How To Finger Someone – A Guide For Guys & Gals

How To Finger Someone – A Guide For Guys & Gals

Fingerplay often gets rushed over or wholly overlooked during most pillow dates. It’s seen as a way to get someone lubed up so things can rush to penetration. Or, to give someone an orgasm so the other person can jump to their own pleasure.

But fingering can be a mind-blowing event all on its own.

That’s why we’ve made this in-depth guide on how to finger someone in the safest and most pleasurable ways – so you can both benefit in ways you might not even realize. Let’s dive in!


There’s no bigger turn-off than grubby fingers trying to slither their way into the vagina or anus. And yes, I know some people are thinking it’s crazy to think that dirty fingers in the butt don’t matter. But they really do.

The first thing anyone should do is make sure they have clean hands – properly cleaned ones! Not quickly rinsed under water. Next nails should be trimmed short and filed smooth.

This last part is really non-negotiable – and yes, for guys too. It doesn’t matter how prissy you might think it is to have neat and trim nails because for fingering, it’s vital.

Long nails (and even short ones that are crudely cut with sharp edges and no filing) can cut the inner wall of the vagina. The flesh there is quite delicate – even micro tears can happen. This leads to easier infections and even the possible contraction of STIs. Not to mention, it’s going to be uncomfortable for your partner. The same goes for guys. The anal cavity is also delicate; if you go in with bare fingers, the same thing can happen.

Now, the best thing for anal play is to put a condom over your fingers (or actual latex finger sleeves that are made for this sort of thing). However, if you keep the long, jagged nails, you might still break through the latex and bad things could happen. See where I’m going with this?

So keep those digits clean!

But also, the other side should wash too, especially if it’s been a sweaty day.


Both sides should be 100% honest about any diseases they have, so the other side can make an informed decision.  Also, you can take appropriate safety measures. Because things like gonorrhea, chlamydia, or HPV (for example) can still be contracted if the fingering person touches themselves after.

If you’re sexually active, make sure to have regular tests. And use appropriate contraceptives, etc.


There’s this idea attacked to sexual potency that any person worth their sexual salt should be able to make someone dripping wet all on their own. And the idea of needing lube can actually irk some people.

Well, I’m here to say that’s nonsense.

There are so many reasons why someone can’t get really wet, or even a little, no matter how horny you get them. It can be a side effect of medication, health issues, general stress problems, age, or just their body’s personal settings, etc. Plus, there’s the fact that the bum hole can’t generate lube at all.

Get yourself a bottle of water-based lubeand add a respectable amount even if you’re not to internal play yet. It will make all the difference in the world.


Vaginas come in many different shapes, colors, and scents – and the smell of flowers is not one of them. As long as it’s not rotten or heavily fishy, it’s fine (because that could mean an infection).

The same goes for penises. Some are cut, some not. Some guys like their balls touched some don’t. But no matter what, there’s a lot more to each area than just the “sweet spots” we’re usually focused on.

Play around with the surrounding areas during your pre-fingering episodes. There are a ton of nerve endings to be found.


It’s important not to quickly shove your fingers into the vagina. But it’s even more important for the anus. The muscles there are very tight and pushing anything in too fast and hard can hurt like hell.

No matter the hole, start with one finger and slowly (with lube) work your way in at your partner’s pace. And when (or if) they’re ready, add another finger. But always go back to being slow any time you add a new digit.


This part is pretty much going to make or break the “success” of how to finger someone.

Make sure to listen not only to the sounds of pleasure (or discomfort) they’re making but if they’re maybe a bit quiet or not great at communicating what they need, make sure to gently ask them what is working or what isn’t.

Do they want slower? Back down to one finger? For you to withdraw entirely and go back to external play?  Perhaps they need a different angle or to change positions.

Communication is always key.


When our partner is in the throes of ecstasy, it can be tempting to switch what we are doing to find something that will be even more pleasurable.

However, that is the last thing you should do. If you find something your partner likes, stick with it. They might want it faster or harder, etc. (let them tell you). But don’t change from two-finger g-spot massaging to clit tickling mixed with finger thrusting when the previous method was already driving them wild.

Getting to amazing orgasms comes when you find what works and stay with it until they come to that exquisite peak.

If you’re not sure, there are things other than just stroking to mimic thrusting. There’s tapping, pressure, circular motions, “swiping” back and forth, etc.


  • Even if there’s no penetration, exclusive external play still counts as fingering
  • Be patient, gentle, and supportive during someone’s first anal experience. It’s usually very stressful because it can be scary.
  • Bum play has nothing to do with being gay. Straight guys, you’re missing out on some amazing pleasure. You have the exact same nerve endings. Give it a try!
  • Try taking your index finger and middle finger and then crossing them. While inside, you can twist them around for a unique sensation.
  • If your fingers get tired, you can totally use a sex toy for help while you recover for round two. There are even FINGERING TOYS that can lend a hand.
  • Not everyone likes direct clit contact. Some like it above or below.
  • Try playing with the perineum area. So yummy.
  • Don’t use porn as a guide. It’s generally not accurate.
  • Know when to stop? When you’re partner says so. It’s that simple.
  • Add other sexy elements like kissing, licking, earlobe nibbling, etc.
  • You can totally do it over the clothes if that’s what your partner needs/wants.
  • Keeping eye contact can be intimate as hell.
  • When it’s done, and if there’s another pillow date in the future, ask them what worked, if they’re okay, etc. Show you care.


The biggest takeaways from this article would be to stay clean, go slow, explore, and communicate. So, the next time things are heating up in the bedroom (or wherever) why not dedicate an entire session to just finger stuff? You might have some amazing discoveries ahead of you!      

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