The 36-Year-Old Virgin

A sweet coming-of-middle-age sex documentary…

Skyler was too busy saving sex for marriage to try out standard heterosexual practices like penis in vagina sex during his youth as a bible-thumping teenage girl, and he had no interest in the act in his man-hating lesbian feminist 20’s. Now 36, transgender and pumped full of male hormones, he has all kinds of kinky queer sexual experiences behind him, but he feels he’s missed out on something and he’s curious to try that standard act of being penetrated by a cisgendered man.

He makes a date for the big day with Bishop Black, a trusted member of Berlin’s porn community whose heart is as big as his sex drive. Skyler also invites his close friend, veteran porn performer and sex educator Sadie Lune to be his sex dula, walking him through the process and literally holding his hand.

Drawing on the wisdom and support of his queer community, Skyler chats with some friends, who share their first-time sex stories and penetration tips with him in heart-warming, insightful and often hilarious bedside conversations.

The 36-year-old Virgin was more than a film. It was a personal process for me as a repressed christian woman growing up saving sex for marriage, who then became a “gold star” lesbian repressing her curiosity about penises for the sake of maintaining an identity to someone who could relax into the fluidity of gender and begin to explore desire.

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