You might be a beginner at butt pleasure or an experienced anal adventurer who is hungry for more. Either way, exploring anal sex can feel really exciting and it can also bring up feelings of shame, stigma and insecurity.

Every body has a butthole - it’s the great equalizer! Different buttholes like different things, and there are techniques to maximize pleasure and minimize pain and discomfort. 

So, if you’ve never considered having anal sex, or are afraid to try it, then this guide is for you. This guide is also for people who are interested in discovering anal sex and other ways to reach new kinds of pleasure. Everyone is welcome.

CONTENTS

1. A lot of lube

2. Communication is the ‘social lube’ 

3. Anal doesn't have to be PAIN-al

4. Cleaning your ass

5. Set the mood and engage in foreplay

6. Start slow

7. Penetrate slowly

8. Go deeper

9. Speed things up

10. Go as deep as your partner is comfortable

11. Mark the depth

12. Finish things up

13. Talk things through

1. A lot of lube:

It might be a really hot fantasy to approach someone and slip into their anus effortlessly, but in reality, surprising someone with anal penetration can hurt them and make them feel unsafe. Consent is a thing. Anal training is a thing –– and you can train a butthole by using butt plugs, anal beads, or prostate massages, to slowly help the ass get comfortable with penetration over time.

A few minutes isn’t enough of a warm up for anal sex. Take advantage of all the nerve endings around the rim of the anus. Take your time, arouse the ass externally and anal penetration might be on the menu or not - you can have lots of arousal from non-penetrative anal stimulation.

To warm up the anus, grab some lube and with your partner’s consent try:

• Rubbing the butthole with your thumb or knuckles and massaging the butt crinkles

around the anus.

• Rimming the anus feels great for lots of people and can help your partner relax.

• Using a vibrator pressed against the anus or the perineum (the skin between the

genitals and the butthole).

• Exploring anal masturbation allows you to go at your own pace and see how your

body responds.

Spit might be cute, but it’s not lube.

The anus isn’t self-lubricating, so lubrication is a must.  Lubrication creates a slippery texture to minimize friction (and injuries) during penetration with sex toys, fingers and penises.

Use a long-lasting lube and remember to re-apply during the course of penetration! 

2. Communication is the ‘social lube’:

Though you need actual lubricants, communication is just as important to make sure everyone is having the best anal time possible.

Have an open conversation outside of your sexy time. Talk about concerns, fantasies, boundaries, who’s the giver/receiver and turn ons/offs. Are you worried about hygiene? Anxious about discomfort? Prefer rimming to penetration? It can put both partners at ease to have playful and curious conversations so you know what pleasure is possible. 

3. Anal doesn't have to be PAIN-al:

   

Previous painful experiences or assumptions that anal has to hurt, might cause someone to feel nervous about anal sex. A body that is tense, worried or insecure can prevent the anus from relaxing. Encourage the anal receiver to control the depth and speed of penetration by holding still and letting them ease down or back onto penises, sex toys, or fingers. It’s important that the receiver trusts that the giver will promptly stop penetration if pain arises. 

For many people, arousal takes time to build. Once you start engaging in foreplay and teasing, things are already on the way and building toward something incredible. Imagine that you and your partner have started engaging in foreplay. You’re both hot and bothered. You have taken each other’s clothes off. Things are heating up fast. Then you back away and go off for a few minutes to fiddle with a sex toy, some cream, or to struggle to rip open a condom…and the moment is ruined.

So, before you engage in foreplay, get everything ready and make sure that it’s within reach. When the time comes, you don’t want to get interrupted, and neither you or your partner will be very patient.

Remember that anal sex is available to every kind of couple. You can use sex toys to stimulate and penetrate someone anally and it’ll be just as pleasurable for that person as it would be with a penis.

So, if you’re going to be using sex toys, get them out and get them ready before you engage in foreplay. If you’re going to be wearing a strap on, then put it on before things kick off.

4. Cleaning your ass:

   

The rectum’s main job is getting waste out of the body, so when you start to explore anal

pleasure, obviously poop is a reasonable concern. Here are some options for anal sex

hygiene:

• Use an enema bulb to flush out the rectum with warm water. Do not use douching

solutions - they often contain ingredients that irritate the delicate tissue inside the anus. 

• In the shower, you can clean externally and optionally use a finger one to two inches

inside your ass to flush out any remaining particles from your last bowel movement. If

you’re using soap, use a gentle, moisturizing and unscented soap.

• Put down a towel for anal play, and keep wipes nearby.

The anus has different bacteria than the vagina and urethra - so it’s best to keep butt stuff

in the butt. You can use barriers like covering butt toys with condoms, fingers with

non-latex/latex gloves, and preventing oral exchange of bacteria through dental dams.

5. Set the mood and engage in foreplay:

You should look at anal sex as a part of a bigger sexual intercourse session. If you rush into it, you might ruin the moment. Setting the right mood can do wonders for the arousal and enjoyment of all parties involved. Sex is meaningful, wonderful, and exciting. You shouldn’t get to the good part just to get it out of the way. You should build up to it and treat it like a climax. So set the stage for a lovemaking session that will entertain and pleasure all parties involved. Make things fun and special. Light some scented candles. Put on some music. Break out your favorite sex toys. Grab some chocolate syrup and whipped cream from the fridge. Make an evening of it and build up the anticipation for the main event. It’ll make things much more meaningful, trust us.

