Thinking about hanging with the other side for the first time?  Whether mostly gay or mostly straight, here’s some tips on how to smoothly transition into the wonderful world of bisexual pleasures…

First of all, let me start with some quick definitions of terms. A bisexual is someone who is approximately equally attracted to members of both sexes. (Apansexual, for those who are wondering, is someone who is attracted to allgenders and all sexes. No one’s tried to come up with a word yet for people who are pan-curious, just like no one’s come up with a word yet for people who have a sexual preference for transpeople. “Transsexual” was already taken). I do not believe that a person actually has to have had sex with people of both sexes in order to “qualify” as bisexual. They just have to (1) badly want to, (2) fantasize about both sexes fairly often, and (3) actually be attracted to real-live human beings of both sexes. In my book, bicurious people, on the other hand, are people who do not fulfill one or more of the criteria above, but are interested in sleeping with someone of the Unknown Sex (i.e., the sex they’ve never fucked). In my experience, bicurious people most often fail on criteria #3 (they often drool over celebrities of the Unknown Sex, but are rarely actually attracted to people in real life) and #1. Instead of “badly” wanting to sleep with the Unknown Sex (it’s the faraway look that most people who actually enjoy sex get when talking about it that we’re looking for here), they have a look of interest and, well… curiosity. To be bisexual, you need to have the same kind of drooling expression on your face at the prospect of fucking the Unknown Sex that you do with the Known Sex. The rest, until tested, are bicurious.

Since it’s relevant to that “drooling expression,” I want to take a moment here to rant about some of our culture’s stupider ideas about what constitute “sex.” Somewhere along the way, our culture developed this incredibly obnoxious idea that “real sex” between men and women was intercourse, “real sex” between two girls was oral sex, and “real sex” between two guys was anal. This notion is so pervasive that I frequently hear hetero-leaning bicurious girls admit that they find the idea of fucking girls appealing, but they just can’t work up enthusiasm for eating one out–therefore they must not be bisexual. My favorite example was a bicurious friend who confessed that she fantasized about fucking girls, but only “doing things that weren’t physically possible.” When I probed this comment a bit, it turned out that her main fantasy was tribadism, which she had no idea actually existed (also known as tribbing or scissoring. It involves two girls wriggling their genitalia against each other.  It’s fucking hot, people). She laughed, telling me that she felt like her bisexuality had just been “validated.” If we’re going to disqualify people based on their taste for specific acts, I think a lot of “straight” people who aren’t that into oral sex just lost their straight cred, and the something like 25% of “gay” men who don’t do anal sex just lost their gay cred. Don’t listen to your culture: if it’s arousing, involves genitalia, and you do it with another person, it’s sex. Okay, rant over, back to talking about sex 😉

When it comes to bicurious cherry popping, it’s important to try to place yourself in one of the following categories: people who have had great sex with their preferred gender and people who have not. If you’re one of the “bicurious” folks who’s contemplating switching sides because you’ve been unimpressed with the cuisine thus far, you need to approach things very differently from people who have had awesome sex with their Known Sex and are looking for the Next Great Time. Indeed, your experiences are so different that I’m going to exclude the first group of people from my “bicurious” category and label you “questioning” instead. Why the difference? Because “bicurious” folks are wondering if they’re bisexual; “questioning” folks are wondering if they’re actually gay/straight. There’s a world of difference in how you go about trying to answer those questions, both in terms of your own personal identity and in terms of your relationships with others.

I’m basically assuming that if you’re calling yourself “bicurious,” you’re mostly out looking for a good time. If you have a very good time, you might decide to change that identification to “bisexual” and approach sex with the Unknown Sex more seriously. Given that you’re really not sure how this is going to go, you have to be careful about your partners. In my not-so-humble-opinion, you should ideally try to “test” your bicuriosity in hook-ups or friends-with-benefits situations, because less is at stake. Since you really don’t know how this is going to go, you want to be in a situation where there isn’t too much pressure for a repeat encounter. If you’re the kind of person who just can’t do sex without some semblance of a relationship, then at a minimum, be absolutely open and honest that you’re exploring and you’re not sure. There are plenty of gay/bi/straight people who just lovvvvvve cherry popping, so you shouldn’t have a shortage of offers by telling the truth.

