Several years ago I finally moved out of my parents house. I decided to leave everything behind. My cell phone, my car, my electronics, everything that I didn't own. I wanted complete independence. My plan was to find ways of travel to as far as I could go, and then find a job and and eventually go to school. Looking back, it was stupid. The first couple of years I was homeless and was lucky to be working, but that's beside the point.
I was somewhere in Colorado. I had managed to hitchhike my way all the way from Florida. Most of the time I got picked up by bored or lonely truck drivers, who just wanted someone to talk to. One time the guy had me drive for a few hours. While in Colorado I was walking along the road, putting my thumbs up for anyone that passed. Eventually, a large semi-truck pulled over. He asked where I was going, I told him as far as he would take me. I hopped in and he began to drive off.
The first couple of hours went by as pretty much the norm. He asked about me, we talked about his truck, just pointless talk. Eventually he pulled into a truck stop so we could use the restroom.
I walked up to the urinal and he took the spot directly next to me. Now, this wasn't a very high class restroom, so it has one of those long multi person urinals. Anyway, I noticed he was staring directly at my dick. He had a very obvious hard on and was not trying to hide it.
This was the first time anything like this had happened to me. My parents were very strict, so the ideas of abstinence were pretty much fried into my brain. I did my best to avoid any sexual activity, let alone that with a male.
Yet, the whole situation had me very aroused, and I began to grow hard. I must have been standing there 10 minutes, just looking at his dick and he looking at mine. When I realized just how we were standing there, I very quickly (and painfully) put my boner back into my pants.
I limped awkwardly back to his truck. A few seconds later he was starting the engine and pulling out of the parking lot.
For the next few hours, our conversation had a very sexual undertone. He talked about his past sexual experiences, I mostly listened. He eventually asked about mine, and I confessed. He asked if I had ever even masturbated, and I told him I had not. I had tried, but felt very guilty as soon as I started.
The hours of conversation had aroused me; my dick was in pain from the length of time it was trapped in my pants. I had never had an erection this long. He must have noticed my discomfort, because he told me I could unzip my pants and let it out. He told me he didn't mind, and he probably would too.
I did exactly that. It was a pretty thrilling experience. I heard his pants unzipping and I looked over and saw his monster of a dick standing straight up. I felt mine twitch. I was confused but excited at the same time.
We then talked about masturbation for some time. I asked him some questions: how to do it, how often does he, etc. Finally, he said he could show me. Without even thinking of what I was saying, I said yes. This was going against everything I had been raised to believe... but I was leaving my life behind me, so I didn't care anymore.
He pulled over to a rest stop. I was worried about all of the people, but he assured me the truck was private. In fact, he told me most truckers usually jerk off in their free time. I felt reassured so I followed him to the back of the cab.
He told me to get more comfortable, so I removed my jeans and shirt. I was going to leave my underwear on, but he grabbed them and pulled them down. He too undressed and sat next to me on his cot.
He placed his hand on his dick and began to stroke it. He told me to try. I tried it on myself, but it hurt and did not feel good. When I told him this, he told me it was probably because I was cut. He placed his mouth just above my dick and spit. Just the cool spit alone felt amazing. He told me to try again. I slowly stroked my shaft. It felt better, but not as amazing as I had hoped. When I told him this, he said I might be doing something wrong.
He told me to try it on him. I really wanted to, but I just couldn't bring myself to do it. He understood, and said he would help me out first, to show me how good it felt.
He placed his hand around my dick and began to stroke. Instantly, a burst of pleasure went over me. I bit my lip and tried to hold back my moan. It didn't work as I nearly screamed. He chuckled and pumped faster.
I don't think I lasted long, but before long, I was experiencing my first orgasm. Ropes of cum burst out of my dick as I collapsed backwards.
I laid panting for what seemed like ages. The next thing I knew, it was morning. I could hear the sounds of the road so I knew he was driving. I was still naked, but I was clean and a blanket was over me.
I dressed and walked up front. I sat down. He smiled at me and asked if I slept good. I smiled back, but didn't answer.
We drove in silence for some time. I felt slightly guilty for what I did the night before, but for some reason, I felt worst for not returning the favor. When I couldn't stand it anymore, I placed my hand on his leg.
Without a word from either of us, I found my way to his button and undid it. I unzipped him and he leaned his butt up so I could push his trousers down. He was going commando, so right away his dick popped up. It wasn't completely hard, but I grabbed it and began to rub it. I stroked it up and down, just like he had me. I don't know if I was good, but he grunted and thrust his hips, all while driving. He eventually told me to grab a shirt from the backseat, the first words in a long time, before he blew his load all over the shirt.
