How to Flirt With Your Conference Crush

I just got back from the Woodhull Sexual Freedom Summit, and… wowza, y’all. There were a lot of cute people at that event.

While some of the cuties were folks I’d never heard of before I arrived, many of them were people I’ve low-key known on social media for a while. It’s maddeningly exhilarating to meet someone IRL and find that they’re even more adorable and charming than they were on the interwebz. That pleasant surprise can throw you off your game and make you nervous – maybe even so nervous that you can barely talk to your crush, let alone flirt with them!

I definitely fell into that trap with a few people this year. So I’ve put together this little guide to flirting with your conference crush. Hopefully it helps you – and maybe it’ll even help me at the next conference that rolls around!

Pre-game. If you start flirting with someone out of nowhere at an event, they might be confused or even put off – so it’s good to get a feel for their interest level and flirting style before the event itself. Build rapport over a period of weeks or months with jokes/jibes/compliments on social media. Find excuses to slide into their DMs, if they seem down to talk to you (our social media flirting episode of The Dildorks has some great tips on this).

Use this time to gauge how receptive they might be to your flirtations. If you’re particularly crafty, you might even be able to establish what types of activities you’d be up for at the con (“I have this new paddle I haven’t gotten a chance to use yet…” “It’s been so long since I’ve been properly fingerbanged!” “I’m looking forward to some possible makeouts at the event…”). Maybe you’ll plant a seed that’ll turn into a fun hookup later on!

Check in. Boundaries and consent are vital! Conferences are professional environments for many people, so your crush might not feel entirely able to say no if they’re not into you. This makes it super-extra important that you establish clear consent for any flirting-and-more that takes place.

Meta-communication is great for this, particularly if the crowd at your con is nerdy about sex and relationships. Flirting expert Reid Mihalko often recommends asking some version of “Is this a good time to flirt with you?” or “Are you open to being flirted with right now?” and I think that’s a good approach, so long as you’re attuned to hesitant yeses that are actually no’s.

If you’re not sure how you’re being received, you can also pay attention to the length and tone of your crush’s responses: are they engaging with your flirtation and coming back with their own, or are they simply acknowledging your comments with short responses every time? When you enter a room they’re in, do they look at you, smile, walk up to you, or do they avoid you? Pay attention to cues and do your best to be respectful. All the other tips in this post will only go well for you if your crush is receptive to being flirted with; if they’re not, doing this stuff will just be creepy or even harassment.

Use social media to your advantage. Many conferences have heavy social media engagement, so it won’t look too out-of-place to throw a few swoony tweets into your con coverage (provided, of course, that you’ve been getting good signals from them, as per my previous point). Some examples of things you could tweet: “OMG, @YourCrush’s outfit today is AMAZING 😍” “I keep hearing @YourCrush’s adorable laugh during panels and it makes me so happy!” “Thrilled I got to meet @YourCrush after loving their blog for months!”

You could also try tweeting general callouts like, “I’m going to the pool/business centre/balcony; y’all are welcome to join!” or “I’ll be at [x panel] next; come sit with me!” If your crush is creepin’ you like you’re creepin’ them, they’ll probably show up to some events you’re attending – at which point you can get yo’ flirt on.

More social media tricks for con flirting: send an “It was nice to finally meet you tonight; hope I get to see more of you!” DM a little while after saying goodnight. Ask them if you can get a selfie with them at some point (provided you’re also getting selfies with other people; don’t be a creep!). If they tweet about being at a panel they’re not enjoying, or not knowing what to do next, send a reply along the lines of “We’re at [x place/event]; you’re welcome to come join!”

Sync your schedules. Don’t follow them everywhere, obviously. That’s gross; don’t do it. But if you’re getting good vibes from them, you could try inviting them to lunch, telling them about a cool panel you’re planning on attending later, or letting them know about an after-hours get-together you’ll be at.

If you’re really getting good vibes, you could try straight-up saying something like, “Hey, I feel like I haven’t gotten enough time with you at this con! Wanna [sit together at this next panel/grab coffee and chat/come look at my dildo collection in my hotel room]?” Cons are busy enough that they’ll have an easy “out” if they want to say no but don’t feel comfortable being upfront (“Ahh, sorry, I can’t, I have to [go to a different panel/go talk to my friend/take a nap]!”).

Say yes to adventure. It’s easy to get tired, overwhelmed, or nervous at cons, which might lead to you declining invitations you otherwise might like to accept. While self-care is hugely important, you should also cultivate the ability to tell when you’re so tired that more socializing would actually burn you out, versus when you’re tired but still capable of going on adventures if you push yourself a little. Ask yourself which choice will make for the better story, or which choice will make you prouder of yourself in the morning. Maybe that’s going to the loud late-night spanking party, or maybe it’s ducking out early to have drinks with just a couple people at the hotel bar.

