1

Win:

“Probably my first real experience with roleplay. I was dressed as Harley Quinn (jester version for those who care) and he had me tied to the bed and blindfolded and pounded me like crazy. So. Yeah. That was nice.“

2

Fail:

“A girl sharted on my balls.”

3

Win:

“Probably the first time I smoked before having sex, we took our time with everything and we were both able to finish multiple times and afterward, we fell asleep while eating little Caesar’s, 10/10.“

4

Fail:

“My ex and I were laying on our backs (nekked) on the bed after doing some stuff, and her cat ninjas up between us and swats my decompressing boner.”

5

Fail:

“Met this gorgeous redhead in a club, went home with her (it was clear that she was expecting some sex)…was so drunk that as soon as we entered her place, I passed out and fell face down right into the middle of the living room floor. Woke up the next morning with a note saying : ‘GTFO.‘”

6

Win:

“Had sex with a fireman in his fire truck. That was super hot“

7

Fail:

“I almost broke my (now) husband’s penis the first time we tried it doggy-style. I have a very large butt and we were having trouble lining up properly and I threw my head back and accidently head-butted him. His nose hurt for like 2 weeks. We laugh about it now lol.”

8

Win:

“I went on a really nice first date with someone and at the end of the date he suggested we go back to one of our places to “talk” and I said yes.

Gahdamn he took me to pound town. 3 hours of kissing, fondling, grinding, fucking, then fucking again and again. He was the first guy that actually cared enough to make sure I orgasmed, more than once.

I’m seeing him again this weekend after a month-long absence and my vagina is tingling thinking about it already.“

9

Fail:

“A little sexy time action with a lady friend. Shes like 4’11 and i’m close to 6’4 so there is a bit of a size difference. It’s getting down to the nitty gritty and she asks if i have any lube. I tell her I don’t. She asks about cooking oil. I think about it for a second and realize I do have some. Walk into kitchen take oil out of cabinet and lather my hands in the stuff go back start banging her with the oil and start doing the deed. Well in my haste to spill seed I guess I had grabbed the extra virgin olive oil infused with garlic. Didn’t take long for the entire room to smell of sex and garlic. Maybe if i were Italian it would have been enjoyable, she on the other hand was not amused.”

10

Win:

“Honeymoon. Sex on the balcony on one of those big comfy round outdoor couch things. It started raining halfway through and we just kept on going. It was awesome.“

11

Fail:

“I recently asked my boyfriend to try talking dirty in the boudoir. So last week, we’re in bed, and mid-thrust he says “Ohh fuck, I love your……vagiiiiinnaaaa.” We both hate the word “pussy” and I guess in a pinch he couldn’t think of anything else.”

12

Win:

“Making this 35 year old milf squirt for her first time. Best feeling.”

13

Fail:

“Sexy times after I cooked spicy food. There was still a little habanero pepper on my hands, which ended up inside of her…..”

14

Win:

‘When I was 18 I was at this girls house and it was just me her and her friend. Out of nowhere (I had never hooked up with either of them), Girl 1 says “let’s see how quick we can get Joelasdome hard”. Being 18 I was hard before she finished the sentence, and they proceeded to give me blow job, both of them, at the same time. best 5 minutes of my life.”

15

Fail:

“One time I got drunk with the girl I was dating at the time and she said ‘hurt me’ and instead of like, slapping or spanking her I just pinched her really hard.”