I started babysitting a kid who lived a few houses down from me. We never really knew each other or talked since he went to a different school but I walked down the street one day and his mom said she needed a babysitter. He was 14 years old and she was quite a protective mom, which is why he still needed a babysitter.
She said that her and her husband would be gone for the weekend and I would need to stay at their house for the whole time. I was fine with this as they are quite wealthy and I was getting paid well, plus all I had to do was play video games and watch movies with him.
The weekend started off well and we played some games and stuff and were both laying on couches later while watching a movie. I glanced over at him and noticed he had quite a large boner pointing up in his basketball shorts.
Now being a horny teen, this turned me on and gave me a boner. I just readjusted myself to hide it but kept taking sneaky looks at his boner figuring he didn't even notice he had one. I was curious at this point as to if he jerked off yet (at this time I was doing it at least once a day) and was really wanting to ask him but was nervous since I was his babysitter.
He was very fit and attractive (not super built or a football star but good looking) and I am also not gay, just curious. I noticed that he looked down at his boner then quickly sat up and I pretended that I didn't see. He said he had to ask me a question and I said sure excitedly. He asked me why this is happening to him and I replied by saying it's normal and briefly told him about puberty and sex and masturbation.
I asked if he would like to lean how to jerk off and do it now and yes said sure.
I was very excited at this point both to see his dick and to jerk off with him. I told him that he would have to pull down his shorts and if he wanted to his shirt too. He hesitantly agreed and I did the same removing all my clothes. I was happy to see him fully nude with his hard dick pointing straight out with a small amount of pubes around his dick and his big loose hanging balls. I then told him to stroke his dick like me but and I then reached over to help him, putting my hand on his dick that was almost bigger than mine and started stroking it.
He then took his hand and put it on my dick which felt so amazing to have someone's warm hand on my very hard penis. I told him to stroke faster and he did until I came shooting many ropes of cum onto his hand and the rest of us. I told him to keep going then I came again a few minutes later.
I started stroking him again and made him cum. We did a few more things that shouldn't be shared here....
He also convinced his mom to let me babysit him more, which led to more of these sessions.