1.
“There was a girl I used to hook up with just for sex. We were both single but didn’t have anything in common except sex. We were parked in an alley and She is riding me in the backseat of a car reverse cowgirl and another couple just laid on the hood of my car and started having sex. We stopped and the girl on the hood looked up and locked eyes with the girl I was with for a good 5 seconds. We all just stopped.”
2.
“I was in high school and I was hooking up with my then girlfriend in my car. I was dropping her off after a date and we parked a little ways down the street from her house in a more secluded area. We were going at it and this group of kids run by knocking on my windows shouting stuff, clearly they knew what was going on and were just being annoying teenagers (I probably would have done the same thing at that age).
One of the kids running by the driver-side door where we were going at it stops and presses his face against the window just to be a little shit. He immediately recoils and freezes. It’s her younger brother. We lock eyes, he continues backing away and bolts. My girlfriend saw him too and was a little rattled. We didn’t end up finishing which was completely understandable in my book.
Now I mentioned this was her younger brother and at this time I was a junior in high school and he was a freshmen and we were both on the soccer team together. Even though I could have given him plenty of shit since I sort of had the upper hand in this situation I never said anything as a cold, hard stare with a smirk was all it took for the next week or so to bring the uncomfortable image of me fucking his sister to the for front of his mind which was a satisfying enough means of payback, in my book, for cock-blocking me.”
— oaks12
3.
“Ahh, my first sexual experience… in a car, in a parking garage. Girl started giving me a blowjob… eventually got frustrated and said something along the lines of ‘it usually doesn’t take this long.’ That was an awkward way to learn that I’m not into blowjobs.”
4.
“I was in college, living in a house with 7 other guys, and we threw some big-ass parties (250 – 300 people would show). It was pretty easy to hook up with chicks because you were a rockstar in your own house.
One time, as the party was winding down, a girl shoved a piece of paper with her phone number into my hand and walked out without speaking a word. Fuck ya, I think. Text her right away and she tells me to come over (lived only a couple blocks away). I show up, we start messing around, then suddenly she says, “I don’t have sex on the first date.” Since when is this a date and why in the hell would you invite me over at 3am if not to fuck?, I think.
But whatever. I’m respectful and half-heartedly accept a handjob, but stop her midway through because frankly, handjobs are boring. I wake up the next morning, realize what the date is, wish her a Happy Valentine’s day, then peaced out and never spoke to her again.
Awkward all around.”
5.
“My ex and I were having sex in my car at the park on a late night. I looked out the side window and there he was… A clown standing a few meters away. I don’t know if he was looking directly at us or just in our general direction but that killed the mood quickly. He turned around and started walking after a few seconds.”
— Hey_IT
6.
“Met this ‘milf’ of a dating site for a one night stand. It was many years ago and my standards were pretty low at the time. She was a bit fat and not all that pretty but a shags a shag right?
Anyway i started going down on her, she stunk so bad so i started using my finger and hoping she wouldnt notice. She did and said ‘use your tongue so i tried again. I started gagging and said i couldnt do it because of my ‘asthma’
I still banged her and actually came pretty quick.”
7.
“I had post-funeral sex with one of my dead best friend’s out of town lady friends. She had flown in, didn’t know anyone, and wasn’t about to sit around bored that night. I, having a penis, and having witnessed her extremely stacked body (flat tummy AND huge tits? yes please!) was definitely down for it.
So after the reception and shit, off we went, to drown our misery in more whisky and then fuck our brains out.
To this day, my friend’s brother thinks she snuck off with another dude, and I’m not about to disabuse him of that notion. His brother (my best friend) would have high fived me for this anyway.
The awkward part came after we got back to my house and I peel her clothes off, and drunkenly leer at her (I was trying for Most Interesting Man in the World Face, but I’m sure I failed) and asked her if she had any requests or wanted it a certain way. She said she was up for anything, and I said, ‘Anything?!’ to which she vigorously nodded.
So I put it in her butt. She definitely enjoyed that but later, when she was riding me she reached back to massage my balls … ok good … then my taint … still good … then she fucking popped a thumb in my ass.
NO BUENO.
She said turnabout was fair play. I was like … ‘OK, I guess …’ but I became hyper-aware of her poop-thumb and I had to stop and ask her to go wash it.”
8.
“Getting a blowjob (best ones I’ve ever gotten were from this chick) and she deepthroats as I start to cum. She always did this, but this time, for whatever reason, I apparently came so hard it shot up her nose.”
9.
“Girl started growling and calling herself puppy.”
— jmo10
10.
“During my first time, the girl and I tried titty fucking. I was big enough, as was her boobs so it worked rather well and years of porn had me hyped that this would be great. But all in all, it was a bit lackluster and she seemed a tad disappointed I didn’t blow my load from it.
But that was later remedied from an amazing blowjob. So I learned that despite porn getting me enthused all this time, not that crazy about titty fucking.”
— Dat37tho
11.
“We both had flat chests and I didn’t have any chest hair. Every time we pressed our torsos together, it made that armpit fart noise. The weird part was that only I seemed to find it distracting.”
12.
“Sleeping with this girl for the first time, we got super into it. Like, pounding the fuck out of her. I stand up, holding her legs in the air with her upside down on her shoulders. I accidentally pull out too far and when I thrusted back in, it went straight into her poopchute.
She spent the next 10 minutes crying and holding her asshole.”
— Zwaanzy
13.
“My office FWB and I got caught by one of my co-workers having sex in the computer room. The awkward part was that the SOB was hiding behind some equipment and wacking off while watching us. I heard him and saw him out of the corner of my eye and he ran off. I confronted him. He apologized to both of us.”
14.
“I had a threeway that involved a girl whose boyfriend was out in the living room having a hissyfit the whole time. So we cucked some poor guy unintentionally. It was more distracting than expected.”
