How to Finger Your Man: The Ultimate Guide on an Ancient Art

One little finger in the right place can bring a big smile to your man’s face. And maybe make his toes curl and back arch. 

It’s no secret that the booty is full of pleasure points. A man’s ass is a powerful erogenous zone with thousands of nerve endings. With so many ultra-sensitive spots to explore, it’s worth mastering your stroke and learning how to finger your guy. 

We’ll dive into the fine art of fingering with tips, tricks, and techniques to hit all the right spots. From prepping your nails to finding the perfect rhythm, consider this your ultimate guide to becoming a fingering connoisseur.

How to finger someone: 10 tips

Good sex starts with preparation — and fingering is no different. Here are some tips to set the tone and make sure you and your partner have a good time:

Trim your nails

We all like a little “come hither” action. But long nails with points or jagged edges can quickly turn pleasure into pain — and not the fun kind. Before getting up in there, trim your nails.

Short, smooth nails prevent discomfort and reduce the risk of cuts during penetration. Plus, it signals to your partner that you care about their comfort, a great way to help them relax and feel safe. 

Wash your hands 

Good hygiene is never out of fashion. Before getting started, thoroughly wash your hands with soap and warm water and clean under your fingernails.

This isn’t just about cleanliness; it’s about ensuring you’re protecting your partner from harmful bacteria that might be on your hands. A little hand cream to soften the touch doesn’t hurt, either. 

Douche before the deed

A glistening derriere requires proper douching. For men that bottom, douching is a normal part of prep for a potential hookup or night out. Even so, it never hurts to ask your partner to douche before sex.

Proper douching ensures you’re both clean and comfortable, safeguarding you from messy surprises that might inhibit the action. If your partner is new to douching, share our douching guide with him. 

Prepare your space

Dim lights, candles, and the right playlist can heighten the mood and help your partner climax. It’s also a great idea to prepare ahead with lube and other sex supplies, clean your sex toys, and ensure your bed is fresh and inviting.

Preparation is more than just aesthetics. A well-prepared space sets the tone for sex, allowing you to concentrate on each other’s orgasms without any distractions. 

Communication is the key to climax

Great sex isn’t like what you see in porn. It’s better. Even if you’re the one doing the fingering, it’s a two-way street. Talk with your partner about what gets them aroused, their favorite ways to be fingered, and what helps them orgasm. Encourage them to be vocal. Not only will it help you hit the right spots and find the proper motion, but hearing them ask for more of this or that will rile you up. 

A is for arousal

Although passionate, quick sex can be a lot of fun, don't let porn fool you. It’s never a bad idea to warm up your partner with foreplay. Plus, if you or your partner deal with sexual performance anxiety, easing in is an excellent way to get comfortable.

A sensual massage, teasing their penis, or lots of touching in the shower helps you connect and build sexual tension that leads to earth-shattering orgasms. Likewise, talking about your kinks, sex toys, and other preferences can be as educational as it is exciting. 

Stimulate the prostate 

The prostate (aka the male G-spot) is located between the anus and the base of the penis facing the belly. That means if your partner is on their back, your palm should face upward. Hitting this spot during penetrative intercourse can make your partner cum, but rubbing or stroking it with your finger is an equally effective way to bring your partner to orgasm.

Remember our tip about foreplay? Piquing your partner's arousal will send blood rushing to the prostate, making it swell and become extra sensitive to manual stimulation. Pay attention to how his prostate swells against your finger, and you’ll have that boy-pussy squirting in no time. 

Try different stimulation techniques

The way you like to be fingered isn’t necessarily how your partner likes to be fingered. Likewise, the fingering technique that worked last time may need some adjustment this time.

Variety in technique is the secret ingredient to a good orgasm. Try different motions — circles, taps, come hithers. Play around with the pressure and speed. Use lube generously to make your moves smoother and more pleasurable.

Remember, even if you’re focusing on fingering, you can supplement with other techniques. Blowing your partner, massaging their perineum, or sucking on their balls will send them over the moon. 

Take it easy

Slow and steady wins the race — and makes your man cum. Avoid that horny high school finger-banging.

Start gently and pay attention to your partner’s responses. Massage their butthole with your fingertip, caress their thighs and cheeks, and enter slowly and gently. Let your partner pull you in, gradually deepening your thrusts and speeding up your tempo. The slow approach will help you rub your partner the right way and build anticipation that intensifies their experience. 

Know their anatomy

A good top studies their source material. Your partner’s anus is as beautiful as it is sensitive. The high concentration of nerve endings means even a light touch can be highly stimulating. Play around with pressure, speed, and motion, and pay attention to what elicits the best response. 

It's okay to ask for help. Finding the prostate isn't like clitoral stimulation; it’s easy to spot that little nub on the vulva, even if straight men can't seem to find it. Without visual feedback, you’ll have to ask your partner if your finger is hitting the right spots. The experience will be more pleasurable, even if you need a little direction.  

How to finger yourself: Upgrade your masturbation game

Masturbating with your penis probably came pretty naturally. Exploring your anus might not feel so intuitive. It may take a little more trial and error, so here’s a step-by-step guide to finger yourself:

1. Get comfortable. It might sound obvious, but finding the right position is step one to reaching the right crevices. If you’re new to this, you can start by lying flat on your back on your bed and bending your knees so they point upwards. This position gives easy access to your index or middle finger and allows you to relax your body. 
2. Use lubricant. Generously apply lube to your finger. Start by massaging your anus with your fingertip, slowly pushing inward. Your anus will be tight initially. Lube and slow rubbing will help you open up and enjoy yourself.
3. Begin with foreplay. Foreplay isn’t just for sex with a partner. Massage your perineum, run your fingertips up and down your body, and play with your penis. This gentle approach puts the focus on your pleasure, helps your muscles relax, and builds up your arousal. 
4. Control your breathing. Finding the ideal position can be challenging and a little uncomfortable at first. Deep breathing helps you relax, letting you meditate your way to an orgasm. 
5. Find your prostate. Once your finger is about two inches inside, angle it upward. You should feel a round bulb — that’s your prostate!
6. Find the motion of the ocean. Using a classic “come hither” motion, stimulate your prostate. If you feel like you have to pee, that’s totally normal! Your prostate is located just below the bladder. Find the rhythm, angle, and speed that makes you gasp for air. 
7. Masturbate for deeper pleasure. Not everyone achieves prostate orgasms from fingering alone. Stroking your penis while you play with your prostate can lead to a mind-blowing climax. 

For some people, a dildo or vibrator is more effective for prostate stimulation. After all, many of them are explicitly designed to give you anal pleasure. Plus, a sex toy may be more comfortable to reach the right spots, simulate deep and hard thrusting, or let your hands rest while the vibrations work their magic.