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ANAL SEX

A First Timer's Guide to Anal Sex

Published: FEBRUARY 15, 2022
Presented by KINKLY SHOP
For anal sex newbies, patience, planning and communication are key. Oh, and lube. Lots and lots of lube.

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.

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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!

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.

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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.

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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.

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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.

Two Odile dilating butt plugs. The left butt plug is fuschia and the right butt plug is neon blue. Both plugs feature a long colored end, to be inserted into the anus, and are topped with a black dial that can be turned to expand the dilator. 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.)

Possibly Stop Here

Are you mid-way through playing with your favorite sex toy and things are feeling pretty tight? This is probably where you're going to want to stop.

I know, I know: Anal intercourse was the end "goal". But one of the big things about anal is knowing your limits—and communicating them. If your body is already at its limit from a toy that's slimmer than your partner, trying your partner is going to be painful. If you're finding your entrance is already sore during the warm-up, the actual intercourse is probably going to lead to some pain.

Sometimes, unfortunately, you have to "call it" before you make it to the intended event—even if you really, really want to keep going. Sometimes your body just doesn't cooperate with the way the mind wants to do things. That sucks, but it happens—and it happens more with anal sex than it will with other types of sexual activities. An upset stomach, stress from the day or soreness from earlier bowel movements can easily derail your anal sex plans.

So don't be afraid to stop at this point if you need to—especially if the receiver is new to anal penetration. You shouldn't expect to make it to anal intercourse on the first few sessions, particularly when anal penetration is new and the sensations are all novel. It's going to take some time to get to the point of anal intercourse.

And don't feel bad for stopping—even if you haven't fully inserted a dildo yet. There's always another day to do it. Your sex toys (or your partner, presumably!) aren't going anywhere.

READ: IBS and Anal Sex: Why It Doesn't Have to Be a No-Go

Use Even More Lube

Remember: Lube is definitely your friend for anal intercourse. Before you dive into penetration, I want you to fully lubricate the penis (or dildo) you're using. For good measure, take a moment to re-lubricate the anus after your warm up, too.

Keep that lube bottle nearby—because lube and patience can really make or break an anal sex experience.

Go for Super-Slow, Super-Gentle Penetration

OK: you're both really turned on, your partner is warmed up and your penis is so covered in lube that it's dripping on the bedspread. What's the next step?

The name of the game here is "penetration so slow that it's not really even moving." As we'll talk about in the tips section, that might also mean you need to readjust your sex position. You'll want a position where the penetrating partner can easily hold and sustain their own weight in the movements between "not inserted" and "fully inserted". Missionary, for example, can make that very difficult, while doggy style makes that much easier.

Instead of going for a full, smooth, first stroke, barely insert the tip—and wait there. On the penetrating partner's end, this can feel almost like you're being too patient, but I promise: There's a lot of sensation going on on the receiver's end.

Ask your partner to let you know when they want a bit more—and provide it. Ideally, find a position where the receiver can push back onto the penis (like a rear-entry sex position) instead of requiring the receiver to move—but both options can work.

Slide in less than half an inch with each push. We're going slowly.

This is where your individual penis anatomy can make a difference. Some people's penises are thickest at the tip, while other people's penises start thinner at the tip and get thicker towards the base. Use your knowledge of your own penis to determine how much to insert at a time.

If your partner has already comfortably "conquered" the thickest part of your penis, you can start sliding in an inch at a time before pausing. If you're still working towards the thickest part, continue on the small, slow increments to allow your partner's body to adjust to the sensations.

Once fully inserted, ensure you stay still. There's still a whole lot of sensations going on here—especially when it comes to depth. Wait for your partner's go-ahead—and then start with super-slow, patient thrusts.

Reapply lube as needed. Remember: It's hard to have too much lube! If you're using a condom to reduce the likelihood of mess, remember condoms can cause a bit of extra friction and may require you to apply lube more frequently.

Don't forget about communicating with your partner even after you're fully inside; ask them what they'd like. Especially for the first time having anal intercourse, the sensations can be extremely overwhelming. You may not progress beyond a slow, patient thrust—and that may be more than enough for them. Don't forget about pleasuring them in other ways—like stimulating the clitoris or stroking the penis to ensure everybody gets as much pleasure as possible out of the experience.

Especially if the receiver is new to anal intercourse, be aware the area can get over-stimulated faster than during vaginal intercourse for most. The anus can also be more sensitive to friction. Aim for your orgasms within that timespan—or, potentially, have a game-plan for whatt to do if penetration needs to end early due to soreness.

It's very possible you may not get fully inserted the first time (or subsequent times!) that you attempt anal intercourse. Depending on where the widest part of your penis is, this may be a large jump for the receiver to take. If you're open to shallower anal penetration, consider using the OhNuts penis limiters to reduce penis length and stick to the areas that have been comfortably inserted.

If it's difficult or frustrating to start anal penetration while not being able to finish a full stroke, I'd recommend purchasing a dildo that's similar in size to your penis. This way, you both can add it as part of the warm up and foreplay; and by the time intercourse rolls around, the receiver's body should be better adjusted to a thicker size.

