How to Love Anal Sex as Much as I Do

A comprehensive guide to taking it in the ass

Emma Austin
Oct 19, 2019 · 14 min read

I love anal sex, but I know plenty of people just don’t like it or aren’t interested in it.

That’s fine and totally understandable — I went through a period in my marriage when I really didn’t care to do it, and I was perfectly comfortable with that decision.

But a lot of people are somewhere in between. They’re curious about anal but want to approach it the right way. They fantasize about it and want the reality to live up to it. Or they’ve taken it in the ass before and didn’t enjoy it, but want to give it another chance.

There are better and worse ways to do anal. And bad anal sex isn’t like bad sex — it’s in another category altogether. So, it’s important to approach it the right way.

I know that from personal experience. Having my ass fucked feels amazing, but I came really close to swearing off anal completely.

How I Fell in Love with Anal (Twice)

My first times doing anal were the absolute worst. I thought my boyfriend and I were doing everything right — I agreed to do it, we used lube — but it only resulted in discomfort and pain.

Looking back on that relationship, I’m pretty sure he was a closet sadist, so I think that was a fine outcome for him. But it made me dread ever doing it again.

I changed my mind when I met the man I would eventually marry. I trusted him like I had never trusted anyone else before. I lusted after him when he wasn’t around and couldn’t keep my hands and lips off him when he was.

After a few months of amazing sex, I kept coming back to the same fantasy: I wanted his cock in my ass.

I only had terrible anal experiences up to that point, but he made me feel so damn safe. I knew I could try anything with him and it would be as good as it could be. I knew with complete certainty he would never go further than I wanted it to.

And I also knew that as much as he was turned on by the thought of fucking me in the ass, he would be turned off by me being in any kind of pain.

It went extremely well. Feeling his cock inside my ass was an entirely new sensation. This time, it was gentle, loving, tender, and so goddamn pleasurable. He fucked me slowly and I was overwhelmed with excitement that anal could be as hot as I thought it was — hotter, even.

We were young and stupid, so we committed an anal faux-pas or two. The only lube we used was spit and we didn’t talk about it beforehand — I just pressed my ass against his cock until he got the picture. But somehow it worked. It felt right. It gave me an orgasm. And instead of ending up sore and disappointed, I felt tingly with affection and couldn’t wait to do it again.

We did it every couple of months, but a year later my libido fell through the floor and I lost interest in doing it.

I didn’t want to have anal sex, but I was still very much into it. For about five years, I fantasized about anal sex, watched anal porn, and masturbated to the thought of being fucked in the ass. But whenever I fucked Mr. Austin, I left my ass out of it.

Well, you can only have frequent anal fantasies for so long before you just can’t help yourself. Five years into my ass-fucking dry spell, I was very pregnant, super fucking horny, and I wanted Mr. Austin to fuck my ass as badly as I wanted it the first time.

I’ve been having anal sex regularly ever since. And I’ve been thinking about putting together a few of the things I learned in an article (I’ve come a long way from spit and silence). Reading traceybyfire’s post about wanting to know what was so great about it gave me the final push. So, here it is, my advice for anyone who’d like to be fucked in the ass and have it be a thoroughly pleasurable experience.

Get Mentally and Emotionally Prepared

There’s some physical preparation that goes into anal sex, but there’s a ton of mental and emotional preparation.

It works best (and feels best) when you not only want anal sex but truly desire it. Feeling curious about it is a good start, but biting your lip at the thought of your ass getting fucked is better.

Two things work especially well for me: good porn and good communication.

I’m a fan of anal porn. It’s what made me crave doing it again. But there’s a lot of junk out there, and plenty that makes anal sex look like an ordeal, not an experience. Erika Lust’s His Was First in My Ass and the anal videos on Bellesa are good places to start.

Talking about it with Mr. Austin also helped me get there. It made me feel safe and at ease knowing that he knew exactly what I wanted and what I didn’t.

Then there’s the dirty talk. Having him tell me what he would like to do with my ass, describing in detail how he would touch, lick, and slowly penetrate my asshole, made me wet and desperate to do it.

Trust matters a lot, too. It’s hard to be emotionally ready for anal unless you can establish boundaries and know that your partner will respect them (without whining, complaining, or trying to get you to compromise).

One way to set boundaries is to decide exactly what you want to do. Instead of telling your partner you want to try anal, try easing into it by saying something like “Tonight, I’d like you to play with my asshole but no penetration” or “I just want to try a finger for now, and if I like it, maybe we could try with your cock another day.” If you can trust your partner not to violate those rules, it will make things more predictable and make you a lot more comfortable, a lot less nervous, and a lot less worried.

In fact, this was one of the big reasons I couldn’t enjoy anal with one partner, but couldn’t help loving it with another. When I first tried it, I was with a partner I knew on some level I couldn’t trust — instead of respecting my boundaries, he always tried to push past them.

So, if you’re not with a partner you feel you can totally and completely trust, it’s best not to try anal with them. (Bonus points if you dump their ass — yours deserves better!)

