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Will You Still Love Me Tomorrow?

Kate Sloan

The most romantic story I’ve ever heard is told to me in my aunt’s kitchen during a family party.

It’s shortly before the total solar eclipse of summer 2017. An older woman I hardly know – a distant relative by marriage – is sipping white wine on a barstool next to me, and we strike up a casual conversation. “My husband and I are headed down to Illinois to see the solar eclipse,” she announces breezily. “We’ve been planning this trip for almost 30 years!”

I furrow my brow. “What do you mean?”

I watch her eyes wander fondly to the nerdy, affable-looking guy currently fussing with a roast chicken he’s about to slide into the oven. “When I first met him, in the ’80s, a total solar eclipse had just happened, and he’s a big eclipse nerd, so he was there,” she tells me in a low, conspiratorial voice. “He said, ‘Hey, you should come with me to Illinois for the total solar eclipse in 2017. It’s going to be beautiful.'” She takes another sip of her wine. Her husband is catching none of this; he’s too busy making dinner. “We’d only been dating a few weeks,” she adds with a smile, “and now it’s decades later and we’re going!”

I’m floored. Shortly into a new relationship myself, I have no idea what would make someone so sure of a relationship so quickly that they would start making plans that far in the future. People breeze in and out of my life so easily, so suddenly; I can barely imagine believing a partner will still be around in a few weeks, let alone a few decades.

“Did that freak you out?” I ask, unable to contain myself. “That he asked you that, so soon into your relationship?”

She considers the question, and shrugs. “No, not really. I guess I just knew.”

Both of our eyes slide back over to her husband, and I can feel us wondering how he knew. How anyone knows a relationship is meant to last. It’s an impossible, unanswerable question, and one I desperately want an answer for.

Some heartbreaks are big, and some are small. That summer goes on to contain both for me. The first in the series comes when my boyfriend sleeps with someone else when we’ve only been dating for an intense, heady two weeks – without asking me, notifying me in advance, or seeming in any way to consider my feelings in this decision. I feel like the rug’s been ripped out from under me, but because we’ve agreed to be non-monogamous, I feel I have no right to express displeasure with him, even as my heart crumples in on itself.

But he’s not completely oblivious. Apparently sensing my misery, he texts me, “I was having this lovely daydream yesterday, of us together in a few years. You were more established as a writer, and you’d always bring me as your +1 to all the fancy events.”

This text comes in while I’m en route to a coffee shop, and I burst into tears on the street.

His near-immediate gravitation toward someone else, so soon after meeting me, has me feeling like he doesn’t want me anymore, or like our relationship is doomed. So to receive this explicit acknowledgment that he not only wants me now but thinks he’ll still want me in a few years is groundbreaking: a balm for my wounded heart. It hasn’t occurred to me yet to wonder if I still want to be with him in a few years, because women are socialized to desperately cling to any halfway-decent man who wants us, our own desire and comfort be damned.

“It made me feel really happy and safe to know that you think we’ll still be together years from now,” I tell him later. “That’s why I cried when I got that text.”

“I know,” he replies. “That’s why I sent it.”

But his daydream turns out to be an empty promise. When he breaks up with me a few months later, he offers dully by way of explanation, “The long-term potential I thought I saw isn’t actually there.” I gather my things and walk out his door with hot tears stinging my eyes, faced with the task of rewriting all those futures I thought he’d be a part of.

“My heart is fucking broken,” I write in my journal. “This makes me feel like I can never trust anyone again. Like even people who insist they love me and will take care of me, and who prove it for a while, cannot be trusted to stick around.”

My dating life, for a while, is haunted by the spectre of this man. Far from “seeing what happens” and “going with the flow,” I can’t maintain an interest in any person in the present because their presence in my future is not assured. I know, logically, that any relationship can end at any time for any reason, but still I long for the safety of a solid long-term commitment. Without that, I feel sad, adrift, and alone.

The shadow of that perceived betrayal weighs heavily on my next relationship, to my chagrin. “It’s like the two of you are in dialogue with each other,” I tell my new boyfriend thoughtfully over the phone, after relaying to him – in January – the details of my August breakup. I should be over it by now. I know that; I do. But that profound feeling of safe-and-then-suddenly-not-safe is still haunting my psychology, making me see danger where there is none.

