At the time I was 22 driving home for Christmas from Florida. I had been driving a lot longer than I should have been, I had been jacking off since I was fourteen, I always had a fantasy of doing another guy, now I'm as straight as an arrow.
It was late, I was going through the hills of West Virginia and I came upon a hitch hiker in the middle of the night. I drove by him then I decided why not, he would give me someone to talk to, to keep me awake,
I stopped and he came running up to my truck. I asked him where he was headed to, he told me to Baltimore, I said no problem, I'd let him out on the road which he needed to take. Now he was small build, boyish looking, kind of scruffy looking, maybe 120lbs, as we drove down the highway we had some small talk, then there was nothing. I looked over and noticed that he was sleeping, well so much for that. I kept looking over at him wondering how big he was, what would he do if I just reached over and started stroking him through his jeans, well I came to my senses that I was really too nervous to do anything like that.
After a few hours he woke up and asked me where we were. I told him we were almost to the road he needed to take. As we approached a rest area I told him I had to stop and piss. Well the rest area turned out to be a scenic overlook, so I got out and went behind the truck, whipped it out and did my thing. Well I got hard, I wanted to jack off so bad, but I couldn't, when I got back in my truck he asked me if I wanted to buy his watch. He needed some money for his trip, bells an lights went off in my head.
I told him I'd buy his watch, but I said there was something else he could do for me. I could see he was getting scared, I told him that I wasn't gay or anything but I'd like to jack him off. He didn't have to do anything for me but let me do it to him, well after a while he agreed to let me do it.
I went over to the passenger side, opened the door and he swung round. 'what if someone sees us', I assured him we'd be ok. So I slowly undid his belt and undid his button fly. I looked at him and told him this was my first time for doing anything like this. I got a smirk out of him, as I reached in and grabbed his pants and underwear I pulled them down to his knees, revealing his already hard penis. I reached under the seat and pulled out a jar of vaseline and started to coat his rock hard-on, I slowly started to stroke him and caressed his balls which had no hair. I asked him if he jacks off a lot, he said that he never jacked-off before. So I picked up the speed a litle bit, I could tell he was really enjoying it, moaning, groaning, hips bucking and thrusting, his breathing started to increase, and in no time he was cumming the biggest load I had ever seen. I continued to stroke him until he went soft. As he laid there on my seat I grabbed a rag and cleaned him up. I was so hard myself I opened up my jeans and started to jack off. Well he sat up in the seat and asked what I was doing, I explained that I was jacking myself off.
As I stood there with him watching me I kept on stroking, well to my surprise he reached down and grabbed my penis and started to stroke me. Well it didn't take long until I shot my load all over my truck, he looked at me and said that was really something, so we pulled our pants back up and got back on the road.
As we were getting near his drop off, he told me that he was a virgin and really was greatful for that little experiance.
As I stopped to let him out, I handed him twenty bucks and thanked him for letting me, he smiled and went on his way. I wish we could have spent more time together, there was so much more that I wanted to try, that was a trip that I will never forget.
Now older, I still haven't done everything yet but who knows some day is coming.