Vaginal Masturbation, A Personal History

You can also listen to this story in Episode 35 of the SEX COMMUNICATION podcast as I share additional details in an off-the-cuff recording… check them both out for the full picture.


Did you know that babies touch themselves? For reals it’s true, and if that doesn’t normalize masturbation, I don’t know what can. Now I’ve had fantasies and sexual inclinations for as long as I can remember, but sadly I don’t recall my own baby beat off sessions to recount for you.

However! I do recall a wealth of other details regarding my rocky journey to become the open, self-lovin’ woman you now know.

My earliest memory of touching myself is putting my hand between my legs, cupping my vagina, while trying to fall asleep. I think it must have started around the age of 9? It never really progressed from there; it was a satisfying feeling, one of protection, comfort, pressure. It was essentially my sleep aid — later it would inspire my first sharing of sex tips though I didn’t quite see it this way at the time.

I was maybe 12 years old, a devout attendee of Girl Scout camp, and one summer night I led the other occupants of my tent through a guided-masturbation exercise. Ok that may be overstating a bit; basically the topic of masturbation had come up and I decided to mention what I did, described how I did it and as far as I know (it was dark of course) we all tried it together. Also by “together” I mean at the same time while remaining in our individual cots. You can read more about that night and the other trouble I got myself into here.

After that I finally started having sex and was more interested in that than figuring out how to make myself cum. My teenage years and early 20s passed uneventfully but full of partner sex.

It wasn’t until the age of 28 or 29 that I finally masturbated to orgasm; it happened while watching porn and fast, like one minute at most. I watched quite a bit of porn after that, as you can imagine. I got my first toy, the classic Rabbit shortly after, at the age of 29 or 30. Both worked well and helped counter the “but I see the man behind the curtain” feeling that comes with attempting to beat off without visual or physical assistance. I just couldn’t clear the mental hurdle of overthinking and hyperawareness of self-generated pleasure. For me, the orgasms come when I can lose myself in physical feeling and fantasy, which are both tied to my ability to imagine being touched by someone else.

Fun fact, I only masturbated to porn as an experiment, prompted by a terrible relationship and the porn-viewing habits of my partner.

Moving into my early 30s, my drinking and drug use was escalating at a steep pace and I started relying on masturbating to porn in the wee hours of the morning to help me fall asleep for a brief spell before having to leave for work. It was during this same time that I discovered my body was more prone to fantasy and arousal at midday; naps especially got me all hot and bothered. One magical Saturday, I spent several hours masturbating with my Rabbit over and over again. And then it died. I knew the moment I smelled the acrid electric burn that the motor had burnt out.

I kept this now defunct vibrator in my nightstand along with a smattering of other devices that never managed to get me off: a hard g-spot vibrator, a small handheld waterproof deal… I shut the door and went back to porn exclusively UNTIL I began dating a man who owned a Magic Wand and one day made my vagina cry.

When I say, “made my vagina cry” I mean this in the best way. You see he’d pull out this giant device to use on me while I was restrained in a variety of manners so I already knew what it felt like, what it could do; it was a flash of genius the night I thought to position it under me during anal sex when I had an orgasm to end all orgasms. I felt like my pussy was absolutely weeping with joy it felt so fucking good.

As I am not a physician or biologist or any such person with medical training, I cannot say for certain exactly what happened or why this particular combination of anal sex plus intense pressure and vibration on the clit worked so well, but who really cares? I had discovered the holy grail of pussy pleasure.

That experience led to the purchase of my own Magic Wand, which I began using in combination with the defunct Rabbit to achieve a similar orgasm by myself. But first I had to rip off the corded motor part of the broken vibrator turning my old toy into an effective dildo. By inserting the Rabbit dildo into either my vagina or asshole with my right hand and then pressing the Magic Wand against my clit with my left hand, I was able to simulate the anal sex/vagina crying incident. Something about applying pressure from the outside while thrusting a device on the inside, effectively sandwiched my inner lady parts to the point of full-body orgasm. I would later realize I was hitting my G-spot, at least I think so, further research has brought on the discovery of the “A-spot” which may have been involved, who knows? It felt fucking amazing and that’s really all that matters.

These days I still rely on the use of two devices to cum without porn. I still use a Magic Wand, though now a new cordless version [thanks to an international travel mishap]. I recently broke the Rabbit dildo in half from repeated use; my new insertable is a ridged vibrator called a Tiger. I have a few other gadgets, some smaller things to stick up my butt and whatnot, but my go-to is the aforementioned duo.

Happy Masturbation Month!