4 Steps to Give Women Orgasmic Anal Sex

Used to be that when girls asked me for it, my erection would disappear and I’d lose all interest in sex of any sort after that. I mean, gross. And in any event, her pussy’s right there; why would I want to stick it in her butt?

As I got older, I became less of a stick in the mud and decided to give anal more of a chance. Eventually, I discovered that, done right, women absolutely loved it, and soon I enjoyed it a fair bit too.

The fear for her, that comes with accepting you into the wrong hole... the thrill she feels at doing something taboo... and the pure pleasure that comes with an opening packed to the brim with nerve endings swallowing up your manhood into it, its sanctity at the mercy of it... all these things contribute to the emotional and physical excitement of it for her.

And, if you’re executing anal sex technically correct, with an aim towards supplying anal orgasms, your member will be hitting her vagina from the other side, a truly intense and orgasmic experience.

As a man, there’s the sense that you’re dominating this woman in a way you’re not ‘supposed’ to do, and the sense that she is yielding her body to you in a way she hasn’t to too many (or perhaps any) other men. These things enhance the experience for her as well.

However, this article isn’t here to discuss the merits of anal sex (though I will cover that briefly towards the end) – I’m not here to ‘convert’ anybody.

If you’re reading this, I assume you’d like to know how to do it well, and not that you are recoiling at how gross it is (like I, well, used to).

So... let’s talk about giving her thunderous orgasms, through her back door.

DISCLAIMER: I did really try to find some non-NC17 images for communicating the ‘position’ part to you below, but found it next to impossible to locate any images showing the position I wanted to show at all, let alone any PG-13 ones. So, there are a couple of NSFW images near the end of this post – you have been forewarned. Don’t read at the cubicle, or on the bench in the park by the local kindergarten.

 

The 4 Steps to Orgasms from Anal Sex

Unless you have a girl who’s an anal sex pro (and you will meet some girls like this – if a girl can find men who are good at it, it’s arguably more intense and enjoyable for them than vaginal... some women become downright addicted to penis in the pooper), anal’s going to require a bit more foresight and planning than vaginal.

With vaginal sex, all you need to do is get her naked and wet enough to enter, and you’re good to go.

However, with anal sex, you have a part of the body that does not produce natural lubrication, is not designed for (or used to) intense back-and-forth friction, and is controlled by a sphincter that can open quite wide, yet as a protective measure does not and cannot unless and until she is extremely relaxed and ready for it.

Additionally, the way many men try to perform anal sex – doggystyle, except with penis in butt instead of penis in vagina – is not well suited to providing orgasms, nor a maximally pleasurable experience.

So before we can make her orgasm from anal, there are four (4) things we need to take care of first:

1. We must prepare her mind emotionally for anal sex
2. We must prepare her body physically for anal sex
3. We need to make sure she’s well-lubricated
4. We need to assume the right position to make her cum

Let’s discuss each of these steps, and then we’ll discuss some of the emotional after effects on women of engaging in anal sex – and why it’s actually good for making a lasting, positive impression on them, and taking intimacy in your relationship with them to a higher level.

 

Anal Sex, Step #1: Emotional Groundwork

If you’re dealing with a girl who’s never received anal sex before, or her experiences have all been disappointing (most women’s anal sex experiences are like this: some guy she’s seeing begs and begs her to let him put it in her butt... she at last agrees... he ejaculates about 2.3 seconds after inserting his penis head into her rectum. End experience), chances are she’s ambivalent about anal, or even actively opposed.

