Beginners Guide to Anal Sex Advice at Sh Women's Store Beginners Guide to Anal Sex Skip to content

FEMALE-FOUNDED LGBT+ INCLUSIVE

Beginners Guide to Anal Sex

Published : Updated :
Beginners Guide to Anal Sex - Sh! Women's Store

Anal sex is one of the topics we get asked most about - it seems you are all curious about how to pleasure the butt! Porn may have you believe that a girthy penis or dildo will slide right in, but... that's not the case. It takes time. You need to seduce that ass.

Learning about your butt and its likes and dislikes on your own gives you a greater chance of a pleasurable and pain-free experience with a penis or strap-on.

Here's our guide on how to make your first time anal sex a pleasurable experience. 

Lube is essential for anal sex

The ass isn't self-lubricating, which is why anal sex can be so painful. Lube is a must. And lots of it! We recommend using a lube for anal sex. Anal lube is thicker and more long-lasting. 

a bottle of Sh! pure plus anal lube

 

Some customers want a numbing gel alongside their lube, but we don't recommend - or sell - numbing products. Pain is your body's way of telling you that something is wrong. Overriding this function with a numbing gel can cause internal damage, so our stance is simple: Don't do it.

Start with a fingertip

Make sure you are fully aroused before sliding your attention towards the butt. Play with nipples, clit, penis and other body parts that feel good. The more turned on you are, the more pleasurable anal stimulation will feel.

Latex gloves make fingers feel smooth and help protect the delicate anal area from snaggy or long nails. Using gloves will also make you feel more relaxed regarding any hygiene issues.

Start gently with a well-lubed and gloved finger. Stroke and massage the anus, tease and tickle. Apply a little pressure on the anus when you feel ready for more. Breathe deeply and let the fingertip pop inside.

Explore the sensations. The more relaxed you are, the easier it will be to glide the finger a little bit deeper into the butt.

Moving on to anal sex toys

Your butt needs to be really relaxed before you insert something. The rectum has two sets of sphincters. The first set can be relaxed pretty much at will, but the second set may need some convincing. Trying to push through the second sphincter before it is ready will cause pain. If the ass doesn't invite you in, you need more time, more lube, and more play.

As long as your first anal sex toy is slim and has a flared base or looped handle, it's up to you whether you prefer a butt plug or an anal dildo.

A small butt plug is a good starter toy. Butt plugs are designed to stay in place rather than being moved in and out. They help you get acquainted with the muscles in your bum and the sensations on offer. Squeezing and releasing against a butt plug teaches you how to gain better control of your anal muscles.

An anal dildo is designed to be moved in and out. Practising with a dildo gives you greater control and builds confidence. We recommend practising with dildos of varying sizes if you're hoping to go on to anal intercourse with a penis or a strap-on.

four black butt plugs in graduating sizes

 

Coat the insertable part of the toy with anal lube, and gently push it against your anus. Once the sex toy glides in, we recommend keeping it still for a while. Give yourself some time to become accustomed to the sensations - it tends to feel "backwards" at first. This is normal. 

Anal sex positions

If you decide you are into anal play and want to try full intercourse with a strap-on or penis, we have some advice about anal sex positions.

Most vaginal sex positions can be adapted into comfortable anal sex positions, but we think cowgirl/cowboy is an excellent way to explore anal penetration. Taking charge and being on top rather than opting for traditional doggy style gives you more control. You can decide on depth and speed or take a break and sit still whenever you like. 

As your confidence and love for anal pleasure grows, you can experiment with different positions :)

Read all our anal sex advice here.

Leave a comment

Please note, comments need to be approved before they are published.

Loved Anal Toys

Meet the anal toys our community loves most. Considered design, gentle options and confidence-boosting pleasure.

EXPLORE THE FULL RANGE >>
  • Wirly 2 Slim Dildo
    £39.00
  • Cupid 2 Curved Silicone Dildo
    £35.00
  • Flirts Small Silicone Butt Plug
    £18.00
  • Wirly 2 Slim Vibrating Dildo
    £49.00
  • Wirly 1 Slim Dildo
    £29.00
  • Cupid 1 Curved Silicone Dildo
    £25.00
  • Beginners Butt Plug 1
    £23.00
  • Perfect Angle Anal Douche
    £16.00
  • Your Guides to Anal Pleasure

    Explore more articles dedicated to anal pleasure, and discover everything you need to know about enjoying sensual, comfortable, pain-free anal sex.

