Loving Anal
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Loving Anal
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The first time a boyfriend asked me to try anal sex was in high school. I was 17. And because I loved him — in the way you can only when love when everything is fantastical and a first — I agreed to try it. We dated for three years, and basically introduced each other to every type of sex there could be: I even gave him a Kama Sutra book for Valentine’s Day one year, not realizing that experimenting with so much inexperience would never be quite as hot as my coveted Cosmopolitan magazines promised it would be.
Even so, after reading about what to do, we gave it a try. But as soon as he barely entered me, I asked him to stop and apologized, telling him that I just couldn’t do it. It was too scary. Too much. It hurt.
Fast forward to a few months after I turn 22 and I’m desperately in love with a "mature 29-year-old" man that we’ll call Scott*. After years of lackluster, jack-rabbit sex, I’m amazed at what this older dude can do with his tongue, with his hands, and with his body. He isn’t the most well-endowed man I’d ever known, but he is the first to ever give me a stellar orgasm and to really, as the romance novels put it, worship my body.
We’ve been dating for a while, and after a quickie in the morning , he casually asks if I’d ever be up for trying anal sex . I go into the story about my ex-boyfriend from when I was younger and he rolls his eyes, kisses my cheeks and says, “But I know what I’m doing. It’ll be good for you, I promise.” I tell him I’ll think about it, but secretly, I just want to do more research (my journalist brain never stops investigating!) to figure out if anal sex is ever good for women .
The very idea of someone entering into your backside seems a little gross — right? You’re only supposed to dispose of (gross) things back there, not put something inside that’ll be painful as it moves deeper. I couldn’t understand — for the life of me — why in the world anal sex would make me as turned on as I am in doggy style ?
The first time we went for it, he started by going down on me. It was as good as it always was and right when I thought I couldn’t take it, we started having "normal" sex. It was slow and sensual and he made sure to focus on kissing my neck and ears, getting me more and more turned on. He then flipped me over and we had really hard doggy style for a while, and without lube or anything, he easily slipped inside my backend.
Like before, it was painful, but he told me to breathe as slowly eased all the way in. He then reached around and started to play with me with his fingers as he gradually moved faster. I got more comfortable as he went on, and almost forgot where he was. As I let go more, the tension faded. It didn’t hurt as much. And without even thinking about it, I had one of those explosive orgasms that you feel all the way up to your face.
For the duration of our year-and-a-half relationship, we worked in anal sex at least once a week. We got into such a steamy rhythm that we eventually tried different anal sex positions — including missionary and spooning. It easily became one of my favorite ways to have sex, and though the clean-up was pretty messy every time, I loved how the orgasms varied and how much fun we had with it.
Nowadays, the "anal sex conversation" is one I bring up with guys I’m dating. Once we make it exclusive, I casually bring up the topic of things to try in bed, just like my previous ex-boyfriends had done. Most of the time, like 9.5 out of 10, men are pleasantly surprised with my appetite for non-traditional intercourse. It isn’t always good, and to be fair, sometimes a guy is simply way too big for it to feel good. But sometimes, I get lucky (and ahem, he does too) and I find that happy place with anal sex again.
It might seem invasive to some — and yeah, a little dirty — to have anal sex as part of your bedroom adventures, but I think it's always worth a shot. And frankly, a few shots. Just like when you lose your virginity, losing your anal sex virginity isn’t exactly pleasurable. But with the right person, the right patience, and the right movement, you might just find yourself persuaded to the other side.
My biggest recommendation? Though my first anal sex experience was sans lube and it was fine, lube will be your best friend. And a nice, warm shower before you get it on.
Want more of Bustle's Sex and Relationships coverage? Check out our video on sex positions for small penises:
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Despite there being a healthy renaissance for butt play in recent years, backdoor entry is still a deal-breaker for many women — a no-way, no-how, entirely off-limits scenario. Still, more than a third of women (36.3 percent) surveyed in a 2015 study from the Journal of Sexual Medicine reported having tried anal sex ; 13.2 percent reported having had it within the past 12 months.
For some women, like me, anal sex can be a mind-blowing addition to the bedroom . Until recently, I’d never had an orgasm from anal sex alone. Anal sex has always been a welcome precursor to vaginal penetration and other below-the-belt play. The most intense orgasms I’ve had — ever — have involved some combo of simultaneous vaginal penetration, clit stimulation, and ass play.
The key, for me, is to have a patient partner — one whom I trust. Oh, and plenty of lube. The anus isn’t self-lubricating, and the sphincter needs to be relaxed before you insert anything into it. For me to engage in anal sex, I need to be fully relaxed, lubed, and ready. And even then, sometimes the equipment isn’t, umm, compatible. Usually, I’d say you can never have too much of a good thing, but size can be an issue.
Anne Hodder, ACS, a multi-certified sex and relationships educator, says a successful anal experience is most often the result of communication, relaxation, preparation, lubrication, and (at least initially) gentle stimulation. “Anal is something you and your partner should discuss and plan for while sober and clothed,” she says. “Discuss expectations and concerns.”
Here are my top 25 tips on how to enjoy anal sex :
It needs to be a “hell yes.” Like anything in life, if the idea of anal sex doesn’t inspire an enthusiastic “hell yes” you probably shouldn’t do it. If someone has to convince you to do something, say no.
