First Time Anal Sex: The Curious Bum Lover’s Guide to Have Anal Sex

If you’re wondering how to have anal sex, but been too afraid to try it, here’s a full first time anal sex guide for all the curious bum admirers.

There is probably no sex act more maligned, misunderstood, and feared than anal sex. Especially for a first time anal sex experience, it’s just something most people love fantasizing about but can’t bring themselves up to give it a try. Are you one of those people? Well, read on, because here’s a complete guide on how to have anal sex for the first time, and make sure it’s a great experience too!

The very first question that haunts us – Does anal sex hurt?

If you’re thinking right now, “Yeah, but I heard it hurts and it’s really uncomfortable,” then you obviously heard that from someone who had a traumatizing anal sex experience. In that case, yes, they’re completely correct.

But, in all probability, their partner tried to reenact the latest porno he watched where the couple just decided to have “spontaneous” anal sex. Come on now, you know that isn’t how it works. But even after all the preparation, you still may not like anal sex, and that’s completely fine. However, you shouldn’t knock it before you try it!

[Confession: What anal sex felt like – both mentally and physically]

Firstly, getting back to the question, does anal sex hurt, there are a lot of false assumptions about anal sex, and the worst one is that it’s supposed to hurt.

The very idea strikes fear into the hearts of countless women, and it’s assumed that the only reason to ever do it is because one’s boyfriend or husband really, really wants to.

This could not be further from the truth. When done right, anal sex can be incredibly stimulating to the woman *or man* who is receiving it. Of course, the assumptions don’t come out of thin air. Most people don’t understand the right way to do it, and when done wrong, it will be uncomfortable – or worse! [Read: How to make anal sex pain-free – The happy bum guide]

Anal sex and the pain we associate with it

Women who have tried it most likely did so when they were younger. They had a young boyfriend who had no idea what he was doing, and he just tried shoving it in like he would with vaginal sex. At best, he squirted a bit of lube. The woman, with the scalding memory of her first time anal sex experience in mind, would then swear she’d never try it again, and she’d tell her girlfriends how horrible it was. [Read: The biggest misconceptions about anal sex]

The taboo around having anal sex

Anal sex has always been a huge taboo, and often considered sinful. People assume any woman who would want it is some sort of freak, and others believe that any man wanting to engage in the act, even with a woman, must have some deep-seated homosexual tendencies.

This is all quite stupid really. Don’t let ignorant people stop you from enjoying anything. Just the taboo breaking itself can be a huge turn on for anyone. [Read: 14 ways to get your partner to open up and communicate about sex]

The real pleasure points that arouse men and women

The clitoris is an amazing thing. How amazing? Anal sex can actually stimulate it and bring many women to intense orgasms. You know those iceberg diagrams, where what you see above the water is only 10% of it? That’s kind of like the clitoris. What you see above the skin is a fraction of what’s there.

The G-spot in the roof of the vagina stimulates the clitoris from below. And from where we all know it to be, the clitoris splits like a wishbone and runs down along both sides of a woman’s vaginal lips. It makes it as far as the perineum, next to the anus. When done right, anal sex can stimulate the tips of these extensions by expanding the sphincter. And the penetration, even though not vaginal, can stimulate the G-spot. [Read: How to find and tingle her G-Spot without having to use a flashlight]

First time anal sex – The steps you need to follow when you have anal sex

Anal sex is not something for a random hookup. Don’t have anal sex on a whim, and not if you want to make sure both of you have a great time together. [Read: 13 untold sex secrets you definitely need to know!]

#1 The warm up. Couples should spend at least a month making love in more traditional ways before they even think about trying it.

And then, especially if it will be the woman’s first time having anal sex, they should approach it slowly. A couple that doesn’t trust one another should get over that before attempting anal sex. [Read: How to prepare for anal sex – The beginners’ guidebook]

#2 Start shallow. Before going for the whole shebang, especially if it’s the very first time you’re having anal sex, start in the shallow end with a bit of butt play. Once a woman is already wet, either after oral or vaginal sex, the man should put a lot of lube on one finger. Press the finger against her anus and rub very gently. After a few minutes of this, slowly push the finger in.

#3 Try to relax! The woman should relax her sphincter muscle and remember to breathe. This is very important, because anxiety or shallow breathing will only end up involuntarily tightening the sphincter and that’s definitely going to hurt.

#4 Reciprocate it. Take it extremely slowly, and do this a few times before you try the real thing. And gentlemen, it’s only fair, if she wants to try doing the same to you, let her. There’s a good chance you’ll like it, and that doesn’t make you gay! Bonus here, it’ll also help you understand the sensations so you can work your way your partner’s bum keeping her pleasure and pain tolerance in mind. [Read: What is pegging? All the hidden backdoor facts to get a guy started]

#5 Nice rims. A rim job, or rimming, is where one person uses their tongue and mouth to massage another person’s anus. A lot of people actually enjoy giving rim jobs, and it’s incredible for the one receiving.