See, this new relationship is, by all indications, safe as houses. Five days after my first date with this mysterious Twitter crush from New York, I’m telling him about the Hippo Campus concert I’ll be attending on my next trip to his city, and he asks, “Is someone going with you to that?”

“Nah, just me.” It hadn’t occurred to me to ask anyone. I don’t know any other Hippo Campus fans in real life, and certainly would never expect a friend to trek to another country just to see my favorite band play. “Do you want a date?” he asks, so casual, like this question isn’t a Big Fucking Deal.

“Haven’t you not even heard any of their music?” I ask, and he answers coolly, “I’ve got time.” And then he hops onto the Brooklyn Steel website and orders his ticket.

I can’t articulate how much this gesture means to me, and I worry that even if I could, it would scare him off. Because what he’s telling me with this simple $20 ticket purchase is: I like you enough to stay in your life for two months, at least. We’ve only spent a couple hours together so far, over coffee and kisses, and he’s already sold enough on me to bet we’ll want to dance together to a quartet of indie-pop boys two whole months from now. It’s funny how I’ll happily make plans with friends months in advance, but a new potential romantic partner tries to flip a couple calendar pages and I panic. There’s no way he’ll still be interested in me by then, I think, pathetically – but he’s already bought the ticket, so what can I do?

As those two months slide by, more and more hints emerge that maybe this boy plans to stick around. I tease him, “You’ve gotta charm my best friend if you ever meet them,” and he amends, “Hopefully when.” I tell him I know what color I’d use for him in my spreadsheet if we had sex, and he corrects me, “When, not if.” One night during a tearful phone call about Serious Emotional Stuff, I wipe my leaky eyes and say, “I’m sorry; I’m just not used to feeling this emotionally safe with someone,” and he answers fiercely, “Well, you can get used to it, because I’m not going anywhere.” I melt. I cry harder. I melt some more.

When the night of the concert comes, it’s even more special than I imagined it being when he first bought the ticket – because I’m not just going to a show with some guy I went on a date with once; I’m going to a show with someone I’ve been talking to on the phone almost every night, and slowly negotiating a delicious D/s dynamic with, and – whoops – falling in love with. He kisses me in the line outside the venue, holding my gaze steadily whenever our lips aren’t touching, and I imagine showing this tableau to me-from-two-months-ago. She’d be shocked he showed up at all, let alone showed up with this ferocious affection in his eyes.

Later that night, at a rooftop bar overlooking Brooklyn, he tells me he loves me for the first time. I say it back, and it’s devastatingly true. It’s so much not what I was expecting, and yet it’s exactly what I want.

He’s shown me even more, in the months since then, just how enduring he thinks our love will be. He’s bought plane tickets to Toronto a month in advance, and then showed up at my doorstep on the appointed day, handsome and smiling. He’s assigned me protocols that reach into the future, with more certainty than I can muster – enough certainty for the both of us. He’s bought tickets to conferences I’m attending, and exclaimed excitedly about all the things we’ll do there. Most of all, he’s told me, many nights, “I want to love you for a long time.” And though it’s impossible to guarantee such a thing, I feel more and more safe in his love every time he re-asserts this sentiment. We’re building something together, and I can see from his actions – not just his words – that he is serious about building it strong, building it well, building it to last.

When I used to complain to my therapist that no relationship felt safe to me because there was no certain promise of a future together, she’d ask, “But why do you need that to feel safe? Can’t you just enjoy the way things are right now, without worrying about what comes next?”

I can’t. Maybe it’s my anxiety, or my past heartbreaks, or just my temperament, but I can’t be fully satisfied with a futureless present, try as I might.

But fortunately, in this relationship, both the present and the future look pretty bright.

10 Thoughts From Really, Really Good Phone Sex

Kate Sloan

1. I can never quite identify when our casual catch-up conversations end and our phone sex begins. It’s not like in-person sex where beginnings are delineated by a particularly passionate kiss or a deliberately incendiary touch; it’s subtler than that. Sometimes I muse aloud from my bed, almost absentmindedly, “My skin is so soft tonight,” and his voice drops half an octave as he counters, “Oh yeah?” Sometimes we’re talking about Sex Things we’d like to do and they suddenly become Sex Things we are doing right now. Sometimes his voice just hits me the right way, renders me all melty-hot and small, and I make a squeaky submissive sound he recognizes, and we’re off to the races. I never remember quite how it began. It’s the least important detail of all, anyway.

