How I Blew Up My Reverse Pretty Woman Arrangement

·6 min read
Courtesy Rachel Krantz
Courtesy Rachel Krantz

In 2017, I was two years into my first open and Dom/sub relationship. It was a fraught and frequently stoned time in my life. On the one hand, I’d come into my queerness and was having the kind of sexual and romantic adventures I’d previously only fantasized about. On the other, my primary partnership with a man named Adam was increasingly characterized by gaslighting and jealousy.

I’d recently formed an intense text-based friendship with Adam’s long-distance girlfriend, Leah, and was steeling myself for her week-long visit to Los Angeles for Adam’s birthday. I felt a pressure to be a “cool polyam girl”—to be “good” at non-monogamy, and to have just as much of my own shit going on. Which indeed, I made sure I did.

Below is a chapter from my forthcoming reported memoir, Open, called “Reverse Pretty Woman.” It tells the story of my time dating a sugar daddy during this period. Like many experiences in the book, it exemplifies the seemingly conflicting ways in which I found myself feeling both increasingly sexually liberated—and yet also more under the thumb of patriarchal standards than ever before.

Adapted from OPEN: An Uncensored Memoir of Love, Liberation, and Non-Monogamy, copyright © 2022 by Rachel Krantz. Used by permission of Harmony Books, an imprint of Random House, a division of Penguin Random House LLC, New York. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

Summer 2017 — Los Angeles

I met Silas on OkCupid. His profile made it clear he was non-monogamous, with a primary partner. At 46, he was older than anyone I’d ever gone out with, but I liked the fact that we were in similar relationships. (I hadn’t had much luck with being interested in anyone else who identified as non-monogamous besides the woman I’d been dating, Miranda.) I felt a little starstruck and flattered when I realized who he was. He wasn’t famous, but his businesses were.

“I don’t have time to play games, and I’m not looking for someone to see more than once a week.” He smiled over our 15-dollar rice bowls. He was so forthcoming for a first date that it was actually refreshing. “My current girlfriend was my secondary partner for many years, until my wife and I got divorced. She’s not possessive and really likes to share me. She’s the one who actually encouraged me to get back on OkCupid. She thinks it’ll keep things healthy between us. But I don’t have much time, and I’m not into sleeping around casually. I’d like someone steady, no drama.”

“I’m looking for something similar,” I replied. “Wonderful,” he said, and smiled conclusively. “I have to get back to work, but I enjoyed meeting you. Can I take you to dinner next week?” I felt like I’d passed the first round of a job interview.

Sugar Babies on Guys Like Gaetz: ‘They Don’t Think They’re Paying for Sex’

After our second date, Silas revealed more clearly that he was also into Daddy/little girl dynamics, with a financial component. I appreciated the fact that non-monogamy was helping me be more open to different types of relationships, less judgmental. Having a sugar daddy was something I’d never allowed myself to consider while auditioning “the One.” Weren’t those guys just buying the girlfriend experience and calling it something else? But it turned out even the idea of being kept that way turned me on, and now I felt free to explore that. I’d never even gone out with a man who regularly paid for dinner. (Adam always threw down the card, but it was our joint account.) How had I never considered that the Interesting Conversation in a Tight Package Services I offered could be compensated beyond bike repair and furniture assembly? I felt duped by my conditioning, like realizing thick brows are in after a lifetime of over-tweezing. I’m already almost 30—my best years and brow hairs are behind me! I will appreciate my still perky(ish) tits and get wise.

Silas asked for my shoe, bra, and clothing sizes; my favorite brands and foods, vacation destinations I’d like to explore. He told me that whether I replied or not, I would begin receiving things that week. He signed his email “Daddy.” As promised, bags of gourmet groceries showed up at our door, along with the second air conditioner Adam had said we could do without. Ethically made lingerie and shoes. An adult-sized baby onesie that read “I ♥ Daddy.” Adam and I had a good laugh over that one—and then he threw me on the bed. Was it my imagination, or was he suddenly treating me with a little more respect, too?

When I eventually went over to Silas’s house, I felt like I was in a movie. I’d never touched this level of privileged-white-male wealth so intimately. There was a big, long mirror across from us in bed, and as I looked at us having sex I enjoyed the distinct satisfaction of an overachiever. I was desired. So desired that someone not unattractive might even indirectly pay to do this with me.

7/29/17 — Journal Entry

I’ve been rehearsing for this role my whole life.

[Silas] choking me [but] didn’t want to send me back first time with marks

‘are you my little fuck hole?’ and I farted and tried to pass it off as a queef, am I a whore now?

…[Adam] proposed sort of, ‘I’ve been thinking about this I would marry you’ and I looked him in the eyes, and I couldn’t say yes

These kinds of half-proposals from Adam were common whenever new sperm competition was in the mix. I didn’t really take them seriously by this point; I didn’t feel they “counted” as sincere, though looking back I’m not exactly sure why. Mostly, I just felt smug instead—and annoyed the stigma around sex work had made me miss this potential revenue-and-confidence stream until now. No more. I have to stop giving away my time and body for free unless the person really deserves it. Adam is lucky, I thought, briefly regaining my male-validation-dependent “self-esteem.” Yeah, that’s right, I said it. Lucky motherfucker, to be with me.

Considering I’d also started dating a German filmmaker I was waiting to sleep with, I felt I was in excellent shape ahead of my metamour Leah’s impending visit. Silas and I talked about getting me a hotel room close to where he’d be vacationing with his kids that week. But as Leah’s visit drew closer, Silas still hadn’t booked the room. And was it just me, or was he being a little less doting ever since we slept together? I began to spiral. To believe I’d been used and that my value was now diminished for having entwined sex with materialism.

My increasing nervousness over Leah’s visit morphed into a growing compulsion to test Silas. I knew I was being bratty, but I needed him to come through and distract me, faster, harder. For the high he provided to be as heightened as possible. I needed this now-constant cloud of generalized anxiety hovering over me to be worth it. I knew naming my feelings would likely provoke him to the point of rejecting me. That part of what Silas was “compensating” was an implicit promise to ask of him no emotional labor. Yes, I saw what I was doing as I hit send on the email. I was confirming my fear that I was like my mother, provoking rejection as a form of self-sabotage. And in so doing, I was also reaffirming that Adam was right to try to change me.

From: Rachel to [Silas] — Subject: Dear Daddy

…I felt a bit like a call girl to sleep with you and not hear anything sweet from you for a few days… but I somehow felt I owed it to you after everything you’ve given me. Don’t get me wrong—I wanted to give it to you—but… [m]y coming back with an ask for something concrete [the hotel room] was an attempt to regain some power, to assert my value, to say I will not be taken for granted.

Silas wrote back that he was “horrified” by my implication he would ever pay for sex. He never wanted to see me again.

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