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.

6 Big Things I’ve Learned From 6 Years of Sex Blogging

Kate Sloan

Oh wow: this blog is six years old today. That is unbelievable to me. When I started Girly Juice, I thought it’d be a fun summer project. I never envisioned it’d still be going strong years later, a major source of professional opportunities, social connections, income, and glee.

It’s been a major source of self-revelation, too. Here are six big things I’ve learned about myself, my sexuality, and my approach to relationships in the years I’ve been writing here at Girly Juice dot net…

1. I’m kinky as fuck. When I started blogging, I identified pretty squarely as vanilla. I had submissive fantasies occasionally, but figured they were just fantasies – not anything I’d want to try in real life.

However, two and a half years into writing this blog, I ended my very vanilla long-term relationship, and started exploring other avenues – at first, just in fantasy, and later, in reality. I tried things out with a couple of domly FWBs, dated some doms who helped me see in myself the submissive cutie they saw in me, and learned more about what being a “good girl” means to me.

I still suffer from “impervster syndrome” from time to time, feeling like I’m too kinky for vanilla folks and too vanilla for (some) kinky folks – but for the most part, I feel secure in my kinky identity. And I’m looking forward to exploring new kinks for a long time to come!

2. I’m non-monogamous. At the start of my blogging journey, I was in a long-term monogamous relationship, and was very happy and in love. But as time went on, I started noticing twinges of dissatisfaction. It had nothing to do with my partner – I adored him, felt blissfully supported by him, and was satisfied with our relationship in all but one dimension. Monogamous strictures made me feel owned and confined – and not in the fun, kinky ways!

Though we experimented with low levels of don’t-ask-don’t-tell non-monogamy in that relationship, it was clear that we were both compromising past our comfort levels, and that it wasn’t going to work long-term. We parted ways amicably, for this reason among others, and I started pondering what I wanted from my future relationships, vis-à-vis non-monogamy.

In the years since then, I’ve experimented with lots of different relationship structures: open relationships, hierarchical and non-hierarchical polyamory, solo poly, casual sluttiness, less-casual sluttiness. Right now, I feel like non-hierarchical poly is the best fit with my approach to dating and my interpersonal ethics. But, as with most of this stuff, I’m open to seeing how that evolves in the future.

3. A-spot stimulation makes me come a lot. I’ve written plenty about the A-spot (a.k.a. anterior fornix) over the years, after discovering – mostly through the use of sex toys – that it’s fairly key to my orgasmic process.

It’s been fun to teach various partners about this spot, and watch them light up when they figure out how to stimulate it. It’s been even more gratifying, however, to receive countless emails and tweets from people who didn’t know they liked A-spot stimulation until they read my articles about it. I never shut up about this spot because I don’t want anyone to feel like their body is broken or weird, like I used to!

4. You gotta ask for what you want. I’m great at telling other people to ask for what they want. I’m great at journaling about what I want, telling my friends what I want from my partners, and whining about how I don’t have what I want. I have historically been less great about actually asking partners for what I want.

This can be anything from “I want you to fuck me deeper and harder” to “I want you to answer my texts in a more timely manner.” Asking for things can feel embarrassingly unchill, but really, it’s the only way to get the satisfying romantic and sexual relationships you desire and deserve. I keep learning this in new ways all the time and it serves me so well when I manage to do it.

5. I prefer quality over quantity when it comes to sex and relationships.

Okay, some caveats here. First off, it’s possible to be slutty and/or dating lots of people and have all of those connections be high-quality, healthy, and wonderful. I know people who manage it. Kudos to them! Secondly, for some people, having lots of partners is their idea of a high-quality romantic/sexual life, and that’s A-OK too. If your sex life makes you happy, I applaud you and celebrate it with you!

However, I went through a “slut phase” and came out the other side realizing having a lot of romantic/sexual connections at once isn’t really a good fit for my particular brain and relationship style. Same with casual sex and one-night stands. The way those types of connections have functioned in my life, they don’t offer me the depth, support, and consistency I’ve discovered I crave. I’m suuuper glad I went through a slutty chapter of life, because it taught me a lot, but that’s not where I’m at anymore, and that’s fine!