There needs to be a solid level of trust. For me, anal sex requires a higher level of trust than vaginal sex. I’ve rarely had painful vaginal penetration, but there have been a few less-than-memorable mishaps with an overzealous penis and my ass. I’m not letting a penis or strap-on get near my backside unless I trust that you’ll wield it responsibly.
If you “accidentally” slip it in, you’re an asshole. There are these concepts called consent and communication. Accidental anal is not OK.
Let go of any expectations. Instead of immediately focusing on full penetration, try to be as present as possible, and enjoy the buildup and arousal. Sometimes, it takes a few tries to make it happen. And sometimes, anatomy doesn’t fit, or it’s painful for the receiving partner.
Your butt is beautiful. If you’re going to let someone stick their dick or strap-on in your backside, you’re going to have to relax about how it looks. It may not be your most favorite body part, but the reality is that someone will be looking at it, they may be licking it, and if all goes as planned, penetrating it. All butts are beautiful.
Relax. I know, I know — this is easier said than done. If you’re nervous, take a few deep breaths. Like you mean it deep breaths. A calm mind will hopefully set your ass at ease.
Slow and low is the tempo. I cannot emphasize this enough. Go as slow as you need. And if something doesn’t feel quite right, it’s OK to stop and start again. I’ve learned things go more smoothly the slower I go because I’m not triggered to clench or clamp down from worry or discomfort.
Start small. Instead of going for the biggest dildo in your bedside arsenal, start with something small, like a single (lubed) finger, and work your way up.
This bullet vibrator’s small and compact shape makes it a great toy to use as you start out.
Communication is key. Your partner may be fan-freaking-tastic, but they are by no means a mind reader. It helps to have a conversation before you have butt sex for the first time. And if you’re in the throes of it, if you want more or less of something, use your words and speak up.
Use silicone lube (and don’t skimp). The anus is much tighter than the vagina, and it doesn’t naturally self-lubricate like the vagina does — no matter how turned on you are. Thick, silicone lubes tend to be longer-lasting and make for a smoother sailing backdoor situation. The wetter, the better. Always.
Unless you’re using silicone toys… This is a pretty simple rule of thumb: If you’re using silicone toys, use a water-based lube, since silicone-based lubes can break down toys and make them gummy and gross (like material doesn’t like like material).
And definitely, don’t use a numbing lube. Desensitizing lubes aren’t inherently harmful, but the anus consists of thin, sensitive tissues, so tears and irritation are more prevalent. I want my body to be able to signal if something isn’t right.
Go shallow at first. Whether it’s with a toy or finger, go shallow at first when penetrating someone’s anus. I know, the impulse is to get in there — all the way in there — but take it easy, tiger, before you deep dive.
The position can make all the difference. Many positions are anal sex-friendly, and some are better than others. Doggy style, spooning, and the standard missionary position are best.
Don’t make any sudden movements. Sometimes it’s nice to add an element of surprise to your sex life, but not when you’re being penetrated anally. It’s not only painful; someone could legit get hurt.
Invest in a quality butt plug. If you’re brand new to anal play, I strongly suggest playing with a butt plug prior penetrative anal sex with a penis or strap-on dildo. (You can do this by yourself or with a partner.) It will get you used to the sensation of being “filled,” as well as help relax the sphincter.
Avoid ass to mouth play (ATM). If you’re a vulva owner, the potential transfer of bacteria from the anus to the vagina should be a concern. If you are moving from anus to vagina, switch condoms, or be sure to clean your penis or strap-on thoroughly.
Don’t overlook analingus. Before you yuck this popular yum, please know that a lot of people find having their anus licked to be a very pleasurable experience. The anus is full of all sorts of ultra-sensitive nerve endings, especially around the entry, that can get the blood flowing to all the right places.
The prostate is a magical source of pleasure. For the penetrating penis, the anus is very tight, which can feel amazing. There’s a lot of pleasure on the receiving end too, thanks to the prostate. Here’s how to find it, stimulate it, and make it super happy.
Steer clear of comparisons. Anal sex enthusiasts shouldn’t compare themselves to the porn they watch. “Keep in mind, when we make porn, we need to show actual penetration, which means we have to open up for the camera and get fucked with big things. This doesn’t always feel great,” says Lance Hart . Brooklyn Chase adds, “In porn, prep for an anal scene includes a lengthy and unpleasant routine of enemas, very little food, and anti-diarrhea medicines.”
It may be a messy event. If there’s stool in your rectum, there may be some leakage. If you’re worried, you can try to empty the pipes before sex or give yourself an enema. Seriously though, you’re sticking stuff in the superpoop highway, and stray turds are a risk you take. It’s really NBD.
A washable throw is your friend. I hate doing laundry, so if I’m going to have potentially messy sex, I pull out my washable, waterproof throw . It works perfectly on top of sheets, sofas, or any other sex-friendly surface, and can easily be thrown in the washer.
It’s OK to hit stop or pause at any point. Consent can be revoked or renegotiated at any time. A lot of people don’t understand that you can be in the middle of an act with somebody — like anal sex — and can put a full-stop on it, at any time, even if you’ve said, “Yes, I want to do this.”
If at first you don’t love anal, give it a second chance. I had some awful anal sex experiences early in my sexual career. For a while, it was off my between-the-sheets menu, and I’m damn glad I gave it a second chance. Not all penises, strap-ons, and partners are created equal, and it took me some time to find the perfect fit. I’m all for sexual agency, but sometimes, some things are worth a second glance.
A version of this story was published June 2019.
Looking for even more adventurous sex positions. Check out our bucket list for 69 (nice) options:
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