Unlike right-wing politicians, when I invoke the George Orwell novel 1984, it’s not to make sweeping claims about my political enemies. Usually, it’s to tell people that their sexual fantasies are normal and fine.

People have all sorts of sexual fantasies, and some of those people wonder whether their fantasies are, in some sense, “immoral.” Is it bad, for example, to jerk off to the thought of your ex? What about your sister’s ex? What about your sister?

I am aware that the title of this essay sounds like some kind of bathroom-related thing that would be cringe to discuss in polite company. THAT IS NOT WHAT I AM TALKING ABOUT. I am talking about Tinder. SWIPING, NOT WIPING, PEOPLE. (Although you should also be wiping. I mean. You know that. Anyway. Sorry. Let’s proceed.)

I recently had the absurdly millennial experience of re-matching with someone who I went on two (2) dates with, five (5!) years ago. There was, and is, no ill will between us – I gathered that we were both pretty into each other, but ultimately he ghosted me for a while because of a (confirmed, legit) chronic illness he has, which flared up suddenly. He later apologized retroactively for the ghosting and explained the reason for it, which was a reason I had already considered. In fact, I would have already fully assumed it was the reason, if not for being wildly insecure (lol, fun).

Content note: discussions of – but not much detail about – trauma, emotional abuse, daddy dom/little girl roleplay, spanking, kink-shaming.

People make a lot of assumptions about you when you’re into DD/lg (daddy dom/little girl roleplay). One of the commonest and darkest of these is that the kink must have been caused by the presence of underlying “daddy issues.”

The phrase “daddy issues” is, itself, a red flag. It is a phrase which literally communicates that the person using it believes a victim of father-related trauma is both somehow responsible for that trauma and profoundly and permanently affected by it. It reduces a person, almost always a woman, to a sad little plant who grew from the seedling of how her father mistreated her – as if that is the totality of her being, as if she was not also enriched by the soil she grew in, the water she drank, the sun she photosynthesized.

Friends, I won't lie to you: "This is so demisexual" is something I have yelled at my TV on more than one occasion. [Insert butterfly meme of me looking at a perfectly standard piece of media that happens to link emotional intimacy with sexual intimacy and going, "Is this... demisexuality?"]

For those who don't know, demisexuality is an identity on the asexual spectrum, meaning that it exists somewhere between allosexuality (experiencing sexual attraction) and asexuality (not experiencing sexual attraction). Demisexuality is characterized by the need for some kind of emotional connection to exist before sexual attraction can be felt. This manifests in all sorts of different ways for different people, because human psychology is complicated. For instance, I can start to get horny for celebrities I've seen in many pieces of media (um, you read my thoughts on Bo Burnham, right?), purely because our parasocial relationship has made me feel like I have an emotional connection with them.

Anyway, sometimes I see stuff on TV and in movies that reads as very demisexual to me. It might be an "enemies to lovers" storyline in some medical drama, in which the characters' sexual chemistry seems to build with each deeply illuminating argument they have on screen, or it might be a high school rom com where two best friends suddenly realize they were each other's perfect match the whole time... or it might be a Netflix dating show where people are financially incentivized not to fuck each other.

Content note: As you may have guessed from the title, this essay will discuss psychedelic drugs and their effects on the human psyche.

Housekeeping note: Hi, friends! This is a rare “free for everyone” edition of Sub Missives; I hope you enjoy it! I wanted to let you know that the juiciest, most vulnerable and intimate content in this newsletter is only available to premium subscribers (i.e. paying subscribers), for the reasons that 1) I just don’t feel comfy publishing that stuff on the public internet for all to see and 2) a girl’s gotta eat and pay her bills. If you’d like to join so you can receive an essay every week about my innermost thoughts and oddest experiences related to love, sex, kink, and more, while supporting my work so I can keep doing it, you can sign up for a premium subscription for $5/month or $50/year at katesloan.email. Thanks, loves!

I almost made a terrible mistake while I was in a touring improv troupe. (And no, the mistake I’m referring to is not simply being in a touring improv troupe to begin with.)

My high school was an arts school that attracted students from all around the city. One of the ways we did this was a marketing strategy of sorts, known as “school tours.” This was where teachers would choose a select few students who enthusiastically excelled at music, dance, or improv, and would then take those students on a “tour” of several local middle schools so we could perform for their students in an assembly and entice them to apply to our school. We would do this for two weeks each October, during which time our teachers knew not to expect us to come to class or hand in assignments – because we were on TOUR, baybee!

I have always had intrusive thoughts about crushes, have always gotten people stuck in my head the way I get songs stuck in my head: they loop for days on end, maddening, all-consuming.

I’ve often wondered if there is a neurological basis for this, possibly having to do with dopamine. I’ve wondered this even more since reading neurologist Oliver Sacks’ book Musicophilia, which details (among other nerdy musical brain-science anecdotes) a number of cases in which certain brain injuries resulted in far more persistent and annoying musical “earworms.” I don’t think I’ve ever experienced a brain injury, but perhaps it’s a wiring problem. Who knows.

What I can tell you is that it gets very annoying at times. In the throes of it, I often find it difficult to think, let alone get any work done. I’ll become more interested in obsessively googling my crush, or posting hot selfies I hope they’ll enjoy, than doing anything of real value or purpose. I concoct absurd fantasies and replay them incessantly, automatically, in my mind. I’ll lose sleep staring at my phone or listening to podcasts the person has guested on or scrawling in my journal about how sad it is that I’ll never get to kiss them. I've been doing versions of this, on-and-off, for about 20 years.

But I am a big believer in working WITH one’s natural tendencies, not against them, whenever possible. There are a few ways I channel this obsessive energy into actual productivity and other positive outcomes.