My current poly situation looks like this: a long-distance boyfriend I talk to every day and have a super intimate relationship with; a local, casual, somewhat romantic partner I see on occasion for rope bondage and giggles; and a highly casual but still much-adored friend with benefits who I fuck about once a month. My emotional and sexual needs feel pretty well taken care of, and it’s so nice!

6. Anything can change at any time. You can develop new kinks, or lose interest in old ones. You can have a sudden, radical shift in what you want out of your relationships. You can learn new ways to orgasm, and get bored of your former failsafe methods. You can notice strong feelings for a new person, or abruptly lose interest in someone you thought you’d love forever. You can think you know what you need, and then realize you need something totally different.

I have “this too shall pass” tattooed on my inner wrists to remind me that everything is ephemeral. When you truly, deeply know and believe that, you develop a Zen-like appreciation for the good things in your life at any given time, knowing full well that they might not always be there. It sounds bleak, but it’s actually liberating – uplifting, even. There are things that bring you pleasure and joy now, and there will be more things like that in the future, and they might not always be the same things, but that’s fine. Pleasure springs eternal. Isn’t that lovely?!

What have you learned about your sexuality and approach to relationships in the past few years?

Review: We-Vibe Sync

Kate Sloan

There comes a moment in any sex toy nerd’s life when they discover a non-standard use for a toy, and feel like a goddamn genius. Epiphora conjured hands-free orgasms with the Dusk; Bex first told me about putting an inside-out Tenga Egg over the head of a Hitachi for some added texture; and as for me, I’ve used the We-Vibe Sync for kink. (Hey, it even rhymes!)

How, you ask? Let me explain by first taking you back to a night sometime in late 2015. I’m pinned beneath my domly then-fuckbuddy in his big soft bed. He’s fucking me, and it feels fantastic, but without some clit stimulation, it’s not gonna get me anywhere. I snake my hand down between us to rub my clit, but he barks, “Did I say you could use your hand, little one?”

It’s true, he didn’t. And it’s frustrating for both of us that I have to use my hand: kinks-wise, I’d rather have my arms pinned over my head, and he’d prefer us in that pose, too. But without clit stim, orgasm is a sad impossibility for me. We eventually settle on a compromise: we squish my We-Vibe Tango between us, so it stays put beside my clit as he holds me down and fucks me. It works well enough – okay, it works great, and I come all over his cock, panting and mewling – but it’s a flawed system. Neither of us can easily or quickly adjust the vibration strength, and our pelvises have to remain perfectly flush to keep the vibe where it needs to stay.

Enter the We-Vibe Sync. It’s been over two years and I’m not seeing that fuckbuddy anymore, but other domly princes have come along, and the Sync has been there for us. It’s my hands-free solution to the problem of the princess who needs clit stim to come, but wants to feel hopelessly trapped beneath her darling.

The Sync boasts another feature ideal for kink: the app through which it can be controlled via Bluetooth. Whether you and your beau are oceans apart or they’re sitting beside you on the sofa, they can control your We-Vibe using their phone. The app allows you to manipulate several pre-programmed modes, raising or lowering the strength of the two individual motors with a swipe of a finger – or you can create your own modes, set the vibe to respond to the bassy thrum of music or sound, or use the “touch” mode to tap and swipe your partner into ecstasy.

The novelty factor of this app cannot be oversold. You can deny your partner clitoral stimulation while thrumming on their G-spot to tease them into a frenzy. You can rub your phone screen like you’d rub their actual clit, and coolly watch them squirm from across the room. You can send them a message in Morse code via vibration on their bits. The possibilities are infinite, and could be very, very evil, in the best possible way.

You could also – I suppose – use the Sync in the way We-Vibes are traditionally meant to be used: to provide extra stimulation during presumably-vanilla peen-in-vag sex. Its internal arm is more flared and textured than that on the Unite, so it stays in place better. And the Sync has two hinges between its internal and external arms, allowing you to adjust it to fit your body, unlike any other couples’ vibe in history. Amaze!