Cons can feel like a wacky dream, full of implausible situations with implausible people. If you receive an invitation that sounds fun but a little intimidating – like “Hey, come smoke weed with us in the parking lot!” or “We’re gonna play Strip Scrabble in my hotel room; wanna come?” – don’t just write it off immediately. It might lead to flirtation you would’ve regretted passing up.

Shoot your shot. Here’s what it ultimately comes down to: a conference is a time-limited opportunity to have lovely experiences with people you rarely get to see. If you want something to happen and it hasn’t happened, you can either give up, or take some action. If you’re getting flirty vibes from your crush but neither of you has taken much initiative, and the end of the con is coming up fast, it might be time to get real and make your move.

The best approach to this is going to depend on you and your crush and what kind of people you are. However, I asked some fellow introverty blogger friends, and their opinion matched mine: I think the best way to “shoot your shot” at a con would be to send your crush a DM saying something along the lines of, “Hey! You might have noticed by now: I think you’re super cute/charming/fantastic. If you feel similarly, would you like to [make out/play/hook up] sometime before the con ends? I’d regret it if I didn’t ask. If the answer is no, I’ll totally understand and won’t be offended at all, and I’ll still think you’re great!” My blogger friends agreed that a private message is better than a public tweet or an in-person convo for this, because it gives them an opportunity to think things over and phrase their answer carefully if they need to.

Have you ever had a conference crush? Did it ever turn into more than that?

5 Times Kink Helped Me Love My Body

One of kink’s many magical qualities: you have to keep talking about it. All the time. There are no assumptions, no scripts, nothing for which consent is presupposed. At least, not the way I prefer to do it.

My first dominant fuckbuddy teaches me this. Our sext exchanges have consent conversations built right in. “I like restraining partners with chains,” he says. “I’m not a fan of being choked,” I say. “Teach me how to make you come with a toy,” he pleads. “I think I want to sit on your face,” I hypothesize.

I get good at asking for what I want. In the throes of subspace during my BDSM hookups, sometimes I lose my words, unable to form sentences longer than “Yes,” “No,” or “Harder” – but the more I try, the easier it gets. Though power exchange often leaves me literally gagged and silenced, it also makes me better at speaking up when I need to.

So after my fuckpal makes one too many vagina-shaming comments in my presence, I decide I don’t want to see him anymore. He’s not into period sex, he’s not into “excessive” wetness, he’s not into falling asleep next to me unshowered after sex – and while it’s fine for him to have his boundaries, it’s also fine for me to have mine. I want sex while I’m bleeding, wet, and/or dirty. My sexual menu just doesn’t feel complete without those things. A partner who can’t unabashedly adore my body in all its various weird states is not a partner I want to give myself over to.

So I tell him. “I don’t think I want to do sex/kink things with you anymore. I’d still like to be friends, though.”

He’s a little taken aback, but fine with it. My sigh of relief is immediately followed by a rush of pride: I identified an unmet need in my life and did something about it. I owned my desires and asserted them. And now I’ll no longer have to bang someone who makes me feel, in the smallest and saddest of ways, like my body is to be tolerated and not to be devoured.

I’m wearing nothing but lingerie in front of a crowd at a sex club. A photographer is snapping pictures. It’s terrifying – but I’m less scared than I thought I’d be, because a hot, brassy babe is bossing me around.

“Bend over and show the crowd your ass,” she barks. “There you go. Good girl. Doesn’t she have a great ass, folks?!”

The crowd bursts into applause, whoops, and yells of affirmation. Apparently they agree with her. I grin and laugh and blush and laugh some more.


I’m midway through a blowjob when my one-night stand starts to get antsy. “Come here,” he growls. My eyes flick upward, quizzical. Can’t I just… stay down here?

I climb up his body to kiss him. “No. Higher.” I straddle his belly. Is he really asking me to…? “Higher,” he commands again. Yep, I guess we’re doing this. I slide over his chest until my vulva is settled over his mouth. He wraps his big strong hands around my thighs and hips and pulls me toward him. My clit has no choice but to tangle with his tongue. I gasp and clutch at the headboard. Fuck, he’s good at that.

