With the now-fiance.

I had just broken up with my cheating exboyfriend when a coworker wanted to set me up with his cousin. (Red flag 1) Said cousin was in his mid thirties and I was still a college student. (flag 2) Coworker said his cousin was a pretty well off business owner who was a home body. (Flag 3) I said why the hell not and met…

My girlfriend and I decided to check out this newly openly sex club, mostly out of voyeuristic curiosity. We weren't swingers, but we both liked porn and the voyeurism / possible exhibitionism angle appealed to both of us.

My now-husband and I had a lot of sex in the first six months. And I mean a lot. We averaged twice a day (we had a little book where we kept a tally, which seemed super romantic then and now strikes me as a little creepy) which is particularly impressive given he travelled for work. Our daily record was (still is) 7,…

My date farted while I was rimming him. He was mortified. I died from laughter and then resumed shortly after collecting myself.

Ohhhhh boy. This is a bad one and I do not feel good about this.

He was younger than me, and a virgin. That night in the hotel, we got drunk with the brass section and straight vodka, with my targeted paramour also making a water bong out of a pop bottle and a trumpet mouthpiece.

I just wanted to highlight the part where this story became brilliant. So many followup questions! Was…

I definitely take the cake on this one. That time that I nearly lost my virginity. I was 16, first real boyfriend that sexy times were involved with and we'd been together a year and done almost everything except PIV sex. So this one morning he took me shopping and the youths that we were, we couldn't keep our hands…

Take your pick on which one is the most awkward display of sex that you have ever heard of. This first one can't even be considered sex because we never got to anything.

First year of university, I'd just broken up with my high school boyfriend (and only sexual partner) and was feeling like sowing my wild oats a bit, if you know what I mean. And lo and behold, I had a trip scheduled - with my old symphony! (Yes, this is practically a band camp story.) The clarinet player who sat…

Early on in my last relationship I discovered my boyfriend liked to have his nipples touched. One night we were getting going in the dark and I felt around for his right nipple. He sort of stiffened and I thought maybe I wasn't making the sort of contact he liked so I whispered something like 'tell me what you like'…

This happened to my best friend in high school. He was having sex with this girl he had been dating a little bit for the first time. She insisted she wanted to but was lying there stiff as a board with very little movement and her eyes closed. He kept hearing her mutter something under her breath over and over. He was…

I used to have an 8 gauge tongue ring and my boyfriend used to always wear a chain. I liked to change my jewelry so my latest tongue ring at the time had a little skull with rubies for eyes as the top "ball" of the bar. We were getting it on pretty hot n' heavy and I decided that I wanted to run my tongue up his chest…

I'll give you awkward. It, of course, involves being a teenager.

I don't know if this is technically awkward but I was 18 and a freshman in college and I really wanted to lose my virginity. So over Easter break (Jesuit college- that time was to be spent with God), I hooked up with a guy I had been seeing off and on who was a senior in high school. We hadn't gone to far in the…

I had a guy stop in the middle of doin' it doggie-style, pull his pants back up and say, as he walked out my front door, "I'm sorry. I'm used to fucking strippers and this isn't working for me." He was referring to my pubic (and probably bum) hair, which he had already made several comments about. I am fair and even…

I used to hook up with this hot but also kind of creepy older firefighter in high school. We would go for drives and make out and pretty everything but PIV because I was a virgin and I was like "no fucking way am I going to want this situation to be a memorable experience, but I'm horny so whatever finger me in the…

A guy I saw in college had problems with taking sleeping pills (for fun) and then not being able to perform because he was so out of it. This was very annoying. One time he gave up and started using his fingers, but he was so damn quiet and mechanical in bed that I could practically hear dust rolling across the floor.…

I was seeing this girl when I was a freshman in college. Not serious, but not un-serious, you know? Up to this point, we had not really gone past first base, but had bee sleeping together (in the literal, bed-sharing sense) off and on for a few weeks.

Does it count if his P didn't go in my V? Hooking up in the back of a Pontiac Vibe, because I am nothing if not classy. Things were heading in the sex direction, so I reach for his fly. He warns me that he "isn't prepared" and "didn't think this was going to happen." I reassure him that it's fine, assuming he…