    Tushie love is a subtle art — one that can unlock deep pleasure and seriously satisfying orgasms - yet it’s still surrounded by mystery and taboo. So to every body with a bum (that’s all of us), we say: go forth and explore. You’ll find thoughtful, reassuring advice right here.

    ALL ANAL PLEASURE ADVICE >>
    What is Anal August? - Sh! Women's Store
    What is Anal August?

    What is Anal August? (Dear reader, isn’t this an interesting question!) There is Masturbation Month, Orgasm...

    Q&A: Is It Safe To Wear A Butt Plug All Day? - Sh! Women's Store
    Q&A: Is It Safe To Wear A Butt Plug All Day?

      Hey Sh!  My partner gets really turned on whenever we do anal stuff. We work...

    Q&A: How To Try Solo Anal Sex With Only Lube And No Toys? - Sh! Women's Store
    Q&A: How To Try Solo Anal Sex With Only Lube And No Toys?

    Hi Sh! I'm curious about anal sex and I'd really like to try it, but I don't know...

    Safe, Sensual & Pain Free Anal Play for Beginners - Sh! Women's Store
    Safe, Sensual & Pain Free Anal Play for Beginners

    If you're a beginner to anal, but curious to try it, you're in the...

    Enhancing Anal Play & Pleasure with Lube & Latex - Sh! Women's Store
    Enhancing Anal Play & Pleasure with Lube & Latex

    Anal play should be pleasurable. Read our article on how to eliminate pain and ensure there is only...

    How to Use a Butt Plug for Anal Pleasure - Sh! Women's Store
    How to Use a Butt Plug for Anal Pleasure

    This article shares tips & advice for how to choose and use a butt plug for anal pleasure. 

    How to Use Anal Vibrators - Sh! Women's Store
    How to Use Anal Vibrators

    Read our article with advice on how to choose and use anal vibrators safely here.

    Relaxing Anal Muscles - The Key to Pain-Free Anal Sex - Sh! Women's Store
    Relaxing Anal Muscles - The Key to Pain-Free Anal Sex

    Relaxing your anal muscles (and using lots of lube) is key to pleasurable anal sex.

    Lube for Anal Sex - Sh! Women's Store
    Lube for Anal Sex

    Before you go dipping your anal vibe,

    Q&A: How to Assfinger with Long Nails? - Sh! Women's Store
    Q&A: How to Assfinger with Long Nails?

    Dear Sh!Whilst making love, my lover likes me to slip a finger in their ass but my nails...

    Q&A: Does Anal Sex Hurt? - Sh! Women's Store
    Q&A: Does Anal Sex Hurt?

    We answer a customer's question with advice on how to have pleasurable and pain-free anal sex.

    Positions for Anal Sex - Sh! Women's Store
    Positions for Anal Sex

    Read our advice on the most popular, most comfortable positions for penetrative anal sex.

    Anal Sex, Toys & Pleasure for Every Body - Sh! Women's Store
    Anal Sex, Toys & Pleasure for Every Body

    Tips and advice on how to choose and use anal sex toys for pain-free and intense pleasure.

    How not to lose an anal toy & what to do if one does 'get lost' - Sh! Women's Store
    How not to lose an anal toy & what to do if one does 'get lost'

    This article advices on how to play with anal toys safely - and what to do in the...

    How To Have Safer Anal Sex - Sh! Women's Store
    How To Have Safer Anal Sex

    This article shares advice on how to have safer, more hygienic and comfortable anal sex.

    Q&A: I'd Love To Have Anal Sex With My Wife - Sh! Women's Store
    Q&A: I'd Love To Have Anal Sex With My Wife

    Read our advice on how to gently introduce the topic of anal sex to a partner here.

    Like tailored anal pleasure advice? Ask us.