After a shower where you wash yourselves thoroughly, try rimming her. You’ll need to work together to get over any discomfort you have with things like this. It will be worth the effort. [Read: The rimming guide to master eating ass and do it like a pro]

#6 Massage and relax. Rimming, or any gentle massaging of the anus with lubrication will help relax the sphincter muscles. This will feel amazing for her, and is a great way to prepare for anal sex.

Try massaging her anus while stimulating her clitoris, or fingering her to drive her wild. To be safe and prevent any infections in her vagina, don’t give her oral sex after rimming, or finger her after touching her anus.

#7 Final preparations. Once you’ve experimented with some butt play and become more comfortable with the idea, you’re ready to take the final step.

A note on protection first: Unless you are in an exclusive relationship and are both disease-free, condoms should always be worn. The risk of HIV transmission skyrockets with unprotected anal sex. Other diseases can be transmitted this way as well. [Read: The risks and dangers of anal sex and what you need to be prepared for]

#8 Your first anal sex experience. Begin your first anal sex session with a hot shower or bath to relax. A glass of wine or two will also help loosen you both up in both a mental and physical sense. Begin with foreplay as you would any other sexual encounter. Stimulate her vagina, and if you can, bring her to orgasm once through oral or vaginal sex.

Start with rimming, or if you haven’t enjoyed that, some finger play. Gently massage her for at least five minutes before even putting any pressure inward. Add more lube to her anus, and a lot more all around one finger, and then gently slide the finger in. Slowly finger her for a few minutes to ensure she’s well lubricated.

#9 The grand entrance. It’s time for the man to lubricate his penis, or the condom covering it. Only water-based lubricants should ever be used with condoms for any type of sex. Don’t be afraid to use a lot, and put another dollop on her anus. You can use whatever position you’re comfortable with. Woman on top, missionary, and doggy-style *regular or sideways* will all work. [Read: 12 anal sex positions that make backdoor sex feel so darn good]

#10 Sliding it in. Gently. Very gently, push the tip of the penis against the anus. The woman must relax her sphincter muscles and continue to breathe. It should slide in fairly easily, but go extremely slowly. Go in about two inches and then stop and wait. Don’t do anything for two minutes, no just the tip to and fro, or frenzied humping.

Let her get used to the feeling of having anal sex for the first time. Communicate, touch each other, and kiss if you’re in a position that allows it. It may help for the man to stay completely still and have the woman do the moving at first. [Read: 22 reasons why women fake an orgasm so often]

#11 Move in and out. Now slowly pull out just a fraction of an inch, and push back in. Repeat this, but with each successive pump, pull out a little more, and push in a little deeper. Do this slowly for a few more minutes, and before you know it you’ll be having amazing, hot, dirty, kinky, mind-blowing anal sex.

#12 Focus on everywhere else too. Once you’ve got it going, and know how to have anal sex gently, kiss, suck on a breast, and rub her clitoris with your finger, or better yet with a vibrator. Don’t start pumping away furiously like they do in bad porn, keep a moderate pace. Finally, don’t forget to enjoy yourselves. [Read: How to experience anal sex orgasms with the right moves]

See? Your first anal sex experience wasn’t so bad!

Okay, we’ll get to more details on how to have anal sex now. But remember this, not every woman will like having anal sex, just like not every woman enjoys any given sex act. If you do it right though, it will not hurt. Don’t confuse discomfort for pain, the first time you have anal sex will probably feel pretty strange. But as long as you follow these instructions, it should not hurt. Obviously, if anyone does feel any pain, you should stop immediately.

Follow these steps on how to have anal sex right, and the chances are that you’ll both enjoy it. Try a few more times later, you’ll find that as you both become more comfortable and confident with it, it will only get better and better. If you don’t like it, hey, at least you tried. We could all use a little more kink in our lives.

[Read: The top 50 kinky ideas you need to try at least once for a really sex relationship]

How to prepare for anal sex – The full guide

Now that you know exactly how to have anal sex, be it for the first time or the tenth, there are some things you should always remember. And that’s preparation.

Anal sex can be extremely pleasurable, nonetheless, as there are thousands of nerve endings around the opening of your anus. So as much as it can give you pleasure, it can also cause pain if you rush into it, or get too vigorous.

How to have a good first experience with anal sex

We all want our first time to be a memorable experience, so here are the must-do steps on having anal sex for the first time.

#1 Work your way up in size. If this is your first time having anal sex, you have to understand that your rectum is a small and tight hole. Having a full-sized penis squeezed into your anus will likely place you in the same emotional sphere as a dog who’s getting his anal glands cleaned for the first time – there will be shock, there will be horror.

Before having anal sex, get comfortable with your anus. When masturbating or having vaginal sex, try putting a finger in your rectum to relax it and start to get a sense of what it feels like. Once you do that, you can try using a thin sex toy to slowly work your way up in size. [Read: Female masturbation: 17 facts about the naughty secret]

#2 Clean yourself beforehand. Many people wonder how to have anal sex, but are nervous to actually have anal sex because they think it’s some sort of dirty act. That’s actually not the case, though. Your anus is responsible for removing toxins and cleansing your body. Basically, that ass is pretty squeaky clean. But you can wash before having anal sex if it makes you and your partner more comfortable.

