September 12, 2012 

I want to buy my 14-year-old niece a dildo, some lube, and an age-appropriate book about sex. (Can you recommend one?) I have her mother’s permission, but I wanted to double-check on whether there are legal issues I should be concerned about. (I live in Oregon.) Do you think it would be inappropriate for me to cross that boundary with my niece? I figure it would be less awkward to get these items from me than from her mother, and I would include a thoughtful letter on love, sex, and life with the promise that I will never bring the “gift” up, but that I will always be happy to talk if she wants to. Any other advice on how to handle it appropriately would be appreciated.
Wanted Toys Too

P.S. I am motivated to do this due to my own teenage experience of not wanting a penis to be the first thing of substance put in my vagina. I had to resort to a plastic banana, no lube. Ouch!

“Your niece is lucky to have a mom and an aunt who are invested in her sexual well-being,” says Jennifer Pritchett, the owner of Minneapolis sex-toy shop Smitten Kitten, and a frequent Savage Love guest expert. “She’s also lucky to live in a time when sexual health information geared toward young adults is readily available.”

And why shouldn’t penetration toys be readily available to your niece? All any 14-year-old boy who wants to experiment with penetration—for his own pleasure, to build up his confidence in advance of partnered sex—has to do is make a fist. Girls who are curious about penetration shouldn’t have to resort to plastic bananas.

Pritchett recommends that you get your niece a copy of Heather Corinna’s book S.E.X.: The All-You-Need-to-Know Progressive Sexuality Guide To Get You Through High School And College, which is terrific, and that you make sure your niece knows about scarleteen.com, an amazing, comprehensive, and sex-positive independent sex-ed website.

“Share these resources with her,” says Pritchett, “but do not write an awkward letter! All you are going to do is communicate your own insecurities about the ‘gift,’ and trust me, she’s got enough weird cultural hang-ups about sex and pleasure to deal with! It’s admirable that you want to save her from the plastic banana, but be careful not to inadvertently project your own sexual choices onto her experience.”

Pritchett also suggests that instead of selecting a sex toy for your niece, WTT, you take your niece to a sex-toy shop so she can make her own selection—because, hey, what could be awkward about that? “If you really want to empower her to make her own decisions about her body,” says Pritchett, “take her to an education-based shop like She Bop (sheboptheshop.com) in Portland where their trained sex educators can help her figure out what she might like to try.”

If your niece would like to go sex-toy shopping with you—and that’s a big if—you’ll need to call She Bop in advance and make an after-hours appointment. “We are an 18-plus shop,” says Jeneen Doumitt, co-owner of She Bop, “but we have made special arrangements in the past for younger teens. We would need to get written consent from the legal parent or guardian, and the parent or guardian would have to accompany them.”

There is also the option of going on their website and shopping together with your niece, or you could send your niece to any number of female-sex-positive websites and she can pick the toys she wants you to buy—no letter from parent or guardian required, no embarrassing small talk.

Sorry, DFF, but you’re just gonna have to move to a big city (or travel to one) to realize your dreams of sweaty, smelly, stinky female feet. And if your dreams revolve around servicing the feet of more than one loving, indulgent woman, then you’re gonna have to pay nice ladies to make your dreams come true. Approaching strange women in hick towns or big cities and asking them to indulge your fetish isn’t going to get you anywhere other than a sex-offender registry.

During an extremely long (four-year) dry spell of my own, AMU, I responded more than once to offline offers of blowjobs from girls. I was horny, I was desperate, and my powers of concentration were such that I could close my eyes and pretend—and I’m really dating myself here—that Bo Duke was blowing me.

Desperate men do desperate things, AMU, and just as my teenage/closeted desperation drove me into the arms, beds, and mouths of some nice young women, similarly desperate straight guys have been known to accept blowjobs from gay or bi dudes. And just as the concentrate-on-Bo-Duke blowjobs I got from girls back in the ’80s didn’t make me straight, the concentrate-on-Sofia Vergara blowjobs straight guys get from dudes today don’t make them gay.

It’s possible, of course, that your husband will wind up getting rest-stop blowjobs one day—anything is possible—but that one time he almost got a blowjob from another dude doesn’t make rest-stop blowjobs any more or less likely. (I’m assuming your husband is telling the truth about not going through with it.) And as your being turned on by the thought of the husband getting a blowjob from another man doesn’t make those rest-stop blowjobs any likelier either, AMU, I think you should go ahead and let yourself be turned on by the idea.

There are limits to being GGG—self-harm being one of them. Give him permission to explore this particular fetish with someone stupid enough to smoke. If he pouts, CIGGG, remind him who inhales his dick.