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Dear Miss Information, I've been trying to broach the subject of anal sex with my girlfriend. I really want to give it a try, but I'm not sure if she'll be cool with it or not. I've stuck fingers up her ass before, but obviously the shaft is different. Should I tell her it won't hurt that bad — even though I really have no idea? Please help. — Balloon Knot Explorer
Dear Balloon Knot Explorer,
Anal sex is rarely pain-free, especially on the first few tries. So leave that out of the sales pitch. If you over-promise and under-deliver, you're less likely to get a second try. Anal sex should be approached in stages. First, finger play. Then an anal vibrator or butt plug. Then a slightly bigger anal vibrator or butt plug. Then slow, gentle penetration. Then slightly faster penetration, and so on. It helps to think of butt sex as a long term project, and the local sex store as your Home Depot. They'll have lubes, condoms, toys, books. Some even offer classes. Make a habit of popping over there on weekends, after you guys have read the paper and had brunch.
Several ways to broach the subject:
Hey Honey, Look What's on TV: Nothing says subtle like porn. If you've never watched together, rent something that's relatively softcore but has a few anal-centric shots. If you guys are old hats, pick something that's all anal so it stands out. Show enthusiasm. Not "Oh my God, Audrey Hollander's pussy belongs on Mount Rushmore!" but "I want to try that with you. That looks hot."
The Unmentionable & Unmentionables: Surprise her with a new pair of underwear: a thong, or something with a lacy keyhole cut-out above the derriere. She models. You say, "You know what those make me want to do, don't you?" She says, "What?" Circular bed starts rotating, huge tube of Astroglide lowers down on a string, fireplace self-ignites.
While I Have Your Attention: Your fingers are "stuck up her ass," as you so romantically put it. You breathe in her ear, "I'd love to replace this with something else." She says, "Oh yeah? What?" You vocalize a reply or just lead her hand to the body part. Two years later you're known as "Mr. Anal Sex," and your how-to book is endorsed by Oprah.
Show Her This Column: Hi, B.K.E.'s girlfriend. He wants to have anal sex with you. Is that okay?
Sadly, you probably don't own a circular bed, and (even more sadly) your girlfriend could say no. If she does, respect that decision. But let her know that if she ever does change her mind, she can direct the whole enterprise however she wants. Give her time and be mellow.
Dear Miss Information,
I want to have sex with a woman I've only known for a few hours. I know it's not that kinky or anything. But it's been a turn-on for a long time. I'm a non-drinker. I don't patronize bars and pubs. I'm handsome, and I know how to be a good lover, but it's still hard to find partners.—Seeking Kinky Kindred
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Dear Kinky Kindred,
Your problem starts and ends with the following sentence: "I don't patronize bars or pubs." Were you asleep during the filmstrip? Surely even a non-drinker like yourself knows the effect alcohol has on judgment. Safety? Disease? Loving, loyal partner? Pshaw! I'm going to get naked with this here stranger, and see how that works out. If it doesn't, and I wind up dead, with a DUI, or catching an STD from a Danzig roadie, oh well. I had a good run.
Good luck finding a non-sexual social outlet where women will be open to immediate invitations. You may get lucky with one out of every thousand fillies you meet at the laundromat. The rest are going to slap you or ask if you've been huffing the Clorox.
I would try places where people are already half-naked and sexually charged — bathhouses, beaches and vacation resorts. Hussies-in-waiting might also be lurking in places where people often act wilder than their normal selves: outdoor rock concerts, wedding receptions, hotel bars, casinos. Video booths and adult bookstores are also fertile ground, but you're likely to run into professionals there, so watch out.
The other alternative, the most sensible one, is to find a local sex party or check out the online personals. There are sexual and non-sexual categories, and you can create a custom pervert manifesto, describing exactly the kind of experience you're looking for.
Dear Miss Information,
I lead a funny life. I am twenty and have never had a girlfriend. I'm not ugly, stupid, and I have a good sense of hummer. Hot drunk chicks want to make out with me (if that means anything). I am so fucking shy tho. Nothing goes anywhere. Most of the girls I go out with, I meet parties when I'm good and liquored up. How do I meet women without liquor? God, it seems I will never get this creation of love I made in my head (mix some Fiona Apple songs with Eternal Sunshine of the Spotless Mind, Annie Hall, and Harold and Maud (even though Harold And Maud is more about how to love then being in love). So how do I get it all without losing my head? Or being drunk. — WTF
Dear WTF,
You know who also has a good sense of hummer? Rap stars and Republicans. I hear they even put fancy rims and TV sets in them, which must make it difficult to walk around. Just curious — were you drunk when you wrote me? For a drunk guy, you have pretty good taste in romantic comedies. I'd have thought you'd bring up American Pie or something.
You're saying booze is the only reason you've had any success with women. Take away your Wild Turkey and you're like Samson without his luscious locks. But is booze a prerequisite for all your other relationships? Do you have to get drunk to talk to your parents? Your coworkers? Your friends? Dating is just another type of relationship. That's how you need to view it, WTF. Stop putting it on this crazy emo/Hollywood pedestal. Girlfriends are nice but your life is not going to be magically altered when you get one. You won't be inoculated against bad fortune, shitty traffic and sullen moods.
Set small goals: "I'll talk to one girl in my class today." Doesn't matter who it is, as long as she's female and not the professor. "I'll talk to two women today." "I will talk to one woman for more than five minutes." After you've completed your daily assignment, the rest of the day is yours.
Also, work on finding some social activities that don't involve alcohol. It doesn't have to be museum excursions or high-energy day trips (but if you like that, try Meetup.com). Personally, I've been able to cut down on my boozing by sitting on my ass and watching Netflix. Readers, any cinema suggestions for WTF? What are your favorite romantic comedies and/or flicks that celebrate singlehood?
