How to Explore Pegging: A Beginner’s Guide to Strap-On Play

Pegging—where a person with a vulva uses a strap-on to penetrate their partner anally—has gained mainstream curiosity and acceptance in recent years. There’s even a podcast about pegging (Ruby Ryder’s Pegging Paradise). Whether you’re interested in pleasure, power dynamics, or simply exploring new sensations, pegging can be an exciting and deeply intimate experience.

If you’re wondering:
🔹 What does pegging feel like?
🔹 How can I introduce it to my partner?
🔹 What’s the best way to do it safely and comfortably?

This guide will help you explore pegging with confidence and without shame.

Why Do People Enjoy Pegging?

People enjoy pegging for many reasons, including:

🔥 Intense Prostate Stimulation – The prostate (P-spot) is a pleasure center that can create powerful orgasms.
🔥 Reversed Power Dynamics – Some heterosexual couples enjoy switching traditional penetration roles.
🔥 New Sensory Experiences – Many find anal play uniquely pleasurable with the right technique.
🔥 Deepened Trust & Intimacy – Pegging requires communication, vulnerability, and exploration together.

💡 Pegging is for anyone—regardless of gender or sexual orientation! Fellas… enjoying anal doesn’t make you gay, it makes you someone with a prostate who isn’t letting that potential pleasure center go to waste.

Step 1: How to Talk to Your Partner About Pegging

If you’re interested in pegging but not sure how to bring it up, here are some conversation starters:

💬 “I read about pegging today, and it sounds really interesting! Have you ever thought about trying it?”
💬 “I love the idea of exploring new things together—what do you think about strap-on play?”
💬 “I want to focus on your pleasure in a new way. Would you be open to it?”

💡 Framing pegging as a fun, shared adventure rather than a demand could make your partner more open to the idea.

Step 2: Choosing the Right Strap-On & Toy

A well-fitted strap-on makes pegging more comfortable and pleasurable for both partners.

✅ Best Strap-Ons for Pegging:

✔ Two-Strap (Harness Style) – Provides stability and control for smoother thrusting.
✔ Double-Ended or Vibrating Dildos – Can stimulate both partners.
✔ Smaller, Beginner-Friendly Dildos – Start with narrower, body-safe silicone toys before going bigger.

🚫 Avoid:

❌ Large or Thick Toys Right Away – Start small to avoid discomfort.
❌ Cheap or Poor-Quality Harnesses – Invest in adjustable, body-safe materials for comfort.

💡 A good harness makes pegging easier and more pleasurable—choose one that fits well. I highly recommend stopping in at your local sex shop. You may be surprised how kind, comfortable and informative the staff can be. And they might even let you try harnesses on before you buy.

Step 3: Prepare for Pegging (Lube, Hygiene & Comfort)

✔ Use Plenty of Lube – Water-based, high quality silicone or a hybrid lube is essential for comfort. (hybrid is my personal favorite)
✔ Go Slow & Relax – Rushing can cause discomfort—take your time.
✔ Try Finger or Small Toy Play First – Prepping with fingers or small plugs helps the body adjust.
✔ Use Deep Breathing & Communication – Helps with relaxation and pleasure.

💡 Pegging should be pleasurable, not painful—proper preparation makes all the difference! If you’d like to talk with someone about how to prep, and how to avoid pain or discomfort, book a free, private intro session with me. You can ask anything you want! No need to hold back. I’ve heard it all.

Step 4: Best Pegging Positions for Beginners

Certain positions make first-time pegging easier and more comfortable.

✅ Beginner-Friendly Pegging Positions:

✔ Missionary (Face-to-Face) – Allows for eye contact, intimacy, and control.
✔ Spooning (Side-By-Side) – Gentle, relaxed position with easy access.
✔ Doggy Style (On All Fours) – Gives great penetration angles, but requires extra lube and prep.

💡 Experiment with different positions to find what feels best for both of you.

Step 5: Take It Slow & Communicate During Pegging

✔ Start with shallow thrusts and increase depth gradually.
✔ Check in with your partner—ask how it feels.
✔ Use a "1-10" pain scale to ensure comfort.
✔ Keep lube handy and reapply as needed.

💡 Good pegging is all about listening to your partner’s body and pacing the experience to maximize pleasure.

Step 6: Add More Intensity Once Comfortable

Once you and your partner are comfortable with pegging, try adding:

🔥 Vibrating Toys – A vibrating dildo can intensify the experience.
🔥 Hand Stimulation – Combine pegging with manual stroking for explosive orgasms.
🔥 Roleplay & Dirty Talk – Adding dominance/submission elements can heighten the dynamic.

💡 There’s no “right” way to do pegging—explore what excites both of you!

Step 7: Pegging Aftercare & Emotional Connection

Since pegging is physically and emotionally intense, aftercare helps partners feel safe, loved, and connected.

Best Aftercare Practices:

💖 Cuddle & Reassure Each Other – Helps reinforce trust.
💖 Massage or Warm Compress – Eases muscle tension.
💖 Hydrate & Relax – Helps the body recover.
💖 Talk About the Experience – Discuss what felt good and what to adjust next time.
💖 Check In the Following Day – There’s always a “come down” especially after trying something new sexually. Help each other ground. And discuss any new perspectives you’ve come to once some time has passed.

💡 Aftercare deepens intimacy and makes future experiences even better.

Common Pegging Mistakes (And How to Avoid Them)

🚫 Skipping foreplay & prep. ✅ Always start with a finger or toy play first.
🚫 Going too fast, too soon. ✅ Slow, controlled movements prevent discomfort.
🚫 Using little or no lube. ✅ Generous lube application is non-negotiable.
🚫 Ignoring communication. ✅ Checking in frequently ensures both partners enjoy the experience.

💡 A great pegging experience comes from patience, trust, and mutual pleasure!

Final Thoughts: Pegging Can Be Fun, Exciting, and Intimate

Pegging is more than just a sexual act—it’s an opportunity to:

✔ Explore new sensations & prostate pleasure.
✔ Enhance intimacy & trust in your relationship.
✔ Experience role reversal & new dynamics.

💡 Want expert guidance on introducing pegging to your relationship? I specialize in helping people communicate desires, explore new experiences, and create safe, fulfilling sex lives. Book a free, private intro session today.