Hi friends! Brief programming note: As you may have noticed, I've switched over from Substack to Buttondown. Substack has given enormous financial payouts to numerous people of questionable ethics (to say the least), most noticeably the genuinely dangerous and deeply bigoted blowhard Graham Linehan.

I've wanted to make this switch for quite some time but haven't had the spoons/energy, but fortunately, my extremely generous and smart spouse Matthew Bischoff helped me transfer things over, with the help of Buttondown founder Justin Duke. You will continue to be billed the same way at the same rate, so you don't need to do anything; everything has been transferred seamlessly so far as I can tell. Please let me know if you experience any interruptions or issues, but all should be fine as long as submissives@katesloan.email is in your email client's whitelist. Thanks for joining me on this journey!

I have a problem with change. It's a very Taurus-y quality. When a big life change is on the horizon, like moving house or ending a relationship, I am filled with trepidation and stubborn resistance.

I have been on Twitter since 2007 so I have tweeted some embarrassing and baffling things over the years. Here are some of those tweets, with commentary from modern-day me. We can all grow and change!

Oct. 19, 2007: "Danny the song & dance cat" from Cats Don't Dance is pretty much the sexiest dancing cat ever. He was also my first crush as a child.

In retrospect, I am surprised I announced, on Twitter, at age 15, that I had a crush on a cartoon cat. I would be embarrassed to tweet this today, though it is still true. Incidentally, I just looked into it and Danny was voiced by Scott Bakula, who is, y’know, cute but not really my type. I guess I just love gregarious weirdos who are way too into musical theatre, and are, maybe, cats.

Feb. 9, 2008: I really want Ryan Seacrest & Simon Cowell to have sex, if they haven't already. Shhh.

My inbox is habitually full of PR reps pitching their latest “libido-boosting” product. Supplements. Gels. Exercise regimens. CBD-infused soft drinks. Whatever.

The thing about “boosting one’s libido” is that the reasons for having a low sex drive in the first place are often not directly addressable with a product. I think this is especially true for anyone subject to systemic stress and oppression – women, trans people, people of color, etc. – and I also think it is especially true during a globally traumatic event like a pandemic. In many cases, it’s not a physical issue causing your libido to dwindle (although you could certainly check with your doctor just incase). No, I think most libido issues arise from our psychology. Stress. Trauma. Relationship tensions. Culturally-instilled body insecurities. Gender anxiety. You get the picture.

With that in mind, here’s a list of products that actually boost my libido…

A sleep mask and earplugs. Not necessarily for sensory deprivation play, although that too – but mainly I just use these to sleep better. When you sleep longer and more deeply, you have more energy, you’re less irritable with partners or potential partners, and you’re operating at a higher level in terms of mental and emotional processing. For me, this all means that when I’m sleeping well, I have better sex, and am able to enjoy it more. I think that makes sleep a worthy thing to invest in. (For the record, my favorite sleep mask is the Nidra Deep Rest, and I use Mack’s slim-fit soft foam earplugs.)

I often think about the correlations between my professional life and my personal life, the ways in which they mirror each other and teach me the same lessons.

I thought about that connection today, when – in a stern email to someone who had repeatedly asked if I would publish their spammy guest post, a service I do not offer – I typed, in bold, “No exceptions will be made under any circumstances.”

I stared at the sentence, and thought – first with amusement, and then with a tinge of sadness – what would have happened if I had held my boundaries just as firmly as this, in social and sexual situations, from the very beginning? What difficulties would I have been spared? Who would I have become?

I am a big fan of “personal policies,” loose little rules I create for myself that help guide me in the direction of my ideal life. I know that these do not work for everyone; many people have told me either that they slip into old unwanted behaviors too much if their own willpower is their only steward, or that setting rules for themselves feels too restrictive and doesn’t leave enough room for spontaneity. For me personally though, because I know that they aren’t hard-and-fast rules but merely strong suggestions that Past Me has made to Future Me based on intimate firsthand knowledge of myself, I find that having personal policies helps me a lot.

Yet again, a man on Reddit is insisting that “women are shallow” and that “women only want to date Chads with six-packs,” and yet again, I am laughing my ass off.

Let me be clear: it’s not that I take issue with this man feeling insecure about his physique; appearance-based strictures affect us all in this culture, and an unfortunate one for men is the proliferation of muscly bodies and the widespread sense that those bodies are what (straight and bi) women want.

But I can’t help laughing at this particular sentiment on this particular day, because 1) women are not a hive mind, and 2) I’ve just spent a solid hour getting horny over a gangly Twitch streamer because of his encyclopedic knowledge of Pokémon games.

This has been a hardcore quarantine hobby of mine – playing these games, which I’ve loved since childhood but hadn’t touched in several years, and watching other people play these games. Horniness is not habitually part of my gaming experience (I don’t play the porn games that people like Ana Valens write about), but intelligence and nerdiness are habitually part of my attractions, so it makes sense that I develop smouldering crushes on everyone from home improvement YouTubers to Jeopardy champions to, yes, Twitch streamers.

Succession is such a weird show. It centers on Waystar Royco, a fictional media conglomerate that’s sort of like a mix between Fox and Disney, and the people at the top of the corporate food chain therein: company CEO Logan Roy, his four adult children who all want to take over the CEO job someday, and the advisors and lackeys they employ. It’s a show about business, and capitalism, and trauma, and abuse. It’s a show about the ways that our earliest childhood experiences can shape who we are for the rest of our lives. It’s also, at times, a show about sex, attraction, eroticism, and power.

Because it amuses me to do so, in today’s newsletter I will be selecting sex toys that capture the essence of characters on this very popular show. Feel free to hit “reply” and let me know whether you agree with my picks!

I got home from New York two weeks ago and I have been luxuriating in my solitude.