#3 Lay off the spice. If you’ve made a plan to have anal sex, I recommend not eating a bowl of spicy curry or hitting up your favorite Mexican restaurant right beforehand. Foods with a lot of spice will give you loose stool. This may be a small detail, but trust me, follow it. Your ass will thank you.

#4 Relax your muscles. To have an enjoyable anal sex experience, you can’t have a tense rectum. You’ll need those anal sphincter muscles to be nice and calm. That way, you’ll be able to take the object in much more smoothly.

To relax your muscles, you can have your partner perform rimming on you. Rimming is where your partner licks and sucks around your anus, which does a great job at relaxing those muscles. If that doesn’t sound like your cup of tea, another way to achieve the same thing is with butt plugs. [Read: Do women actually like anal sex? The truth guys wanna know]

#5 Communicate. Don’t be shy about telling your partner to slow down or to stop. Your partner doesn’t know if he’s pushing too hard or if you’re feeling that you need it to slow down. You need to voice this. So if their fingers, penis ,or sex toy isn’t doing it for you, say it loud and clear. [Read: Why guys really enjoy having anal sex and how to know if you should give it a try]

#6 Wear a rubber. Don’t think that you can be rubber-free by having anal sex. You can still contract an STI through this act. In addition, if he doesn’t cum in your ass, you’ll also have a chance to become pregnant.

Everyone knows not wearing a condom feels better, but you know what also feels better? Not having to call your partner and tell them that you’re infected with an STI, or even better, not having to support a child for the rest of your life before you’re ready. And if your partner is telling you not to worry, well, then they can find another ass to stick their dick in. [Read: Condom types and how they can improve your sex life]

#7 Lube, lube, lube. We need to say this one more time: lube. Lube it up. Lube it the hell up. Unlike your vagina, your anus does not self-lubricate. Usually, people who complain about the discomfort of having anal sex were not properly lubricated. And this makes total sense.

It’s like forcing a hotdog into a dry bun – you need mustard and ketchup, people. So, don’t be shy with the lube. Make sure that penis is dripping wet before putting it inside you. [Read: How to use lubricants to liven up your sex life instantly]

#8 Get the position right. If this is your first time having anal sex, there are specific positions that will help to ease you into the sensation. There are two positions that seem to be a favorite for anal sex. You can start by lying on your side and having your partner spoon you. This gives you a little more control over the situation.

Or, you can do doggy style. This seems to be the best position for an easy insertion. However, because your partner can’t see your face, they won’t be able to see your reaction, meaning that you’ll need to remember to communicate. [Read: 9 ways to make doggy style your favorite position]

#9 Anal sex shouldn’t hurt. Contrary to popular belief, having a penis inside your rectum isn’t supposed to cause you pain. If it’s hurting, then you’re not doing it right. Remember to use a lot of lube while having anal sex, which should prevent any pain from occurring. If you’re still feeling pain and your partner is heavily lubricated, then try changing the position. It could be the angle that isn’t working for you. Either way, it can be an easy fix. [Read: Is anal sex hurting you? You’re probably making 1 of these 12 mistakes]

#10 Keep hygiene in mind. After having anal sex, your partner’s penis, fingers, or toys cannot go into your vagina. When you’re caught up in the moment, it’s easy to overlook these things.

But seriously, you have to keep this in your mind during sex. The anus has bacteria that can cause vaginal infections, so before having vaginal intercourse, make sure that your partner washes his penis, fingers, or toys with warm water and soap.

#11 Use sex toys. When it comes to learning how to have anal sex, remember that the act isn’t strictly for the penis only. In fact, you can have a great anal sex experience using fingers and sex toys. Have fun with it!

Try anal sex with sex toys such as butt plugs, anal beads, and vibrators. They can stimulate areas of the rectum that the penis simply cannot. Oh, but don’t forget, even with sex toys, you’ll need to lubricate them. And don’t forget to wash them before using them in your vagina. [Read: 15 most common types of sex toys all singles and couples MUST know about]

#12 Do it with someone you trust. Okay, you may be a fan of one-night-stands, but if this is your first time having anal sex, then you shouldn’t be doing this with some random guy who you think is named Todd or… maybe it was Tim.

Have your first time anal sex experience with someone you trust. That way, you won’t be uncomfortable communicating with him, and you won’t be blushing when you see your shit on his dick. Hey, it happens. [Read: Dating a girl who likes anal? 15 secret moves to impress girls who prefer the backdoor]

#13 Don’t do it unless you want to. Listen, if you’re still debating whether or not you want to try out anal sex, then maybe you should take it easy and not rush into it.

You have plenty of time to try it out, and you should never engage in a sexual act because you feel that you have to do it. If you really don’t feel comfortable with the idea of it, then tell your partner. If they aren’t understanding of that, then perhaps you should reconsider being with them as well.

[Read: The surprising but factually true benefits of having anal sex]

Now that you know how to have anal sex, let’s get this straight. It might not be for everyone, but if you’ve always wanted to try it, there’s no time like the present, right? Just remember to enjoy your first time anal sex experience with somebody you trust, and don’t feel the need to rush into everything all at once. Who knows, it may be your new favorite move.