When Size or Pain Means Stop

If you've ever avoided anal because it hurt, felt intimidating, or just had too many unanswered questions — you haven't had the right conversation yet. Whether you're completely new to backdoor play or you've been doing it for years without the proper foundation, most people are skipping the steps that actually make it feel good. And that's not a problem. That's an education problem.

In this episode, I sit down with nationally renowned anal surgeon Dr. Evan Goldstein — founder of Bespoke Surgical and Future Method — for the most honest, shame-free breakdown of anal health and pleasure you're going to find anywhere.

In this episode, you'll learn:

• Why anal sex should never be painful, what's actually causing the pain, and the exact 4-6 week protocol that prepares your body the right way

• The truth about douching, wet wipes, and why most people are unknowingly damaging their anal microbiome before sex even starts

• How to navigate anal with hemorrhoids, skin tags, or past injuries — and what your options actually are when something goes wrong

This episode is sponsored by...

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Chapters:

0:00 - Intro

1:51 - Meet Dr. Evan Goldstein: Anal Surgeon & Founder of Bespoke Surgical

3:46 - Where Does the Taboo Around Anal Come From?

6:54 - The Three Pillars: How to Prepare, Play & Recover

8:07 - The 4 to 6 Week Dilating Protocol Every Beginner Needs

14:08 - Lube 101: Silicone vs. Water-Based & When to Use Each

15:55 - The Lube Shooter, Empowering the Bottom & Why You Can't Assume Your Partner Knows

16:57 - Douching: Why Water and Store-Bought Enemas Can Do More Harm Than Good

20:33 - Less Is More: Gut Health, Fiber & How to Douche the Right Way

23:27 - Aftercare: What to Do If You Tear or Have Pain

24:19 - Beginner Tips: Positions, Partner Communication & Choosing the Right Size

32:38 - Listener Q&A: Hemorrhoids, Skin Tags & Can You Still Have Anal Sex?

36:43 - Listener Q&A: Colon Surgery, Couples Starting Out & Sex Positions by State

42:14 - Why Wet Wipes Are Wrecking Your Microbiome (Anal and Vaginal)

44:45 - Five Quicky Questions with Dr. Goldstein

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