I love my spouse, my friends, and my family very very much, so do not take that last sentence as a slight toward any of them. I just also love spending time alone. Not only do I love it – I need it. My brain seems to run at an optimal level when I’ve been afforded big chunks of 100% solo time recently. I think I’ve always been that way.

But since this is a newsletter ostensibly about sex, it bears mentioning that my sexuality also seems to benefit from me getting adequate alone time.

I remember that when I ended a 3.5-year-long relationship at age 22, I had this huge, expansive sense of sexual freedom – not just because I was able to date and fuck people who had been off-limits to me in my monogamous partnership, but because I felt like I was rediscovering my own body as my own body, rather than being a body that another person partially “owned” or at least had a vested interest in. My partner hadn’t demanded that I shave or stay clean for him; he hadn’t expected me to be sexually available to him at all hours of the day; he certainly hadn’t seen himself as the primary arbiter of my body – and yet somehow I had felt obligated in these ways nonetheless. I had felt it was my duty to look and feel and smell and taste a certain way for him. And now that I was single again, those responsibilities were just… gone.

Content note: daddy dom / little girl language

I love daddy doms. I have for years. But it’s not just a sexual thing.

When I say the phrase “daddy dom,” what I really mean is a kinky person who is dominant or dominant-leaning, and whose dominance manifests in a way that’s explicitly about caring for their submissive-leaning partner(s). Granted, even some of the more discipline-oriented dominants out there are doing what they do out of deep care and love, but I think what sets daddy doms apart from the others is that the caretaking is part of the “fiction” of the kink, part of its narrative for both/all participants, rather than being implicit subtext – and the caretaking is part of what both/all participants find hot.

Content note: There is a part in this essay where I take some drugs and it seems like I might be sexually assaulted or something, but don’t worry, I didn’t get assaulted and there is no assault or other sexual misconduct in this piece.

Something really weird just happened as I was brainstorming ideas for this week’s newsletter.

I was scrolling through old screenshots, hoping to happen upon a text conversation or sext-y interlude that would trigger a thought that would trigger a newsletter.

The fuckboy/fuckgirl/fuckperson who bangs you well but who you will never see again

The princes in Into the Woods are the closest characters to our modern understanding of the term “fuckboy” in any pre-1990 musical that I’m aware of. And in no song is this more apparent than “Any Moment,” the flirty and feather-light song Cinderella’s prince sings to the baker’s wife after they share a mutually extramarital tryst amongst the trees. It has the rhythm of a text exchange you’d have with someone who fucks incredibly well but who, you eventually discover, has no intention of ever seeing you again once the bloom is off the rose.

You: Idk if I can do drinks tonight, I have to get up early for work tomorrow…

Them: Aww cmon! I’ll make it worth your while ;)

Recently I went through the notes I’ve taken during my last several therapy sessions, and for each session, I distilled the main thing I learned into one sentence. Here are those one-sentence summaries of my last 25 sessions. I hope they give you some peace, or at least some food for thought – especially if you’re having a hard time right now due to being with family for the holidays. (These are written in all caps because they remind me of Jenny Holzer’s “Truisms,” which were always in all caps as well.)

1. CHANGE IS SCARY BUT ALSO EXCITING.

2. SINCERITY IS TERRIFYING BUT IT GETS YOU WHERE YOU WANT TO GO.

3. YOU DON’T NEED EVERYONE TO LIKE YOU AND IN FACT NO ONE IS UNIVERSALLY LIKED.

4. WORKING THROUGH CONFLICTS WITH HONESTY AND INTEGRITY IS ALLOWED TO BE A SLOW PROCESS.

5. YOU ARE ONLY HUMAN AND PEOPLE WHO LOVE YOU SHOULD ACCEPT THAT (WITHIN REASON).

6. THERE IS NOTHING INHERENTLY WRONG WITH HAVING COPING MECHANISMS BUT THEY CAN BE LIMITING AT TIMES.

7. OTHER PEOPLE’S NEGATIVE EMOTIONS ARE NOT AUTOMATICALLY YOUR RESPONSIBILITY OR YOUR FAULT.

8. YOU WILL INEVITABLY HURT PEOPLE; THE TRICK IS TO AVOID HURTING PEOPLE INTENTIONALLY.

9. THERE IS NO POINT IN ENGAGING WITH SOMEONE WHO REFUSES TO VIEW YOU AS A HUMAN BEING.

10. YOU ARE ALLOWED TO FEEL PROUD OF YOUR ACCOMPLISHMENTS AND IN FACT YOU SHOULD.

11. REST AND LEISURE ARE YOUR BIRTHRIGHT AND “WORK ETHIC” IS A CAPITALIST CONSPIRACY.

12. THERE IS NO SUCH THING AS A PARTNER YOU “DESERVE,” ONLY A PARTNER YOU WANT WHO WANTS YOU BACK.

13. STRUGGLE AND PAIN ARE NOT THE ONLY MEASURES OF ACHIEVEMENT.

14. THE “9-TO-5” LIFESTYLE DOESN’T WORK FOR EVERYONE AND THAT’S OKAY.

15. MAKING MISTAKES IS PART AND PARCEL OF BEING HUMAN.

16. MAKING MISTAKES DOES NOT MEAN YOU ARE A FAILURE WHO DESERVES TO DIE.

17. THERE ARE NO “GOOD PEOPLE” OR “BAD PEOPLE,” JUST PEOPLE WHO MAKE VARIOUS CHOICES.

18. AVOIDANCE IS SOMETIMES A GOOD COPING MECHANISM BUT ONLY IN THE SHORT-TERM.

19. HYPERVIGILANCE AND HYPER-SCRUTINY KILL CREATIVITY.

20. HETEROPATRIARCHAL AND ABLEIST NARRATIVES ARE NOT MANDATES.

21. IT IS RARELY IN YOUR BEST INTEREST TO REPLY TO SOMEONE WHILE ACTIVELY ANGRY OR UPSET.

22. IT IS OFTEN MORE IMPACTFUL AND LESS HARMFUL TO CRITICIZE SYSTEMS THAN INDIVIDUAL PEOPLE.

23. SELF-COMPASSION IS NECESSARY AND TRANSFORMATIVE.

24. ABUSE IS NEVER THE FAULT OF THE VICTIM.

25. YOUR HEALING IS NOT CONTINGENT UPON THE ACKNOWLEDGMENT OR REPENTANCE OF YOUR ABUSER.

Content note: This essay discusses the nonconsensual sexualization of minors (namely, me) by older internet strangers.

