20 Of The Craziest Babysitting Stories Of All Time.

One time, when i was 12, i caught my babysitter, who was probably 17 at the time, smoking a joint. I had no idea it was pot, i just thought it was a funny looking cigarette. Anyway, she told me not to tell my mom, but i just stared at her blankly. Then she got really red in the face and nervously said "If you promise not to tell anyone, I'll let you see my boobs." I got all excited and embarrassed and bashfully agreed. I've told many of my friends throughout the years, so i ended up breaking the promise.


Was babysitting this little girl who had issues sleeping when her parents weren't in the house. Parents told me she could sleep in their room to comfort her. Child discovers GIANT dildo, and gives it to the basset hound thinking it's a chew toy. Have to chase down basset hound to retrieve vibrating giant dildo. Don't know what to do with dildo. Place dildo on child's parent's dresser. Tell child to never speak of this night again. I was babysitting my cousin.