What was your most awkward sexual experience?

I decided one day that I would sleep with a guy to prove to myself that I wasnt a lesbian. Guy started to undress me, I had a panic attack, guy leaves the room and tells his friends.

Lesson learned: don't push yourself into a situation because you're afraid of who you are.

Trying to have sex whilst very drunk. Me and my girlfriend after a night of partying and drinking, decided to go at it one time.
It was very bad. I mean... there is no reason to even describe. Two very drunk people can not have quality sex XD

Farting during an orgasm

Late one Sunday night, about 25 years ago. I was fucking my girlfriend in a car at a local 'beauty spot'. We were both naked and sweaty and when about a dozen cars turned up and lots of people got out and wandered down to the lake. It was a local religious group using the lake for a baptism. We just crouched as low as we could, convinced that if the nutters caught us they would hang our naked bodies from a tree. Happy days.

I had just been cleared to have sex by my gyno after having my first baby. He was sleeping so we figured set the phones to silent and go take care of the frustrations that were building for a month and a half.

Well unbeknownst to us both of our mothers had called and left a voicemail saying that they were coming over. They both had a spare key to the house in case of an emergency.

Well they opened the front door and walked in to find me spread eagle enjoying every inch of his cocktail on our couch

Needless to say they dropped the new pack and play and don't have an emergency key any more

I was fucking my girl on a table so hard that she popped and went flat. Then to add insult to injury, the manager told me I couldn't come back to that Arby's.

Looks like someone is going on a thumbs down spree.

Probably my family friend who stayed with us for months. She was thirty and I was about 20. She ended up initiating it and I was thinking in my head, "Erm, ok." It was in the living room when my family was sleeping (ish) and the door was a see-through glass one. Regardless, I wasn't fussed by it being so open. So we get to it and I'm doing most of the work for about three hours, we're perfoming different acts, positions, etc. She's just getting sofa completely wet which was funny to try cover up afterwards but I digress. The sofa's wet, I'm on top of her, she's biting in to my shoulder, scratching my back (sounds like rape...I know. It wasn't. Calm down) and so on. So I'm getting eaten alive which was pretty interesting.

Even oral done nothing. She done the whole thing where she makes herself down to "the area" and performed oral and I was just not understanding why I wasn't enjoying it. So I ended up having to somewhat fake without doing the exaggerated porno fakery thing which is obvious.

Hours are passing and I still haven't gotten off yet but I'm still able to perform (erect) and that's confusing me. She's trying to kiss me when we're doing doggy and I push her back down unintentionally but intentionally if that makes sense? I hate kissing. We ended up stopping after three hours and so and so minutes. I still hadn't gotten off.

She ended up trying to get more sex the next days aswell and wanted us to go to the woods near our place because she couldn't enjoy it fully due to having to keep quiet in the house which led to her telling me to stop if she was enjoying something I was doing too much.

I only really got off once with her and that's when I was having to fixate on other things. I felt kind of guilty by it but happy by it. Even if I didn't really enjoy myself it appeared like she did but having to fake through it a lot made me feel like if I told her I wasn't satisfied with her that I would hurt her feelings.
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Another time would be with a guy. I'm not gay (possibly bisexual?) but I ended up with the same feeling. Not disgusted by the homosexual acts but just unsatisfied. He performed oral on me while I was drunk. Another day he tried to pull me on to the couch and wouldn't let me leave until I gathered my wits in my drunken state to tell him that we'll fuck sometime this week. Little did he know I was moving that week. >:) Mwahahaha.
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Another time would be when I was outside with this girl walking home from the bar. She made some lame excuse about not wanting these people walking by to see her so asked me to hug her. So I did, help her out. Next thing she's kissing me. So whatever. Next thing she has her hand down my trousers, so whatever. I reciprocate with putting mine down her trousers. I wasn't that interested in her so I pulled her hand out of my trousers and kept mine in hers because I might not of enjoyed it there and then but may aswell continue if she did. Then we ended up having sex outside in a somewhat open space while it slightly rained.
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Another time would be with an older woman, mid thirties or late thirties. We met at a house party and I ended up having sex with her in the bathroom while her son and nephew was in the other room. He later walked in to see us making out.

Honestly, I think most of my sexual experiences were weird. Obviously they're not "That" weird, people do far more weirder things but I've never actually just had sex in a normal bed without any other aspects involved...I should try that at some point.

Long story with too much detail...Forgive me, I'm cleaning and used this as a distraction.

wife blew me in front of window as neighbor was watching

having sex with an empty stomach ,was so bad and the results were so poor ,and the girl was like "are you sick?"

Losing my virginity to Seinfeld /Family Matters..sigh

Fucking a guy who had a really small penis and was unable to orgasm. I had only been with one other guy at the time so no, his penis truly was objectively small (like, 3 inches and very thin) so not only could I really not enjoy the sex but I had to stop after like half an hour of really trying. I could barely tell if it was in...

That was EXTREMELY embarrassing. In hind-sight, however, I am not sure if I was the one who should have been embarrassed... call that a lame ass comment but either have the skill or the equipment. If you can't have one have the other come on...

This was when I was like probably just turning 18. Was hanging out at my friends camp with a bunch of people. I had gotten out of the hospital that same day and was just feeling sick, but was still smoking weed and drinking whiskey (and eating sweet chili heat doritos)

Dude that went to highschool with me was buzzing and starts play wrestling with me and we both got turned on. We climbed up into the top bunk bed of the camp and he starts fingering me terribly, like shit was terrible. At one point he fingered my belly button because I was trying to get him to stop and he was confused as to where his hand was, so that almost made me laugh and ruin the whole hook up. I'm stoned as fuck and holding back my laughter so I start blowing this guy, and he's got a big ole hammer on him and I'm underneath the covers and its hot as the devils dick under there.

I start getting sick because of how hot it is, how drunk I am, and all these hospital drugs still getting out of my system so I pop up out the blankets and say "I gotta stop I dont feel so good" and hes just like "no don't stop it feels so good" and he's just pawing at me trying to get my shirt off and my pants and I just lean over the bunk bed and puke my guts out. Sweet chili heat whiskey puke goes all over the floor, on my tits, almost on my friend who is on the bottom bunk.

Long story short, dude fucked off for like an hour then tried to hook up again and at this point I told him to take a fucking hike. Hahaha one of the worst sexual experiences of my teen years.

Also my best friends saw my tits that night cause I was so fucked I just took my puke covered shirt and bra off and walked out in the rain to my friends car and she gave me a new shirt. My best guy friend was on acid that night and just tripping hard and not understanding what was happening hahah such a clusterfuck