I was 14 when I started posting outfit photos almost every day on Flickr, and strangers started having Opinions about my pictures almost immediately.

The comments I received were a mix of 4 basic categories:

Content note: This essay will touch on sexual assault and coercion, alcohol, victim-blaming, and rape apologism. I should also say that I’m writing this how I remember it, which may or may not be fully accurate to what actually happened.

In the 12th grade, I took a class called Writer’s Craft, which ended up teaching me a vital lesson about feminism.

The class was a broad survey of various different writerly forms. We studied, and then wrote, everything from Shakespearian sonnets to sitcom scripts. Toward the end of the year, we were tasked with doing some journalism of sorts: going out into the world, interviewing people, and writing about what we learned.

Note: This is an article I wrote in 2020 for a sex toy company who have since majorly fucked me over (not in the fun way), so I feel no qualms about sharing it here 😂 Hope you enjoy!

There are lots of skills you learn as a person with chronic clinical depression. How to explain your mental health history to a new doctor. How to procure yourself a decent meal when you can barely get out of bed. How to gently decline a social invitation when chipper small-talk feels impossible. One of the skills I’ve had to learn in my journey is how to adjust my sex life when depression comes a-knockin’.

Contrary to popular belief, depression doesn’t automatically drain the sexual desire from those it afflicts. Mental health advocate JoEllen Notte conducted an informal study of depressed folks for her book The Monster Under the Bed: Sex, Depression, and the Conversations We Aren’t Having, and found that more than a quarter of her respondents reported an increase in libido during depressive episodes.

For nearly 10 years, I have been receiving the same type of feedback when I tell people that part of my job entails testing and reviewing sex toys. “Must be nice!” people will say, or “So you get paid to masturbate?!” or “How can I get that job?!” That last one particularly annoys me, because this is not really a job you get, it’s a job you make, a job you choose and chase and work toward (and it is, itself, a privilege to have the time and money to do that). No one taps you on the shoulder with a dildo-shaped sceptre and says “I now pronounce you a sex toy reviewer.”

I am well aware how whiny and spoiled it makes me sound to shout “Putting pleasurable objects on my genitals for a living isn’t all fun and games, you know!!” but I really feel that most people don’t know what they are actually talking about when they say it sounds like a desirable job. It is a desirable job, but for me, the desirability is moreso about the flexible schedule, the largely self-directed workflow, the ability to be my own boss. The actual testing-sex-toys part is not always pleasant or fun, in the same way that it’s not always pleasant or fun for a book critic to slog through the latest schlocky tome, knowing they’re on deadline to write a polished, thoughtful essay about it. People tend to get into literary criticism because they love books – and, likewise, I got into sex toy criticism because I love sex toys – but that doesn’t mean the work isn’t work, and sometimes work is annoying and boring.

There are times when sex toy reviewing thrills me to my very core. These tend to be times when a toy genuinely surprises me with how good or interesting it is, or when a company I love releases a new toy and I get to try it before almost anyone else.

However, there are many, many times when it feels more like being a book critic who has to review the latest Fifty Shades novel. “Again? Another one? And it’s as bad as all the previous ones? What can I even say about this? Will the publisher get angry if I describe the book (accurately) as terrible? What if it’s actually just mediocre and dull? What can I say that hasn’t been said before? What can I say that is true, and also interesting to read, and also won’t piss off the author, and also won’t make me fall asleep at my keyboard as I’m writing it?”

“Are you mad at me?” is one of the questions I have asked most often in every romantic relationship I’ve ever been in. It’s a relic of trauma, neural leftovers from a childhood where my dad being mad at me meant I was about to be shouted down into a triggered puddle of sludge. If you learn something is dangerous to you, dangerous to your wellbeing and your world as you know it, you’ll do your best to avoid that thing in future – and for me, it feels very, very dangerous for someone to be angry with me. Especially someone important to me. Especially if I don’t know whether they’re actually mad, and so the question hangs in the air like a raincloud threatening to burst open and pour.

It’s only been the past year or two that I’ve even felt comfortable referring to my childhood experiences of emotional abuse as abuse, as trauma. Prior to that, I didn’t have that language (or at least, didn’t feel able to claim it), and so I found myself unable to adequately explain why I kept asking partners “Are you mad at me?” The question became a Chinese finger trap with some of my more reactive partners: the more I pulled, the more painful the situation got. Their irritation level would creep up gradually with each iteration of the question, so that “Of course not!” became “No” which then became a gruff “I already told you: no.”

They didn’t understand that I wasn’t just asking out of some insecure curiosity (which, frankly, should’ve been alright too) – I was asking because the possibility of my partner being mad at me felt like a potentially world-ending risk. I was asking because the difference between “yes” and “no” was also the difference, in my body, between panic-inducing terror and happy relaxation. I was asking because I needed to know.

The flipside of this Chinese finger trap analogy is that if you want to escape the trap, the best way is to approach it gently and slowly, rather than yanking with your full fury. The gentlest way a partner can answer this question is to say some version of “No, not at all,” and to answer in that same way every time the question is asked (if indeed that is true). Paradoxically, the annoyance of being asked the question multiple times in one day is only likely to transpire if the question is answered with irritability. If it is treated as a normal, neutral, non-annoying question, and answered as such, then the asking becomes less and less urgent, and thus less and less frequent.

