Penetration: Do it Yourself

Sexual Wellness | | Natasha Weiss
5 min read

Hey all you savvy self pleasure-ers – this one is for you! You may have mastered the art of clitoral stimulation, and are well versed at getting yourself off. When it comes to self penetration, things get a little er…complicated. 

From slippery mishaps to accidental ouches, it can be difficult to figure out just how to properly penetrate yourself. We’re here to help, or at the very least, give some extra pointers as to how to do it yourself. 

Get The Right Equipment

First things first…pick your poison!

Sort of. Here’s where you decide what exactly you’ll be using for penetration. Picking the perfect dildo (note to editor: link to picking dildo article if published) for you may take some trial and error. But what a fun way to experiment – do it for science!

It seems like there are endless options in the world of dildos. From glass to crystal, ceramic, silicone, metal, and more – you may not know what works for you until you try it.

There are devices that do more of the work for you like dildo riding machines and sex tools. Penetrative vibrators are constantly evolving, with tricks like a come hither motion that target the G-spot, or attached clitoral stimulators. 

Keep in mind that heavier materials like glass and metal will take a little more work to get it in the right position, and may take more concentration overall. 

While you won’t be able to get as deep, fingers absolutely count as penetration, and they are totally free, as well as incredibly convenient. 

Warm Yourself Up

You may have run into some roadblocks if you try to rush into things, and go right for penetration…much like your high school boyfriend. 

Just like if you were having sex with another person, foreplay is important!

The complex structures of the female erogenous zones are made up of networks of erectile tissue. When given the time to allow arousal to build, the body responds. Your heart rate speeds up, cheeks flush, pupils dilate, you may start to get “wet”. Aka – you’re horny!

Preparing the body for penetration doesn’t necessarily sound sexy, but that’s just what it is.

Of course, you probably won’t be making out with yourself, but there are plenty of ways to tap into your sexual zone, and prepare yourself to get it on.

  • Dance in your room. Whip your hair around. Touch and rub yourself all over. Move your limbs, and get your energy flowing. This is especially fun in front of a mirror.
  • Take a bath or a hot shower. Hot is key here. Light a candle. Take your time to feel the water rushing over your body. 
  • Self-massage. Before you move downstairs, grab your favorite oils and practice some self-massage. Work from your face, to your neck, chest, breasts, stomach, thighs, feet, and back up. You may even enjoy massaging inside your mouth and on your inner and outer labia.
  • Watch ethical porn if that’s what you’re into! Homemade porn and sexting are also great options. 

Wild, Wild Wet

All that foreplay may have you feeling slippery down below. If not, no worries! Just call in for backup by reaching for your favorite lube

Whatever lube you choose is up to you, just be sure to check if it’s compatible with your dildo, or penetration object of choice. 

* Warning! Make sure to do a test patch on your inner wrist when trying a new lube. The last thing you want when you’re trying to self-pleasure is irritation and itching. 

Proper Positioning 

One of the more difficult parts of finding the best way to penetrate yourself is figuring out what position works best for you. You will need to finagle your arms and hands at the right angle, and align it with your vulva and vagina. This can also lead to hand cramping.

Take a break and stretch out those carpal tunnel muscles if need be. There’s no rush!

Start slow, we’re reminding you again the importance of foreplay. You very likely may enjoy clitoral stimulation before inserting anything inside your vagina. 

If there are certain positions that you enjoy when having sex with another person, you can work to replicate them by yourself. 

Doggy style, missionary, side-lying, standing up, squatting, and more are all possible when self penetrating. Another fun option is to place your dildo on your bed or steady surface, and ride it cowgirl style.

If one position doesn’t seem to be working, you can try it from the other side, switch hands, or go from the back versus the front. Long arms are helpful here.

Feel free to use props, pillows, straps, furniture, anything you need to support yourself while self pleasuring. Get creative!

Hot Tip: While it’s awesome to find something that you know will get you off, we encourage you to explore and experiment with yourself. You never know what you may discover! The goal isn’t orgasm, it’s simply pleasure and curiosity. 

Listen to Your Body

If you’ve tried and tried, and just can’t seem to enjoy self penetration (or any for that matter), that’s totally ok – not everyone does! Penetration is not the end all, be all of sex and masturbation. 

But if you happen to be experiencing pain during penetration, it could be indicative of a reproductive health disorder like a yeast infection, STI, or endometriosis.

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