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 Inserting a prostate massager for the first time can be a little confusing. Which way should it go? How do you keep it inside? How do you clean things up easily?  

We’re going to answer all your pressing questions about how to insert a prostate massager for the first time. 

how to insert prostate massager

First step: Get to know your prostate massager 

Before you learn how to insert a prostate massager, let’s get acquainted with one first. 

1 The p-spotting curve: Prostate massagers have a curved shape to them for a good reason. They are designed to create constant pressure and stimulation on the prostate gland (the p-spot) which sits on the upper rectum wall toward the bladder. A curved massager hits the spot.

2 The bendy bottom part of the prostate massager has two functions: to keep the massager in place and to externally stimulate the prostate (aka the perineum).

3 The rimmer base of the massager sometimes has rimming stimulation. On our remote control prostate massager Wake, there are 360-degree rotating rimming beads that stimulate the anus while it’s fully inserted. 

Wake stimulates you in 3 simultaneous ways: via the prostate, anus, and perineum.  

Here’s how to insert a prostate massager correctly

We’ve broken down the process into easy bite-size steps to help ease you into inserting a prostate massager--the correct way.  

Don’t skip the lube step, and don’t insert a prostate massager too quickly or without a “warm-up”. Both missteps may cause injury. 

Step 0: Prep the bum, and the toy & gather clean-up aids

Prep the bum: For anal sex preparation, it’s not uncommon for folks to empty their bowels 1 to 2 hours before. This helps to ensure there will likely be no feces in the rectum. Some folks also choose to use an enema. These bum preparations are most often done when you are sharing the prostate massage experience with a partner. 

Prep the toy: Make sure both your bum and sex toy are clean before you begin. Even if your toy is brand new, wash it with a gentle cleanser. 

Prep the clean-up: The last prep step is to make sure you have the tools you need for a fast cleanup: towels, wet wipes, condoms for your toy, and/or gloves for finger play.  

Condoms are great for inserting a prostate massager as you can easily tidy the area by removing the condom after use and throwing it away. 

Step 1: Relax your bum muscles & find positioning 

Relaxing your sphincter is a big deal when inserting anything into the bum. If your sphincter, a ring-shaped muscle that encloses the rectum, is too tense you may not be able to reach your prostate very well. A tense sphincter may cause the toy to graze the prostate vs. pinpoint it

If your sphincter is persistently tense, you may consider anal training, a practice of training the sphincter muscles to relax.  

Finding the position where your bum is most relaxed is a must. This can be tricky and takes trial and error. 

For beginners, try inserting the toy while you are on your back, knees, or your side with one knee up toward your belly.

Step 2: Get aroused & warm up the area with a finger

Don’t go in cold. When you do insert a prostate massager you should be “warmed up” to anal stimulation, and sexually aroused. 

Begin by inserting a lubricated finger and allow your body to get used to this for a bit. Take things very slow here. You can manually stimulate the prostate here too if you want to get things started.

And definitely feel free to stoke the penis or stimulate the testicles too. Boost that arousal level before inserting a prostate massager. (Just don’t bring yourself to orgasm yet.)

Doing this helps those sphincter muscles relax so you can easily receive the massager, and it produces more pleasure. 

Step 3: Lube it up ( A MUST )

Rectums do not produce their own lubrication. You must bring that into the equation. Use a water-based, toy-safe, silicone-free lubricant on both the toy and your anus opening. 

Do NOT be shy with the lubricant. The less friction, the better you’ll feel. 

Consider a pump bottle lubricant like XOXO -- it's ready when you are. (One handed application seriously comes in handy!)

Step 4: Use the vibrator just at the anus opening 

This is optional but using the vibrator function of the massager just on the opening of your anus can help everything relax even more. As you use the vibrator you’ll find your sphincter becomes more and more relaxed. 

This is a great step for those who are new to anal play. 

Step 5: Gently and slowly insert with the curve facing your belly 

The prostate is inside the body and up toward the penis. 

So, ensure that the curve of the toy is facing the front of your body (not your back) and begin slowly, slowly, inserting the prostate massager. 

Listen to your body. If you experience pain–stop. 

Don’t move the prostate massager back and forth, but rather inch it upward into the rectum. The goal is putting constant pressure on the prostate.

Your body will speak to you– if you’re relaxed enough to receive the toy you won’t have major resistance and you’re free to go on in. 

If you sense tenseness, slowly ease the toy in and focus on relaxing the bum. 

Step 6: Turn on your remote control prostate massager and/or lift your rectum muscles 

If your prostate massager has a remote control (all the best ones do) use this to turn the vibration on. Start at the lowest setting for a while before exploring more. 

Once the massager is inserted fully, it may also be a good idea to “lift up” the anus muscle in a pulse-like motion. This may enhance stimulation.


3 tips for those who are new to anal play

In closing, here are 3 bonus tips for those looking to learn how to insert a prostate massager for the very first time. 

#1 Use your breath 

Similar to the idea of breath in yoga, pair any new movement (such as inserting the prostate massager or a finger) with an out-breath. Breathe in deep and slow, and when you breathe out, relax your body as you stimulate.

#2 Listen to your body & go slow

Your body will tell you its limits. Don’t try to go too fast when inserting a prostate massager. No one starts squatting 215 pounds at the gym on their first strength training session. They build up to that. 

If you do too much too fast you might hurt your body. 

Start slow, and build up stimulation. 

#3 Stimulate the penis & testicles too

While you are exploring prostate stimulation, don’t ignore other avenues of pleasure. Lightly stroke your penis or stimulate the testicles as you build arousal, and as you near prostate orgasm. 

It’s always a good idea to create familiar pleasure sensations while exploring something new. 




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