I'm 16 and I like my friend's mom who is 35. Of course she's married and she has two kids. But I really like her. What should I do?

Help One Really Needy Youth

My response after the jump...


Here's what you shouldn't do: you shouldn't say anything—not to your friend, not to his mother—and you shouldn't try anything.

Here's what you should do: you should masturbate about this woman as much as you like—taking care to vary your routine (left hand, right hand, a little lube, a lot of lube, a firm grip, a light touch, etc.)—and you should take my advice for horny fifteen year old boys:

Worry less about getting your 15-year-old self laid, and start thinking about getting your 18- or 20-year-old self laid. Join a gym and build yourself a body that girls will find irresistible; read a lot so you'll have something to say to the girls you do attract; and get out of the house and do shit—political shit, social shit, low-stakes shit—so that you'll meet different kinds of girls in different kinds of settings and you'll get comfortable talking to them. More assignments: Get a decent haircut and use deodorant and floss your teeth and take regular showers and wear clean clothes. Go online and learn about birth control and STDs, and learn enough about the clitoris that you'll be able to find it in the dark. Masturbate in moderation—no more than 10 times a day—and vary your routine. I can't emphasize this last point enough. A vagina does not feel exactly like a clenched fist—nor does a mouth, an anus, tit-fucking, or humping. If you don't want to be sending me another pathetic letter in a few years, you'll vary your routine now so that you'll be able to respond to different kinds, levels, and intensities of sexual stimulation when you do become sexually active.

Yes, yes: I know. You're not 15. You are 16 going on 17. Well, I've given pretty much the exact same advice to sixteen-year-old gay boys:

Worry less about getting your 16-year-old self laid and more about getting your 20-year-old self laid. Get out of the house and do shit, get books and read shit, volunteer for a political organization and change shit. You’ll have more boys to choose from in a few years and you’ll be a more interesting, more informed, more attractive guy, thanks to all that doing, reading, and volunteering. Beat off in the interim, WASTED, remembering to vary your masturbatory routine (left hand, right hand; firm grip, soft touch; with toys, without; lots of lube, just a drop; etc.), and try to cultivate your own erotic imagination. (Translation: Don’t jerk off to Internet porn exclusively; use your imagination once in a while.)

Lots of boys your age have crushes on their friends' mothers, on their neighbors, on their teachers, HORNY, and lots of boys who were your age once had those kinds of crushes. It's a great fantasy, HORNY, and its given us entire porn genres. But the potential benefits—a few orgasms for you and maybe one for your mom's friend (if you're any good at this sex stuff (and, at 16, you most certainly are not any good at this sex stuff (yet! you will be one day!)))—aren't worth the potential blowback. A destroyed friendship, a broken family, and, depending on age-of-consent laws where you live, a prison term for your friend's mom—those are high prices to pay for a few lousy orgasms. And that's assuming your friend's mom is even interested, which she almost certainly is not.

Beat off about her, HORNY, to your part's consent. Then go do shit, go read shit, and go volunteer somewhere and change shit. You'll meet girls, some closer to your own age, and you'll be a more interesting, fuckable dude for all that doing, reading, and changing. Good luck.