blowjob

It’s Different With You

Kate Sloan

The first time anyone slapped my face, it was because I asked for it, and it was an experiment.

He was an ostensibly vanilla man I’d met an hour earlier, at a sex club. His posh British accent and shy befuddlement set me immediately at ease: this man was no threat to me. He could fuck me, maybe, but he could not fuck me up.

Face-slapping had been on my mind lately. I had no idea if I’d like it. I liked certain types of pain, but getting hit across the face seemed like it’d be uniquely disorienting and extra risky, physically and emotionally.

Normally I like to try new kink things with a safe, trusted, established partner. But I had no such partners available to me. It had been a while since I had. That was starting to feel disheartening. I tried not to think about it too much.

So when this nice English boy had his fingers deep inside me and his lips on my lips, I leaned back and said, “Can you do me a favor? Can you slap me across the face?” His expression, then, was shock muffled by politeness. “Not too hard,” I clarified. “Like, a 4 out of 10.”

To his immense credit, he did not balk. He was vanilla as fuck (or so I assumed from how he later repeated the phrase “good girl” at me like it was a magic arousal spell in and of itself), but he was nonetheless willing to do this for me. Good boy, I thought, as he wound up his batting arm.

The slap landed. It hurt. It shook me. But it did not turn me on.

Huh, I thought. Guess I’m not into that. We did not speak of it again, he did not attempt it again, and the evening progressed in an otherwise vanilla but quite enjoyable way. And that was that. Or so I thought.

The first time you slapped my face, I had also asked for it. But it felt entirely different.

We’d been dating for a few weeks, and having kinky sex in massive quantities. All traces of vanilla had been flushed from my system, it seemed. I thought about going on Tinder dates with other boys, letting them put their hands on me gently and fuck me in entirely standard ways, and the whole idea just bored me to death. Sex with you felt exciting not only because you were rough with me, but also because I trusted you to be rough with me. I wanted to show you how much I could take. I wanted to be good for you. I cared.

We hadn’t talked about it yet, but I felt strongly enough to bring it up nonetheless: “I think I’d like you to slap my face.” You got that devious domly smile on your face I like so much, the one that means you’ve got some mean tricks up your sleeve and I’m gonna like ’em. “I don’t know if I’ll enjoy it, but I want to try,” I added. You nodded and I saw you file this info away for later.

Later came. Long minutes into hard makeouts, you climbed on top of me, straddling my thighs in bed, and grabbed my hair by the root in one hand. “I’m gonna slap you across the face now,” you muttered against my mouth, and I nodded.

My eyes are normally closed during sex; it’s how I process sensations best, and one way I manage my sexual anxiety. But the moment stretched out and I wanted to see. I opened my eyes just in time to see your hand cocked back, ready to strike. A split-second elapsed and you hit me, hard but not so hard it scared me. I felt jolted. Grounded.

My eyes had fallen closed, and after a moment, I opened them again. I did a thing I almost never do during sex: I looked up at you – coyly, through my lashes – and smiled.

You smiled back, and then you hit me again.

Some vanilla people can talk all day long about how romantic their sex can be, how intimate, connective, sweet and life-affirming. That’s fine. I’m glad they experience it that way. But kink can be those things, too. That moment where I’m smiling up at you, knowing you’re about to hurt me, and then you go ahead and do it? That’s the safest and the sweetest. I feel romantic toward you when we’re cuddling or kissing or holding hands in public; I feel it even moreso when you’ve got me pinned and you’re about to leave a handprint on my cheek.

The first time anyone fucked my mouth, it was an accident and I hated it.

He was a submissive boy – which, fine, whatever. Banging other subs isn’t my favorite, but I can deal with it, if it’s only an occasional thing. Submissive guys can still enjoy receiving BJs, after all, so at least there’s some overlap between our tastes.

