Anal Sex

Anal sex? A total beginners guide for your first time

If you think you're weird for fantasizing about anal sex, think again. Anal is far more common than you've been led to believe. Melissa A. Habel of the CDC released medically reviewed data in 2018 showing that one-third of all straight people between the ages of 15-44 had engaged in anal sex. That means that when three straight folks hang out together, chances are at least one of them has enjoyed anal intercourse before.

As common as it is, anal is only becoming more popular. Another medically reviewed study (also from 2018), showed that anal sex rates are at an all-time high: according to Courtney Maierhofer and others, U.S. Americans are more likely to have anal sex than a Twitter account. Talk about a mainstream sexual activity.

Even if you've never tried anal play before, chances are you're more than at least a little bit curious about anal sex. Maybe you’re a newbie to the magic of butts, or you’re just now broadening your horizons past the plug. No matter where you’re at in your booty journey, there’s no better way to become an anal master than by doing your homework – both in the bedroom and out. If you’re curious about how to take anal from “not now” to “wow,” there may be no Anal for Beginners course you can enroll in, but with a little light reading (and practice), you'll be well on your way to sensational backdoor lovin' in no time.

What does anal sex feel like?

I'm not breaking any headlines to say that anal sex is a nice sensation, but for people who've never had the pleasure of exploring their backsides, it may be confusing to tease out the appeal that men, women, and nonbinary folks alike get from anal sex. No matter who you are, anal feels good because of the pressure and fullness that comes from penetration. But that full feeling is only part of the thrill; the rest comes from the two main flavors of anal Big O.

Anal orgasms

Anal orgasms can be enjoyed by all genders and all expressions of beauty, and you can achieve this little death thanks to the ample nerve endings surrounding the opening of the anus. When stimulated by repeated stroking (and lots of lube), the quivering of these nerves can put some folks over the edge into pure bliss.

If you have a clitoris, try also stimulating it simultaneously for a blended orgasm of pure pleasure. Since the clitoris is actually a large internal organ, you can actually even stimulate the inner parts of the clitoris through anal as well (especially in positions like doggie style) giving you deep, internal orgasms.

Prostate orgasms

A sensation like no other, the prostate orgasm is one that only people with penises can experience. During anal sex (or really, any kind of anal penetration), the prostate is stimulated. A little walnut-shaped gland, this is also known as the P-Spot, and is the featuring star of basically all sex articles in giants like Men's Health for a reason.: folks who've experienced both say the prostate orgasm feels like a penile one, only way more intense and rippling throughout your entire body.

Prepping yourself for anal

If you've been watching porn or fantasizing about anal for a while, you may think you're ready to enjoy full-on anal penetration right out the gate, but pump the brakes. Anal sex takes work, and your first time will only be successful once you've read up on anal sex tips, and slowly incorporated butt play into your sex life.

The best way to begin?

Start with anal training

Anal what? 

Anal training is a fundamental piece of your journey into anal sex. Medically reviewed sex literature, as well as quality sex shops, all say you can't just go ahead and stick something with a lot of girth inside you and expect it to go well. This is your first foray into the world of butt stuff (rights reserved), and like a marathon, anal sex is something you need to train for, building up to with a sex toy or finger before gearing up for full-on anal intercourse with a dildo or penis.

As much as you want to go to town tonight, you’ll need a little prep. If you jump the gun and dive straight into anal sex, you’re in for a painful surprise. Understanding why starts with familiarizing yourself with your body. Remember, the anus isn't as fluid as the vagina. It's actually a group of muscles (called the anal sphincter), and just like how most of us can't put our legs behind our heads without loads of practice, you also can't expect the anus to take a penis or dildo comfortably right off the bat. Your muscles around the anus need to work up to it with gradual anal penetration.

To start building up to anal sex, a well-lubed finger is a great springboard. Once that level of stimulation feels comfortable, go ahead and insert two. Once you or your partner eagerly take all those fingers, you're then ready to use an anal training kit to help you stretch the anus and invite deeper, bigger penetration. Every anal sex training kit is different, but they typically offer three graduated plugs that build up in girth and also length.

For best results, start with a toy that’s only an inch in diameter. Move it in and out (with plenty of lube). After playing with it several times over the course of a week or a month, you may feel ready to move up to the next size. Keep sizing up until you’re confidently savoring the big one.

Although anal training may not sound like the most fun way to start, you’ll be surprised by the sizzling pleasure you get from even the smallest toy – and by starting small, you’ll be ready for the big kahuna in no time.

