Awkward Sexual Encounters: Final Round

My most recent awkward sexual encounter (post-sexual encounter, to be specific) involved me trying to show my boyfriend I had learned how to queef on command.

After I called him in the room to unwillingly watch me perform this horrifying act, I knelt on the bed on all fours with my ass in the air, and I pushed really hard. What happened next was not at all what I expected, but was something I feared. Did I queef? No. I fucking pissed. I fucking pissed all over the bed and myself with him standing there watching.

I was 16 when I got my first real girlfriend. She was 20. This should have been a red flag, but fuck, she was probably experienced at something so what the hell.

We took it easy for a couple weeks, and then one night I found myself in her room at her parents house doing the two-knuckle shuffle while she squirms and whispers in my ear that she's going to come and holy fuck this is awesome.

This continues for a month. With no reciprocation. As much as spinning her on my fingers like a Globetrotter with a basketball is fun, my penis is feeling very underappreciated. So one night I say fuck it and move her hand to my crotch while we're making out and soon I'm getting a handjob.

This is the worst handjob ever.

She is alternating trying to drive my dick through my pelvis and trying to start me like a lawnmower. I'm kind of squirming which she takes as pleasure and now she's doing it harder and I'm actually lifting off the bed with each stroke. This is like a stabbing in a Halloween movie.

I've had enough and whisper something about moisture or lubrication, trying to subtly hint at some mouth action. I'm too subtle, and she takes the opportunity to lick her palm.

She turns the diamond ring on her finger backward by accident in the process, unbeknownst to me. So when she Grips It and Rips It, she literally rips it. About a three-inch furrow in my penis. After a curt "Jesus fuck STOP" I survey the damage. It's like a reverse parting of the red sea. My dick is bleeding and my mind is having none of this and trying to curl up in the back of my skull.

I need to get to the bathroom, stat. Which is across the living room. Which is occupied by her parents watching TV. And my pumphandle is dripping blood. I spot her panties on the edge of the bed and with a flourish they are tied in a neat little bow around my johnson. I put my pants on and marched across that living room like a boss.

Where I tried not to sob like a child and spent 10 minutes trying to wash my dick in their sink.

It happened when i was 18. I had broken up with my first girlfriend a few weeks previous, and we only had sex a handful of times. She was my first and I was still pretty inexperienced. I'd led a pretty sheltered life up to that point and didn't have many friends, so my social skills were slightly more nonexistent than they are now.

I was on a night out with friends from work. We were all in a club and after a couple of hours i was pretty drunk. I joined one of my friends at the bar as she ordered more drinks, then she started talking to this girl she knew. This girl was just plain looking. She seemed shy and looked out of it so i assumed she was pretty far gone. My friend and I take the drinks back to the table, and as an unusually bold move at the time I thought I'd go over and talk to this girl. She doesn't respond much, and her speech is slowdeep; again, I put it down to her just being drunk, as she's also pretty incoherent. I'm doing all the talking and she's just standing there smiling and responding sporadically. It's getting late, and every time I'd gone out clubbing I'd never 'pulled,' so i ask her if she wants to get out of there and go back to her place. She just smiles and nods and I tell my friends I'm going.

As soon as we get outside, things start clicking into place. We stop by a take awayout place (depending where you live). I hear her ordering her food and i couldn't quite hear her speaking without the loud music drowning most of it out beforehand. I didn't realise at the time that she's pretty well known about town, so when people see me with her I'm just getting a lot of looks, mostly horrified. Things start dawning on me that this girl wasn't drunk, she'd had one drink the entire time we talked and didn't even finish it before we left. But I had spent a good hour with her up to that point, and I didn't jwant to be rude and bail in the middle of town, seeing as I asked her to go back to her place.

I should have bailed, I should have made my excuses and left, but as the light bulb hit me, I thought I'd at least make sure she got home safely. But at the same time, it had been a while. I was naive and thought 'would it be so terrible?' Well, we got back to her place and it was disgusting. As soon as I walked through the door I almost gagged. The whole place was dirty: used dishes on the kitchen counter, dirty clothes everywhere, general stains and mess everywhere. It looked like something you see only on TV programs like Life Of Grime, and here I was experiencing it in person. Am I that desperate? The alarm bells are going off so much i should have just ran back out the door. But I didn't, I wish I had.

I ignore the mess. She wants to go for a bath and starts running it and strips right in front of me not caring. I don't know if it was the drunkenness or the sight of seeing my second-ever naked body that flicked the alarm switch off momentarily. She didn't have a great body, but it was a body and it was naked. I asked if I could join her, all she did was nod. So we just sat there in the bath, just sitting, nothing sexual, just sitting. Alright, was this worth it, I thought? No, I told myself I should get out of there. Did i? No ...

So after a few minutes we get out the bath. I grab the cleanest towel I can find and dab myself dry. She says she wants to go to bed with me. I should have just called a taxi. I was just wanting to go, my mood was completely dead at that point. I figured I could just get a few hours sleep and then just go. She lays there naked and looking at me, so i ask if she was meaning that she wanted sex and she said yes. But then I said that I was feeling pretty tired and that I should go.

I had already gone way too far. I shouldn't have even gone into her apartment, but part of me was thinking I was doing a good thing by seeing her home safely, and the other half was thinking it's been a while and she was just a little slow. But the more I saw, the more time I spent with her and at her place the more wrong it felt. I called for a taxi and went home. Was that the last of it? No...

For a few weeks afterward, she called into where I worked occasionally looking for me and telling my manager and co-workers that she was my girlfriend. The mutual friend told me that she is certified mentally retarded and that she knew her from when she used to volunteer at a center for adults with learning disabilities. I was polite to this girl when i saw her but she would not leave me alone for weeks.

Maybe not a true sexual encounter in a sense, but i did get crabs from her disgusting bed sheets...

once when i was in grade 8 i had this huge erection. my penis is and was 9 inches long. it was during lunch break at school. i was standing alone. i had no idea how to hide an erection so i just let it stick out. this girl saw it and i didnt see her see it. the next day when i came to school this girl was staring at me smiling for a while then she told me to come over to her. she had friends with her. i forget what we talked about.

My wife likes frogs. One day she observed that when lying on top of me she kind of looked like a frog. I told her never say that again, sex resumes, then she looks at me right after she has an orgasm and goes "Ribbit!" and flails like a frog on a frictionless surface.