This is an absolutely 100% true personal account of one day when I was 16
Today I'm happily married, but twenty-seven years ago, I was 16 living in western Pennsylvania outside of Pittsburgh. In June of 1976 two friends and I hitchhiked to Atlantic City, NJ to work on the boardwalk and enjoy the summer. We stayed at a friend's aunt's home and took a bus to work everyday at a hotdog stand on the boardwalk. After a month, one friend went home. A couple weeks later my other friend was picked up by his parents and went to Rhode Island to vacation. I was left on my own.
This is where the story begins. Mid August, I was out of money and had to hitchhike back to Pittsburgh (about 300 miles) plus school started back after Labor Day. I spent the day at the beach and around 6:00, I packed up and got on the road. The first ride uneventfully took me to Pleasantville. Around 8:00, I got picked up by a 25 year old guy who was a salesman and was going to Pittsburgh. Outside of Philadelphia, he said that he was going to crash for the night and that I could stay with him and he'd buy breakfast. It was getting dark so I figured I might as well since it was my ride all the way. He got a motel room. We went in and both took showers.
I started to fall asleep on the chair watching TV and he was in the bed. I had briefs and a t-shirt on. He had a robe on. He said he was turning off TV and it would be OK if I slept in the bed. So I got in and fell asleep on my side. About an hour or so went by and I felt his hand on my cock, just holding it. I pretended I was asleep. I was also freaked out, but I got hard. I could also feel him getting hard and pressing against my lower back. Then he began to slowly stroke me. To this day, I have no idea why, but I started to pump back against his cock. He started to whisper things like, 'do you mind this?' and 'you feel so good' (I only have a 5 1/2 cut cock and he was about the same size). I didn't answer him. Then he started to kiss the back of my neck. I rolled over on my back. He kept slowly jacking me off. Then he blew my mind and kissed me on the lips and Frenched me. I put my hand on his cock and he pumped my hand. While we were kissing the first kiss, I came. Then he firmly squeezed and milked my cum. After he replaced my hand with his, on his cock, he jacked off with fast strokes. He was on his side and I turned on my side facing him and kissing. After about three minutes I could feel him coming on my abdomen. He got up, got a towel, came back and cleaned us both off. He kissed me softly on the lips and said thank you. We fell asleep with our backs to each other. In the morning, I woke up with his hand around my already hard cock. Then he kissed me again on the neck and lay on top of me. It was unbelievable to slowly grind our bodies and cocks together. We held each other and pumped our bodies together. Then he got up and straddled my body so our two cocks were touching. He took them and started jacking them off together. Then he just jacked mine and I reached down and started jacking him. Then he asked me if he could suck me. I said, 'yes'. He started to suck me and it was the most incredible feeling. I started to moan and ready to come. He took it out and masturbated me holding it tight and stroking it fast. I came all over his chin. I came forever. He leaned down and kissed me again and I could feel my come as our faces touched. He said, 'Let's take a shower.' We went in and he was still hard. I was soft. We got in the shower together and turned on the water. Then he asked me if I would pee on his cock. I did after trying for what seemed forever, while he jacked off. Watching him I got a semi hard on but couldn't get completely hard. As I peed on him, he kept masturbating and them came. We washed our bodies. He asked me if I ever did anything like this. I said, 'no'. He asked me if I would like to suck him to see what it was like. I did, and was surprised how I enjoyed it. He was only semi hard. After about 10 times, we got out and got dressed went to breakfast and drove the 4 hours to Pittsburgh. On the way I was quiet and felt guilty. I was never even with a girl except for heavy kissing and didn't want to think I was gay, but I liked what we did. About halfway, he asked me if I would like to stop and jack each other off. I said, 'no', but was torn between the guilt and the pleasure. Finally he dropped me off about 15 miles from my house.
A guy that was about 40-45 years old picked me up. He was talking and after about 10 minutes asks me if I masturbate. I said, 'yes' (I think I did at least once a day back then). He asked me if I ever masturbated with a man. I said, 'no'. Then he asked what would I do if a guy touched my cock. I told him something like, I don't know. Then he reached over and put his hand on my leg and asked if I would like to see his. I don't know why, but I said, 'sure'. He kept driving, undid his belt and zipper and pulled his cock out. It was hard and probably about 6 inches. I started to get hard looking at him and my mind was racing wondering if I was gay because I got excited and thought about sucking him. He asked me if he could watch me masturbate myself and I said, 'Only if you do and pull over'. So we drove about 5 more miles before he got off an exit and pulled off the road on the edge of a wooded area. He put his seat back and started jacking off and said to me, 'let me watch you masturbate'. I pulled my cock out and started stroking, watching him. His cock was dripping with pre cum. Out of the blue sky, I leaned over and started sucking him. I kept jacking myself off and he kept jacking himself of in my mouth. Finally he took his hand away and I kept sucking it and jacking myself off and then I stopped jacking off and cupped his balls and jacking the base of his cock. He put his hand on my head and started to pump my mouth telling me how good it feels and how his wife didn't suck him that well. He said he was going to come and I took it out and jacked him off until he came. It went all over his shirt. Then I went back to jacking my self off. He watched and I thought he would suck me, but all he did was kiss the head of my cock. I came within a minute after he did that. He gave me Kleenex's. Then he drove me to the street I lived. He asked me for my phone number, but I gave him a fake one.
That was an unbelievable day, although for about two years I was paranoid that I would become gay until I slept with my first female. But that day still serves as a masturbation fantasy for me.