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My Boyfriend Might Be Gay. Should I Care?

Hi Yana,

I recently began “dating” my best guy friend over this winter break. He’s told me that he was raised by a super religious mom and that when he was younger he “rebelled,” and experimented with other men, which he blamed on his homophobic upbringing. He told me he’s had sex with another man, but has since concluded that he was straight. I didn’t ask many questions other than, “So, do you think you’re gay?” to which he responded, “No, I’m not gay.”

The night after this conversation, I invited him to dinner with my friends and he brought a male friend. During dinner, they both mysteriously disappeared to the bathroom for over 10 minutes and returned within seconds of each other. When we all went back to my house to hang out, they spent most of their time close together, making flirtatious eye contact, and practically cuddling on the couch. All of my friends noticed these intimate exchanges, too.

The thing is, my boyfriend isn’t really my boyfriend officially, though we have had conversations about being “exclusive.” We’re best friends first, so if he’s gay or bisexual, I’ll deal with it, but I don’t understand why he’s hiding it from me.

Am I being paranoid? Should I talk to him about this? Is he flirting with this guy in front of me because he wants to get caught? I’ve already asked him if he’s gay, and he said no, so why am I obsessing over his sexuality, and how do I deal with the potential fact that the guy I love may be identifying as straight, but secretly hooking up with his male friend?

— Boys Will Be Boys?

Dear Boys,

There’s a lot happening here, made more complex by cultural norms that sort of approve of straight women hooking up with each other, but condemn any and all sexual experimentation between men. Other things that make this situation complex are his experiences in his earlier years, which don’t seem to have given him the permission to explore the differences between his sexual experiences and sexual identity.

It’s totally possible to identify as straight and still hook up with men. That’s something people do and are entitled to do as everyone’s sexuality is theirs to define. Similarly, people are entitled to identify as bisexual even if they’ve never experienced sexual acts with someone of the same or different gender. Your identity isn’t a passport, you don’t need a stamp to prove you’ve been there. But knowing this for yourself requires permission to explore, which maybe hasn’t been granted to your boyfriend.

I want to propose a different, possibly unpopular, way of looking at this situation: Rather than playing sexuality investigator and making it your mission to figure out “who he really is,” view this issue as a communication and boundaries problem. Though figuring out your boyfriend’s sexuality certainly feels important right now, it also isn’t entirely necessary to resolve your particular situation…continue reading…

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How to Have a Discussion about Self Lovin’

Hi Yana,

I’m a 19-year-old male college student. I just started to masturbate, but I don’t know how other people will react if I get into a relationship with them and tell them about this. I would like to know how to be fully comfortable with pleasuring myself as well as see how to bring up masturbation in a relationship. Thank you!

— Seeking Masturbation without Hesitation

I’m reading your question in two different ways: the first is “How do I tell my partners that I just started masturbating at the later-than-average age of 19?” and the second interpretation is “How do I tell my partners that I’m into masturbating, generally?” So, I’m going to answer both.

First: Nothing is more varied than a person’s sexual timeline. The “typical” sexual timeline is dictated by a lot of assumptions — the biggest one being that you have or want to have penis-in-vagina penetrative sex. Others include how and where you were brought up, the kind of sex education you had access to, your moral or religious upbringing, and the health and ability of your physical body. All of these factors and more contribute to the freedom we feel to sexually explore ourselves and others.

This isn’t to say that the most free of us masturbate the earliest, but it is to say that not all sexual timelines suit all people. Part of keeping it consensual is also a self-practice: masturbating when it just doesn’t feel good mentally, physically, or both is not an enthusiastically-yes experience.

Part of your question seems to wonder how to get to an enthusiastic-yes solo-sex experience. The first step is to give yourself permission to head that way: this could mean undoing some negative messages from your sexual upbringing — reading some sex-positive books like The Multi-Orgasmic Man or The New Male Sexuality is a good start — or finding masturbatory materials that feel positive to you like ethical porn (see past columns on “Feminist Porn” and “Grass-Fed Porn”) or pleasure-positive erotica. Cleis Press publishes a great collection.

If it’s greater physical comfort you seek, try a nice, thick jacking-off lube like Boy Butter — not compatible for penetrative sex or latex — or Gun Oil, which is silicone-based. Or you could try a fun masturbation sleeve such as Tenga Eggs, which are cheap and disposable, or a Fleshlight, the notorious self-lovin’ toy for a heftier price tag.

