Anal Fingering | 8 Mind-Blowing Tips for Anal Pleasuring

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

While fingering a girl’s pussy is already pleasurable, there’s actually a whole new world to be explored just a couple of inches from the pussy.

Anal fingering provides super unique and satisfying sensations, along with being a great way to warm up for many different anal sex position.

With ass fingering, you can actually give a girl anal orgasms and even stimulate her G-spot.

What Makes Anal Fingering & Other Anal Acts So Appealing to Women?

Anal fingering 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.

What About Men?

Anal fingering isn’t just for the ladies. Men, too, can derive pleasure from anal play with their partner.

The techniques below can be used by both men and women on men or women. As long as there are two willing participants, you can use the techniques for hours and hours of fun.

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

Preparation

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 or injury.

In addition, you’ll want to wash your hands thoroughly before and after anal play.

Now, with fingering her ass you must make sure you have some of the best 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 if she’s turned on, 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 you don’t, it can be rather painful.

Now there’s the mental component of preparation. Anal is often seen as taboo and, for men, it can be seen as effeminate. It’s important to understand and give your partner time to loosen up and relax. It’s crucial they are prepared for this experience. It’s okay if they are a bit uncomfortable at first, but be sure to stop if at any time if it becomes too painful.

Now we’ll proceed with some nice techniques.

Ass Fingering Techniques

The Lumberjack

This is more of a warm-up move, as you’re not actually inserting any fingers into her yet. 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

This strange-sounding technique is actually quite simple.

You want to place both hands like a fist between her ass cheeks and spread them apart with your knuckles. 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 and slowly insert it into her anus.

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.

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.

Stimulate the Perineum

What is the perineum? It’s the area between the vagina and anus, or in between the scrotum and anus for men. It’s also known as the gooch or the taint in everyday terms.

This is a 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 adequate 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!

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 as 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 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 a while. Later on, if you’re really adventurous you can also try eating her ass.

From Anal Fingering to Anal Sex

Anal play is a good way to get your partner comfortable with anal sex, but it’s not always a direct connection between the two.

The fact is that anal sex is more intense than anal fingering. This may be something your partner is interested in, or they may be happy with the pleasure they get from fingering alone.

Just as the techniques above offered a slow, intentional introduction to anal fingering, you can follow the same path to anal sex. For some, this may be adding more fingers or introducing a small dildo into the anus. As your partner becomes more comfortable, you can increase the size of the dildo or even use the tip of your penis to gently penetrate.

Remember that anal sex doesn’t have to be the end goal. You and your partner may be happy with the pleasure derived from anal fingering alone and that’s perfectly alright.

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.

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