Exploring My Sexuality Through the Lens of Evolving Gender Identity

I’m a woman who wants to get in touch with her masculine side

I was recently teasing my brother about his attraction to women who joke that they are “lesbian-adjacent.” People like Tina Fey, for instance, who loves to poke fun at herself for not being a typical, dainty, uber-femme woman.

The conversation veered into the kind of women I like. I admit, I have a type when it comes to women — brown hair, distinctive dark eyes, well-defined lips, strong eyebrows, bosomy, and yes, uber-femme. But I told my brother I’ve been more into butch women recently.

“I have a huge crush on Abby Wambach right now,” I admitted.

He immediately lit up. “Oh my god — you mean that hot blonde soccer player? She’s at the top of my fantasy girlfriend list.”

I gave him a sympathetic look. “You do realize she’s a lesbian, right? I hate to burst your bubble, but I have more of a chance with her than you do.” (Just kidding, Glennon!)

“I know, I know,” he said. “It’s like your crush on the Queer Eye guys. You’re never gonna get any from them, but you still drool over them.”

At that point, I was determined to help him figure out what he was looking for, since clearly, moving from Tina Fey to Abby Wambach is going in the wrong direction for a hetero man. “So who else do you like?” I prompted.

He gave it some thought for a moment, then said, “Rachel Maddow,” with a definitive nod of his head. “And Sue from the British baking show.”

I started laughing as he sat there looking perplexed.

“They’re both lesbians!” I finally informed him.

He started laughing, too.

“Your chances of having sex in the future seem pretty bleak,” I joked.

I actually really admire Jack’s disinterest in gender roles and stereotypical behavior — even up to and including sexual attraction. He’s always been a very whole person and unafraid to express that. He’s 6’2”, a farmer, an engineer, a mathematician, a gamer, and a man who loves to drive really tiny manual transmission cars at very fast speeds. And also, he sends his friends boxes of homemade cookies every Christmas, crochets blankets for family members, and is the first person to tell our nephews that being kind is more important than being strong.

And he has a thing for lesbians, apparently.

I have been thinking a lot, lately, about my own wholeness, in terms of gender. I’ve always considered myself pretty whole, too, but now I suspect I was a little off in my assessment. I’ve come to believe that I’ve been neglecting my inner masculine and didn’t even know it.

And further — and all the harder to unpack— is the fact that I’m not sure I’m able to really see and experience myself beyond the gender spectrum, as I long to do.

I think women are lucky that we have so much more forgiveness about exploring our inner masculine side. It seems that in our culture, we shame men for leaning into the feminine, but with women — so long as we do it a certain way — we can lean a little into our butch side.

But there are still a lot of rules about it. You can be a tomboy — but the way Megan Fox was in Transformers. You know, the super short denim skirt and tight tank top, the sultry lean over the open hood, looking at a car’s engine… So long as you look super femme, super hot, and super sexy, you can butch out all you want.

Years ago, after ending a relationship, I shared my frustration about dating with a friend and how I wished it was easier to find a nice man who wouldn’t expect me to groom myself the way he wanted.

Her husband walked in at that point and said he was shocked.

“I thought you were a lesbian,” he said.

“Why?” I asked, thoroughly confused.

“I know you’ve dated men, but you’ve been single for a couple years now. I just figured you’d either given up on them or hadn’t come out of the closet yet.”

Oh. Of course.

There had been the faintest tinge of judgment when he’d said the word “lesbian.” I should’ve known what he was getting at.

I’d heard that before, many times. When you’re a woman who doesn’t get married to a man before 30, it’s not unusual for people to assume you are a lesbian. Apparently, some people think that sexual orientation is something you can change at will, and in response to a string of disappointing relationships.

Or if you have failed to enter heterosexual marriage by a certain point, then surely it must be because you aren’t actually hetero and maybe are too scared to admit that?

And then there’s the implication that you’re just kinda butch — a little too butch. The kind of butch that’s an insult, not a harmless adjective. As in: No self-respecting, heterosexual, masculine man would be able to love a woman like you.

The funny thing is — I do like women. I never dated any because those to whom I felt an attraction were always already in a relationship. I didn’t purposefully pursue relationships with women the way I did with men because I liked them both equally and frankly, really enjoy dick in the bedroom, and also, I’m pragmatic: I wanted kids and wouldn’t it be easier to just pursue men and get a little viable semen out of the deal?