Reclined on a soft hotel bed, he moaned and mewled as I bobbed up and down on him. I was doing a great job and I knew it. If this was the only fun thing we could do together, I’d be okay with that. It was pretty stellar, as far as BJs go.

But then he started thrusting into my mouth, and I froze.

My gag reflex is off the charts. I have, more than once, accidentally thrown up from scrubbing a toothbrush too far back on my tongue. I like BJs where the recipient is lying on their back, in part because it gives me optimum control over the depth of the dick. When I lose that sense of control, sometimes I gag. Sometimes I panic.

I tried to be chill about it. But after a few minutes, I could not. “Hey, can you stop that?” I mumbled during a pause, pressing my hand against his hipbone to still him. “You’re gagging me.”

“Oh. Sorry,” he said. “I’ll try to stop.” He tried. He didn’t really succeed. I get it; sometimes thrusting isn’t entirely voluntary. But I spent the rest of that BJ trying to get it done, instead of enjoying it for what it was. My throat didn’t trust him anymore.

The first time you fucked my mouth, it was highly negotiated, and I was ready.

A few days previous, I’d mentioned – in one of our many chats about desires and boundaries – that my skittish throat was a frequent buzzkill for me. “It’s why I don’t really like choking or face-fucking,” I said, “even though I’m totally obsessed with deepthroat porn and find it so hot.”

The conversation meandered in a different direction, but a few minutes later, there was a lull, and you mused, with a soft smile: “So no face-fucking, hey?”

The way you say “hey” instead of the more familiar-to-me Canadian “eh” is somehow so endearing to me; it sneaks into your dirty-talk when I fantasize about you, a signature feature of your vernacular that puts an instant smile on my face. With anyone else, I probably would’ve just said, “Yep, no face-fucking,” and moved on. But you – your pressureless demeanor, your easy handsomeness, and that gentle little prod of a “hey” – gave me pause.

“I meeeeean,” I began, in that way I begin sentences when I know I can be swayed. “I haven’t liked it with previous partners. Maybe I’d like it with you.” You grinned. I grinned back.

Later, after embroiling me in subspace in all the pervy ways I like best, you arranged me on the bed so my head hung off the edge. You placed my hand on your warm upper arm and said, “I want you to tap my arm if you want me to stop, okay?” And then you slowly slid your cock into my throat.

There was an ease to it I had never experienced with this act before, an instant and eager facility. I could feel myself getting wet as I thought about you using my mouth, fucking all my holes like I was your personal sex toy.

At some point, I started to gag, and tapped your arm. You stopped immediately, made sure I was okay. But I wasn’t scared or shaken. I was smiling. I wanted more.

The first time anyone choked me, I was fucking furious.

“I told you I don’t want to be choked,” I practically shouted. His hand had snuck onto my neck too many times. He knew what was up. This was the last straw.

“I’m sorry, I’m sorry,” he babbled. “My other partners all like being choked. I keep forgetting that you don’t.”

I rolled my eyes. He had used this excuse more than once before. I had no idea whether to believe it. It did seem that his memory was genuinely bad – he’d often tell me a story he’d already told me, or stare at me blankly when I referenced an anecdote I’d relayed the week previous – but it also seemed like a half-assed attempt to eschew my boundaries.

He was the first polyamorous person I’d been involved with, and the whole situation made me doubt that poly was right for me. If mixing up your partners’ sexual preferences was an occupational hazard of poly, could I ever really trust a partner? Could I ever truly enjoy myself, knowing someone could badly fuck up at any moment?

Months after I stopped seeing him, I talked to another former partner of his. She told me he was always “forgetting” her boundaries, too. Maybe that’s not a thing poly people do, I thought; maybe it’s just a thing abusive shitheads do.

The first time you choked me, we had – again – talked about how I’d never liked it before, but thought I might like it with you. You tend to have that effect on me.

“I’m going to put my hand on your throat,” you told me, your face so so close to mine, “but I’m not going to choke you.” You were true to your word. It didn’t scare me. Instead, weirdly, I felt safe.

