Oiled Fingering

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Oiled Fingering
In today’s simultaneously sexual and sex-shaming culture, it can be hard to find clear, accurate information about sex and sex acts—particularly sex acts you do with yourself, like masturbating and fingering yourself! In this guide, we’ll provide clear, no-nonsense information on how to finger yourself. We’ll go over what it is, how to do it, and answer all the common fingering questions.
Note: this article is primarily aimed at those with vaginas/vulvas, although there is a section on anal fingering at the end of this article that of course applies to everyone. We acknowledge that not everyone who has a vagina/vulva identifies as a woman, so we have made an effort, where possible, to describe via genitals (i.e. “people with vulvas”) as opposed to gender (i.e. “woman”).
The term “fingering yourself” doesn’t necessarily mean the same thing to everyone. When most people say “fingering yourself,” they are referring to penetrating the vagina with one or more fingers. This is what we will discuss in this guide.
However, some people use “fingering yourself” to mean any vulva/vagina masturbation that uses the hands/fingers. For more on this kind of fingering, see our complete guide to masturbation .
You might wonder why people would want to finger themselves. There are several main reasons why you might want to do this (and/or know more about it)!
A big reason why someone might finger themselves is for pleasure! Some people like the feeling of fullness in their vagina while they stimulate the clitoris during masturbation. The outer third of the vagina is full of sensitive nerve endings, and you’ll be touching this when you finger yourself.
The vagina also has the G-spot, a spongy area of tissue on the front of the vaginal wall that is very sensitive when stimulated. We will discuss how to find and stimulate the G-spot in the next section.
The bottom line is that a major reason people finger themselves is because it feels good! (Of course, not everyone enjoys fingering themselves, and you shouldn’t feel like there’s something wrong with you if you don’t enjoy it).
Another main reason why people might want to try fingering themselves is to get to know their bodies better. If you’ve never tried to penetrate your vagina before, you might wonder what it’s like. What does it feel like? Where’s the G-spot? What angle is it at? Lots of us don’t necessarily get up close and personal with our vaginas very often, and it is very natural to want to know more about what is going on in there!
Some people also finger themselves to prepare for penetrative sex. You may simply want to be prepared or have an idea of what it will feel like. You might also hope that by stretching out your hymen in advance , sex will be more comfortable. If this is your aim, be sure to check out our FAQs at the end, as we have a whole series of questions on the hymen, “breaking” the hymen, and virginity.
Before we get down to business, I’ll give a quick anatomy lesson of the main things that are going on in your vulva.
Many people use the term “vagina” to refer to female genitalia. Actually, the vagina is only the internal canal! Vulva is the correct term for the external genitalia. This consists of the labia majora (the fleshy outer lips), the labia minora (the thinner inner lips), the clitoris (the sensitive bud of tissue at the apex of the labia minora), the vulvar vestibule (all of the tissue in between the labia minora), the urethra, the entrance to the vagina, and the hymen.
See this diagram for some guidance. Don’t worry about memorizing all of this – it’s just for reference!
Now that you are armed with the necessary anatomical knowledge, how should you actually go about fingering yourself? Read on for my five-step fingering formula.
First, you’re going to want to make sure that your nails are trimmed and your hands are clean. Vaginas are tender so you don’t want to scrape yourself up!
It’s important that you feel comfortable, ready, and aroused before attempting penetration. To that end, you’ll want to make sure that you have sufficient privacy and time. You might also want to do something specifically to relax and get ready. This could be anything from taking a bubble bath to listening to some calming music or reading something sexy. You might want to put on some lingerie that makes you feel hot or light some candles if you really want to create an atmosphere (although always be careful with fire!)
When you feel like you’re ready (and excited!) to get down to business, move on to the next step.
Penetrating yourself (with a finger or anything else!) is much easier (and much more enjoyable) when you are fully aroused. During arousal, the vagina becomes lubricated and the inner ⅔ of the vaginal canal expand. This makes the vagina slicker and more accommodating of penetration.
So, if you’re going to finger yourself, engage in some external clitoral stimulation first! You might enjoy stroking, circling, or tapping the clitoris. Think of it as foreplay with yourself.
It’s up to you if you would like to reach orgasm before you penetrate yourself. One advantage to reaching orgasm is that the vagina releases extra lubrication, so penetration will be easier. But it’s not necessary.
Especially if this is your first time fingering yourself, I highly recommend using some extra lube. Be sure to test any lube in advance by placing a little on the inside of your wrist and waiting 15 minutes. If there’s any itching or redness, don’t use it. If you can’t or don’t want to buy a dedicated lube, you can also try aloe vera gel (make sure it’s mostly aloe vera and doesn’t have too many other ingredients), coconut oil (if you aren’t prone to yeast infections) or sweet almond oil.
To lube up, take a small bead of lube and completely rub it around the fingers you will use to penetrate.
