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Julie Wants My Ass!: My First Lesbian Experience with My Best Friend. A Tale of Lesbian Seduction

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When I kissed Lynette goodbye at our appropriately miserable reentry to the real world — Pennsylvania Station in Manhattan — I still wasn’t exactly sure what the hell I was supposed to do next. I would try to separate my feelings for Lynette from my feelings about wanting someone or something different in general — out of a desperate desire to feel some sort of control over my choices — and concede that was pretty much impossible. I settle for some Kelly Clarkson, and after my screechy but enthusiastic rendition of “Since U Been Gone,” five (!) different women approach me, complimenting my performance. One of them tells me her friend thinks I’m really cute, and could she buy me a drink? I was scared of so many things, and worried about, as usual, lesbian stereotypes — moving too fast, feeling too much. And I said so. It was one of our talents that week: saying absolutely everything that was on our minds, and processing until we felt we couldn’t possibly process anymore — at least, of course, until the next night. I planned to meet Dana in the ship lobby that morning so that we could wander around for a while before the event. When we set off into town together, she gently informed me that my whatever-it-was with Lynette had not gone unnoticed by the staff, who’d encouraged Dana to encourage me to spend more time speaking with other people and reporting on the ship’s endless entertainment options.

It sounds shallow to imply that, in the beginning, I fell for her simply because of her style, her stuff. But what attracted me was the care and attention to detail she demonstrated via a lifetime’s accumulation and curation of these things. Together they made up the way she wanted to be seen in the public eye, the way she wanted to move through the world. She was not a boy but a full-grown butch who, at 53, was confident in who she was and what she wanted. I was captivated by what Eileen Myles told me at the time: “I know how to fight for what I want, to say no, when to wait. I’ve been in time for 65 years. I have a lot to share. That supposedly should only be in my teaching life — that’s not the case. It’s amazing on both sides to be able to share the world from different angles. It’s lively. It’s hot.”If you have masturbated and spent time exploring your own body, use the knowledge you have gained of what feels good to direct your partner. I would feel horrible, hurting a person I cared for, even though I was certain they wouldn’t be able to care for me in the years ahead in the way I needed them to — someone who I suspected, ultimately, wanted different things. How do you justify leaving a perfectly nice relationship, taking a blind chance that there might be something better for you out there — even if you’re right? At the Gen O meetup, the hairdresser mentioned that most of the paying customers on board are older women who’ve had an extraordinarily difficult time navigating life as lesbians; they deserve a space, she said, to fully be themselves. Maybe Olivia could do a specific queer-plus trip for trans people and gay men? Being in a space with “someone who looks like a man,” she said — horrifying me, Jamie, Matie, Dana, and a bunch of others — “can cause these women so much trauma.” By this point, I was — somewhat unintentionally — quite drunk. We started making out (I was still peeing) and almost right away, I began writing a goofy story about it in my head, thinking about how I’d relay the anecdote to my friends (“So I had sex in the bathroom of a catamaran???”). But there was another part of me that was very much not into it, especially when the makeout gave way to other things and people started banging on the bathroom door. I would sleep in Alia’s bed that night and accidentally pat her butt in my sleep, my mind clearly deluding my body into believing I was still on the cruise with Lynette. Alia would very nicely not be weird about it.

She’s a true Pisces — romantic and dreamy and always processing. (My Capricorn groundedness makes us a good match, allegedly.) She’s known she was gay since she was 5 years old. Her mom still prays that, someday, she’ll find herself a good man. When I first pitched this story to my editors, I thought I’d be reporting on a lesbian cultural artifact in its twilight years. The women who’ve faithfully gone on dozens of Olivia trips over the decades are getting older, and I didn’t have a lot of faith that younger queer people were going to step in and save companies like this from extinction. Other elements of lesbian culture have been steadily dying; why should Olivia be any different?Afterward, I had lunch with Dana and some of the other Olivia staffers and asked them about it — why not make the Public Posts more prominent, MichFest style? Especially since the younger people at the first Gen O event had explicitly asked for more sex content. Olivia had run sexuality and intimacy workshops before, and at the lunch, the staffers floated the definite possibility that they will again. I know for a fact that a lot of my queer friends would be way more likely to book a future Olivia cruise, uncool as cruises might be to cash-strapped millennials, if they knew how likely they’d be to get some action. There are many harmful myths surrounding vulva-to-vulva sex that are steeped in ignorance, homophobia and stereotypes that it is important to unlearn. However, when both the poop flood and urine stream had ceased, she recollected herself. “What was that for?” she asked, obnoxiously.

