Cat-sitting

When I was in high school, my main source of income was cat-sitting for people who lived in my neighborhood. There were a number of different families I would do this for, and for the most part there wasn’t anything out of the ordinary, but for one particular family, my cat-sitting also featured some colorful extracurriculars.

This family was about as average as you could get: middle-class, a wife and husband, and two kids: a son and a daughter.

I knew this family well, due to neighborhood functions and whatnot. The daughter was a couple years older than me, and she was very attractive. I wanted to make a move on her, but never did due to the age difference (she was in college, I was not) and my ineptitude with girls.

When I would go and cat-sit for this family, I would do the normal duties I was asked of, and I would then go upstairs to the daughter’s room. I would get into her wardrobe, and jerk myself off into the sexiest things she had in there. This included dresses, skirts, bathing suits, bras, and panties. I would picture myself actually having sex with her while I did it. It was the closest thing I could get to that feat.

I’m not sure when I started, but I did this ritual for years. There was a point where I would go over twice a day to jerk off into the daughter’s clothing. Gradually, I did my thing less and less, until I eventually stopped altogether when I was in college. I also got much more paranoid as the years went on, making sure to clean whatever I jerked off with, even if the daughter wouldn’t be home for months.

I never got caught. I still talk to the family when I visit my parents.