2. I thought I didn’t like phone sex. I was resistant to those whispered words and breathy moans, paltry stand-ins for the embodied touches I craved. But I guess I just never knew anybody who could talk like this boy does.

It’s not like he’s really touching me; it’s not like he’s in the room with me. That would be an oversimplification of what this interaction feels like, what it means. “I can’t be there to fuck you physically,” he tells me one night, “but I try to take care of the psychological side of things.” That’s exactly what it is: he is fucking my brain, while I fuck my own body.

3. Identifying and understanding someone’s kinks is an underrated skillset. It’s one thing to know how someone likes to be fucked or choked or slapped; it’s quite another to know why they like these things, how these things make them feel, the words and phrases and images that flash through their mind when they’re getting off. It’s shockingly intimate to know a person that well.

And know me, he does. He keeps a “mental model” of me, he says, and updates it each time he learns something new about what gets me panting and dripping. He also keeps literal notes on me, in an app on his phone, because he is a nerd – but I think he barely refers to them anymore; he doesn’t need to. When you’ve fucked someone over the phone as many times as he has fucked me over the phone, and you really listen, you learn which phrases make them purr. You memorize when each particular moan will happen and what it denotes. You develop strategies for pushing them over the edge, and you sharpen your approach until it glimmers. Shockingly intimate, indeed.

4. But it’s not just his words. It’s his voice. So boyish and goofy when we’re joking around. So helpless and smitten when we’re confessing our love. So dark and oaky when he’s dominating me from afar. I could melt into it. I could dissolve in it. I often do.

5. “There is no one else I’d rather be in a long-distance relationship with,” I told him once. What I meant was: we are both verbal, and auditory, and kink-nerdy, and digitally savvy, and all those things combine to make a connection that can thrive through texting and phone calls and giggly FaceTime convos. Only a certain type of person could carry on this type of relationship in this electrically connective manner, and I’m so glad I found one in this world. Phone sex with him is not a stand-in for what I want. It is what I want. Or part of what I want, anyway.

6. The first time he wanted to slap me through the phone, I balked a little. Hurting myself, even at his behest, felt off somehow – a farcical facsimile of the thing we both really wanted: his hand arcing through the air again and again to redden my cheek. But I had trusted him with so much already and it made sense to trust him on this, too.

We experimented with different approaches, and, as two communication nerds are wont to do, eventually found what works best for us. He tells me to place my hand on my face. He tells me what intensity he wants these next impacts to be, on a scale from 1 to 10. And then, when we’re ready, he says: “Now.”

It always surprises me how readily my hand responds to him, as though possessed by his dark dominance from hundreds of miles away. Rationally, I know I could decide not to hit myself, if I didn’t want to do it. But I want to do it. So I always do. And it tugs me down into subspace almost as fast as his slaps do when he is there to give them.

7. We sometimes use the word “snowglobey” to describe time we spend together. It’s that feeling when you and your sweetheart are locked in a close moment, fleetingly frozen, and nothing outside your connection seems to exist. Time stretches endlessly, and it’s also over before you know it. You’re insulated. Embroiled. Snowglobey.

I have a bad habit of checking my phone when I’m supposed to be focusing on other things (these days, don’t we all?) but my mind doesn’t wander when his voice is fucking me. I forget that Twitter and Facebook and Slack exist. You only know what a big deal that is if you, too, live a phone-focused life. If you do, then you know it is a huge deal.

What a gift to give someone: some distraction-free minutes of pleasure, riveting and riveted. What a beautiful gift my love gives to me when he weaves stories so absorbing, I forget my body ever knew anything but bliss.

8. He murmurs filthy things about what he would do to me if he was here, but – vitally – he also tells me what to do to myself, right now.

He chooses my sex toys for me, and decides when each can come into play. He tells me how to use them: “Harder.” “Faster.” “Deeper.” He can tell how well I’m following his directions by the sounds I make. “Deeper than that. Almost. There you go.” It’s his mastery of me, as much as his dominant directives, that renders me a submissive puddle for him. I always do what he says, because if I don’t, he will know – and if I do, I will come. He will make sure that I do.

