How To Have Anal Sex For The First Time — A 6 Step Guide

We’re always hearing that we could be having better sex, a better orgasm, or a better relationship. But how often do we hear the nitty-gritty of how we can actually better understand our deepest desires and most embarrassing questions? Bustle has enlisted Vanessa Marin, a sex therapist, to help us out with the details. No gender, sexual orientation, or question is off limits, and all questions remain anonymous. Now, onto today’s topic: how to have anal sex for the first time.

Q: I want to start experimenting with anal sex, but I've never done it before. How can I work my way up if all I've ever had in there is a finger? Is there a step-by-step process? What toys should I buy? Is there special lube? How do I know if it hurts too much or if I should push through any weird feelings?

A: Thanks for the question! More and more people are experimenting with anal play. Anal stimulation can feel a lot different than vaginal stimulation, and can have a greater potential for pain, so it's important to know what to look out for. Here are six tips to follow when you’re ready to try anal sex!

1. Start With Fingers First

You’ve already taken the first step of starting your anal explorations with fingers. For anyone out there who hasn’t tried any anal play, stick with fingers to begin with. Once you’re aroused and the two of you are already hooking up, have your partner put some lube on their index finger (more on lube in a minute), and press their fingertip against your anus. If that feels good, have them try slowly inserting a finger just up to their first knuckle. Over the course of several sessions, play around with inserting the finger deeper, and starting to move it in and out.

2. Try A Toy

JeJoue Mini Vibrator, $140, Amazon

Once you’ve had some experience with a finger and feel comfortable, you can upgrade to a sex toy. It’s fairly easy these days to find a beginner’s anal toy that will help bridge the size gap between a finger and a penis or strap-on. These simple and inexpensive butt plugs come in three different sizes: small, medium, and large. The small is perfect for anal newbies, and you can use medium and large to work your way up in girth. A weighted plug like the Pfun Plug from Njoy can help you get acclimated to an even fuller sensation.

Luxe Candy Rimmer Anal Kit, $19, Amazon; Njoy Pfun Plug, $55, Amazon

You can also try playing around with vibrating butt plugs. The vibration gives you more stimulation, and the added pleasure will help you relax and enjoy the experience more. At $140, this model by JeJoue is an investment, but it comes with a fun little app and remote control!

3. Use Lube

It’s absolutely critical to use lube during anal play, especially during anal sex. The rectum is not self-lubricating like the vagina, so attempting penetration without lube is going to feel very painful. You’re also likely to get small to moderate tears in your rectum, and let’s face it, is there anything less unpleasant-sounding than rectal tears?! Lube is a non-negotiable!

I like silicone-based lubes best for anal sex, since they tend to last longer and feel slipperier against the skin. You can find lubes specifically made for anal sex. They tend to be even thicker and more durable. Back Door by Pjur is a great silicone-based option. Even though it’s a water-based lube, the Jelle line from Wicked Lubes is an excellent choice.

Back Door by Pjur, $17, Amazon; Jelle line from Wicked Lubes, $10, Amazon

You can experiment with how much lube to use when your partner is using their fingers on you. Try having them put some lube directly on your asshole, as well as on their finger. When you’re ready to attempt anal sex, try using about a quarter-sized amount. Their entire shaft should feel super slick. Don’t be afraid of using too much! You can always have your partner wipe some off with a tissue.

4. Go Slooooooow

On the day that you decide to try having anal sex, take your time easing your way into it. Make sure you’re aroused and excited to take this step! It might help to have a vaginal orgasm first, but once you're ready, have your partner warm up your rectum with their finger first, to help relax your muscles and get the whole area nice and lubed up. When you’re ready to try getting penetrated by your partner’s penis or strap-on, pretend like you’re in slow motion and go as slowly as you can. Take deep breaths and try to imagine relaxing the muscles in your rectum as much as possible. You can speed up the pace once you feel comfortable, but it’s really important to take it slow for at least five minutes.

5. Be In Control

If you’re concerned about being in pain, you can also ask to be in control of penetration. This is easiest in doggystyle. Ask your partner to stay still on their knees, and allow you to push up against them. As long as you’re the only one moving, you’ll be able to dictate just how slow you go. Knowing that you’re in control may also help relax your nerves too.

6. Don’t Ignore Pain

The rectum is a tight little area. Getting penetrated there can feel uncomfortable, especially when you’re new to anal play. Since the area is so sensitive and susceptible to injury, it’s extremely important that you pay attention to pain. Don’t fight through it! If you think of pain on a 1-10 scale, I’d recommend slowing down if you feel anything above a three. If you’d rate it a five or above, I would think about stopping for a minute to take a few deep breaths and maybe adding some more lube. If the pain persists after a few breaks, stop anal play for the time being and try again next time.

Keep in mind that not everyone enjoys anal play, so don’t force yourself to fight through the pain if you’re not feeling any pleasure. Good luck!

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Images: Je Joue; Giphy