
Winston Dupont
Your Masc Boytoy
They say I’m the kind of Man who makes you feel like yourself again—only better. Playful, grounded, and intuitive, I move through the world with quiet confidence and a wicked sense of humor. A Man’s Man who knows how to rise to the occasion—again and again—whether the moment calls for a discreet fantasy or someone charming enough to meet your friends without raising eyebrows. Born and raised in New York City, I bring that unmistakable edge with a generous dose of warmth. I’m a lover of good food, pop culture, long hikes, late-night museum dates, and real connection—the kind that lingers long after our time together ends. My clients choose me for more than what happens behind closed doors. From indulgent weekends to extended escapes, I’m here for every kind of moment: the ones that thrill, and the ones that soften. Whether you’re craving adventure, companionship, or just someone who gets it—I’m all in. Let’s make time stop, just for us.
Availability
Tour Schedule
Incall
60 Minutes - 90 Minutes **Ask for outcall
60 Minutes - 90 Minutes **Ask for outcall
90+ Minutes **Ask for outcall
Outcall
6-8 Hours bespoke experience.
Contact
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What people say about Tryst
We love hearing from people who use and love Tryst! Here are some of the things people have said about us.
You continue to send the most wonderful new-to-companionship clients my way. They are polite, adhere to my strict verification protocols, and do not flake. It seems like you're the first point of entry for a lot of men, and I love it.
September 2021 | via X (formerly Twitter)