I find those hinges useful when I’m using the toy solo, too. Some days, my clit wants more pressure; some days, it wants less. I can widen or tighten the Sync’s angle to get the exact right amount of clit pressure at any given moment, and to make sure the clit arm actually stays on my clit. It’s genius.

Beware, though, that these hinges are prone to breaking if you drop the toy or pull it wider too harshly. I’ve worked at two different sex shops and the Sync floor models at both were broken by overzealous customers and/or salespeople by accident. When the hinges snapped, so, too, did the connection between the two arms’ motors – so not only did the toy flop uselessly like a deflated boner, but it also no longer vibrated in the internal arm. Be careful with your Sync!

Getting back to this toy’s good points, though, here’s the major thing that makes the Sync better than any other couples’ vibe on the market: DAT MOTOR. For years I’ve wondered why We-Vibe’s flagship toys’ motors were so weak and buzzy while their solo vibes were satisfyingly rumbly. Now, at long last, they’ve put a Tango-esque motor in a couples’ toy. The internal arm is still buzzy and kinda useless to me, but that clitoral arm is every bit as rumbly as I need it to be. It brings me to deep, satisfying orgasms, and doesn’t leave me numb.

Though the We-Connect app is designed for couples to use together, it can also be used alone. It acts as a remote control for the toy, and I like it a lot better than the actual remote the toy comes with. There is something so futuristic and cool about controlling my vibe from my phone. I don’t even have to take my pants down at any point; I can adjust the vibe’s position using my pelvic muscles and its vibrations with the app. Perfect for lazy orgasms at my desk, watching porn, reading erotica, or fantasizing.

Aside from the aforementioned fragile hinges, I only have a few quibbles about the Sync, and they are as follows. First off, the ridgy texture on the vaginal arm makes this toy impossible to clean without a small scrub brush (so, y’know, get a small scrub brush, or an old toothbrush). Secondly, if I’m using the Sync by myself, sometimes I get so wet that it starts to slide out of me and I have to continually readjust it. This isn’t nearly as much of an issue when a partner’s dick is in me, though. And thirdly, the internal arm’s motor is much weaker and buzzier than the one in the external arm. This only bugs me when I’m in the mood for strong G-spot stimulation, which isn’t often, but if you like your internal vibes robust and relentless, you might not be pleased with the Sync.

When I tell sex-nerd friends who haven’t tried the Sync that I’m reviewing it, they’re often disappointed or confused. “Don’t you hate couples’ vibes?” they say, perhaps flashing back to me screeching at the tangled panties of my FixSation, gnashing my teeth while mashing the remote of the We-Vibe 3, or throwing the Lelo Ida on my bedroom floor in an anguished rage.

It’s true that I’ve never loved a vibe of this style before. My former favorite from this category was the Lelo Noa, because it was the only one simultaneously unobtrusive enough not to bother my partner but strong and rumbly enough to get me off. But even that was not love – it was a paltry and resigned “like,” similar to how I’ll begrudgingly pick Wendy’s over McDonalds or Burger King if those are my only choices.

But I actually love the We-Vibe Sync. It does what a couples’ vibe should do: stays in place, doesn’t get in the way or interrupt the proceedings, and gets me off – whether I’m being fucked by a vanilla darling or a darkly dominant beau.

 

The We-Vibe Sync is available at Come As You Are ($237 CAD/about $180 USD), SheVibe ($199 USD), Peepshow ($199 USD), or from We-Vibe direct ($249 CAD).

Come Fly With Me: 5 Travel-Sex Stories

Kate Sloan
A rumpled morning-after bed at the Wythe Hotel in Brooklyn.

I truly felt like a jetsetter the first time I sexted in a TSA line.

Leaving New York felt impossibly sad, in no small part because of the cute boy I’d just met there – but my bleary travel day was brightened by the salacious selfie I suddenly received from him as I traversed that long, slow line.

