathroom and then we moved to my friends room. It was awesome.

A girl spilled a beer on my carpet. I got up and made a mix of detergent, and a bit of odor block (usually for sport clothes) cause beer smells awful honestly. Cleaned everything up and sat beside her after I was done. She basically leapt on me after I was done.

I can't approach women. I'm terrified of it. Approach anxiety is out of control. I was at a bar. Saw a girl I thought was cute. I couldn't approach. My friend helped me out by physically pushing me so hard in her direction that I almost fell down. Said hello. Got laid.

I went to a buddies wedding solo down in Tulum. I needed a break from the wedding activities and planned a solo scuba diving excursion. Went to scuba place and met guide and other people going on excursion. I met a woman from Australia who was coming off a nasty divorce and went to Mexico on a big family trip. We hit it off and went for a beer after. She basically put it to me and said let’s do this since I have a super early flight in morning. We did and it was amazing yet random. Looking back on it, I wish we stayed in contact since she was a really cool woman

Went to my childhood best friends family Christmas party on the 25th with my mom. Saw his cousin for the first time in years and her friend from way back. Chatted for a bit and talked about maybe hanging out later that night.

Ended up meeting at her house later that night and had a few beers. Kinda felt weird because I wanted to make a move but her friend was staying there and it was a studio apartment. Decided to call it a night and said goodbye. Got a text half way home saying "they" we're hoping I'd stay with them. Immediately told the Uber to turnaround.

My first threesome was a Christmas miracle. 😊

Back in the day, my boyfriend fucked me, up against the side of his house, while his family ate dinner inside.

His parents wouldn’t let us go up to his bedroom to “hang out,” so he said we were going for a walk instead. Burn off some energy.

It was winter and it was good.

The smirk on his face, as we walked back inside, is burned in my brain for eternity.

Edit: yes, I’ve posted this before.

Was on a first date that was going great, we were in the car heading to the next place when her Dad called. She gives me this smile puts the phone on mute and started to unzip my pants. I’m like wtf she gave me some mind blowing head. Needless to say she has some daddy issues

My doorbell rang. When I opened the door it was my ex. She was in nothing but a bathing suit. Said she was at her sisters swimming (sister lives 2 min from me) and thought she'd come in to say hi.

She tells me she's soaking wet, I offer her a towel and she says "not that kind of wet"

2 min later we're smashing.

She cleans up and leaves. Never to be heard from again. 14 years ago

Working at a coffee shop. Guy that’s waaaay out of my league asks if he can share the table to use the charger (it was the only one available). An hour later he asks me if I want to see his apartment. He was like a Greek god, you guys. I had no choice

I was at an awful, boring event with my then girlfriend and she suddenly turned to me and said “do you want to leave and go have sex?” I said yes, and we left and had sex. It was very nice. 

The best part was the shocked expression on the face of an older gentleman next to us at the event. 

Edit: actually, I guess the sex part was the best part