Despite my attraction to women, I felt insulted when people said they thought I was a lesbian. I knew there was judgment underneath that. I knew there was an implication that I wasn’t femme enough.

Somehow, that made me feel like less of a woman.

As I have entered middle age, I’ve come to realize that I don’t even know what it means to be a woman. Today, if people assume I’m a lesbian, I couldn’t care less.

I guess what I’m trying to say is: I want to explore my butch side.

Yes, I feel that I am a woman.

But how I once defined “woman” no longer feels accurate to me. In fact, I feel so upended by my personal evolution of that definition that I’m not even sure it matters that I feel like a woman. Because if I don’t know what “woman” means, then what does it matter that I feel like one?

This past year, I’ve been very drawn to exploring my inner masculine. I went through a period of deep anger that I insisted on expressing — and though I’m not as angry now, I insist on continuing to express my feelings, even if they are not considered feminine, gentle, or nurturing.

I want to be more aggressive in some ways, though strategically so. I want to learn how to lay down boundaries fast and hard. I want to be able to share an opinion loudly and firmly when it’s appropriate to do so.

I’m not shaving my body hair right now. And I want to add that I’m not doing this because I want to feel more masculine by having hairy legs — in fact, I think that’s a sexist stereotype, considering the fact that women’s bodies, in general, have hairy legs, which means hairy legs are not “masculine,” but only defined as such because of our cultural biases. But back to the point: I want to challenge myself to be able to embrace my body beyond gender norms as a woman with hairy legs.

And as for sex… Not only do I long to finally find an unattached woman to whom I am attracted and hop into bed with her, but I have even started to think about sex from a male perspective. I can literally feel masculine energy building in me when I admire women that I find attractive — right there in my pelvis and the front of my hips. It’s not the usual pull of energy into my body that I feel when I think of sex with men, but rather a sharp, piercing energy that moves out of me.

Is that odd? Is it odd that I imagine not just having sex with a woman, as a woman, but I imagine what it would feel like if I had a male body, as well?

I guess what I’m saying is: I totally want to nail someone.

I don’t know what I believe about gender, anymore. Sure, we have certain parts. But not everyone falls into those perfectly binary categories. Intersex, people, for instance. Physical gender, despite some people’s insistence to the contrary, can sometimes be unclear. More than one or the other.

But what about psychological gender? Does that even exist? What if we had grown up in a world that didn’t acknowledge the differences between genitalia, other than to explain how they worked? What if there were no stereotypes to buy into or expectations to live up to?

If that were so, I feel pretty sure that I’d be more comfortable expressing myself in more masculine ways, up to and including pounding away at a lover, with or without a strap-on.

This thought both thrills me — and terrifies me. I’m terrified of the ways that I might evolve outside of our culture’s expectations of me, as a woman. I already get enough shit for that and can’t imagine dealing with more criticism that would directly target my worth as a woman.

It also terrifies me because I know I have work to do in the other direction — work to do in deprogramming myself from traditional expectations of masculinity in men. I think I’m already pretty supportive of men expressing themselves in more feminine ways, but if it was in the context of a relationship, I have a feeling I would have more work to do there in order to hold that kind of space for a man without feeling vulnerable or scared, myself.

Ultimately, I think this is an essential exploration for me at this point in my life. I spent a lot of last year challenging my perceptions of myself and allowing myself to express traditional feminine sexuality in ways I had never done before.

But now…now I want to go bigger. I want more. I want to be stuck less on woman and focus more on human being — or perhaps a more expansive identity — soul.

I think back to my conversation with my brother about his attraction to lesbians, or about all the times someone told me they thought I was a lesbian, and I realize I don’t want any of that. I want to burst past the boxes and labels and judgments.

Who knows — maybe Jack will find a wonderful bisexual woman who has typically been with women but who is impressed enough with Jack’s feminine side to choose him as a partner. And maybe we’ll someday stop expecting women to enter heterosexual marriages by a certain age and stop assuming she’s a lesbian if that doesn’t happen.

Maybe someday I won’t feel so conflicted about not shaving my legs because the way I groom myself won’t be dictated by our culture’s gender expectations. And maybe I’ll get to let my inner masculine pound a divot into my mattress in the shape of my lover’s body.

A girl (or whatever I am) can dream, can’t she?

© Yael Wolfe 2020

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