A Beginner’s Guide To Masturbating: The Hows, Whats & Wheres

I was a late bloomer when it came to exploring my body, only masturbating for the first time at the age of 24. Since then, I’ve more than made up for missed opportunities, shifting my mindset to view masturbation not as a shameful secret but as a basic need in many people’s lives. But as I embarked on my journey of self-pleasure discovery, I struggled to find resources that could point me in the right direction. (Surprisingly, there is no wikiHow for getting off.) Eventually, I ploughed ahead on my own, spending hours exploring my body to find out what did and didn’t feel fantastic. Toys, my hands and shower heads provided different sensations but building the confidence to start experimenting with self-pleasure took quite a bit of time. Knowing where to begin doesn’t come naturally to all of us.

So where can you go for some introductory intel? There is porn, of course, although this comes with a long list of issues, including often unrealistic, hugely exaggerated portrayals of nonconsensual — even violent — sex. Or you can ask your friends, as I did (provided you're prepared for a potentially awkward conversation). Fortunately, if neither option appeals, there are experts out there. If you don't have one on speed dial, allow me to share a few pointers from self-pleasure expert Samantha Marshall, head of pleasure, content and community at sex toy brand Smile Makers.

"Given that it’s hardly ever spoken about positively, masturbating for the first time can feel odd. But trust me, there is nothing odd about wanting to explore your sexual self and feel pleasure. It’s an important part of looking after our wellbeing!" says Marshall. Before delving into solo sex a year ago, I experienced a huge range of emotions — from guilt to shame to a lot of apprehension — so I more than understand the uncomfortable feelings that come with it. "The most important thing to know is this," continues Marshall. "Masturbation can consist of both external and internal stimulation. You might like both, you might like only one. Just like sex with a partner, it goes way beyond penetration. Most of us (80%) actually need clitoral stimulation to reach orgasm, which is no surprise given the pleasure powerhouse that is the clitoris." As with all things body-related, everyone is different so what works for someone else may not work for you (and vice versa). This really is a case of practice making perfect. We’re just here to help you play the first chord.

Ahead, read Marshall's comprehensive, realistic and beginner-friendly guide to masturbation.

"The best environment is the one that makes you feel most relaxed. As cliché as it sounds, your bed is a good place to start. Just like when you unwind before sleep, ease yourself into the zone. Turn down the lights, get under the blankets or light a candle, whatever makes you feel the most comfortable. You want to be able to focus on yourself and your pleasure so block out any distractions that might not serve your erotic imagination. Some people even love to use eye masks and earplugs."

"To begin, get hands-on and not just on your vulva (the external part). Feel yourself up all over. We have erogenous zones throughout our entire body that can be good to touch and help build arousal. Once you feel ready, start to explore between your legs. Cup your entire vulva with the palm of your hand and take note of how that feels. Then, with your fingers or a toy (more on that below), go between the labia to find your clitoral glans (the external part of the clitoris). 

One of my favourite first-time clit masturbation techniques is orbiting: circling round and round, back and forth. Switch up the pressure with your fingers or if you’re using a vibrator, start slow and increase the speed to find one that feels satisfying to you.

Stay here, between the labia, or move further down towards the vaginal entrance. Use just the tip of a finger or a vibrator to tease here. Maybe that feels like enough or maybe you’d like to insert just a little. This is called shallowing and can feel super pleasurable because 90% of the vaginal nerve endings are in the first third of the vagina’s canal. Top tip: Rather than a thrusting motion, try using your wrist to control movements. If you want to go deeper, go slow, and if using a vibrator, play around with the modes.

The most important thing is to listen to your body, pay attention to what actually feels good to you and let that guide you. There is no right or wrong or one particular order to stick to. Switch up the stimulation, go in and out or stay external — whatever you enjoy!"

"To really tailor masturbation to find out what you like, take your time. One big thing a lot of people forget to do is breathe. When we’re aroused, blood rushes to our pleasure anatomy so our body needs more oxygen. Plus, it can help us stay more present. When we feel too sensitive, especially on the clitoris, layering something between the vulva and our hand/vibrator can help — think underwear or a bedsheet."

"For some of us, using our fingers might be a little too much our first time around, and for others, having a toy on hand can help us to orgasm faster. After all, understanding our pleasure potential and what it feels like might just be the inspiration (and sensations) we need to keep exploring ourselves in the future.

When looking for your first sex toy, try ones that are unintimidating and fun. A classic bullet shape should be big enough for shallow or deep penetrative play, making it perfect for those that don’t know what they like yet. For something smaller, try a squishy lipstick vibrator. If you live with housemates, you can find some that are super silent, meaning you don’t need to worry about anybody hearing you get off.

Finally, as clitoral stimulation is a big yes for so many of us, look for a toy that is going to pleasure all its 10,000 nerve endings. One that sits directly on the clitoris will pack a punch. But for something more all-encompassing, try one that simultaneously places pressure on the labia, too. When the internal structure of the clitoris is aroused, it makes the labia puffier and extra sensitive, making this feel really good."

"Lube is life, seriously. A few drops of water-based lubricant when masturbating, with or without a toy, will decrease friction and increase sensations. It’s a no-brainer in my opinion. Sometimes, even when we’re super aroused, our nervousness to try solo sex for the first time might mean we don’t become as naturally lubricated as we need for stimulation to feel comfortable, let alone pleasurable. Using lube gives us a helping hand. Even when we are 'wet', more lube can feel great. Especially when trying out penetration for the first time."

"Your first time masturbating can leave you excited to keep discovering yourself — a new life hack unlocked. But it can also leave many of us feeling disappointed or confused. What about the orgasmic explosion of fireworks? Porn and films can lead us to think that pleasure is always like this. But it’s not. It can be more subtle, gentle or slower. Plus, we don’t always climax, which is totally normal. Orgasms aren’t the be-all and end-all of pleasure, they are just a peak. Ironically, putting pressure on ourselves to reach orgasm will actually make it less likely to happen, too. So relax and just enjoy the ride. The more we get to know what we like, the more likely the O will come in the future."

"Anything goes. There are so many wellness benefits to pleasure, such as better sleep, boosted self-esteem and stress relief. Like with anything in sex, trust your body — if it’s telling you it needs some rest or your vulva needs a timeout, do it."