I’ve never sat on someone’s face on a first date before. Usually I date someone for months before I let them invite me onto their face. It’s just a lot: they get a mouthful and noseful of pussy, plus an eyeful of belly and underboob and double chin. I worry I’ll crush them with my chubby body, drown them in my juices, embarrass myself with unladylike sounds. I need to believe someone 100% wants me, in all my weird and overwhelming glory, before I’ll feel comfortable giving them that. This requires at least a few months of dating… or, apparently, a well-placed command from a one-off hookup.

See, when you command me to do something, I have to assume you want that thing. Maybe this is part of why I’m submissive: my irksome sexual anxiety insists I’m unattractive, unless and until someone cute is there to insist on the opposite. So, while “I love your body and find you gorgeous” is a highly effective line, “Come here and sit on my face immediately” achieves more-or-less the same purpose.

Sometimes there’s no time to worry about whether I’m “attractive enough,” because I’ve been given an order and I have to do what I’ve been told immediately. It’s important, after all, that I be a good girl.


We’re hours deep into our second date, lying on his bed in the hazy afternoon sun, stoned as fuck. The weed, as per usual, is working its magic: I am craving pain, knowing it will permute into pleasure. I turn to this boy I only met three days earlier and say, slyly: “I want you to spank me.”

I see his reaction in slow motion, because weed does that. He bites his lip, smirks, breaks into a grin. And then he says it: “With what?”

Everything else is slow and so too is the spread of goosebumps over my entire body, from my shoulders down my arms and all down my back. His question outs him as a true kinkster, one experienced with impact play and potentially owning a collection of implements. But what really excites me about this question is the tone of voice in which he said it: dark, rough, and absolutely dripping with want. I can tell he cannot fucking wait until I’m over his lap. And I don’t want to wait, either.

“Your hand, please,” I reply, and hitch up my skirt.


I’ve always hated my butt. The jiggly cellulite, the amorphous shape. I grew up on a steady diet of SuicideGirls and vintage pinups, and coveted those perfect, round butts. Mine did not look like theirs.

I didn’t know, when I got pretty pink bows and the words “good girl” tattooed on my upper thighs, that they would unravel years’ worth of insecurities in one fell swoop. Overnight, I went from trying to orient my body so partners couldn’t see my butt during sex, to openly showing it off and asking gleefully, “Do you like my tattoos?!” It felt odd to go back and look at photos of my backside pre-tattoos – not only did I dislike how it looked, but it also simply didn’t seem like it was mine.

One summer evening, I’m hanging out in an upscale Toronto sex shop with my friend Taylor. He’s teaching an impact play class, and I am the demo bottom. After the introductory preamble, it comes time for me to get spanked. “Should I take my dress off now?” I ask, and Taylor nods. I pull my simple cotton dress off over my head, revealing a matching set of lingerie underneath, and bend over the shop’s grey sofa to show off my ass to the crowd. Taylor explains how to wield a paddle, and then demonstrates. I smile through my grimace of pain, because I know I can handle this.

“You looked so confident tonight,” my boyfriend tells me later when I’m tucked into his bed, “just wearing lingerie in front of all those people.” He’s running his hands all over me and it’s hard to focus on his words, but when I do clue in to what he’s said, I feel proud.

“It wasn’t hard,” I say with a nonchalant shrug. It would’ve been, five years ago, or even one year ago. It would’ve made me cringe and blush and doubt myself. But tonight it was easy. Because I love my body and don’t care if other people don’t.

Just as long as the people I’m dating/kissing/fucking think I’m hot. And judging by the way my boyfriend is groping my ass and nibbling my neck, I would say that he does.

 

This post was sponsored, and as always, all writing and opinions are my own!

8 Ways to Explore a Sexual Fantasy (Without Actually Doing It)

Sex can be scary! I find straight-up vanilla sex intimidating sometimes – bodies and expectations and insecurities, oh my! – and kink can be even moreso. Especially when I’m thinking about introducing a brand-new activity into the equation.

It’s often easier to introduce a new kink act to a partner, I find, if you’ve previously explored that act in other ways. It’s a bit like how you’d probably practice a striptease in the mirror a few times before debuting it for your partner: you want to get comfortable with it yourself before exposing it to the eyes of others.

With that in mind, here are 8 ways you can explore that new fantasy that’s been bouncing around your brain – without actually going whole-hog and doing the damn thing. You can always get to that part later, if you want!

Fantasize about it. This is, of course, a common way to flesh out any new ambition, sexual or otherwise. Some science suggests fantasizing even helps you actualize your desires, like how some athletes visualize winning before they even get on the field, and have noticeably better results when they do. Play with your new kink in your mind while you masturbate, and see how it feels. If it turns you on as much as you had hoped, that might be a green light for you to bring it up with your partner(s)!

