Kinksplaining with Ena

You Want Me to Stuff How Many Sharpies up My What-Now???

What’s up with hole-stretching and why are some people into that?

Dear Ena, I connected with someone who said he’s into stretching a partner’s holes with Sharpie markers and it kinda weirded me out. What’s up with that? And why Sharpies? Best, Julia

Dear Julia, thank you so much for this question which transports me back to the beginning of my own kink journey. I, too, randomly stumbled upon the so-called Sharpie challenge, as well as anal and vaginal stretching, and had a similar reaction; what the hell is up with that?

I’ll start by going on a small tangent about the vaginal tightness trope, but I promise it will lead us to the core of your question.

Those of us with vaginas have been sold that we ought to be tight. Tightness is synonymous with youth, purity, and desirability. The tighter we are, the better sex feels… at least for our male partners.

A loose vagina signifies that we are just that; loose, used, and worn out. Basically, a slut.

Our society’s obsession with tightness has inspired procedures far more bizarre than kegel bells, vajajay steaming, and vinegar douching. Sticking wasp nests up there for rejuvenation sounds like a prehistoric home remedy, but is, in fact, a trend that peaked in the past decade, causing a flux of headlines like this one: Doctors Warn Women Against Putting Wasp Nests in Their Vaginas (New York Post in 2017).

The husband stitch, a controversial practice with no approved benefits, is another intended solution to unwanted looseness. The procedure, invented in the 50s, involves adding one or more superfluous sutures to repair perineum tearing caused by childbirth, with the purpose of tightening the vaginal opening to enhance the pleasure of the penetrating partner(s). Known to cause serious complications, physical and mental trauma, as well as immense pain during sex, many women have come forward with stories about having received the stitch without their consent.

The vagina snaps back

Vaginas are wonderfully strong and pliable organs. Designed to accommodate the delivery of entire babies, they don’t get loose from use. This notion is not only offensive and sexist but clinically incorrect. On the contrary, most of those who give birth come out of it—after some necessary recovery time—with pelvic floor muscles that are more toned than before. [Source]

So, if childbirth doesn’t cause permanent vaginal looseness, penetration certainly won’t, regardless of the size of who—or what—we insert.

A muscle that can’t relax and be soft is not strong, but merely tight and stiff.

[My favorite yoga teacher, Valerie]

All of that being said, and though I was never personally too concerned about getting used up, I was raised with the mantra that tight is right. Therefore, my mouth was agape when I first came across pictures of people inserting everything from gargantuan sex toys to bottles, girthy eggplants, entire fists, and yes, fistfuls of Sharpie markers into their vaginas and/or anuses.

Like you, Julia, I asked:

“Why would anyone do that?”

The appeal of stretching is expansive (!), but I’ll start with the most obvious…

It just feels good

Many like getting stuffed or stretched because they enjoy the so-called fullness sensation. Others may find it uncomfortable or straight-up painful. We’re all wired a bit differently.

If we look at the anatomy of the clitoris, which legs (crura) line the vaginal wall and the juxtaposing rectum, it makes perfect sense that the added pressure increases sensitivity, which in turn can feel amazing. This is also true for people with prostates, in which anal stretching will stimulate this highly sensitive gland.

Bragging rights

Some train to lift exceedingly heavier weights or run marathons. Others have different physical goals, like taking the largest toy—or a record amount of Sharpies—up one or both of their holes. I suppose we’re wired differently here too.

Anyone with a competitive spirit is familiar with the deep sense of pride and satisfaction — as well as the dopamine and endorphin rush — that comes with conquering new challenges.

What I’ll call gamified stretching, often accompanied by public bragging posts, is an accessible and fairly safe way to indulge our competitive urges—and not to mention, our exhibitionistic ones.

Embrace your inner hussy

This is where the concept of stretching gets extra interesting. Nodding back to my intro; in a world where tightness is a signifier of integrity and purity, we enter the parallel world of kink and BDSM to find these virtues turned on their heads. Here, opposing characteristics — like being a whore, a slut, a size queen or king, or a fuck-toy with gaping holes ready for use—are boasted about and reciprocally praised.

