How to Have Anal Sex - A Start-to-End Complete Guide

Written by Chelsea on March 5, 2016

Anal sex, what guy doesn't want to try this?

You have gotten familiar with good old traditional sex, which is great and all, but now you're ready to conquer new ground and storm novel territory.

Plus, a woman's ass is one of the sexiest parts of her body.

Though many girls can be reluctant to let you fuck her in the butt, if you go into the situation well informed, and it's done right, it will be a great experience for both parties.

an atheltic woman with toned buttocks

How to Convince Your Woman to Do Anal

If you want to try anal but find that the woman is skeptical, you could try a few things to open her mind to this wonderful, adventurous, and pleasurable experience.

While you're having sex the typical way, you could try touching her anus a bit and see how she responds.

Don't just leap into this way too soon without any forethought though.

When she's on top, grab her ass, then start inching your finger toward her opening.

Pay attention to her reactions, and if she seems to like it, keep going, maybe even progressing to getting your fingertip inside.

If she likes this, she will probably like anal sex, even if she is reluctant about the idea initially.

Some girls think, on principal, that they wouldn't like their butt played with, but I can assure you that for many of them, this will be most enjoyable.

In fact, some women have a much easier time cumming during anal attention, due to the extra stimulation of the deep spot which can be hard to reach during normal intercourse.

A lot of girls think that it makes them a whore if they enjoy, or even partake in, ass play.

For some reason, there's a stereotype about this.

They may also think it's simply gross, and buy into the stigma that it's something only women with no self respect engage in.

You could try casually bringing up studies you've read on the subject that could clear up any misconceptions or stereotypes she has about the topic, such as data from this article.

Be informative and try to open her mind to it, but don't come off as desperate.

That's unattractive and gets you nowhere. Nobody likes someone who nags at them.

If you start slowly involving her other hole in your sex play, and she responds favorably, it could be just a matter of time before her mind is completely open to this world.

One notably pornography actor, Manuel Ferrara, is known for getting the girls off on orgasms before even whipping his penis out, with his technique of fingering the girl's butt.


So let's assume that you've received the go-ahead to put it in her ass.

First of all, congratulations. You're about to level up as a man.

Before you proceed though, there are some things you should know about the art of anal sex.

This is very different than traditional pussy fucking, and there is some important information to be aware of about it before you embark upon this wondrous journey.

a nice butt without panties on

Anal sex is best done sober. Everyone knows that drunk sex can be really fun.

You lose your inhibitions and go wild on each other, and get a bit rougher than you might typically get.

This is not the best course of action with anal sex.

Alcohol lowers your control over your body, and this is a delicate art; something that requires fine motor skills.

While a glass or two of wine could help to get relaxed and in the mood for some back door loving, you don't want to take it too far.

If you're drunk for the activity, you may be tempted to go balls to the wall, like a battering ram at the castle gates. I strongly advise against this approach.

Be sober, and keep your wits about you.

Warming her up is a must.

Warm up first. The female needs to be very relaxed for what's about to go down.

There are some things you can do to ensure this is the case.

Taking a hot shower before any action is a good idea for both relaxation purposes and hygiene.

In addition to this, you can calm her down using a full body massage, with emphasis on the ass.

an erotic massage given to a female

You could engage in some foreplay to get her excited, make out, and play with her pussy before taking things to the next step.

This prepares her mind and body, and gets her into the necessary zone.

You could have vaginal sex to warm up as well.

Just because putting it in the ass is the main attraction doesn't mean you shouldn't start with something a bit more familiar first.

Plus the more aroused she is, the easier it will be.

Prepare her ass with your fingers.

You don't want to immediately jump to the part where you stick your dick inside.

Start by gently rubbing her hole, encouraging her to relax if she seems tense.

If you're not afraid, it's a good idea to use your tongue for this as well.

If the girl you're with is open to letting you stick it in her ass, it's safe to assume she'll appreciate your tongue there as well.

If you haven't done this before, you should try it, you may like it.

And if you're afraid to lick a girl's ass, I'd have to wonder why you'd want to fuck it then.

Anal is about experimenting, just like she's trying something for you, you try something for her.

If this is her first time, she's likely very nervous, so reminding her to take deep breaths will do both of you a favor.

How to do finger insertion

Once she's relaxed and aroused, use your finger to put some light pressure on the opening of her ass.

You don't want to push too hard at first, let it slide in on its own, one knuckle at a time.

Pay attention to her breathing, and try to coordinate the insertion with her exhalation.

