Hey, Faggot:

Little bit of advice for Can’t Wait Anymore, the 21-year-old virgin: don’t visit an escort for your first time! This advice comes from a 23-year-old virgin. Yeah, it’s tough at times–especially with most of society telling you that all couples are fulfilled and happy, and all singles are sad and incomplete. But in the future, when you think back to your first time, what would you like to remember: something special with someone you cared about, or a sexually unsafe encounter that left you with a considerably lighter wallet?

You described yourself as “not very attractive or interesting”–sounds like your problem’s with your self-image, not your virginity! There are groups and organizations for people interested in both mainstream and incredibly obscure hobbies. Maybe you can find someone there, and the first time can actually mean something. If not, hang tight, and enjoy yourself, if you know what I mean. It’s bound to come along–almost no one gets to be 40 years old and still a virgin.

Me, I know why I’m still a virgin: a 257-pound man is not exactly that attractive to the opposite sex! But I know why I’m unattractive, and I’m doing something about it: getting my load lightened and my head screwed on tighter. Don’t be passive, waiting for the girl to come to you. Ask women out even if you’re dead sure they’ll turn you down, get involved in hobbies and activities, or even take out a personal ad, for Pete’s sake! Even if at first you’re not successful, you’ll at least feel in control, like you’re doing something about your love life and maybe opening up some romantic possibilities.

I’m not faulting you, Dan. He asked for advice on how to use an escort and you answered. I just feel strongly about this subject. –Waiting in Chicago

Hey, WIC:

You’re content waiting, and I think that’s grand. Really. And I admire your commitment, though I should warn you there are plenty of 40-year-old virgins: I get letters from them all the time. In general, I think your advice to Can’t Wait Anymore is good–but there are two bones I’d like to pick with you. First, the implication that an experience with an escort can’t, by its very nature, be something special. The experience need only be as creepy, uncomfortable, and unspecial as the escort and client involved decide to make it. And plenty of first-time experiences with no escort present are less than special–ask anyone who’s actually lost their virginity.

Secondly, you imply that an experience with an escort is inherently “unsafe.” Remember, most people get STDs doing “something special” with someone they care about and not from escorts. I’ve met a lot of escorts over the past few years, boys and girls, and every one of ’em told me they insisted on condoms, even with clients who claimed to be virgins.

Hey, Faggot:

Can you get hemorrhoids from anal sex? I’ve got to know before I do it! –Roscoe Pee Cold Train

Hey, RPCT:

My father has hemorrhoids; I don’t. My father doesn’t have anal sex; I do. If you were to draw any conclusions from my immediate family’s hemorrhoidal history, you would have to conclude that not only doesn’t anal sex give you hemorrhoids, it actually prevents them.

Hey, Faggot:

During the summer I had a part-time job working in a lingerie store. It is the company’s policy to let men who wish to do so try garments on. I happened to wait on one and accidentally got to see him dressed up in the fitting room. At the time I found it somewhat disturbing, but the more I think about it, the more exciting I find it.

My questions are: Is this “normal”? And also, how can I ask my boyfriend to wear some of my clothes sometimes without offending him? –CMD

Hey, CMD:

Normal? No. But so what? “Normal” is very rarely “exciting,” and it is the potential excitement factor that’s making you want to cross-dress up the boyfriend, right? So don’t sweat normal.

As for how best to ask him, well, how has he responded to other, perhaps less out-there requests in the past? Is he generally open to new things? Has he ever asked you to indulge him in something fun and freaky? If the answer to the above questions is yes, he’ll probably go for it. So why ask? Just tell him about that guy you saw at work, how much it turned you on, and hand him a few sexy thangs. He’ll know what to do.

Hey, Faggot:

My girlfriend and I are a mature, experienced, and committed couple. We’ve been together almost ten years. We’re still passionate, and sex is a big part of our lives. Lately things have gotten a little complicated, though, and we’ve had our first real disagreement.

She is quite jealous and upset by any interest I might show in other women. This is OK, as I only have eyes for her. She, on the other hand, enjoys sex with other men a lot. She is in fact turned on by having sex with other men while I hold her close and whisper of my arousal and devotion. I have arranged this for her more than once, feeling that her being so wild and free with me right there was something of an ultimate statement of openness and trust in me sexually.

Recently, however, I’ve discovered she’s been meeting guys for sex when I’m not around. She says she imagines me during these encounters and that I’m what turns her on even when she’s with other men, but when I’ve asked her to include me in her solo adventures she becomes very upset. I’m starting to feel differently about her openness toward me. How can I get us back on track?

–Loves a Bad Girl

Hey, LABG:

If you don’t already have the word “chump” tattooed on your forehead, you might as well go ahead and make an appointment. She imagines you during encounters with other men? And that makes cheating on you OK? Wow, that’s a new one. I’m trying to picture what would happen if I went home and tried that. “Honey, I was boning this other guy’s brains out, but it’s OK–I was thinking of you.” Hm–it’s coming into focus. After he finishes beating my head against the floor, he’d take the credit cards, step over my body, walk out the door, and I would never see him again.

Look, your girlfriend is a slut with a big-time double standard. And you? If you buy that mother lode of crap about her imagining you while she’s out boning other guys, well, you’re a bigger chump than a guy has a right to be. If she’s going to mess around, you should have the right to at least look at other women. The fact of the matter is that she doesn’t trust you and isn’t very open. She takes advantage of you and treats you like shit. If you enjoy that kind of treatment, stick around–it will probably only get worse.

Send questions to Savage Love, Chicago Reader, 11 E. Illinois, Chicago 60611.