“HEEELLLPPP,” I replied immediately, my eyes sweeping over his hairy chest, blue eyes, and full pink lips. “911? Yes, sorry, I received a very fire selfie and my heart exploded. What do I do?”

Without missing a beat, he wrote back: “Yes, this is emergency services. Deep breaths, and don’t take your eyes off it. Your heart will repair itself in a few minutes once it adjusts.”

I giggled maniacally at my screen, blushed hard, tried to collect myself. “I’m in a TSA line,” I explained, “and the people around me 100% must think I’m an idiot right now.”

“Welp,” he replied, “sorry if I set off any alarms.”

“Yeah, I’m probably gonna end up on the no-fly list because of all the stars in my eyes,” I mused. “Those seem hazardous.”

I watched the undulating ellipsis as he typed, until his next words appeared: “Guess you’d be stuck in New York then…” Oh, what a tragedy that would be.

After dropping my friend Mia off at her swanky Airbnb post-drankz one night.

The sluttiest night of my life was the time I accidentally booked two sex-dates for one night. It was purely a scheduling error, not intentional at all – but fortunately, both dudes were amenable to the situation.

Dude #1 was my dommy fuckbuddy at the time. I dropped by his place for an early-evening fuck around 6PM. Wanting to try something new, I’d packed some Kegel balls to insert pre-spanking. A far cry away from traditional vibrators, these jiggly little balls vibrate your bits from the inside out every time you get hit, and they don’t even have a motor. It’s a neat trick, and it went over smashingly.

After that date was done, I rushed home and showered for my next one. Dude #2, a Twitter crush visiting from out of town, picked me up and drove us to my favorite pub. Midway through a giggly, tipsy dinner, I texted my dom from earlier, “Should I fuck this guy? I can’t decide.” He weighed the options carefully, taking the decision seriously, and eventually decreed that yes, I should return to this bro’s hotel with him. It turned my dom on, he said, to imagine me fucking someone else just hours after fucking him. (Dude #2, I should say, knew about this whole exchange and was on board.)

Hours upon hours of hotel-sex and fitful sleep later, I got up at 5AM to head out to my 6AM dayjob. As I walked down the creaky old hotel hallway, I heard a creepy clicking sound that seemed to follow me. When I stopped, it stopped; when I continued walking, it started up again. I looked behind me, ahead of me, and around me, but there was no one. My heart froze in my throat.

And then I realized it was the Kegel balls in my coat pocket, clacking together like a taunting soundtrack for my walk of shame. Whoops.

Dressed up at the Holiday Inn Toronto Downtown Centre.

At Woodhull 2016, a fellow blogger held a gathering in her hotel room. She offered up her collection of reject dildos for us to choose from. What an absolute saint.

I knew what I wanted as soon as I saw it. Unlike vibrators that are inspired by nature, this one was inspired by the utterly unsubtle dick of a fantasy creature. It was a behemoth of a dildo, in my blog’s branding colors: pink and blue. I thanked Luna, its original owner, and then cradled it under one arm as I walked down the hall and got on the elevator to take my prize back to my room.

The thing about conferences held at hotels, though, is that there are always guests who aren’t part of the conference, and you have to contend with them. I’d learned this when I took the elevator down in a loud vulva-print dress the day before – and I learned it again, as I endured an uncomfortable elevator ride with two suit-clad blushing businessmen and one giant dildo in plain sight.

I prayed for time to pass more quickly, and wished I’d brought a bigger purse. And as soon as I stepped off the elevator on my floor, I burst into humiliated giggles. What a trip.

At a hotel somewhere in Chicago.

Pros of using Hotwire to find a hotel room: it’s easy, allows for impulsive sex getaways, and is, above all, cheap.

Cons of using Hotwire to find a hotel room: you have no idea, really, what kind of hotel you’ll end up in until it’s already booked. And that’s scary. Sometimes in a sexy way. Sometimes not so much.

