A First Timer's Guide to Anal Sex

If you've been a Kinkly reader for awhile now, there's no way you haven't heard about anal sex. Since the butt is so jam-packed with nerves (and even a prostate for some!), there's a whole lot of orgasmic fun to be had with this area.

However, "hearing" is not the same as "trying"; and there are a lot of reasons people put off having anal sex—even if they're otherwise interested. Not only does the area come full of taboos and misconceptions, but it isn't nearly as simple as other types of sex.

Take oral sex, for example. Oral is as simple as "put mouth on genitals. Nailed it!". It might not be the best oral sex you've ever had; but it won't necessarily cause pain. Anal sex definitely has more steps than that!

I'm here to break down anal sex—and make it more approachable for your first time. Anal sex doesn't have to feel overwhelming; and it doesn't have to feel like this scary, unapproachable thing you've never tried.

Read: The Best Sex Positions for Prostate Orgasm

So, let's talk about what anal sex is (and isn't), walk through a simple step-by-step process to make anal sex pleasurable and fun—and then I'll leave you with some tips to aid in your exploration of anal play!

First, let's bust some anal sex myths:

Myth: Anal Sex Has to Hurt

Big myth #1: anal sex hurts. Anal sex doesn't have to hurt—at all. Anal sex gets its reputation as being a semi-painful activity because people do it incorrectly—or rush into it. Like I said earlier, anal sex has more "steps" to do it successfully than other types of sexual activities. This means that some people try to take the same "one and done" approach to anal as they've done to other sexual activities. That can really make it hurt.

In reality, if you've gently stretched, your body is ready for the size you're trying to take, you're relaxed and you've used lots of lube, anal doesn't hurt really hurt—at all. You can feel stretching sensations (if you're a vulva-owner, it's comparable to the stretching sensation you can get when using an extra-large toy vaginally).

READ: The Beginner's Guide to Anal Stretching.

But anal sex doesn't have to include any sort of sharp pains, dull pains, radiating pain or anything else. It can be entirely pain-free; all it requires is time, patience and getting to know your body!

Now, if you get really into it, you can definitely expect a bit of soreness the next day—but I think that's standard with a lot of rough sex.

Myth: Anal Sex Makes You Gay

Ahh, homophobia and toxic masculinity come together for this lovely bit of bullshit.

Nope, anal sex doesn't make cis men gay any more than jerking off their own dick makes them gay. (I mean, they're touching a dick!)

Telling you that it doesn't make you gay, and whether or not you believe it, however, are two different things. I can tell you it's not going to make you gay until I'm blue in the face; but if that's how you view it, you're going to continue to have those thoughts.

There's nothing I can magically say that will change your mind besides reassurance that anal sensations don't change who you're attracted to in the slightest. I'd recommend spending more time in the sex-positive sphere (like here on Kinkly!) to familiarize yourself with the idea of anal sex being a normal sexual activity before you continue with your interest in anal.

Nobody wants to come away from a sexual experience feeling guilt and frustration about what they did.

For a lot of people, the idea of anal sex is still relatively new—and one they've never had open discussions about. Seeing those open, communicative discussions happening all the time—in front of you—can help normalize your interests and feelings in a way that can reassure you that it's all totally normal—and awesome.

READ: The 5 Rules of Anal Play for Straight Men

Myth: You Can Go From Absolute Beginner to Anal Intercourse In One Day

The likelihood that you're going to be able to have anal intercourse on the receiver's very first day of anal pleasure is pretty slim. Why? The average human penis is about 1.5" in diameter. It doesn't sound like much; but when you compare it to a lot of the things that go on around the anus, that's a pretty big size.

Add that to the fact that most people new to anal are going to be nervous and still getting used to the brand-new, sorta-weird sensations—and the likelihood that you're going to go from "zero to intercourse" drops dramatically.

Most people find they need a week or two (at minimum) of anal play with fingers or toys before attempting anal intercourse. Some people need months. Not only does this give them time to get used to processing new sensations (anal can feel weird at first!), but it also gives them time to get to know their own body's cues for too much, too little and everything in-between. This makes for better sex communication in the long run.

Don't expect to achieve anal intercourse on day one. Instead, consider your journey to anal sex to be just that: a journey with multiple days and multiple pleasure sessions.

READ: How Should I Prepare Myself for Anal Sex?

That being said, some people do find that their body relaxes and stretches open more easily than other bodies do.

But you shouldn't expect your body to be one of them. If it is, grand! However, plan for some anal stretching or anal training ahead of time to make anal intercourse—eventually—something that's on the table.