The first time I thought that Olivia might actually stand a chance at survival was Sunday, the first full day of the cruise, when I attended the welcome mixer for “Generation O,” which is how Olivia refers to its precious few millennial and Generation X clientele. As I walked around the ship, which holds over 2,000 passengers, it was already clear that the average woman here was a couple decades older than me. But it turned out that there were a few other twenty- and thirtysomethings who’d managed to find their way to Olivia. Then somehow, all of a sudden, years passed. We became two professionals in our late twenties, living in our dream apartment on the top floor of a Brooklyn brownstone. We weren’t allowed to have pets, but, like good millennials, we had plenty of plants, and interests outside of each other: my roller derby, their ultramarathons. We were busy, stable. Happy enough.

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I would tell my partner that I cared about them deeply, and the past five years were among the best of my life. I wouldn’t trade them for anything. But I also felt like we had come to a crossroads, and we weren’t facing the same futures. I had tried so hard to see myself in their dreams, but now I was having dreams of my own. And I didn’t think I saw a future, even a part-time one, in Montana.

I was the one who seemed to stress this rule the most. I warned my partner about it all the time: Don’t leave me. But they were confident that they’d always love only me; with other people, they assured me, it would only ever just be sex. A couple days later — after getting my serious lesbian conversations out of the way — I was about 14 rum punches deep and drunk-dancing on a catamaran. So Hannah lay on the bathroom floor as Ginny directed, and the redhead sat on her beloved’s lips. Immediately a fart emerged from her anus, followed by a second. In the spirit of lesbian camp bonding, I told my new crew about my situation — nonmonogamous, not sure how to feel about it — which seemed to pique the interest of beer bathing suit girl, because she would soon afterward follow me into the impossibly tiny bathroom, bursting in on me mid-pee. I tried to tell myself that lesbian bed death isn’t real, all the while heartily blaming myself for our increasingly diminished sex life. I was the one who never really felt like initiating, or at least not with anywhere near the regularity we’d had as a hormone-crazed new couple. I assumed, at best, that all passions cool somewhat over the years; at worst, I thought something might be wrong with me.

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I would move out of an apartment that I adored, that I’d almost single-handedly furnished, that I thought I’d live in for years to come. I would hug my landlady, crying again because she was crying for me. There’s no safety net in porn. Shaw, a veteran of the business and someone who commands a higher price for her anal scenes — something that’s not true of all the women who perform this act — says that she’s heard of women tearing their anuses or developing fissures. And there’s no worker’s comp on the set. The industry demands more and more of its performers without medical help. When asked about what she could do in the event of an injury, Shaw said this to Vice: “No one ever talks about that. They make you sign waivers before you do these scenes. You’re absolutely not going to get workers’ comp.” We all formed one big circle, and the staffers got the ball rolling. First things first: How had we all heard about Olivia? Later, when telling friends what had happened, I did laugh about it — one told me it sounded like something pulled straight out of The L Word, which, true — but I was also a little mad at that girl, and even more so at myself for being so sloppy. The consent element there was indeterminate; I had willingly gone along with the hookup, at least for a little while, though I remain uncertain about how much I really could have consented while drunk-peeing in a bathroom the size of a broom closet. That night, Matie and Jamie convinced me (against my natural inclination to avoid live entertainment) to go to the evening’s scheduled attraction, a comedy set by Elvira Kurt. Before Elvira performed we were welcomed by Tisha, Olivia’s VP and our cruise director, who greeted the “ladies of Olivia” and announced a few of the events coming up over the next few days, including a meetup for the “Older, Wiser Lesbians,” or “OWLs.” (“Date me, OWLs!” Matie whisper-yelled next to me.)

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