Sounds demeaning? Not your cup of tea? I get it, but… isn’t there something badass and empowering about spitting in the face of everything we’ve always been told we should be?

Pride is not the opposite of shame, but its source. True humility is the only antidote to shame

[Lord Iroh, Avatar: The Last Airbender]

Our kinks often reflect society’s and our own personal taboos. When we eroticize that which we otherwise perceive as wrong, shameful, gross, scary, scandalous, etc, it can have a cathartic effect. Embracing our fears, and even making a caricature of them, can help disarm and remove the power they hold over us.

Shame is an incredibly potent emotion whose best antidote is often the very thing we’re ashamed of. The desire to be humiliated, by ourselves or at the hands of others, can act as a form of exposure therapy to access our shame and transmute it.

Stretching to be the perfect slave

Further down the BDSM rabbit hole we find Master/slave dynamics in which stretching is a common component of slave training protocol.

The subject matter, which will need its own article, was artfully portrayed in the scandalous erotic novel, Story of O. Written by Anne Desclos under the penname Pauline Réage in 1954, the story follows O, who’s taken to a secret French château to become a sex slave. Her schooling also involves anal training.

What her lover wanted from her was very simple: that she be constantly and immediately accessible. It was not enough for him to know that she was: she was to be so without the slightest obstacle intervening, and her bearing and clothing both were to bespeak, as it were, the symbol of that availability to experienced eyes.

But, what’s with the Sharpies?

At last, we arrive at the markers. If you’re unfamiliar with the Sharpie challenge, you can Google “Sharpie challenge vagina” (safe search off), and you’ll catch on. For a less graphic depiction, the game is about how many markers you can fit into either or both holes. Often, tally marks are added to the thigh or ass of the stuffed person to keep count.

If your question is still why? My answer is why not? The saying goes that if you can think of it, it’s on the internet, and that’s likely what happened here; someone thought of it, put it on the internet, and it spread.

I’m also making the educated assumption that the reason Sharpies are used, as opposed to, let’s say, Eddings, comes down to their ergonomic shape. Perfectly curved and tapered, they can be inserted into the vagina and anus, one by one, without damaging the sensitive skin around these orifices.

This challenge combines most of the reasons why people love stuffing and stretching while adding elements of silly, playful fun, which, in my opinion, should always be a component of sex and kink, no matter how serious we may be about our chosen practices.

I did write the CEO of Sharpie and requested a comment, and have yet to receive an answer, but, judging from this statement on the company’s website, the practice is well-aligned with their values:

Sharpie stands for far more than just markers. The Permanent Marker, born for unique, unruly, courageous, outrageous self-expression that never, ever fades from glory.

I’ll wrap this up with a quick note on safety. When it comes to stretching any of the intimate orifices, the rules for stretching the rest of our body and muscles apply: Go slow and stretch just past the edge of your comfort zone, but never to the point of acute pain.

Further, pay attention to hygiene and body safety to avoid tearing and infections, always use flared-based toys or objects for anal (unless your humiliation kink insists you visit the ER with a foreign object trapped inside you), and for goodness sake, be generous with the lube.

Stay silly, outrageous, supple, flexible, and strong, but most of all, stay safe!

© Ena Dahl 2023 [Kinksplaining with Ena]

In this column, Kinksplaining with Ena, I discuss, dissect, and investigate sexual fantasies, desires, and kinks that may be perceived as offbeat and unorthodox. I approach each topic, which was prompted by a question or issue that has been brought to me through my work as a sex and kink educator, not as a scientist, but as a curious explorer, philosopher, and avid researcher of the human body, mind, and sexuality. My goal is neither to lecture nor to present absolutes, but to illuminate, destigmatize, and create discourse from a nonjudgemental, loving place. I, therefore, welcome your follow-up questions and add-ons in the comment section. Also, feel free to email me your own question via [email protected]. Thank you for being here!