Fact: There Might be Poop

Let's get real here: There might be poop. I don't say this to dissuade you; but I say this because I don't want to give you some unrealistic idea about anal sex. The butt is used to poop. Therefore, you might end up having some contact with it during anal sex.

That being said, the contact is generally very minimal. There might be a smear here or there. (Hey, I said we were getting real!)

To reduce the likelihood of coming in contact with anything, the recipient should try to have a solid bowel movement four to six hours before play. If your stomach is upset, you're constipated, or haven't "gone" in awhile, you might consider rescheduling your playdate. To help make this process as smooth as possible, some anal sex lovers choose to eat a bland, less-irritating diet when they know anal sex is on the table.

Don't forget about the magic of condoms, gloves, and other sex-friendly barriers, either. While they can be great for reducing the chances of pregnancy or STIs, they also form an additional barrier between your bodies and any potential mess. For example, if any mess happens during anal sex while the penetrating partner is wearing a condom, it will likely be towards the condom's tip—and the wearer can easily strip it off to remove the entire mess in an instant. This can be a quick clean-up way that reduces what "mess" the recipient sees—and reduces anyone needing to really come in contact with the things that worry you both.

If you're the receiver and worried about the mess, I'd recommend taking some solo time with a dildo before trying anal with a partner. You're not very likely to enjoy yourself in your partnered experiences if you're worried about how it's all going to look. By giving it a try with a dildo ahead of time, you can see about what to expect—and figure out if that's something you're comfortable sharing with someone else.

READ: How to Keep Anal Sex From Getting Messy

Fact & Myth: Enemas Can Reduce the Likelihood of Mess

Some people also recommend enemas for anal sex; but I highly, highly, highly recommend multiple practice enemas—weeks before the "main event". See, if you do an incomplete enema, or do it incorrectly, you actually leave more waste matter in the area you're trying to clean.

Enemas cause fecal matter to dislodge—which is its "hole" point (teehee). You then want your body to expel it to get that waste out of the way. If you do an incomplete enema, you actually can "add" more fecal matter into your workable area—fecal matter that's already dislodged and easier to come in contact with.

In addition, if you aren't gentle with your enema, you also could cause some tearing or soreness at the entrance—which will put a damper on your intercourse fun too.

Another mistake people sometimes make is using too much liquid—that can leave you hitting the bathroom too often to actually complete the act. And that's no fun either.

Enemas can ensure you're (pretty close to) squeaky clean; but they're also generally unnecessary for most people looking to have standard anal intercourse with a biological penis. Where enemas start becoming more important is when people start playing with large toys, anal stretching or fisting.

READ: How To Do An Enema Before Anal Play

However, if the idea of a mess is the only thing putting you off, enemas could potentially be a solution for you; just make sure you know what you're doing, don't do it too often and practice before you try to do an enema before an anal sex session.

Fact: Your Favorite Sex Positions Might Not Work

The anus is in a different spot from the vagina. This means that some of your favorite sex positions for vaginal sex might be off the table—and you might need to explore a bit to find new ones that work for your bodies and anal pleasure.

At the same time, even if the position is physically possible, it's quite possible that some of your favorite sex positions might not be a great fit for beginners to anal sex. Some sex positions encourage deep penetration—or make it difficult to take penetration slowly. You might need to table some of those sex positions until you're both comfortable and experienced with anal sex.

Consider this a new opportunity to explore new ways your bodies fit together—and experience the orgasmic joys of new sensations.

How to Have Anal Sex for the First Time

OK, you're better prepared about what to expect now. Anal sex shouldn't hurt and it won't change your sexual identity—but you might need to learn some new sex positions and see a bit of poop.

You're cool with all of that. So what's next?

Talk About Anal

Long before you have anal sex, you need to have a conversation with your partner about it. Remember how I said that anal sex can hurt if you both don't know what you're doing? That's what we're trying to avoid here. If you've done your reading but your partner is working solely on their own assumptions, you can end up heading down the pain train—and that's no fun.

So, long before the anal happens, you need to have a conversation about butt stuff. This doesn't have to be serious (and can even be laced with some arousing dirty talk if you want!). The important thing is that you've talked about it—and know you're on the same page. Here are some of the anal sex negotiations I'd recommend:

• How do you feel about the idea of anal sex? (For some people, it may be a hard pass - entirely!)
• How does the idea of receiving/giving anal sex make you feel?
• Poop might happen. Are we okay with that? (For example, some receptive partners prefer the insertive partner to remove and dispose of the condom and speak nothing of the mess if it happens. That's what makes them feel comfortable.)
• What lube do we plan on using?
• What sex toys do we have that can work for a warm-up? (If none, it might be time to get some!)
• What turns you on about anal sex? Are there ways we can incorporate that?
• When you think about anal sex, do you think about certain sex positions?
• Do we have some uninterrupted time coming up where we think we could try this?

