What to Wear to Your Break-Up

What I wore to my last major break-up, in 2014
What I wore to my last major break-up

Break-ups are hard. That’s true for anyone, and it’s true for me. I have an anxiety disorder. That means my brain’s fear-o-meter is out of whack. And that means I often worry about things that no neurotypical person would ever worry about as deeply as anxious folks do. For example: what to wear to break up with someone.

There is such a delicate balance to be struck in this sartorial decision. You want to wear something that makes you feel strong and brave, shoring up your resolve so you don’t chicken out. You want to look good, but not so attractive that your babeliness is a slap in the face to the person you’re dumping. You want to be prepared incase your soon-to-be-ex bursts into tears (or you do) and needs to wipe their snotty face on something. You want to dress appropriately for the temperature and tone of your break-up’s setting, whether that’s your beau’s apartment, a classy bistro patio, or a bustling street corner. You want your choice of footwear to enable a quick getaway, whether that’s needed because of emotional awkwardness or (god forbid) actual threats or violence from your scorned would-be ex. And you don’t want to wear anything that could be interpreted as a sign of lingering feelings for your dumpee, like a T-shirt you inherited from them or a necklace they bought you.

The last time I broke up with a serious partner, it was the sticky height of summer in 2014. I tucked a white tank top into a pink skirt, and put my hair in a ponytail with a pink scrunchie. Hot pink is one of my “power colors,” a shade that makes me feel strong and put-together, which I knew I’d need – because emotionally, I was a mess.

I slipped on some plain black leather flats and departed toward where I’d agreed to meet my boyfriend. About ten minutes into my walk to the subway station, I realized that in my frazzled trance, I’d forgotten my wallet at home. It was too late for me to run back and get it if I was going to meet my partner on time, so instead I just power-walked all the way to my destination. I arrived dripping sweat and out of breath.

When I actually delivered my little break-up speech, I broke down crying. I’d been with this man for three and a half years, and he was my best friend; saying goodbye to him was no easy task, though I knew it was necessary. He asked me if it would be weird if he hugged me, and I said no. He squeezed me tight, one last time, until my breathing slowed. And then we said our teary-but-amicable goodbyes and went our separate ways.

I wished I’d brought a scarf, so I could’ve wiped my wet face on that instead of on my beau’s shirt. I wished I’d brought sunglasses, so I could’ve hid my eyes as I wept all the way home. I wished I’d remembered my damn wallet. But hey, at least my clothes looked cute.


Here are some outfits and the fictional babes who wore them to their break-ups… (Idea reverently pilfered from Gala Darling, who’s written similar posts about first dates, New Year’s Eve, and dream girls!)

Nora wasn’t going to take any of his shit anymore. She showed up at James’ house with a box of his stuff slung under her arm, and kicked his door a few times with her steel-reinforced boot toe instead of knocking. She’d probably scuffed the paint. Fuck him, he deserved it.

When he opened the door wearing his plaid flannel PJ pants and nothing else, she rolled her eyes and thrust the box into his torso, knocking the wind out of his dumb face. “We’re done,” she barked, and turned on her heel.

“Why?” James sputtered. A Ninja Turtles action figure had fallen out of the box and he bent down to pick it up. “What did I do?”

“You know perfectly well what you did,” Nora snapped without turning around.

When she got back to her car, she caught sight of herself in the rearview mirror, all smudged eyeliner and mussed-up hair. She looked pissed, but she looked foxy. She dug her favorite lipstick out of her bag and reapplied it, slowly, carefully, with the precision of a woman who wants to look hot for the next chapter of her life. Once her lips were perfect, she revved up the car and embarked on a new adventure, joyfully Jamesless and unencumbered.

“I’ve always hated you in those glasses,” Jackson said when Audrey sat down at the desk next to his. “Don’t you have contacts or something?”

Audrey could feel their classmates watching her. Granted, lecture hadn’t started yet, so there was nothing else to watch, but the mini-drama of Jackson and Audrey’s Tumultuous Romance had been a key source of entertainment these past six weeks in Existentialism 101.

