The Scared Girl’s Guide To Butt Sex


      One of the things I love most about writing gay erotica is the trust people automatically bestow upon me. They’ll share something about their sexuality, past or relationships they typically wouldn’t with other strangers. And for whatever reason, the conversation often finds its way to anal sex. “Does anyone actually enjoy anal?” I get this question a lot. Mostly from straight women in their thirties. Though I have passed along a few tips to a gay friend or two along the way. If you’re a woman, you probably don’t need me to explain why we’re all so terrified when it comes to anal sex. We’ve all had pretty much the same experiences. We all got here on the same bus. Or, maybe you’ve managed to keep that hatch sealed. Or, you’re a dude. It’s ok, you can hang out too.

      A lot of my female friends and acquaintances don’t actually know any gay men, personally. Sadly, for them, I’m the closet thing they’ve got to a gay man. I do my best, guys. But I can’t tell you how many times someone has confided that they “Just don’t get how gay men can do it!”, before they shudder on their behalf. If they’re Catholic, they might even cross themselves. “Um… Correctly?” is usually my response. I understand that they’re not shaming gay men for having anal sex. They’re pitying them. I tell them they’ve been doing it wrong.


      For most of us, our attitudes toward anal sex are formed from two experiences.

Experience #1:

      You’re twenty or twenty-one and you’ve had the night of your life at your sorority’s mixer. You literally drank your face off and Chad finally noticed you. His dick game is strong. He doesn’t lay on you like a stolen corpse and he took notes during the foreplay parts of his favorite porn clips. Maybe you smoked a joint and actually inhaled but you’re feeling DIRTY. You give him the good head, where your nose runs all over the place and your mascara slides down your cheeks as he punches your tonsils. He senses the mood is right and asks if you’re into “butt stuff”. Normally, you’d call his mom and tell her she raised a serial killer but not tonight. Tonight, you’re breaking your father’s heart. Tonight, you’re the girl of Chad’s dreams. Tomorrow, there’s going to be a 1:32 video on Pornhub titled “Tinder slut takes anal like a pro” and you kind of know about it and you’re not mad at it. Somehow, he slides in and it’s nowhere near as bad as you thought it would be. You thought it was going to hurt so bad you’d never want to poop again. But it’s good. This is when you’re possessed by a demon and you let him ride you around his dorm room like a pogo stick. The sex is amazing. You come so hard one of your fillings falls out and you swallow it.


Experience #2:

      You’re in your early thirties. Chad might have told his frat brothers about the night you let him stovepipe you. After that, you installed a security alarm on your emergency exit so you wouldn’t develop a reputation. You still think about that night when you masturbate but you’ve never felt comfortable or been drunk enough with any of the men you’ve dated to dip your toes back in that pond. Until tonight. Ted’s The One. Maybe he’s proposing tonight, I don’t know. But you’ve decided it’s time to rock his world and show him you’re the woman he can take home to mom but also the freak he’s going to tell his racquetball buddies about. He won’t though. He doesn’t brag about you when he’s with his homeboys. He talks about how some other woman’s nipples pushed through her shirt when she handed him his coffee. Anyways. You’re wearing heels and dress that only looks good on you if you keep your stomach sucked in and walk with your tits two feet in front of you. You’re having dinner at one of those nice restaurants where your server talks softly instead of throwing peanuts at you and line dancing on the table. You order the fettuccine alfredo because you forgot that you can’t really tolerate dairy anymore. Who cares? Tonight’s going to be special. Butter, cheese and heavy cream are no match for Romance. Two hours later, you’re back in your junior suite at The Radisson and you’ve had like six cosmos. You’re not feeling 100% but you’ve hinted that tonight’s going to be extra special and you can’t back out now. He brought luuuuube. You’re locked in so you have to make it work.


You’ve told Ted all about your wild night in college. He probably asks you to describe it in detail every time he’s coming around third and sprinting toward home plate. Ted knows what’s on the itinerary and he’s stepped up his game too. He plays Enya and puts on a diving cap and nose plugs then motorboats your clit while you hiss and cringe in agony. Then, it’s time. He settles over you after he’s slapped a palmful of KY on himself and you hold your breath. It’s not good. Actually, it’s about as bad as a thing can get without requiring an ambulance. It feels like you’re trying to sit on a hot road cone and you’re pretty sure you’re going to have to sneak the sheets out of the hotel. The engagement’s probably off.

       That’s pretty much the end of it. Anal is forever off the table and if Ted so much as mentions it again, you’re going to counseling. But it doesn’t have to be. If you’ve watched any porn on your own, you’ve seen plenty of women and men having an absolute blast as a rubber fist is jammed into their backside. Obviously, it works for some people. What are we doing wrong?


1. Stop treating your ass like it’s church. Visit more than twice a year and forget about dressing up. Your fifth anniversary is not the night to kick in the door and take hostages. Why are straight married people so set on making anal sex romantic? In our house, we have Wu-Tang Tuesdays. Not that we only have anal sex on Tuesdays. It’s just fun and easier to make that a standing appointment because I get a little more haphazard with my diet toward the weekend. But whenever we do it, we don’t listen to Bolero or John Legend. We listen to Wu-Tang, Jack White or something we wouldn’t let the kids listen to when they were toddlers. Listen to something with swear words, you’re going to say a lot of them.


