What is your most awkward moment with the opposite sex

[Cardsfan]

Was about 16 or 17, me and a couple of mates were sat in my bedroom playing Halo on the original Xbox
One mate, James who was a bit of a lad got a call from a female who he went to college with. Said she was home alone and up for a laugh. She heard us in the background and asked to speak to us, had a quick chinwag and ascertained she wanted the D.
She lived in a village a couple of miles from my house, so we had to leg it across the countryside in the middle of the night trying to down a couple of bottles of Scrumpy Jack to try and catch up to her tipsy state (only 2 of us, our other mate chickened out). We got there, she opens the door, I'd mark her up at a 6 or 7, punky, my type. Though I think the Scrumpy Jack marked her up a few.
So there we were sat in her lounge, we're chatting away and she randomly sticks a porno on. From what I remember it was okay, nothing to write home about. She wips her top off and we get down to business. Was okay, actually brilliant for me as I'd just got out of a longish relationship so I was going for it.
aaaaaaanyway, after an hour or so of trying to avoid mid sex eye contact with my friend James (We did high five at one point, which makes me cringe to this day) He stays in her room for the night and I kip in her little brothers room which isn't weird or groomy as it was a free house remember? Wake up in the morning, and this random fella walks past, I'm like "Alright bud?", he just grunts and walks downstairs and slams the front door. Turns out he was her older brother, he'd come home in the early hours to the porno on the main menu loop, and used rubbers all over the place.
It wasn't that awkward really, just wanted to impress you guys with my nohomo teen sex story. Just to note, a threesome with another dude isn't remotely gay unless you touch pinkys, which didn't happen I swear.

Was this the same "friend" who shagged the 50 year old?

 

[Whitechapel]

Was this the same "friend" who shagged the 50 year old?

That was a different friend. Fun fact, the last 2 ladies that friend has been with is 85. What a stat.

 

[Renegade]

Rooney-esque.

 

[Magic]

Accidentally stood right next to someone who I'd chatted with on Tinder (who I had little interest in and had ignored a few of her recent messages) in M&S the other day. Forgot she worked there. Managed to escape without saying anything but didn't enjoy that at all.

 

[The Alex]

This goes back to my sixth form days, I was taking part in the Duke of Edinburgh awards and was also trying to get with this fit older bird who worked in a care home, so I arranged for us to do some voluntary work with her to go towards the DofE. Anyway, I managed to blag a date with the girl. Next day I'm in the sixth form common room and I fell asleep, shattered from the night before in the care home. My dick head mate Jay thought it would be funny to put veet down my boxers and my pubes preceded to fall out, my date was later that night so if things went well she would have seen my bald bits and I didn't need that being much younger than her. So I decided to stuff a wig down there. Anyway, after the date things heated up and I did my best to stop her but she slid her hand there there and she pulls out the wig. She was in complete shock, she left and I never heard from her again.

 

[T.A]

That's from the inbetweeners.

 

[TractorBoys]

 

[Dave-Vale]

Shower and broken banjo string. I'm
not talking about the kind of banjo you play either.

 

[Stevencc]

I don't get it.

 

[TractorBoys]

Shower and broken banjo string. I'm
not talking about the kind of banjo you play either.

Been there done that.

 

[Dave-Vale]

I don't get it.

Really?

 

[Stevencc]

I googled it.

Ouch.

 

[Meadow]

Explaining that the former Mr Meadow had walked out on me a week before our second offspring was born. Arsehole.

Thankfully the second and final Mr M is a different beast.

 

[Dave-Vale]

I googled it.

Ouch.

Yes. There was so much blood.