Miss Information: What’s the best way to ask a woman to have casual sex with me?

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Dear Miss Information,

What’s the best way to go about asking a woman to have casual sex with me? I’m a guy. I’d like to have a friend-with-benefits, and some one-night stands. — Budding Libertine

Dear Budding Libertine,

Women you know, or women you meet on the Internet? Big difference there. I’ve always found that the best, most reliable fuck buddies tend to be people you’ve already met and dated. Not dated as in "we used to share furniture and argue in Whole Foods." More like "we went out a few times and everything was scintillating except for the conversation." There’s also the "we went really far, really fast, and nobody called anybody the next day" as well as the "just a matter of time" platonic friend. All of these people you can take out for a drink somewhere poorly lit on the pretext of catching up and let what happens happen.

The majority will know what you’re up to, but compliments on their physical appearance, games like dirty-word Scrabble or erotic Photo Hunt, and flirty body language will help move things along. It also helps to look good and be polite. Walk at her pace. Hold doors. When she talks, don’t let your dick distract you from the moment.

As far as women you encounter online, I’m going to turn that over to my friend J. My experience in this realm starts and ends with getting wasted in 2005, logging on to the web, and asking dudes to send me pictures of their dicks. I passed out and woke up to an inbox full of JPGs and a twelve-Advil headache. But J’s done quite a bit of this. Here’s her take:

"I judge a guy by his words. Emails and message are super important. I don’t reply to dudes who type in all caps, can’t spell, or have shitty grammar. I know, it’s just for sex and I’m sure dumb people are great at fucking. But I don’t want to bone them. Also, when a guy replies with what looks like a form letter, that gets deleted. Did he even read my ad? Does he know what I’m looking for or is he just saying ‘Yo, I wanna fuck you, I don’t care what you want or think’? Because that’s the impression I get."

J says those who really want to get laid and have mitigating circumstances may have to deal with unpredictable schedules:

"It’s really unsexy when a guy gets whiny and tells me to fuck off when I flake on meeting him. How am I going to make him a priority if he has a wife? I may be a slut, but I’m not a husband-stealing whore."

She also recommends using multiple sites. Think beyond the one that starts with C and rhymes with "ist."

"I have many fuck resources," she says, though she acknowledges that the aforementioned is "the quick-and-dirty instant ramen noodles" for folks wanting a quick bang.

Read more of J’s musings at Cruising with the Awesome Slut (NSFW, shocker).

Does anyone else have any more tips for Budding Libertine? What can a guy do to let horny ladies know he’s hot, cool, and not psychopants?

Dear Miss Information,

I am a straight guy and fairly submissive to my wife. I really, really love going down on my her but I also want her to shave — if not wax — her lady area a lot more often. The experience is getting unpleasant for me with all that fibrous interference. How do I stay a sub but also be more insistent with her about going downtown? For comparison, I have thought of asking her to try out some smooth lady areas of other women to know where I am coming from, but try-sexual is a whole other suite of issues. Suggestions? — Would Love Just a Landing Strip

Dear Would Love Just a Landing Strip,

Wow. I’m pro-pubes but the phrase "fibrous" used to describe anything south of the panty border elicits a knee-jerk urge to immerse myself in Nair.

Asking your wife to eat someone’s bald pussy as a way of showing her you like bald pussy? Bad idea, my friend. You know better than that. Threesomes are one of the few sexual requests more politically fraught than body hair. Of course you can ask your wife for a little polyamory action, but like you said, that’s opening up a whole mess of issues. One thing at a time. Let’s make sure we put away our crayons before we break out the fingerpaints.

Do you guys role play? If so, you’ve got a pervy treasure trove of ways to work hair removal into the equation. Offer to strip naked, get on your hands and knees, grab a pair of eyebrow scissors and give your mistress a trim according to her exacting specifications. You could also give her permission to do whatever she wants to your bits and pieces while you have to "earn" grooming privileges for her naughty bits by performing sexual favors. How about making it part of a whole head-to-toe dom/sub spa day in which you do everything from massaging her scalp to shaving her pussy and painting her toenails? Bonus points if you get into character with a white uniform (or loincloth) and succumb to your glamorous femme fatale of a client’s demand for a happy ending.

A couple final things to remember:

– Be sensitive. What’s a nuisance to you could be deeply tied to her self-esteem. Not to sound like a douche commercial, but it’s one of the most personal areas of a woman’s body.

– Don’t be prescriptive. There are a zillion hair removal choices out there. Let her figure it out. Assuming she wants to figure it out. It’s not your time, money, or body.

– Comparisons are for jerkoffs. I’ve been through my share of relationships and tried out a variety of ladybits styles. The one thing I’ve never (ever!) responded to? Guys who bring up ex-girlfriends or porn stars as potential pubic hair role models. Of course you can think it. But don’t say it.

Readers, any other thoughts for Would Love Just a Landing Strip?

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