My first anal sex experience took place at the Knights Inn, a low-budget hideaway in Toronto’s infamously rough Regent Park neighborhood. The inn itself was sketchy and mildly unsettling, like a scene from The Shining if the film had gone a little tattered and yellow at the edges.

My valiant fuckbuddy knew what a momentous occasion this was, and how much preparation should go into it. He spent long minutes relaxing me, making me giggle, turning me on. And though he is vanilla as fuck, one way he attempted to rev my engine was by spanking me.

The trouble was, the walls were paper-thin. We could hear a cadre of frat boys getting drunk and rowdy in the next room, and though I considered this par for the course, my FWB was spooked. I could feel him backing off the spanking again and again, terrified of making noise, even though the guys on the other side of the wall were being louder than we would be all night.

My handsome friend bunched the thin hotel-bed sheets in his palms and draped them over my upturned ass, as if that would muffle the sound. He experimented with punching instead of slapping. He fretted and overanalyzed and adjusted and readjusted. Finally, enough was enough, and I told him – laughingly, lovingly – to stop.

Hotel sex is supposed to be an escape, but sometimes you still can’t escape your own inhibitions. It’s okay. There are always other things you can do.

Naked and incredulous at the Standard.

The first time I banged my Sir, we were staying at the Standard High Line in New York, one of the most beautiful hotels I’d ever stayed in. I was so nervous I could hardly walk in a straight line.

As we checked in, the clerk asked, “Are you sensitive to noise? This room is right underneath a nightclub, so it can get loud.” It wasn’t an issue. We had no intention of sleeping, and we planned to be pretty loud ourselves. Not that we told the clerk any of that.

My beau pressed the wrong elevator button twice before he got his shit together and hit the right one. He was nervous. It was cute. I was smitten.

I had packed a slew of sex toys, anything and everything I thought we’d need: impact toys, fancy glass dildos, travel-friendly vibrators, cuffs, a blindfold, a book we both loved (which is indeed a sex toy, depending on how you look at it). At his command, I laid it all out for him to look at, arranged it carefully like an Instagram flat-lay, because I wanted him to be impressed.

He must have been impressed, because as soon as I was done, he bolted toward me and pushed me against the floor-to-ceiling plate-glass window looking out on the city. His kisses were fierce and hot and immediate. I knew what was coming and I knew I would be taken care of. I will never forget the way he looked at me, so tenderly and searchingly, as he removed my clothes for the first time – and the way that cold, cold glass felt against my back as my heart pounded in my chest.

Hotel sex can be many things, but it is almost never boring. I can tell you that much.

 

This post was sponsored by THE LILY by Fleurotics. (They’re running a crowdfunding campaign currently that you should get in on!) As always, all writing and opinions are my own.

Story Time: My First Date With My Sir

Kate Sloan

It wasn’t even supposed to happen. My next trip to New York wasn’t booked until February, and that seemed eons away. When the cute nerd from New York slid into my DMs after some back-and-forth flirty tweets and asked if I’d ever want to “meet a Twitter admirer in person over coffee or something,” I thought it’d either happen months from then or not at all. But it was a nice fantasy, for a moment. “Eee, a Twitter dude is flirting with me,” I texted my best friend, and I kind of thought that’d be the end of it.

But then pieces fell into place – it’s a long story involving a sugar daddy, a plane ticket, and an unexpected break-up – and I found myself going to New York in mid-December instead. By that time I had almost forgotten about the cute boy in my DMs, until one night when I pondered the trip ahead and made an impulsive decision. “Hi! I’m gonna be in NY from Tuesday to Friday next week,” I tapped out. “My schedule’s a little packed and it’s kind of a last-minute trip, so I’m not sure if I’ll be able to squeeze in coffee with you, but I’d like to if we can make it work!”

“Hi! I’d like that too,” he wrote back, and we picked a time and place.