Lube Is Essential

Your ass isn’t self-lubricating, and inserting anything into it dry is not going to be a pleasant experience.

You need lube. And even though I powered through it once, spit really doesn’t cut it. Even if you can get through it with spit, it will feel twice as good with proper lubrication.

The great thing about anal play is that you can use any type of lube.

If you’re playing with a butt plug, dildo, or other sex toy made of silicone, you should use water-based lube. It won’t damage your toy, and it will be easy to clean once you’re done. The only downside is that water-based lubes need to be reapplied more frequently.

Lots of people swear by oil-based lube for anal, and a lot of anal-specific lubes are oil-based. I tried Boy Butter and I found it worked quite well, but it’s not my favorite. The best part about oil-based lubes is that you can go longer without reapplying. That would be a huge perk for anal (I don’t like having a cock taken out of my ass and inserted again — if it’s in, I want it to stay in), but for some reason (I’m not entirely sure why) I come very quickly and extremely hard from anal so I never get to enjoy those long-lasting properties.

I’ll stick to using oil-based lubes for handjobs and penis massages. For anal, my go-to is silicone. I found silicone-based lubes to be the slipperiest, and that makes it extra fun to use. The only downside is that it can’t be used with silicone toys.

If you’re using condoms, make sure you avoid all oil-based lubes. They wear down the latex and compromise the protection the condom gives you.

Start Small

Your goal might be to get a cock or a dildo in your ass, but that’s not the best place to start.

I’ve heard and read a lot of people’s anal sex stories (good and bad) and it’s common for couples trying it to go straight to cock. That’s a very brave thing to do, but not really advisable.

If you’re not used to anal sex (and frankly, even if you are), you will probably need to build up to it with something less girthy. A finger or a slim butt plug is a good first move. Once you can comfortably enjoy the sensation of a finger in your ass, you can take something thicker.

It’s even better if you don’t start with any penetration at all — anal stimulation can stay at surface level and still be very arousing.

I find the best way to prepare for anal is to have my asshole rubbed gently for a while. A lubricated finger (in this case, spit’s alright) works well, and so does a tongue if your partner’s into giving rimjobs.

It’s all about making yourself physically comfortable. Even if you’ve done all the mental and emotional prep work, you’re still dealing with a muscle that can tighten as a reflex. You have to get used to overriding that reflex before you can go into full-blown penetration.

You have to walk before you can run. Until a finger or a butt plug feels good and comfortable in your ass, don’t go any further. A cock or dildo in your ass won’t feel good until these do.

Kegel Exercises Help

I had to get control of my pelvic floor when I was suffering from vaginismus. My vagina was basically acting like an asshole (in more ways than one): contracting whenever something tried to penetrate it. Kegel exercises helped my body relax so I could enjoy pain-free sex again.

The same philosophy applies to anal sex When your muscles tighten involuntarily, you need to relax them before you can proceed further. Kegels helped me do that — getting control over all the muscles I have down there could help me relax and ease into it.

If you want to go hardcore or make sure you’re extra ready, you can get yourself an anal training kit. They’re a set of butt plugs (usually three or four) that are progressively larger in size. You wear the smallest one until you get accustomed to it, and then you can move on to larger sizes.

Having Anal Sex Doesn’t Mean Doing Anal Only

I love anal sex and write about it once in a while. But I might not have done a good enough job of conveying what I really do. I never actually do plain, straight anal sex. I always combine it with other kinds of stimulation.

When Mr. Austin is fingering my ass, he’s usually licking my clit at the same time. On some occasions, he’ll give me the full trifecta: mouth on my clit, two fingers in my pussy, and one in my ass.

When I’m getting my ass fucked, I make sure I’m getting clitoral stimulation at the same time. Depending on the position I’m in and how easy it is to get to my clit, I’m either using a vibrator, my fingers, or enjoying Mr. Austin’s fingers.

I go for that extra stimulation in part because it always leads to a blended orgasm. I get off seriously well when I’m getting anal and clitoral stimulation at the same time.

But it also makes it easier to get going, too. I find anal sex entirely comfortable — except at the beginning. Getting started always involves some kind of discomfort. No matter how slowly we go, no matter how horny I am, and no matter how much lube we use, that initial discomfort is always part of the experience. That’s possibly because of Mr. Austin’s size — he’s no soda can cock, but he is thicker than average. I have occasionally wondered if I wouldn’t feel that initial discomfort if I got my ass fucked by someone who had a more manageable size. (Slim guys hmu.)

Getting my clit stimulated makes it easier to get through that initial discomfort. It takes the focus off it and lets me get to the part I enjoy more quickly.

Have an Orgasm First

I find it helps to have an orgasm before moving to anal. If you’re multiorgasmic, it’s a great way to thoroughly relax your body and put you physically at ease for some back door action.

It can also make you a bit more sensitive, which will increase your odds of having an orgasm from anal (your odds go way up if you keep the vaginal or clitoral stimulation going at the same time).

