I know it is an odd title, but my bicycle actually played a role in my early masturbation experiences. Read on!
When I was young, I won a Raleigh bicycle in a raffle. I was very proud of that bike, and took extreme care of it. I even used to re-grease the wheel bearings every couple of months; something that wasn't needed but I did it anyway. I didn't have real bearing grease, so I used Vaseline, which worked well.
One time when I was 13 I was working on my bike in the garage on a warm summer day. When I got to the wheel bearing part, I was kneeling on the floor with my hands all greased up with Vaseline. My penis was kinda scrunched up in my crotch, so I wanted to re-arrange a bit. I couldn't do it through my shorts because I would have gotten them all greasy, so I reached in through one of my leg openings and under my boxers to pull my penis to the side. I noticed that my slippery fingers felt really good on my penis, and, like any 13 year old boy, I began to get hard immediately.
Well, that felt even better, so I kept rubbing the head of my penis with my slick fingers, and could tell I was going to need to carry this further. I didn't want to do it in the front of the garage for fear of someone coming, so I got up and went to the back of the garage and hid behind a pile of boxes. There I undid my shorts and pulled my boxers down around my thighs, and jacked off with the Vaseline. That was the first time I'd ever used lube, and boy, did it feel great. Pretty soon I was spurting on the floor in an excellent, mind blowing, orgasm.
Just then I heard someone call my name. It was my best friend, Billy. He had come into the garage to look for me. Before I could pull my pants back up, there he was, standing in front of me with a very surprised look on his face. I was standing there with my shorts around my thighs, hard penis in hand, and blobs of semen on the floor. Pretty obvious what I had been doing.
Billy just laughed, and said something like, 'looks like you're having a good time!'
I couldn't say anything, I was too embarrassed. Now you need to know that I had fanticised about masturbating with Billy for probably two years. Though we were inseparable, we never did anything sexual together, and I wondered if he masturbated at all. Thoughts of him pleasuring himself were high on my list of masturbation fantasies, and here I was, caught in the act by him!
I was really surprised at what happened next. He asked what I had on my hands, and I told him, and he asked if he could try it! Of course I said yes, and he went to get my jar of Vaseline from the front of the garage, came back to where I was, and slipped his shorts down. He greased up, and went to it.
Like me, he was circumcised, and though had hit puberty, only had a few wisps of pubic hair. He looked to be about the same size as me. Though I had sneaked peeks at him while showering in gym class, I'd never really had a chance to see him naked, and never with a hard on.
I stood transfixed as he gave his penis a workout, and watched as he tensed and shot on the floor like I had. It turned me on so much to watch him that I had gotten hard again, and was jacking off again, and I shot for the second time just after he did.
We both had a good laugh over that, then cleaned up and went about our business.
The next day Billy showed up at my door, and I let him in. After a minute he asked if I had any more Vaseline left. I knew what he was getting at, so I said 'sure,' and we went up to my room. Pretty soon we were laying on the bed side by side jacking off with Vaseline. That became a nearly daily habit. When school started again he'd stop over at my house on the way home and we'd have a quick jack in my room. Eventually we started to do it to each other, and I really loved that. We did that all the way through middle school and high school, until we split up after graduation. I went to a different school than he did, but when we were home for holidays we always tried to get together for a jacking session.