Links & Hijinks: Flirting, Crying, and David S. Pumpkins

• Ask Polly has some advice on what to do if you want to date men but also you hate men. “Dating, like all arbitrary, tedious, pointless social exercises, requires a higher level of Zen. Surrender to the excruciating nothingness of the task at hand, and try to enjoy it. Yes, most men are shit. But you are not taking an exhaustive survey of most men. You are looking for one good, kind, exceptional man. They exist.”

• These tools for recovering from sexual trauma are neat as hell!

• Not exactly relevant to my blog, but oh well: I enjoyed reading this oral history of the David S. Pumpkins SNL sketch. It made me think about how we’re drawn to silly, meaningless entertainment in times of sociopolitical turmoil, and also about how fucking great Tom Hanks is.

• You can use the teachings of Aristotle to get someone to go on a date with you. Hmm!

• Luna told the story of moving her massive sex toy collection when she moved houses. “The thought of a box of fantasy toys tipping over and disgorging its colorful contents in the back of my dad’s SUV is the stuff of nightmares.”

• Girl on the Net wrote about crying after sex and it was so beautiful and relatable that I cried, too.

• What does it mean to be a “kink lifestyler” and how do you know if you are one?

• Here are a bunch of stories about dicks getting stuck in things.

• What can you do when your social media addiction is curbing your creativity? This article is chicken soup for the creative soul, truly. “Sometimes the most skilled, unique, emotional writers are the ones who struggle with feelings of inadequacy the most,” Heather writes. “Refuse to imagine what will impress other people. Seduce them into loving exactly what you have to give instead. Savor your craft and enjoy yourself.”

• Here’s how to prepare your bed for sexy guests.

• Sammi’s Satisfyer review includes a cool sex toy hack that will be of particular interest to transmasculine folks. Gotta love the ingenuity of sex nerds!

• I shrieked with laughter watching this video of Jeff Goldblum reacting to tattoos of himself.

• Would hiring a sex worker help predatory men (e.g. Weinstein, Spacey, CK) work through their fantasies? Experts weighed in. And then Alana Massey weighed in. Lots to think about here.

• Miles Klee makes a case for period sex. I think I’ve reached a point where I can no longer date folks who are squeamish about the crimson wave…

• I’ve been fascinated by fear play lately so I loved Taylor’s post about why they love it.

• I loved reading about this vibrator that tracks your orgasm statistics. Sex nerdiness, activate! (Also, why don’t I own this toy?!)

• Where does the slang term “fap” come from?

• If you’re a dude who flirts with women, or would like to flirt with women, read this guide, please. It’s very good.

Do I Have a Wink Kink?

As with many kinks, it began with the thought: “I just like it. I don’t think it’s a sex thing.”

I’ve always reacted with glee to being winked at. I suppose this is a not-uncommon reaction – they’re intended as an expression of flirtation, humor, or solidarity, after all, so they’re intended to create a positive feeling in the recipient. But the degree of my reaction seems… unusual. I’ve never quite been able to pin down why. Kinks, after all, are never simple.

As with many kinks, too, its unfolding turned me into a bit of a creep. Sometime around the end of 2015, I started occasionally mentioning it while out on first dates: “I have a thing about winks,” I’d ambiguously admit if the subject of flirtation or odd romantic tastes came up in conversation. Sometimes, if I got tipsy enough, I’d just ask outright, “Do you have a good wink?” The question caught my dates off-guard. They’d not considered this before. I see now that I was doing a thing akin to when foot fetishists get a little too curious about my shoe collection or ageplay fetishists call me a “little girl” without asking – i.e. things people do in service of their kinks that aren’t strictly okay without consent – and I feel bad about it. I wasn’t thinking of it as a kink then.

I went out for drinks once with someone I had strong feelings for, and inquired at some point about his wink. He was a shameless show-off of a man, theatrical and broad, so he launched into not only a wink demonstration but also a verbal lesson on how best to wink (“You gotta do it so fast that the other person almost doesn’t see it, and wonders, ‘Did he just wink at me?!'”). My burgeoning fixation crossed paths with my teaching and learning kinks, and the result was a whole lot of giggling and blushing.

