My first time was great. I'm sure I've posted about it elsewhere on this forum, but just for the lol's;
he was 14 and I was 15. We'd talked about it here and there, but finally decided to do it after discussing Final Fantasy 9. A mutual friend, ex, and I were all in his little brother's room (it was one of the only rooms upstairs- I've no idea where his little brother was). Ex and I were on the bed (I guess friend was there to deter parental units as "they wouldn't have sex with their FRIEND in the room"... apparently we were horribly desparate) while friend sat on the floor with his back to us playing FF9.
First, he had trouble with the condom.
THEN he couldn't get it in. He kept stabbing me in the thigh, places AROUND the vaj, once in the stomach, then finally decided if he HELD it with his hand and guided it in it would go.
By this time, I had a fair amount of the giggles. I felt it "pop" in, but was laughing too hard to notice any pain.
He asked me "Is it in yet?"
While I told him "It tickles."
He tried to pump a few times but couldn't get it up. Which made our first time even more hilarious. Because we'd remained friends YEARS after we broke up, at parties and group get togethers, this story often comes up when the booze comes out. His now-girlfriend thinks it's hilarious,
and the friend who was stuck in this awkward position continued to bear witness to COUNTLESS episodes of sex in our friend group, earning him the nick "Nookie Fairy".
I <3'd my first time, and in all seriousness, I wouldn't change a thing.