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Kyle Kupres, 25

Queer performance artist gender-fucks with Hemingway.
By Jake Malooley |

410 N Michigan Avenue

What are you up to?
I’m in town from New York visiting friends before I go do two performances in Madison and Minneapolis.

What do you perform?
I do very queer, experimental theater things. The next project is this queer reinterpretation of Old Man and the Sea. We’re doing it as Old Queen and the Sea. I play this drag-queen character who’s at the end of her performance career, so she decides to set off to sea in a bathtub. 

Do you think Hemingway would approve?
Whatever, fuck Hemingway! That misogynistic, alcoholic son of a bitch!

What’s the thrill of drag?
Well, I most often do what is called gender-fuck drag, where you take the most extreme signifiers of whatever genders and mash them together: a beard with crazy makeup, hairy legs and high heels.

And you make money doing that?
That and I also do porn.

What titles can we see you in?
Uh, Sex Addict or Lust or Pounded. [Laughs]

Is sex on camera enjoyable or like work?
Depends. Gay-for-pay men—straight men who do gay porn because it’s more lucrative—are a pain in the ass. They can’t keep it up, so they’re constantly having to go jerk off to straight porn.

How do you keep it up?
Viagra! [Laughs]

Is your mom okay with your lifestyle?
Oh, yeah. When I first came out I can remember her saying, “Oh, it’s fine with me, but I just think your life is going to be more difficult.” But it’s been the opposite. I think straight men have it bad. They feel pressure to behave in certain ways because of a box constructed for straight men to live in. Meanwhile, I can wear high heels or a fur coat on the street and there’s nothing anyone can say to make me feel less about myself.

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