That same friend once pounded me with my favorite dildo, mercilessly, masterfully, as hard as I wanted. I squeezed my eyes shut as I shouted my orgasm into the heavy, humid air. When I returned to earth, I opened my eyes to see my fuckbuddy staring at me intensely, a look of lusty concentration on his face – and then he fucking winked at me. I actually moaned. If I didn’t know it was a kink before that, it was that moment which solidified it.

Friends started sending me gifs or YouTube clips of good winks. On days when I felt sad or unloved, I’d put out a call for winks on Snapchat or Twitter, and watch my phone blow up with flirty babes.

I told a new beau he had a good wink, and he kissed me tenderly for long minutes, occasionally leaning back just enough to wink at me between kisses. He held my face still in his hands, so I could not look away. It was like a forced orgasm scene, but more intimate, and more “erotic tease” than “whole hog.” I died a little bit.

I went to a house party, and drank enough to get me into extra-giggly mode. Somehow, word of my penchant for winks got out around the party, and suddenly, random people were coming up to me just to wink at me and see my reaction. “Hey Kate,” they’d say, to get my attention, and then I’d be accosted with a razor-quick one-eyed straight shot of glee to my heart and genitals. It was a strange sensation, strangers and acquaintances knowing this little shortcut; it felt intense, almost boundary-crossing. I felt the way I do when someone spanks me who I don’t quiiite trust enough for that yet: breathless, shaken, turned on but undone. I wasn’t entirely sure I liked it.

One night I went on a first date at a sexy storytelling event, and afterward, the date and I stuck around to chat with my friends. One of them knowingly threw a wink my way, and when I had my predictable giggle/shriek/blush reaction, my pals explained to my date that I have a thing about winks. I was quick to add that it gets strange when people think they can just wink at me willy-nilly. “I’d rather they get my consent first,” I explained. “Ugh, that sounds so weird, doesn’t it?”

My date, an experienced kinkster, shook his head with solemnity. “No, it doesn’t.”

Fast forward a few weeks, and we were dating and fucking and falling in love. One day in bed, after sex, he lay beside me stroking my hair and staring into my eyes. “Do you think we’re at a point yet where I could wink at you?”

The thoughtfulness of the question touched me. I may have cried a little bit. And then a little more, laughingly, when I realized what a silly thing it was to cry about. But it was the gesture that had affected me: the caring about my comfort, the remembering of inane details, the wanting to make me happy but only on my terms.

I nodded. “Yeah, you can.” He did. I giggled, and my heart clenched up in that now-familiar way. But it was a world away from those stranger-winks at the party. Like the difference between oral sex from a random hookup and oral from a long-term partner who knows your body and your brain inside and out, there was a sense of intimacy and mastery to it that pulled me inside the moment, rather than making me want to nervously run away from it. Each wink from him was like a slap in the face – but the consensual, cathartic, kinky kind.

Now that that relationship has dissolved, actually the only piece of that man I still own is his wink. Once, at my request, he offered me the incentive of a short video of him winking if I finished a big project I was working on. Motivated anew, I drudged through it, and sent him the completed file. “Wink, please!”

The clip still sits in my Twitter DMs, haunting me if I scroll back far enough. It’s only three seconds long, but it’s three seconds of someone who loved me, showing me just how much he did.

Kinks are never simple.

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 Ways I Flirt As a Submissive

1. Unprompted service. Three weeks ago, we went out to lunch and you ordered a Mill Street lager. Tonight, I show up for our scheduled fuckdate at your house, carrying a six-pack of Mill Street lagers. If you were a vanilla boy, maybe you’d seem surprised, or embarrassed that you didn’t get me anything in return. But you’re a dom perv who gets off on my diligent service, so you just take the beers from me, put them in the fridge, and say, “That was very good of you.” I quiver in my boots.


Halfway through explaining to a customer how a particular vibrator works, you accidentally drop its instruction manual on the sex shop’s tile floor. Without speaking, interrupting your pitch, or even giving it any thought, I kneel down and scoop up the booklet from under the toy counter where it fell. “Oh, you don’t have to –” you start, but then I hand it to you from a kneeling position before you, we lock eyes, you set your jaw, and you murmur with a small smile, “Thanks.”