9. You would think that the orgasms would feel the way they do when I jerk off: quick, easy, small, predictable, perfunctory.

They don’t. They feel the way they do when he fucks me IRL: momentous and monumental, never quite expected, knocking me over like a wave. Afterwards, I lie there, cunt pulsing, breath slowing, all the energy and stress drained out of me. I listen to the rhythms of his voice and his breath, syncing with mine, floating back to earth, and I feel a peace and a connection I only ever previously knew while curled up against someone’s chest after they fucked the life out of me. I never knew I could get here without touching him at all. But here we are.

10. We learned pretty quickly that aftercare matters, even for phone sex. Saying good night just after orgasm left me as cold and alone as I’d be if one of us rolled over after sex, said “See ya,” and took off. My logical brain posited, “It’s just phone sex; it can’t need as much aftercare as an in-person kink scene does, because it can’t be as intense!” But it can be, and it often is, and aftercare is as important as ever.

We catch our breaths. We whisper I-love-you’s. We lie in bed sighing contentedly and giggling like goons. We describe how we would touch each other if we were together, and it feels almost real: fingertips brushing along heated skin. We find our way back to the world outside our little snowglobe. That world is just as harsh and unpredictable as ever, but I feel strengthened by the love I’ve given and received. Like a hot cup of coffee, my love emboldens me, refuels me, warms me right through.

There was a time when I thought I didn’t like phone sex. I wish I could lean back through time to that past version of me and tell her: “Just you wait.”

25 Amazing Sexual Experiences I Had At Age 25

Kate Sloan

I’m 26 today, babes! The past few years have been good to me, sex-wise: I got real slutty at age 23, learned a lot about my kinks and relationship style at 24, and settled into a more confident sexual existence at 25. To celebrate this minor milestone, here’s a list of 25 amazing sexual experiences I had while I was 25!

1. Dated a sadist. Despite identifying as a masochist for a few years, it wasn’t until just after my 25th birthday that I started seeing someone who self-identified as a sadist. I got spanked/slapped/scratched a lot in that relationship and it was great!

2. Got tied up. Rope bondage is a trip! I’ve dated two different rope aficionados within the past year, and playing with them showed me that being a rope bottom gets me real subspacey real fast. All that pressure, slowness, and focus puts me into a meditative space that’s unlike almost anything else I’ve experienced.

3. Pegged someone. I didn’t think I would like it, but I did. Innnteresting!

4. Used a blowjob mirror. I’ve been reviewing sex toys for over six years and this was one of the most terrifying toys I’ve tested, though it was also supremely satisfying and fun.

5. Experimented with “forced orgasm” play. I tried this with a few different partners and it typically involved them strapping me down and using a strong vibe on me until I couldn’t help but come. Very fun, would recommend!

6. Demo-bottomed for a spanking workshop. I took my dress off in front of a bunch of strangers and got my ass beat, which was… not as nervewracking as I thought it was gonna be. Maybe I have a teensy exhibitionist streak?

7. Dated a daddy dom. A couple of them, actually. DD/lg has been a fixture of my perv-brain for a few years but this was the first year when I actually tried it with real-life partners, and goddd, I love it.

8. Got a professional erotic massage. And actually had an orgasm from it, which I wasn’t expecting! It happened a few days after a breakup, which made it feel even more healing and necessary.

9. Fucked in an alley. I’d made out in many alleys before. I’d gotten spanked in a couple of alleys. This was the first year I actually had sex in an alley. It was lovely.

10. Had sex in my own place. I moved out of my parents’ house last September, and while I haven’t had a ton of sex in my own bedroom since then (tending, instead, to bang at partners’ houses or a local sex club), it was nice to christen my own space with sexual fluids ASAP. A real adulthood milestone!

11. Went to a sex tradeshow as foreplay. When you and your FWB are both huge sex toy nerds, there are few better pre-sex activities than trawling a tradeshow to see what’s new and hot. I bought a vibe and an impact implement, we flirted and giggled and made bad jokes, and then we had incredible sex at a club. A+ day, 10/10, would do again.

12. Got collared. Collars have been an important kink symbol to me for a long time but I’d never had one that was linked to a specific partner and made me “theirs.” My Sir had never collared anyone before me, either, so it was a super special thing for both of us when he put a collar on me in a Brooklyn hotel room just before we went to see my favorite band and exchanged our first I-love-you’s. So romantic!