There are a few ways you can go about remedying this:

• Watch some porn with her where a girl’s taking it in the butt and cumming hard, to get her curious about what, exactly, this girl in the porn is loving so much that she herself is missing out on

• Discuss some of your own past sexual escapades with her (assuming you’re at least a bit experienced with anal) and how your partners loved it and why the previous men these women had been with hadn’t been able to please them the same way

• Fantasize with her during sex about it, particularly as she’s enjoying it / close to orgasm: “Just imagine if my cock was in your ass and not your pussy. How bad that would be. How naughty it would be. How you couldn’t tell anyone, because they would all judge you. How it would have to be our little secret, and no one else could ever know my rock-hard rod was back there, pulsing and throbbing in your dark little no-hole.” Done when she’s really enjoying herself, you anchor the positive feelings of sexual pleasure to the idea of naughty, secretive anal sex, which is going to make her start to get curious about this, and want it

My personal favorite way to prep her for it and get her thinking about it and wanting it though is this: put her in doggystyle and mount her from behind during vaginal sex, then as you give it to her, scoop up some lubrication from her pussy and begin to tease around her anus with one of your fingers. As you get further into the sex and her pleasure is heightening, begin to plunge your finger in and out of her anus every so lightly, just teasing her at this point. The idea is to give her a taste of your finger entering her anus, but not to satiate that taste; you want her to want your finger in there desperately, but to make her wait.

Then, once she’s sufficiently hungry for more anal stimulation, you begin to plunge your thumb or forefinger (I prefer thumb for this... it’s just easier to manager when you’re giving it to her from behind. Plus, the girth is more like a penis’s) into her, deeper and deeper, until eventually your entire finger or thumb is inside her anus as you shag her from the back with your member. (note: careful to trim and file your fingernail before doing this, as your erection will be pushing up against her rectum from the other side and it’ll be pretty tight for the finger you have inside her; you want to avoid cutting up the delicate tissue inside with a ragged old man fingernail)

Here’s the goal: to get her to associate nothing but good emotions with anal sex.

These include, but are not limited to:

• Curiosity (”I wonder if it’s as good as it sounds?”)
• Pleasure (”It feels so good when his finger is in me; I really enjoy it”)
• Lust (”I want to experience more of him than just his finger in there”)

The more of these emotions you can instill in her, the more mentally prepared she’ll become for anal, and the easier a time you’ll have getting her to assent to having you inside that one part of her body you’re not supposed to visit.

 

Anal Sex, Step #2: Physical Preparation

The next step is her level of physical preparation, and that’s really down to just one element: how relaxed her sphincter is.

A sphincter is an o-shaped ring of muscle that expands or contracts to allow a mass to pass. The human body has sphincters throughout its bodily system in, for instance, the iris of the eye, expanding to make the pupil larger and let in more light, or constricting to make the pupil smaller and allow in less, or the throat to let food pass. The sphincter we’re concerned with in this case is her external anal sphincter.

If you’ve tried to enter a girl anally when she isn’t relaxed enough, you’ve experienced this first hand: it’s almost impossible to get her anus wide enough to even get your penis head in. Yet, a fully expanded anus can be wide enough for you to stick your fist into (I’m not going to link anything here, but if you’re curious / don’t believe it, just head to your favorite image search engine, type in ‘anal fisting’, and hit ‘go’. Prepare your eyes). So what gives?

Turns out that taking a penis in the butt is the same as pushing poop out of the butt: it’s damn near impossible to do when someone isn’t feeling sufficiently relaxed. The anal sphincter, like a sad little puppy with a puckered-up mug, needs comfort.

To get her comfortable enough to relax muscle control over her sphincter and, essentially, unlock the gate for you to plumb her inner depths, you have several techniques at your disposal:

• Spend a good while playing with her anus with your fingers, inserting first one, then widening the opening to insert a second, and so on and so forth, until you’re able to comfortably fit three or four fingers inside

• Stimulate her anus in other ways – some guys like sex toys for this, some guys like using their mouths (assuming she’s cleaned up properly down there beforehand)... doesn’t matter; the point is giving her enough pleasure on the outside that she wants you on the inside

• The one I find works best personally is bringing her to orgasm or close to orgasm through penetrative vaginal sex. Then stopping, switching, and putting it into her butt. If you’ve done a good job with vaginal, you usually won’t have much prepping to do before she’s ready for a penis in her anus – sometimes, none at all

There’s another consideration here, too, and that’s whether she’s properly prepared herself as well.

