Wanking on the Rag: A Squeamish Masturbator’s Guide

I love to masturbate. Um, of course I do, I write about sex toys. But I mean, beyond just doing it for the physical pleasure of it, I also enjoy it mentally and emotionally: it’s a way for me to recharge, to unwind, to be good to myself.

So it sucks that there’s one week every month where masturbating is more mess than it’s worth. Or is it?

Here are some of my top tips for jerking off when you’re bleeding. Some of them are overlaps from my post on menstrual sex, but solo sex is worth honoring, too!

1. Choose a nonporous toy. If your collection includes toys made of jelly, TPR, CyberSkin, etc. (shame!), skip them for the time being. You can always use a condom over them, which you should be doing all the time anyway, but it would be best to just bite the bullet and upgrade to a toy you can use safely during your period.

Many of my toys have been subjected to menstrual blood, including my all-white Ella and my beloved Pure Wand. Nonporous toys should wash totally clean with a little soap and water, and the non-mechanical, waterproof ones can be boiled to sanitize. I do have one jelly toy left over from my ignorant days, which I never use anymore – but if I did, I’d leave it alone during my period. Bloody bacteria growing in toy pores = gross!

2. Buy yourself a blood towel. It should ideally be dark-colored and large. Hell, buy two, especially if you’re a squirter. Every time you masturbate or have sex during your period, lay out the towel underneath you so you can have at it without worrying about a mess.

If you’ve got the cash, why not spring for a red Liberator Throe? I can’t think of a better way to honor your divine reproductive essence while keeping your sheets clean! (On a related note, if anyone would like to buy/send me a Throe, please get in touch…!)

3. Investigate alternative menstrual products. Jade and Pearl make sea sponges which you can stuff up your vag at moon-time. They make it possible to be penetrated without mess, whether by a partner or by your own fingers or toys.

I also have a wide variety of menstrual cups which I use for everyday period wear. Depending on the cup, I may be able to penetrate myself shallowly or not at all while wearing one, but they’re great if you just want to masturbate clitorally.

4. Stay away from your cervix. Some folks get very sensitive while they’re bleeding, especially in the cervix area. If this is true for you, try a toy that’s squishier, shorter, or focuses on your G-spot rather than the far reaches of your vagina.

If you really crave a good pounding, maybe take an ibuprofen half an hour before attempting it, and avoid hard materials like glass and steel. Flexible silicone will be your best bet during this time.

5. Think of orgasms as painkillers. Sometimes, when I’m on my period, I feel miserable and achy and have no desire to jerk off. My cramps get so bad that I just want to lie on the couch and watch bad TV. But then I remind myself that I’ll feel better if I force myself to have an orgasm – and guess what? I always do.

It doesn’t have to be a big production. If you’re feeling too sore or lazy for penetration, don’t bother with it. Just grab your favorite clit toy and get off in a way that’s comfortingly familiar to you. You may not feel terribly enthused at first, but power through it if you can: there’s a good chance your cramps will ease up if you can make yourself come.

Jerking off can be a very healing and affirming thing to do during your period, a time when we’re most likely to have complicated relationships with our genitalia. Stop worrying about the mess and just be good to yourself!

Menstrual Sex: It’s About Bloody Time!

I think the only time I’ve ever used the word “squicky” in real life was while telling my friend how my new boyfriend felt about menstrual sex. “It’s just weird for me, I guess,” I said, “because [my ex-girlfriend] was so okay with going down on me during that time of the month, and [the new boyf] is soooo not.”

It’s true – this was a tough adjustment for me. My ex had a vagina too, so she understood that menstruation isn’t such a big deal – but it wasn’t just that; she was a messy, reckless person in many ways, the type of girl to slather herself in paint and make breast prints on big pieces of watercolor paper. I think she was more inclined to “ride the crimson wave” because sexuality didn’t scare her, not even a little, not even the weird parts. My new boyfriend wasn’t like that, and his apprehension made me feel shitty about my lady-bits.

But then I rubbed off on him. Me and my relentless sex-positivity and vagina-lovin’. He must have absorbed some of my feminist unabashedness, because soon enough, his blood-related worries dissolved.

Here are some things that changed his mind, and that might change yours or your lover’s mind about period sex too:

1. Menstrual cups. Embarrassingly, I have a cup collection – two DivaCups, a Yuuki, a Lunette, and a Meluna. I just like to have a variety of color and size options – the average woman will only need one cup.

These things are great for a multitude of reasons that don’t have to do with sex – better for the environment, for the body, for the wallet (if you don’t collect them like me) – but they make sex easier too. While it is possible to have intercourse with a reusable cup in place, I don’t recommend it – I use them to facilitate oral sex instead. They keep the blood inside, so as not to freak out a partner, but they don’t dry up natural juices the way a tampon would if used in the same way. Worry-free cunnilingus, yum!

2. Menstrual sponges. I have some by Jade and Pearl – they are fairly cheap and easy to use. Truth be told, I am not a fan of sponges for everyday menstrual use – they’re not much better than tampons when it comes to body-safety and drying me out, and I find that they leak when I sneeze or laugh too hard. But! They work very well for period sex. (I’ve never used Softcups, but I hear they work just as well for this purpose.)

When inserted, sea sponges feel remarkably similar to the surrounding vaginal walls – soft, textured, and, uh, spongy. So you can tuck one up by your cervix and it’s very likely that neither you nor your partner will even be able to tell you’re on the rag. Just one word of warning: don’t go trying to pry out the sponge immediately after sex to empty it – during arousal, the cervix pulls up and back, taking any surrounding objects with it, so give it a few minutes or you might start panicking about not being able to get the damn sponge out.

3. Thick, dark towels. Really, these should be a part of everyone’s sex arsenal; if you don’t need towels at least once in a while, you’re doing it wrong, if I may say so. At the moment, I just use knockoff pashminas I don’t care about, but in the future, I’d like to upgrade to a Liberator Throe, a sex blanket that can absorb anything you squirt at it.

4. Mental preparedness. Yeah, menstruating vaginas taste a bit like iron. That taste doesn’t mean you’re getting blood in your mouth (necessarily), it just means you’re licking a healthy, normal vulva, so don’t fret.

Not everyone has to be okay with every sex act. I’m definitely not going to judge anyone who really feels that menstrual sex is not for them. But I want people to feel more equipped to have it if they want to… especially since orgasms are such a wonderful cure for cramps!