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. Just go to More Dr. Emily: Shop With Emily! Explore Emily’s favorite toys, pleasure accessories, bedroom essentials, and more — designed to support your pleasure and confidence. Free shipping on orders $99+ (some exclusions apply).5 Interested in 1:1 Coaching with Emily? Go to to apply! Sex With Emily Guides: Explore pleasure, deepen connections, and enhance intimacy using these Sex With Emily downloadable guides. The only sex book you’ll ever need: Smart Sex: How to Boost Your Sex IQ and Own Your Pleasure Want more? Visit the Sex With Emily Website Let’s get social: X Let’s text: Sign up here Want me to slide into your email inbox? Sign Up Here for sex tips on the regular. 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