Playing the Whore with Kaytlin Bailey: From fantasy to reality

Comedian and former sex worker Kaytlin Bailey is this week’s special guest on The Manwhore Podcast! Kaytlin was a teenaged escort and is now a hilarious stand-up comic and self-proclaimed cunt. This episode features two comedians talking about sex work and gender in the funniest way possible!

kaytlin bailey

Kaytlin Bailey made enough money doing sex work that at 17 she opened a Roth IRA! Her and I share the same fetish of being paid for sex. She has just gotten to live her fantasy way more times than I have. We discuss how a whore fantasy turned into a job. Plus, am I allowed to “appropriate” the word whore by calling myself a manwhore? (duh, of course)

Hear Kaytlin’s reasons for faking orgasms on this week’s episode. Of course, faking orgasms would not be necessary if we lived in a society where a man’s masculinity wasn’t so caught up in him “giving” a woman an orgasm. We’ve become so goal-oriented that we forgot that sex is about feeling good during your sexual encounter, not getting to the finish line as fast as you can. “We’ve stopped listening to our bodies. We’ve stopped listening to each other’s bodies. We’ve stopped being able to authentically connect because we’re running through a To Do list in our head.”

Not all sex worker stories are about crazy, kinky sex. Some are sweet. Some are sad. Some involve intimacy and some involve watersports. Kaytlin has had diferent types of clients. Plus, we go over Billy’s various close encounters with being paid for sex!

Soft penises? Kaytlin’s all about them. Let’s talk about it!

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Buy your tickets for Kaytlin Bailey’s one-woman show Cuntagious by visiting! Shows are at The Tank theater in New York City on July 10, 11 and 12! The Naked Comedy Show at The Creek and The Cave is on July 17. Buy tickets here!

Follow Kaytlin on Twitter @KaytlinBailey!

This week’s episode is sponsored by the labia minora. They may be minora, but they’re a major deal.

Email your comments, questions and boobies to