13. Tried knifeplay. My pal Dick Wound is a hell of a knife top, so we negotiated some scenes so I could lightly explore my burgeoning interest in knives. It was scary, but in a safe, fun, consensual way. Oh, and a hot way. That, too.

14. Got spanked with a lightsaber. And also a butcher’s cleaver. (Which one would you guess hurt more?)

15. Did educational cam shows. I’ve long offered cam shows of the typically titillating variety, but this year I had a client who genuinely wanted to learn about vulvovaginal anatomy, so I got to patiently demonstrate and explain how I touch myself. Such a fun time!

16. Had a sugar daddy. This was a specific flavor of submission I had never sampled before, and wow, it was exhilarating. Money is so tied up in our personal psychology that I found it was easy to make it sexy, even though I’d never viewed it that way before.

17. Had actually good phone sex. Um, shout-out to people who have a way with dirty talk, because a) I sure don’t, and b) they can make me come really hard. Enough said.

18. Finally had sex with someone after a whole month of only sexting and phone sex. Love a good slow burn, am I right? It turns out you can fuck someone a whole lot better if you have a month’s worth of their sexy communiqué to refer to.

19. Shined a partner’s shoes. I will write about this in more detail when my head stops spinning from the incredible, meditative subspace it put me into. Neither of us had tried bootblacking in any context before, and once we did it together, we knew immediately that we liked it a lot.

20. Played with my wink kink more deliberately. Being winked at, in the right context, has long turned me on, but I’ve rarely had partners who knew how to harness that power to their advantage. My current boyfriend sure does, though. Winking as flirting, winking as foreplay, winking as a hypnotic induction… Woof.

21. Got hypnotized. A whole bunch. Ohhh, it’s so relaxing and hot. I love it.

22. Gave a BJ purely for my own pleasure. This experiment was inspired by my friend Caitlin K. Roberts and a Masters and Johnson concept she taught me about, “sensate focus.” It’s the practice of touching someone else for your own tactile enjoyment, and it can be transformative. I’d never given a blowjob quite like this before, and it really shifted my perspective on oral sex in general!

23. Sucked a dick through a glory hole. Granted, it’s not quite the Full Glory Hole Experience™ if you know exactly whose dick you’re sucking (or at least, I’m sure some purists would argue that), but I was still glad I got to try it. It’s been a fantasy of mine for a long time.

24. Received electrostimulation. I wasn’t sure how I would feel about getting painfully zapped with a Neon Wand, but, like many other forms of kinky pain, it made me subspacey and happy. And I’ll never forget how gleeful I got watching my boyfriend painstakingly try out each attachment on his own arm at various different settings to make sure he knew what he’d be inflicting on me before he did it. Swoon-o-rama.

25. Got “treated for hysteria,” i.e. did a medical-play scene centered around the Victorian notion of “female hysteria” being curable by manual and mechanical clitoral stimulation until “hysterical paroxysm.” The image of my boyfriend in a vaguely doctor-esque white T-shirt telling me, “That’s right, Kate, let go, let it happen” while holding a Doxy to my clit is forever burned into my brain…

What’s the most amazing thing you did when you were 25?

Do You Have a “Type”?

Kate Sloan

“You should date this guy,” my friend said, forwarding me a screenshot of someone they’d encountered on Tinder. “He’s totally your type.”

I stared at the picture, trying to see what my friend saw. The dude was scrawny, bespectacled, and looked like he’d probably make an obscure Sondheim reference in the same breath as telling you why your favorite Pokémon’s stats sucked. Yep. Definitely my type.

Curious, I took to the internet. “What kind of person do you think I’ll end up with?” I queried my Facebook friends. The answers were very interesting indeed.

“Good sense of humor? Which I guess is subjective, but someone who is good with joking around and not making asshole jokes and stuff. Someone who’s passionate about some hobby/job/pastime. Not necessarily something nerdy, but maybe.” -my friend Dan, who’s known me for a few years

My first girlfriend was an improvisor, and I’ve been drawn to improv weirdos ever since. There is just something about a person who can not only make you laugh, but can do so with a quick wit and a theatrical committedness that dials their jokes up to eleven. Being on a competitive improv team for a few years saddled me with some of the most intense crushes of my life, simply because seeing people be that funny, that fast and that often, is bound to give you Feelingz about at least some of them.