Use lube – lots and lots of it

If you think you use enough lube in your daily sex life, get ready to double up before you head through that back door. For starters, the muscles there are tight. Going too fast and not primed can damage you or your partner. And since an anus (obviously) doesn’t self-lubricate, you need to make sure both parties are nice and moisturized to keep things slick and smooth.

If you’re using condoms, you have to opt for condom-safe lube, like silicone or water-based varieties. A great brand is Good Clean Love, which offers chemical-free and condom-friendly lubes. These lubes feel great and add the pleasure of slickness and fun to your play.

Even if you aren’t using a condom and are playing with a monogamous partner, lube is a must for anal play. It keeps you from tearing, bleeding, or feeling pain, and makes you and your partner able to go all night long. 

If anyone tells you there’s such a thing as too much lube, they’re straight up wrong. Get slippery my friends, and have the ride of a lifetime.

Have the talk

Everyone wants to avoid the STI talk in a casual setting, but it's something your health can't afford to sleep on. Knowing your partners' statuses is well within your rights. Reserved people may feel too shy to talk about it, especially women who aren't taught to speak up about sex, but the single best way to help prevent the spread of HIV and STIs is to talk about it. Start by only trying anal sex with a receptive partner who is interested in talking about sexual health as well. Even if your sexual connection with someone is casual, you need to talk candidly about safety during anal sex.

HIV ravaged the LGBTQ community in the twentieth century, and now continues to spread through straight and queer spheres alike, mostly because of the lack of medically reviewed information out there on safer sex practices. When you're having sex (anal especially), learning as much as you can about your body helps you outweigh the risks, and may be pivotal to maintaining your sexual health.

Whether you have a PhD in sexual health or are just starting your sex education, you should always read the latest (medically reviewed) literature written on anal sex, sexual activity, and how to take care of your bodies. Failing to talk about safety surrounding anal sex has serious consequences. If you have hesitations in talking about safety, look inward. People socialized as women are taught to shy away from all things sexual autonomy, so any conversations about anal sex are immediately pushed to the wayside, and medically reviewed safe anal sex practices are embarrassing or shameful.

Men aren't off the hook and without risk, either. Medical experts all agree: condoms are a must. Anal sex and everything related is a delectable addition to your bedroom fare, but it's not without risks. If you're a man having sex with other men, you have to really make sure you're comfortable vocalizing the need for safety, regular testing, and the disclosure of any status your partner needs to know. The good news is that you can significantly reduce your risk of STIs or HIV if you talk about medically reviewed safe anal sex practices, provide your own condoms, and regularly get tested each time you have a new partner. Lead the charge with your lovers, male, female, and nonbinary, and open the doors to talking about safer anal sex.

If you have a penis, talk about the ending before it starts

There's one more awkward thing to bring up, besides safe sex: what you'll do when you come. Most sexual activity with a penis ends with semen, and just as with vaginal and oral sex, you need to ask your lover where they want it all to go.

As great as it is, for many people anal sex can also lead to more of a mess than they were expecting - so agree on where to come beforehand. Have a towel or tissue box handy to use during clean up after orgasming on your partner's back or belly, or ask if you can release it all inside them.

This uncomfortable conversation will help you both end on a sweet note that'll leave you eager for more.

Ways to make anal sex amazing

Now that you've built up to anal intercourse through anal training and frank discussions with your lovers, you're ready to go for the gold. As you and your partner gear up to the big event, set the stage. If you're not in a romantic atmosphere that builds that sexual tension, women and men alike will be tightening that anus, too tense to surrender to the sensations.

To help you and your partner relax, use good lighting, clean sheets, and a beautiful setup. Fundamental every time you have sex, the right ambiance will help you both be more receptive to anal sex. Remember: mood really is everything. You don't want your head rocking against the headboard while you stare at a clutter of dirty cups. That's not exactly going to relax the muscles around your anus and put yourself in the zone. Just ask all the women who slept with bros in dingy houses during their college years. Nothing makes you search in vain for an orgasm quite like a disorganized room that kills any romancin'.

So clear the clutter and dim the lights. Once you're ready, take control with a few more steps to make the night run as smoothly as possible.

Foreplay, foreplay, foreplay

Ever made a move to hit home base before trying to prime the pump? You probably found that reaching between your partner's legs only revealed a flaccid member or a vagina that's dry as a bone. Not exactly the best way to head into sex. Diving into the world of anal sex is no different. If anything, anal sex calls for even more prep. Most of the time, that means an anal sex quickie might be off the table.

