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That watching thing has largely been my path even now,” he says. Even as a teen in Detroit he says he struggled to get in with the other discreetly gay high-schoolers. Jackson, who describes himself as “an outsider’s outsider’s outsider,” is constitutionally wary of being on the inside. “Thank you,” he said politely in response to their oversharing, again and again, to which they’d usually respond, “No, thank you.” “I’m still processing …”, “As a queer writer …”, “I’m happy, and I am who I am …”, I overheard them saying, several wiping away tears or holding their hands over their hearts. Right before we met, I’d been standing outside of the Lyceum Theatre across the street, watching Jackson hold court for his fans - on this night, mostly queer teens in Docs and T-shirts that read things like “Unapologetically Black,” all hoping to snap a selfie with Jackson or ask him to sign their Playbill. Jackson is 41, and right now there are different priorities.Ī Strange Loop’s Usher is in his 20s, and like many a baby-faced NYU graduate is haunted by self-doubt and self-hatred (literally - the rest of the cast is comprised of six “Thoughts,” all nagging voices in Usher’s head that represent everything from “Sexual Ambivalence” to “Daily Self-Loathing”), trapped between his homophobic family whose only understanding of what he could or should be doing was what Tyler Perry does, and a “white gaytriarchy” that he feels both sexually enthralled and belittled by. But he has his excuses: He got ghosted shortly before the pandemic, and a tarot-card reader in Florida recently told him he shouldn’t get laid until June. Add to that: He’s a fabulously talented and successful gay living in New York and working in what has to be one of its highest-gay-headcount industries, the musical (this particular musical attracted quite a few A-list producers, including RuPaul, Billy Porter, Jennifer Hudson, and Mindy Kaling). “You’re a young gay living in the big city!” Usher’s doctor scolds (when he admits, shyly, “I average one penetration a year”), which is essentially what I tell Jackson myself.
A Strange Loop, which won the 2020 Pulitzer Prize for Drama - “I was surprised that they made the right choice,” Jackson says - opens with the promise that “There will be butt-fucking!” And its young, fat, queer, Black theater-queen aspiring-playwright protagonist, Usher (yes, he works as an usher), who’s writing a musical (yes, called A Strange Loop), certainly wants to have gay sex and feels like something is wrong with him for not having it, but the promised butt-fucking, when it appears, is not something anybody wants. Obviously he’s hoping the ticket buyers for Broadway musicals, who trend white, heterosexual, and in from out of town, are at least … curious.
“Where’s the counterculture? Where’s the danger? Where’s the excitement? Like, to say, ‘I’m gay. It’s just a few nights before his “Big Black Queer Ass American Broadway Show,” A Strange Loop, was to open across the street at the Lyceum Theater, and though the musical is maybe the gayest thing I’ve ever seen on Broadway, Jackson has clearly not spent much time lately on the gay nightlife circuit.
Jackson asks me, picking at a bowl of unusually orange bang bang shrimp at the nearly deserted Bobby Van’s Steakhouse on 45th Street. “I’ve been having this ongoing debate with myself. Jackson on opening night of A Strange Loop.