That means she’s cleaned herself out as well as possible and made sure she isn’t going to make a potty run mid-act. Although, no matter how clean she gets herself, you’re typically going to be pulling your member out with a little brownish liquid, at least – so, if you’re squeamish, this is the stop you probably want to get off this train to anal orgasm land at.

 

Anal Sex, Step #3: Make Sure She’s Lubricated

Goes without saying, right?

Let’s say it anyway, though. The anus does not produce natural lubrication. At least, not enough to handle the kind of friction that comes with sexual intercourse.

If you’re swapping from vaginal penetration to anal penetration, you’ll take some lubrication with you (that’s still on your cock from vaginal sex), but you should still add more.

My personal favorite lubrication is Divine No. 9, which doubles as massage oil and also contains carrageenan, which helps prevent skin-transmitted STDs. I’ll use Vaseline too, though not if using a condom – Vaseline will chew away at most condoms on the market.

The best method for making sure there’s enough lubrication is:

1. Generously lubricate the outside of her anus, then insert several generously-lubricated fingers into her anus while “warming her up”

2. Before sliding yourself into her, make sure you are generously lubricated as well

If you hit both those points, there will generally be ample lubrication, though if you remove your penis at any time, you may want to drip some more lubrication on before diving back in.

Several more notes:

• A note on hygiene: once any part of your anatomy has touched her anus, don’t let that part come into contact with her vagina until it’s been thoroughly washed. Finger or penis. The anus is home to a greater collection of bacterial fauna than the vagina is, and some of these can cause yeast infections or urinary tract infections if they spread to that part of her body, neither of which you want her getting, for both of your sakes.

• A note on safety: STDs are transferred more easily via anal sex than vaginal sex, because of the damage that often occurs to the anus/rectum (mostly, tissue tearing – we’ll talk about this in a minute). That means you’ll pass infections more easily to her, and she’ll pass them more easily to you. So, if you don’t know her well (recent hookup) and/or the two of you haven’t been tested regularly, use a rubber, or one of you may be leaving with a ‘souvenir’ you hadn’t anticipated. Some of the more common diseases you’re at risk for picking up from a woman you’re having anal sex with are herpes and one or more of the 100+ strains of HPV (genital warts, anal lesions, etc.).

• And a note on bleeding: women who are inexperienced with anal have thinner membranes inside their anuses, generally, that have yet to be toughened up through lots of lovin’ to that part of the body. Even if you’re fairly gentle and use lots of lubrication, she may still have some bleeding after anal sex, and may bleed a little when she passes solids for the next few days. So long as it isn’t a lot of bleeding, she’s fine. If you have anal sex with her often enough, her body will adapt, toughen up the membranes there, and she’ll bleed less and less, and eventually not at all. Just make sure to give her a few days off after an anal sex session in which she’s bled a bit. (if you see any serious bleeding, get her checked out at a doctor’s office, and make sure she’s honest with Doc about the cause)

• Can you do it WITHOUT lubrication? Well... sure, yeah, you can. Should you? I know a few folks who have girlfriends they’ve been having anal sex with for a long enough time that they can go lube-free and it’s fine. As I understand it, this is helped along either from the girl getting so wet (vaginally) that it drips back towards the anus and gets swept in during the thrusting, or the man producing lots of precum (when going in bareback). The risks of this of course are tears in anal tissue, which can become infected with fecal matter (big problem for her, and probably no anal for you for the next half a year while she recovers), and friction that can even rip the skin of your penis, or the condom if you’re using one. Why would you want to do this? Some women like (a sprinkling of masochism while submitting to a dominant male is rather common in many women when they’re being honest) the added pain that comes from no lubrication... but again, don’t do this (if you’re going to do this at all) until she’s quite experienced and the skin inside her anus has toughened up a fair bit, or you may be looking at some potentially damaging medical issues.

