Curious about ass play but don’t know how to ease into it?

I absolutely love anal sex. Partly because I follow my own advice to make sure it’s fucking awesome every time. (Lube, anyone?!)

Try some of my tips to fully enjoy your next anal play experience.


If you’ve watched porn stars enjoying anal sex, remember that they’ve prepared for this and have enough experience with having anal sex privately before they decided to incorporate it during a performance.

Also remember that during a porn scene, the camera can start and stop repeatedly, and the footage is always edited. So you WON’T see a porn movie where the performer slows down, stops or adds lube. All of those things are normal and often necessary to achieving pleasure during anal.

So please, DO NOT take your anal sex cues (or ANY sex cues) from porn you’ve watched, or you’re probably not going to enjoy your sexperience.

Know That You CAN Have Orgasms Through Anal

Aside from all the nerve endings in and around the anus, anal play can also stimulate a vagina owner’s G-spot through the super-thin wall between the vagina and the rectum, along with other hot spots near the cervix. For prostate owners, there is much pleasure to be had via prostate massage, which can best be accessed through anal play.

The goal of any kind of sex should be pleasure, not orgasms. The best way to orgasm with anal stimulation is to incorporate other kinds of stimulation at the same time to the genitals. Achieving orgasms SOLELY through anal play IS possible, but much, much more difficult. Personally, I’ve had some of the most powerful orgasms of my life through anal sex, but it took practice and sticking with the tips I’m giving you here – so read on!

Experiment Solo First

If you’ve NEVER done butt stuff before, try it alone before you attempt it with a partner.

A good way to get started with anal experimentation is to incorporate it with masturbation. Try some external massage around your anus with a lubed-up finger, vibrator or butt plug before you try any penetration, to see if you like the way it feels. Chances are, with all the nerve endings back there, you’re going to enjoy some of the sensations. And if you don’t, that’s okay, too.

First, practice your breathing to properly relax your muscles. Once you’re ready and decide to penetrate yourself, START SLOW – there’s no rush – and go at your own pace. The benefit to playing with yourself first is there is absolutely no pressure, and there are no time constraints.

Anal Sex Anal Play Guide Sex Advice by Lexi Sylver
Photo of Lexi Sylver taken by Fabrice de Bray

Pick The Right Partner

I don’t recommend trying anal for the first time with a partner you don’t know and have never had sex with before. Probably best to steer clear of doing this for the first time during a one-night stand or group sex experience.

If you really want to enjoy your anal adventures, your partner should be someone you’re already comfortable playing with, someone who knows you, your body and your boundaries.

You can always try playing with your ass in front of your partner or having them incorporate anal play into your repertoire for awhile before you decide to achieve full-on anal penetration. This way, you can start to feel more comfortable with your partner around your backdoor area, and they can start to learn what you do and don’t like back there.

Let me also just say that it’s best to try anal for the first time with someone who doesn’t have a massive dick, or make sure your partner is using a small or medium-sized strap-on. IF your partner is particularly well-endowed, make sure you’re practicing with anal toys or an anal training kit for awhile first before you get started with full-on penetration.

Get The Mood and Setting Right

Make sure you’re somewhere comfortable, and you’re not pressed for time so you can truly relax. Don’t forget that when you’re tense, your muscles (and ass!) will tense up, too. For optimum pleasure during any kind of sex, but especially for a tight-assed beginner, you want to be as relaxed as possible.

If you’re worried things might get messy (which they might, even if we’re just talking about getting lube all over the place), set down a dark towel over whichever surface you’re using.

Always make sure tissues and/or unscented baby wipes (recommended), and lubricant are within easy reach!

Prepare Yourself

Everyone always worries about things getting messy when you stick anything into your poop chute.

To reduce the chances of that happening, before you start anal play, try to clean up your ass as much as possible.

An easy way to do this is with an anal douche, using warm water (no chemicals necessary!), and repeat as many times as necessary until you feel that the inside of your ass is clean.

For prolonged or super deep anal sessions, I recommend giving yourself an enema (which will clean more deeply into your bowels / large intestine than an anal douche, which will simply rinse out your rectum).

Start Slow and Ease Into It

Another reminder to always LUBE IT UP!!!

The best anal sex will come if you’re already turned on from other kinds of stimulation. Start with vaginal sex and lots of foreplay to help you relax and get into the groove before you start with anal sex.

It’s also best when you can go at your own pace and be the one to control the movements of penetration so you’re most comfortable. Just like when you were playing with your ass solo, start slowly, one inch at a time, until you feel more comfortable. Start with slow and shallow strokes before you go deeper.

Lexi Sylver Anal Sex Guide Anal Play Butt Stuff
Photo of Lexi Sylver taken by Fabrice de Bray

Stimulate Other Areas Simultaneously

I always recommend playing with other areas while you’re engaging in anal sex to heighten pleasure and increase chances of orgasm: your partner’s clit, vagina, breasts, dick, balls or perineum… any and all other areas are welcome!

You can also stimulate other spots, like your partner’s neck, mouth, ears, scalp, inner thighs, feet… the list goes on! Nerve endings are everywhere, just begging to be stimulated, and you can evoke an even more visceral sexual response.

By expanding your focus beyond your/their ass, you, your partner, and all your muscles (and brain) will start to relax.


This goes along with choosing the right partner, but you NEED to communicate with them throughout the session. Your partner WANTS your experience to be good. Let them know if it feels good, when they can go faster or deeper, etc.

Communication is the key to great sex – any kind of sex!

Add LOTS of Lube

Did I mention to keep adding lube all throughout your anal session?

Don’t be shy – squirt that stuff over and over again!!!

You can use any kind of lube (if you’re using condoms, don’t use oils or oil-based lubricants, as these can weaken the latex). You can experiment with different lubes until you find the one you like best. I personally opt for water-based lubricant, which works with virtually all toys and condoms.

Don’t Double Dip

Do NOT switch from anal to vaginal sex in the same session without cleaning up in between. EVER. If you’re using condoms, switch the condom between holes. Otherwise, you’re risking exposing the vagina to harmful bacteria, which can cause unpleasant infections later on.

I’ll repeat this again, louder for the folks in the back: DO NOT DOUBLE DIP. I don’t care if you saw it in porn. Just. Don’t. Do. It.

Don’t Be Afraid To Stop

No matter what you’re doing sexually, you should never be afraid to tell your partner to say stop and pause or end the session at ANY point in time. This is especially true during anal sex. If it hurts at any point, you should stop. If you want to take a break, and/or focus on other parts of your body, feel free to do so!

Don’t Be Embarrassed

Shit can happen – literally. So can farting and other fun noises (like queefing!) that can occur during sex. And that’s totally normal and okay! Just laugh it off, take a break, and/or continue the fun.

So grab the lube and get down and dirty with some anal play tonight!

For more sexy news and tips, subscribe to my Lexual newsletter.

Until next time, Stay Lexual, my friends and fiends.


Featured blog image of Lexi Sylver was photographed by Fabrice de Bray