How to Stimulate Your Prostate - The Beginner's Guide

A Step-By-Step Guide To Massaging Your Prostate
Anal stimulation is great for everyone, no matter your sexual orientation or gender.  When that P-spot is stimulated the right way, it creates an amazing feeling.
So, maybe you've thought about anal stimulation and learning how to find your P-spot but you've got no idea where to start. Well, right here is where you start.

Prostate Massage

The prostate can be stimulated by various methods, often leading to heightened sexual pleasure for those with a prostate. This stimulation can be achieved by using fingers through activities such as manual prostate massage, or with the use of sex toys like prostate massagers & dildos. Pegging, where one partner uses a strap-on dildo to penetrate the other, is another popular method. These techniques can be performed by oneself or with a partner, offering a range of sensations and experiences.

The Basics of Prostate Milking

First things first, let's talk about what prostate milking actually is. The prostate is a small, walnut-sized gland located just below the bladder in men. It's responsible for producing the fluid that makes up semen. During prostate massage, the gland is stimulated either externally through the perineum (the area between the anus and scrotum) or internally through the rectum. This can be done using fingers, sex toys, or a partner's help.

Finding the Prostate Gland

To locate the prostate, gently insert a lubricated finger into the rectum about 2-3 inches deep. You'll feel a small, round bulb of tissue that's slightly firmer than the surrounding area. That's the prostate. It may take some practice to find it at first, but once you do, you'll be able to stimulate it more easily.

Techniques For Effective Prostate Massage

As for techniques, you can try gently massaging the prostate in a circular motion, or applying pressure and releasing it repeatedly.
Some men prefer a "come hither" motion with the finger. The key is to start slow and gentle, and gradually increase pressure and speed as feels good. Always use plenty of lube to avoid any discomfort.
    • External Prostate Stimulation: Using a wand vibrator, you can stimulate the prostate externally by pressing it against the perineum, the area between the scrotum and the anus. Apply gentle pressure and use circular or back-and-forth motions. The vibrations can transmit through the skin, reaching the prostate and providing pleasurable sensations.

    • Internal Prostate Stimulation: Internal prostate massage involves inserting a lubricated finger or a prostate massager into the rectum. Once inside, gently press and massage the prostate, a walnut-sized gland located about 2-3 inches in, towards the front of the body. Using slow, rhythmic movements can enhance the experience, leading to intense pleasure and potentially powerful orgasms.

The Best Positions For Milking Your Prostate:

There are a few different positions and techniques you can try for prostate massage.
  1. One popular position is lying on your back with your knees bent and feet flat on the bed or floor. This allows for easy access to the prostate.

  2. Another option is to get on all fours, which can make it easier to apply pressure to the prostate.

  3. You can also try standing up and bending over, or sitting on a chair with your legs spread.

5 Tips For Stimulating Your Prostate

1. Test Out The Waters

One way you may discover that you might like a little anal action is through an innocent act of rimming. Rimming is when your partner takes their tongue and licks your anal opening. This can be done in any number of ways and positions – but most commonly it is done in conjunction with a hand job.
For many, that first lick of their anal opening sends them instantly into an orgasmic bliss. If you've tried this already and that's why you're ready to learn more you can move on to the next step, but if you haven't tried anal rimming, it really is an amazing way to test the waters to see if you might be more into exploring more anal play than you thought.

2. Always Use Lube

Before I go on and list a few more ways to play, I need to touch on lube. Lubrication is so, so important when it comes to anything being inserted into the anus. Fingers, toys, strap-on, someone's penis - there has got to be lube on it. The reason for this is that the anus does not naturally lubricate, so without adding a lubricant there is a much higher chance of pain and even tearing.

Typically when it comes to anything anal, we suggest to use a silicone based lube. However, if you're using a silicone toy then you cannot use a silicone-based lube because it will actually break down the material and eventually ruin your toy. So, if that's the case then go for a nice water based lubricant like our TooTimid Water Based Lubricant.
Image of TooTimid silicone lube being poured in hands

3. Next, Try Some Finger Play

So, you've tried rimming and can confirm you're reading to try more. Next you can try putting one or two, nicely lubed, fingers inside your anus. This is a feeling that many people find extremely satisfying. You can either test this out on your own during masturbation or have your partner experiment for you.
Have a conversation and you can curiously ask your partner if they would be open to having a little finger play with you during a blowjob or hand job. (Remember to make them cut those fingernails first if they're long, just a random word of wisdom.) Anyway, so then you are receiving your blowjob and a lubed up finger slides into your rectum just a bit, hitting that prostate, eventually you'll experience an orgasm that probably feels like nothing you've quite yet felt before.
So, you have nerve endings in your rectum and you have the prostate. When the prostate is stimulated through anal play, it is very, very pleasurable. Relax and just enjoy. Pleasure is pleasure and you have now found something new that makes you feel good.

4. Now It's Time For Some Toys, Small Toys

Okay, you've received the rim job and you've felt how magical fingers can feel up there - what now? The next step would be to step it up to an anal toy. However, you do NOT want to dive right into some kind of large anal toy, oh no, you want to start with just a teeny, tiny toy. I know it probably feels lame starting super small, but trust me this is the smart thing to do. You basically need to train your anus if you want to work your way up to large toys. 
Linked below you will see the anal training kit that we would recommend you start with. This kit has 3 anal training plugs of different sizes. So, you can work through the sizes in this set then you can explore and start buying bigger toys. This set below is great for beginners because they are made of hypoallergenic silicone, they're waterproof (sometimes beginning anal in the shower is a good idea), they've got a suction cup base bottom and they are easy to use.

