My Unfulfilled Fantasy: Same-Sex Hookups

I've had crushes on women my entire life, but I've never gotten around to dating one.

women on a porch

When I was leaving for college, my high school friends predicted two things would occur once I fled the nest, away from my WASP-y parents: 1) I'd become a chain smoker to complete my poetry-reading, philosophy-pondering image, and 2) I'd get it on with girls. 

After four years at hippie-dippy NYU, surprisingly, neither of these predictions came true. Alas, while I still have no interest whatsoever in getting lung cancer, I do still have an interest in hooking up with girls. Except these days, I'm pretty much convinced it's never going to happen. 


If you asked me to define my sexual orientation, I would say "straight," because that's the quick answer—but the real answer is more "straight-ish." I've only dated men and had sex with men, but I've had intense crushes on women my whole life. That's not enough to say "bisexual" in my book, but enough to say "straight-ish." 

It started in 9th grade with Carly. She was my first kiss ever during a game of spin-the-bottle. To my utter surprise, she asked me to be her date to Homecoming!  One day, hanging out on her bed, talking about our dresses, my hormones were bleeping and blooping off the charts—I wanted to kiss her. But did I take Carly in my arms and plant a big lusty smooch on her? Hell, no. I was way too scared. 


Fast-forward to 11th grade when I became friends with Anne Marie, a gifted musician. We met during driver's ed class and, as two creative chicks at our preppy, lacrosse-worshiping high school, Anne Marie and I soon became inseparable besties. She was so beautiful, talented and fragile that it wasn't difficult for me to develop a crush on her. Complicating matters? She had actually been sexually assaulted once by a woman. Anne Marie told me she knew I had a crush on her, but I was waiting for her to act on it because of the whole assault thing. And she didn't.

During college, I had a reputation at the school newspaper for being a bit of a tease with the boys, but one of the reporters, an over-sized personality named Laura, did me one better. At alcohol-fueled school newspaper parties, Laura would dance with me, getting in my face and teasing that she'd kiss me. Oh, horny 14-year-old boys, I know how you feel! By this time in my life, I actually would have kissed Laura, but she'd always jerk herself away and laugh at me derisively. 

I could go on with more it-almost-happened incidents I've had with women, but I think you get the point. Despite years and years and years of being single (and kinky!), women and I just never happened.

The trouble is, for the past six months, I've been in a relationship with a guy whom I want to be my life partner. While the intimacy we have together is worth everything to me, I'm honestly a little disappointed that I never got around to being with a woman—maybe the way an old, arthritic world traveler feels when she realizes she'll never get to climb Mt. Kilimanjaro. (Not that I'm comparing p**sy to mountain-climbing or anything.) It just feels like a missed opportunity.


Now, I know what you're thinking: (as the stereotype goes) any guy would love it if I brought a woman into our bed! But I always thought I'd explore a woman's body when I was single, not as part of a couple. One, I never fantasized about doing some kind of fake lesbian thing for a man when I was pining after Carly and company. Two, I want to be with a woman, not have a threesome. Three, I want to be with a woman so I can be with a woman, not to show off for an (admittedly thrilled) audience. Four, it wouldn't be very fair to the woman if we could only get together with my guy there to watch. And five, the intimacy between my guy and me is too intense to break. That's how I feel right now, anyway, and I don't see my thoughts on the subject changing.

Yes, I'm relenting to the fact that if my single, sexually explorative days are over, women like Carly, Anne Marie and Laura will one day just be blips in my memory. No door is ever completely closed, though. Who knows what will happen?

Written by Jessica Wakeman for The Frisk.