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Winning My Virginity

On a trip to South Korea, 25-year-old Shelby meets Jack and confides in him her secret. When he offers to try to take her virginity – after years of battling the pain, shame and fear of vaginismus – will Shelby finally achieve what she believed was impossible?

Winning My Virginity is a twelve-minute animated film that tells the story of Shelby’s life-changing trip to South Korea, where she learns what amazing things can happen with a little bit of patience, confidence, and chance. Though the purpose of her trip is to attend her friends’ wedding and explore everything Korea has to offer, she ends up with a lot more experience than she expected: having sex, for the first time, with a man she has just met. After years of battling vaginismus, a pelvic floor condition where the muscles in and around her vagina involuntarily contract, she never thought it would happen. Men wouldn’t give her the time of day, her body wouldn’t listen to what her mind knew it wanted. So was it meeting Jack that turned the tables? Or was it traveling to the other side of the world, throwing caution to the wind, and meeting a new version of herself? Winning My Virginity will be a flirty, funny, and sweet sex-positive film about being brave, vulnerable, and 100% completely true to yourself.

Winning My Virginity is the sequel to Shelby Hadden’s short film, Tightly Wound, about her experience with pelvic floor dysfunction.

Associated Members

Shelby Hadden, Director


We are grateful for the generous support of our sponsors:

Massachusetts Cultural Council
Lowel Cultural Council
Cabot Family Charitable Trust
Liberty Mutual Foundation
City of Boston Arts and Culture