First Time For Everything: Hooking Up With A Woman


Love & Sex

Simply put, I have been boy crazy since elementary school.

Men have always been the ones I kissed, fellated, fucked, Skype-sexed, you name it. All of my sexual experiences and struggles coming to terms with my sexual kinks have involved cisgendered men.

But until recently, there was a side of myself that lay dormant so long it would probably more appropriate to call it “stagnant.” It was a side of myself that I didn’t act upon out of fear of what would happen: the one that had sexual and romantic feelings for women.

Sexual orientation is a continuum on which we vacillate. People refer to the seven-point Kinsey Scale: 0 is “exclusively heterosexual with no homosexual” feelings, 1 is “predominantly heterosexual, only incidentally homosexual,” 3 is “equally heterosexual and homosexual,” 6 is “exclusively homosexual,” and so on. The concept of the continuum made sense to me, but I never knew quite where to place myself on it, mainly because I had more desires than actual experiences. I was also aware that people can be homosexual or bisexual their entire lifetimes and never have the privilege of being able to act on it. Are these labels ascribed by fantasies? Experience? Or some combination of both?

My first kiss was actually with a girl, in 9th grade, during a game of spin-the-bottle. I later had another “first kiss” with my first boyfriend, but there was no question that Connie and her big, pillowy lips utterly enchanted me. I remember one afternoon, I hung out at her house after school and we sat in her bedroom, on her bed. All I wanted to do was kiss her, but I was afraid of what would happen if she didn’t like it. Later in high school, I crushed hard on a friend named Abbie. Abbie and I never discussed my feelings for her, but my boyfriend at the time told me that Abbie had said him she knew I had a crush on her. Knowing she was gossiping behind my back about my feelings for her to my boyfriend only made  me feel shamed by both of them.

In college, I crushed on this cute French girl whom I studied abroad with in Prague. Again, I didn’t act on my feelings. In the past several years post-college, I’ve mostly developed sexual feelings for girl friends. I asked a close girl friend to have a threesome with a boyfriend and me; it wasn’t so much that I wanted a threesome, but I wanted to hook up with her. She declined and I was back at square one. For years and years, I had sex dreams and fantasized about both cis and trans women. I sometimes felt flirtatious sexual tension around out women, which I ignored. All of this felt especially confusing because my best friend is an out and proud lesbian, as are many of her close friends. I didn’t feel any social pressure by anyone specific not to explore my sexual feelings for women. Yet my actual experience with women, save that one high school kiss with Connie, amounted to nothing.

So, because I hadn’t actually been with any women, I considered myself heterosexual. First of all, I was preoccupied well-enough with my conflicted feelings about being a sexual submissive and a feminist. I had put so much effort into exploring my kinks, both emotionally and physically, that it was easy to put the attraction-to-ladies stuff on the back burner. As a result, so much of how I thought of the construct of my sexuality pertained to the patriarchy and men.

Secondly, it simply didn’t feel right to claim to be bi when I had done nothing more than briefly peck another woman’s lips 12 years ago during a party game. Bisexuals and gays face real discrimination, real hatred, real injustice — it didn’t feel respectful to that reality to call myself “bisexual,” too. If asked, I referred to myself as “straight-ish” or “mostly straight.”

For someone who was out — loudly, almost obnoxiously out — about my BDSM kinks, I kept the bicuriousity mostly closeted. I mean, I talked about BDSM on Ryan Seacrest’s radio show! Yet I was still afraid to act on my feelings for women because of the risk. Most of the ladies I had crushed on were platonic girl friends. What if I didn’t know how to read cues? How weird would our friendship become if I tried to kiss them and was rejected? What if I lost friendships over it?

Coincidentally enough, the night before I first had experiences with women, I met up with a bunch of friends at a lesbian bar. I arrived first and was sitting alone, drinking a cocktail. An extremely pretty woman sat down across from me and started chatting, as it was clear both of us were waiting for friends to meet us. But wary that she might be flirting, I made it clear that I just happened to be in a lesbian bar waiting for my friends, telling her at the first opportunity, “Oh, I’m not gay.” She may have just been trying to be friendly, but I shut it down. The conversation petered out shortly afterwards and I kicked myself, not just for being socially awkward but for bungling what could have been an opportunity. She was really, really cute. It really, really unnerved me. It’s difficult for me to even put into words how confused that felt.

The very next evening — no doubt spurred by all these scattered feelings — I had my first sexual experiences with women. The first woman I actually hooked up with was a cute, out bisexual friend. We were at a party in her house and I stumbled upon her in her bedroom.

“What do you want to do?” she asked me.

“Um, I really want to make out with you,” I told her, tentatively, “but only if you want to. I don’t want it to make our friendship weird.”

I am really romantic, you guys.

“I’m OK with it if you’re okay with it,” she told me. That was all I needed to hear. “Come,” she said, and led me to her bed.

I lay down and she climbed on top of me and we had this pivotal moment — for me, anyway — of kissing and running my hands all over her body. I put my hands in her hair, gently tugging like I enjoy men doing to me. I touched her breasts with my hands and tongue. I felt her butt and her arms and her legs and explored all of these places trying not to fumble like the adolescent I felt myself to be. It felt strange for me at first: for 14 years, I’ve only touched men’s bodies, men’s muscles, men’s genitalia. Women’s bodies are so different from men’s bodies, I realized. I’m a different person in bed with a woman than I am with a man. But the intensity of sexual desire felt so much the same. And the longing I felt for her and her body after we parted that night felt so much the same, too.

I don’t know if she wants to be with me again, or how I would even go about making that happen. I thought about her all weekend — dare I invite her over to come watch movies with me in my bed? And yet, I didn’t. I wish I could say finally hooking up with women quelled my multitude of confusions. The truth is only thing it clarified is “yes, I do like this.” The reality is in the hours and days afterward, I felt even more confused about what my next steps would be, if anything, in further exploring this neglected part of my sexuality. I had all kinds of questions it felt like I needed to answer: Does this mean I’m formally “bisexual” now? Do I want to tell my friends and family about this? Do I want to date women?

I don’t know the answers to any of these questions. I also know I don’t have to know right now. Maybe my first time with a woman doesn’t have to mean anything. Maybe it just was what it was — a beautiful and meaningful experience with a cisgendered woman whom I like very much. Labels can be helpful, but they can also be reductive. Those are not necessarily the most detailed descriptors of our selves and perhaps not what I should be chasing down to quell my confusion.

I hope for the right person — whoever he, or she, might be — none of that will matter.


Original by Jessica Wakeman

Leave a Reply

Your email address will not be published. Required fields are marked *