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A Gentleman’s Guide to Butt Stuff

A Gentleman’s Guide to Butt Stuff:

Butt stuff really hit its stride in 2013-14 musically (Nikki Minaj’s “Anaconda”), academically (Harvard’s butt play workshop) and intellectually (Amanda Hess wrote about it for us) before reaching its cultural apex with the now infamous rear-motorboat scene in Girls.

Despite all the hubbub, I’ve found that ass play is still a topic cloaked in mystery, shrouded in shame and often stigmatized among many people I talk to. The whole thing is too broad to cover in one piece, so I broke it down by gender. This special piece of ass is all about her.


I’ve been an Anal Advocate for more than a decade. It’s absolutely not for everyone, but personally I LOVE all things ass. It started with a man who was obsessed with my butt in the best, most respectful possible way: he worshipped it. This particular man daintily ate my ass like a young fawn nibbling grass on a dewy morning. I could feel every sensitive little neuron responding to his tongue; it was absolutely delightful. We graduated to “The Shocker,” which quickly became my favorite sex act and the fastest way to make me come in under 60 seconds. It was only a matter of time before I wanted the full enchilada.

Anal is one of the few sexual positions where I truly have to submit and relinquish control. What turns me on is actually less about being dominated and more about trust. I can only relax if I trust you, and trusting someone in our current national Tinder hellscape is priceless. Therefore, anal sex is special to me, and so I save it only for those special men in my life. For me, anal is associated with feelings of devotion and true, deep relaxation, the kind you have to breathe into. Well, that and THE ORGASMS ARE FUCKING EPIC.

Whereas vaginal orgasms feel like they originate externally at the clit and move inward, anal sex orgasms start from the inside out. They feel like they begin from your G-spot and explode out like the Big Bang. They’re white-hot and rolling. “Don’t knock it ‘til you orgasm from it,” I tell my girlfriends when they are panicked because their boyfriend/husband casually mentioned anal over smoothies. What I’ve learned is that most women had one horrible experience that tainted their perception of ass play forever. These are the most common grievances so you can either avoid them and/or address them.


DON’T DIMINISH THE INTIMACY
Once reserved for special occasions, birthdays and holidays, thanks to porn men now expect anal because it’s Tuesday. I’m not alone in the idea that ass play (anal sex in particular) is something sacred I don’t share with any old fuck boy. Friend and comic Courtney Banks said, “I’m saving it for marriage because I’ve had a lot of sex, and I want to have something special that I can give to my husband. If we walk down the street and run into someone I fucked I want my husband to be like, ‘But only I had that ass.’” It might not be a big deal to you, but it’s usually a big deal to us. The sooner you respect that, the better.

THERE WAS NEVER A DISCUSSION
You did not “accidentally” slip your dick in our butthole. Literally every woman I spoke with (myself included) has a story about a dude suddenly trying to jam his cock in through the out door. THIS IS NOT OK AND THE NO. 1 REASON MOST WOMEN WON’T GO NEAR ANAL. It’s disrespectful. It’s nonconsensual. It’s painful. Ass play deserves discussion. I realize bringing it up can be tricky. Watching porn together can be a good way to break the ice. In the bedroom, start slow with fingers and ask questions like, “Do you like that?” Gently tickle her anus and ask “Can I lick your beautiful little asshole, baby?” If you really have no idea how to bring it up–instead of “accidentally” slipping into her butt, I recommend you “accidentally” leave this column open where she can see it.

GO SLOW & LUBE UP
I CANNOT EMPHASIZE THIS ENOUGH. My friend Jonnae Thompson said, “The difference between an anal plug and a dick, size-wise, is like the difference between a baby carrot and a cucumber. You’ve got to ease into it.” Start with ass play and fingers. Work up to butt plugs and toys. Part of the fun is graduating to different levels with your partner and exploring boundaries together. And when/if you do get to anal sex, by ease into it I mean millimeter by millimeter. Let her relax. Remind her to breathe. Keep lubing up. The ass doesn’t produce lubricant, so get some water-based lube and apply generously. If it’s not working, NEVER FORCE IT. Kiss her, laugh it off and tell her it’s no big deal; you can try again another time when she’s ready, if she wants.

RISK/PREVENTION
As with any sex act, there are risks. Dr. Susan Philip, director of disease prevention and control for the San Francisco Department of Public Health told me:

“Anal sex, or ass play, carries the risk of all common STDs such as chlamydia, herpes, gonorrhea and syphilis, as well as HIV. For this reason, condoms are always recommended. Oral play also includes the risk of bacterial diseases such as shigella and E. coli. In general, people should wash well. (Anal) douching is not recommended. A dental dam, Saran Wrap or any barrier can be helpful to minimize the risk of transmission.”