Schedule Time

Nothing sounds sexier than "schedule" and "sex" in the same sentence, right? But in this case, it's accurate.

You can't start your exploration into anal sex with a short time limit. You just can't. Trying to speed-run through anal is what's going to cause pain. Unfortunately (and fortunately, if you like experiencing as much pleasure as possible), anal sex is just one of those things that takes time. And that means you need to have the time.

With our busy lives, that isn't necessarily easy. So, that's why I'm recommending scheduling time for your anal sex session.

Making sure you have an hour or two of uninterrupted time is going to give you both the reassurance you need to enjoy that hour or two without worrying about something getting in the way.

However you manage it, just make sure you have a couple of uninterrupted hours for your anal sex session. This is not an activity (especially when you're a beginner!) when you can skimp on time.

READ: The Key to Good Sex Isn't Spontaneity: It's Proper Planning

Be Aroused and Relaxed

While some sexual activities lend themselves well to "zero to 60" in a few seconds, anal sex isn't one of them. Everything about your anal sex experience will go more smoothly if you spend time being relaxed—and aroused—before you even begin. Since you scheduled your anal sex date (right?), some of that arousal might already be built into the anticipation of your anal sex date.

The rest of that arousal can come from flirting and teasing leading up to the time and place. Sexting can be a lovely tool for foreplay.

There's nothing wrong with spending some time touching one another and making out before you begin your anal sensation experience, though. A good, old-fashioned make-out session can be amazing for getting the juices flowing—literally and figuratively.

READ: 8 Tips to Turn Making Out Sizzling Hot.

Not only does arousal help all of the other sensations feel even better, but being aroused can help relax the body—which makes anal penetration more comfortable and easier to do.

It's a win-win!

Warm Up & Use Lube

Before you attempt anal intercourse, you're going to want to warm up with something smaller than the eventual size of what you'd like for intercourse. If you have sex toys, those tend to be the first choice; but a lot of people choose to go with fingers as well.

The important thing is: The anus requires a lot of gentle stretching before you jump into full-on penetration. This gradual, gentle stretching relaxes the area, adds to the arousal and makes it easier for the anus to stretch wide enough for a penis during the eventual intercourse.

If you're using fingers, start with one—and slowly move on to two fingers. Consider three or four; but, as always, communicate with your partner and see where they're currently at comfort-wise. Ensure your fingernails are trimmed down to the quick, with no sharp edges or hangnails. If you want to earn brownie points, after your fingernails are trimmed and washed, run each one over the broad side of your tongue with a bit of pressure. If anything hurts the tongue, you need to retrim it. Remember: The anus is just as sensitive and delicate as the tongue!

If you're using toys, start with a slim toy—and consider using a second toy, slightly bigger than the first after the slim toy. If someone is a complete beginner, aim for an anal toy diameter under one inch. If someone has used fingers before, a toy diameter under one and a quarter inches is generally a good goal. Ensure it's anal-safe with a flared base.

You might also consider anal dilation with something like the Odile. The Odile was specifically designed to help someone gently stretch themselves before anal sex. To do that, first slide an anal dilator into the butt. Then, simply turn the twistable dial at the base of the Odile. This causes the Odile to gently expand in size, millimeter by millimeter. This can allow for a gentle, slow stretching session that can help the body get ready for larger toys or partnered intercourse.

Either way, the goal is to gently stretch the butt open—so be gentle, move slowly and leave the finger/toy inside of the butt to allow it to gently relax the area for future penetration. If things feel a bit too slow to you right now, consider using a butt plug to enjoy other types of foreplay while you're using the sex toys or your fingers. You also can adjust your positions for making out or other types of pleasure (like oral or manual pleasure) while simultaneously doing this.

No matter what you're using, ensure you're using lots and lots of lubricant. Unlike the vagina, the anus provides zero lubrication. You read that right: zero. There is nothing to slicken things up and make things pleasurable. This means you need to BYOL: Bring Your Own Lube. Coat your finger or sex toy in lube and, for good measure, use your finger or the tip of the sex toy to coat the entirety of the entrance as well.

Regularly reapply the lube. If things feel a bit less smooth than they used to be, reapply. If ten minutes have gone by, reapply. It's hard to overapply lube*; but it can be really painful if you underapply.

(*Note: It is physically possible to overapply lube. It's really difficult; but it's possible. For most people, it just might lead to a few extra bathroom trips after anal sex to rid their insides of the excess lube. If you go extremely overboard, you might end up causing an enema-like sensation with lube mid-play. We're talking half the bottle in a single session, though.)