Anal Fingering | The Ultimate Guide to Anal Pleasuring

When you hear the word fingering, you usually think about fingering your girl’s vagina right?

While fingering a girl’s pussy is already super pleasurable (if you know how to do it properly – there’s special ways to do it that most people have never seen), there’s actually a whole new world to be explored just a couple inches from the pussy.

Learning how to anally finger your girl properly can be one of the most rewarding things you embark on.

Most girls don’t experience anal fingering with most, if not any guy they sleep with, so by learning how to do this well you’ll definitely stand out.

Just take a look at some of these naughty WhatsApp chats to see the results of the stuff we teach:

 

Anyways, back to the topic – anal fingering provides super unique and satisfying sensations, along with being a great way to warm up for anal sex (which is honestly another topic in itself that we’ll have to get to sometime).

With anal fingering, you can actually give a girl anal orgasms (which we will mention later), as well as even stimulate her G-spot – this is because the anus and vagina are actually only separated by a thin membrane, which allows sensations from one hole to be felt in the other.

Anal fingering also stimulates a girl mentally and emotionally. It’s a HUGE turn-on for most girls as anything to do with anal/ass play is seen as “taboo” or “forbidden”.

The role of taboo and forbidden acts in a woman’s psyche is extremely underestimated, as women have a different attitude towards sex than men.

Once you can get a girl’s depraved side out, there’s really no turning back.

And anal fingering is one of the best ways to get a girl to explore her deep, hidden desires.

Just a word of warning: you’ll find that once you introduce this sort of thing (anal play) – she’ll start to expect it as a staple of your bedroom life!

It can actually get quite addictive for the girl as it’s such a strangely pleasurable feeling.

Now let’s get into how you should prepare for anal fingering properly, and then we’ll move onto some naughty techniques!

Preparation

Honestly if you’ve had experience fingering a girl in the pussy, you really shouldn’t have a problem learning how to finger her in the ass.

That being said, there are a few unique differences that you need to keep in mind when first doing this.

As with fingering her pussy, it’s always a good idea to keep your fingernails nice and trimmed so that she doesn’t experience any pain from accidental scratching.

(That’s honestly the last thing you want to happen while she’s enjoying herself.)

In addition, you’ll want to wash your hands thoroughly before getting in contact with the anal area, as you’ll be in contact with fecal bacteria.

Actually, it’s best practice for you and your partner to take a shower together first so that their are no funky smells or anything while you’re enjoying yourselves.

Now, with fingering her ass you MUST make sure you have some good lube available.

Unlike the vagina, the anus is NOT self-lubricating.

So, while you can get away with fingering and eating a girl’s pussy without lube (given you’ve turned her on enough so that she’s soaking wet), you can’t really expect to have a good time fingering her anus going in raw.

Most lubricants you find in stores will do the job. Water-based, silicone-based, and even natural oils such as grapeseed and olive oil are fine.

Just make sure you have some form of lubricant to use! If not, it can be rather painful.

You can check out this video for a more in-depth guide on how to choose the best lubricant for you:

Now there’s the mental component of preparation.

Many girls will not have had experience with anything anal related, so it’s important to understand and give her time to loosen up and relax.

Its crucial that she’s prepared for this experience.

It’s okay if she’s a bit uncomfortable at first but be sure to stop if at anytime she says it’s too painful for her.

(Also make sure she has agreed on you trying to finger her anally. It might seem like a turn on to try it on her out of the blue but trust us when we say it’s not a good idea!)

Take it slow, communicate well, and you’ll be sure to have a good experience.

Now we’ll proceed into some nice techniques.

Anal Fingering Techniques

The Lumberjack

This is more of a warm up move, as you’re not actually inserting any fingers into her yet, but nonetheless it’s a great way to get her used to some sensations around her anus.

Once you’ve applied some lube to your hands and on her ass cheeks, simply put your hands together like you’re praying, and rub them in between her cheeks with a sawing motion.

Be sure to start slowly and softly, and then later on as she’s more comfortable you can start increasing the speed and pressure that you apply.

You can also vary it to tease her as well.

This move will get her used to the sensation around that area and get her nicely warmed up for the more hardcore techniques later on.

Thumb Twiddling

Yes, you heard that right!

This strange sounding technique is actually quite simple.

Essentially, you want to place both hands like a fist between her ass cheeks and spread them apart with your knuckles.

Now, at this point your thumbs should be right above her anus. Slowly move them around in a circular motion, being sure to smoothly rub the outside of her anus.

Again, be sure to use plenty of lube. You can of course increase the speed and intensity as you go on and she’s more comfortable.

Initial Entrance

At this point your girl should be ready for the next level.

Lubricate a finger extremely well (we recommend starting with your pinky, but if you want to shock her a bit you can use your middle or index finger), and slowly insert it in.

There’s no need to insert it all the way in at first, just slowly move your way in and stop at points when she tells you to, or when you feel is necessary to get her used to the sensation.

You can tell her to release and contract her muscles down there accordingly, which will cause the sensations to vary as well due to the variation in pressure on your finger.

