I guess you can say that I did this once, a few years ago.
I had gone on a weekend trip with some friends to a nearby college town, and we hit some of the bars. In one this young kid (he was 19) kept hitting on me, and I was kinda drunk and teased him back. When the bar closed I needed to go back to my hotel but my friends had already left, so I agreed to let the kid walk me back (it was about a mile away).
He kept going on about how hot he thought I was, and how he wanted to know me better (of course I know what he meant), but kept going on about my friends ditching me, and how I was going to pay for the motel that night since we were going to share (this was BS, the room was already paid for of course, I was hoping he would get the hint and bail).
Instead about a block before we got there he pulled me between some buildings, and said if I made him feel good he would give me enough for the motel room. Well, why not I decided, and opened his pants and pushed them off his hips. He was around 6" long, and just big enough around that my thumb touched my fingertips as I started to jack him off.
We were kissing the entire time, and he was pressed back against the wall as I jerked his cock. After about 5 minutes I changed hands, and pulled open my blouse, hoping to give him some more initiative to finish. He immediately went at them, squeezing them almost to hard, and I stroked him faster. I was also squeezing my thighs together at this time, and could feel him start to throb in my hand.
He moved his head and practically devoured my nipple as he started to moan and jerk his hips forward and back. I could feel him splash on my wrist as he started to cum, letting go with a huge load which I then rubbed all over his now softening cock.
A few more kisses, and we put ourselves back together and finished the walk to the motel. In front he pulled out a couple of bills, kissed me again and walked off home. I went in (my friends were already there and in the beds - they later told me they went back early so I would be left with the couch) and took a shower, after counting the $120 he paid me for a handjob.
If I had only thought of that when I was in High School, I could have been rich. hehehe
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