When you’re ready to introduce your finger, slowly reach down and begin to insert. Some body positions are better for this than others; generally you will need to have your legs spread for best access to your vagina, and you’ll need to be in a position where you are able to reach far down enough to send your fingers back up inside of you. You can experiment, but reclining on the edge of a chair or bed or standing with one foot on a chair are options that work for many people.
When you start to insert, move slowly. If you’re feeling discomfort, try to adjust your angle. The vagina is pointed towards your back, oriented about 30 degrees back from straight-up-and down. Continuing to move slowly, gradually insert your finger, adjusting as necessary. Don’t force it; if you start to feel uncomfortable, stop pushing in and either give yourself a moment to readjust and relax or adjust your angle. You may also want to add more lube.
Start with one finger. Many people use their index or middle finger, but if you find that your index or middle finger feels too wide or uncomfortable, you have a couple options: if your hand and wrist are flexible enough, you can try out your pinky finger. If this makes maneuvering too awkward, you can also use a very slim, clean, plastic or silicone object with no sharp edges. I recommend a slim plastic tampon applicator, but you can use anything that won’t abrade or tear your tissues with sharp edges or leave behind chemicals or residues not meant for your vagina (so be very careful with, say, a lipstick tube). There’s more on using objects in the FAQ, so if you’re going to go this route, be sure to check that out.
Over time, as you get more relaxed and comfortable with penetration, you may want to use thicker or even multiple fingers, but it is best to start small and gradually work up to it.
The G-spot is a spongy piece of tissue on the front wall of the vagina (so, towards your belly button and your bladder). It’s not especially deep inside the vaginal canal—about 2 inches on average. If you insert an index finger, you should be able to feel the sponginess. To stimulate the G-spot, curl your index finger like you’re making a beckoning motion.
Because the G-spot abuts the bladder, stimulating it may make you feel like you have to pee in addition to feeling pleasurable. This is very normal and nothing to worry about. Note that stimulating the G-spot manually might be somewhat difficult if you aren’t using your index finger. But try whatever works for you!
That’s it! Try these steps in order and explore a bit. If it feels good, great! You’re probably on the right track.
Keep reading for more common questions.
Now that we’ve covered the basics of how to finger yourself, let’s answer all of your remaining fingering-related questions.
Yes, you are! To explain a bit further, we need to consider why people think that they might not be virgins after they finger themselves. It mostly has to do with the hymen.
What is the hymen, you might ask? Well, the hymen is a thin membrane of tissue that partially covers the vaginal opening. It’s a common myth that the hymen needs to be “broken” for you to be able to fit a penis (or a dildo, or anything) in your vagina, and/or that once the hymen is “broken,” you aren’t a virgin anymore. Neither of these things are true.
First, the hymen doesn’t generally “break.” In many people, it will stretch with penetration. If you have a particularly thick or prominent hymen, your hymen may tear a little. Either way, the hymen isn’t “breaking.” You aren’t puncturing the seal on a cup of yogurt.
Stretched hymens can actually sometimes return to their un-stretched state, and tears in the hymen have been known to heal. Hymens also stretch, tear, or erode from totally non-sexual activities, like playing sports and using tampons. Additionally, not everyone has the same shape (or size) hymen; some are irregular and naturally have tags or notches. Some people are even born without one!
Thus, the entire idea that the state of your hymen has anything to do with your virginity is actually pretty ludicrous. In people with vaginas, the current shape/appearance of the hymen absolutely does not serve as any indicator of penetrative sexual experience (or even of any kind of penetrative experience, like using a tampon).
Generally speaking, virginity is commonly defined as “never having had sex with another person.” Even if you finger yourself and tear your hymen, you won’t be commonly considered to have lost your virginity.
I can’t define exactly what losing your virginity means for you, but I can tell you that your hymen does not equal your virginity, and fingering yourself does not make your virginity evaporate.
Before I answer this, let’s provide some context. There’s a prevalent cultural idea that when you lose your virginity, you supposedly “break” your hymen, which supposedly causes pain and bleeding. So you might think that any first-time penetration, including fingering yourself, is just naturally going to be painful and/or bloody and is something that you want to just get over with.
We have already discussed the fact that the hymen doesn’t really break—it stretches, or it might tear. Is this painful? Not usually. The stretching can be uncomfortable, or you may feel a slight stinging, burning, or tearing sensation. But hymen stretching and/or tearing is generally not going to cause stabbing pain or agony.
In terms of bleeding, there’s a slight chance that if the hymen does tear, it could bleed a very small amount. But it probably won’t—there’s typically not a whole lot of blood flow to the hymen.
So is everyone who says they bled or sex hurt the first time just lying? No, not at all—bleeding and pain are somewhat common experiences at initial penetrative sex. But most bleeding and pain at first penetrative sex have nothing to do with the hymen. The pain generally comes from either from a) a lack of lubrication, b) the tightening of the vagina due to nervousness, or c) a combination of both. This can lead to the tearing of the vaginal walls, which causes the pain and bleeding.