 

Anal Sex, Step #4: The Position

Prep out of the way, let’s talk position.

Most guys doing anal treat it like traditional doggystyle / sex-from-behind, except instead of their penises being inside her vagina, their penises are inside her anus.

It’s much more difficult to make her orgasm this way.

There is, however, an easy way to make her cum during anal sex.

Here’s how you do it:

1. Make her lie on her side. Left side or right side, doesn’t matter.

2. Have her draw her knees up to her chest, or chin. Tell her to pull them all the way up.

3. Kneel down on your knees, and insert your penis into her rump. You want to basically be the Y-axis to her X-axis; instead of being lined up with her, like the man normally is during most sex positions, you want to be perpendicular to her.

I’ve included two images below that are the closest I could find to this (knees could be drawn up a bit farther, and the choking going on in the first image isn’t a standard part of this and I wouldn’t recommend that unless you and she both really know what you’re doing – autoerotic asphyxiation and all that). Apologies for the indecency, but considering the subject matter, well... heck.

Here they are:

Then, just bang her until she cums her brains out. Pretty straightforward.

IF you’re having trouble with ejaculating too quickly – a pretty common issue for a lot of men with anal sex – check out this article for prevention:

• 5 Sex Pro Tips to Last Longer in Bed

... and this one for dealing with the fallout in the event of a mishap:

• How to Manage Premature Ejaculation So She Still Thinks You’re a Man

Do note that with anal, the most common point for a man to cum prematurely is just as he’s inserting the head of his penis into her anus – one your full manhood is all the way inside her, you’re past the most ‘high risk’ point for ejaculating too soon.

 

Why Should I Do Anal Sex? What’s the Benefit?

If you’re the pleasure-seeking type, you’re probably already a big fan and in need of no convincing by me.

If you’re not as much of a novelty seeker and/or come from more of a conservative background like I did (and you still made it through this article somehow anyway), you may be wondering, “What’s the point?”

So let’s discuss some of the benefits of anal sex for your relationships with women.

Anal sex generally has the following effects:

• A woman you perform anal on typically feels like she has submitted to you in a major way with anal – more so than she does with vaginal (especially if you made it all the way up in her and lasted longer than a couple of seconds)

• If you gave it to her well, and provided her an anal orgasm (or two... or three... or more), she leaves feeling like you have total mastery over her body. Even many women who are experienced with anal haven’t had an anal orgasm before, and these orgasms, when delivered properly, tend to be among the most powerful a woman will ever experience

• Because you have participated in a taboo together, she will generally feel significantly closer to you – you’ve done something together you should not have done. You made her do this, or drew this out of her... and she can’t tell anyone about this. This feeling is strongest obviously among more conservative and less sexually experienced women (not as big a deal if she’s going to tell her three best girlfriends over Sunday brunch that, so, she did anal with this new guy last night, and he was even better at it than Travis)

• Anal sex is a terrific way of communicating to her that you are a dirty man; further, it makes it abundantly clear to her that you don’t have her on a pedestal as a pretty princess whom you could never despoil like that, and knowing she’s firmly off your pedestal makes for healthier relationships all around. Anal isn’t the only way to show her you don’t have her on a pedestal, but it’s one of the big ones – it’s a pretty loud and clear message

• Anal sex is an early relationship differentiator, in that if none of her other boyfriends penetrated her anally and you do, it communicates you are more sexually experienced and more sexually daring than her priors were. Conversely, if previous boyfriends have given it to her anally and you shy away from this, sooner or later when she gets to fantasizing about anal, it will not be your penis she is imagining inside her, and you won’t be the one she’s thinking of when she says, “Hmm, I wonder what he’s up to these days?”; generally better to give it to her this way, and give it to her better than her priors, so it’s your face and your member popping into her head when she thinks “good anal sex”

• It makes you a better lover, better able to please her in more different ways, and able to add more variety in the bedroom and keep things from getting stale as quickly

I think the biggest thing to stress about anal sex is it is an act of domination and submission more extreme than vaginal sex. As a result, a woman will typically feel you have ‘owned’ her body more firmly after you have engaged in anal with her.

