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The Brilliant ‘Disruptive Faggotry’ of Cakeboy Magazine

‘I’m going to talk about sex and cumming and fingering myself and shaving my asshole. I’m going to own that, and I’m going to put it out there, because fuck you.’

Cakeboy is a gay men’s magazine that isn’t “gay” or “male,” according to its founder Sean Santiago, who chooses not to use those words to describe himself either. Rather, he considers Cakeboy’s identity, like his own, to be more of an ever-evolving conversation — a collaborative gesture toward something better. Or in more provocative terms, a “breeding ground for disruptive faggotry,” according to Cakeboy’s About page, that’s “like the liner notes from an imagined Amanda Bynes album dedicated to queer love.”

The seventh issue of the now three-year-old print magazine debuted this month, featuring stories about a queer photographer traveling throughout Europe taking decidedly strange portraits; four trans men competing in a bodybuilding competition in Atlanta; edible “rump scrubs” that transform ass eating into French vanilla lattes; and a conversation about beauty, coolness and sex appeal with Lady Gaga’s stylist and the reigning champ of RuPaul’s Drag Race.

I recently spoke with Santiago about the meaning of name Cakeboy, the empowerment that comes with becoming more familiar with your asshole and why being yourself in the most intentional way possible is your best identity.

You borrowed the name of the magazine from Clueless, in which a gay man is euphemistically referred to as a “Cakeboy,” or a “disco-dancing, Oscar Wilde–reading, Streisand-ticket-holding Friend of Dorothy.” Why?Because it’s a prescriptive definition of what female sexuality and gay identity was in the 1990s when I was growing up. I remember my mom and I were watching The Next Best Thing with Madonna and Rupert Everett. He has an outrageous song-and-dance moment singing that Judy Garland song “Clang Clang Clang Went the Trolley.” I was 10-years-old and remember thinking, Great, now my mom thinks this is what gay is. I don’t get to control that narrative. The notion of “gay” is a one-dimensional reduction, which is the opposite of who our reader is. Cakeboy is about reclaiming that identity, expanding outdated definitions and being who you are on your own terms.

So is there a general description of your reader?
No. There’s certainly queerness at play, and different ways of expression. If you look at every issue together, you’ll see an evolution in the scope of voices. The point is it’s not just one narrative or point-of-view, because it’s not just one reader. It’s about everyone coming together to look at things through a certain lens and expanding the definitions we have at our disposal.

Why did you choose to make it a print magazine in a digital world?
Because the reader can slowly work through it and see where the different narratives overlap and where they diverge. It’s also nice to have a space that’s not owned by Mark Zuckerberg or tech bros bottlenecking our distribution channel. These stories take up space in the real world in a way that’s impactful. They benefit from the way images can work with the text in a more dynamic way off of a screen. It’s an art project about disengaging and creating a moment of friction between different narratives where people can interrogate what they’re reading a little more.

And a way to bypass our robotic overlords?
The impetus wasn’t to spite Facebook, but yes, Facebook owns the internet and it’s a very corporate space now. Especially with regards to SEO, I don’t want my writers writing an intro graph that’s loaded with keywords so it can appear higher in a Google search. But more largely, we have a fucking terrorist in the White House who is trying to kill us all, so there’s definitely more of an anti-capitalist, anti-corporate sentiment.

We started right at the downfall of American democracy, and we’re trying to figure out what that’s gonna look like. We have the privilege of having conversations and starting dialogues in a space that’s offline and disconnected from distribution systems that we don’t own. We think about that a lot. Now more than ever, it’s important to consider how you’re getting in front of people, and how much independence you will have.

Who are we? What are we saying? What are we doing? And where can we do that? When we post on Instagram, there’s stuff we know will perform and there’s stuff we know won’t perform. But I refuse to make work only to fit that. It drives me crazy that someone else is determining if something is good or bad. And it’s not even your own audience, which is what’s so disgusting about it.