I also reached out to Dr. Rega Pen, a sex therapist and family and relationship counselor who has written about the risks of rimming, among other things, and she said, “Each time I write something about the wisdom of using barriers during rimming I get letters from folks protesting that they’ve been doing it ‘bare’ for years with no ill effects. I still hold that if you don’t know–repeat, know–the HIV and hepatitis status of your partner, either use a barrier or use lube and the flat tip of your finger, which feels virtually the same as the tip of your tongue. If you are with a regular partner, get vaccinated for Hep A and B, wash your bottoms thoroughly beforehand to avoid a possible tummy ache from E. coli and enjoy this hot and very intimate exchange.”

Nothing turns me on more than when a man takes responsibility for his health and mine. Arm yourself with knowledge so you and your partner can have peace of mind.

DON’T DOUBLE DIP
Save the butt for last. Once a finger or any body part or toy goes in the butt, it’s out of the game. Benched until sanitized. This is how women get infections. Infections mean no sex. No sex is no fun.

IT’S NOT ABOUT POWER
The porn-on-demand generation is coming of age, and I’ve spoken with younger women who have felt an enormous amount of pressure to “do anal” before they felt comfortable. This just isn’t fucking cool, guys. I realize the challenge makes you lust for it even more, but dial the sense of entitlement down a notch. Mariya Alexander, a good friend, podcaster and comedian, said, “I’ve encountered dudes who are obsessed with making women take it in the ass, and that is pathological and scary, and I would never let someone near me if they exhibited any signs of being butthole-obsessed.” It should always be about pleasing her. Never about subverting her will.


Just because I love anal does not make me an expert, so I talked to sexpert and adult performer Sovereign Syre and asked her the most common questions about ass play that I received from men about women.

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Why is the butt the most stigmatized part of the body?
Shit is the final taboo. People find shit part of the turn-on, or the potential for it. Anal is about being subversive, dirty. That’s part of its appeal.

How do you bring it up?
Bring it up when you’re not in the bedroom. You don’t want the instant pressure of ‘Let’s go!’ Tell her how sexy her asshole is, how turned you are at the idea of playing with her asshole. You have to sexualize the most stigmatized part of her body.

What are the best toys?
When you’re comfortable getting your fingers inside her, it’s time to move to toys. I’m saying this with the idea that the intention is to have anal sex. You can find dilator kits online or at any sex shop. They are butt plugs, usually four or five, each getting bigger than the next, like those Russian nesting dolls. Just like you did with your fingers, use lube and take your time inserting the butt plugs. It won’t all happen in one day, but you slowly get her (or your) body used to accommodating more and more. I like to use the biggest plug I can fit and then use a Hitachi (Magic Wand) to masturbate so that my body associates penetration with feeling really good. 

What are the best positions?
Everyone is different, and there is no ‘best’ position. Seeing what feels good to her, what makes her body relax, focusing on the different sensations and how they make her feel, you’ll learn a lot about her relationship to pleasure. Does she have trouble relaxing? You’ll discover a lot about what makes her feel good and bad. And you know what? If you can’t make it feel good, then ass play isn’t for her, and that’s fine. Sex is about fun and discovery. Also suggest maybe she try it alone, away from you. Give her room to explore away from the prying eyes and expectations of you, her lover. 

What preoccupies women with it?
Most women ask me how I keep from making a mess. Most men ask me how to keep it from being painful for the girl. Funny, right? Most girls are worried it will hurt or that they’ll shit on the guy’s dick. Pain usually comes from not enough foreplay, stretching and desire. I cannot stress this enough. The only reason to try anal is because she WANTS to, not because she thinks she needs to because she needs to keep you or keep you from getting bored. This is her body, and it’s about her pleasure. 

Is there a turning point from when you don’t like it to liking it? What about it makes it pleasurable?
I got curious about anal because after you’ve had sex a few hundred times with your boyfriend you wonder if there are other things you could be doing to feel good. I hated feeling like there was something that I couldn’t do. I had a lot of friends that really loved anal sex, and I wanted access to as much pleasure as the next person. For everyone it’s personal. For me what makes it pleasurable is that it’s dirty, and the sensation of it is intense. You can’t be anywhere else. Anal sex keeps you very present. 


Next week: we get into men’s butts.


Bridget Phetasy is a writer and comic in Los Angeles. Twitter: @BridgetPhetasy.

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