Impractical shoes have much less of a place in my life now than they did in my party-going, shots-drinking, wobble-home-at-2-a.m. youth. In fact, I almost never wear them anymore, except for when I’m having sex.

My spouse Matt and I share an interest in financial domination and “sugar dating” as kinks. I view those two interests as being two sides of one coin; the balance of power in our dynamic on any given day decides whether them buying me fancy things feels more like I’m a little girl being spoiled rotten by her daddy or an imperious queen being mollified with gifts by her loyal subject. As a result of these pervy interests, my collections of mid- to high-end bags, shoes, and lingerie have grown over the past couple years or so, to my femme delight.

Content note: This essay contains discussions of 13-year-olds being sexualized by other 13-year-olds, albeit in a way that was ostensibly consensual.

I was in the seventh grade the first time I saw a girl kiss another girl in real life – and she had been paid to do it.

Let me back up a bit. I went to a middle school that was located a couple blocks from Bessie’s Pizza, a convenience store that also had a giant pizza oven in the back and would sell slices of the most succulent, authentically Italian pizzas I’d ever tasted at that age. Bessie’s was the prime lunchtime destination for all the “cool kids,” and the kids who wanted to be cool. We’d trek over there in small groups to buy our slices of pie alongside chocolate treats, soda and Gatorade. Bessie herself presided over us, snapping furiously in Italian if we got too raucous in her store, which we often did.

You know, it’s funny – if someone asked me, I wouldn’t tend to say that Mean Girls is one of my all-time favorite movies, but it is one of the only movies that I still enjoy watching from start to finish regardless of how many times I’ve seen it before or how recently I’ve last seen it. I just don’t seem to get tired of it. It’s a masterwork.

One of the best things about this movie, in my view, is Rachel McAdams’s performance as popular teen queen Regina George. It is a luminescent, terrifying portrayal that absolutely jumps off the screen, right up there with Rosamund Pike’s conniving Amy in Gone Girl and even Jack Nicholson’s horrific turn in The Shining. Although it’s Lindsay Lohan’s Cady that we’re encouraged to empathize with throughout the film, and Cady’s story that we follow most closely as she rises through her new high school’s social ranks, Regina is the character who comes to mind for me immediately when I think about Mean Girls. Regina is the keystone of the entire story, the dictator who rules her high school’s social hierarchy, the beautiful, brilliant, blonde bully who makes the rules and punishes transgressors. Regina is the engine and the fuel of this story, practically from start to finish.

When I was 25, I went on a date with a cute boy from OkCupid named James (name changed). He was in my phone as “James Punnilingus” – and still is, to this day – because his dating profile contained a pun related to his passion for performing oral sex (hot). Obviously, I had high hopes about the date.

We went to my favorite restaurant for lunch, because he worked nights at a local TV station (also hot). I barely remember what we talked about, because he was a babe and kept making me laugh so hard that I snorted beer out my nose. At one point he mentioned that he’d gone to my alma mater, Ryerson, to study TV & radio (also also hot).

We had a good time, but he told me later that he was feeling polysaturated (polyamorous lingo for “too many women want to date me and I am only one man”), so we didn’t go out again.

HOWEVER.

Content notes: dentistry, nitrous oxide (“laughing gas”), marijuana, spanking, sadomasochism, addiction, death, anxiety, hypochondria, local anaesthetic.

I knew as soon as they slipped the heart rate monitor onto my finger that I was fucked. The machine beeped and numbers lit up: 98, 103, 105. They seemed to get higher the more I looked at them.

“Feeling a little anxious?” the hygienist asked.

Content note: This is a piece about weight, body image, anti-fatness, etc., and as such, it will touch on fat-shaming, calorie-counting, food/dieting, losing and gaining weight, anti-fat bias, etc. If that stuff is tricky or triggering for you (as it is for many of us), feel free to skip this one, in which case, I’m proud of you for knowing what you need and taking care of yourself. 💜

I don’t recall the first time I consciously thought “it’s bad to be fat.” That’s part of the problem, isn’t it? This shit starts early.

I remember my parents fretting about their weight, my dad going on the Bernstein diet, sticking to a regimented and restrictive menu of foods and going in for regular vitamin injections to get the nutrients his food wasn’t giving him. I remember eating cake and ice cream sometimes and feeling vaguely bad about it, the way I felt vaguely bad when I slept in til 1 p.m. or skipped class. I remember billboards and magazines, and my own mirror reflecting a very different image back at me.

Given how much of a pervert I am, I can’t believe how long it took me to realize I could get spanked with my own book. I mean, at this point it’s been more than two years since I received the initial book deal offer email, which said clearly that the tome would be a hardback. I guess I was a little distracted by the whole “holy shit, I’ve got a book deal” thing.

But when I mentioned to Matt that it had just occurred to me someone could spank me with my own book, they said, “Oh, I know.” They’d been thinking about it already. Classic Matt.

Content notes: semi-public sex, daddy dom/little girl language

My ex-girlfriend knelt on the carpeted floor in front of me at a post-Pride Parade party and looked up at me with her enormous doe eyes. On a cartoon character, the expression in those eyes may have read as “Please help me!” or “Please be nice to me!” but on this particular ex-girlfriend, I knew to read that expression as “Please let me go down on you!”

This moment was the culmination of all-night-long semi-flirty repartée about how we used to fuck and would maybe fuck again someday. While that’s not the type of thing I’d joke about with a cis male ex – mostly because he would almost certainly take it as an invitation – this ex-girlfriend and I did joke about it fairly often, largely because we were still part of the same close-knit friend group and it would’ve been weirder to not mention our shared history than to talk openly about it. However, just because she wasn’t a cis man didn’t mean she was immune to taking these jokes as invitations.

