5 Anal Adventures – From Beginner to Advanced

Unrecognizable woman butt and strong sporty legs

The booty is multi-purpose. But I’m here to tell you that one of its purposes is pleasure. 

That’s right…immense, abundant, sexual pleasure – as well as anal orgasms! – for all genders and sexualities. That’s because anal play stimulates your pelvic floor, the muscle group responsible for orgasms. Yes, including anal orgasms. 

But anal play also has cool psychological benefits. It fosters more acceptance of your entire body, helping shed one more layer of societal shame (hallelujah). For partners, anal play can also create a lot of intimacy, trust and closeness, and you know I’m here for that. 

Of course, some of you already adore anal (in which case, welcome to your celebration month!). So I’ve put together 5 doable anal adventures for every experience level. No need to run out and get the girthiest dildo ever (unless you want one, thank you very much), just take a look at the ideas below and see which one strikes your fancy. 

Butt first, your anal inspo….

1. Let Your Fingers Do the Talking

Experience level: Beginner

Supplies: Lube and gloves (optional) 

The anus has a high concentration of nerve endings – that’s why it’s considered an erogenous zone. So light, manual stimulation with hands and fingers is a great way to ease into things. With a partner,  remember to get consent before going there if this is something brand new in your sex life.

Because the anus does not self-lubricate, lube is a must for any kind of penetration. But an arousal oil like this one can also feel really good – which is reassuring if it’s your first time. 

For all my longed-nailed lovers, you can also wear latex or nitrile gloves if you like, which both cover fingernails and, if black, have the added bonus of looking hot. 

From there: 

  • Start by taking your fingers or even the edge of the palm of your hand and lightly rubbing or touching the area around the anus. 
  • You can work your fingers in a small circular motion. 
  • Don’t neglect the perineum, aka the area between the anus and the scrotum or vulva.
  • Try varying degrees of pressure and check in to see what feels good. 
  • As you move into the center of the action, penetrate very gradually. It’s natural to experience clenching at first, even if you’re stimulating yourself.
  • Rule of thumb (or…finger): if you’ve got a vulva, don’t switch from anal penetration to vaginal penetration and back. Keep things anal-focused to avoid infection!

If you’re flying solo, you can also use your other hand to stimulate your genitals. Which brings me to my next tip…

2. Plug In and Masturbate

Experience level: Beginner

Supplies: Lube and a non-vibrating anal plug

If you already love to masturbate but want to spice things up, this one’s for you. 

When you insert a small, non-vibrating plug into the anus while you self-pleasure, you get two cool benefits: 

  • You tone your sphincter muscles, making any anal play more comfortable and pleasurable
  • Your body gets used to having something “in there” while you orgasm

This is one of my favorite tricks to recommend to folks new to anal! It’s a wonderful way to acclimate to new booty sensations. Apply a generous amount of lube to the plug and to your body, and mindfully insert. (You can do this after you’ve already masturbated a little btw, to help you relax.) 

From there, masturbate to your comfort level…but ideally to orgasm. This way, you get to feel what it’s like to orgasm while you have something inserted in your anus. Feels incredible, and your body starts to associate the act with sexual pleasure. 

3. Make It A *Vibe* With Anal Beads

Experience level: Beginner-Intermediate

Supplies: Lube and anal beads

A sex toy that features a line of bulbs – often with a small bulb on the very tip – anal beads have progressively larger bulbs as you reach the base. They can be fairly flexible, with a cord-like structure that bends easily, or more rigid, like a traditional vibrator. 

But here is why anal beads are awesome! Because the first bulb is so small, beads are a great way to get your body used to anal play. As your sphincter muscles acclimate, you can insert the beads further, working your way up to larger sizes. 

2 ways to play: 

  1. Pops of pleasure. Removing the beads near orgasm can feel wildly pleasurable. They stimulate all the little nerve endings in your rectum and sphincter as you pull them out, creating a fireworks-like sensation. 
  2. Massaging your P-spot and A-spot. Once you’ve got the beads inserted deeply enough, the tip can stimulate your P-spot (prostate, if you’ve got a penis) or A-spot (anterior fornix, if you’ve got a vulva – it’s just behind your G-spot). Both can lead to super intense, internal orgasms you may have never felt before. 

LELO makes my favorite anal beads ever: SORAYA Beads. They’re designed for those just getting into anal, they look beautiful, and they’ve got a firmer construction – similar to a regular vibrator.  It’s got 4 beads, but 8 pleasure settings, so you can be really gradual with it.

Speaking of the beads on this toy: all of them vibrate. That’s actually a pretty special feature, since vibration helps your sphincter muscles relax. Perfect for insertion, pleasure and a left-the-planet orgasm.

4. Add Some Tongue

Experience level: Intermediate

Supplies: Lube 

Here is a partner play option for you. It’s oral sex on the anus, and I’ve got prep tips for both parties.

Most people’s main hesitation around anal is waste – which, I get. But it may reassure you to know that waste is actually not stored in your anus, it’s stored in your upper bowels. So the chances of a tongue interacting with it in a major way are quite low. 

Still, if you’re the receiver, it’s good to: 

  • go to the bathroom 30 to 60 minutes before anal play 
  • wash your entire booty (anus opening, crack, cheeks) afterward 
  • this makes everyone feel more comfortable and at-ease.

Lots of people like to explore this sex act while they’re giving “traditional” oral on the genitals. You can also apply flavored lube to the anus as part of the experience.

5. Peg During Partner Play 

Experience level: Advanced

Supplies: Lube and Strap-On Set 

And now: your advanced anal adventure. 

“Pegging” is a term that typically describes anal sex with a partner, who is wearing a strap-on dildo. I’ve seen this become much more popular over the years. Probably because word is getting out about prostate orgasms!

Still – just because you’re advanced doesn’t mean throwing caution to the wind. As with all anal, now is a time for lots of lube, and lots of communication. Pegging is definitely something to work your way up to after lighter, more gentle anal stimulation elsewhere in sex. More pointers: 

  • The person doing the pegging should get comfortable with their strap-on. That could look like walking around the house in it, to make sure nothing is chafing or feeling uncomfortable. What you want to feel is a firm, snug fit with your harness or underwear.
  • If you’re brand new to this, expect it to feel experimental at first. That’s because it is! With more experience, you’ll be able to sink into the moment.
  • For positions: ​​doggy style is a nice option, in all its variations. This allows easy access, and is definitely among the most comfortable positions for receivers.

For a more in-depth guide on pegging, check out this article here

Are you going on any anal adventures? Talk to me! Let’s meet up on my Instagram @sexwithemily and share our discoveries. 

Want more? Do yourself a booty-ful favor.. Get on the list for SmartSX, my *new* membership (coming soon)! We’ll be sharing our wins around anal play, our discoveries, and learning from experts. Anal is just one of the many topics the SmartSX community is exploring, and it’s fun because you get to chat with real people – who are learning and growing, just like you.