I hitch-hiked a lot when I was in college, and met and masturbated with several men....
Your story of masturbating sex on the road rang a bell for me. When I was first in college, I would hitch to visit my girlfriend 300 miles away. In those days, hitching was more common, and safer, and a broader group of people would pick you up. I enjoyed talking about sex-with anybody-and had some great (hot) conversations on the road.
One guy showed me pictures of his wife, naked, and asked if it turned me on. When I said it did, he asked if I wanted to masturbate with him. I was a little bit freaked out, but also turned on by the idea of looking at his wife...and masturbating on her. So we pulled over, and he watched as I unzipped my pants and pulled out my cock. He was rubbing himself in his pants, and staring at me intensely. He kept asking me if I liked her hairy pussy, and told me it was wet and soft and stinking, over and over, and I came pretty quick.
Then he unzipped his pants and jacked himself off in seconds.
He told me that he told her that he wanted dirty pictures of her to show guys, and he would tell her about me jacking off while he was fucking her, and then, for sure, she would cum like a slut.
That was my first encounter, and then I began to wonder every ride if I could masturbate with the driver. I would drop 'hints' when we talked about sex, like saying how hot something made me, and when I wasn't scared, letting myself get a boner and even rubbing it. Sure enough, on the next trip, a guy picked me up who said he was married and pretty soon was telling me about how on his trips he would go to topless bars and porno theaters because he didn't have any sex with his wife.
He told me about how in those places, guys would masturbate each other, and he asked if I ever had done that. Of course, I hadn't, and the next thing we were on the side of a road a half mile from anywhere, and he was pulling off my pants. I got hard as soon as he pulled off the highway, and was totally stiff when he pulled my underpants off. His hand was on my cock in an instant, and, fuck, it was so hot to feel it. He played with my balls and stroked me and then pulled off his pants and told me to do him, too. He was extremely hairy-thick black curly hair-and his balls were gigantic when I grabbed them. As soon as I felt him there, I came in his hand, uncontrollably, and for about the first time ever, made a big noise.
I don't know if he was nervous or I didn't stroke him very well, but it took him a long time to cum, like ten minutes or so. I was so hot feeling his cock and playing with it, and pretty soon I was stiff again, and he was stroking me, and also saying lots of dirty things to me. I could feel myself about to cum, and was trying to hold on, but couldn't. And then-wow-I felt his cock get really, really hard and he began to pump his hips and moan, and we were both grinding and stroking and I felt his cock pressing in my hand, pumping and pumping cum.
We sat there, cum in our laps, red dicks swollen and oozing cum, his dick still in my hand. I could not believe what I had just done and was kind of ashamed, but it was so fucking hot, that was mostly all that mattered. He was heading to the same city as I was going to to see my girlfriend, and he gave me his phone number.
I wasn't going to call him, but when I was about to go back, I called him. He met me at the edge of the University, and said we could drive to a place he knew was safe. Before we got there, I had pulled down my pants and offered my boner to him to feel....