That first girlfriend also cursed me with a permanent attraction to purple fauxhawks, squeaky laughs, and – most crucially and most enduringly – puns. I practiced my punniness to impress her, and now, all these years later, wordplay still makes my ears perk up. If you can outpun me with aplomb, I probably want to kiss you.

“Somebody intelligent, who has a working knowledge of something you’ll develop a passion for after you meet them (you’ll teach them about something you know lots about, like theatre or something, and they’ll teach you about the new interest). Somebody calm/level-headed who isn’t drawn into an argument easily.” -Max, my brother

My first serious boyfriend was a game developer, and ever since that years-long romance, I’ve been hopelessly attracted to other developers of games and apps. If you can ramble my ear off about code, interactive narrative, and the evolution of iOS, I’ll have very little idea what you’re talking about, but I’ll probably wanna listen anyway. Especially if I already think you’re cute.

This proclivity got so bad at one point that I would start flirting with someone and only find out after the fact that they were a game dev. “Of course you are,” I’d say, smacking myself in the forehead. I could not escape the devs!

I was mystified by this for a long time, until a game-dev friend of mine offered a potential explanation. He said I’m attracted to nerds, but especially creative nerds – and software development is where hard-nosed geekiness crosses paths with starry-eyed dreaminess. To make a good game or app, you gotta have both imaginative vision and nerdy know-how. It makes a lot of sense to me now why I’m attracted to people in this career so frequently.

“They will be laugh-out-loud funny, have empathy out the wazoo, be a good listener, and spontaneous. Funny is so important. I think a unique sense of humour is big too, and owning their own quirks.” -my friend Georgia, who’s known me for 10+ years

When pondering whether or not I have a “type,” the phase “charismatic nerd” kept floating through my consciousness. It’s really the most succinct and accurate description of the people I’ve dated. My physical preferences have shifted over time, and usually haven’t been all that important to me – but charisma and nerdiness have endured as crucial qualities in all my crushes.

See, I love the zany zeal that characterizes nerds – their no-chill enthusiasm for whatever captivates them, and the ways that passion can translate to sex and dating. But while I find some nerds’ shyness and awkwardness endearing, it feels too familiar to my dorky heart; I tend to enjoy dating people more outgoing and socially smooth than me, because they pull me out of my introverted shell and take me on adventures.

S. Bear Bergman says you should date “someone who is similar enough to you to make you feel comfortable, but different enough from you to make the hairs on the back of your neck stand up.” Nerdiness sets me at ease. Charisma sets my nerve endings on fire.

“I mean, they’d need to love BJs and you’d need to have good sex with them, but I feel like as long as they weren’t selfish dickwads in bed, you’d be able to have good sex with them. Like, obviously you have your preferences, but I feel like your sexual priorities are a little more mutable than the things you’d need from their personality. So if they were amazingly funny/supportive/creative and willing to learn (because they’re supportive of your pleasure) then you’d be happy to do the work to make sure y’all were having good sex.” -my best friend Bex

Last year, I was telling my then-boyfriend about a man I’d previously been in love with, and he said, “Why did you fall in love with him? Wasn’t he vanilla?”

It struck me as an odd question, because at the time that all that shit went down, someone’s kink orientation didn’t really enter into my vetting process vis-à-vis crushes. If they were smart, funny, feminist, enthusiastic, and kind, I figured great sex could come later. Or I could settle for pretty-good sex. Or we’d figure it out when we got there. I dunno, man.

These days, though, I lean toward viewing my submissive identity as integral to my attractions. Someone can capture my attention by being a little dominant when otherwise I might’ve skipped over them. Admissions of risk-aware sadism or daddy-esque predilections get my blood pumping. I consider kink compatibility alongside humor, temperament, and lifestyle when deciding how deep to wade into a new crush.

But I still get all swoony for mega-vanilla people sometimes. Hey, you can’t win ’em all.

“Smart. Open-minded. Probably a goof or you’ll get bored, let’s be real.” –Sofi, who is a literal matchmaker for a living

Ultimately, the qualities that draw you to someone, and keep you interested in them, are to some degree ineffable. You can write out what you think is the precise formula of your attractions, but you can always prove yourself wrong.

