I will not lie. I am writing you on a dare, but this is a real dilemma for me. You recently wrote in your column that if you don’t enjoy masturbation, you aren’t doing it right. I am not good at masturbation. I grew up in a conservative Catholic family and was taught that it is bad to touch yourself. I have grown up now and know that I won’t go to hell for playing with myself, but I am still kind of uncomfortable doing it. This is where the story gets a little funny. My boyfriend likes to masturbate together. He finds it very exciting to watch me play with myself while he does the same. I really can’t relax under the pressure, and feel awkward when he is watching. I would prefer if I could play with his stuff, and he could take care of mine. Do you have any recommendations for learning how to masturbate better or get over feeling awkward in front of my boyfriend? I asked a friend, and she offered to show me some of her techniques, but that freaks me out. She laughed and then said I should write you. So Dear Uncle Mat, besides dragging my washing machine into the bedroom, how does a girl learn how to be a better masturbator — with an audience?
— An Awkward Girl
P.S. My friend knows you and is dying to hear you answer this one!
Dear Awkward Girl,
I can’t even imagine which of my friends would offer to show you how to diddle yourself and then refer you to me. It is no secret that my knowledge of the ladies and their fancy parts is next to nothing, which is why, I suppose, any of my female friends might find this discussion amusing.
Reading is an excellent way to expand your knowledge. I didn’t read any books for this column, because I am happy with there being a few mysteries left in my world. I did, however, do a little googling and Amazon-searching and found several titles that looked helpful. I hesitate to recommend a book, since I couldn’t really tell you if the information is helpful, but I did notice that there were two types of books: the more practical how-to manuals, and the more intellectual I-love-my-little-flower-but-there-is-a-history-of-repression-related-to-this kind of books.
I think both might be useful for you. You may have grown up and rationalized the hell out of the relationship between your left hand and your clitoris, but that awkward feeling is probably related to guilt. If you’re comfortable playing with and having sex with your boyfriend, this shouldn’t be that different. What are you thinking about when you are together and masturbating? Why is it different? I suspect there is still a little nun whispering in your ear about whatever happens to naughty girls.
Do you enjoy masturbating alone? Practice does make perfect. Just keep at it, and eventually you should find something you like. Remember that it isn’t a job. Yes, there is a nice reward at the end, but good masturbation is not about where you are going but how you get there. That is the cheesiest thing I have ever written, but it is true. As you gain some confidence, you should relax more and hopefully find it easier to share.
Talk to your boyfriend about the situation, too. Maybe you could work up to it together. You could ask him to play with you and help you pleasure yourself and ease into the situation. If you’re lucky, he knows a few tricks of his own. Just don’t ask where he learned them. Once you’re on a roll and relaxed, he can kick back and enjoy the show. On the other hand, if you find it truly uncomfortable, he should be willing to work out some sort of compromise. It is great to be open to pleasing your partner and sharing a strong sexual bond, but pretending or forcing your way through something you find unsatisfying or embarrassing will only breed resentment in your relationship. And the beauty of masturbation is that it shouldn’t be breeding anything! OK, that was even cheesier.
Much love and good times in the party box,
Your Uncle Mat
Uncle Mat answers questions about relationships, sex, pets, and art. Email him at
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