1. 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 ...
    seeing my stiff little dick. I had to go so bad I forgot to notice I was only in my underwear. Somehow my pj bottoms were missing. I was in such a fog I just finished up and snuggled right back in with her and as I drifted back off, I noticed her hands were hidden under the blanket and her eyes were closed, but I didn't think she was sl**ping. A few times she watched me, my mom stayed out so late, Heather would stay the night, but I never knew what time my mom came home, and I would wake up in the morning with me and Heather curled up on the couch together. I really liked cuddling with her, and she told me I was her little boyfriend. I hugged her whenever she came over and before she left, my head resting against her belly. One night we were.really bored, and shortly after my mom left she asked if we could do something cool and secret and I had to promise to keep it a secret. Of course I always agreed to do whatever she wanted, especially when I thought she was going to let me do something grown up. We went to the &#034adult drinks&#034 cabinet, and she somehow got the lock open with a bent paper clip. She took out a bottle she thought looked good, poured some of the contents into a tumbler with some ice, and mixed in some apple juice. We passed the cup back and forth a few times. It tasted fine, and soon my stomach felt warm and I felt good all over. I felt like I was in a really good mood, and we were laughing and giggling at eachother. We took the drink back to the couch and ...
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