Prepare For Anal Sex: How To Ask For Anal & What Comes Next

By: Melissa Miller , September 27, 2023

When Wayne Gretzky famously said, “You miss 100% of the shots you don’t take,” he probably wasn’t referring to anal sex, but he might as well have been. It’s not just a great piece of motivational wisdom, but a universal truth that the only way you can acquire some things in life (without being offered) is by shooting your shot. And every great player knows, whether it’s hitting slapshots or asking your partner about anal sex, your best bet is to put yourself in a position to score.

Prepare For Anal Early On

Before the conversation itself and your own reflection and research on the pleasure part of anal sex, addressing hygiene and safety is important. Regularly getting tested and barrier methods are important for STI prevention.

Hygiene is also important to consider, whether that’s a bathroom break and shower beforehand or simply knowing someone’s mind may be in the mood for anal sex but they’re body isn’t. Even if you’ve had anal sex before, each partner is a new situation that should be handled, spoken to and heard as if it’s brand new.

Assess Your Desires Before Asking For Anal

So, you know you want to ask. You’ve either done it with another partner in the past or you want your current situation to allow you to forge into this uncharted territory for the first time. If you don’t do well with rejection, I’m going to go ahead and recommend against bringing up your desire to penetrate your partner’s asshole with your penis for the first time while you are in the process of having sex.

The idea behind figuring out why you want to try anal is specifically to be able to communicate it in a way that isn’t completely self-rewarding. Consider if she frequently climaxes when you have sex. If not, perhaps a preliminary conversation should revolve around how to cater to her sexual needs. Granted, not all women orgasm during sex, but investment in her pleasure and a concerted effort to get her there won’t go overlooked.

This will take some self-reflection. Straight men largely have a reputation for prioritizing themselves during sex, so before popping the question, you might want to do some research and determine your lover(s) perception on where you fall on the taker-to-giver scale. Takers will immediately be perceived as asking with nothing beyond their own dick in mind. Givers are in a better position with anyone who may be a little apprehensive but curious nonetheless. Be a giver.

If you don’t give enthusiastic cunnilingus, learn. If you can’t find the clit, start a search party. Immediately. If you haven’t consistently exhausted every avenue of making sure she is satisfied in some way, shape, or form, go ahead and consider this a prerequisite before you ask for anal, or anything outside the realm of normal sex between you. Ultimately, you want her to have faith that you will make this extremely enjoyable.

If you really want to knock her socks off, in addition to figuring out why you want to do it, putting it into words, and making sure it’s for her pleasure as much as your own, educate yourself on anal sex and how to prepare for it.

Showing you’ve done a little research on things like how to prep or ease into anal, to avoid numbing lubes and what types to consider, that clitoral stimulation in addition to anal penetration will help for her pleasure, and if you want to consider a butt plug during foreplay, is not only sexy but will really allow her to trust you even if neither of you have ever done it.

A great resource is Tristan Taormino’s book, “The Ultimate Beginner’s Guide to Anal Sex for Women, 2nd Edition.”

You’re going to approach this thoughtfully, so here are a few things you need to consider!

As mentioned, make sure to start the conversation outside of a sexual session.
Make sure you afford her time to think about it as you’ve also taken time to consider your own desires around anal sex before bringing it to her.
You can make it a larger conversation about desires and fantasies and include anal sex into that conversation.
Consider asking about toys or butt plugs to start and ease into full on anal sex.

How To Ask For Anal The Right Way

Sometimes, it seems as though men don’t think about consequences or consider all of the possible outcomes as much as women, so a spontaneous request while inside of her probably hasn’t accommodated the possibility that she will say anything aside from yes. Let’s avoid this.

When you do find an opportune time to ask, she may respond yes, no, maybe… or why?

Will you have an answer?

It will feel good, right? Because you saw it in a video? You’ve done it before and liked it? It’s… tighter… you heard?

You wouldn’t ask for a sandwich without being hungry, and you wouldn’t request a raise without knowing why you deserve it. Ask yourself why you want to have anal sex, so you can communicate that you want to try anal for the first time with her.

Some Red Flag Responses To You Asking For Anal Sex

This is not to make you feel abnormal, by any means. According to the CDC, 30-40 percent of men and women enjoy anal sex. You simply should be able to articulate why you want to do it and determining this will make discussing it easy, but here are some things to keep in mind during and after the discussion:

If she says “maybe,” but never brings anal sex or the conversation up again, it’s not a yes and that’s what matters.
If she shares a bad experience she had with anal sex and doesn’t say she’s open to trying it again, it’s a no.
When you ask about anal sex and she completely avoids the conversation or changes the subject, she’s not ready to discuss it.

It’s very possible none of this will matter. She might just be down to do anal with you! Regardless, it’s definitely worthwhile to take the time to have these conversations. Not only does it show you care, but it could take a partner from a maybe, to comfortable, to interested, or even begging for it.

How To Prepare For Anal Sex Quickly If She Says Yes!

So, how do you prepare for anal if she’s quick to say yes? First and foremost, safe sex is always important. Barrier methods of protection like condoms are the way to go here. Additionally, aside from protection, in terms of safety, you should come across major no-no’s in your research. While having intercourse, it’s crucial to know you shouldn’t be going butt to mouth or butt to vagina due to bacteria that could be transferred during the act.

Make sure you do these things if you’re both ready right away:

Because the anus doesn’t lubricate itself like the vagina, lube is essential. You’ll want to lubricate both the penis (or any toy, butt plug or dildo) and the anus.
Just because she can’t get wet on her own, doesn’t mean you skip foreplay. It is always instrumental for relaxation, enjoyment and pleasure.
Lastly, to prepare for anal sex, you’ll need to keep in mind clean-up and aftercare. You can shower together, but if not, you’ll also want to have wipes on hand and wash up both parties afterward.

Final Thoughts on Preparing For Anal Sex

The bottom line is you’ll want to take it slow. Ease into both the conversation, and if she says yes, the act itself. And last, but furthest from least, consider the possibility that even if you have the talk, get a yes, and handle the experience with the utmost care, it might still hurt, and you might need to stop, especially if it’s the first time.

After accepting this, you’ll be ready for any conversation and new sexual experience.