“When you go home tonight,” you continued, “I want you to masturbate thinking about my hand on your throat. I want you to think about how small and defenseless it makes you feel – and how happy it makes me.” When I relayed this episode to my journal later, I wrote, Damn, he’s good. And indeed, I jerked off thinking about what you’d told me to think about. And it made me really fucking wet.

The first time you actually put pressure on my throat, I squeezed my eyelids shut from the intensity of the sensation. It didn’t feel bad, it was just… a lot. “Open your eyes. Look at me,” you commanded sternly, calling me back to earth. I did as you’d asked. “Hey. It’s okay. You’re okay.” And I knew you were right, and I was safe.

You released the pressure slowly, and I wanted to cry. Never knew I could feel like this, I thought, a love song from Moulin Rouge echoing in my brain. It was a strange thought to have immediately after being choked, maybe, but it was what came to mind.

See? Kink can totally be romantic.

Kiss and Make Up: High School, BJs, and the Disappearing Act

Kate Sloan

Kiss and Make Up is my new series wherein I review makeup according to how it held up in a sexual scenario. I hope you dig it!

making kissy faces with my friend Cadence in 2010I sprung for Duwop’s Lip Venom in the winter of 2010, when I had a new boy to kiss and it seemed desperately important that my lips look good. I’d wear the cinnamon-y gloss layered over MAC Russian Red (as pictured) or just on its own, and it would do its signature magic of irritating my lips into a plumper appearance. I loved it: the sharp spicy taste of it, the telltale tingle, and most of all, those plush pillowy lips it gave me. What an amazing invention.

My boyfriend, however, was less enthused. “What is on your lips?” he whined one day, mid-makeouts. The Lip Venom, he said, was stinging his lips. I apologized and wiped it off, as if this pretty pink gloss was the only obstacle between us and high-quality kisses. Truth be told, he was a distressingly bad kisser (by my tastes, anyway), and I wished he could’ve upped his game as easily and quickly as I upped mine by taking off that painful gloss.

I wore NARS Schiap lipstick the last day of Playground Conference in 2015. It paired well with my blue dress, pink handbag, and pigtails. In fact, my outfit was apparently so good that when I walked into a panel session late, I immediately got a text from my dom fuckbuddy, sitting across the room: “Oh god, you’re wearing thigh-high socks and a short skirt. I’m going to be thinking about eating you out all day.” This is a very good text to get at 11 in the morning.

NARS semi-matte lipsticks smell like clean laundry (so sayeth Sofie, who is correct). They go on satiny-smooth, and usually look good for several hours, even if you’re quaffing coffee like I was that day at Playground. However, put to the makeout test, they cannot hold their own. I discovered this when, later that day, I gave a hotel-room blowjob which morphed into an impromptu threesome – by the end of which, there was absolutely no lipstick left on my face. I smoothed on some peppermint lip balm to soothe the irritation I’d accrued from kissing a scruffy boy all afternoon, and that helped.

In my post-sex debrief with Bex over mac and cheese that night, we talked about how kissing someone who’s wearing lipstick is a lot like going down on someone who’s on their period. It’s messy, and maybe embarrassing, and I can completely understand why you wouldn’t want to do it. But I’ll like you so much better if you do.

me in pigtails and Pink Pong lipstickI fell in love with Bourjois liquid lipstick in Pink Pong at a drugstore and bought it on the spot. It was everything I most want in a lipstick: an eye-gougingly bright cool-toned pink, an opaque formula, a pleasant scent (pink grapefruit?), even a punny shade name.

Unlike many liquid lipsticks, Pink Pong felt comfortable once dry, and didn’t render my lips dry or cracked, even after many hours of wear. However, that dry texture is what allows truly long-haul lipsticks to stay put (and why Make Up For Ever Aqua Rouge comes with a clear gloss you’re supposed to wear on top of it). My new Bourjois treasure passed neither the makeout test nor the blowjob test.

