A Beginner’s Guide To Anal Sex


I'll be real here–I get pleasure from a little pain. As a result of that, I can be a bit of a masochist in how I approach things of the sexual nature. I enjoy lovemaking, but rough sex has always been a personal preference.

Anal, or butt sex, kind of nestles on a line in between those two things. Where pain meets pleasure, pleasure meets pain. Anal sex isn't ordinarily a go-to for many couples, mainly because the nature of it is not the seamless penatration and frenzied motions we see porn stars encapsulate so well on film. That kind of pacing is something that has to be worked toward.

Yet, anal sex is increasingly becoming more and more of a facet in our day to day sexual experiences, whether it is an option you want to engage in during that time of the month, in lieu of period sex, or if you're just looking for something a little different than vaginal penetration or oral sex.

The anus is a very erogenous zone of the body and is very sensitive to touch, and thus offers a very pleasurable experience when stimulated. For women, anal sex can promote the stimulation of the g-spot, the clitoral legs, and the cervix due to those nerves being in close proximity to some of our bodies' most pleasurable areas. Some women who might struggle with obtaining an orgasm might find that anal provides a whole new set of sensations that lead to that illustrious vaginal orgasm (in tandem with other forms of stimulation, of course).

However, as previously mentioned, despite what you see play out on your favorite PornHub vid, entering an ass is not the same as entering a vagina.

While the vagina stretches to accommodate the penis naturally, the anus needs a lot more help to become pliable. I refer to the anus as a “ring of fire" because initially when your partner penetrates you, the hardest part is to get the head of his penis past that ring, and a lot of women get thrown off by that feeling of strong discomfort and pressure that they experience and stop altogether.

During my first couple of attempts at anal, I underestimated just how much help my ass needed to accommodate a penis, and even an average sized penis felt gargantuan knocking at that door, so I gave up on anal very easily. I didn't take into account the level of preparation you need before anal to make the ride as smooth as possible. And I mean that literally.

What To Do Before Anal Sex

Having a proper diet and good hygiene practices helps with overall cleanliness down there. I've heard some people go to the extremes of douching as a means to act as an enema, but I can honestly say that if you're eating a good diet, your body does its work enough throughout the day to keep the bowels clean. If you are planning to have anal sex, say “no" to eating at least a few hours prior to intercourse to avoid any unnecessary messiness. Strengthen your muscle control through Kegel exercises to further increase pleasure down there.

Also, consider investing in butt plugs. Some adult novelty stores sell them in a three per pack variety with the small, medium, and large options to train your anus. I had great success using them and gradually increasing in size throughout the week leading up to my first true anal sex experience. The small was about the size of the finger and of course, the large is at least the width of a penis, which made anal easier. Practice makes perfect. It's something you can invite your partner to do with you as well. I use them sometimes during vaginal sex, which makes for a new, more intense experience for the both of us as well.

Related: So Your Man's Not Feeling Your Sex Toys, Here's How to Change That

Foreplay is not a luxury; it's a necessity, and even more so one when partaking in anal. It's important that your partner makes you feel like you're in heaven on earth. He should be catering to your every whim and desire as he crosses deserts to bury his head in the water that is that valley in between your thighs. Also a sensual butt massage does wonders in opening up your body to the pleasure it is about to receive.

"Foreplay is not a luxury; it's a necessity."

During Anal Sex

Lubrication is undoubtedly THE most important part of anal sex. Again, the anus is not the vagina, so it needs a little help. In terms of lubrication, it needs a lot of help. My golden rule with lubrication and anal sex is that there is never too much. Spread it very generously on the penis, even if a condom is being used. Spread it very generously on your ass and anus, spread it very generously on your plug, and have a few practice strokes. There's no such thing as too much lube because the anus does not produce secretions like the vagina does when aroused, and those secretions are important to protect your body while producing the friction that sex creates.

Related: The Wetter, The Better: A Simple Guide to Getting Off With Lube

Relaxation is also incredibly important. Breathe and focus on the relaxation of the anal area opening for your partner. He must enter you as slowly as possible. Remember that ring of fire I mentioned above? My favorite way to be entered anally is in the spooning position, with his arm around me and his lips at the back of my neck. Focusing on his breathing and how delirious those kisses feel at the base of my neck (that's my spot!) help me to relax enough to let him into my body. Some women find distractions in the form of other stimulants work best for them. For example, using a vibrator or having his/her hands find your clit and play with it.

Communication is the last big thing that comes into play with anal sex. My partner knows to always start slow and to allow my ass to adjust to the size of him. He instinctively asks me, “You okay?" I moan my answer. “Can I go a little deeper?" "Can I go a little faster?" Those questions enter the room after how into it I am becomes more obvious. My hips are meeting his thrusts, my moans are echoing off our walls. In other words, hell yes, daddy. We both are on the same page when it comes to what feels good to us and that allows the experience to be all the more pleasurable.

Comfort, arousal, and pleasure should be three of your biggest priorities when engaging in anal sex. It takes time and patience to have anal. Anal sex can be quite an intense and satisfying experience for both parties involved, and is definitely something I think everyone should try at least once.

Featured image by Getty Images

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You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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