2. Complimenting your dominant qualities. “Time to sweep and mop,” you bark, when there’s an hour left til closing time. Then your tone softens: “Sorry, that was bossy. Time to sweep and mop, please.

En route to the supply closet to grab the broom, I retort over my shoulder, “It’s okay; I like it when you’re bossy.” I hear the pause as you process this, and then you reply, “I’m not sure how to take that…” I grin. And then I get to sweepin’.


Your cat is being an asshole: scratching at the door, yowling incessantly, fucking shit up. You say his name sharply, in the tone of a dad who’s just walked in on his kid drinking chocolate milk straight from the carton.

“I’m really weirdly into it when you get dom-y with the cat,” I enthuse swoonily. Your eyes slide over to me and narrow in mild confusion. “Yeah?” you say, and I nod, wishing you’d speak to me sometime with the sternness you reserve for misbehaving calicos.


3. Alluding to past experiences. At her request, you hit our friend with a leather riding crop so she can see what it feels like. “Wow! I’m surprised that didn’t leave a bruise,” she says, minutes later, as she examines the spot in a mirror. “Crops don’t usually bruise that much,” you and I both start to say, in different words but echoing the same sentiment. Our eyes meet. I feel a hot pop of recognition – the electric familiarity that clicks into gear when kinksters spot fellow kinksters. Oh, hello.


My friend finishes our lengthy spanking session, and I push myself up off the sex club’s gorgeous leather spanking bench, freshly and darkly bruised. “How was that?” you ask. “A good warm-up?” It’s a joke, but it’s also a challenge, a barometer, a test.

“I’ve had worse,” I reply with a saucy shrug. And then I take the paddle my friend was hitting me with and place it in your hands. I don’t know what you’ll do with it, if anything, but I’m curious to find out.


4. Honorifics. We hug goodbye outside the diner after a cozy breakfast. “Be good,” you tell me as we part ways. I shout back, “Yes, sir!” and watch the bemused smile bloom on your face.


We’re at a party, and I make a dumb joke that doesn’t land quite right. Someone calls me an awkward turtle, and I shake my head and inform them, “I’m not a turtle. I am an awkward bunny.

You look at me with cool appraisal and say, “A bunny, huh? Yeah, I can see that.”

How did you know that “bunny” is one of my kink honorifics, despite the totally vanilla nature of the conversation in which it appeared? I have no idea. You have sub-dar, apparently. And it’s working. I attempt to swallow the sudden dry lump in my throat, and reiterate: “Yeah. I’m a bunny.”


5. “Is that an order?” We tread water in the heated pool under the stars. “Is the deep end really deep?” I ask conversationally, and you say, “Nah. You could definitely swim to the end and back, no problem.”

I bite my lip. “Are you telling me to do that?”

“No,” you say immediately, “you don’t have to,” and I exhale the breath I didn’t realize I was holding. I do it anyway, like it’s a dare from the dom you unfortunately aren’t.


Plotting a threesome via text, I mention that multiple orgasms aren’t exactly in my wheelhouse. “What if you took a break from masturbating for a few days beforehand?” you posit. “Maybe we could get 3 out of ya ;)”

I pause, stare at my phone screen, try to breathe. And then I type a phrase so loaded for me, I’m almost scared to make it real by committing it to text. “Is that an order? ;)”

There is a minute of silence during which I become convinced I have scared you away forever by wanting too much from you, climbing too high on the kink ladder while you’re still meandering through the vanilla wilds below. But then your reply comes back: “That is an order. Are you gonna be a good girl and wait a few days for my cock?”

I scream at my phone, throw it across the room, and cover my face with my hands. I am going to be such a good girl for you, sir.

How Meta-Communication Can Make You a Great Flirt (Even If You’re Shy)

For years, I said, “I’m a bad flirt!” when what I really meant was, “I’m too shy to flirt!”