And not everyone can get an orgasm from having their ass fucked. So, if you want to have anal but can’t finish from it, it’s a good idea to get yours beforehand.

Take Charge of Your Ass

It’s your ass getting fucked, so it’s important for everything to go at your pace. The best way to do this is to push your ass back on your partner’s cock instead of having them ram their cock into you.

If I feel particularly ready, I’ll let Mr. Austin ease himself into me. Most of the time, though, Mr. Austin won’t move at all. He’ll lay on his side behind me with the head of his cock pressed up to my asshole and I’ll push back onto it. He waits patiently while I get used to having him inside me and doesn’t take over until I’m ready.

Your ass is going to feel much more relaxed if you’re the one taking care of the motions.

Find the Right Position

Getting in the right position is key. There is definitely an element of personal preference here. Physical configuration could also be a factor (Mr. Austin curves left. Does it make a difference? Who knows.) And those that allow penetration at a 45 degree angle are generally ideal.

I love variety in my sex life, but when it comes to anal sex I don’t switch things up too much. I don’t bother with any crazy positions. I haven’t been able to enjoy doggystyle anal, either. Instead, I stick to three positions that combine comfort (internal and external), give Mr. Austin more control (because of his length, I don’t always want him to put the whole thing in), and easy access to my clit.

I alternate between prone bone, missionary, and my go-to, must-have anal sex position: spooning with one leg held up. All of them have their advantages, so the one I choose depends on what I’m hoping to accomplish and experience.

I love doing prone bone (in which I lay flat on my stomach, with my ass pushed up very slightly) because I can tuck a vibrator between my thighs and ride it while Mr. Austin rides me. It can also be thrilling to be so completely underneath him. I feel physically under his control, with the whole weight of his body pressing me down. There’s a slightly dominant edge to it that feels really good in the context of a trusting partnership.

Missionary anal feels really good because I can always get a good angle from this position — it always feels like Mr. Austin’s cock is pumping me just the right way. Because we do this position with Mr. Austin standing while I lie at the edge of the bed, he’s not leaning over me at all, which gives me perfect, unimpeded access to my clit so I can jill off while getting fucked. And it gives Mr. Austin a damn fine view of the action, which turns me on more than I want to admit.

But my default position is spooning while holding one leg up. Most of the anal sex I have takes place with me laying on my side and arching my back. Keeping my leg in the air is more muscle work than I would normally care for, but I finish so damn quickly in this position that I never get bothered by it.

Spooning is great because it gives me the most control. I can take charge of the action, the pacing, and how much of him I want to take in at any given time. With my leg up, I can access my clit, but more importantly, so can Mr. Austin. Having him reach over and rub me while I’m getting fucked is the kind of hands-free experience I can get behind (even when I’m in front). As far as I’m concerned, that’s the piece de resistance when it comes to anal sex.

This position also makes me feel exposed, which I consider a perk. I feel like I’m splayed and displayed like a pornstar, and something about that just gets me hot. (I know, it’s confusing, because Mr. Austin is behind me and can’t see much. But it just works.)

Again, this is all personal preference. You’ll have to find the position that feels best for you and puts you at ease. Maybe that’ll be doggy style. Maybe you’ve got the thigh strength, muscle control, and confidence to get in cowgirl position and really take charge of things. But if you’re not sure where to start, any of the three positions I discussed are good, basic ones to try.

Only Use Sex Toys with Flared Bottoms

If you’re going down the sex toy route, make sure you’re using sex toys that are safe for anal play. That means, especially, making sure they have a flared bottom (a base that’s larger than the rest of the toy).

Basically, you don’t want to insert the entire toy into your ass. Part of the toy needs to stay outside your body so you can easily pull it out and retrieve it.

Butt plugs are the most obvious choice for anal play, but you can use dildos and vibrators, too, as long as they have the right kind of base.

Don’t Do Ass-to-Anything

Anal is always the last item on the menu when I’m having sex (well, if you don’t count Mr. Austin pulling out, jerking off until he comes on my ass, and then a breathy cuddle sesh). Once something’s gone in my ass, it doesn’t belong in any other orifice.

Ass-to-mouth and ass-to-pussy is just not sanitary. It used to be a huge trend in porn, but that doesn’t mean it’s a smart move (and sometimes it’s accomplished with editing, not by anyone actually double dipping).

If you want vaginal or oral action after anal, make sure the cock or toy that fucked your ass gets washed really well before you proceed.

Get the Anal Experience You Deserve

Anal sex isn’t going to be for everyone. Some people just don’t get turned on by the idea of getting their ass fucked. Others might love fantasizing about it but really don’t think they would enjoy doing it.

But if it’s something you do want to try, you owe it to yourself to do it in a way that is safe, comfortable, and in line with your pleasure.

Love, Emma

Articles about sex, love, and relationships by Emma Austin

Emma Austin

Written by

I write about sex, love and everything else that matters to me. | Links to my podcast, blog, and social media: https://linktr.ee/EmmaAustin

Love, Emma

Articles about sex, love, and relationships by Emma Austin

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