Miss Information

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

Dear Miss Information,
    I want to come on my girlfriend’s face during sex. At first she wasn’t into it, but now she says she’ll try it. Any tips on how to do it in a gentlemanly way, if that’s even possible? — About Face


Dear About Face,
    I remember the first time I drank bubble tea. I spat it all over the sidewalk. You see, my friend hadn’t warned me about the texture — miniature garden slug is the first thing that comes to mind. I’m not saying your spunk is anywhere near as nasty, but giving your girl some preparation is important in this situation.
    Have her watch some adult flicks that include facials and ask her what she does (or doesn’t) like about the act. Have some sex sessions where you ejaculate on more demure areas of her body, like her breasts or the small of her back. Try ending your next blowjob with a little on her face and the rest in her mouth — a fifty/fifty sort of deal.
    You might want to consider doing it in the shower the first time. The hot water and steam do double duty as a hot backdrop for your encounter and as a quick way to clean up. Sure beats a Van Halen t-shirt or a cruddy towel.
    One more thing, About Face: A lot of women are hesitant to try a facial because they’re worried it will be degrading or that their partner will view them differently after the act. Make it a point to turn up the sensitive cuddle stuff and praise her many non-sexual charms. Going on an ice-cream run for her favorite flavor immediately afterward wouldn’t hurt, either.

Dear Miss Information,
    My new boyfriend is a cross-dresser. I don’t have any problem with this, but how do I introduce him to my family? I’m afraid I won’t be able to deal with the criticism. — Is Love Enough?

Dear Is Love Enough,
    You say he cross-dresses, but you don’t talk about to what extent. If it’s recreational, just keep it quiet, and take him over to mom’s for meatloaf when he’s not en femme.
    If it’s part of his everyday life, you have a bigger task ahead. Start laying the groundwork way ahead of time. Tell Mom and Dad you have a new guy and start talking him up like he’s the cat’s pajamas times ten. Talk about his job, his hobbies, his pet turtle named Fred. When it’s time to drop the bomb, your parents are more likely to have bonded with him as a person. Once they know, schedule the in-person meet-up right away. You don’t want to give your folks a lot of time to form preconceptions.
    I’m thinking about a former coworker who was missing her big toe. She would wear sandals and show off a new pedi like it was nothing. I worked with her for two years before I even noticed. She never acted like it was something to be ashamed of, and as a result, neither did anyone else. That kind of calm self-confidence is key.

Dear Miss Information,
    A few weeks ago I hooked up with an insanely hot boy. I haven’t seen him since, but he’s been calling daily. I asked him out, but he said he was busy getting ready for a trip. Should I bag it or keep hope alive? — Lady in Waiting

Dear Lady in Waiting,
    I was going to respond to your email weeks ago, but I lost the password to my account when I was rearranging my desk drawers. Then I started reading this comic strip about a dog named Marmaduke (gosh, he’s funny) and . . .
    See how lame this sounds? Now turn around and look at what you’re putting up with from this guy. You’ve given him two really big clues that you like him: asking him out on a date and taking off your clothes (not necessarily in that order). Now it’s his turn and he’s not holding up his end. He may be busy, but no one is so busy they can’t spare the ten seconds it takes to ask you out.
    He wants to let you off easy. He figures a bunch of pointless calls are better than being a total assbag who disappears. But in a way, this wishy-washy shit is even more irritating. You waste your time and affections along with your calling-plan minutes.
    Stop returning his calls and do not ask him out again. There’s a small chance this might be enough to bring him around. Something about pulling the carrot away seems to work with a particular segment of the population (specifically, the romantically inept and socially immature). If he begs and pleads, go out with him if you must. I know “insanely hot” is hard to resist. But keep your dukes up.  

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