Once both of you are aroused and having the time of your lives, you can move on to the next step.

6. Start slow:

Now that you’ve engaged in foreplay, things are heating up between you and your partner. The excitement is building, your hearts are racing quicker, your bodies are getting hotter, and you’re getting closer and closer to experiencing anal sex.

It’s important to savor the moment and start things off slowly. Start off by massaging the area around your partner’s anus. Caress their behind, play with their cheeks, stroke their skin. If your partner is comfortable with spanking (ask them first), then go ahead and spank them softly at first before increasing the strength of your slap. Ask them if they want to be spanked harder or if you’ve spanked them too hard.

Now, stimulate the skin around the anus. You can do this with your hands, your tongue, or the tip of your penis or a dildo. Move slowly at first, then speed up and work your way toward the center of the anus.

7. Penetrate slowly:

Now that you’ve worked your way to the center of the anus, move past the point of entry and gently penetrate your partner from behind. Explore this new threshold slowly and gently. Take your time. Make sure your partner is comfortable with how things are moving and how fast they’re moving. You don’t want to surprise them now, they’re in a vulnerable position and they’re trusting you to make things enjoyable for the both of you. Stay at this initial depth for a bit, pleasuring and stimulating your partner here the same way you would stimulate the vagina just past the lips.

8. Go deeper:

Once you’re sure that your partner is comfortable, you can start to go deeper. Remember to move slowly. You’re treading new ground. You can go pull back to the first area you were exploring and then penetrate slowly just beyond that point. Stimulate these shallow depths for a while and, when your partner is ready, get ready to go deeper.

Now penetrate deeper and deeper, still moving slowly, and start asking your partner if they’re comfortable. You want to stay on as straight as a line of exploration as possible here. If you penetrate and then start moving from side to side or changing your angle of entry, you might make your partner uncomfortable or hurt the inner skin of their anus. Be gentle. Move slowly. And stay on the right path.

9. Speed things up:

Before you go any deeper. Start pulling back and then penetrating to the point you were at before. You can start speeding up now, but listen to your partner and ask them if they like how you’re doing things. Remember, you can speed up to get to any point you’ve penetrated to before, but you should always slow down before penetrating to a new depth. Your partner may have never been penetrated anally before, so their inner anus will be tight and hard. If you penetrate too deep, too fast, and too strong, you can tear this inner skin and it’ll be very painful.

10. Go as deep as your partner is comfortable:

Now that you’ve penetrated your partner a few times at the same depth, slow down and penetrate deeper. Move slowly and keep penetrating. Ask your partner to tell you when to stop. There will be a point where their skin will be tender because it’s tight and has never been penetrated (if they’ve never had anal sex), so they’ll tell you when to stop or to pull out if they’re uncomfortable.

Keep moving deeper and pulling back or stopping when your partner tells you to. The important thing is to find a depth that your partner is comfortable with. They’ll tell you the right depth to keep things at for now.

11. Mark the depth:

Remember the depth that your partner said they enjoyed most and stay there. This is easier to do if you’re using your penis because you can feel this spot on the inside. If you’re using a dildo or strap-on, make sure to remember where you were holding it or how much of it you could see when your partner told you to stop.

Congratulations! You’ve discovered and explored uncharted territory with your partner. This is a good place to stop for now. You can explore this depth, but remember that the inner walls of the anus are delicate. Don’t try to change your angle of penetration to hit the inner lining, as this will be painful and can cause a rupture, but you can explore up and down by moving slowly and asking your partner to tell you if it’s comfortable.

12. Finish things up:

Keep penetrating to your partner’s preferred depth until you’re both satisfied. Remember to communicate with your partner and listen to them. If they want you to keep going, you should move slowly again as you penetrate deeper. If they want you to stimulate them in another way, then do so until they come. Like any kind of intercourse, the aim here is for both of you to orgasm. Don’t be disappointed if your partner doesn’t orgasm from anal stimulation. You’re trying something new here. If you come before they do, you should stimulate them in a more familiar place and make them come that way. If you don’t know how to make them come, ask them and they’ll tell you where to go and how to move when you get there.

13. Talk things through:

Communication is key. After you and your partner are done, remember to talk things through once again. Ask them how they felt during the anal penetration. Did they like it? Was there anything about it that they would have liked differently? Were you moving too fast? Were you too harsh? Would they like to try it again sometime?

The more you and your partner communicate, the more you’ll know each other’s preferences, and the better you’ll make each other feel.

That about does it! You and your partner have now experimented with anal sex. From here, you can try new things, go deeper, and use different methods to stimulate your partner anally. Always remember, however, that you should move slowly and gently whenever you’re penetrating to a new depth and that you should talk things through before and after sex.

The butt likes to be seduced. Go slow, use lube, talk to each other, let go of of penetration expectations, and get curious about what anal pleasure possibilities are available to you!