Although I advise bicurious folks against experimenting with bisexuality in a relationship with the Unknown Sex, I also think it’s important to avoid the other potential pitfall: fucking whomever. Many of the bicurious people I know regularly (even constantly) get propositioned by the Unknown Sex–it’s part of why they became bicurious in the first place. Once you’ve decided to pop your cherry, it’s very tempting to just accept the next offer that comes along, since you’re not looking for anything serious anyway. Despite its intuitive and practical appeal, this is actually a very bad idea. As someone who has had sex with both guys and girls she is not attracted to (never without an orgy!), you should take my word for it: having sex with someone you’re not attracted to is no way to test out any theory of your own sexuality. Having sex with someone you’re not attracted to of the Unknown Sex will be at least as unexciting as having sex with someone of your Known Sex that you’re not attracted to–and awkward to boot. (Really, all other things being equal, having sex with anyone you’re not attracted to is generally actually a step down from masturbating). At a bare minimum, you should be turned on by the idea of kissing the person in question and seeing him/her/hir naked. In sum, save your cherry for someone who makes you horny. Otherwise, your experiment is guaranteed to fail from the start.

Of course, many times the opportunity to “test” your bicuriosity emerges without much planning, frequently in the context of a drunken threesome. While it might be lots of fun, if you’re looking to evaluate your potential bisexuality, this kind of scenario is less than ideal. By all means do it! Go forth and fuck with joy! But do not assume that this is all the information you need as you try to determine whether you’re bisexual. If you are bisexual, you don’t need intoxicants (although starting out, they might be very useful in small doses…). Also, there’s still a world of difference between screwing the Unknown Sex with your partner of the Known Sex versus all by your nervous self. All enjoying a drunken threesome tells you is that you enjoy a drunken threesome.

When embarking on this experiment with bisexuality, you have to think back to the early days of your first sexual explorations. I sincerely hope you didn’t immediately follow up your first real kiss with your first real fuck. I know some people do, but I’m also pretty sure it doesn’t usually result in mindblowing sex. You can–and probably should–take it slow with the Unknown Sex. Make out. Pet. Give handjobs. Exchange oral sex. It’s generally not a recipe for good sex with either the Known or the Unknown Sex to have all of these things happen in instant succession on the first try. If you manage stellar sex with someone you just kissed for the first time–well, you got lucky in multiple senses of the phrase. You know less about what you’re doing with the Unknown Sex (yes, even if it’s your own), so don’t try to move things along at breakneck speed. Even if you feel like you’ve had a crazy opportunity that is unlikely to be repeated, don’t feel obliged to go “all the way.” At the same time, you don’t want to be kicking yourself for weeks/months/years to come for not taking advantage of a chance you’d been longing for. As with any sexual exploration, you have to find a balance between what’s comfortable, what you want, and what you fear.

Now, once you’ve gone and popped your cherry, there’s an unfortunate temptation to compare your sex with the Recently-Known Sex to the best sex you’ve had with your Well-Known Sex. Don’t. You’re much better off comparing your recent bicuriosity exam to the first sex you ever had with the Well-Known Sex. That’s not an entirely fair comparison either, since presumably you’ve learned something about the Art of Sex since you were an innocent virgin. But you can’t expect sex with the New Sex to re-make your world the first time you try. What you’re looking for is to see if it’s hot enough that you want to try it again, and if you find yourself fantasizing both about the experience and/or improved versions of it afterwards.

If so, welcome to the wonderful playground of bisexuality. If not, what the hell. At least you gave it a shot.