Miss Information

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

Dear Miss Information,
    I am a forty-something guy in a relationship. It’s been a few months, and I’m happy. However, I keep browsing Craigslist’s “Casual Encounters” section. I’ve never contacted anyone, and I don’t intend to. What’s behind my fascination? Is this going to lead somewhere bad? — Slave to Craig


Dear Slave to Craig,
    There are more theories here than a quantum-physics convention. They’re listed below, along with degree of threat to your relationship. “1” is no threat. “5” means "recover any family heirlooms and delete all nude photos."
    Theory #1 — You’re a serial dater, and you’ve grown accustomed to combing all the dating sites. You discovered Casual Encounters while looking for an impromptu chess partner, and became addicted to reading about granny trannies and guys who clean your house naked while you smack them with a pasta fork. Now that you’re in a relationship, you’ve abandoned all the other sites but can’t seem to give this one up. Degree of Threat: 1.
    Theory #2 — You’ve cheated on a few (okay, all) of your exes, but otherwise you’re a stand-up kind of guy. You see nothing wrong with looking at a few ads, as long as you don’t contact anybody. Well, nobody good looking, anyway. And how can you tell if she’s good looking? The only pictures she sends you are of her tits. Besides, it’s not cheating if you never meet in person. You tried, but she didn’t show up. Degree of Threat: 5.
    Theory #3 — You love your girlfriend, but lately, not so much. The sex is decent, but sometimes you envy your single friends. You’re not unhappy enough to dump her, but you aren’t exactly “in it to win it” either. You read the “Hot Slut 4 You” ads and wonder what it would be like to go out in a blaze of glory with one stupid, irreversible act. Boom! All the ambivalence is over. Degree of Threat: 3 (sober), 4.99 (drunk).
    As long as you’re not contacting anyone, Slave to Craig, and it’s not interfering with your sex life, I don’t think your Casual Encounters habit is too big a cause for concern. Looking at these ads might be harmless fun, or they may be an outlet (and a relatively safe one at that) for your negative feelings about your relationship. The only reason for you to stop would be if you were a chronic philanderer (see Theory #2) with weak impulse control. The lure is strong, and browsing this kind of site is playing with fire. If you can’t stop yourself, download a program that blocks access to the site. Have your best friend set the password and you won’t be able to hack your way back in. I have friends who’ve used this method to stop looking at the blogs/websites/Friendster profiles of ex-boyfriends and girlfriends, and it worked like a charm.

Dear Miss Information,
    I’m dating a few different men. I made the mistake of sleeping with one of them on the first date. We were drunk, and I was stupid. I don’t want to be exclusive. I really don’t think I’m up for a relationship. I’m thinking I should tell the guy I had sex with that I’m dating other men, but that I’m only having sex with him. Is that enough? — Northeaster

Dear Northeaster,
    It’s actually too much. Saying “But I’m only sleeping with you, baby,” implies that you’re not going to have sex with any of these other men. Is that true? Is that the kind of commitment you want? To be sexually monogamous with someone you don’t even want as your boyfriend?
    Maybe you do, but I’m guessing you don’t. If you keep dating, sooner or later there’s going to be another guy who you’ll want to get down and dirty with as well. Then you’ll need to have a whole new conversation with Mr. Numero Uno about fucking other people in addition to the one you already had about going on extracurricular dates. Sounds fun, right? There’s nothing better than unnecessary repeats of difficult conversations.
    I would tell him you’re going on dates with other guys and that you’re not interested in the whole old-school going-steady-at-the-ice-cream-social. If he happens to ask if you’re sexually exclusive, you can tell him, but don’t mislead him into thinking your current fidelity is intentional if it’s more a matter of timing and circumstance. You don’t want him reading into something that’s not really there.

Dear Miss Information,
     I’ve heard of several toys designed to stimulate the prostate. As a hetero male, I’m a bit wary of pretty much anything that goes up the road less traveled. Are these products worth the hype? What is my girlfriend going to think when I begin a conversation with, "So there’s this thing I stick up my ass . . . "? — Road Wary

Dear Road Wary,
    “People from all different sexual backgrounds get into the joys of butt love,” says Rebecca of Babeland, a women-owned sex boutique that’s been telling people where to get off for over thirteen years. “The anus and the rectum are sensitive areas. There are a wealth of muscles and nerve endings around the anus and the right kind of touch can feel fantastic.”
    Damn right, Rebecca. But how does Road Wary broach the subject with his girlfriend? “It’s nice to experiment alone first so you can control the pace of your explorations,” she says. “You might want to explore first with your finger.” In other words, do a little anal probing yourself before asking your girl to don a strap-on and play Spock to your Captain Kirk.
    Once you you’ve done that, start working ass play into your regular routine. Ask her to put a finger up your butt while she gives you a blowjob, or have her massage your perineum while you’re doing it missionary style. Masturbate together and show her how you jimmy your backdoor, or take her shopping for a sex toy and ask, “Where’s mine?”
    I asked Rebecca for a few toy recommendations. First on her list is the “Aneros MGX.” It’s specifically designed to stimulate the prostate and (according to Rebecca) can produce “incredibly intense orgasms.” There’s also the hilariously named “Little Flirt,” which has a swell in the middle and a slim profile that makes it great for shy butts, and the “Protouch Plug,” which has more of a vibrator-like action.
    Whatever ass toy you pick, go slow, says Rebecca. “Remember this butt mantra: relaxation, lubrication, communication.” (I’d also add: no recreation before defecation, but that’s not up to me.) Lube up like you’re running a porn-star marathon, and make sure anything you put in your butt has a flared base to prevent it from traveling past the point of no return. No one wants to become an urban legend.  


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