“Erin, please educate me on BUTT STUFF. I’ve tried anal before but I didn’t enjoy it. I think we were doing it all wrong, too much too fast. I have a butt plug but I don’t find it comfortable either. Please tell me how to start and how to learn to like it – I hear it can be so fabulous and I want to experience that! Help!”

                                                           – Bootylicious

Dear Bootylicious,

So…you want to try anal sex.

First of all – you’re not required to like anal sex. I’m sure you realize that but just in case you didn’t, I had to say it. Know what you like, try anything once, and don’t be ashamed if you don’t like it. Being willing to try something more than once is admirable, but don’t force it or shame yourself if it just doesn’t happen.

I would also suggest evaluating your reasons for wanting to try. To please your partner? Noble, but remember your own pleasure too! Both of you will be happier and more satisfied if your (and their) intentions are a mixture of wanting to give AND receive pleasure.

And without further ado, here it is…

Erin’s Thoughtful Guide to Anal Sex for Good Boys and Girls

Pre-game: Empty the bowels either naturally or with an enema. It’s not necessary every time, but it may make you more comfortable and receptive if you’re all cleaned out. Anal sex is usually much better when you’re not literally full of shit.

1. Foreplay. Make sure you’re so fucking horny you can’t stand it. Ask your partner for whatever you need to get turned on, whether that’s just making out or full-on vaginal intercourse. Having your ass eaten is an also excellent way to get you ready.
2. Warm up the asshole. Prep with fingers, toys, a butt plug. Massage it to relax it. Don’t force it.
3. Lube. Whatever your lube of choice is, make sure you have easy access to it. There are different brands of lube with lidocaine in them to make the asshole a little numb. Remember there’s a risk of penis getting numb in the process (assuming you’re being penetrated by a human dick and not a strap-on or other toy). Use a condom to avoid that numbness and for extra sliding power. My preferred lube is coconut oil because I’m a crazy yoga hippie.
4. Position. You might be most comfortable if your legs are in a squatting position, but the most important thing to remember is to try different positions to find what’s best for you. Try on your back, on your knees from behind, on your knees on top. Make sure you’re comfortable.
5. Control. I suggest you have most of the control as the penis or toy first goes in. Once the head is in, it should be much easier and feel better. Change positions of you need to. Keep trying. It will get easier.
6. Pleasure. Your pleasure. Once it’s in at least half-way, get the vibrator, rub your clit, make your partner lick your nipples. Do whatever you need to do to get horny again if you lost it.
7. Movement. Let your partner move a little. Gently at first, then harder. The more it moves, the more it presses the right buttons, and the better it will feel, trust me.
8. Communication. Talk during and after to make sure your comfort and pleasure are a priority. If at any point you need to stop, tell your partner.

Post-game: Go to the bathroom. Check for tears and bleeding. Notice how you feel physically, mentally, emotionally, and spiritually. Communicate how you feel. Maybe write about it.

I hope this helps. I’d love to hear about  your experiences or if you have anything to add to this list. Happy butt sex!

With curiosity and love,

Read more about my thoughts on anal sex here!

Want to submit a question? Send it to with Ask Erin Anything! in the subject line or fill out the contact form here.

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