By: Unknown Author
Five years ago, I was still living at home and was still a virgin. My parents were having the house painted and papered and had hired a handyman to do the job. I recognized him as the dad of a guy in my school who was one grade behind me.
Bored and curious, I was watching him work and he entertained me by explaining how he was going to hang the paper and such. He asked me if I wanted to try hanging a piece of wallpaper and I readily agreed. He wet a strip of paper and told me to climb up the ladder so he could pass it to me. He stood on the bottom step and handed me the wet piece of wallpaper. As I leaned forward to place it on the wall near the ceiling I felt his hand on my ass, keeping me steady.
I was having trouble getting the paper aligned and he climbed a few more rungs of the ladder and reached over my shoulders to help me. I felt something strange and realized that his dick was pressing against my ass. I didn't know what to do, but I figured he wasn't doing it on purpose. He was my schoolmate's dad for god's sake!
The more he tried to help me with the paper, though, the more his dick pressed into me, and I couldn't believe it but I was getting a stiffy! Oh, I had had hard-ons before and I knew about jerkin off - a friend had told me about it three years before and I was always doing it. I have always been quite shy and didn't know what to do or say. My mom was in the next room, too. I don't think he knew I had a hard-on, but I just excused myself and left quickly, a bit embarrassed but really excited, too. I ran to the bathroom and jerked off!
After that day I pretty much stayed out of his way and let him do his work.
One day, when he arrived at the house he told my mother that he had forgotten to put his ladder in his truck and asked if we had one he could use for the day. My mom said we did and told me to unlock the shed for him and show him where the ladder was stored.
I unlocked the shed door and pulled on the handle, but it always stuck. He said he could help me with it and reached around me and grasped the handle. He gave a big yank and stumbled as the door came loose. When he tried to stop himself from tumbling backward, his hand grabbed at my front, wrapping around my thigh. As he got himself steadied he didn't remove his grasp on my leg and started rubbing his fingers against the edge of my cock and balls.
By the time I opened the door fully and stepped inside I was already hard. I guess he felt it grow or he just knew somehow, because as I reached up to switch on the pull chain light his arms encircled my waist and his hand immediately started massaging my hard dick through my pants.
I just froze, embarrassed, but I was really, really excited. I don't wear underwear, well rarely anyway, so as he unzipped the fly of my pants he had my hard, bare cock in his hands instantly. Although it felt good, this was all new to me and I was embarrassed and moved away.
As I was putting my dick back in my pants and adjusting myself, he told me it was ok and not to be embarrassed. He told me that since I didn't have a dad it was important for another man to teach me how to masturbate, that it was perfectly natural, and then he asked me if I wanted him to teach me.
Even though I knew how already I didn't tell him this, rather I nodded yes.
He got my dick out again and began to gently stroke it, and started talking dirty to me while he did it. I had never experienced dirty talk before but I loved it!
He came around in front of me and continued to stroke me and got his dick out, too. It was already hard and was a bit bigger than mine. It was the first time I had ever seen another man's cock.
After stroking both our cocks for a few minutes, he let go of both and pulled my pants down to my ankles. He moved behind me again and resumed his stroking of my cock. Suddenly I felt his hard cock rubbing up and down the crack of my ass. I knew about ass fucking but had never experienced it and wasn't sure I wanted to, or at least if I was ready to do that yet, and I became frightened of what he might try to do.
He started jacking me off faster and was squeezing my cock harder, and was hump-fucking my ass faster and harder, too. It felt really good and my cum started squirting out.
As I stood there catching my breath, I suddenly felt something warm and thick on my ass and knew that he had just cum, too. He took a painter's rag out of his back pocket and wiped his cum off my ass then reached around and, taking my cock in one hand, wiped the dripping head with the rag. We quickly adjusted our clothes and headed back to the house with the ladder.
He finished the work at our house over the next few days but nothing more happened, and to this day I have never seen him again.
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