The Manwhore Podcast: A Sex-Positive Quest

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 c*nt. This episode features two comedians talking about sex work and gender in the funniest way possible!

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!

Support The Manwhore Podcast and get awesome rewards! Make your pledge today by visiting my Patreon page!

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

Direct download: 2015-06-24-Kaytlin-Bailey.mp3
Category:general -- posted at: 6:30am EDT

We're talking BDSM impact play and polyamory on this week's Manwhore Podcast with Anastasia. My kinky friend Anastasia is a Twitter hook-up that turned into a friendship where we share the finer parts of our sexual exploits. It's a kinky, sexy, loving poly episode!

The hardest part about polyamory isn't jealousy or hurt feelings. It's scheduling! Anastasia and I discuss #polyproblems. I attempt to diagram her poly family of relationships. It's not very easy. We also learn about her polyamorous origins with her current long-distance primary partner.

We're learning all about impact play and BDSM this week. Anastasia talks about whipping, flogging, hitting, caning and being tied down. "Your kink is not my kink—and it's okay." Just remember that consent is key!

How do you find your sex toys? Listen to my guest's story about buying her first pair of handcuffs at a Ren Faire!

Support The Manwhore Podcast and get awesome rewards! Make a pledge on my Patreon page!

This week's show is sponsored by, a leader online retailer of male sex toys. Use the code MANWHORE15 for 15% off your next purchase!

Email your comments, questions and boobies to

Direct download: 2015-06-17-Anastasia.mp3
Category:general -- posted at: 6:00am EDT

No matter how hard we tried, Andrea Allan and I could not seem to have sex with each other. This week's episode is with my friend and fellow comedian Andrea Allan, an "off-putting babe" who likes rough sex and funny men. Hear the story of two people wanting to bang each other who just…couldn't.

Comedian Andrea Allan has dated—f*cked— a lot of stand-up comedians. We discuss the common question amongst the comedy community: should comics date other comics? Even if you do, could you f*ck a bad comic? Comedian sex has the same major rule as stand-up comedy: Always Be Funny.

Andrea likes rough sex that sounds like a homicide. Hear about the time her roommate had to decide to either c*ckblock Andrea or potentially let her be murdered. The fellow podcaster is so intense in bed—not bad, just intense—that she scared my d*ck into submission. How should a woman react to a guy's sexual dysfunction?

Congratulations to Caitlyn Jenner on her Vanity Fair reveal! Congratulations, also, to Ramon F. on winning the free Autoblow 2 giveaway!

Listen to a hilarious story about a prank I pulled involving women's panties on Andrea's podcast The Hot Mess Comedy Hour! Follow her on Twitter @AndreaComedy. Also, you probably have herpes.

Support The Manwhore Podcast and get awesome rewards! Make a pledge today on my Patreon page!

This week's show is sponsored by collections of empty whiskey bottles next to your bed. They're not just for college kids anymore.

Email your comments, questions and boobies to

Direct download: 2015-06-09-Andrea-Allan.mp3
Category:general -- posted at: 6:00am EDT

Burlesque veteran Peekaboo Pointe joins me on this week's Manwhore Podcast to talk about dancing, dating and getting naked. Peekaboo has a storied past as rich as the history of burlesque itself! I enjoyed talking to the "Lazy Stripper" about this fun, sexy art form and getting to know what it's like being, well, Peekaboo!

Peekaboo Pointe is "The Fastest Tassle Twirler from East to West"! With well over ten years of experience under her belt, Peek has been around since the early days of New York City's burlesque revival. She tells me about how she transitioned from modern dance to stripping down to pasties. "Can't we all just get naked and make some art?!"

Thank you so much to everyone who emailed, tweeted and shouted their kind words after hearing last week's break-up pre-intro. It means so much to me to have such amazing strangers who care about me. From the bottom of my heart, I love you all. Except Jim.

Peekaboo schooled me on the history of burlesque and its recent resurgence in the new millenium. We also compare the many similiarities between burlesque dancing and stand-up comedy. Because how can you not sleep with at least one auience member? Plus, we tear down Tinder and thoughtless pick-up lines.

Read my quotes in Vanessa Golembewski's Refinery29 piece, "How Do New Yorkers Respond to Rape Jokes?"

Check out Peekaboo Pointe being fabulous!

Transition song: "Night Train" by Jason Aldean

Support The Manwhore Podcast and get awesome rewards! Help me make the podcast even better and visit my Patreon page!

This week's show is sponsored by hibernation. It's not getting fat. It's hibernation.

Email your comments, questios and boobies to

Direct download: 2015-06-03-Peekaboo-Pointe.mp3
Category:general -- posted at: 6:00am EDT