That was the month when I was seeing both a boyfriend and a beloved fuckbuddy, alternating between them like my life was a buffet of good dicks (which, let’s be real, it often is). I wore Pink Pong to boyfriend’s house one afternoon and blew him while he sat on his couch like a king, arms spread wide, head dropping back in quiet pleasure. When we were done, I ducked into the bathroom and saw that there was no lipstick left on my mouth. None whatsoever. There sure was a lot on my hands, though. (Uhh, my BJs are pretty handsy.)

Later that week, I wore Pink Pong to my fuckpal’s place and we made out like teenagers in his cheap, squeaky bed. When he served us a post-canoodlin’ snack of spicy salmon sushi and Magnum ice cream bars (quelle gentleman!), he wiped his mouth on a napkin and the white scrap came away pink. “Aww, Kate, look, your lipstick’s all over my mouth,” he said, with an affection I had never known any boy to feel about my lipstick before. It made me want to kiss him a whole bunch more.

me in Maybelline Rich Ruby lipstickIn the late summer I briefly had a “spanking buddy.” It was a sweet deal. I’d go over to his place, we’d talk about the Adventure Zone and MBMBaM and other fine McElroy products, we’d vape some weed, and then he would spank me. The spankings were excellent: rhythmic, firm, and merciless. He always left both my sets of cheeks blushing.

One such night, I showed up with a full face of makeup, and by the time we said goodnight, there was none left at all. My lipstick of choice for the evening was Maybelline’s Rich Ruby, a creamy, matte, cool-toned red that normally holds up pretty well through food and drink. But it did not hold up through a spanking. Granted, when I get spanked, I typically bury my face in pillows/blankets/couch cushions, and sometimes I cry, and that combination of friction and fluid is not kind to makeup.

“How’s my lipstick looking?” I asked my spanking buddy when I raised my head off his bed, post-beating. He peered at me curiously and said, at last, “It’s not bad… it’s just… not there.” Indeed, it was not. My lipstick was gone.

After I left his place and went home, I got a text from him. “I found your lipstick,” he said. “It’s all over my blanket.” I laughed and apologized, and we said goodnight.

When my FWB came over to our sunny Airbnb in July to shoot BJ porn, I was nervous to the point of pacing and raving. “Hey, shh, it’s gonna be okay,” he told me. “You’re gonna be great.”

He had brought some underwear options, and asked for my help deciding which ones to wear – possibly as a tactic to distract me from my own jangling nerves. We eventually settled on some turquoisey boxer-briefs. “They’re moisture-wicking,” he commented, for no apparent reason, because he is a weirdo.

Just before filming was to begin, I knelt in front of him, my face all done up. On my lips was a combo of ColourPop’s lip pencil in Heart On and Bite’s fruity lipgloss in Bellini. I wasn’t at all confident it would stay on my face, but then, smeary lipstick is a selling point of BJ porn for some people. “I’m gonna kiss your dick through your underwear a bit before I start,” I jabbered nervously at my FWB. “Sorry in advance if I get lipstick all over these beautiful boxer-briefs.”

“It’s okay, they’re moisture-wicking,” he replied, and so there is a moment in the final porn scene where I giggle like a dork, and that is what I am giggling at.

By the time we finished, my face featured almost no lipstick but a euphoric, nervous-no-more kind of smile.

Links & Hijinks: Blowjobs, Dopamine, & Carmen Miranda

Kate Sloan

• Girl on the Net wrote about rediscovering the real joy of sex after stressing yourself out thinking that sex “should” be joyful. I love pieces like this which acknowledge the sometimes unglamorous realities of sex, which many people feel broken for experiencing.