Then I got better at it, but I still said, “I’m a bad flirt!” when what I really meant was, “My flirting style is dorky and non-traditional, but still charming!”

Nowadays, though, I’ve learned more about flirting and the various ways it can be done – and I finally recognize that my approach to flirting is both valid and effective. My eyes widened when I first encountered the term “meta-communication” – i.e. communicating about communicating – with regards to flirting, because that is totally what I do. It has worked for me, whether I was engaging in monogamous or polyamorous dating, and I think it can work for you too!

Here are some of my favorite tips for flirting via meta-communication…

Acknowledge your flirting as such. This is effective for the same reason that it works well to use the word “date” when you ask someone on a date: it makes your intentions crystal-clear, sets your flirtee’s anxieties and uncertainties at ease, and – when done well – makes you come across as a smooth, bold, fearless flirt.

Examples:
“Is this a good time to flirt with you?”
“I’m really enjoying flirting with you; maybe we could do this more later?”
“Sorry, I get really flirty when I’m [tipsy/happy/super into someone].”
“Can I try out a ridiculous pick-up line on you?”
[cartoonishly over-the-top eyelash-batting, smouldering glances, etc.]

Acknowledge how you’re feeling. Flirting is so often portrayed as a performance, where you have to be an actor or a puppeteer – but it can be even more delicious to let your flirtee see what’s behind the curtain. You come across as more human and real when you cop to your emotional processes – and this also helps build rapport and trust, because your flirtee knows if you own up to your feelings, you’re likely to also tell the truth about other things later on.

Examples:
“I get really nervous around you ’cause you’re so cute!”
“If I wasn’t so shy, I’d make a dirty joke about what you just said, but…”
“I really wanna flirt with you, but I’m not sure I’m getting that vibe from you, so I’ll back off.”
“If I wasn’t so [tired/anxious/busy], I’d be flirting so hard with you right now… Maybe next time?”
“Sorry if I seem unfocused; I just can’t stop thinking about how good-lookin’ you are!”

Propose a hypothetical. This is a low-pressure way to gauge your flirtee’s reaction to things you want to do or say, or just to you in general. You’re giving the other person space to turn you down if they want to – but also giving them space to respond positively if that’s how they’re feeling.

Examples:
“What would you say if I told you you look super handsome in that suit?”
“What would you do if I said I wanted to kiss you right now?”
“I wouldn’t be mad if you gave me your phone number… In fact, I might even be thrilled!”
“If someone wanted to flirt with you but was really shy, what would be the best way for them to do that?”

Give them an opportunity to take things further. Consent is just as important in flirting as it is in sex, and you want to give your flirtee the same freedom to express or revoke consent that you’d give them if the two of you were bangin’. Much like the first-kiss technique advocated in the movie Hitch (“Go 90% of the way, then let her come to you“), this type of flirting clearly expresses your interest in the other person but leaves them room to decide how far they want to take things.

Examples:
“There are a lot of saucy things I want to say to you right now, but I’m not sure if it’s appropriate…”
“If I have another drink, I’ll probably get reeeal flirty with you… Think I should?”
“Let me know if you’d ever want to go out on a date sometime; I’d love that!”
“I bet you’re an excellent kisser. Maybe I’ll find out someday; who knows?”
“I have to go [talk to another friend/do something else], but come find me later if you want to be shamelessly flirted with some more!”

Here’s what’s important to keep in mind with all of these suggestions: flirting is very dependent on context, environment, and preexisting rapport. A lot of these lines won’t work if you just bust ’em out unprompted. But if you already have a good connection with someone, they seem potentially into you, and you want to express your interest in them without overwhelming them, some good meta-communicative flirting can be just the ticket!

Extra resources for flirting keeners:
• Reid Mihalko and Cathy Vartuli on being a better flirt, how to flirt when you’re shy, “the innuendo game,” and building rapport.
• Reid Mihalko talking about flirting on a swingers’ podcast.
• The School of Life on why, when, and how to flirt.
• Bex on being a flirting fetishist.
• Social anthropologist and “flirtologist” Jean Smith on the science of flirting.

Heads up: this post was sponsored, and as always, all writing and opinions are my own.