All my major crushes have shifted my own perceptions of my “type” in some way. I never knew I could love an extrovert until I did; I wasn’t sure I could fall for a bald guy or a short guy or a vegan guy until I did; I’ve dated people older than I thought I ever would, younger, louder, quieter, farther away. They’ve probably all had some kernel of something in common – some clever glimmer, some magnetic tenderness – but it’s hard to see their similarities at a glance. If you put ’em all in a lineup, they’d look like a pretty disparate crew.

I love that about attraction, though. I love never knowing who I’ll want next, and why. It reminds me that life is a wild ride and there’s no use in trying to predict anything. Just enjoy it while you’re on it.

Do you have a “type”? How do you feel about it?

What Makes Bad Sex So Bad?

Kate Sloan

I’ve been a sex nerd for a long, long time, y’all. One of the ways this manifested early in my life was subscribing to the Bad_Sex community on LiveJournal.

At the time, I didn’t give much critical thought to why these stories fascinated me so much. But in retrospect, I think they gave me a sense of perspective about sex that I was missing at that time, as a naive virgin whose main understanding of sex came from flowery erotica stories and slick MMORPG cybersex. When the sex media you consume is all smooth ‘n’ hot, it’s easy to overlook how often real-life sex is boring, confusing, unsatisfying, or straight-up bad.

Let me be clear here: I am not talking about sex that’s bad from a consent perspective, i.e. rape, coerced sex, and so on. That is a whole other kettle of fish, obviously hugely problematic in different ways and for different reasons. I am talking about sex where consent is freely and mutually given, that turns out to be bad due to other factors. It happens, and I think we don’t talk about it enough, leaving the young or inexperienced among us with unrealistic expectations of sex as effortlessly perfect and magical.

So I was excited when Lily Wilson reached out to me to tell me about her new book, In the Glow of the Lavalamp: Stories of Bad Sex and Other Misfortunes. It’s a series of short, funny bad-sex tales. Flipping through Lily’s book inspired me to reflect on some of my own memories of bad sex…

The first time I ever had penetrative sex was a mess. Me and a cute lesbian FWB decided our foreplay should be scissoring, since that’s, I guess, the quintessential girl-on-girl act. (Or at least, it was, in the minds of two 16-year-old baby queers who watched too much The L Word.) She’d just purchased some blueberry cheesecake-flavored lube and, having never used lube before, decided one full handful each was the proper amount. We anointed our vulvas with this sticky elixir and then rubbed them together until our muscles ached and the slippery squelching sounds made us giggle so profusely we had to stop.

Next we attempted the centerpiece of our evening: strap-on sex. She suited up in her new harness and slipped a smallish grey silicone dildo through the O-ring. We tried one position, and then another, and another, but no matter what we tried, we couldn’t figure out how to get the dildo into me without hurting me. I’d already used a bigger dildo on myself plenty of times so the hymen hypothesis didn’t check out; it was seemingly an issue of angle and awkwardness.

Finally, we settled on the “cowgirl” position: me on top, astride my pal. I ground down against her for many minutes, looking for an angle that would give me any pleasure whatsoever, but I couldn’t find one. She seemed to be enjoying it, though, so I kept at it… for half an hour. We bucked and writhed in near-silence, just breathing and grunting and sweating. So much sweating. I literally dripped sweat onto her. I felt disgusting. But I couldn’t stop, because she was… into it? Maybe? I couldn’t tell.

When I finally collapsed in exhaustion beside her, I asked, “Did you come?” and she replied, totally mystified, “No. Did you?” Of course, I hadn’t. And the window for any further pleasure had closed, both of us being too overexerted to move, let alone get each other off. We fell into a deep, unsatisfied slumber, in a puddle of sweat, saccharine lube, and bemused disappointment.

The last truly bad sex I had happened last summer, 5 days after a breakup, which should’ve been my first clue it was ill-advised. A beardy Tinder bro talked my ear off at a bar for an hour about his career ambitions, his creative vocations, places he’d been, girls he’d fucked. He mocked the food I ordered, expressed zero sympathy when I mentioned I’d just been through a difficult split, and asked me literally nothing about myself.