Journal about it. Whenever I’m considering making a change in my life, I find it helpful to write out all my thoughts about it. If you’re intrigued by a kink that’s new to you, you might want to spend some time unpacking why this kink intrigues you. You could also make a pros and cons list, write a script for how you’ll bring up this desire to your partner, or even write some spicy erotica featuring your kink of choice. All these approaches will help acclimatize you to a scary new sexual ambition.

Talk to someone about it. If you have a non-judgmental friend who’d be willing to hear you out, you might find it comforting and clarifying to discuss your new desire with them. You could also call a service like Peachbooth (which is free!), where a dirty-minded professional will talk out your fantasy with you or even roleplay the scenario of your dreams. You know a pro won’t judge your kink or rebuff you for bringing it up, so this can be a safe and comfortable first step into your new kink.

Listen to someone else talk about it. Search for Peachbooth clips about your kink of choice, and you’ll get to hear other people discussing it like it’s no big deal – not to mention hot. This can help normalize your new desire in your mind, so you won’t feel so scared to bring it up “in real life.” There are also tons of sex podcasts (look ’em up on iTunes or another fave podcatcher) which can serve the same purpose.

Read instructional books about it. There are so many great kink books out there. Type the name of your new kink – or some adjacent search terms – into Amazon or another bookseller, and see what comes up. Books are helpful not only for fantasy purposes but also for general safety and preparedness: if you’re pursuing a potentially dangerous kink like fireplay or knifeplay, you’ll want to know what the risks and best practices are before you attempt it!

Watch porn about it. We live in the era of internet porn – might as well take advantage of that! As per the infamous Rule 34, if you can conceive of a subject, there exists porn about it. Get on Google, or your favorite porn site, and do a search for whatever naughty notion is occupying your mind. You might learn something new about the activity you’re looking to explore – or about yourself!

Read erotic literature about it. Flip through erotica anthologies at the bookstore, do a search on Literotica, or even browse a fanfiction site like Archive of Our Own. Text-based erotic media can be more illuminating than traditional porn because you get a glimpse into the characters’ minds and motivations, which might help you understand your newfound desires more deeply. (Plus, how fun is it to read about Sherlock Holmes getting pegged or flogged or fucked by tentacles or whatever?!)

Talk dirty about it during sex. Even if you’re not brave enough yet to put on that schoolgirl costume and hand your partner a wooden ruler (for example), you can still weave pieces of that fantasy into your sex life together. You could gasp “Have I been a bad girl?” in between kisses, or drop a “Sir” into your dialogue and see how your beau reacts. This is a lower-pressure approach than rolling out a detailed script and storyline for the fantasy you hope to enact.

How do you like to explore a new kink before you try it out in real life?

 

This post was generously sponsored by the folks at Peachbooth. As always, all writing and opinions are my own.

Monthly Faves: Bondage & Besties

July of last year was an out-of-control amazeballs month for me sexually. This July was nice too, in different ways. Here’s some of what I got up to…

Sex toys

• This month I was sent the Zumio, an oscillating clitoral stimulator similar to the Eroscillator but way more pinpoint (full review forthcoming!). I honestly was expecting to hate it, but… I don’t. It’s so intense that I usually only use it on the first setting and through panties – which also means it lends itself well to “forced orgasm” kink scenarios. At one point this month, my boyfriend held the Zumio on my clit while fucking me with the S-Curve, and I practically died of pleasure…

• Speaking of cool shit my boyfriend did to me: he surprised me one day by putting my collar on me and then chaining it to my under-the-bed restraints so I couldn’t move. Then he jammed my Liberator Jaz under my hips and went down on me until I came. Woof.

Fantasy fodder

• A couple times this month, my partner alluded to cunnilingus as an endurance-based endeavor – “I wanna go down on you for a long time,” “I’m not gonna stop until you come,” and so on – and it reminded me of how soothing (and hot) these kinds of reminders can be. One of my number-one sexual anxieties is “taking too long” to come, so it’s enormously helpful when a partner pre-empts those worries by essentially telling me they want me to take a while.

• I did two things this month that are typically associated with “femdom” – pegging and facesitting – but because I did them with my mega-dominant boyf, I did not feel dominant at all. I felt like I was being his servicey little good girl, or like I was being served to him on a proverbial silver platter. Friendly reminder: dominance and submission are not baked into any particular sexual act; they’re attitudes you can bring (or not bring) to any act you choose!

• Here’s a good sentence that came up in my fantasies a lot this month: “I wanna feel you come on my cock, little one.” Oof. ‘Nuff said.

