Miss Information

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Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

I’ve been dating my girlfriend for about four months now. Everything is good, including the sex. She’s a little shy, but I’m having fun getting her to open up. I find her very attractive and there are quite a few good pictures of her on Facebook, which I often peruse while jerking off. My question is: do I tell her this (not in such a blunt way, of course), or would most girls just find this creepy? — Can’t Get Enough


Dear Can’t Get Enough,
If you hadn’t had sex yet I might say wait. But four months? Tell her. Why not? Technically, you’re supposed to be all open and honest and talk about sexual fantasies before you have sex, but that’s not how it usually works out. We’re lucky if we can get ourselves to discuss the big stuff, like sexually transmitted diseases and birth control. 
Are the particular pictures you’re choosing unusual in any way? Then tread lightly. A cheerleading uniform might represent insta-boner to you, but she might think that’s creepy. Ditto for the one where she’s arm-in-arm with her hot sister. There may be residual competition there or some sort of complex. Solo, more mainstream shots are the safer bet. 
You can be really casual about this. Tell her you love her pictures. The XYZ one in particular. Sometimes you look at it when you’re horny and in need of "artistic inspiration." "Visual aid" is also good because it sounds so high-school AV club. If she wants to hear more she’ll ask you. If she doesn’t, try a few more tacks: "What were you thinking when you took that picture?" "You look great in short skirts. . . I was looking at that one picture, with the kilt and the bagpipes."
You can also tie it to a recent sexual experience. It introduces the subject in a way that’s organic and non-threatening. "It was so hot the other night when we fucked in the bathroom at Jill and Allen’s dinner party. I was thinking about that at work and then I went on Facebook and saw that picture of you in the tight Zeppelin shirt and ripped nylons and got all riled up."
Still no response? Give it up. Not the masturbating. Just the talking about it. But I’d be really surprised if she isn’t overwhelmingly receptive. Your partner jerking off to you instead of random porn is supposed to be every repressed person’s dream. (Okay, I suppose there are some die-hard romantics out there who also share that sentiment.) Not saying your girlfriend’s repressed, but you did say she’s shy, and that’s in the ballpark. Personally, I think people with the "Only jerk off to me!" expectation are psycho. Sure, once in a while. But all the time? I’d be disappointed in my guy for being so un-creative. At least put me in a different costume or setting. Change the color of my hair. We all deserve a little fantasy in our lives, even if we’re not present to appreciate it.


Dear Miss Information,
I usually don’t come. Should I tell a man that before we have intercourse, so he doesn’t feel inadequate when I don’t finish? Or should I wait until we’re further into the relationship? It’s not that I never come. Once I had multiple orgasms. I’ve got toys, books, etc. What I really need is practice without pressure. Not Quite There

Dear Not Quite There,

Ah, orgasm purgatory. The longer you live and the more partners you’ve had, the greater the chances you’ve been at one (or both) ends. I used to date a guy who never came. Once, maybe twice, the whole time we were dating. We both worked freelance, so the opportunities were plenty. I kept holding out for that magical combination. Sober + lights on + empty stomach? Nope. Doggy style + partially clothed + his apartment + middle of the afternoon? Sorry, Bachelorette #2. No pop shots for you or Jimi Hendrix "Oh!" faces. You’re going home with that weird, incomplete feeling as well as a six-month supply of confusion and self-loathing. Thank you for playing!
While we’re all responsible for developing some baseline technique, orgasms can be complicated affairs. It takes different things to get people off and both people should be communicating. Even if that means a borderline unsexy line like, "Yeah, probably not going to happen, so don’t knock yourself out." Some might disagree, but sometimes being a slacker is more pleasurable and satisfying than turning a thirty-second genital contraction into a fruitless two-hour quest. Guys, girls, it makes no difference. Five percent of us are able to come quickly and easily for our entire adult lives. The rest of us go through phases.
There are better ways to say it. I think it’s good to get it out of the way before you get too far into the act. Something like, "Just so you know, I probably won’t come. It usually doesn’t happen until I’ve gotten to know a person really well and we’ve had sex a bunch of times. For now, I just want to fuck your lights out. [Substitute "make love" if the mood is more sweet, "make whoopee" if you’re a Newlywed Game contestant.] I’ll tell you if I’m not having a good time. We can talk about long-term strategies later. Okay? Break!"
And by all means, make good on your claims. If you want it to last longer, tell him. If you’re ready for him to pull the trigger, start issuing some visual and physical cues (or better yet, foul-mouthed commands). Is he slacking off on oral and you want a little more? Tell him!
Hopefully your partner’s not one of those hard-headed goal-obsessed types on a mission to make you clutch the sheets and roll your eyes back. The more he relaxes, the more you’ll relax, and the more likely it is to happen the next time you get frisky. If not, there’s always the Orgasm Diet, the staples of which are bacon, chocolate, a few non-taxing crotch exercises and cheese. Not too shabby.
Attention all international readers and worldwide travelers: Miss Info has a lovely reader who’s staying in a remote area (a small town in South Korea, to be more exact) and finding it difficult to meet young men and get laid. Unfortunately, my passport has less ink than a bank teller’s pen. Any border-crossing pickup tips? Leave ’em in the Feedback Section.

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