Gender Bending

Dan Savage Reminisces About Having Sex With An 18-Year-Old Cross-Dresser

Webby Awards

Long before he found his way into mainstream America with the It Gets Better project, Dan Savage was known for his shock value, and his latest story is a doozy.

On the latest episode of the Risk podcast, which specializes in having people tell stories “they never thought they’d dare to share in public,” Dan shared about an encounter he had with a “gorgeous” 18-year-old man who wanted to try sex while dressed as a woman.

We know what you’re thinking, and Savage was 27 at the time of said encounter.

The story itself is raunchy, funny, and just a little bit wrong, kind of like Savage himself.

Listen to it here but you can skip to the 47 minute mark to get to the Savagey goodness.