How do you feel gay masculinity has typically been represented in the media?
I don’t know that I have an answer for that. I don’t know that Cakeboy is talking to or about men. It’s really about engaging with identity at some fundamental level. And yes, there’s definitely gay masculinity that comes up and is part of the conversation. But I don’t think the goal of the project is to deconstruct what came before per se.

Okay, but the comparison to traditional gay publications like the Advocate is unavoidable, no?
Gay media has changed in a dramatic way over the last three to five years. Conde Nast and Grindr are now big corporate players in this space. Honestly, I never read the Advocate; I never read Out. I don’t actually know anyone who did either. I never really saw or heard what I needed from existing gay media. What I was really inspired by were queer women’s publications like Girls Like Us based in the Netherlands, which was such a game changer. I thought, Let’s try to figure out how to start a similar conversation in indie publishing, in the states, in Brooklyn. I wanted to bring something that put queerness forward first and looked at who you are and how you express that before caring about who you sleep with.

Photographed by Dorian Ulises López Macías for ‘Cakeboy’ 04.

While departing from various constructs — gender as a construct, masculinity as a construct, even men’s magazines as a construct?
Yeah. Initially I toyed with the idea of playing with a men’s magazine framework, but I didn’t read GQ as much as I read Vogue.

Your last issue had a piece about coordinated cumming and how nobody ever teaches men how, when and where to cum — except for porn, which has created a feedback loop between representation and reality. Essentially then, we may need to find other ways to teach each other how to cum. How much of Cakeboy is meant to be educational?
None of it is supposed to be explicitly educational, especially when it comes to talking about sex. Rather, we provide space for people to have a dialogue. Sex is never the lens. We just provide space for our writers, our contributors and our subjects to run with whatever the conversation is.

In the fourth issue you printed an illustrated guide to shooting your own asshole. The current issue begins by featuring products designed to improve ass eating. Is that about sex? Body image? Expression?
Taken as a whole, so to speak, our coverage of ass is something that’s generally meant to be empowering. I don’t necessarily look at sex as a binary, as tops and bottoms or whatever. A lot of it is just opening up and getting more familiar with our assholes. Like that scene in Sex and the City when Charlotte first looked at her vagina. There’s a certain kind of intimacy and ownership over something like that.

Why don’t you think more men wear makeup? Is it the notion that makeup “is” or “isn’t” for certain people?
With regards to men, there’s such value to a gym membership, but none to a Sephora membership. I don’t like sports, but I love going into Sephora and doing my makeup. Grindr is literally just torsos, so what value would makeup bring? That’s partly why Cakeboy can exist without a ton of pecs and headless torsos. But you do get a good lip moment.

Your website says that Cakeboy is all about “redefining and reclaiming your queer self on your own terms, away from the prying, prescriptive gaze of the salmon-chino-clad heterosexual.” The first image that came to mind was Brett Kavanaugh. Why do you think that Cakeboy’s alternative to this American hetero archetype is so important right now?
Trump is still president. That guy is likely gonna end up on the Supreme Court and strip women of all their rights. There’s a newfound sense of needing to be visible, needing to have this dialogue and these conversations — and not for someone else’s approval either.

To be yourself is so important now. And not in the stupid trite way, like, “Yeah, live it!” But to really take up space in an intentional way and to say, “Sorry, I don’t have time for straight nonsense. I don’t have time for marriage. I don’t have time for these constructs of your life.” I’m going to wear a T-shirt that says, “Bad boys have good dick.” I’m going to talk about sex and cumming and fingering myself and shaving my asshole. I’m going to own that, and I’m going to put it out there, because fuck you, I don’t owe you anything.

I don’t think there’s a reason to fold up or fold in on yourself. I think being out there and putting it all out there is very important. That’s why all the ways we activate the brand is in your face — organizing, being physically on bookshelves, being a tool that people can use to reinforce their values that are outside of constructed norms. That’s really what we’re supposed to be doing at the end of the day.