Category_AnalHow toMenSex TipsWomen

How to Safely Approach Anal Sex?

 

Anal play safety guide

What will I learn?

  • The two essential keys to safe and comfortable anal sex.
  • How to start with fingers and gradually progress to toys and penetration.
  • Which types of anal toys are safest for beginners and why a flared base matters.
  • The role of lubricant — how much to use and when to reapply.
  • Why anal sex isn't limited to any one group and how cock ring combos add pleasure.

There are two essential keys to anal sex:

Lots and LOTS of lube and slowly take it.

You'll want to start with the bit of penetration possible—a finger. This might seem to go without saying, but the finger must be clean with a short (not sharp!) nail.

Apply way more lube than expected, and you may even want to use a small finger sleeve, like this one. Enter and exit slowly, and don't speed up until you truly feel ready for it. And don't forget... MORE LUBE!

How to Make Anal Sex Less Painful?

A guide to safely approaching anal sex with proper preparation
Taking it slow and using the right products makes all the difference.

Start with small, soft tapered plugs or probes when you're ready to level up. Make sure that whatever anal toy you use must have a broader base than its most comprehensive insurable portion. This is imperative whether you're new to anal or an expert. JIMMY JANE's Anal Collection is an excellent start as it features a handful of smooth, tapered silicone plugs that steadily graduate from extra small to extra large.

To explore penetration, try a smaller tapered probe like this super-soft Tapered Teaser before graduating to firmer textured items like the Ribbed P-Spot Vibe (though not exclusive to prostates!) You'll find that the longer you practice anal sex, the easier and more pleasurable it will become. The anus is almost elastic, requiring regular attention to maintain elasticity.

Once you've gained experience, you can explore the vast array of anal toys, including various materials like metal and glass. Due to the rigidness of these materials, it's best kept for advanced anal players and should always be used consciously and cautiously.

Contrary to popular belief, anal sex isn't just for gay men or women, and it doesn't necessarily mean continuous penetration either. The Tavors Cock Ring with Plug has proven this with its bestselling cock ring/prostate plug combo. The ring wraps snug around the penis to enhance and sustain an erection, while the firm plug presses right up against the prostate to intensify sexual pleasure.

How to use Lube for Anal Sex?

Safety checklist

Essential lube rules for anal play

Follow these steps every time for safe, comfortable anal sex.

Use lube. Lots of lube. More lube than you'd ever expect... and then some. And don't forget to reapply throughout play.
Start very small—with a finger—before gradually working your way up to incrementally larger sizes.
Gooooooooo slooooooowwwww. As a beginner, never start fast or hard. You can slowly increase speed once you're used to penetration.
The anus is kind of elastic and requires regular attention. The more you play, the more it will acclimate to penetration.
And seriously, do NOT forget the lube!

Lubricants can enhance your sex life by helping you experience bigger orgasms when having sex with your partner or for self-pleasure. Use an intimate lubricant during intercourse to turn up the heat in the bedroom and make your sex more enjoyable and painless.

Continue your journey

📖 Guide
Anal Vibrator Guide
A beginner-safe guide to choosing and using an anal vibrator.
💡 Tutorial
How to Have a Prostate Orgasm
The benefits of prostate massage and how to find the P-spot.
Tips
How To Prepare For Anal Sex?
First-time tips for getting ready and staying comfortable.

Disclaimers

The information provided in this article is for general informational and educational purposes only. It is not intended as, nor should it be considered a substitute for, professional medical advice, diagnosis, or treatment.

Always seek the advice of your physician or other qualified healthcare provider with any questions you may have regarding sexual health or medical conditions. Never disregard professional medical advice or delay seeking it because of something you have read in this article.

If you think you may have a medical emergency, call your doctor, go to the nearest emergency department, or call emergency services immediately.

Latest Stories

View all

Woman relaxing in a bathtub, holding a pink waterproof luxury personal massager by JIMMYJANE

Waterproof Sex Toys: How to Use Vibrators in the Bath or Shower

Turn your bath or shower into a full-body orgasm zone with waterproof sex toys that are actually safe. Discover which vibrators can go underwater, how to use them, and the best JIMMYJANE toys for wet-and-wild pleasure.

Read more about Waterproof Sex Toys: How to Use Vibrators in the Bath or Shower

Anal Vibrator Guide

Anal Vibrator Guide

Curious about anal vibrators but nervous to try? This beginner-safe guide explains how to use an anal vibrator with lube, hygiene, and step-by-step tips for powerful orgasms, prostate pleasure, and comfortable backdoor play.

Read more about Anal Vibrator Guide

Person in black underwear holding a curved luxury wellness device by JIMMYJANE indoors

5 Reasons Why You Should Try A Double Penetration Orgasm

Double penetration is when a person simultaneously penetrates two of their orifices (vagina, anus, or mouth). While it might seem like one of those fantasies you see only in porn, it can be a powerful sexual experience in real life.

Read more about 5 Reasons Why You Should Try A Double Penetration Orgasm