Recommended Training Kit: Silicone Anal Plug Kit
Hands holding blue anal training set of 3 butt plugs with suction cup bottoms

How To Use A Prostate Massager

Alright, so you've tried everything I wrote about above and you're ready to try a toy that's specifically created to hit your P-spot. Before you begin, it's best to start with some kind of foreplay or masturbation. You want to be really turned on rather than just going straight in. This is because when you are aroused your prostate actually physically starts to swell, which makes it much easier to find and much easier to stimulate.

Once you're ready, you're going to want to get into a comfortable position to insert the toy or have your partner insert the toy. So, you can be laying on your back with your legs in the air or you can bend over (pretty much like you're in doggy style) making sure you have something around you to lean on.

Next, go ahead and apply that anal lubricant I talked about earlier. Slowly and steadily insert the toy and to start, just begin with a gentle rubbing motion. For a little bit you're just going to play around and find what feels good for you. You can play with an up and down type motion going over your P-spot over and over again. Or, something that commonly feels good is putting more pressure specifically when the toy is on your P-spot. So push the toy a bit harder, or if it has vibrations, turn the vibrations higher to see what that feels like for you.

Just take your time and experiment. Eventually you will find your groove. And I do want to note that sometimes certain toys aren't right for us. So, if you aren't loving a toy then try a different type. Everyone's bodies are different and we all feel pleasure from different things, so be patient with yourself as you explore this area of your body.

Our 3 Best Prostate Stimulating Toys

Hands holding black prostate massager with remote control connected

The Dev's Prostate Stimulator is going to be a good toy to start with because it isn't too large. This toy has 10 different vibration functions that change pulsation and escalation functions which makes it really fun to play with. You can control those vibrations with the remote this toy comes from. 

Black silicone prostate stimulator with taint ticklers

Next, we've got the Kip's Prostate Stimulator. This one doesn't vibrate but it's make up for that with the ticklers it has built in. These ticklers are set up there to smoothly rub your taint to provide total pleasure. This is another toy that is the perfect size and shape you give you an amazing P-spot orgasm.

Prostate Massager

The Tala Vibrating Prostate Massager is for those of you who are more experienced with anal play. It is a little bit thicker and features a firm shaft. This toy has powerful vibrations and a wide base for worry-free play! The curves along the shaft will provide constant stimulation for you and your p-spot.

Have Your Tried Anal Stimulation? Let Us Know Anonymously Below!


  • Jim

    OK I have bought prostate toys vibrators
    my friend girl has bought them for me I can’t seem to know what I’m doing I wish i could rent a man to show me how to do it to me with his penis, that’s what I really wanna know how to do it is it Harder to do it with a penis I have penis shaped realistic vibrators I prefer The kind that you can sit on it so I can be hands-free I just want to be able to give myself a prostate orgasm or let somebody give me im doggy style on the bed and they’re standing on the floor i got to do that for 30 seconds and I thought it was wonderful I would like to lay on my back I just can’t seem to have an a vibrator in me and have an orgasm unless I pull it out If I edge which I’m a giver of greatness to im getting better at keeping it in Throughout my orgasm

  • Don

    One night my girl started rubbing around my hole. I never thought Id like something like this… But just her getting close drove me to a crazy orgasm. The next time she actually rubbed my butthole and I had another amazing orgasm. We then talked more about it and decided to get lube and experiment… It was amazing. We worked our way up to a very large dildo and I can take it all the way inside me with lots of lube… the key is to relax and just enjoy it. With anal play these are the most amazing orgasms Ive had my entire life. I never thought I would be into it… Seems like a gay man thing. My girl assured me its normal and shes a female its okay and we been playing with my anus ever since… Its incredible

  • Fun4her +me

    I’m more into Prostate Stimulation when it comes Anal Sex! My current wife or my ex-wife doesn’t care and did not care about having or giving Anal Sex and definitely no fingers anywhere near the Anus! I have heard and learned about PROSTATE Stimulation, and men cumming more quickly and harder when their Prostate is touched or massaged during Intercourse or Oral sex! In my collection of Sex Toys, I have a Waterproof Rechargeable Inflatable Multi-function Vibrating Prostate Massager ( not sold by TooTimid unfortunately) that can give me the best most powerful orgasms I ever had, and without cumming! You have heard of women having body shaking Earth shattering orgasms, this Anal Vibrator/Prostate Massager can do just that! Once I get the right comfortable inflation along with best vibrations, I have hips raise off the bed mind blowing powerful orgasms and without cumming! My wife has also giving me these same powerful orgasms, when we have had intercourse for a long time, of course she asked why didn’t you cum – I can’t explain other than I had a great powerful orgasm. (I’m not a minute man) Now that I suffer from E.D., I purchased from TooTimid a Hollow Strap-on ( I have reviewed) to get our sex life going, and she said it was too big! Since the Vagina can stretch much easier than the Anus, I experimented and found that I can penetrate my Anus with this Strap-on, and take it all the way in with a lot of lube and relaxation! I’m thinking of now letting her peg me with it, to prove that if I can take it in my tight little butt hole, she should be able to fit it into her Vagina to have some kind of sex for both of us to have fun!

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