“I like them,” she said simply, beginning to unpack her notebooks and pens.

Jackson made a noise somewhere between a scoff and a snort, and that was the final straw.

“I don’t think I want to see you anymore,” Audrey muttered. And then, a little louder: “We’re just not a good match in so many ways. We disagree on the feminist significance of Simone de Beauvoir, for example.” She cleared her throat. “And I’m tired of writing your essays for you. You should do your own work; the rest of us do.” By this time, the other students were full-on staring. The professor had arrived, and seemed interested in this choice piece of information too. “Oh, and you’re an asshole,” she added with finality.

Gaping at her and leaning way back in his chair, Jackson lost his balance for a moment and spilled onto the floor with a clatter. Audrey wordlessly gathered up her notebooks and pens and moved to a desk at the front of the room. The lecture today was going to be about Dostoevsky and she wanted to absorb every word.

“I just don’t think I’m ready for this,” Jenny said with a sniffle. They shouldn’t have met in a park; the hillside was covered in grass and Jenny was allergic to grass. That was the only reasonable explanation for her watery eyes and nose. Right?

“It’s okay, princess,” Evelyn murmured, clutching her little one against her chest. “We probably rushed into this. I should have taken things more slowly. I’m sorry.”

Jenny shook her head and pressed her face against the older woman’s clavicle. She felt safe there, but it was a conflicted sort of safe. “No, it’s not your fault,” she stammered. “I’m just… not as ready as I thought I was. I’m still not over Mel. I should have been more real with you about that.”

Evelyn kissed the top of her princess’s head and held her tighter. “I understand,” she said. “I’ve been there before.”

They sat in silence for several long moments, Jenny’s wet breaths the only sound in the air. Then she said: “Can I keep my collar?” Her hand traveled to it reflexively, fingers hooking on the heart-shaped steel clasp.

Evelyn laughed softly. “Of course, baby. It’s yours. You can keep it even if you don’t think we should see each other anymore.”

Jenny exhaled deeply against Evelyn’s neck, her breathing starting to return to normal. “I might need it again someday,” she whispered. “You know, when I get over Mel and I’m ready to give this another shot.”

Evelyn smiled. The sun had started to set.

Alex had never hyperventilated in an airport before. Lots of other places, sure, but never an airport.

Sleepy passengers piled out of the arrivals door, fresh off a flight from Lisbon. Fuck, this is gonna be bad, Alex thought, but then, she always thought that. That was just how her brain worked.

She spotted Matt, weary-eyed with suitcase in hand, and a bolt of panic shot through her belly. Fuck, fuck, fuck. She had to do it. She had to. It was scary but she had to do it.

“Matt!” she called weakly, in a voice that was barely hers. He met her eyes, nodded, waved, and meandered through a crowd of chatty Portuguese tourists toward his girlfriend. She didn’t hug him immediately when he got close enough, and then it felt too weird to do it after that. Alex stuffed her hands in her pockets and mumbled, “Um, did you have a good trip?”

Matt started to answer her, but her jittery mouth cut him off. “Listen,” she rasped. “I gotta own up to something. When you were out of the country, I slept with someone else. And I’m really sorry. And that was really shitty of me. And you deserve better than that. It’s just, you were away for so long, and I got lonely, and I also started to think that maybe we’re just not – ”

“Just not meant to stay together,” Matt finished. “Yeah, I was thinking the same thing.” She looked up at him with those wide, blue eyes of hers. “And I slept with someone else, too,” he admitted sheepishly.

There was a silence before Alex let out a sharp bark of laughter. “Well! We really fucked this up, huh?” she declared with a grin. And then, taking his suitcase from him: “My car’s outside; let’s get you home and we can figure this out on the road.”

They were halfway to the parking lot when Matt threw his arm around her and ruffled her hair. “Missed you, pal,” he said, and it felt like a preview of what they could be to each other, someday, once the dust had settled.

The Quick-Start Guide to Getting Over Someone

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Unrequited love is the woooooorst.

Oh, I certainly get the appeal. I see why it’s played up in movies, music, theatre, and TV. Unrequited love is dramatic, romantic, captivating, titillating. It keeps you on your toes, on the hook, on the edge of your seat.