The day came. I wasn’t thinking about our date much. I wasn’t even sure it was a date. I had plans for later that day to get on a train to Long Island and go do a pre-negotiated knifeplay scene with a beau, so this coffee with my “Twitter admirer” was just a fun diversion to fill the remaining time until then. My only expectations were good espresso and maybe good conversation. That’s how you should go into every date, really: expecting nothing, so if anything the slightest bit lovely happens, it’ll be an unforeseen treat.

I walked into Culture Espresso on 38th at the appointed time and spotted him immediately: this blue-eyed boy in a blue button-down in front of blue floral wallpaper. He was a vision from the first. I wasn’t expecting that, somehow, even though his big blue eyes in his Twitter avatar were half the reason I’d tweet-flirted with him in the first place. He was cute in the way that usually makes me write someone off, like: There’s no way he’d be interested in me. But he was. He’d asked me out. I didn’t know what to make of that.

“Hi! Can I buy you a coffee?” he asked, bright and extroverted. I declined, wanting to buy my own drink, because paying my own way on a date makes me feel strong and independent and like I don’t owe anyone anything. He told me later this threw him for a loop, made him wonder if I was indeed viewing this as a date – but he recovered well.

I sat down with my latte and we asked each other about our work, our non-monogamy situations, our favorite musicals. (His was Sweeney Todd. I was immediately more interested in him. And I was already pretty interested in him.) I told him about a story I was working on at the time, about unrealistic sexual expectations; when I said “Lots of guys think they can make a woman come from PIV alone,” he rolled his eyes exaggeratedly and that was the first moment I thought, Yeah, I’d like to fuck this person.

“Do people ever make false assumptions about you because you’re poly?” I asked at some point, fascinated. He’d been non-monogamous for years longer than I had, so I went into journalist mode, probing him for wisdom. He pondered that and said, “Totally. People often assume I’m not serious about the people I date. But I’m very serious about the people I date.” A shiver went through me, a quiet premonition that maybe he could be serious like that about me someday. It wasn’t a “chill” thing to say on a first date, but I’m the least chill person I know, so I wasn’t put off – just intrigued.

At one point, he asked me, “Do you think kink is an orientation?” and I brightened even further at the sex-nerdiness of the question. “I think it is for some people. I think it is for me,” I told him. “I’m a submissively oriented person, and I tend to be attracted to dominant, masculine folks, regardless of gender.” His face remained carefully neutral. I wondered if his ears had perked up, somewhere in there, but I wasn’t sure.

We made each other laugh. We shared a chocolate chip cookie. We traded phones to look at each other’s podcasts. He stared into my eyes with such intensity and depth that sometimes I lost my train of thought completely and could only spout excuses: “I’m sorry, you’re just really, really cute.” He smiled opaquely, politely; I couldn’t tell how he was feeling, only knew how I was feeling. I was feeling a lot.

After about an hour, he asked, “Have you eaten? Do you want to go somewhere else?”

I looked out the window at the bitter wintry urban landscape and mused, “If it were summer, I’d say we should go make out in an alley, but it’s pretty cold out there, so.” I have no idea what possessed me to say this. This is the type of line I might bust out if I was 110% certain someone wanted to kiss me, but in this case I wasn’t. I wanted to gauge his interest, and didn’t have much to lose – we didn’t even live in the same city, after all.

This dare of sorts worked as well as I could’ve hoped, however. “That’s a solvable problem,” he said, without missing a beat, and pulled out his phone.

There is an app called Breather, where you can rent nearby office spaces by the hour for meetings, presentations, and work sessions. Not for makeouts, you understand. That is explicitly against the terms of service. But we are rebels.

As he explained his plan to me, he scrolled through the available spaces, picked one, and showed it to me. He titled our reservation “Important Meeting” and leaned across the table and into my personal space to show me the briefcase emoji he had included. I wanted to kiss him right there, but knew it would be better to wait.

We trekked out into the cold and he led me down blustery city streets toward our “meeting” space. “Your shoes are so shiny,” I commented mindlessly, having no idea I was foreshadowing sext-a-thons about shining and licking his boots that would come weeks later. “Thanks,” he replied with a roguish smile. I wanted him to take my hand and lead me where we were going. I was vaguely aware I was following a near-stranger through the streets of a city I barely knew, and that maybe this was ill-advised, but I wanted the warm kisses I was pretty sure awaited me at the end of this chilly journey.

