Episode 3
Masculinity and crossdressing:
A Madison Cawthorn tail of hypocrisy.

Throw out everything you know or think you know about crossdressing!

Recently, a photo surfaced on the internet of North Carolina Congressman Madison Cawthorn wearing women’s lingerie. This episode isn’t going to get into politics, but instead shine a light on the connection between gender, masculinity, and crossdressing.

Join me in this episode of the Secure Masculinity podcast, as I break down the real practice of crossdressing, the insights I’ve gained from researching every day, average Joes who crossdress, and how this relates to the root of insecure masculinity.

What are the first thoughts that come into your mind when you hear “crossdresser”? Does your mind begin to judge or shame or even feel embarrassed? If so, I invite you to let this episode help reframe these thoughts for you.

It’s not enough to push this “controversial” topic to the wayside and pretend it’s not important. Instead, we must explore it, uncover the shameful patriarchy that clouds our view of it, and embrace these men with compassion and empathy just as we do with men who identify as sports enthusiasts, many times it’s the same man!

In this episode, you’ll learn:

  • [01:13] Who is Madison Cawthorn and what are his views on gender and masculinity?
  • [03:53] Men are using violence and control tactics to control other men, leading to much more harm than good.
  • [04:32] The root of insecure masculinity.
  • [07:42] Crossdressing is a unique, personal, and often private behavior – so, why do men do it?
  • [10:10] Crossdressing is not about gender identity or homosexuality.
  • [10:49] What I’ve learned from observing and researching crossdressers.
  • [18:13] The ultimate takeaway: Stop shaming and pressuring men to fit into an unrealistic mold.

Let’s dive deeper.

Here are a few key takeaways…

  • In March 2021, on a podcast designed to “restore and reclaim” masculinity, Madison Cawthorn expressed a belief that we have bred a problematic generation of “soft men”. But what does that mean? It’s subjective; all those definitions lead to the negative notion that soft men are not traditionally masculine.
  • A group of people in our society believe men are not “real men” anymore. This group is very harmful to all men, constantly attacking and shaming them. This clearly isn’t the right path to “restoring and reclaiming masculinity”.
  • There are countless masculine identities that are innate to men, but patriarchy defines masculinity in one singular, measurable way. If a man is actually empowered to grow into their own unique masculinity, they’ll be healthy and secure in their adulthood.
  • Some men crossdress because it makes them feel naughty and sexy, others do it because they’re curious or they see it as artful. For some, it just feels good. Most male crossdressers are attracted to women, are married, and even have children. Another common trait is that they don’t have any desire to be seen and noticed by others. It’s usually very private and personal. Though, it really doesn’t matter WHY men crossdress, what matters is that we don’t condemn men for crossdressing.
  • After observing crossdressing men in all their glory, I realized that when they engage in it, they’re aiming to live out a dimension of who they are for just a few hours without any judgment and shame. It gives them freedom and validation.
  • For society to misunderstand, judge, and deplore men who indulge in crossdressing is extremely unhealthy. It’s not a new, unnatural act. It has been a well-documented part of our humanity throughout millennia. We need to stop shaming and pressuring men to fit into an unrealistic mold because all masculine identities are equally valid, acceptable, and respectable.


If you enjoyed this episode and want to further support us, please RATE & REVIEW Secure Masculinity on Apple Podcasts, Google Podcasts, Amazon, Spotify and Stitcher! Then, SHARE this episode with a friend or two!


Connect with me!

Follow me on Twitter:

Follow Positive Masculinity Academy on Instagram:

Visit Positive Masculinity Academy’s website: https://positivemasculinityacademy.com

Follow Feminists For Men on Instagram:

Visit Feminists for Men’s website: https://feministsformen.org

Learn about my cancer prevention work: www.doctorjamshidi.com

Throw out everything you know or think you know about crossdressing!

Recently, a photo surfaced on the internet of North Carolina Congressman Madison Cawthorn wearing women’s lingerie. This episode isn’t going to get into politics, but instead shine a light on the connection between gender, masculinity, and crossdressing.

Join me in this episode of the Secure Masculinity podcast, as I break down the real practice of crossdressing, the insights I’ve gained from researching every day, average Joes who crossdress, and how this relates to the root of insecure masculinity.

What are the first thoughts that come into your mind when you hear “crossdresser”? Does your mind begin to judge or shame or even feel embarrassed? If so, I invite you to let this episode help reframe these thoughts for you.

It’s not enough to push this “controversial” topic to the wayside and pretend it’s not important. Instead, we must explore it, uncover the shameful patriarchy that clouds our view of it, and embrace these men with compassion and empathy just as we do with men who identify as sports enthusiasts, many times it’s the same man!

In this episode, you’ll learn:

  • [01:13] Who is Madison Cawthorn and what are his views on gender and masculinity?
  • [03:53] Men are using violence and control tactics to control other men, leading to much more harm than good.
  • [04:32] The root of insecure masculinity.
  • [07:42] Crossdressing is a unique, personal, and often private behavior – so, why do men do it?
  • [10:10] Crossdressing is not about gender identity or homosexuality.
  • [10:49] What I’ve learned from observing and researching crossdressers.
  • [18:13] The ultimate takeaway: Stop shaming and pressuring men to fit into an unrealistic mold.

Let’s dive deeper.

Here are a few key takeaways…

  • In March 2021, on a podcast designed to “restore and reclaim” masculinity, Madison Cawthorn expressed a belief that we have bred a problematic generation of “soft men”. But what does that mean? It’s subjective; all those definitions lead to the negative notion that soft men are not traditionally masculine.
  • A group of people in our society believe men are not “real men” anymore. This group is very harmful to all men, constantly attacking and shaming them. This clearly isn’t the right path to “restoring and reclaiming masculinity”.
  • There are countless masculine identities that are innate to men, but patriarchy defines masculinity in one singular, measurable way. If a man is actually empowered to grow into their own unique masculinity, they’ll be healthy and secure in their adulthood.
  • Some men crossdress because it makes them feel naughty and sexy, others do it because they’re curious or they see it as artful. For some, it just feels good. Most male crossdressers are attracted to women, are married, and even have children. Another common trait is that they don’t have any desire to be seen and noticed by others. It’s usually very private and personal. Though, it really doesn’t matter WHY men crossdress, what matters is that we don’t condemn men for crossdressing.
  • After observing crossdressing men in all their glory, I realized that when they engage in it, they’re aiming to live out a dimension of who they are for just a few hours without any judgment and shame. It gives them freedom and validation.
  • For society to misunderstand, judge, and deplore men who indulge in crossdressing is extremely unhealthy. It’s not a new, unnatural act. It has been a well-documented part of our humanity throughout millennia. We need to stop shaming and pressuring men to fit into an unrealistic mold because all masculine identities are equally valid, acceptable, and respectable.


If you enjoyed this episode and want to further support us, please RATE & REVIEW Secure Masculinity on Apple Podcasts, Google Podcasts, Amazon, Spotify and Stitcher! Then, SHARE this episode with a friend or two!


Connect with me!

Follow me on Twitter:

Follow Positive Masculinity Academy on Instagram:

Visit Positive Masculinity Academy’s website: https://positivemasculinityacademy.com

Follow Feminists For Men on Instagram:

Visit Feminists for Men’s website: https://feministsformen.org

Learn about my cancer prevention work: www.doctorjamshidi.com