All Episodes

April 2, 2025 54 mins

Mermaid roleplay, creating sexy safe spaces, and de-stigmatizing sex work—Kaylani shares how working at a legal brothel has led her down a path of self-discovery, independence, and deeper human connection.


 

00:00 Why sex work is “intimacy therapy”

03:20 Community, conquering shame, and feeling empowered as a legal courtesan

09:15 Creating safe judgement-free sexy spaces that allows lovers to express their vulnerability

12:51 Mermaid role play and fulfilling partners’ fantasies

17:19 Client success stories and the magic of changing mindsets

19:21 Why do people go to the legal brothel?

23:45 Noticing relationship patterns and what she’s learned from toxic partnerships

27:26 Growing up boy crazy with mixed sex ed messaging

30:13 A long-time lesbian porn fantasy come true

33:28 All-girl orgy configurations

34:43 How she goes deep with clients

36:47 Virgin parties, foreplay tips, and teaching partners how to make her cum

39:05 Why she likes to connect with words before connecting physically

42:51 Feeling supported by her partners and debunking the “transactional” nature of sex work

45:38 Consistent self-care routines and staying curious

48:45 A future of intimacy coaching and helping women leverage sexual energy into financial freedom

51:44 How she’s spreading happiness, acceptance, and compassion


 

📈STATS | 32 heteroflexible multicultural female, she/her pronouns, single, elite companion, Las Vegas-based legal courtesan, into: meeting new people, deep conversations, spending time with partners, initiating the inexperienced, playing with lady friends, role play, and creating safe spaces for partners


 

🔗 KAYLANI LINKS | @xoxokaylani

Ask a question, share a story or be a guest: howtowoo.fyi

Explore Luna's rabbit hole: @lunarwoohoo

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.