Content note: trauma / emotional abuse, panic, breakups, daddy dom/little girl language

They say memories live in our muscles and bones, stored up like the debris of life that accumulates in your closet. “The body keeps the score.” The body notices, feels, and remembers.

Last night around midnight, I began crying inconsolably, shoulders shaking, breath trembling, pillow thoroughly soaked. Looping in my head was a chorus of depression voices: “You’re garbage.” “Your partner’s going to leave you and then you’ll be alone forever.” “You don’t deserve love or happiness.” “What if you fuck it all up?”

Content notes: mentions of death

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“Do you come here often?”

It’s the cheesiest question, often the first question a horny stranger will ask you at a bar or a nightclub or – as was the case for me that night – in the heated swimming pool at the local sex club.

“We should watch that new show Sexy Beasts together,” Matt said. “It’s very demisexual.”

While it is not uncommon for us to describe particular people as “very demisexual” (e.g. “Wow, the host of the podcast I’m listening to just used the word ‘recalcitrant’ in casual conversation and I’m way more attracted to her now; god, I’m so demi”), it’s rare for me to hear a piece of media described this way, so I was intrigued.

Brief demisexuality explainer incase you don’t know what that word means: it’s an identity on the asexual spectrum. Demisexual people, like me, don’t develop sexual attraction until an emotional connection has formed, or at least until they feel like they know the person in question beyond a surface-level familiarity.

Content notes: spoilers for the 1999 movie Eyes Wide Shut; discussions of cuckolding, infidelity, and racism.

“Why did no one tell me Nicole Kidman and Tom Cruise made cuckolding porn together?!”

I often shout at the TV screen when I watch a movie while lightly blazed, and this was perhaps one of the better things I’ve ever shouted. This exclamation happened, of course, while my spouse and I were watching Stanley Kubrick’s 1999 masterpiece, Eyes Wide Shut.

Content notes: discussions of trauma, emotional abuse, non-consensual spanking, invalidation, and social media harassment; mentions of daddy dom/little girl roleplay and death threats

It feels weird to be a sex writer and still be scared to share stuff that’s “too” personal, “too” vulnerable.

Of course, everyone is entitled to their boundaries and their privacy, including sex writers. But this sense of protectiveness over my private life is relatively new for me. In my early twenties I regularly and happily recounted tales of my wildest wishes and hardest heartbreaks, my weird hookups and tumultuous relationships. It felt like – and was – a way to process what was happening to me, and what I was learning. It felt useful, and indeed, I got plenty of messages from people who told me that my intimate overshares helped them feel less alone, less broken.

This month, my partner gave me an assignment: I had to choose a sex/kink skill I wanted to get better at, put together a list of educational resources focused on that skill, and then write a short essay summarizing my findings and suggesting some potential future steps we could take together to improve my skill level in that area. I chose touchin’ balls. Here’s what I wrote.

Although I’ve received copious compliments on just about every blowjob I’ve ever given, when it comes to touching balls, my skills are lacking. (#Humblebrag, #sorrynotsorry.) Sure, I graze and stroke them here and there, and give them occasional attention with my lips and tongue, but for the most part, I’ve long been too nervous about hurting a partner to really go ham on those ‘nads.

However, in reading and watching numerous resources on scrotal stimulation, I’ve picked up a few new ideas. Here are some of the key findings that emerged in my research:

What if I told you there’s a movie that incorporates bondage, choking, costumes, crying, daddy doms, D/s, fear play, financial domination, hair-pulling, high heels, humiliation play, impact play, intoxication, knife play, objectification, predicaments, primal play, public sex, puppy play, roleplay, seduction, stripping, subspace, verbal degradation, voyeurism, and aftercare… and it’s not even a movie about kink?

Sounds far-fetched, I know. But it exists. And it’s fucking excellent.

(FYI, that paragraph above also serves as your list of content warnings for this essay. There will also be spoilers below.)

I recently finished reading Don’t Call It a Cult, Sarah Berman’s diligently reported book about NXIVM (pronounced like “Nexium”), a cult based in Albany, New York. Founded by pathological liar and arrogant shithead Keith Raniere (and that’s putting it charitably), this group used discourse about “self-actualization” and “self-development” to legitimize the increasingly wacky and abusive classes, rituals, and initiation activities they required entrants to participate in.

But they also used non-consensual hypnosis, which is pretty fucked up.

In her book, Berman gives a little history on neurolinguistic programming (NLP), a method of communication aimed at (among other things) controlling and influencing people through the use of sneaky, low-level hypnotic techniques in conversation, such as mirroring body language and verbally evoking specific emotions.

Some of my hypnokinky friends use NLP in consensually pervy ways, but NLP is also a calling card of almost every abuser I’ve ever heard of in the hypnokink community. It is so synonymous with non-consensual control that many classes on pickup artistry teach NLP techniques. (Anything the pickup artists are into is automatically deeply suspect to me.)

I minored in psychology when I went to journalism school, and while those teachings have been hugely helpful to me in my career (dissecting research studies, understanding psychosexual phenomena, etc.), they’ve perhaps been even more useful to me in my personal life.

I remember sitting in the back of a lecture hall one sleepy morning, having chosen that far-away seat on purpose so the professor wouldn’t see me scrolling through Reddit or Twitter. (Bad girl.) I looked up mid-lecture to find that the instructor was explaining the theory of multiple intelligences. My eyes widened and I switched tabs to my note-taking app, suddenly desperate to absorb what was being taught.

What I didn’t appreciate, at the time, was that this professor had a pretty leftist, intersectional, progressive view of what intelligence is and how it functions. I’d just thought she was lecturing about boring brain stuff (god, if I ever have to hear another goddamn explanation of what the amygdala does…), but I realized in that moment that she was imparting something much more useful: an entirely new way of thinking about a trait I considered of utmost importance.