Anal Sex Tips for Your First Time

Finally, let's get into some anal sex tips to ensure your anal sex is as awesome as possible:

Don't Rush Intercourse

If you read all of the previous points, you know that expecting intercourse the first time you try something anal-related is probably not realistic. Even more so, you should expect to spend a decent amount of time on foreplay before you make it to the part that includes intercourse.

READ: 10 Foreplay Games to Add Some Heat to the Bedroom.

But even beyond that, there's a good reason to take your time meandering to the "final" intercourse: The longer you spend relaxing, stretching and getting aroused, the better anal sex can feel. Just like edging can be amazing, drawing out foreplay and building anticipation can feel amazing before anal intercourse in its own right.

So, if you find your body needs a bit more time to prep for anal intercourse and you're starting to feel self-conscious, try to reframe things a bit. The eventual "reward" of hotter and more intense sensations can make it all worth it for everybody!

Choose Your Anal Intercourse Position Carefully

While it can be tempting to focus on pulling off the hottest anal sex position you can imagine, it's vital that you find an beginner-friendly anal sex position to start.

As "patience" is the name of the game, you want to ensure any sex position you choose allows the penetrating partner to easily hold up their own weight—and doesn't require them to strain too much during the penetration process. Minimize the likelihood that the penetrating partner will penetrate too quickly due to muscle fatigue or balance—and use sex positions to make that less likely.

The same thing also applies to the receiving partner. While a lot of people recommend receiver-on-top sex positions for beginners to anal, I'd recommend approaching that cautiously. It's just as easy for the receiver's legs to tire—and cause them to slide down more quickly than they intended.

My suggestion? Consider something like these:

Cornerback Sex Position: The penetrating partner is lying on their side, propped up by their elbow. The receptive partner straddles their hips, lying on their side perpendicularly to the penetrating partner.

The Cornerback Sex Position lets both the receiver and the penetrator fully relax. This can be fantastic for gentle initial penetration—and shallow penetration.

Kneeling Fox Position: The receptive partner kneels and leads forward to support themselves on their hands. The insertive partner kneels behind them, with their knees between the receptive partner's knees, holding their stomach for penetration.

The Kneeling Fox is a modified version of "receiver-on-top" that's less likely to fatigue either partner. Think of it like the receiver "backing onto" the penetrating partner. Just keep in mind that the folded legs can put legs to sleep faster than in other positions.

Selecting a sex position that doesn't allow deep penetration is also a great idea. Not only can this avoid uncomfortable sensations, but it can reduce penetrating happening too quickly or too deeply—which can be really uncomfortable for receiving beginner.

It's important that you choose an anal sex position that allows the receiver to relax. This may include using sex furniture to make that goal easier to accomplish. You want the receiver focused on relaxing and receiving; any strain on any muscles is likely to cause the anus to tighten up too. (It's surprising how many different stresses cause us to tighten the butt!)

For example, you might consider Liberator sex furniture like the Flip-Ramp to rest underneath the abdomen to support the mid-section during doggy-style for more comfortable penetration. The Wedge could be used to lift and support the hips during from-behind sex to make it easier for the receiver to relax. The Jaz could be used to elevate the hips while the receiver lays on their back during the initial warm-up foreplay; it makes for much easier access.

Double Mount Penetration Position: The receptive partner lays face-down with a piece of sex furniture underneath their hips to prop them up. The insertive partner kneels behind them for penetration.

The Double Mount Penetration Position is a great example of how sex furniture can come to your aid. The Liberator Bon Bon provides hip support—which allows the receiver to fully relax into the experience instead of worrying about quaking thighs.

Either way, use all of the tools at your disposal—from sex furniture, to better sex positions, to lots of open communication—to ensure you're choosing sex positions that set you both up for anal sex success.

You Can Prep in Advance

Sometimes, quickies are on the menu. You can have quickie anal too; but you'll want to be careful how you pull it off. Unfortunately, some people assume "quickie anal" means skimping on foreplay and using more lube to make up for it.

On the contrary, pulling off anal sex quickies actually takes a bit more creativity—and you'll find anal sex toys can become your best friends for this. If you're hoping for public play quickies, consider slipping in anal plugs ahead of time while the two of you are out. (Pack plastic disposable baggies to place the used ones in when transitioning to intercourse.)

If you're short on time at home, consider prepping your own body in advance; that can be done with a bit of time in the bedroom with a dildo, or it can include using anal vibrators or butt plugs at home.

While nothing beats the intentional focus of fingers and sex toys doing the stretching, busy lives call for workable solution; and you can find that pre-emptive sex toys can help do some of the prep work and shorten the time needed to prep for anal sex.

Get Ready for Some Seriously Hot Anal Sex!

Remember: Taking it slow at the beginning of your anal exploration is totally fine—and entirely expected. You don't jump into any new activity as an expert; and the smoother transitions and faster acclimations will come later on as your body gets used to anal sex and how the two of you fit together.

Take this time to really enjoy the initial exploration of anal sex. You'll never really get to "do it again for the first time" this way ever again; so make sure you value and treat the unique sensations as the awesome experience that they are—and don't be in such a rush to "get good."

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Mistress Kay

Mistress Kay has a fondness for all things sexual. With a house that's quickly running out of room for all of her reading and vibrating pleasures, she spends her free time reading, writing, and learning about the sexual universe with her partners. She can be reached at Kinky World.


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