When we got to the building, he greeted the receptionist with more charismatic confidence than I have ever had in my life. As we rode the elevator to the 10th floor, I asked him, “They 100% know what we’re doing here, right?” and he said, “Oh yeah, totally.” I wanted him to push me against the elevator wall and kiss me hard. I wanted some tangible sign he wanted me as much as I wanted him in that moment. I would have to wait.

We were slightly early for our booked timeslot, and someone else was still using the room, so we waited outside. I leaned against the wall and focused on his beautiful face, to the exclusion of all else. “I’m trying to figure out what celebrity you remind me of,” I murmured. He smiled and stared into my soul with those deep blue eyes. Later I would realize it was Cillian Murphy he reminded me of. Um, the boy is very fucking good-looking. Have I mentioned?

When the room freed up, we walked in and took a look around. Ample natural light flowed in the windows. We plugged in our phones. I took some pictures. We busied ourselves with these things for the minute it took us to gather our courage to do what we had come there to do.

I was mid-sentence the first time he kissed me. Neither of us remember what I was saying. He just walked up to me in the middle of that minimalist room, put his hands on my waist, and pulled me toward him. It knocked the words out of me. Our faces were still cold from the winter wind and our noses were running a little and I wanted more of him, more, more, more.

So I told him to sit on the plush grey couch on the far wall, and I straddled him. I like this position for enthusiastic makeouts because, as per Gala Darling, “this way they are [consensually] TRAPPED and can’t escape until my lips are satisfied! I am sneaky like that.”

I leaned into him for long, hot kisses, feeling his body pinned beneath me and his big warm hands traversing my hips and my thighs and my ass. It occurred to me suddenly that I was tugging on his hair without having asked first, and that might be a problem for when he headed back into work after our date; I leaned back and said, “I’m messing up your hair; is that okay?” and he shot back, with a wry smirk, “As long as you put it back after.” We kissed some more and I felt his tongue slide against mine as his stubble scraped my chin.

In a sudden shift of power, he grabbed my wrists and grasped them together behind my back, so I was writhing above him but in a much more submissive manner than I had been a moment before. “Are you a little dommy?” I asked, tentatively, having theretofore assumed he was on the vanilla side of the spectrum. “I’m a switch,” he responded, with the well-worn ease of an actual kinkster, and excitement sparked inside me even further. “I think I want you on top of me,” I breathed.

We shifted; I laid on my back on that beautifully-lit sofa and he climbed on top of me, staking out a spot between my legs with no tact or pretense whatsoever, just pushing my thighs apart with his slim hips. He ground into me through our layers of clothing and kissed me roughly, animalistically, all-consumingly. “You can bite me, if you want,” I offered, shyly, and showed him where. He bit me hard until I moaned, and made me take it. “Good girl,” he purred against my mouth, and I laughed and said, “You’ve done your research!” He flashed me that disarming grin and said, “Maybe,” before giving me his lips again.

Suddenly, we heard what sounded like urgent knocking at the door. He bolted and, in a moment, was sitting on the opposite side of the couch, smoothing his hair and attempting to regulate his breathing, like a dishevelled businessman whose boss just walked in on him with his secretary. After all, making out in a Breather is against the terms of service. A few moments’ hard listening sufficiently convinced us it was just some construction workers hammering across the hall. When he crawled back over to me and took my face in his hands again, I managed to mumble between kisses, “It makes sense, because you make my heart… hammer.” He laughed. I was so, so happy that he laughed.

He wrapped his arms around me and dipped me in a deep kiss, and for a terrifying moment, I thought I was going to fall. “Don’t drop me!” I squeaked, and he held me firmly and said, “I won’t. I promise. I’ve got you.” It felt good to hear that then; it felt even better to hear it weeks later, when, on difficult days, he would text me things like, “Remember our first date when I told you ‘I’ve got you’? I meant it then. I mean it now.”

