Welcome to Masturbation May!

Welcome to Masturbation May, lovers! This month, we’re handing it over to two of our killer team, Ruby Woo (she/her) and Jacqui W (she/her), to talk about and celebrate all things masturbating, self-pleasure, orgasms, and to share some of their own personal masturbation experiments, experiences and AH-HA moments. Along the way, we’ll be hearing from you, our customers, over on our IG about your thoughts, your questions, your stories, and your big Os. Let’s gooo!

First things first, let us introduce ourselves:

Ruby Woo

I’m a self confessed flirt, sex pest and chronic masturbator. All jokes aside, my name is Ruby: I’m one sixth of the Kisskill cult, I’m sex-positive, a pussy power feminist, and lingerie enthusiast. I'm also a wannabe writer - which brings me here, to this very on-brand blog. To celebrate and introduce you to Masturbation May, we are going to share personal stories, facts, history and tips over the next four weeks. We encourage you to explore, enjoy and get comfortable with mazzing. After all, we all deserve pleasure in our lives, and if there is something more hedonistic than masturbation, I am yet to find it! 

Jacqui W

Hi, I’m Jacqui W! Another part of the Kisskill team, I’m an aspiring psychotherapist, self-love activist, and generally passionate about all things sex and sexual wellness. You name it, and - if it’s about sex - I’m into having a chat about it. This Masturbation May, we’d like to smash the stigma around self-pleasure, make talking about masturbation normal and shame-free, and celebrate the fact that it looks and feels different for everyone. It’s important to me that here at Kisskill we’re as gender-inclusive and sex-positive as we can be, so we’ll be trying our best to do so over this blog series.

Our first times


Flicking the bean, rubbing one out, finger painting, jacking off, mazzing; call it what you will, touching yourself is fucking awesome. I’m a die hard fan of the old playing the piano. Even before I knew what masturbating was, I was enjoying it. My first time was accidental. In fact, for a long time after I first experienced an orgasm, I still didn't know what I was experiencing. All I knew was that it made me feel like I was floating on clouds in heaven. I remember I was about 12, lying in bed before school when I discovered my clitoris. I opened up to a friend at school (no pun intended) and after that, we began sharing tips on how to achieve this euphoric feeling. Eventually we all started mazzing whenever we could, and sharing tips on which household objects to use… and avoid.

It wasn’t until I started having sex that I realised what I had been doing was masturbating. Bless my cotton socks. I've never been ashamed or hidden the fact that I love touching myself. The truth is, 17 years later and my daily ritual still involves at least one sesh a day. Can't sleep? Sad? Feeling ugly? Feeling sexy? Headache? I’ve got three words to say to you: Self-induced orgasm. The main difference between my mazz sesh in my teens, and my mazz sesh as an adult, is that I’m fully equipped with god's greatest gifts: the dildo and the vibrator. I no longer scrounge around the bathroom looking for that vibrating toothbrush (IYKYK), although some days I like to kick it old school and go analogue.

No matter how you get it done, no matter what crazy thoughts get you over the edge while your hand is down your underwear – masturbation is a simple pleasure that we should celebrate, embrace and do more of. An orgasm in general is amazing, and the fact I can give myself one whenever I feel like it, is absolute sorcery. I think it's quite obvious how I feel about mazzing. No recap needed. Ruby Woo x


I’ve been masturbating for as long as I can remember! My very first time was when I was around eight years old - I’d put one of my favourite soft toys between my legs and went to town grinding on it (said soft toy still lives on my bed even now - it was obviously a great time). I had no idea what I was actually doing; I just knew that something felt real good down there.

But even as I began to masturbate much more consciously in the years following, I didn’t have my first orgasm until I was 16 years old. Believe you me, though, I tried! I knew what an orgasm was (I’d been watching porn and reading erotica from a very young age), but I just couldn’t figure out how to achieve one. I remember once spending almost an hour masturbating, rubbing my clit in bewildered frustration, wondering why it felt so good but wasn’t resulting in the magical, throbbing, earth-shattering sensation I’d been reading about. I mean, it looked so easy in porn! And the female characters in my books climaxed left, right, and centre! WHY NOT ME?

In the end, my first O happened completely by accident: when I was doing leg lifts for my abs, on the floor of my best friend’s bedroom on a fine summer’s day. It caught me totally by surprise - as I squeezed my abs and my legs together, it suddenly began to feel warm and tingly between my legs. A few more reps later, and bam! It wasn’t earth-shattering, but it was pretty damn good. And that’s when I learned that, to this day, I can only reach orgasm with my legs stretched out and squeezed real tight!

Masturbating is still one of my favourite activities; as my gorgeous colleague Ruby has said, pleasure is a pretty good remedy for pretty much anything. These days, though, I’m trying to commit to practicing self-pleasure more consciously - think less quick-and-dirty dopamine hit, and more juicy, drawn-out, intentional self-loving (when I have the time) ❤

Thanks for getting to know us!

You may have gotten more than you bargained for, but you’re in for the ride now. Strap in, baby.

Next week on the blog, we’ll be sharing tips for beginners, a toy-buying guide for spicing up your solo sessions, and sharing some reasons why masturbating is actually good for you. 

In the meantime… keep an eye on our stories over on @kisskill_lingerie this week, because we’ll be wanting to hear all about YOUR first times!

Ruby and Jacqui xoxo


Artwork by Jae Besario @jae__bunny

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