How to Safely Approach Anal Sex

There are two essential keys to anal sex: lots and LOTS of lube, and take it very slooooow.

You'll want to start with the smallest 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 slowly and exit slowly and don't speed up until you truly feel ready for it. And don't forget... MORE LUBE!

When you're ready to level up, start with small, soft tapered plugs or probes. Make sure that whatever anal toy you use, it must have a base that is wider than its widest insertable portion. This is imperative whether you're new to anal or an expert. The Anal Fantasy Collection is a great start as it features a handful smooth, tapered silicone plugs that steadily graduate from extra small to extra large.

Graduated Anal Fantasy Collection Anal Plugs from mini to 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 definitely 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 so it requires regular attention in order 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.

Metal Worx Mini Luv Anal Plug
Metal Worx Mini Luv Plug
Bare Creation Classic Glass Anal Plug
Bare Creation Classic Glass Anal Plug

Contrary to popular belief, anal sex isn't just for gay men or women, and it doesn't necessarily mean continuous penetration either. The Saturn 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 erection, while the firm plug presses right up against the prostate to intensify sexual pleasure.

Saturn Cock Ring with Plug

So, what have we learned?

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

Shop Beginners Anal Essentials

Organic Water-Based Liquid Lubricant

$25.00 | No Longer Available

Organic Water-Based Liquid Lubricant

Organic Water-Based Gel Lubricant

$25.00 | No Longer Available

Organic Water-Based Gel Lubricant

Water-Based Lubricant

$8.00* | No Longer Available

Water-Based Lubricant

Silicone-Based Lubricant

$10.00* | No Longer Available

Silicone-Based Lubricant

Latex Finger Sleeves

$4.49 | No Longer Available

Latex Finger Sleeves

Mini Silicone Plug

$13.49 | No Longer Available

Mini Silicone Anal Plug

Small Silicone Plug

$17.99 | No Longer Available

Small Silicone Anal Plug

Tapered Teaser

$13.00 | No Longer Available

Tapered Anal Teaser

Shop All JimmyJane Anal

*Lubricant prices determined by size. Prices and availability are subject to change.