Dear Wyndham, I just got out of a long, tumultuous relationship and the last thing I want to do is get involved with someone new. That being said, I also really want to get laid. How do I ethically sleep around without sending mixed signals?

—In Need Of A Booty Call

Short of getting membership into Club Wicked, the best way to go about this is through straight-up honesty. At bars, parties, or through friends of friends: there’s a lot of people (yes, girls too) that just want some horizontal mambo, no strings attached, and while meeting them isn’t always easy, it’s not impossible. But when you do meet a foxy lad/lady that you’d like to sex up, you’ve gotta let them know the score.

While that doesn’t mean revealing it during a handshake introduction, it is always helpful to slip in some hints during the chit-chat that follows (for example, dropping in a “Right now, I’m focusing on having fun and meeting as many people as possible” is usually a good clue that you aren’t on the monogamous track).

My rule to let someone know that I don’t want to go further than one night is to come forward post-initial kiss, which allows them to decide if they want do get down, or if they’d rather go home and look at wedding magazines. You’ve got to be brave, and stick to your word: no spending the night, no “I can’t believe I met you,” no promises of calling in a few days. People who give mixed signals are cowards who don’t have the balls to say how they really felt, so they put on a façade of romance. At the beginning of making out, let him/her know what you want out of the evening, and be prepared to accept that your truthfulness might cost you the booty. But getting laid under the false pretence of a possible romantic future is one of the cruellest things you can do to another person.

Dear Wyndham, I have a great boyfriend who thinks our vanilla-style lovemaking isn’t enough. Lately he’s been putting pressure on me to do more and more explicit things—anal sex, dirty talk, and finishing on my face. I’m not quite sure I’m ready, but I love my boyfriend and want to make him happy. How can we find a happy medium?

—Can’t We Just Cuddle?

Oh, sweetheart. We’ve all been there in some way or another, and while I usually stick with Dan Savage’s mantra, (you’ve got to be “good, giving, and game” in bed) acquiescing when you aren’t comfortable is only going to cause trouble.

When you have a partner that wants to try something new, you should first take a moment to think back to your recent fantasies and daydreams. Is this something that you have independently thought would get the juices flowing? If you are both interested in anal sex but worried about discomfort, anal toys (like butt plugs, which come in a variety of shapes and sizes) are a good way to ease you in. So is a finger, which is significantly smaller than a penis. If this play arouses you without any pain, then you can decide if you want to move further.

Same with the others: dirty talk can begin with just saying, “I want you, you turn me on,” and a guy can ejaculate on your thighs or breasts to see if you like the feeling. You (and your partner) shouldn’t expect to move into new territory overnight—that will likely leave you both shaken and confused (and probably sore). But fundamentally, if your boyfriend or girlfriend is suggesting something new that you have never thought of as fun or sexy, proceed with a lot of caution.

It’s okay to say no, and still be an open-minded and generous lover. Most importantly, you both should feel comfortable and hot together, be it through urinating on each other, or just snuggling under the covers.

Dear Wyndham, I’ve been having sex for about two years now with various partners, and well, I can’t get off. Whether it’s fingers, tongues, or penises, it doesn’t seem to matter, and I’ve certainly been with guys who seemed to know what they were doing. I’m sick of lying to myself, and to them. Though I can make it just fine on my own, will there ever come a day when I orgasm with another person in the room with me? What the hell is wrong with me?

—It Was Not That Good For Me

There’s nothing wrong with you, and most of us have faked enough orgasms to put Jenna Jameson to shame. But faking isn’t constructive, it leaves you unsatisfied and your partner with a false sense of accomplishment.

If you can get yourself off through your own hand, then why not do that with your partner? Layers of skin sheath the pleasure receptors in the clitoris, causing many women to only reach orgasm through battery-powered devices. Using a vibrator or your hand to stimulate you during sex (doggy-style is popular for a reason!) is a good way to reach climax, as is mutual masturbation with your partner, which can be one of the most intimate sexual acts.

And if your guy/girl gets uppity because you need assistance? Fuck them. Or more precisely, stop fucking them, and find someone who wants nothing more than to see you come, whatever the method.

Dear Wyndham, Whenever it’s that time of the month, let’s just say I get antsy. I want to try having sex on my period but am concerned about the whole gross-out factor for my partner, not to mention clean up afterwards. Any tips on how to get down when Aunt Flo’s in town?

—My Bloody Valentine

Period sex can be a divisive issue—some people find it awkward, while others have honestly told me that they couldn’t care less if I happened to be surfing the crimson wave.

First of all, you must talk to your partner beforehand, as no one wants that kind of surprise in the midst of coitus. If you’re both comfortable but worried about the uh, mess, the most common route is to do it in the shower, where you can both end up even cleaner than when you started (and water pressure can add to the mix). If you simply want to get off but don’t necessarily crave penetrative sex, you can wear a tampon while fooling around with your partner and orgasm through hand or vibrator contact.

Some guys have felt more comfortable having period sex with a condom on (which you should really be using anyway), and placing a towel beneath you is usually a good bet to save your sheets any stray stains. Since we spend 25 per cent of our time on the rag, it’s important to talk to your partner and find a medium that works for both of you. Besides, nothing else soothes cramps like some time in the sack.

Dear Wyndham, When I masturbate, I fantasize about having sex with guys in the AC shower. All my past relationships have been with women, but this idea really seems to turn me on. Am I gay?

—Probably Into Chicks, Right?

Probably not, though “gay” and “straight” are pretty restrictive labels. Most people have been, at some point or another, attracted to members of both sexes, which is totally normal. Furthermore, you would be hard pressed to find an individual that has never fantasized about a member (or members) of the same gender, or been aroused by the thought of exploring that frontier.

I’ve had boyfriends that have only dated women but admitted to watching gay porn and thinking about men naked—and those guys made the best lovers! If you start being attracted to the men you meet in person, then you should follow your heart (or your cock), but whether you live out your fantasy, or it remains as such, you shouldn’t worry about your sexual identity. You can date a man and still feel heterosexual, and you can certainly fantasize about it and be straight as an arrow. Fantasies are fun, and they should never be impeded by moronic social codes that attempt to place us in arbitrary and restrictive categories.

But the AC, really? All the hot guys shower at Hart House.