Miss Information

I want to experiment, but I don't want to cheat on my boyfriend. What can I do?

By Cait Robinson

Dear Miss Info,

I recently decided to start exploring the mighty waters of vaginal penetration. I have had bad experiences before. I mean, bad, bad, bad experiences before, involving abusive boyfriends, invasive gynecologists, and massive panic attacks. But this time, the great ship Pinkie was able to explore the area with no great anxiety, and only minor discomfort. Encouraged by its success, I sent out its sister ship, Index. Alas, poor Index foundered on the rocks. Just inside my vagina, it seems, is a channel that Pinkie can pass through, but Index is too big for. Also, it hurts. I check out vibrators and am dismayed to see that even the smallest ones are way bigger than the fingers involved. I check out my boyfriend's dick, which he would dearly love to put inside of me, and compared to all of these it looks H-U-G-E. Assuming I can get bigger stuff in there, how do I make it feel good? To bring this nautical metaphor to its unfortunate conclusion, Miss Info, how do I get comfortable with my vagina so that we can —

— Free Willy!

Dear Free Willy,

From a strictly brass-tacks perspective, penetration of any sort is uncomfortable at first. Despite being designed specifically to be elastic (they're supposed to pop out miniature humans, after all) vaginas are surprisingly — and unfairly! — persnickety. It's a really fun "fuck you" from biology. You can take cold comfort from the fact that every female in the world knows exactly what you're talking about. This problem has launched a thousand terrible collegiate one-acts; I promise you're not alone.

I do notice, though, that under the nautical theme, the tone of your question seems a bit sterile. How are you attempting penetration? What is your mental framework like? You are going to have a much, much easier time if you're turned on and feeling adventurous. So step one: get turned on and feel adventurous. Your brain has to be on board before anything good can happen with your body.

Exploring the quirks of your own body should not take you anywhere near panic-attack territory. If it does, walk away for a bit. Know that there is no pressure and no time limit. However, if you're consistently hearing the voices of these bad experiences, you should pay attention. Negative emotions can easily put a body on lockdown. Find a sex-positive counselor or therapist to help you process those feelings enough that they no longer, erm, cockblock you. Anchors aweigh!

Dear Miss Information,

I've been dating this guy for more than four years — I'm twenty-four now and he's twenty-five. I'm an overblown, passionate lady and he's never even been interested in anyone else. From the start, we were best friends, but I never really felt that kind of immense desire for him — it sort of came to me over time, intellectually, spiritually. He loves me unconditionally and I love him. But that spark, that sexual compatibility, has never really been there.

The whole time we've been together, my heart and loins have been wandering. I've made out with girlfriends in front of him, confessed about kissing boys, and generally been an asshole, usually telling myself I deserved to have the experience, since before this boyfriend, I had virtually none. He's said no to an open relationship, which I understand. He feels nauseous at the thought of his being with anyone else, not to mention my being with anyone else.

We're both in grad school now, in long-term programs, across the country, and really supporting each other emotionally. Things were going well. But I've met someone here. It's scary, because I recognize this is probably what a more "normal" romantic situation feels like — someone who surprises me, who is far more present (physically and mentally), and who knows what it means to maintain a non-platonic relationship. It's really bringing to light the fact that I've got shit to deal with in regards to my long-term, long-distance boyfriend.

Being with this new person is both thrilling and very cosy. But breaking up with my boyfriend seems unfair — can't we keep learning to work together? Plus, breaking up with my boyfriend seeks unfair to this new potential interest as well, who doesn't need that kind of baggage. Meanwhile, I don't want to lose my sweetest friend and partner. I just don't know that he's supposed to be my romantic partner. I just don't know what to do, really. I feel such an abundance of love, but I also feel so lost, and so very stuck.

— Freaking Out

Dear Freaking Out,

Your desires are part of you, not unlike your arm, your liver, or that tattoo you got at Cabo Spring Break '06. You can only ignore them for so long. If you need to sleep with other people, staying in a long-distance-monogamy thing isn't being honest to yourself or your boyfriend.

The key is that you say you actively want more sexual experience. Totally fine. But you've signed on to a relationship that limits exactly that. So you act out — kissing girls, feeling up boys — then "confess" these transgressions to your boyfriend. Which isn't fair to him, especially since he's made his desires plainly known. What are you trying to get from him? I'd wager that you're trying to leverage distance, to get him to allow you more sexual flexibility while staying in the bounds of your relationship. He's been clear on the fact that he isn't okay with that. As long as you're pulling toward "exploration" and he's pulling toward "monogamy," neither of you will be comfortable in the relationship.

It also seems like your boyfriend and this new guy are both buttresses for you. It's great to form strong intimate relationships, but not at the expense of your own self-sufficiency. You should be very honest with yourself about what need, and give yourself permission to pursue that. Pro tip: a new relationship almost certainly isn't the answer. Try putting your emotional eggs in many different baskets, rather than heaping them on whomever you're dating. That way you'll still be standing if one basket gets hit by a farm truck, or raided by a mongoose representing crappy metaphors.

All in all, Freaking Out, you've got some weighing to do. Either commit to exploring your desires, or commit to your boyfriend, but know that you can't fairly do both. If you need to run to the hills and live in a hippie free-love compound, by all means, do it. Just don't make commitments that you can't fully honor.