Jaimee & Dee

Caught Between a Tie and High Heels

Society EN ↓ 133 episodes

Being Caught Between a Tie and High Heels has been my entire life. Hi, I'm Jaimee. This is a personal journal podcast where I share my life experiences growing up as a Transgender Lesbian. We discuss the issues and situations we face together as I slowly emerge from the closet. Our goal is to reach out to the LGBTQ+ Community and those who may have walked or are walking a similar path to mine to let them know they are not alone.  Caught Between a Tie and High Heels is a property of Purple Turtle Media Group, LLC. This podcast is a copyrighted production of Purple Turtle Media Group, LLC, All r...

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Author

Jaimee & Dee

Category

Society

Podcast website

tieandhighheels.com

Latest episode

Nov 4, 2026

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Episodes

S7E15 - Happy Anniversary! 04.11.2026

Send us a quick note Jaimee shares how she and Dee celebrated their 13th wedding anniversary  ... and the Big Blue Wave they found in their living room.   Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcasts . (It really does help) Visit the Tie...

S7E14 - Feeling Nostalgic 27.10.2026

Send us a quick note Join Jaimee as she takes a trip down memory lane and all the things from her childhood that aren't around anymore.  Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcasts . (It really does help) Visit the Tie and High Hee...

S7E13 - A CBTHH Update 13.10.2026

Send us a quick note A lot has been going on in the last few weeks. Jaimee shares a number of updates on things happening in her world.   Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcasts . (It really does help) Visit the Tie and High Heels w...

S7E12 - We've Always Been Here 29.09.2026

Send us a quick note Exactly how long have transgender people been part of our society? This week, Jaimee takes a quick dive into what it was like to transition in the 70s and discusses transgender people throughout our history.  Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Plea...

S7E11 - Losing My Virginity (AKA: My First Book Signing) 15.09.2026

Send us a quick note Jaimee discusses being deflowered, in a literary sense, at her first book signing. Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcasts . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and In...

S7E10 - Questions From My Friend Shawn - PART 2 09.09.2026

Send us a quick note Jaimee finishes answering the list of questions provided by her friend Shawn.  Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcasts . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instag...

S7E9 - Questions From My Friend Shawn - PART 1 25.08.2026

Send us a quick note After asking a close friend if they had any questions, they didn't, so Jaimee ended up with a strong list of great questions. She answers some of them here in Part 1.  Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast...

S7E8 - How Did You Feel After Transitioning? 11.08.2026

Send us a quick note Jaimee tackles the range of emotions she felt after beginning her transition. Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagra...

S7E7 - A Conversation That Led to a Question 04.08.2026

Send us a quick note In this episode, Jaimee explains how a conversation with a friend about a question someone else asked led them to another question.  Click Here to order the Book or the eBook Please Rate & Review the Book Here Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie a...

S7E6 - Why Did You Write This Book? 29.07.2026

Send us a quick note Through various conversations  over the past month, Jaimee has been asked the same question: "Why did you write this book?" This week, she gives an answer and also explains the motivation for the book.  Click Here to order the Book or the eBook Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcas...

S7E5 - Did You Have The Surgery Yet? 14.07.2026

Send us a quick note Hopefully, this will be the first in a new series highlighting questions transgender people get asked. This week, Jaimee tackles the question that is probably asked of all transgender people.  Click Here to order the eBook Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit...

S7E4 - The End of 2026 Pride 01.07.2026

Send us a quick note Time flies when you're busy. In this week's episode, Jaimee shares her feelings on Pride month as it comes to an end for 2026.  Click Here to order the eBook Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and...

S7E3 - Release Date for The Book 26.06.2026

Send us a quick note A huge announcement this week. We have a release date for the book.  Click Here to Pre-Order the eBook Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagram Support the show

S7E2 - A Little Self Healing 16.06.2026

Send us a quick note In this week's episode, Jaimee shares an update on the book and dives into some steps she's taking to help get her farther away from the things that weigh on her mind. Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Fa...

S7E1 - The Good, The Bad, and The Better 11.06.2026

Send us a quick note Happy Pride, Everyone! Season 7 has officially begun. In this episode, Jaimee gives an update as to what has been going on since she last spoke with you.  Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagram Su...

S6E14 Transgender Awareness Week 18.11.2025

Send us a quick note To celebrate Transgender Awareness Week, Jaimee shares some possibly not-so-familiar members of the transgender community.   Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagram Support the show

S6E13 Are Lesbians Supportive of Trans Women? 22.10.2025

Send us a quick note In this episode, after asking herself a single question, Jaimee shares the results of continually asking "But why?"  Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagram Support the show

S6E12 The First Time I Went Out As My True Self 16.10.2025

Send us a quick note Jaimee provides an exciting update about the Kickstarter Book Campaign. And she shares the story of the first time she ever ventured out as her true self. Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels website Visit us on Facebook and Instagram Su...

S6E11 - Things I Miss Since Transitioning 07.10.2025

Send us a quick note Jaimee shares some reflections on part of her life that she misses from when she presented as a male.   Here's the link to our Kickstarter Campaign . Or if the link doesn't work, copy and paste this URL https://www.kickstarter.com/projects/cbthh/getting-a-transgender-memoir-edited Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Pl...

BONUS - Book Update, 6 Days Left 06.10.2025

Send us a quick note In this bonus episode, Jaimee shares some breaking news about the Book.  Here's the link to our Kickstarter Campaign . Or if the link doesn't work, copy and paste this URL https://www.kickstarter.com/projects/cbthh/getting-a-transgender-memoir-edited Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple...

S6E10 - The Colbert 15 Questions 30.09.2025

Send us a quick note  Here's the link to our Kickstarter Campaign . Or if the link doesn't work, copy and paste this URL https://www.kickstarter.com/projects/cbthh/getting-a-transgender-memoir-edited In this episode, Jaimee answers the 15 questions that Stephen Colbert asks his guests on his late-night chat show.  Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy U...

S6E9 - Dealing with Trans-poster Syndrom 23.09.2025

Send us a quick note  Here's the link to our Kickstarter Campaign . Or if the link doesn't work, copy and paste this URL https://www.kickstarter.com/projects/cbthh/getting-a-transgender-memoir-edited In this episode, Jaimee gives an update on the book. Then she dives into a deeper issue that has been making itself present to her in the last couple of weeks.  Support Us or Get In Touch Se...

S6E8 - Big News! 16.09.2025

Send us a quick note Here's the link to our Kickstarter Campaign . Or if the link doesn't work, copy and paste this URL https://www.kickstarter.com/projects/cbthh/getting-a-transgender-memoir-edited This week, Jaimee shared some exciting news and explained what's been going on in the last few weeks. Support Us or Get In Touch Send us an Email at jaimeecbthh@gmail.com Buy Us a Coffee...

S6E7 - TWT PART 4: The Spouse's Perspective 12.08.2025

Send us a quick note We have definitely covered the topic of Traveling While Transgender with our last two episodes. In this episode, Dee gives her perspective as the cis gender wife in her relationship with Jaimee. Support Us or Get In Touch Send us an Email at  jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It really does help) Visit the Tie and High Heels webs...

S6 BONUS - Traveling While Transgender Part 3 06.08.2025

Send us a quick note The Bonus Episode is my apology for posting a crap episode yesterday. I realize I didn't share as much information as I wanted to about actually traveling while being a transgender person. Please accept this Bonus episode as my apology.     Support Us or Get In Touch Send us an Email jaimeecbthh@gmail.com Buy Us a Coffee Please give us a review on Apple Podcast . (It real...

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