Even if you’ve gotten plenty of anal practice in already, it’s still normal to feel a bit nervous before going all the way. If you’re not totally relaxed, you can have a hard time fitting a dildo or penis inside. Nervousness makes your muscles tight – a nonstarter for playtime. A great way to get relaxed in the moment is by building up your pleasure well beforehand. If your partner is going to be the one getting penetrated, give them an orgasm beforehand with some stellar oral sex, paired with a rim job.

Oral feels good for everyone, Start by licking and teasing, then move on to nibbling the backs of the thighs or their booty. This spark of passion and pleasure will ignite their desire and loosen them up for you. 

Make sure you’re squeaky clean

One thing that scares people away from anal in the first place is the idea of it being dirty. If you're the kind of person who is mortified at the thought of not being clean, rest easy: tidying up beforehand is relatively simple. How involved you want to get depends on your own needs. For some people, getting clean means only doing anal play after a shower, to make sure their booties are spotless. Other times, people play only after they’ve used wet wipes, or even after they’ve gone the extra step and douched.

If you want to make sure you’re clean down there, a douche is a quick and easy process that involves cleaning you out with warm water – and it takes just a few minutes. An enema isn’t necessary, but some people get a lot of pleasure out of the sensation. Curious? Go for it. You can buy enema kits online as well that hook up to your shower.

This isn't just about having a clean butt though. I would be remiss if I didn't mention the sex toys, penis, or fingers going into someone's rectum either. It is very important that those are all clean. Bacteria under the fingernails can cause or spread infections, and unclean toys make the spread of infection likely.

This all being said, the reality is this: anal sex can be messy. If you are serious about anal, you need to be comfortable with that reality, open to the idea of a little mess, and gracious to your partner about cleanup.

Play with your partner’s whole body

Just because you’ve built up to this big penetrative crescendo, don’t write off everything else your partner’s sweet bod has to offer. By now you probably know that if all you’re doing is thrusting inside someone, you’re probably not pleasuring your lovers. Anal is no different.

Start slow. Oral sex is the surest way to give anyone the ultimate orgasm, and if you're pleasuring them anally, a good orgasm first will always help your partners relieve tension and loosen their anus to receive your body or sex toys. Loving on your partner all over their body (while giving that anus plenty of love as well), may earn you the Partner of the Year award, or at least a line in their books as the most memorable use of a Friday night they've had in a long time.

When you start having anal sex, explore your partner’s body. Touch their nipples. Even better, depending on your partner’s equipment, play with their clitoris or balls as you take them from behind. Let them feel full of you while stimulating them, and watch how they go wild.

Your partner will love it – and if you’re using a dildo, your options just keep broadening. If you’re feeling bold, try hammering them while eating them out or giving them a blowjob. 

Before you get carried away, it’ll go over best if you talk to your partner extensively about what they want, and make sure you’re pleasuring them in all the ways they’ve asked. By incorporating their whole bodies and not just thrusting like a dog, you’re making sure you and your partner will want to do anal again and again.

A note on pegging

If you're pegging your partner for the first time, be gentle. Cisgender women and other folks with vaginas know what it's like to be filled by something through their own experience with vaginal sex, but first-timers with penises have never appreciated the filling sensation of penetrative sex before. In your first foray into pegging, anal intercourse is an intimate moment that calls for romance. Touch their skin. Engage with your partner's body lovingly. Cisgender men are usually never taught to enjoy the type of pleasure possible from being penetrated, and anal sex is a special moment where your trust is something they can't enjoy the moment without.

Use care when pegging, and be sure they know you're a receptive partner who can help them on this journey of finding the pleasure their anus has to offer. It may help to also start small. Use sex toys that are designed for anal training, and consider getting a slender dildo to start. Anal sex is intense, and medically reviewed research agrees that the best way to have safe anal sex is to start slowly, use lots of lube, and communicate.

Also, women (and everyone who's never been the one doing the thrusting before) take note: don't just ram it in there. A sexual activity like pegging calls for nuance, and just as with vaginal sex, you can't go hard straight away. Ease it in. Listen to your partner as the sigh or gasp, and adjust accordingly. With a little forward thought and care, you can give them anal sex so good, they'll be begging you please for more next time.

Start having the best anal of your life!

Practice makes perfect – and there’s no better way to practice than to start having fun tonight. You did your reading, now go do your homework. If you can’t get a training kit tonight, start with a finger. Just be sure to pack the lubricant.