See, I’d always been one of those snobs who prefers to date smart people, whatever the hell that even means. I even identified as sapiosexual for a time, which I now understand is a weirdly appropriative term that misidentifies an elitist, often classist and racist preference as a sexual orientation. But I’d had reason to question the simplicity of that viewpoint in recent years. For instance, I’d dated a few people in high school who had various combinations of ADD, ADHD, autism, and dyslexia, so I’d come to understand (far too late; mea culpa) that misspelled texts and showing up late to dates did not necessarily mean a person lacked intelligence or respectfulness. But I did not have a concrete, scientific way of thinking about this revelation until that lecture on multiple intelligences.

I had a romantic/sexy dream last night about a local improvisor/comedian who, in real life, has no idea who I am. This happens to me far too often, if I’m honest.

I know it’s boring to hear about other people’s dreams so I’ll be brief. We were seated beside each other at a low-lit dinner party, surrounded by people, but somehow we created a bubble of erotically-charged intimacy between us with a volley of flirty jokes and double entendres. He quirked a handsome eyebrow. I blushed, giggled, and ate my salad. He complimented my outfit, my body, in his hot British accent. I bit my lip and thought about fucking him in the kitchen, the bathroom, the back yard, anywhere. But instead we just sat there and flirted. At the end of the evening, we said good night, and I felt the familiar bidirectional pulse between heart and cunt that is too complex and wonderful to be adequately described by simple words like “excitement” and “arousal” and “infatuation.” I woke up flushed, turned on, and mildly miffed it wasn’t real.

It’s hilariously demisexual of me to have had essentially a sex dream that contained no sex, just conversation. But in truth, I think flirting often turns me on more than dirty talk, and sometimes even more than sexual touch, depending on whose touch it is. Flirting is a tease; it’s sexy because of what could be, not what is.

It (often) requires social finesse and fluidity, a form of intelligence I’ve always found impressive and wished came more easily to me. It (often) requires boldness, the ability to figure out what risks are appropriate to take and the wherewithal to take them. It (often) requires a split-second assessment of what the person you’re flirting with is likeliest to respond to, and what will get their panties wet versus make them get up and leave. The more I think about it, the more I suspect good flirting (the kind I consider good, anyway, which isn’t universal) is hot to me primarily because it’s an exercise in cleverness, confidence, and mastery of someone else’s mind.

The other night I was watching Bo Burnham’s new Netflix comedy special Inside with my spouse (highly highly highly recommend) when I suddenly shouted, “I’M SO DEMI FOR BO.” My spouse laughed because they knew exactly what that meant.

Here’s what it meant: I’m demisexual, meaning I don’t develop sexual attractions for people until and unless I have an emotional connection with them – but due to the paradoxical, parasocial nature of the internet, sometimes wires get crossed in my brain and I feel like I have an emotional connection to someone I have not, in fact, ever spoken to or even been in the same room as.

This is complicated because, being an online creator myself, I know for a fact that when people think they know you because they know your internet persona, they are usually wrong. It doesn’t matter how open you think someone is being online – there are always parts of them you don’t see. And that’s actually a good thing. As Bo points out several different ways in his special, the internet can be an addictive whirlpool of validation blended with devastation. I used to give nearly my whole self to the internet, but I don’t anymore. Some things really are too vulnerable, too personal to share, or just none of any strangers’ goddamn business. That’s valid as hell.

So the Bo I know is only a fraction of the real him. That’s how it is, and how it has to be. And yet, because I’ve been watching videos of him since I was about 17 years old, the demisexual part of my brain is like, “Hey, we know that guy!” which inevitably leads to a feeling of “Hey, we’re attracted to that guy!” which is when I take stock of the inner anguish of an unrequitable crush and yell mournfully at the TV, “I’M SO DEMI FOR BO.”

Content notes: discussions ofcuckolding porn, “cheating,” blowjobs/deep-throating/face-fucking, incest roleplay

Last night I bolted awake from some unsettling, half-remembered dream, and couldn’t get back to sleep again, so I tried watching some porn. Hey, why not?

In my hazy state, a lot of my normal “go-to’s” weren’t quite doing it for me. I was a few searches in when I happened upon a video by an amateur performer named DickForLily, entitled “business partner's wife sucks my cock while her husband plays racing.”

I’m writing a book for Laurence King Publishing right now called 200 Words to Help You Talk About Gender & Sexuality. It contains definitions of 200 words, ranging from “heterosexual” to “demigirl” to “polyamory” and beyond. Although the finished manuscript’s word count will total only 20,000 (100 words for each of the 200 definitions therein), it has proven to be an absurdly huge undertaking. How do you define concepts that make up people’s identities, communities, worldviews? How do you describe, in universalizable and comprehensible terms, what makes someone [insert marginalized identity here]?

The answer to these questions, mainly, is research. When writing about an identity I don’t hold myself, or a phenomenon I haven’t experienced firsthand, I’ve been diving into the scientific studies and personal essays and intimate blog posts where people discuss the ideas I am defining. I’ve been looking for key themes, motifs that arise again and again, and then condensing them into one small paragraph. It is not easy to do. It is weighty work, and I am taking it very seriously. My spouse Matt, who is queer and nonbinary, reads through my new chapters at the end of every work day and critiques the most minute of word choices, suggests additions or subtractions, offers alternate perspectives and resources to seek out. I make diligent notes, dive back into my research, and write some more.

There have been some days lately when I’ve intentionally chosen words I think will be easy to define, words with fairly straightforward definitions, like “gay” or “tucking” or “virgin.” It turns out that even writing these seemingly basic definitions is not as simple as it seems, especially since I’m trying to include a bit about the history of each word in its definition and, in many cases, an acknowledgment of the ways each term or concept has been critiqued or rejected by certain populations.