And yet, somehow, I decided to go back to his apartment with him. I am not proud.

We smoked weed in his humid attic apartment and launched into messy makeouts, no romance or pretense whatsoever. He awkwardly tried to pin me down because I’d mentioned being submissive, but it felt hollow, perhaps because I’d dated an ardently dominant kinkster so recently and was still sad about it. He went down on me and unleashed a pointy, flicky tongue on my hypersensitive clit, causing me to squirm away and offer breathy suggestions like, “Can you do that slower and softer?” or “Can you focus on the side of my clit instead of right on it?” but he seemed confused by these directives and just kept at it.

After a few more minutes of this, I gave up and tried to transition things into good ol’-fashioned fucking, but neither of us seemed that enthused about his dick being inside me. Finally, he finished himself off on my chest and belly while we kissed. As we laid there in the smoky darkness afterward, he asked, “Did you come?” and I narrowly resisted the urge to exclaim, “LOL, nah, bro.”

Unsurprisingly, what both these bad-sex stories have in common is a lack of assertiveness and communication. There are good reasons for that: the culture we live in encourages us to keep quiet about sex, and also encourages female and feminine folks, in particular, to downplay our needs and focus on making other people happy. I don’t regret these experiences, and my other forays into bad sex, because I’ve learned a lot from every one of those encounters – but I like to think I’d be better at avoiding situations like these nowadays.

Alana Massey once wrote, in an essay about bad first dates, “This life is short and wild and precious, and people are spending way too much time on first dates that they need to skedaddle on out of as soon as they know things are heading south.” I think this sentiment applies to bad sex, too – though leaving any romantic or sexual interaction midway through is, obviously, easier said than done.

Bonus: here’s an interview I did with Lily Wilson, the author of In the Glow of the Lavalamp: Stories of Bad Sex and Other Misfortunes!

Kate Sloan: What made you want to write a book about bad sex?

Lily Wilson: I’d written a story about an incident that was hilariously bad. When I shared it, people began coming out of the woodwork saying, “OH! You won’t believe what happened to me!” They’d tell me their own stories. Many of these were funny. Bad sex happens more frequently than most people imagine; in fact, there’s a universal aspect to it. But we don’t often talk about it. An activity that involves so many complex interactions, so many things that can’t be controlled, is bound to go wrong some of the time. I began to collect the stories and get permission to write them down. They aren’t always funny, but I do love the humor – that’s what makes the disasters bearable.

KS: Assuming we’re talking about sex that is consensual and not coerced, what makes sex “bad”?

LW: Two categories of things can make it bad: 1) stuff that is out of the control of either participant, and 2) choices the participants make. Category One includes things like disasters: the roof falling in on top of you, a giant rat pouncing on the bed… Also in this category would be like illness, accidents, interruptions, that sort of thing. These stories are usually funny, at least in retrospect.

Category Two is more complicated; it covers choices the participants make. Mismatched desires and expectations are behind a lot of bad sex. If both people are not honest about what they want, there’s a strong possibility the sex will be lousy. If person A wants roleplaying, costumes, and trapezes, and person B wants something more basic, and either person fails to communicate, this is not going to go well, probably for either of them. Sometimes people want connection so badly they stifle their needs and desires and attempt to settle for whatever is on offer. Like, OK, I will do y and z, and hope that I can at least have a minute or two of j and k. This approach generally does not produce a happy ending.

Category Two also includes the degree to which each partner cares about the experience of the other. Most of us have been with someone who was completely oblivious to or unconcerned with how the sex was for us… It is very difficult to have a good experience with such a person.

KS: What’s your #1 piece of advice for avoiding bad sex?

LW: Communicate! Make sure your expectations are compatible. Two people don’t have to want exactly the same thing, but it’s important that your expectations don’t nullify theirs, and their expectations don’t make yours impossible to fulfill. Make sure your partner cares about how the experience is for you. That sounds almost too basic to bother stating it, but there are an astounding number of people in the world who seem to be unaware of/uninterested in what their partner experiences. You get to say “No, thank you” to such people.

Thanks so much to Lily for doing this interview and for writing such an interesting book! You can buy it on Kobo or check it out on Amazon here.

Heads up: this post was sponsored, and as always, all opinions and writing (save for Lily’s answers to my questions) are my own.