Given that first-time penetrative sex can be a pretty nerve-wracking experience even if you are genuinely excited and happy, it is not incredibly surprising that you might be dry or tight (two common sexual consequences of anxiety) when you want to first do the deed. The keys to working around this in a partnered penetrative situation are lots of foreplay, lots of lube (make sure it’s condom-compatible), and going very, very slowly so your body has a chance to adjust to the penetration gradually.
So how does this all relate back to fingering yourself? Well, the same principles apply to fingering yourself as apply to partnered penetration. Of course, a finger is considerably slimmer than the average penis, but to ensure the most pleasant, pleasurable, and easy experience, you should make sure you’re very aroused, use lube, and proceed very slowly. If you’re feeling pain, try more external stimulation and/or more lube. The nice thing about self-penetration is that you have total control over every aspect of the situation!
If you want to stretch out your hymen to make you feel more prepared and comfortable for penetrative sex, here’s how:
First, don’t do this too far in advance unless you are planning on engaging in regular self-penetration. If the hymen goes a long time without being penetrated, it will usually return to its non-stretched state, and need to be stretched out again.
When you are fingering yourself per the five-step plan above, when you’re penetrating, push down (towards the anus) for a few minutes to stretch the tissues. You can gradually work up to two fingers and then perhaps a dildo over time. Just take your time, be gentle, and don’t push too aggressively through pain or discomfort! The key to the most comfortable hymen stretching experience possible is lots of lubrication (store-bought lube will definitely come in handy here), being really relaxed, and introducing deeper and thicker penetration very slowly and gradually.
A couple of things could be happening here. If it’s actively uncomfortable, you may not be aroused, relaxed, and/or lubricated enough. Try to orgasm first from external penetration or at least put some lube on your finger before attempting penetration. You could also start with a smaller finger (like your pinky) and work up to a larger digit.
You might also be pushing in at the wrong angle, which can cause discomfort. (The vagina is angled towards your back). Try changing the angle slightly and trying again.
You should also check your nails—if you have any sharp edges, they can catch on the tender insides of the vaginal walls and cause pain.
Whatever you do, if it’s very painful, don’t just keep going; you can always take a break and try again later. But you shouldn’t just push through the pain; those are delicate parts down there.
A lot of pain—especially if you feel like you can’t get your finger inside at all—could be a sign of vaginismus. This is a condition where a woman feels pain with all penetration. If you are concerned about this, go to the doctor—it is treatable.
You also might not be feeling any discomfort, but just feeling “meh.” Maybe you looked for the G-spot but you can’t find it, or you just generally think it feels fine but not especially pleasurable. This is pretty normal— most women can’t orgasm from penetration alone , but also require clitoral stimulation. Don’t feel like there’s anything wrong with you if just penetration isn’t terribly exciting for you.
Yes, you can . This may feel less awkward than using your finger or allow you new sensations and positions. However, here are three essential guidelines to follow to safely penetrate yourself with objects:
Anything you might use on your genitals again should be stored in a clean, dry place. Some people use vibrating toothbrushes as genital vibrators. If you can’t buy a dedicated vibrator, this is fine (although I don’t advise stimulating yourself with the bristle end!) but don’t use it as your regular toothbrush, and store it separately. Also, don’t share toys with other people, and don’t use the same toy to penetrate your vagina and your anus.
Yes, you can. The anus is extremely sensitive and full of nerve endings, so stimulating it can feel pleasurable. Men also have the prostate, which can be stimulated digitally through the anus.
Unlike the vagina, the anus does not lubricate itself and is a fairly tight ring of muscle that’s generally closed, so if you want to do this, use lots of gentle lubricant and start with the smallest finger possible (so, the pinky) before working up.
Most people use “fingering yourself” to refer to self-penetration, although a smaller number of people use it to refer to any manual masturbation of the vulva/vagina.
So why do people self-penetrate? In general, there are three main reasons:
If you want to know how to finger yourself, follow this five-step plan:
Many common fingering questions center on misconceptions about the hymen, the membrane that partially covers the vaginal opening. The hymen generally stretches or sometimes tears; it doesn’t break, and your hymen is really not at all related to your state of virginity. Also, a feeling of stretching, fullness, or a slight tight discomfort with initial penetration are all totally common phenomena; while stabbing pain is generally an indication that your body is not quite ready yet—try more external stimulation and some lube.
The bottom line is that getting to know your body should be enjoyable, and fingering can be a great self-exploration tool in your arsenal!

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"If you’re just randomly bending your finger inside her vagina, she’s more likely to murder you than to actually orgasm."
Whether it's part of foreplay or the main event, fingering can be super pleasurable for people with vulvas—as long as it's done well. Bad digital stimulation isn't just a huge turn-off; it can also be incredibly painful! That's why we spoke with some sex-positive women about how men can up their fingering game.
Now, there's one big caveat here, which is that every woman and every vulva is unique, and there's no one-size-fits-all method when it comes to fingering. Ultimately, the best fingering technique is asking your partner what feels good to them! Still, our sources said there are a few universal pointers that could help all guys get better with their hands.
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