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May 18, 2008. #2. I have done it with friends and family. When my cousin was 14, he asked me (17 at the time) to show him how to do jack off. Loved his reaction when I pulled it out: "Holy Fuck, I would hate to see you hard!" Didn't take me long after that. Soon as I got into it, he pulled out his smaller pecker and began to join me.

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