Yep...well, kinda. Not at all hot but waaaaaay back then I was a young boy trying to practice...
I was 17, she was 35...the mother of two of my younger friends.
I had been getting play from her for months, she was always teasing and dropping hints...
One day when her kids were in the backyard playing she called me in the apartment to talk to me....we were talking and flirting and I said if she keeps on playing with me I'm going to have to do something about it. So she started kicking game at me and asking me how serious I was. I told her I was completely serious. She came up to me and started rubbing on my arm and getting close. Next thing I knew...we were kissing and she had the upper lip stubble thing going on...didn't notice it til then...kinda put me off.
Anyway...I'm too into feeling on her t*ts and ass to care...she pulls me to the bedroom and we dry hump and kiss for about 10 minutes. She starts moaning "ooh papi...I want you" and taking off her shorts. I didn't have a condom with me so I tell her and she's like "I don't care...I want you in me papi...please!!".
At this point I'm like

because I didn't have a condom and I knew she been fukkin the mailman, my friends father and who knows who else.
So I had to back out and she was mad upset and frustrated cause she didn't have a condom either. I knew enough not to go raw in her cause I know I woulda busted all up in her and wound up with a short puerto-rican kid I didn't want from someone I didn't wanna be with long term.
She stomped out the bedroom and went to the kitchen to smoke a cigarette. I cleaned up and went outside to hang with my friends. I shoulda got some head before I humped her but I wasn't thinking...walked outta there with nothing but blue-balls from rubbing up on her. Crazy thing is, she had a car and I had money, we coulda easily gone to the store on the corner or even down the ave and gotten some rubbers and boned our brains out if we had more time...Her husband was going to be home soon.
I learned to carry protection at all times after that...I wasn't about to miss out on some booty again because of lack.
Went back to hang with her kids multiple times after that day but she never even let me flirt with her anymore.

Oh well...life goes on.