Excellent stories so far, especially the first one. If it were any juicer, I'd be jacking off right now.
Mine's probably a bit boring, but I'll take a swing here.
We've all grown up knowing hot chicks that were either a bit too old for us or, unless you're the high school QB, wouldn't give you the time of day. There's this one, who fit the 'a bit older than me' category...not creepy old, but 'old enough to be your mom's youngest friend' old. She was fine as all fucking get up. Big booty, thick thighs, made a habit of wearing hooker style miniskirts, the look that made guys say 'DAMN!!' all day long. She looked like she could've been in rap videos.
For YEARS I drooled over her every time I saw her. I actually tried to make a move on her years before, at the club. But I was such a nobody that she probably didn't remember (cold, hard rejection, fwiw).
Fast forward a few years later. A little older now, low 20's, some definable muscle structure. On a rare night, I didn't feel like going out to a club. Had a cousin of similar age who wanted to go out. I wasn't feeling it, but he was soooo insistent. Oh, fuck it. I'll go if shut you the hell up.
We go. We're at the club. He's doing his thang, dancing, drinking, flirting with chicks, the whole nine. Meanwhile, I'm in the corner, babysitting a drink, watching the clock to when this is all over. Lo and behold, guess who comes walking up. Yes, it's the big booty, high school queen, rap video body chick that would've give me the time of day years ago. She's wearing one of her little signature, way too short, hooker skirts.
Truth be told I wasn't expecting much out of situation, but she's hell bent on carrying a conversation with me (actually pulling up a seat next to me, even violating that personal space area). I feign juuuust enough interest to maintain said conversation. It drags on. So finally, club is approaching closing time. She's still talking to me, and start throwing hints that she may be too drunk to drive home (she wasn't TORE UP slobbering drunk or anything...but a bit tipsy). Then she suggests that I follow her home, to make sure she gets there safely.
Mind you, when it comes to women, I'm the no hint gettingest mf'ker walking the entire Earth!!! Women can't be subtle with me. They have to pull my dick out and start sucking it for me to get a hint that they want to do something
[Woman: after many failed attempts to flirt, pulls me out and starts sucking.
Me: Ohhhh, you wanna mess around huh......ok, I see where you're going with this!]
Oh, but on THIS NIGHT, I was a complete 180 of myself. I KNEW EXACTLY WHERE SHE WAS GOING WITH THIS!!!
I found my cousin, dragged him to the car, and was like, COME ON, MAN!!! WE GOTTA GO!!! BOY, COME ON!!!! I'MA LEAVE YO ASS IF YOU DON'T HURRY UP!!
(The things we do for pussy, I tell ya)
[I didn't want to lose track of her, and have some other fucker end up with her]
We follow her home, I drop him off, and head over to her place.
I end up TEARING THAT PUSSY UP for for the next 2-3 hours (wee hours in the morning, after club closing time). Mish, doggy, cowgirl, over and over (she's one of those moaner/screamer types, too, as it turns out). We started off using a rubber, but not long after we ended up going raw, completed with me cumming deep inside of her by the end of it.
Talk about a night to remember, one that started with me not even wanting to go out at all.
This was the first a few encounters between us, before drifting apart and moving on in life.
Now that I think about it, it was kinda like winning the lottery.