• Here’s some men talking about their sex toys. There’s lots to like about this article, but I particularly lost my shit over this line: “Men can orgasm at the drop of a hat, generally speaking (at least if it’s a particularly sexy hat — I’m thinking a Carmen Miranda fruit hat, that big wide-brimmed one Beyonce wears in the Formation video, one of those ones that has a beer can on either side).”

• Is mocking a man’s small dick on par with the body-shaming experienced by women? To me, the answer is “obviously yes,” but this article is still worth a read, if just for the absurd story therein about two Instagram models whose post-breakup drama played out online in the form of passive-aggressive dick snipes.

• “I can’t stop thinking about penetration” is one of the best opening sentences I’ve read in a while. Here, the Establishment’s Katie Tandy writes beautifully about penis envy and power dynamics.

• The great Alana Hope Levinson’s thoughts on “the cuckboi” made me shriek with laughter. “The cuckboi understands that there’s no ethical consumption under capitalism, unless you’re eating pussy.” TOO GOOD.

• On the loquacious raving and “intrusive thinking” that happens when you have a new crush: “When the object of your desire isn’t around, and therefore you lack that dopamine rush in your brain, you might feel like you’re in withdrawal. So, you may try to achieve small dopamine rushes from talking about your crush to your friends.” Gawd, I am so guilty of this. Sorry, friends.

• My bestie wrote about why they love blowjobs. *sigh* Why am I not blowing anyone right now?! (Well… this post was prewritten and queued up in advance, so I guess it’s possible I am blowing someone right now, as you read this. Who can say?)

• Bex also wrote about sex ed, sex-positivity, and meeting people where they’re at. I love this. I’ve only been working in sex toy retail for two months but I already feel like I’ve learned so much about these concepts from working on the “front lines.”

• This piece on anxiety and productivity is haunting and important. Read this if the current state of the world makes you anxious and so do thoughts of resisting, standing up for what matters, making change.

• Trans kink porn is important! God, this article reeeeeally made me want to watch The Training of Poe…

• Depression may actually have a positive evolutionary purpose. Certainly puts things in perspective! “This framing of depression as a space for reflection is empowering, and lends a degree of agency to the person being pressed down,” Drake Baer writes. “Like anxiety, depression might be trying to tell you something.”

• A “boyfriend dick” is the kind of dick you could see yourself settling down with. I must say, though, I prefer the more gender-inclusive phrase “good dick,” which really says it all! (Incase it wasn’t obvious: the concept of a “good dick” is very subjective. Please don’t worry about whether your dick is good or not. If you keep it clean and use it respectfully, there are lots of people who would consider it a “good dick,” I promise.)

• What happens when best friends control each other’s vibrators?! (I think me and Bex should try this sometime.)

• Maybe we need to reject body-positivity and embrace body-neutrality. I love this idea! “Neutrality is the freedom to go about your day without such a strong focus on your body,” says one of the people quoted in this article.

• JoEllen wrote some spot-on guidelines for having good, ethical casual sex.

• This piece about Trump and BDSM argues that consent education, and the communication skills one can learn through practicing kink, are more critical than ever in our current political climate. Interesting stuff.

• I loved this short piece about pain, mindfulness, and transcendence. It spins a whole world out of a few moments of intense (consensual) pain, which is indeed what those experiences feel like to me sometimes.

Links & Hijinks: Sex Robots, Moneyshots, & Bart Simpson

Kate Sloan

a chair, a table, and a latte

Me: “Why did I start doing link round-up posts again?! I don’t even read that much!”

Also me: *reads a ZILLION articles, wants to share and talk about ALL OF THEM*

• The Establishment posts so much good stuff – although I will say, I am extremely biased, because they’ve published my writing on multiple occasions! I just discovered this old piece on there called Online Dating in 7 Vignettes which gave me so much poignant food for thought. It’s one of the more thoroughly philosophical pieces I’ve ever read about dating.