He thanked me, and I pulled his pants back up. The rest of that day was followed by silence and radio. It wasn't awkward silence, just content. That night we shared the cot. It wasn't planned, but we both ended up naked. After another very powerful orgasm, I passed out. I woke up in his arms, still naked.
I had planned to only ride with him for however long it took to get as West as I could. I stayed with him for three weeks. We eventually progressed from more than just masturbation, but for the sake of this site, I will not share any of that. I spent those three weeks going from state to state, east to west, north to south, but eventually, I learned he had to return home. He worked three weeks on, four weeks off, then four weeks on, three weeks off. He told me he was actually married, unhappily, but married none the less.
I was slightly hurt, but I wasn't in love. I understood, and continued with my original plan. He wrote down his phone number, and told me to call if I was ever in Kentucky. We left after one last session. He dropped me off in Indiana, where I would end up living permanently. As I said, I was homeless for about two years. Well, I shouldn't say homeless, because I was indoors, just sleeping on sofas and homeless shelter cots for sometime.
Eventually I found a great job and could afford a home. After a while, I could afford to buy a cell phone. Although, it was a big ol' brick I wasn't complaining. Next came the car.
After all those years, I still had his number. I don't know why I didn't throw it away right away. Eventually the original scrap got too wrinkled, so I copied it onto a new piece of paper. After that paper grew trashy, I wrote it on another. After that, I just remembered it.
I should say, at this point in time, I grew interested in women. I was blessed with fortunate looks, so getting them was not much of a problem. I don't know why, but I have always had the best orgasms from hand jobs. Sex, blow jobs, anything... it was all great, but nothing compared than a good hand job. The only problem is, women don't know how to give a good hand job! One night, after growing sexually frustrated with my girlfriend of the time (among other things), I stormed out. We had been having sex, when she refused to continue because I didn't cum. I tried to explain to her I was different than most other guys. I told her all I needed to be happy was a good hand job. She tried to do it, but it was painful and not worth the effort.
Anyway, it was eight pm. I got into my car and began to drive towards Kentucky. I lived right on the border, so it wasn't a long drive. I was not driving to meet him, but before an hour had passed, I realized I was in his town. It was one of those spur of the moment things, when I decided to call him. He could have moved, or could be on a work period, or might not even have remembered me, but I called anyway.
It rang several times. I figured it was about to go to voicemail when a male voice answered. I said his name. When he confirmed it, I nearly freaked out. I told him who was calling. After a long silence, he asked where I was. When I told him I was in his town, he asked if I could meet him at his house.
He gave me directions and I drove to his home. His truck was in his driveway, extending into the street. I grew nostalgic just being near it. I knocked on his door and he answered almost instantly, as if he had been waiting behind the door.
We talked for sometime. I learned he had divorced his wife soon after he returned from our few weeks together. He had hoped I would call, but I never did. I explained my past couple of years. Eventually the discussion found its way to sex. I told him pretty much every detail of my sex life since we last saw each other. My first time having sex with a woman, all the way up to that evening, when I was having some trouble.
When I mentioned the hand job thing, he agreed with me. He too said he felt a woman could never give a decent hand job.
In years past, he would have been more indirect and subtle, but I guess he could sense my experience and readiness. He simply asked me if I wanted to have some fun.
I agreed and placed my hand on his leg. I rubbed his thigh for a few moments before I felt his hard on. I pulled down his shorts and began to stroke his dick. I rubbed my thumb on the bottom of his head. He groaned and thrust his hips. I could tell he had not had anything like this for a while. He eventually began to thrust his hips furiously, so I pumped harder and harder. He roared and shot his load all over the carpet in front of him. He panted for just a few seconds before he had my dick in his hands. Finally for the first time in years, I was getting a great hand job. Almost instantly, I came all over his hand. The orgasm was insanely powerful.
The next morning, I woke up sleeping on his couch. He told me he didn't want to wake me. He laughed and told me it was just like old times. I told him I hadn't passed out after any orgasm since our first few times in the truck.
I learned he was on his last week before he had to go trucking again. I called in for my vacation time that week, and spent most of it 'catching up'. When his time came to leave, he asked me to come with him. I had to decline, because I needed to work.
He understood and left on good terms, with plans to meet up after he returned. However, I reconciled with my girlfriend shortly after I returned, so I was not able to meet up with him, as I loved my girlfriend and did not want to be unfaithful.
Things eventually did not work out (for good this time) and we went our separate ways. Just like before, a free man, I drove to Kentucky. When I knocked on his door, he answered with a hearty smile. Recently, I was able to find a part time job in Kentucky that allowed me to take time off. How much time? Three to four weeks at a time.