About the Book

More men than ever before a re exploring prostate play and discovering how much fun it can be. As experienced sexuality educators, we’ve been answering questions and helping guys figure out how prostate play works for a long time. So we decided the world was finally ready for a book all about prostate fun!

When we sat down to write The Ultimate Guide to Prostate Pleasure, there were a lot of different questions we wanted to answer. But even with all of our experience, we also knew that a lot of men and their partners had tips and suggestions to offer, as well as stories to tell. So this project started off with a survey of men and we were amazed at how many guys had discovered tricks for making prostate pleasure as fun as possible. We’re deeply grateful to all the folks who shared their experiences with us. We’ve included lots of their tips, as well as plenty of quotes, so you can read their own words. We’re excited to share this book with you and we hope that you discover new ways to experience amazing pleasure.

Want to see what you’ll get when you read the book? Here’s the table of contents!

Table of Contents

Foreword by Dr. Carol Queen

Chapter 1: Before We Start: Frequently Asked Questions

  • “So my prostate gland is…up my ass?”
  • “Isn’t it messy?”
  • “Doesn’t it hurt?”
  • “If a man gets penetrated, doesn’t that mean he’s gay/effeminate/being dominated?”
  • “Won’t people think I’m weird?”
  • “My partner won’t be into that”
  • “My cock is all I need to get off”
  • “I had a prostate exam at the doctor’s and it didn’t feel good at all!”
  • “Are there health risks?”
  • “That all sounds great, but I still don’t know how to find my prostate!”

Chapter 2: The Sexy Prostate

  • A Little-Known Pleasure Zone
  • A Unique Sensation
  • Prostate Orgasm
  • Lingering on the Brink
  • Multiple Orgasms
  • The Prostate’s Role in Anal Pleasure
  • Other Reasons to Enjoy Prostate Stimulation

Chapter 3: What Is the Prostate?

  • Prostate Anatomy
  • Phases of Ejaculation
  • The Male G-Spot?
  • About Nerves

Chapter 4: Hygiene

  • Quick Tips for More Hygienic Anal Play
  • Enemas
  • Safer Sex Barriers
  • Hair Removal

Chapter 5: Penetration 101

  • The Prostate and Then Some
  • Penetration: The Basics
  •  If It Hurts
  • Slow and Steady Wins the Race
  • Making It Feel Good

Chapter 6: Searching for “the Magic Button”

  • Finding It Is Not Just about Location
  • The Mind–Body Connection
  • Realistic Expectations
  • Learning to Receive
  • Arousal
  • To Stroke, or Not to Stroke (Your Cock)
  • Rewiring
  • Open to the Sensation
  • Two Approaches: Tantra and Fantasy
  • What You Might Feel

Chapter 7: Find It: Locating the Gland

  • Set the Scene
  • Solo Exploration: Locate the Prostate
  • Feeling for It: Guided Solo Exploration
  • Partnered Exploration: Locate the Prostate

Chapter 8: Bringing Up the Topic: A Guide for Him and Her

  • Why Guy–Girl Couples Are Enjoying Prostate Play
  • The Benefits of Taking Turns
  • Reasons for Hesitation
  • Open the Conversation
  • Be Flexible

Chapter 9: Prostate Massage

  • What Is Prostate Massage?
  • Tips for Combining with Cock Play
  • How Many Fingers?
  • Massage Strokes
  • Fisting

Chapter 10: The “Sweet Spot”: Massaging the Perineum

  • Why the Sweet Spot Feels Good
  • Finding the Sweet Spot
  • Find Your Own
  • Partner Massage
  • “I Don’t Feel Anything”

Chapter 11: Toys

  • Lube
  • Toy Tips
  • Butt Plugs
  • Made with the Prostate in Mind
  • G-Spot Toys
  • Vibrators
  • Dildos
  • Strap-on Harnesses for Him and Her
  • Inflatables
  • Electrostim
  • Urethral Sounds
  • Toy Materials and Cleaning

Chapter 12: Anal Sex and Strap-on Fucking

  • Technique
  • Positions
  • Pegging: Strap-on Sex for Guy–Girl Couples

Chapter 13: Real Men Don’t

  • Does It Make Me Less of a Man?
  • The “Act Like a Man” Box
  • Outside the Box Is a Scary Place
  • Why the Box Is Nonsense
  • Picking and Choosing from the Box
  • Back to Prostate Play
  • It’s Up to You

Chapter 14: Prostate Health

  • Prostatitis
  • Prostate Health Tips
  • Benign Prostatic Hyperplasia (BPH)
  • Prostate Cancer
  • Sex after Prostate Cancer Treatment

Chapter 15: Possible Benefits of Prostate Massage

  • How May Prostate Massage Be Beneficial?
  • A Little History
  • Can Massage Help Prevent Prostate Cancer?
  • DIY Prostate Massage for Health

Afterword by Dr. Debby Herbenick

illustrations by Katie Diamond and Dean Scarborough