I have never masturbated with another guy before, and truthfully, I don't even masturbate by myself a whole lot – once a week at most. Is it okay to ask him to masturbate with me? I have read all the JackinQ&A's on masturbating with others, and they have all been about younger guys asking older guys, not vice-versa.
- age 17, Alabama
I don't think it's a good idea to ask him. You're a little too much older than him for the two of you to be considered equal peers – you're definitely the "older brother" – and while you may not mean to abuse your position, he might not feel comfortable with saying no. In that case, it would be a mild form of sexual abuse.
I don't mean to scare you. It's just that for the good of both of you, it's probably better either to let him lead, or to let nothing happen at all.