Pushing Daddy Harder: What Being a Bisexual Sugar Baby Has Taught Me

On my first date with William, I told him I was bisexual. We were talking about our dating history over an upscale steak dinner, and, after coming out of the closet almost four years ago, my sexuality is something I refuse to hide. In response, he slowly lifted his eyes off his dinner plate and looked at me, smiling devilishly, his chin hovering over a bloody filet mignon. “Alright, that’s it,” he said. “I’m sold.”

I am a sugar baby, which means I am essentially paid to be my clients’ ideal girlfriend. In fact, I often call myself a “serial sugar baby,” because I have been dating men like William back-to-back since I was a sophomore in college (almost four years). Though I don’t have to, I often brush off strange comments about my sexuality — my job is to boost his ego, and distract him from the stress of everyday life — not second-guess him.

William and I do many of the same things I would do with a partner my own age: a typical date includes dinner, sex, and a long night of watching movies and laughing at a hotel, because we have the same taste in dumb, early-2000s comedies. I laugh and call him handsome and dress exactly how he likes, and don’t cause any problems. I get to act like a wealthy socialite, dancing around his apartment with a bottle of Dom Perignon in hand, admiring the Banksys hung on his walls. Honestly, it’s a lot of fun.

It wasn’t until he helped me move that I learned he was utterly terrified of lesbians. As we unloaded the Uhaul, he looked at my new roommates, a sweet, unassuming lesbian couple named Hope and Angela, like a pair of monsters. He wasn’t offended, but frightened, avoiding eye contact, shuffling awkwardly around them while he carried the boxes in, and letting me answer the light, conversational questions they threw his way. Luckily, they weren’t offended. But I was.

He had never asked for a threesome, or otherwise requested some sexual act that required me to be attracted to multiple genders, which had confused me for the past three months I’d known him. Instead, he nervously asked me questions about the intricacies of lesbian sex and courtship, twiddling his thumbs and avoiding eye contact, as if my liking women was a thrilling and dangerous secret. Now, I realized these were less expressions of thrill, and more the body language of fear.

When I asked him later why he acted so weird, he answered frankly. “Oh, you don’t understand, babe,” he said. “Lesbians hate straight men.”

It’s one of many comments he’s made about my queerness that have made me pause — not reconsider my decision to take up this kind of work, nor question my sexuality or sense of self-worth, but make me wonder whether I should have found a way to use them as an opportunity to educate him. Ultimately, I think his behavior originates from a fear of the unknown, but to me, it meant more. It’s at times like this where I feel a need to speak up for my queer siblings and sisters; a deep-seated anxiety gnawing away at my hard-earned sense of self worth, formed of a mantra I’ve repeated in my head for years: “educating straight, cis men about my existence is not my job.”

I represent, for William, his most intimate experience with queerness. Because of this I often put the pressure on myself to represent our whole community well, though I know queerness describes a much broader experience than just my own. According to him, none of his friends, family members, or coworkers identify as such, so he asks me the questions he feels he can’t ask anyone else.

I am his gateway to understanding this community, and yet, when I am with him, I am merely playing a part: in my day-to-day life, I wear dickies and doc martens, speak in a low, raspy tone, and date women and nonbinary people much more than I date men; with him, I wear minidresses and heels, obsess over fine jewelry, and only comment on other women’s attractiveness when he asks for my opinion. I can be ‘out’ as a bisexual woman, but have to shed the queer part, and make my behavior and appearance palatable for a straight, cis, man. Correcting him, much less getting angry about his ignorance, is not on the menu.

Unfortunately, the current dialogue we have in America about sex work makes it so I can rarely express these complicated feelings. On one hand, admitting I do sex work at all, much more that I don’t love every second of it, puts me at risk of some Nicholas Kristof-minded “rescue” mission. A concerned family member or friend could stage an intervention, or worse, let a nonprofit that claims to fight “sex trafficking” know about the hotels and Airbnbs in which I work. More common, however, is the silencing I experience in feminist and queer spaces. Admitting sex work isn’t always fun contradicts the misled narrative, mostly written by non-sex worker feminists, that sex work is always “empowering.” Unlike the waitress who loves her restaurant but hates the table she served last night, I am not allowed to vocalize any discontent with my clients. In fact, admitting that I would tolerate the ignorance of a client for money often earns me the label of “gold digger,” or “whore,” — the very same whorephobia (that some prefer to call “slut shaming,” writing out role of sex workers all together) so many modern women pretend to fight so hard against.

In reality, negotiating my sexuality in this setting is tricky, tiresome, and oftentimes, a little annoying, and I don’t think it makes me anti-feminist or anti-sex work to admit it. Yes, getting asked questions like, “do girls really scissor?” and “who’s the man in the relationship?” is infuriating, and makes me feel like I’m in the 10th grade. If I didn’t know William and he asked me just one of these questions, I would slap him across the face. I am a woman who gets angry when people insult the LGBTQ community, and it goes against every ounce of my being to resist telling him to just Google the answers to his dumb, inconsiderate questions.

But William isn’t a paypig, he’s a sugar daddy — and none of that is part of the arrangement. Instead, I find small ways to push him towards a greater understanding of our community (after I’ve secured my bag).

In the time since William made that comment about my roommates, he’s made some progress towards a less fearful perspective. He’s met them twice since, once to take them shopping for new bikes so they could avoid taking the bus to work while COVID-19 spreads — a gesture that was very well received. Though he was nervous, we have had enough difficult conversations by now for him to have a better understanding of their relationship, and act a little more normal. He’ll read short, printed passages of Gender Trouble if I give them to him doused in my own perfume, and despite his reluctance, I think some of it has gotten through.

“When you’re not with me, how do you move through the world?” he asked me one month ago, twirling a long lock from my scrunchy-fastened ponytail.

“Not like this,” I said, looking down at the bright red heels he’d just bought. He smiled bashfully back at me, and wrapped his sweater around my shoulder. I answered truthfully, from my experience, refusing to represent anyone else. He accepted that.

This time, he had to.

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Kimberly Contessa

Working woman in San Francisco.

Kimberly has written 1 article for us.


  1. Thank you. I really appreciated how you talk about navigating various pulls from professional boundaries, care about your community, personal identity, self-presentation, and more.

  2. thank you for this. i hope you continue writing about your experiences, i think encouraging folks to acknowledge the nuance that exists in sex work is so important.

  3. I am experimenting with how to try to find the courage to write comments, when finding words can be challenging for me.

    The way this article makes me feel is:


    Yeah! YEAH!!

    This writing is a warrior. She is strong and brave and inspiring. Wow she is such an articulate writer! More please.

    More please :-)

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