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Directions for Using Dildos and Dating Online

Go ahead; tell him to bend over or give internet dating a go. Our expert's got tips for both.

Friday Oct 12, 2007.     By Anna Pulley

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Dear Maven,

My boyfriend wants me to f**k him with a strap-on. First question: Is there a more polite way of phrasing that? Second question: I'm more than a little apprehensive, but think it would be pretty hot. Any advice for first timers?

Sincerely,
Going Deep

A: A more polite way of talking about strap-on anal sex? Well, if you're giving a preschool lecture on the topic, "poopy dick" is the term school administrators prefer. Some people, including Midwesterners, carnies and a certain sect of Presbyterians, call it "pegging." And if you're Al Gore, it's called Thursday. But who cares about politeness? You're not sharing a scone with the Queen. (If you are, then we've seriously misunderstood each other.)

Here are some guidelines for pegging or Tips and Ass, as I like to call it (though poopy dick is a close second):

1. Use a lot of lube. I like a good water-based lube like Sliquid or ID, but it's mostly because they're paying me in sexual favors. (They made me say that, too!) Oil-based lubricants also work well with dildos (and are the secret ingredient for a fall marinade, according to Oprah's magazine). Spit alone does not do the trick. You must invest in lube and reapply often.
2. Start slow, with a well-lubed finger. The bum is like dealing with a fussy child or Republican Senator—you have to coddle it some and not use too many big words. To hit his g-spot (the prostate gland), stick your finger (or two) about two-thirds of the way in, aim for the navel and make a "come hither" motion. As with the female g-spot, you might not find it at first, but the more he becomes aroused, the easier it'll be to feel with your finger. Don't forget to trim your nails beforehand. I don't know how many times Newt Gingrich has called me crying about that.
3. Once he's warmed up, then and only then should you proceed with a dildo. Reapply lube on his ass and on the dildo. Once inside, continue slowly and steadily. Stop if it hurts, but don't make any sudden exits. Sing if you feel the urge (I recommend Salt-n-Pepa's "Whatta Man") because it's a pretty rockin' experience, no ifs ands or butts about it. (Sorry, anal sex talk brings out the shitty puns. (Sorry again!))

Dear Maven,

I just created an online Centerstage personals profile. I'm pretty new to the whole online dating scene and was wondering if you had any guidelines or tips or etiquette for me?

Thanks,
Tasha

A: My first tip is to not end a sentence that's a statement with a question mark. But, barring that, congratulations! You've just entered the digital age. It's an exciting time, to be sure. There are many rules for online dating and no rules. It's like the Matrix, only with slightly fewer dance orgies (I said, slightly). Since I don't have all day (you do, that's fine), here's an abbreviated version of the online course I taught at University of Phoenix, called "Expiration Dating 101."

1. Post at least one picture of yourself; make it flattering but don't go all Edward Scissorhands with the Photoshopping. Your chances of piquing someone's interest are much higher with a few pictures, because they let prospective partners know that you're not Larry Craig or a gerbil. (I don't know how many times I've fallen for that one). Also, with a photo, your chances of meeting this guy are greatly diminished: "Can you send me a pic? It doesn't have to be of your face or anything." (True story)
2. If you're not interested in someone, don't keep messaging them and dragging it out unnecessarily for the sake of politeness. A simple, "You seem swell, but I don't think we're compatible" gets the job done nicely. Or, "You're swell, but I'm actually a gerbil."
3. Even if you are looking for "the one," don't advertise it, especially with phrases like "willing to relocate" or "I'm ovulating!” It reeks of desperation and, if you get really close to it, that chemically engineered product Taco Bell calls "beef." Stick to the more casual lingo if you don't want to scare away potential sperm donors. Or soul mates.
4. Avoid blanket adjectives like "nice" or "funny" or "narcoleptic." Or, if you do use them, be as specific as possible. "I do a mean Christopher Walken impression" is a totally different kind of funny than "I like to fart on my Grandpa. Heh." At least I think it is. I'll have to check with Grandpa and get back to you.

Anna Pulley, our Meet-Market Maven, has been on more bad dates than J. Lo's been to divorce court. She's been a one-date wonder and Wonder Woman. She's bi, and no she doesn't want to sleep with your boyfriend, thanks. When she's not giving advice, she enjoys theme parties for every and any occasion and working as a Carnal Consultant for Early to Bed. Buy her a drink or ask her a question already.