+K for the most awkward

Ohhh gosh. Well I had been seriously dating this girl for like 4 months but we couldn't have sex due to a bad knee injury my gf at the time had from skiing. So after 4 months of no sex i was absolutely ready, and stoked. So we were at her lake house and her parents were out and we decided the time was right. She got my clothes off, i got her clothes off and I wipped out my condom from my wallet which also, had been there since birth, and i laid back, and she got on top of me and i started trying to put it on, but I wasnt hard. So she did her best to get me hard and...not a thing. So I pretended I was hard and I got the condom like halfway on after like 10 minutes of frustration and stalling, and then she attempted to climb on board. But no, wouldnt go in, wrinkled condom, flacid penis. She tried for a while until she started laughing. I was so upset and let down and, there arent even words to describe. I ran off to the bathroom and told her i just had to pee. By the time I got back in she was still laughing. I put my head in a pillow and laid there, in shame for like 30 minutes. After that she tried to cheer me up and laugh about it but I was so upset. I told her I needed to smoke a joint, so I went, rolled up a fatty, and smoked it on her porch. But the next day round two was on and I did it! So I felt much better...Ahh fuck. I dont think I have ever told this whole story. Hahahaha
 
Haha my "Others rate you" karma thing went from 5.68 to 7.23. I need to tell this story more often.

 
i bet you avoided your mom for a while? the sort of same thing happened with my dad when i was doing things with a chick not sex but my dad thought we were it was so awkward.
 
My dad would come High Five me.

And heres my story:

I was 17, and wasted off moonshine and natty ice at this thing called Trail Day's, it is an Appalachian Trail festival in southern Virgina. At the time, I was thru hiking the trail and I hadn't beaten it or even seen girls in a long time. So I'm chillin by the fire with a bunch of people (keep in mind I'm pretty wasted) and this girl who is a little overweight is literally falling into the fire. So she leaves and I leave around the same time and we end up walkign around and talking to eachother, and she asks me "Hey little boy are you a virgin" I say no, But I am. Anyway....

We walk back to her tent, which since we are both backpackers is a single person affair, with very little headroom. I try to get my clothes off but I cant in there, so I do it outside real quick and get back in the tent. She has her pants off by the time I get back in, and I try to eat her out. Being a young kid I wanted to make sure htings were good you know? She say fuck that shit, so I just start banging her. I couldnt cum, but I could sure make her scream. (This is a problem which still persists to this day there has only been one girl who could do that do me, out of 10) So after a while of some awkward missionary in a pitch black tent, I pretend to be done because I know its not gonna happen and I'm getting tired.

Now, since this is a festival, we were in a "tent city" and a girl screaming for joy in a tent wont go unnoticed, tent walls are just thin nylon. SO, I get out of the tent like a G, its pitch black, and when my eyes adjust there is a CROWD OF DRUNK FUCKING HIKER TRASH clapping. I am standing there naked not knowing what do do... so I just say thanks grab my clothes and walk away naked. To this day I dont know her name, other than her trail name, Bobcat. For the rest of the festival I was known as "Bobcat fucker"

But hey, how many people can say they got a standing ovation for the first time they had sex?
 
my buddy double teamed this chick with his brother. the next morning he woke up to her bitching about where her pants were she couldnt find her pants, so he gets up to go take a piss and some other dude was passed out on the floor outside there door with this chicks pants on.
 
i got a good one, but since my actual losing virginity story isnt so good, ill give you the one of how i broke my gfs hymen.
so i go over to her house and what do i know, but she is wearing sweatpants(international sign for fooling around...EASY ON EASY OFF!)
'lets watch a movie'...thats the 2nd sign i heard soon after walking in the door.
so we header downstairs after making chitchat with the parents...
so a bit later we start fucking around, and i start giving her the snack sized kit-kat(2 fingers for the slow ones). she keeps telling me to go as hard and deep as i can so, being the kinda of guy i am, i fucking giv'er.
some time passes by, and my mom is coming to pick me up soon(cause im a pimp like that)
her parents tell me my mom is upstairs so i go, and my gf says 'ill be there in a sec im gonna go to the bathroom'...so i go upstairs.
for some reason she WILL NOT come upstairs, and finally when she does he is like covering her ass, and her breasts up...she says bye and runs upstairs.
turns out i gave the peoples finger to her hymen and she was bleeding...and my hand (which apparently had blood all over it...it was pitch black downstairs ps) was grabbing her ass and boobs after...leaving a PERFECT handmark on both...which is what she was hiding. so after this our first time having sex was dope!
thank fuck she decided to go to the bathroom real quick before comming upstairs...
 
god damn ns i want more good stories.

mine is nothing special. parents werent home. me and the gf were fooling around and then it just kinda happened. i lasted a decent amount of time and it was all good. i thought about peeing i her bum, but didnt happen.
 
My friend was banging his girlfriend when he unknowingly popped her cherry. A few seconds later he decided to go down on her. You guys can guess the rest...
 
You must log in or register to reply here.
Back
Top