My favorite sitter.
Date: 1/8/2018, Categories: First Time, Masturbation, Taboo, Author: badboy4320, Source: xHamster
When I was quite young, my Mom wouldn't leave me at home without a sitter. She got this young college girl from the neighborhood to stay with me on weekend nights so she could go out partying with her friends. I thought I was a big boy and could stay by myself, but she wouldn't have any of it. Anyway the girl watching me was named Heather. She didn't really look like an adult but Mom trusted her because she was really mature and trustworthy. We usually got pizza delivered, watched tv, and I usually fell asl**p on the couch with her next to me, and wouldn't remember anything until, she woke me up to hustle me off to bed shortly before my mom returned home. One night she walked in, plopped her school books on the floor and said hi to me. After my mom left, she told me that since I was so good for her, I could stay up and watch tv as late as I wanted, as long as I didn't tell my mom, and I went to bed before she got home without a fuss. Of course I agreed, feeling grown up, and felt like she was conspiratorially sharing a secret with me. She told me she was bored late at night because I fell asl**p so easily, and wanted me to stay up with her. But, baby boy falls asl**p so so easily. That first night she let me stay up late, we cuddled on the couch under a blanket and maybe a half hour later I was dead asl**p. I don't know how much later it was when I woke up but I had a really painful pee pee hardon. I slipped out from under the blanket to go pee and tried to keep her from ...