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This Holiday Season, Give the Gift of Anal

Playboy is here to make sure you get at least one thing off your wish list

Pinto Horse

Here’s an occupational hazard I’m sure 99 percent of the population doesn’t run into: When you write about sex and relationships for the internet, like I do, and you’re a single woman who goes on a lot of dates, like I am, people tend to think that you have a lot more experience than you do when it comes to sex. Though I’m sex-knowledgeable and accepting of everything (so long as it’s happening between two consenting adults), I’m pretty vanilla in my own sex life. And yet, people are constantly asking me about polyamory, sex parties, the best kind of edible lube, and rim jobs on a regular basis. My cocktail banter rocks.

Partners also tend to assume I’ve experimented more than they have. Which is why, just a few weeks ago, my most recent partner found himself more than a little confused when I admitted to him that I had never had anal sex before. “Really?” he asked, naked and befuddled. “Never?” I repeated that I hadn’t—and that, in fact, I was still a little hazy on how to handle anal as a first-timer.

I’m not the only heterosexual female to be confused about the mysteries of P-in-A sex. An unscientific poll of my female friends who have sex with men uncovered a startling amount of head-scratching. So even though my partner and I went our separate ways before attempting anal, and my butt cherry is still intact, I decided to talk to a professional about everything you need to know before having a dick up your ass for the first time. Bella LaVey is a former dominatrix and erotic wrestler turned holistic sex coach, and author of the upcoming book Fetish Girl: A Memoir of Sex, Domination, and Motherhood. She walked me through everything us gals need to know about our first time having butt sex. Hint: There’s lot of lube involved.

The first thing you have to do when a partner mentions anal is to figure out how you feel about it. “Just because someone wants it, doesn’t mean you have to give it to them,” LaVey says. This is especially true if you’re dealing with a new partner. “Anal sex requires you to surrender and open up in a way that’s very profound,” she says. “You need a partner to recognize that.” For that reason, LaVey cautions against having sex with a casual partner—for more reasons than the emotionality. (More on that in a second.) “Everyone is free to make their own decisions,” she says. “But if it’s your first time, you want there to be open communication.”

That leads us to our next point of prep work: Talk! Don’t just jump into anal willy-nilly. “It’s important to know each other’s experiences with anal sex,” LaVey says. “If you’ve had a situation in which a partner poked in the wrong direction, and it was painful for you, then you might have some unresolved trauma that’s making you afraid.” Being open and communicative is so important ahead of any sex act, but that’s especially true if you’re new to anal, she says.

If you’ve never had anything in your ass, LaVey says it’s a good idea to experiment on your own. This can actually be super fun to do. “In the bath, play with your ass a little,” she says. “Don’t let his cock be the first thing that goes in there.” She suggests sticking a finger in first and seeing how it feels. You and your partner can and should also play around with fingers in bed. Butt plugs are also a fun toy to use during P-and-V sex, and LaVey says not to discount rimming. “It can get you used to having someone in that area,” she says. “Plus, it feels yummy.”

Remember: The vagina stretches. The anus? Not so much. So if you’ve done all of this and anal sex is still painful, then it could just be that your partner is a little too big.

The Main Event
Let’s get the most pressing concern out of the way first: If you’re worried about shitting on your partner, there are a few things you can do. First of all, LaVey reminds, the rectum doesn’t hold poop. Waste only passes through there, so the chances of your partner getting a ton of doodoo on them is pretty slim. But if you’re worried, she suggests eating a light meal before you know you’re set to have anal for the first time. You can also pick up an enema from the drugstore and do one before. “It helps me to feel light and clean,” LaVey says.

Foreplay is super important when it comes to anal sex, especially since most women won’t have an orgasm through anal alone. It’s a good idea to build up arousal in both parties, which can make relaxation a whole lot easier for the woman taking the dick. “It’s not a bad idea for her to have an orgasm before anal sex, or even have a little vaginal sex before,” LaVey says. Just remember the golden rule: Unless you’re washing up or changing a condom, never go from anal to vaginal sex. Vaginal to anal, however, is fine.

As far as lube goes, “you can’t use too much,” LaVey says. She says putting some inside of your anus as well as on his cock can help everything slip and slide much better. “Water-based lubes tend to dry up quickly, which is why I’m a fan of oil-based lubes,” LaVey says. “You want it to be slippery, not sticky.” She likes brands like Uberube and Yes. But remember—oil-based lubes and condoms don’t mix, which is another reason LaVey says you should only have anal with a fluid-bonded partner. If you’re worried about relaxation, she’s also a fan of CBD oil lubes, like Awaken by Foria Wellness. “It can help the muscles around your anus relax a bit,” she says.

A rookie mistake when it comes to having anal sex? Going straight to doggy style. “This is the worst position to start in, because it shortens the rectum,” LaVey says. Instead, she says to try something that will stretch you out, making it more comfortable to receive your partner’s dick. “Try laying on your back with your knees pulled up to your chest, or laying on your side in a spooning position,” LaVey says. “Those are the best positions to relax your anus.”
And remember: The vagina stretches. (We pass babies through there, remember.) The anus? Not so much. So if you’ve done all of this and anal sex is still painful, then it could just be that your partner is a little too big for you to take. Don’t try to force, LaVey says, and be open with him about it. Chances are, he’ll revel in the fact that his size is a hindrance and stick to vaginal sex. (Men. Such simple creatures.)

Once it’s all over, make sure you communicate with your partner about how you feel. “You might have some new emotions bubble up that you weren’t expecting, which is why it’s important to do this with someone you trust,” LaVey says. Be honest about those feelings, and if they’re negative, don’t push them down just to make your partner happy. Sex is meant to be enjoyable for everyone involved, and it’s not cool for yourself or your partner if you’re doing something that doesn’t feel good. And if you loved it? Let your partner know that, too! “Anal sex is such a gift to give to a partner,” LaVey says. “It’s such a deep opening, and it can create even more intimacy between you and a partner.”

You hear that, ladies? Your ass is a gift! But we already knew that, didn’t we?


Maria Del Russo
Maria Del Russo
Writer, contributor
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