You’re ready to get to the good stuff, but you want to be prepared. There are plenty of ways to do anal sex wrong on your first try. 

We’re going to talk about how to do anal sex the right way your first time. 

This article is the final piece in our exhaustive Anal 101 series. We strongly suggest you read the previous three parts so that you have all the information you could ever need:

Part 1: Anal Anatomy

Part 2: 6 Steps of Anal Douching

Part 3: Anal Training in 5 Steps

Remember that time, patience, and preparation are all equally important. Don’t rush yourself, and don’t let anyone else push you. 

All products recommended are personally selected by me, Elaine S. Turner. I choose them and genuinely believe in them. However, this article may contain affiliate links. That means if you use that link to buy a product, I may earn a small affiliate commission, or tip, as I like to see it. You can learn more here if you have any questions about my affiliate policy.

Anal penetration supplies

Anal sex, like any other kind of sex, is much better with some preparation and materials on hand. If you want your first anal penetration experience to go as perfectly as possible, make sure to have these:

Plenty of lubricants 

Make sure you have something with a one-handed pump as well. Using only one hand will help prevent the spread of any fecal matter onto your lubricant container. We suggest using a silicone-based lubricant.

A towel or “sex sheets”

During anal penetration, shit happens. Not all the time. But being prepared for it and not having to stop because of a minor accident can make all the difference. You can lay down on a towel, use a dedicated set of sheets, or get water-proof  sex sheets from your adult store. Whatever makes you feel comfortable.

Any sex toys 

You’re going to want to repeat the anal training process before full penetration. You’ll want to move through your plugs and stretch yourself out before a penis, dildo, or vibrator enters you. Make sure to keep stimulating yourself during penetration as you did during training. 

Cleaning supplies 

You can never be too prepared. Having condoms, wet wipes, towels, or anything similar can make cleaning up fast and easy.

Anal penetration preparation

Being prepared is multidimensional. Having the right supplies is crucial, but so is the way you frame the experience for each other. 

A safe word

Pain is possible during anal penetration. Choosing a word ahead of time to communicate that you’re uncomfortable ensures maximum safety. Make sure to select a term that isn’t usually said during sex, like “pineapple” or “SpongeBob.”

A conversation or two

Talking about how you want things to go beforehand means nothing is left to chance. Discuss how the penetrator will proceed, what they’ll do during ejaculation, and what to do if you’re in pain. 

Douching 

For full penetration, it is generally ideal to douche your anus. You can follow the 6-step guide here. 

Clean-up 

If you’re using toys, make sure you clean them entirely as soon as you’re finished. Same with any residue that is on the sheets.

Shit happens 

Relax about the poop factor. It isn’t that big of a deal, and if you play with fire, well, you know the saying. 

Quick rule reminder

There are some rules you should be aware of when it comes to anal:

• Foreplay is a must. 

  • 10-15 minutes of kissing and cuddling 

  • 10-15 minutes of genital play, then as much anal toy usage and play as you can provide

  • 15+ minutes of anal warm-up with rimming, finger play, and toys

• Do not pull anything out of the anus quickly. That is how accidents happen.

• The bottom is always in control. Let them move on the penis or dildo rather than the other way around.

• It may not happen on your first try, that is okay! Patience is key to a pleasurable experience.

• Vagina to anus is okay. Anus to vagina is not. 

• Always use condoms, even if you’re in a long-term, monogamous relationship. They’ll make cleaning up easier and help keep everyone safe.

• Anal sex isn’t supposed to be painful. If you’re experiencing intense pain during anal penetration, go back to play and training.

• Keep adding lubricant. Your anus does not make lube. You’ll need a lot more than you think.

• Continue to stimulate the bottom’s external genitalia during penetration. This will help keep them both relaxed and aroused.

• Do not just shove it in. Ever. Under any circumstances.

• If the penetrator or top has a penis, there is a risk of them ejaculating. With this comes uncontrollable hip thrusts that may be uncomfortable to the beginning bottom. Talk about what you can do to avoid this.

How to have anal sex

The person being penetrated (the bottom) is going to be fully in charge. 

1. Get into a doggy style position with the bottom on their hands and knees

2. Apply a generous amount of lubricant to the penis and the anal opening

3. The top should position the tip of their penis at the anal opening

4. The bottom should slowly push themselves back onto the penis. Let them take as much time as they want and need for every millimeter

5. When there is discomfort or pain, stop and breathe. You can slowly pull yourself off the penis or continue once you’re comfortable

6. While the top stays still, let the bottom explore the sensations of having a penis inside them for the first time. The bottom should go as slowly throughout the first session. 

Remember that the first time may not work out, and that is okay. Full penetration may take several attempts to do. Same with allowing the top to be in charge of movements, let the bottom be in control. They’re the ones who need to be entirely comfortable. 

That’s it! If you enjoy it, keep doing it! You’ll find it gets easier and more pleasurable over time. If you didn’t get the whole penis inside you on the first try, you’re in the majority of people. Again, time, patience, dedication, and proper arousal are all key for learning how to enjoy anal. You’ve got all the time in the world, so use as much as you desire!

If you’ve followed the step-by-step guide and are still having difficulties with anal sex, get in contact with me today!

“Teamwork begins by building trust. And the only way to do that is to overcome out need for invulnerability.”

—Patrick Lencioni

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