2. Accept that you have a digestive track and respect it. Back when you were in college you lived on clear alcohols and Diet Pepsi and you definitely didn’t eat on Saturdays because you didn’t want to look “bloat-ie” in your low rise bootcut jeans. You didn’t give a fuck about fiber. You were like a field of fresh snow when you went for it with Chad. I usually cut out most dairy and meat at the beginning of the week and eat more vegetables and lentils and drink a kale-based green juice for breakfast a few times a week. I read a magazine article about a woman who let her boyfriend pressure her into spontaneous anal because she thought he was about to propose. Things got messy and he broke up with her. I’m not kidding. The first thing everyone has to agree to and accept is that butts aren’t just for fun, they’re functional. And if you’re going to do adult things to your butt, everyone involved should be adult enough to understand there might be consequences.

3. Avoid the consequences. This is where so many straight women sabotage themselves. They’d do well to pay a little more attention to porn or consult the internet for advice. Anal sex is infinitely more enjoyable when you’re squeaky clean. It takes about 75% of the worry out of it and lets you focus on more important things. Like remembering to wear waterproof mascara and holding onto your ankles. There are a range of cleaning options. You can keep it simple and straightforward and buy a Fleet enema or you can get a little more niche and play with hot water bottles and hoses. I fall somewhere in between and like adding the tiniest bit of rose or peppermint scented castile soap.


I also like to hedge my bets with an Immodium in the afternoon. Mind your electrolytes, though. I try to drink a few Powerades before and after cleansing because I hate fainting. Do your research first, or ask someone you trust for advice.

4. You should definitely go it alone, in the beginning. You probably knew your way around your vagina long before you let a boy or another girl touch it. Figure out your butt too. You’ll be more relaxed and less embarrassed if it’s just you. Also, he’ll think it’s sexy as fuck when you look like you know what you’re doing. Just casually strum your fingers over it while you’re masturbating and slowly add a finger or two back there to the routine. Be patient and keep it chill.

5. You ALWAYS use lube. And a lot of it. Unless you’ve ever wondered what it’s like to get a rug burn inside your ass or you just really like pain (which is fine, too), you should have plenty of an appropriate lubricant on hand. Look on Amazon and pay attention to what works with different toys and condoms, if you’re using them. I wouldn’t have anal sex without a lubricant with lidocaine in it, at least. Even if it’s just you, you’re going to want to get really slippery. I have four different types of lube in my toy drawer. I use a lot of coconut oil too.

6. S-T-R-E-T-C-H. You couldn’t feel your face or those vicious little muscles in your ass when you let Chad ride you to town and back. I will admit: I cheat. Nothing gets me in the mood for butt sex like pot. And pot makes butt sex a hell of a lot easier. Poppers are fun too but if you’re actually reading this for advice, you might want to hold off on those. Also, I keep a prescription strength bottle of viscous lidocaine in my toy drawer. I do not know the long-term side effects or dangers of using lidocaine rectally and advise you to proceed with caution. You could also ask your doctor if you’re fine with him judging you. I like to live dangerously so I go heavy on the lidocaine about fifteen minutes prior, after I’m so fresh and so clean, clean. But if you’re embarking on some light anal play or everyday anal sex, you’ll probably be fine without a prescription. Now, here’s what your gay friends would tell you, if you were brave enough to ask them: Stretching makes a huge difference. Spontaneous anal sex happens all the time and it’s really hot. It’s just not for us. Yet. Taking a little time to ease into it can take most of the pain out of anal. Unless you want it. You can just skip ahead, then. I pregame by gradually using a variety of different sized vibrators or dump them on the bed and we use them during foreplay. It’s a lot of fun and you won’t scream like you’re being murdered as he’s fighting his way in.


And you don’t have to worry about breaking or wearing out your butt. For the most part, the ass is a lot like a vagina and will stretch and shrink back to normal shape after a few hours. Forget what your friends told you in high school, your lunch isn’t going to fall out. You can find some really impressive pictures of prolapsed anuses on the internet but a lot of time and diligence went into them. That rose didn’t bloom overnight. Not that you won’t want to be a little mindful, the day after. But you’ll be fine. I promise.

7. Try ALL the positions and get comfortable. There’s a sweet spot in there and you might have to pull a few muscles before you find it. But it’s super worth it. You don’t have to hug your knees and pray that it’s over quickly, watch a few videos or look on Pinterest for a Kama Sutra For Moms chart or something. The ideal positions would be ones you can really settle into and work. You’re not going to look hot while riding him reverse cowboy, if you’re doing it right. Just commit to sweating and swearing and whatever else works.


8. Anal sex can happen at any time. Seriously. Stop saving it for birthdays and anniversaries. Many people have anal sex daily. They don’t need a special occasion, they just do it because it feels really good. But it takes a little practice and twice a year isn’t really cutting it, is it? And do you really want to make something you’re probably going to be awful at the focal point of your tenth anniversary?


The Scared Girl’s Guide To Butt Sex