His hand kept grazing my ass like he wanted to hit me, but he bit his lip and looked past me at the paper-thin walls through which spankings could probably be heard. “I wish we could be louder right now,” he growled ruefully, and I said, “You know what’s quieter than slapping? Punching…” And that is how I ended up stretched over his lap with my ass in the air.

He pounded his fist against my ass, over and over, making me mewl and moan into the arm of the sofa. I writhed against his hard cock, both of us still fully clothed, deliciously so. He volleyed a steady stream of affirming dirty-talk about what a good girl I was, how well I was taking the pain, how much he liked the noises I was making. “You’re so hot like this,” he said, and I still couldn’t believe he really thought so.

“Is this okay?” he asked at some point, and I melted even further and made happy, positive noises. “So then I guess this is probably okay too?” he added, as his fingertips dipped between my thighs and found my clit through my leggings and underwear. As he circled it and made me moan, he commented on how wet and hot I was, and it seemed ridiculous he could feel that through all those layers – and yet I believed it. This boy had rendered me a puddle of arousal and submission, seemingly without even trying.

We didn’t go any further than that. I’d wondered if we might, but somewhere amid all those blurry kisses, he told me he had to get back to work. People would be wondering where he’d gone. It’s not often someone just disappears on their lunch break. And I had to be getting to my train.

We gathered our things, walked down the hall, and got back into the elevator. This time, he did kiss me. He pressed me into the wall and I could feel every contour of that warm, lanky body I longed to see more of. As he snaked a thigh between mine, I worried I’d get his jeans wet. I was that unraveled, that shocked into my body.

The elevator stopped and some strangers got on, some well-to-do businessmen talking about taxes or sports or god knows what, and we jumped apart and stood silently side-by-side, our hearts thumping, our molecules mingling. We reached the ground floor and stumbled out into the harsh winter sunshine together, dazzled, disoriented. “Will you walk me to where I’m going?” I asked. Google Maps could’ve helped me, but I wanted more of this boy. Just a few minutes more. Or whatever I could get.

He said yes. We weaved through city streets together looking for the store where my best friend Bex works; he was going to drop me off there so Bex could walk me to my train. “I feel weird,” I commented, all light-headed and foggy, and I realized as we talked that I was in subspace. It’s unusual for me to lapse into that space from such a short and, frankly, non-naked interaction – but he had made me so submissive and turned on that it made sense. He didn’t hold my hand as we walked, but he told me later that he wished he had; he was just shaken up and worried about me and worried about how long he’d been gone from work.

We got to the store and paused outside. “I’ll let you know when I’m coming back in February and maybe we can hang out,” I said, trying too hard to seem chill and unaffected.

“Yeah! Totally,” he replied, internally breathless but externally calm. We kissed goodbye, smiled at each other, and I went into the store, wanting to watch him stride off into his city but worried that’d seem uncool of me.

I didn’t think I’d see him again, honestly. I didn’t think he liked me enough to stay in touch. I didn’t think he wanted more from me than just that one weird almost-hookup in a Breather. But I’m chronically insecure about such things; he was showing interest, I just didn’t see it, didn’t believe it.

That afternoon he texted me a screenshot of the Breather receipt, captioned “for your records.” The following morning, I texted him, “Still thinking about those extremely good kisses,” and he replied, a mere eleven seconds later, “I was literally just thinking the same thing.” The next night, we sexted for the first time, while I was curled up on Bex’s living room sofa. The morning after that, he sent me a blisteringly hot selfie while I was waiting in a TSA line at the airport. The next day, when I was back in Toronto, he told me, “I’m really enjoying playing with you and getting to know you. I hope you know that.” I still didn’t quite believe he wanted me.

We’ve been dating for three months now and I still don’t quite believe it. But I’m happy about it nonetheless. I’m happy I answered that DM, happy I went on that coffee date, happy I kissed that boy in that Breather. I’m happy about it every day.