But what those fictional portrayals don’t quite capture is just how bad it feels to love someone who doesn’t want you. It’s not all giggly-eyed banter in school hallways and pretty-crying in the bathroom mirror. The real pain of the situation is so much worse than that. And I say that as someone who’s spent many a night sobbing in bed until my eyes were so bleary I couldn’t see and my voice was too hoarse to form the words “Why doesn’t he love me?!” anymore.

When you get your heart bruised or broken, lots of people offer you advice. “Laughter is the best medicine,” they’ll say, thrusting a Mel Brooks DVD into your hands. “Time heals all wounds,” they’ll mumble with a shrug as they pass you a bowl of Häagen Dazs. “Everything happens for a reason,” they’ll chide, tossing you a pillow to punch to a pulp. And you’ll beat up that damn pillow, less because it helps your heartbreak and more because all this unsolicited advice is inciting your wrath.

With that in mind, I’m offering you six strategies which, used in tandem and in order, have helped me enormously when oblivious cutiefaces have stomped all over my heart. You don’t have to take this advice. You don’t even have to read this advice. But if you’re tired of living in a whirlpool of tears over someone who doesn’t break a sweat over you – if you’re tired of feeling swathed in lovelorn lethargy and you want to actually get some shit done – then give these tips a try. They’re not revolutionary or new, but they are effective.

Dump out all your feelings. Emotions are like trash. (Okay, not always, but go with me for the sake of this metaphor.) You can try to throw them in the kitchen garbage pail, slide them down the garbage disposal, toss ’em out a window – but unless you firmly, physically remove them from your space, you’ll never be completely sure they’re actually gone from the premises.

So take out the trash. Grab a journal and pen, and write out every single thought or feeling or idea or dream or fantasy you’ve ever had about the object of your affections. Write until your muscles ache – and then switch to typing if you have to. Look for sore spots – any particular concepts or memories that make you feel especially miserable and dejected – and unpack them until they can’t be unpacked any further. Resolve all your thought-loops of anxiety, worry, insecurity, sadness, and anger, so you can finally set them to rest.

You can do this verbally, too, by talking out loud to a friend. But I find journals are more patient and less judgmental.

Forgive them. If you still harbor any bitterness toward your love for not loving you back, you need to nix that shit. The forgiveness process might take time and reflection (boring, but effective), or you might be able to do it quicker with some empathy and the ability to put yourself in their shoes.

For example: when I get frustrated that a crush doesn’t like me back, I always mentally revisit times that someone has liked me and I haven’t wanted to date them. Maybe it was a lack of physical attraction, maybe some doubts about our compatibility, maybe a sexual attraction that just didn’t lean romantic enough, or maybe it was just the headspace I was in at the time. Whatever the case, there was nothing I could have done to conjure feelings for my unrequited admirer; it just wasn’t going to happen. That’s the type of reality check that makes it painful-yet-possible for me to forgive a crush in the present for not loving me back: I know they can’t help it. Because I couldn’t help it either.

View them through the lens of someone who doesn’t love them. You might have trouble viewing your amour with any objectivity, but guess what? Your friends can view that person accurately. You should take advantage of that power.

Ask your friends to tell you about the flaws, faults, and failings of the person you love. They might only have petty things to report – “One of her boobs is bigger than the other!” “He gets crumbs everywhere when he eats!” – but they might also have some bigger complaints to lodge, that they’ve been holding back for fear of offending you in your smittenness. For example, I’ll always be grateful to the friends who pointed out that a longtime crush of mine actually treated me badly, dismissed my ideas, and took my affection for granted. I hadn’t noticed these things at all because I was so wrapped up in my squeaky-clean image of him. Thank god for third-party neutral observers.

If you don’t want to reach out to friends to ask about your love’s flaws, or if none of your friends know the person you’re trying to get over, you can also try to unearth this information yourself. Journal for a nice long time about all the ways your love has slighted you, mistreated you, acted out, fucked up, and fallen short. Normally I don’t advocate focusing on people’s failures, but right now you need to be shaken out of your “I love them, they’re perfect!” mentality.