Sexcetera

• Some of my work elsewhere this month: Kinkly asked me to write about the significance of collars for me as a submissive. For my friend Taryn’s blog, I wrote a guest post about things to consider before entering a DD/lg relationship. I detailed some surprisingly common sexual fantasies for Ignite and wrote some beginner G-spot tips for Peepshow.. On our podcast, Bex and I talked about polyamory, penises, and edgeplay, and we interviewed our friend Taylor J Mace.

• Orgasm statz: I had 33 orgasms this month (go me!), bringing my total for the year up to 195 thus far. 14 of those orgasms (42.4%) were from partners, including one from a partner who had never made me come before this month (yay!).

Femme stuff

• I got some new tattoos toward the start of the month: “THIS TOO” + “SHALL PASS” on the insides of my wrists. This felt impulsive – I went for a walk-in appointment at my tattoo shop early one Wednesday morning – but actually it wasn’t that impulsive: I’d been thinking about getting these tattoos for months, and decided it was finally time. They serve as an important reminder for times when I’m feeling anxious, depressed, or otherwise out-of-sorts. So far I’m finding them very helpful!

• After making a Lush trip this month, I’ve gotten back into an old fave, the Mask of Magnaminty, and been swoonin’ over a new acquisition, Miranda soap. Oh Lush, you always do me right.

• I’m so smitten with my new clitoris necklace from Animal Hair. They also make dick earrings and a necklace covered in legs, among other things. Cuuute!

Little things

Learning about sex surrogacy and sexological bodywork from Caitlin. Longform improv. Queer femme babes. Getting super stoned (and sunburned) in Trinity Bellwoods. The Adventure Zone. Telling my boyfriend “I love you” for the first time (aww). Sexting while high. My brother’s band’s new music video. “Never really knew if I did something wrong; all I ever heard was it wasn’t my fault.” Feminist children’s theatre. My boyfriend making us coffee to thoughtfully sip while we have goofy conversations in the morning. Angels in America. Writing with fancy pencils. Creativity during hypomania. Bite marks. “Babe, can I put my passport and butt plugs in your bag?” Diner breakfasts with Bex. Weed breaks on an Airbnb stoop. Nerdy income stats. Sexy jazz.

3 Sexual Fantasies I Hope to Act Out Someday

One of the best things about working in sex media: you’re constantly exposed to new kinks and scenarios, and therefore, if you’re lucky, you’re constantly coming up with new sexual fantasies to lust after.

I know what my main kinks are – the basic building blocks of my psychosexual makeup – but I’m always adding new things to my peripheral list of “hmm, maybe someday” kinds of kinks. Whether I’m reading fanfiction or classy erotica, watching art porn or raunchy amateur clips, discussing friends’ recent sexploits or telling them about mine, I’m always filling my head with new ideas for my “fucket list.”

Here are 3 fantasies I’m slightly fixated on lately…

An MFM threesome. I’ve had several threesomes, but all were with a man + either a non-binary person or another woman. They were all absolutely delightful, but gosh, I’d love to be the focus of two dudes’ focus at once. Maybe a dominant guy would tell a submissive guy what to do to me; maybe one dude would worshipfully go down on me while the other fucked my face; maybe we’d even work our way up to double penetration. (Ambitious!) Whatever the situation, I bet I’d love being the centre of attention.

Professor/schoolgirl roleplay. Maybe I’ve watched too much dialogue-heavy situational European porn, or maybe it’s just my inner teacher’s pet showing, but I’ve always had a thing for sexy teacher/student dynamics. I fetishize red apples used as ballgags and wooden rulers thwacked against nubile butts. I feel sexiest and sassiest in short thigh-baring skirts, and I get a little weak in the knees for tweed blazers with elbow patches. Someday I hope a well-dressed domly person (consensually) bends me over a wooden desk, tells me I’ve been a bad girl, and gives me an opportunity to earn some extra credit…!

Erotic massage. For as long as I can remember, I’ve eroticized the idea of someone deftly and expertly getting me off, like it’s their fuckin’ job – and in this fantasy, it is. Depending on my mood, sometimes I picture the masseuse actually finding me attractive and getting turned on in a highly unprofessional way – or sometimes I just want them to be stony and stoic, stroking me on autopilot until I fall apart. Either way, it’s a fantasy so hot that I tense up from arousal… and probably need a good massage to work out those kinks, if you know what I’m sayin’.

What fantasies are haunting your sex-brain recently?

 

This post was generously sponsored by the folks at PornDoe, and as always, all writing and opinions are my own!