Once she’s gotten used to your finger inside, you can slowly start the usual fingering motion – moving in and out.

If you ever feel it’s getting a bit dry in there you should always add more lube.

Bend The Finger

Once your partner is comfortable with your finger up her ass you can try to bend your finger slightly towards her vagina.

Depending on whether or not she is facing you or away from you, you will either have to bend your finger towards, or away from yourself. It should be simple to figure out.

By bending your finger, you’re basically hitting the wall of the rectum.

This can be quite pleasurable as there’s really only a thin membrane separating the vagina from the anus, meaning that she’ll be able to feel some sensations there as well.

She’ll be feeling some unique sensations that she’s probably never felt before if she never tried ass play before.

As you bend and wiggle your finger around there more, you’ll be hearing her moans and even screams of pleasure.

Eventually she might even experience anal orgasms! This is because the same nerves that lead to vaginal orgasms are being stimulated as well.

However, not all women can experience anal orgasms (unlike squirting orgasms, which all women should be able to experience).

If your woman has never squirted, check out our newly updated course Squirting Triggers to learn exactly how.

It’s one of the most important things you can learn to do as a man, as well as something all women should experience on a regular basis.

Both you and her will be much happier and fulfilled in your relationship.

Stimulate the Perineum

What is the perineum?

It’s basically the area in between the vagina and anus, or in between the scrotum and anus for men.

It’s also known as the gooch in non-medical, everyday terms.

If you and your girl are super open-minded already she might already have given this area a nice licking while giving you a blowjob, and maybe you’ve done the same when eating her pussy.

This is a super sensitive spot that you can start massaging gently with while you’re still anally fingering your partner.

You can massage it in a similar fashion to how you massaged her anus, using your thumbs in a circular motion.

The combination of anal and perineum stimulation is so mind-blowingly pleasurable that there’s really no way to describe how good it feels.

You’ll just have to trust our word on this and try it on your girl soon and see the reaction on her face!

Two Holes Are Better Than One

Now it’s time to double penetrate your girl!

Don’t worry, it doesn’t involve another man (unless you’re into that sort of thing).

What we’re talking about is fingering both her pussy and ass at the same time.

As this can be quite overwhelming for the girl, we recommend doing this after she’s used to the anal fingering from the previous techniques we mentioned.

While you’re still fingering her ass, take your other hand and insert a finger into her vagina.

By this point, there’s no need to be so gentle on her pussy as she’s probably drenching wet from all the previous techniques earlier.

You can probably even start off with two fingers.

So, by now you’ve got two fingers in her pussy and one in her ass, fingering her at a moderate pace.

While you’re doing this your woman is probably moaning like crazy, experiencing new heights of pleasure she’s never felt before.

Double Up

Hold on, we’re not done yet – there’s yet another level to anal fingering.

This one might be a bit challenging due to physical limitations.

Bluntly speaking, we’re going to attempt to insert two fingers up the ass.

It’s going to take a lot of patience, and lube. A lot of lube.

Similar when you were first trying to insert your first finger up there, it’s going to feel quite tight and uncomfortable for the girl.

So be patient and don’t be discouraged if it takes a long time, or it comes to the point where she’s too uncomfortable to continue.

You can always try next time.

Anyways, when you’ve finally managed to get two fingers in, be really careful.

Slowly move them in and out and pay attention to your girl’s reaction.

You can then try bending your figure like we mentioned earlier to stimulate the walls of the rectum and vaginal membrane.

It can be too painful for some, and in that case one finger is likely adequate.

In the case your girl is a real deviant and really enjoys it, you can really explore with this and even try to insert more fingers.

However, if your girl is a non-professional (a.k.a a pornstar), it’s highly unlikely she can handle more than one or two fingers up there.

Nonetheless, one or two fingers already feels really good for most girls.

Add Your Tongue

Now we’re just going to go over this briefly, as we have a whole article dedicated to oral sex.

Basically, while you’re fingering her ass you can start eating her out as well.

Try licking, sucking, kissing, etc. All these techniques are explained in detail in our how to eat pussy article.

The combination of your tongue and finger in two different holes is likely to stimulate her in a really unique way that she’ll remember for quite awhile.

Later on, if you’re really adventurous you can also try eating her ass. We may even release an in-depth article on that sometime!

The Verdict on Anal Fingering

This is really one of those things that you have to try for yourself before deciding if it’s for you or not.

You might think it’s too freaky and out there for you to try, but once trying you actually get addicted!

So, don’t be afraid to try. Most girls have secret taboo kinks and fetishes you would’ve never imagined and are more open-minded than you thought.

Bringing up anal fingering and similar things to your girl, and then of course trying it can be a great way to improve your relationship.

The taboo and forbidden aspect of anal play, along with just how good it feels, is a great thing to add to your bedroom repertoire.

Once you start incorporating anal fingering and other types of anal play into your sex life, there’s no turning back.

If you have any questions about anal fingering or want to share your experiences with it, feel free to leave a comment below.

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