Second: People love telling other people how to have their orgasms. And, very specifically, with whom to have them. And even more specifically, still, to have them in good company…continue reading…

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Open Sex, Closed Conversations

Hi Yana,

I’ve been in an on-again/off-again, oftentimes long-distance, relationship with my for-now ex-boyfriend for six years. Right now we have a “when we’re together, we’re together” arrangement and we’ve defined our relationship as open in the past.

Well, things are shifting again and we’re thinking about moving toward being more seriously together, but still long-distance and open. If we decide to get back together, I’d like one of my boundaries for our open arrangement to be that he not sleep with anyone that I know personally. But now I’m not sure if I want to know if he has slept with anyone I know during any of our in-between times.

On the one hand, I feel like I might make myself crazy if I don’t ask and am left wondering. On the other, I once accidentally found out that he did sleep with a friend of mine during a time when we were broken up that also made me feel really bad. What would you do?

— Friends with Benefits

You’ve combined some of the most challenging relationship dynamics: long-distance, open, long-term AND on-again/off-again!? Damn. Something tells me you might be a glutton for punishment, but that’s 50 shades of a different column for another week.

There’s a common Don’t Ask/Don’t Tell “policy” generally popular with folks new to non-monogamy. DADT tells partners “Do what and who you will, but I don’t want to know anything about it.” Though I get the appeal of DADT for non-monogamy newbies, it does little to shield folks from tough feelings. Instead, it sets people up to deny jealousy rather than learn from it, it closes partners off from each other rather than holding open space for others, and these arrangements typically end with everyone in worse shape than if they Did Ask and Did Tell.

Me? I would want to know. When Dorothy pulled back the curtain on the all-powerful wizard in the Wizard of Oz, she found he was just a nice, lil’ shrimp of a man. Meaning, our minds can play some terrible tricks when we’re feeling emotionally raw, downright jealous, and awfully creative; a fleeting thought that he may have slept with a mutual friend can magically become a convincing story about him randomly meeting Jennifer Lawrence at a cool underground party in NYC and having the best sex of his life with her in some glamorous penthouse because JLaw is basically someone you know right because you just loved her in Silver Linings Playbook and now your ex is going to be famous and you will be nothing. Nothing!

In reality, the people your dude has slept with are all real people — with qualities both wonderful and flawed, sex moves both explosive and meh, and their own set of insecurities and relationship baggage. But, if you never peek behind the curtain, you’ll never know this for sure…continue reading…

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Bad Vibes: Am I too sensitive for toys?

Dear Yana,

I want a new vibrator. The problem is that my body is SO sensitive that even the first setting on all of them are way too intense for me. I could do it manually, but I’m lazy. Advice?
— Vibrators Can Buzz Off

Dear Buzz Off,
First thing’s first: your body and how it experiences pleasure is never a problem! The various accoutrements available to us via the adult industry are there to enhance our pleasure and amusement, not rate us on a scale of normal-to-freakshow or perfect-to-broken. We all just need to learn how to find the right products for us.

For a long while one of my dirtiest secrets was that though I wrote about and sold vibrators for a living, I actually didn’t much like them myself. For the longest time I thought to myself “I’m just too sensitive,” as my clitoris would recoil from the slightest brush of a cutesy lil’ pink plastic vibe like a dental filling biting down on a ball of tinfoil.

Then I was benevolently gifted the rechargeable, wireless Hitachi Magic Wand. (#blessed.) This sleek beast of a toy is anything, but dainty — if the Hitachi is a grizzly bear, for example, that lil’ pink thing is a beanie baby. The Hitachi is an old-school sex toy made famous by its settings that range from Jackhammer to Jackhammer-Plus. The Magic Wand is not for the faint-of-clit. And yet, my “oh-so-sensitive body” loves it.

Though I generally like to think that I’m special, I’m certainly not in this case. It’s not that my body has changed or that my clitoris has somehow become a tougher bad-ass. It’s more that I finally understand the difference between a “buzzy” vibrator and a “rumbly” vibrator. And twat a difference it is.

This brings us to second things second: Not all vibrators are created equally. And this is especially true in the motor department. A “buzzy” vibrator versus a “rumbly” vibrator isn’t about the strength of the vibration, but the quality of it.

Most vibrators are buzzy. Cheap motors operated by batteries tend to characterize these guys, with a vibration frequency that feels like a fly buzzing in your ear or when you lightly push your lips together and hum. Clitorally, this can translate to numbness, over-intensity, one-note sensation and yes — the feeling that you might just hate vibrators. Put with the perfect bluntness sex toy blogger Hey Epiphora (heyepiphora.com) is known for: “Buzzy vibrators are a menace to society.”…continue reading…