But there are also days when I think, “Hey, I have some spare mental energy today. Let’s do a hard one.” Yesterday was one such day. Yesterday I decided to try to define the word “gender.”

Recently my friend Brent asked me, on a Patreon bonus episode of our podcast Question Box, “What’s an unusual word or phrase you’ve typed into a porn site search bar?” I knew the answer immediately, because I’d searched something odd pretty recently: “typewriter.”

I was (and am) having a bit of a moment with regards to typewriters. I’d seen the documentary California Typewriter, which had sold me on the idea that a vintage manual clunker could tune up my creative process in significant ways. I’d instructed my finsub to buy me a bubblegum-pink Brother Deluxe 220 on eBay. I’d watched several ASMR-esque videos on YouTube of typewriter dealers clacking away on their wares to prove the keys still struck true.

And then, of course, because I’m a perv and I wonder about the sexual implications of just about any new idea I encounter, I searched “typewriter” on PornHub.

There wasn’t much to be found. One of the two results was utterly unrelated, and the other involved a woman being “stuck in a typewriter” although what she was actually stuck in was a washing machine (not sure how one could mix those two things up but okay). That’s why today I’m gonna write a little typewriter porn for you. ‘Cause why the hell not. I’ll include some clicky-clacky eye candy, too.

I’m reading the excellent book Straight: The Surprisingly Short History of Heterosexuality by Hanne Blank, and have arrived at the chapter about sex. Hallelujah.

One of the interesting lessons from this section of the book is that when the female orgasm went mainstream – i.e. when “marriage manuals” started instructing men to give a shit about more than just their own pleasure – the goal-of-all-goals immediately became simultaneous orgasm during penetrative sex. Because of course it did.

Blank notes in one section that this type of orgasm was euphemistically referred to as “true marriage” – as if no marriage could be legitimate, in the eyes of the church nor the eyes of society, if this achievement was not accomplished. Sure, yeah, that makes sense: assign a near-impossible task in an area of life where most people at the time know next-to-nothing, and give them only obliquely coded instructional books to guide them. Cool society ya got there.

While I’m glad female orgasms were acknowledged and semi-prioritized (albeit not enough and millennia too late), it seems ridiculous that “during PIV and simultaneously with one’s partner” was held up as the gold standard for women’s climaxes, considering that even today – when we have the benefit of information about the clitoris, countless sex position guides, and access to vibrators – achieving simultaneous orgasm is difficult. I mean, how many people do you know (who have PIV sex at least semi-regularly) who’ve ever even achieved it?

Hi friends! Apologies for the lack of a letter on Thursday, the day these usually go out. I was frantically packing 3 suitcases (!) for my return to Toronto after 6 months of staying in New York with my spouse.

I hope to get back to more substantive writing here soon, but for this week I thought I would share an example of an actual writing assignment that my spouse/dominant tasked me with this week. It’s not that I think it’s a particularly great piece of writing or anything – it’s not – but I do think it’s potentially instructive for other kinky couples, especially long-distance ones.

The assignment was as follows: “Pick 5-7 things (media, sex things, date ideas) you think we should do together over the phone once we’re apart and write up to 100 words about each of them.” The implication – not spoken or written, but known to both of us, I think – was that this task was assigned to me as a way of bridging the gap between being physically together and being far apart again. It’s always a difficult transition period, made all the more so in some ways when our time together was long enough that it felt like we were actually living together (and we essentially were).

Below is what I wrote; I hope this perhaps inspires you to think about difficulties you face in your relationship and the kinky-yet-intimate writing assignments that could potentially ease them in some way, if you’re inclined toward that kind of thing.

I often feel that kink is a mindset, perhaps even more than it’s an activity or an interest.

Let me explain. Once the “thought technology” of kink infects your brain, if you’re a certain type of nerd, you’ll start seeing it everywhere. I watch stand-up comedians and think about how they’re “topping” their audience for laughs, optimizing each joke to squeeze out maximal reactions, like a tickling top testing their tied-down partner’s limits with a feather duster. I watch politicians give speeches and note their verbal rhythms, perfectly attuned to how the human brain will hear and feel their words, like a masterful emotional sadism top. I watch couples flirting at restaurants or in parks and pick up on body language that spells out “dom” or “sub” or, occasionally, “closeted foot fetishist.”

Sometimes this paradigm is a way for me to avoid uncomfortable feelings – for instance, when watching a casually abusive romantic relationship in an old movie, I’ll sometimes assume/pretend the couple in question is actually in a D/s dynamic, if I’m just not feeling up to mentally processing the actual abuse on screen. (As a survivor of emotional abuse myself, sometimes I’m just like… nah.) I feel similarly about the Daniel Bedingfield song “All Your Attention.”

One of the oddest sexual attractions of my life occurred in a Value Village thrift store when I was 15.

I was perusing the aisles, scouting out cute vintage items, as I did on a near-weekly basis at that point. I looked at cowboy boots, silk scarves, cotton dresses. Vinyl records, cracked homewares, tattered paperbacks. Nothing in particular caught my eye.

Content note: This essay contains discussions of sexism in medicine, as well as (briefly) graphic descriptions of painful rough sex in porn that may or may not be fully consensual.

As I was lying here holed up in bed this morning for the 3rd day in a row with excruciating pain radiating through my neck, shoulders, arms, hands, hips, knees, and ankles, I stumbled across this article about a new study which found that women’s pain is not taken as seriously as men’s.

The article notes that during the study, “when male and female patients expressed the same amount of pain, observers viewed female patients' pain as less intense and more likely to benefit from psychotherapy versus medication as compared to men's pain, exposing a significant patient gender bias that could lead to disparities in treatments.” As I read this, I rolled my eyes, laughed, and thought, “YA THINK???”