Strictly Anonymous Confessions
Strictly Anonymous Confessions

1400 - Nate on Pegging and Prostate Orgasms

March 18, 2026

AI Summary

5 min read

In a conversation that is part tutorial, part personal history, and part myth-busting, a longtime listener named Nate explains to host Kathy how he and his wife have integrated pegging and prostate play into their marriage over the past decade. The episode is grounded in Nate's own experience: he has been married for thirty years, and for the last ten of those, he and his wife have made prostate play a regular, scheduled part of their sex life. The conversation is less about shock value and more about practical mechanics, relationship dynamics, and the psychology of introducing a stigmatized act into a long-term partnership.

The Origin Story: How the Conversation Happened

Nate's path to pegging began with solo experimentation as a teenager, followed by a twenty-year gap. About ten years ago, after doing research on Tumblr and Reddit, he decided to bring it up with his wife. He did not do it face-to-face. Instead, he texted her a picture of a strap-on and said he was interested in trying it. This method worked for them because it gave her time to process and respond without the pressure of an immediate, in-person reaction. She was hesitant but willing. They bought a starter kit—a medium-sized Tantus dildo and a cheap harness—and tried it for the first time on Valentine's weekend ten years ago. The first experience was intense but not perfect; the harness was low-quality, a

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What you'll learn

  • 1 (05:33) **Introduction to Nate and His Story** - Host Kathy introduces Nate, a long-time listener who will discuss pegging and prostate orgasms.
  • 2 (07:19) **The Appeal of Prostate Orgasms** - Kathy explains her obsession with male anal play and asks Nate to describe the experience.
  • 3 (09:59) **The Layers of Pleasure: Taboo and Connection** - Nate explains that the appeal goes beyond the physical, including the taboo and the mental "mind fuck" of it.
  • 4 (11:10) **The Origin Story: How It Started** - Nate details his early solo experimentation and how he brought up pegging to his wife.
  • 5 (18:32) **The First Time and Setting a Schedule** - Nate describes the first pegging experience and how they normalized it.
  • 6 (23:46) **Tutorial: How to Find Your Prostate** - Nate gives a step-by-step guide for beginners.
  • 7 (28:43) **The Wand, Warm-Up, and Multiple Orgasms** - Nate details how they use the wand for warm-up and the experience of multiple orgasms.

+ Full timestamped outline available in the app

Show Notes

Nate is into pegging and prostate orgasms and he called in to talk all about it. Tune in to hear all the details including how and when he brought up pegging to his wife and how she reacted, their very first time and exactly what they bought and what went down, how he gets himself to have a prostate orgasm, the wand he enjoys uses for foreplay, how many prostate orgasms he has had in one sitting via prostate play and what they feel like, the other toy he uses to have more intense orgasms and exactly how he uses it, the myths of pegging and anal play that exist including how and why pegging doesn’t have to be a dom/sub act and instead can be very sensual and intimate plus, the sub Reddits for pegging he uses that are super helpful, how he suggests bringing up pegging or any anal play to your partner, the specific harnesses and toys he recommends, the lube he likes and doesn’t like for pegging plus a whole lot more.


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