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After the 2010 election, burned and bummed out, Kaytlin got into stand up comedy. She specialized in telling her story as a sex worker to audiences all over the country. Her critically acclaimed one woman show Cuntagious, personal essays, stand up and podcast appearances told the story of an unapologetic and audacious young woman who was unafraid to take risks and push boundaries.
After the election of Donald Trump in 2016 Kaytlin felt disillusioned with the nihilistic and trolling culture of comedy and an urgent need to get back into politics. In 2017, finally using her history degree, she started The Oldest Profession Podcast, an irreverent history of audacious whores, with the explicit intention of educating her growing audience about the history of policing prostitution. Each episode tells the story of a different sex worker from history. The show has become a resource for sex workers, activists and allies all over the world. After the passage of SESTA/FOSTA April 11th, 2018 she committed to advocating for sex worker rights.


Bailey became the founding  Director of Communications for Decriminalize Sex Work in January, 2019.


 Kaytlin continues her stubborn crusade against whorephobia with her production company, Old Pro Productions, Inc founded in 2020.

The Oldest Profession Podcast is a fiscally sponsored project which produces public history events throughout the country including the Old Pro Project on January 25th.  She tours the country as a stand up comic and sex worker rights advocate. 


Unphased by conflict or dangerous ideas Bailey has worked as a political organizer, sex worker, stand up comic, and writer. She is returning to politics as the Director of Communications for Decriminalize Sex Work to challenge laws criminalizing the oldest profession.

When she was thirteen, Kaytlin joined Youth Voice Raleigh, whose stated mission was to elevate the youth voice in the public sphere. The group of young advocates did not want parents, teachers, or politicians speaking on behalf of those who can speak for themselves. She believes the same is true of sex workers.

At fifteen, Kaytlin began volunteering for Planned Parenthood, being recognized as the organization’s young volunteer of the year in 2005. After college, she worked for Grassroots Campaigns working in twelve cities, in nine states, for eleven clients, in eighteen months doing a variety of fundraising, letter writing, voter persuasion and get out the vote campaigns.


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