Once your finger is all the way in, don't move it for a while.

While she is getting used to this sensation, stimulate the rest of her body with your other hand.

You can massage her more, rub her clit, or kiss her. Once again, if you notice that she is tense, try to calm her down by talking to her, and encouraging her to relax.

Use a lot of lube.

Water based ones are best.

water-based lube to be used in anal sex

Unlike the pussy, the rectum does not lubricate itself.

This may seem obvious, but it's so important that I need to say it. I cannot stress this enough, USE LUBE.

A little bit is not enough, you need to use a lot.

If you think you've put enough on there, put even more.

This activity should not hurt, and that makes this ingredient extremely necessary.

Coconut oil also works quite well, smells nice, tastes nice, and is antibacterial.

coconut oil to be used in anal sex

The warming up and the lube are both non-optional when it comes to anal sex.

They are what makes this type of sex enjoyable in the first place. Without them, it wouldn't be fun for either one of you.

an oil change to emphasize lubrication during anal sex

Take it slow.

When the time comes to finally get down to the action, you'll be very excited and ready to go.

I know what you're thinking, you just want to shove it in there already.

Now this is understandable, but I have to disappoint you, good gentleman. You can't rush it.

Gentleness is the name of the game in this situation. You already have your finger up her ass. Is she tense?

If so, there's still a lot of work to be done.

You cannot stick your dick in until she is completely calm and un-clenched.

You may need to sweet talk her a bit more, remind her to calm down, massage her body a bit more, play with her pussy, or kiss her.

a girls sexy butt preparing herself

How to Begin Insertion of Your Penis

Once her level of calm is achieved, you can work on getting inside her.

Put the head of your (very lubricated) cock against her (very lubricated) opening.

Pay attention to her breathing, and start easing your way in as she exhales.

The head is the largest section of the penis, obviously, so that might be the most difficult part.

Don't shove your entire dick inside her at once.

Put the head in first, and work the rest in at a very slow pace. Once the head is in, the rest goes easier.

You don't need to put a lot of force behind this motion. Let it slide in naturally, and when it's all the way, allow it to stay in for a bit without moving, allowing her to get accustomed to the feeling.

You could also tell her to push to make this smoother.

Again, encouraging her to relax her muscles is of utmost importance.

Sweet talk her a bit, make her feel like a lady.

If she's clenching up, it's not going to be easy on her, and she might need a bit of encouragement or reminding to stop tensing up.

a man and woman talking in bed

Sex positions and Anal Sex

If this is her first time, a good position to start with is missionary, because it provides clitoral stimulation, and also offers the woman some level of control as far as pace and motion.

Another idea for first timers is having her on top, so she can lower herself down onto you.

After getting a bit more familiar with this activity, you can progress to different positions.

If you're partaking in this with a more experienced woman who already knows she loves it up the rear, you can get a bit more adventurous with methods.

Don't forget About Her Vagina

Don't neglect the pussy.

It can be easy to get caught up in the tightness surrounding your cock, but don't get overtaken by these sensations and forget the other parts of the girl's body.

As you're easing slowly in and out, massage her body with your hands and pay attention to her clit.

Most girls will also appreciate some kissing to keep them calm and relaxed.

Many girls can get off this way, having double or even triple orgasms.

a beautiful woman having an orgasm

After you've started out very slow and gotten to a steady pace, you might find that she wants to go faster.

If she's a first-timer, allow her to decide this.

If it is in fact her first time, she probably won't be begging to get pumped up the ass like a porn star, but once she relaxes and melts into the activity, she might like it a bit faster, and perhaps you can gradually progress to some rougher stuff.

When you start getting close to the edge, it might be a good idea to ask permission before you give her bums a cream filling.

If you're lucky, she'll love this idea and encourage you to do so.

Anal Sex Safety and Other Important Tips

Some other tips.

This probably goes without saying, but I've gotta say it anyway; don't put your penis back into her vagina after you've had it in her ass.

That's an infection waiting to happen.

When you're done, don't just abruptly pull it out the same way you would with vaginal sex, ease it out very slowly.

If you like this activity, and want to do more of it, it's a good idea to make it as enjoyable for the woman as possible, so some after-action cuddling is recommended.

With this information, you're on your way to becoming an anal sex pro.

Hopefully these tips will lead you to have a most enjoyable experience that you can repeat time and time again.

Happy ass f*cking!

The PhalloGauge Team will answer all questions/comments you may have.

Feel free to leave a comment as an anonymous guest!

The comments section is moderated for spam.