• Soon, sex robots will have personalities. Hilariously, one of the 12 personality traits you can choose from is “sexual,” which makes me wonder about the kind of person who would buy a sex robot and not want her to be sexual. The always-whipsmart Tracy Moore writes: “I’ll be honest, I wasn’t sure ‘sexual’ counted as a personality type in a woman, so I asked the man standing nearest to me in the MEL offices if men think it is, and he said ‘Sexual?’ and thought about it for a second. ‘Yeah,’ he said. ‘Horny.'”

• Social psychology is fascinating. Here are some science-tested tips on making friends faster. The “misattribution of arousal” is one of my favorite social-psych phenomena; one day I’ll write a post about it…

• Don’t say “but” when you apologize to someone. It undermines the sincerity of what you’re trying to say. Cari Romm reports, “According to one 2014 study on the subject, a well-executed apology requires the offender to make it clear that they understand what they did wrong, take full responsibility, offer a plan to fix things, and promise to improve in the future.” So simple and yet sometimes so difficult!

• Some sex-magic practitioners weighed in on how to cast spells with your orgasms. (Years ago, I wrote a piece about this for the Numinous, if you’re interested. It is some truly crunchy/hippie/witchy stuff; you have been warned!)

• An old friend of mine started a sex blog recently and she’s been writing some fabulous, smart pieces. Her and her boyfriend tried a bunch of wacky sex positions; the ensuing post makes me want to work on my sexual acrobatics!

• The evolution of porn tropes is so interesting to me. Here’s an oral history of the moneyshot. Personally, I’m not really a fan; it turns me on most in porn when a dude’s orgasm happens inside his partner’s mouth or other various orifices, not on their face. The palette of human sexual desire is so wide and diverse!

• Ever wondered why “shrinkage” happens?

• Here’s a piece on people whose kink is giving and/or getting tattoos. I thought about this a lot while getting my kinky thigh tattoos last year. I don’t think I could ever get a tattoo that was mentally tied to a specific partner; I’ve never liked anyone enough to want to be with them for-literally-ever! But maybe someday I will…

• S. Bear Bergman has been one of my favorite writers for many years, and after the 2016 U.S. election, he wrote an advice column answering the question, “What do we do now?” He touches on political action, self-care, and countering social isolation in tough times, and he calls Trump “Pumpkin Spice Mussolini.” It’s a much-needed half-laughing pep talk for this weird and worrisome era we’re in.

• The ever-articulate Andrew Gurza wrote about his recent experiences with disability and masturbation. I admire Drew’s candidness and thoughtfulness so much!

• This article is old but I only just discovered it: a Playboy reporter interviewed the founder of the Orgasmic Meditation movement about how she gives blowjobs for her own pleasure. I am always wary of narratives which frame blowjobs as an endeavor of empowered women (including when I myself write that kind of narrative!) because they feel dangerously close to patriarchal tropes repackaged as female empowerment. But if Joanna Van Vleck genuinely gets direct pleasure from giving head (a feeling I know well), I say, more power to her.

• Here’s two of my favorite women writers in conversation: Tina Horn interviewed Alana Massey about the latter’s new book, as well as sex work, internalized misogyny, and gold glitter.

• C. Brian Smith – one of my fave writers over at MEL – hired a masturbation coach for an afternoon and wrote about his experience.

• More excellent pieces from MEL this month: why “performing partnership” on social media complicates relationships, the potential queerness of Bart Simpson, how men feel about hookup culture, saving exes’ nudes after a break-up, and saving exes’ Clone-a-Willy dicks after a break-up.

• Queer tarot wiz Carly wrote a column about how to date/flirt/socialize if you’re shy. So much useful and affirming stuff in here!

What did you love reading on the internet this month?

12 Days of Girly Juice 2016: 3 Fave Encounters

Kate Sloan

Today’s “12 Days of Girly Juice” instalment sums up my three favorite bang sessions of the year, and I have an embarrassing secret to confess: unlike last year’s diverse trio of fucktimes, all three of these encounters were with the same person.

