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Episode 6: Redefining Masculinity and “The Million Dollar Point”

Masculinity, prostate pleasure, shame, and multiple orgasms. In this episode we talk about the evolution of masculinity over the last few decades- from different cultural stereotypes, to new challenges, and the consequences of “toxic” masculinity. Our guest on the show is Charlie Glickman, the author of The Ultimate Guide to Prostate Pleasure, with whom we also discuss the role of shame in men’s pleasure and the “Million Dollar Point,” a seldom talked about spot that allegedly allows men to have multiple orgasms.

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The transcript wasn’t added for this episode.

On this episode our guest is Charlie Glickman, sex and relationship coach, and coauthor of the book The Ultimate Guide To Prostate Pleasure. Here we talk about masculinity and the role that cultural stereotypes play in male sexuality and how we can discover new pleasure possibilities through prostate play! So, whether you are curious or wanting to try something new, you’ll enjoy this pleasure-filled conversation.

Masculine Landscape

According to the work that Charlie has conducted over the last 25 years, not much has changed within the field of masculinity. However, there are now more resources for people who want to work on shifting their relationship to masculinity.

One great resource is Brene Brown’s book I Thought It Was Just Me, which examines shame resilience: “Our attitudes about gender roles, some of them get locked into our systems before we are even verbal.” Some suggested tips for incorporating shame resilience:

  • Check out Brene Brown.
  • Understand that “Shame is the message that I am not accepted as I am”.
  • Shame is all about the relationship between two people, and it can be healed within relationships so that people can be seen and valued as they are.

Another way to tackle the binary gender landscape is to better understand the limited box of masculinity. So often men are taught that if they do anything that is stereotypically classified as female, they diminish For example, Charlie states that ”For a lot of people the idea of man
receiving anal penetrative sex means that he loses all of his masculine status, and it’s not just men who believe that”.

In the book The Ultimate Guide to Prostate Pleasure, Charlie spends a chapter discussing what it means to be a man. He surveyed a few hundred people and discovered that when men first experimented with prostate play the three most common things that came up were: 1) Will this
hurt?, 2) Will this be messy?, and 3) Does this make me gay? “We have this idea that to be penetrated, to be fucked, is to lose status”, and because of this, men have lost so much pleasure potential in their bodies, because they have internalized the belief that sexual pleasure is all about their penis.

I firmly believe that the world is going be a better place when more men take it up the ass.

Trying Prostate Pleasure – The 4 Steps

  1. Lube – and lots of it!
  2. Breathe and relax the pelvic floor
  3. Begin the process once you are already turned on. When in an aroused state, the prostate fills with fluid and becomes more erotically sensitive. You could start with masturbation, dirty talk, oral pleasure, or whatever tickles your fancy.
  4. Recruit a partner or use a toy (the prostate is at a difficult angle to reach by yourself).

Health Benefits of Prostate Play

  • Increases blood flow and can be cleansing
  • Massage can help alleviate the discomfort of an enlarged prostate, which affects 50% of men aged 50 and 80% of men aged 80.
  • Helps break up the biofilm that can reduce the potential for infection.


Talking about your sexual desires with your partner can increase intimacy and vulnerability. By finding the words to speak to your pleasure and desires, you can have a more fulfilling sexual partnership. Here are some tips to enhance connection and intimacy:

  • Breathe together – 5 minutes of belly-to-belly breathing can sync you up with your partner.
  • By stepping out of compliance and traditional sexual scripts, you step into choice.
  • Talk about your pleasure and your experimentation together. This creates a feedback loop so that you can continue to increase the pleasure of your experiences.
  • Pleasure mapping you and your partner(s) bodies to that you can easily communicate your desires.


About the Expert

Charlie Glickman

Charlie Glickman

Charlie Glickman PhD is an internationally-acclaimed sexuality educator, writer, speaker, and teacher. He is certified as a somatic sex educator by the American Association of Sexuality Educators, Counselors, and Therapists. Over his 20+ years in the field, Charlie has explored many different sexual communities, learning from each in order to enrich the lives of his clients. His work focuses on sex positivity, masculinity, and queer issues, and his book, The Ultimate Guide to Prostate Pleasure, was released in 2013.

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