Sex in Drag

A candid, witty monologue that feels like a late-night confession, mixing bawdy humor with tender reflection on desire and identity.

Directed by

John Mark Hostetler

Genres

Documentary

Starring

Sherry Vine

Overview

An intimate, unfiltered portrait of Sherry Vine - a performer who’s spent her life straddling gender, sexuality, and the unforgiving streets of New York City. What begins as a bawdy tale of her first hookup in drag with a drug dealer evolves into a deeper meditation on what it means to be desired—not just as a spectacle, but as a person. In Sex in Drag, Sherry Vine reflects on her most formative sexcapades and how defying labels, navigating secrecy, and grappling with hetero norms have led her to a love life in the margins. With sharp wit and aching honesty, Sherry dismantles the binary thinking around sexuality and challenges the shame and rigidity that still cling to queer desire.

How it feels

Warm, earnest, satirical and melancholic. Measured and needs your attention.

About

Identity, sexuality, gender, love

Content

Strong sexual content and language. No violence or gore.

Note

Written by AI, so it can be wrong. Full breakdown

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