It’s embarrassing because it implies that he’s the only good partner I’ve had all year, out of the 12 partners I had in 2016, and that none of the others were worth remembering or writing about. That’s not true at all; I had so much good sex this year and all of it was worthy of celebration!

But there are emotional factors at play which affect how I think about all those encounters. Many of those people have peaced out of my life, after messy break-ups, painful rejections, and/or shocking betrayals – and that drama retroactively mars the memory of the sex I had with those folks. What was amazing sex at the time just feels sad in retrospect.

The following three stories are about a fuckbuddy I’m still friendly with, one who doesn’t make me feel sad, resentful, angry, or betrayed. As such, my memories of sex with him have been left untouched by chaotic emotions, so I’m free to recall these memories in their full splendor. They seem every bit as hot, fun, exciting and transformative now as they did then.

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I snapped this selfie for Bex before embarking on my BJ date. “Do I look pretty?!”

Impromptu blowjob date

On the evening of February 11th, I sat in a lukewarm bath, realizing my sex life was about to change.

A few days earlier, I’d blown a fuckpal whose dick just jived with my mouth. Craving blowjobs was a completely new thing to me, so it’d taken a few days to sink in: not only did I enjoy blowing him, not only did I want to do it again, but I couldn’t stop thinking about doing it again. This was, for me, unprecedented.

In a sudden fit of impulsive bravery, I leapt out of the bath, grabbed my phone, and tapped out this DM to the aforementioned good-dick’ed dude:

Apologies if this comes across as crass or un-“chill,” but I have been thinking a lot about going down on you and would 100% be down to do that again sometime soon. Just lemme know. Sincerely, girl who is totally not this much of a BJ perv with most people but just had to speak what’s on her mind(/vag).

His reply was, shall we say, enthusiastic. We hammered out details, I threw on some clothes, and then I ventured out into the icy Toronto evening, en route to dat dick.

I gave him two blowjobs that night: one when I arrived, amid giggles, blushing, and R&B slowjams – and one later, after we’d gone out for drinks and dinner, when he muttered darkly into a kiss, “I’m thinking about your mouth…”

Sexual tastes take time to shift; it’s rare for a kink to spring up, fully formed, overnight. So maybe my descent into the Blowjob Fandom was more gradual than I realized. But for me, this is the night I’ll always remember as The Beginning of My Blowjob Obsession. Some dicks are so good, they make history in your life. Some dicks are so good, they rewire your brain. Some dicks are so good, they conjure desire where before there was only distaste.

Some of the toys I brought with me to our hotel-buttsex date (and a bottle of gin).
Some of the toys I brought with me to our hotel-buttsex date (and a bottle of gin).

Anal sex in a sketchy hotel

When we went out for dinner and drinks between Blowjob One and Blowjob Two (which sounds like a duo of Dr. Seuss characters I’d dearly love to meet), we discussed the possibility of him being the first person to fuck me in the ass.

It hadn’t occurred to me before that night in that Distillery District pub, but this particular fuckbuddy was really the perfect person to usher me into the world of anal sex. I liked and trusted him, we had good sexual rapport, and he had experience with butt stuff from both sides of the dick. He outranked me in the realm of Butt Wisdom, and I trusted him to guide me through the experience.

We booked a cheap hotel for the following Monday night and met up there, both nervous as hell and self-medicating with weed (him) and gin (me). We set the scene by cuddling, talking, and joking around. And when we were ready, we started into a sex sesh that lasted about four hours in total. Four languid hours of messing around, laughing, and trying things out. My butt got fucked at some point during the proceedings, but it didn’t feel like the Main Event; everything else was so much fun that the actual butt stuff felt very low-pressure and almost like an afterthought.

This night confirmed what I already knew: that goofy, relaxed sex is my favorite kind, that a shared sense of humor and rapport is vitally important to my sexual enjoyment with a partner, and that – yes! – I like getting fucked in the ass.

