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How Do I Get More Comfortable Masturbating?

Dear Shy Masturbator, 

First of all, can I tell you how cool it is that you’re taking steps to work through this? Masturbation is absolutely a form of self-care, but for many (probably most) of us, the message we received as kids was that masturbation was dirty, shameful, or embarrassing. Great news: it’s not! 

I’m thinking there’s a psychological component to your question, but I’m also going to talk you through some sensory steps to help make masturbation as fun as possible. Lastly, I want to thank you for asking this! I’m sure there are a lot of people who experience this discomfort and are embarrassed (in the opposite direction) that they can’t seem to “do” solo sex. For you and anyone else out there experiencing this, I want to assure you that it’s a totally normal step in the pleasure process.

So here are six ways to make masturbation more comfortable, more pleasurable, and way sexier:


Sex Toys Y-2, Ring Clamp Stimulator

1. Normalize solo sex.

Before you crawl under the sheets / into the shower / etc., I’m going to first recommend that you surround yourself with positive examples of masturbation. Why? So that your mind can dispense with any “ew” around masturbation, and start replacing it with a “HELL YES.”

If you’re not already listening to the Sex With Emily podcast, try signing up for that and other sex education shows that openly discuss solo sex. We regularly talk about overcoming masturbation blocks! You can also hack your Instagram, and follow sex positive accounts that take masturbation out of the shadows and into everyday discourse. Next, check out my friend Justin Lehmiller’s fantastic site, sexandpsychology.com, for research-based thoughts on solo sex and, well, every other type of sex.

I find that many vulva owners were never given a real education around masturbation, so it can be a confusing world to enter. Conversely, many penis owners were more or less expected to masturbate from puberty on, but there was often a sense of ickiness associated with it. By bringing positive examples into your life, you can start evolving your neural pathways, creating new (hot) associations with the act itself.

2. Hack your cycle. 

Vulva owners have a monthly cycle that makes arousal more or less obvious. Take ovulation: you know that glorious window of one or two days mid-cycle, when you want sex so badly you get turned on by a blade of grass? That is an ideal time for masturbation. Your hormones are ready and willing to help you achieve orgasm, thanks to a surge of estrogen and testosterone. By week three, that feeling wanes, and then right before your period, it’s back, thanks to increased blood circulation in your genitals.

Penis owners, believe it or not, also have a hormonal cycle – but it’s daily, rather than monthly. Testosterone is highest for these individuals early in the morning and wanes throughout the day. But, it can also rise fairly readily, after watching porn for example. This brings me to…

G-spot Rabbit Flapping Vibrator

3. Turn YOURSELF on.

Before masturbating, try activities that get your endorphins flowing. That could include exercise (the guys at MindPump have some great thoughts on this), a dance party for one, or even having a stimulating conversation with someone. Getting “turned on” isn’t always directly sexual – it’s simply heightening your body’s excitement, encouraging feel-good chemicals to flood your system.

But turn on’s definitely can be sexual. Try experimenting with audio porn apps, erotica, or ethical porn, such as the vast archives on Bellesa Plus (aka the Netflix of Porn) to see what stuff stimulates you. Bellesa Plus is fantastic because there’s an emphasis on story and legitimate chemistry between performers – so the pleasure you’re viewing is authentic. We’ve got these cool things in our brains called mirror neurons, which help us learn and internalize specific behaviors. And when we watch ethical porn, we process the pleasure we’re seeing and learn how to make it our own. (Wink wink.)

4. Eliminate distractions.

One of the biggest mental blocks with masturbation is worrying you’ll get “caught.” So if you can, choose a time and place to masturbate where you’re gloriously alone, and not preoccupied with the thought that someone might walk in. There’s lots of research to suggest that noises you make while masturbating help bring about orgasm, so don’t be afraid to breathe heavy, sigh or moan as sensations arise: Pamela Madsen, founder of Back to the Body, talks all about this in our recent convo.

You can also take it a step further, by making your solo sex environment actually sexy: light a candle, put on music you love, rub delicious-smelling oils all over your thighs, chest, neck. What we’re doing here is soothing your senses, and helping you get into your body by eliminating mental chatter. The more engaged your senses are, the easier it is for the body to respond without inhibition.

Strapless Strap on Dildo Vibrator 5 Inch

5. Try different sextoys.

Whether you’ve got a vulva or a penis, there’s a pleasure toy out there with your name on it. Let’s talk options:

  • Vibratorsare the most popular option for vulva owners, and varieties abound. I’m a particular fan of Dame’s Pom, which is a flexible vibrator that’s also waterproof…so you can take it into the bath or shower. But I love that you can “personalize” the Pom to your anatomy, since it’s pliable.
  • Air-suction sex toys are getting more “buzz” (har har) these days, and are just the ticket for many vulva owners who don’t readily orgasm with vibrators. They’re designed to mimic oral sex, stimulating both the nerves in the clitoris and nearby nerves for some serious OMG feels.
  • Penis rings, aka cock rings, are getting more sophisticated, and my favorites fit on the shaft of the penis, with a vibrator that stimulates your perineum. If you’ve never experienced thatvibe before…now’s your chance: We-Vibe’s new Bond toy is a great stimulating toy that delivers powerful sensations. You can even control with a remote, making “the tease” all the more exciting.
  • Masturbation sleevesallow for penis insertion and a ton of sensory options: vibration, suction, grooves, and ridges. When it comes to physical stimulation on the penis itself, sleeves are fantastic and, thankfully, abundant. Why not try a few, and become a sex toy connoisseur?

Experiment with different areas of your body.


My final thought here is to avoid going straight for the genitals during your next masturbation sesh, and instead, let the anticipation build up all over your body. Run a hand over your chest, tease your inner thighs, squeeze your nipples…regard yourself as a lover, someone whose body deserves pleasure, and is ripe to receive it.

In that vein, you can also try exploring some booty action. If this is new to you (but piques your curiosity), here are some excellent anal play tips, and here is the go-to anal training kit from b-Vibe that I recommend to everyone. It’s adorable, comprehensive, and sets you up for anal orgasms. Yup, they’re real! But anal isn’t a zero to sixty game, which is why the b-Vibe kit is so smart: it teaches you how to prepare your sphincter, and gives you beginner-friendly, vibrating butt plugs. (Bonus? It’s on sale right now.)

There are so many health benefits to masturbation, from better sleep, to better mood, to better partnered sex—so once again, I applaud you for writing in and asking this question. When we reframe masturbation by regarding it as one of many self-care activities, we can start to explore it more deeply. Kudos for pleasuring the #1 lover in your life (you), and have fun on the journey!

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