Caught Between a Tie and High Heels

Caught Between a Tie and High Heels

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. Along with my wife, Dee, 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.

Episodes

November 18, 2025 26 mins

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To celebrate Transgender Awareness Week, Jaimee shares some possibly not-so-familiar members of the transgender community.  

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In this episode, after asking herself a single question, Jaimee shares the results of continually asking "But why?" 

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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.

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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

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October 6, 2025 3 mins

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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

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September 30, 2025 41 mins

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 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. 

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September 23, 2025 33 mins

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 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. 

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  • Send us an Email at jaimeecbthh@gmail.com
  • Buy...
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September 16, 2025 27 mins

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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.

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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.

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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.    

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August 5, 2025 40 mins

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Traveling and being Transgender can be a stressful time. Jaimee revisits this topic from Season 4, Episode 3 as she shares her recent international trip.

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July 16, 2025 29 mins

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We all find ourselves in situations that are less than desirable. During these times, nothing would be better than unplugging and disconnecting from everything, even if for just a moment or two. 

Jaimee shares part of her escape when she was growing up and trying to figure out who she was and what was going on with her body. All while living through some tough times in her life. 

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July 9, 2025 31 mins

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 Have you ever caught yourself doing something so peculiar that you wonder if anyone else on earth shares your quirk? That moment of self-awareness hit Jaimee hard recently, prompting this deep dive into the wonderfully weird habits that make her...well, her. 

 What weird habit do you have that might not be as unusual as you think? Please share it with us on social media or through our website at tieandhighheels.com. Y...

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June 24, 2025 40 mins

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This week Dee joins Jaimee as they talk about lesbian terms neither of them knew existed. 

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June 17, 2025 32 mins

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It's been a long time comin', but the wait is over! Season 6 has officially begun. In this episode, Jaimee talks about what's been going on since December of 2023.

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May 19, 2025 2 mins

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This is a bonus episode that asks one question. Would you all like to hear more episodes? 

Let me know by contacting me through any of these links:

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September 17, 2024 30 mins

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Jaimee shares one story in order to tell another about a newly acquired self-realization. 
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August 28, 2024 50 mins

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After taking a little over 9 months, We finally recorded a first episode. YAY!
Jaimee & Dee are back and giving an update on whats been going on all this time. 
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December 5, 2023 38 mins

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In this special episode, Jaimee and Dee celebrate by changing it up a bit as Dee interviews Jaimee. 
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November 21, 2023 43 mins

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Dee and Jaimee continue their conversation about Jaimee's ability to make friends with Jaimee sharing her result of her  Myers–Briggs Type Indicator.
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