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.

Get Queerty Daily

Subscribe to Queerty for a daily dose of #dansavage #savagelove stories and more


  • balehead

    He’s just another gross media opportunist….cue the surprise…

  • Stache1

    @balehead: You ever get tired of saying negative things?

  • viveutvivas

    What’s it with bi guys and dressing in female underwear? Last year I was having a hit time with a very sexy, very masculine bi guy, until he put on some lace pantihose. I tried to be GGG but my equipment just wouldn’t play along after that point.

  • Pistolo

    I find him to be heinous particularly with that shirt on, yuck, c’mon Dan Savage. It’s a shit joke…you’re walking around with a t-shirt about defecation.

  • CAxlRose

    I love Dan to pieces but….is he familiar with the concept of a one-night stand?

  • TampaBayTed

    I have to agree with viveutvivas. (Nice touch with the Latin BTW.) Such an experience is a de-boner. Years ago a guy that looked like the poster boy for the USMC. Everything was going hot and heavy on the living room couch, when he excused himself and went into his bedroom. A few minutes later the bedroom door opened to reveal my hunky Marine stud dressed in a pinafore and mary janes purring, “I want daddy to fuck me in my panties.” After nearly hurling by dinner, I politely excused my self and ran like hell. On the positive side, he could have been the Folsom Street slasher and I his next victim.

  • TinoTurner

    I was having an affair with a “straight” guy that lived with his fiance. It wasn’t a complicated thing, we’d ask how each others days were, get each other off and go on our way. Since he was straight and we were always limited on time, we didn’t do too much exploring which lead me to become bored. So imagine this straight guy, dressed like a dumb straight guy, talked like a dumb straight guy offer this “Can I come over next time wearing my girlfriends panties?” That was the end of our affair.

  • Jake357

    @balehead: He says from left field. Where dafuck did that come from? I mean, I read the post and most of the comments and I’m a little lost as to where racism came into play. That’s like that Godwin’s law thing.

  • Scribe38

    I thought I was the only for dude this crap happened to. “Mike” super fit, ex-army (still had the hair cut and gear) hit on me in a park. He gave me his number, telling me he was a freak, but I didn’t ask what that meant. Week later we hit a bar and light dinner and head to his place. He first hits a liquor store for smokes. Get back to his place and there is a old dude who is going to watch (freaky but I still wanted him). Well me and Mike start kissing and he stops me and goes to the bathroom. He had bought stockings at the store. The super butch ex army dude wanted me to slap him, call him the f-word, while topping him through a ripped stocking hole I was suppose the tear, as the old guy (70’s) watched and said don’t do that to my son. In Mike’s defense he did tell me he was a freak. And yeah I did it, and kept it to myself until today.

  • sportyguy1983

    I think at this point he will say anything to get attention from the media and gay media in particular.

  • stanhope

    @TinoTurner: if that was Chicago I know that guy LOL. Butch living with a woman. Underneath his man drag were girl panties. He always wanted to bottom which was a-ok with me. I cut him off when I realized his girlfriend was a close friend of a friend of mine. It was great ass though.

  • Toby Ross

    I agree with some of the writers, the point has been lost in the search for fame and fortune.

  • Sebizzar

    @Scribe38: WOW lol. I really think someone who goes that far with a fetish needs to address something from his past :/

    Funny stories guys, if they ever happen to me I’ll be sure to write it down here haha.

Comments are closed.