I don’t know that it’s always useful to agonize over who should be “your first” when it comes to a particular sexual act. I’m endlessly picky about who I want to fist me first, for example, whereas the first person I ever had sex with was just a friend, for whom I didn’t have sexual feelings. I think the importance of the person really depends on the specific act – and because anal sex is highly intimate, emotionally risky, and physically tricky, I’m super glad I held out for someone I deeply trusted and adored. The experience could not have been any better, truly. I think back on it with immense fondness and gratitude, and I hope my butt gets fucked more in 2017!

28042689031_dbf0210c7d_oBAMF threesome

One night in April, my then-boyfriend was over an hour late to meet me. I complained to Bex, who said, “You know who’d never be late to meet you?” and then they said the name of my fuckbuddy, who, at that time, I hadn’t seen in quite a while and missed a lot.

Bex was joking about my FWB being better for me and nicer to me than my boyfriend, but they were also right. That boyf was disrespectful, unfeminist, and made me feel terrible about being a sexual person. He always wanted me to “warn him” in advance if I wanted sex, acted like it was a favor he’d begrudgingly do for me, and talked about my body less like a hot piece of ass and more like a mildly distasteful science experiment. Though I didn’t want to admit it, I missed having sex with people whose approach to sex was spontaneous, enthusiastic, and joyful. Like that far-away fuckbuddy.

After tweeting about Bex’s remarks, I went to bed, because I had work early the next morning. By the time I woke up, Bex had a) had a conversation with said fuckbuddy about my tweet, b) explained that my boyfriend was basically the worst, and c) established that me, Bex, and the FWB should totally have a threesome. Bex makes dreams come true. They hadn’t gotten the go-ahead from me to set this up, but they didn’t need to: months earlier, on a streetcar, I’d randomly turned to them and said, “Hey, hypothetically, would you ever want to have a threesome with [my FWB]?” to which Bex immediately said, “Yeah!” So there was a precedent. And now that plan had been set in motion.

Over the next six weeks, we planned, brainstormed, sexted, and negotiated. I booked a bus ticket to New York and wrote a decidedly sex-centric packing list. We titled this landmark event “the BAMF threesome” – “Bean (Agender)/Male/Female threesome” – or, alternatively, “The Great Threesome of 2016.” I broke up with my boyfriend, in part because I realized I’d never been half as excited about him as I was about this threesome.

We wore matching rainbow socks, 'cause we knew the dude liked 'em.
We wore matching rainbow socks, ’cause we knew the dude liked ’em.

I took a 10-hour overnight bus from Toronto to New York, and then trekked from the bus station to Bex’s Queens apartment with my little suitcase and backpack full of sex toys. When I arrived, I found that we were wearing the same shirt, which just reiterated the whole “we are gonna sexually team up on a dude tonight” vibe.

The threesome itself was fucking adorable. Dude came over, showered, and the three of us nervously cuddled on a couch for an hour or two, talking and catching up. Then we semi-awkwardly transitioned to kissing, moved to the bed, and took some clothes off. What followed was a blurry mess of blowjobs, fingerbanging, spanking, fucking, biting, dirty-talking, and laughing. It was a magnificent synthesis of two people I love very much and all my favorite aspects of sex. So, basically: the best.

Despite all the threesomes I’ve been involved in, they’re not really my jam – I prefer the unbroken focus and intensity of one-on-one encounters. But sometimes the stars just align, and a magic threesome materializes from the ether like a stroke of genius. This was one of those. More than a sexual encounter, it was a bonding experience, a true test of friendship, some serendipitous playtime. I felt so lucky to know both of those people.

When we were done fucking, we ordered Mexican food, ate it while sitting unselfconsciously naked on Bex’s bedroom floor, and then climbed into bed for a cuddly three-way snooze. I’ve rarely gone to bed so happy, comfortable, and satisfied in my life.

 

What were your favorite sexual encounters of 2016?