Expect to see more ladylike behavior, more submission, and perhaps a little ‘ashamed but excited and intimately connected to you’ behavior for a couple of days after an anal sex session, too.

 

Does Anal Sex Make You Gay?

I think this is one of the fears some guys have: if you can get off putting your cock into a woman’s behind, what’s to stop you from wanting to just swap in a guy and have some good ol’ fashioned homosexual buttsex instead?

Anal sex is without a doubt a different beast than vaginal sex. It’s not about impregnation. And it’s not as much a man-woman thing as vaginal is either. Instead, it’s more about dominance and submission. One dominant penetrating partner shoving his cock into one receptive, submissive partner. And the receptive partner could be anything – woman, man, sheep, elephant, you name it.

However, I’ll tell you, personally, it hasn’t made me remotely bicurious. I don’t look at a guy’s ass now and say, “Boy, I’d sure like to split that like a melon.” Doesn’t happen.

Although honestly, I don’t think that about women either. Even if a girl has a great ass, it’s her ladybits I’m fantasizing about, not her exit hatch. If I penetrate her anally later, it’s either going to be a spur-of-the-moment thing, or if I take her as a girlfriend it’ll be something one of us proposes at some point (or, sometimes then too, spur-of-the-moment).

At least so far as I can tell, you either like dudes and would like to shag them, or you don’t, and enjoying plunging your member deep into the anus of a pretty girl doesn’t seem to impact that, any more than it makes you suddenly want to anally dominate fat girls or Farmer McMurphy’s fuzzy sheep with the big doe eyes.

 

Anal Sex: Parting (Money) Shot

Let’s wrap up with a quick summary, since this one is a little longer.

To give her a great anal sex session and help her reach an anal orgasm, we have four (4) steps we want to follow:

1. We must prepare her mind emotionally for anal sex
2. We must prepare her body physically for anal sex
3. We need to make sure she’s well-lubricated
4. We need to assume the right position to make her cum

To pull off #1, the emotional groundwork, you can:

• Watch orgasmic anal porn with her
• Talk about previous good anal sex you’ve had
• Seed/fantasize about anal sex with her during vaginal, near orgasm
• Play with her anus during vaginal sex, eventually sticking a finger in

To pull off #2, the physical preparation, to relax her sphincter, you can:

• Play with her anus with fingers to warm her up
• Stimulate her anus with your mouth, toys, anything else
• Make her cum from vaginal sex, then switch to anal

To pull off #3, make sure you:

1. Lubricate the outside and inside of her anus with your fingers
2. Lubricate your penis before you stick it into her

To pull off #4 and assume a position you can make her cum anally from:

1. Make her lie on her side
2. Have her draw her knees up to her chest, or her chin
3. Kneel down on your knees, and insert penis into anus

Benefits of anal sex (besides the pleasure/novelty element) include:

• She feels as though she’s deeply and personally submitted to you
• Great anal makes her feel like you have ownership of her body
• Because of the ‘jointly violated a taboo’ element, you become closer
• You show her you’re dirty, naughty, and don’t have her on a pedestal
• You differentiate yourself from prior lovers, or supplant their memories
• It makes you a better lover with a more diverse set of bedroom tools

And if it makes you gay, well, I sure haven’t found that out yet.

If you haven’t given anal sex a whirl yet and you’re curious to try it out, here’s your guide.

And if you’re an old pro at plundering booty, I hope you found a tip or two in here that’ll help you do it a little more smoothly, or a little more orgasmically.

Yours,
Chase Amante

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