Publicly decide you’re getting over them. When I say “publicly,” I don’t mean you have to announce it on your blog or blast your Facebook friends with the news – that’s a bit much, even for me. But you should tell at least a couple of close friends that you have decided to get over your crush. To some extent, they can keep you from sending sad drunk texts, creeping your love’s tweets at 2AM, or taking a “casual stroll” through your crush’s neighborhood. You’ll feel more committed to your recovery mission if you’ve told your plan to people you respect.

But this attitudinal shift isn’t just important for your friends to know; it’s important for you to know, too. Once you’ve decided to get over your crush, you’ll (slowly, incrementally) stop mentally highlighting everything they say or do as worthy of your notice. You’ll scroll past their tweets like they were anyone else in your timeline, write about them in your journal only when they’re actually relevant to your day, and wait until you have a moment free to answer their texts instead of hammering out an instant reply. Treat them like a non-crush, and they’ll gradually become one. Mental categorization is more important than we realize, and that includes the mental category of “person I love.”

Destroy all mementos. Fuck, this is really hard to do! I am an appallingly sentimental person, and I cling to physical tokens obsessively if they remind me of a person, place, or time in my life that was important to me. But let’s be real: if you claim to be getting over someone, but you still own objects that remind you of that person every time you see them, you’re half-assing the task at hand.

“But Kate!” you might be screeching as you read this, “Why do I have to get rid of the endtable my crush made for me/T-shirt she gave me/stuffed animal he won me at the carnival?! Those things came from the person I love, but they don’t remind me of them!” Only you can know if that’s really true. If an item is useful to you, or genuinely makes you happy, and its tragic origins don’t come to mind when you glance at it, then it might not be so bad for you to keep it. But you have to get really real with yourself about this, and get rid of anything that makes you even borderline-sad.

If you truly can’t bear to let go of some of these objects – maybe because they’re expensive, one-of-a-kind, or you think you might want them years down the road – then put them in a bag (Gala says you should write “DON’T!” on the outside) and give that bag to someone you trust for safekeeping. It’s okay if your mementos stay in your mom’s garage or your best friend’s bathroom closet; having them out of your space will be good for you.

Go out and live your life!! They say the best revenge is living well. I say the best “revenge” is not feeling like you need revenge. Living well because you want to and deserve to live well – not because it makes you appear a certain way to a certain someone.

Throw yourself into your creative projects. Go to parties and events. Make new friends and new professional connections. Go on dates with other cute people, if you wanna. Learn new skills. Spend time with people who love you. Watch movies that make you howl with laughter. Go for walks in the sunshine. Make lists of goals and then get started. Dance your ass off surrounded by sweaty happy people. Start saving for a vacation. Get your hair done or buy some new clothes. Write a book. Make collage art. Roll down a hill. Write a gratitude list every morning. Listen to music that makes your heart pound with glee. Figure out what would make you happy and then go do that.

We make ourselves miserable when we wait by the phone, endlessly hoping our crush will get off their ass and finally notice us. Relying on other people to make you happy is emotional masochism. Make yourself happy, even if you’ve never really done that before and aren’t sure where to start. Just try a whole bunch of different things and see what sticks. Get out into the world, make things, do things, have experiences. Wash the bitter love from your system with as much hustle and joy as you can muster.

Keep going. Nothing worth doing is instant or easy, but it’s still worth doing.

 

What are your best strategies for when you love someone who doesn’t love you back?

5 Awkward But Effective Ways I’ve Initiated Sex

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Being a sex blogger, contrary to popular belief, isn’t all sensual sweet nothings and longing looks all the time. My approach to sex has never been what I would call “sexy.” I am, instead, a dorky goofball in the sack. And fortunately, that’s worked out pretty well for me.

I don’t know how “normal people” initiate sex. Maybe there’s no such thing as “normal people” when it comes to sexuality. There’s only what’s common, and what’s less common – and I’d wager that awkwardness in bed is far more common than most folks would admit.

Below are five actual things I’ve said in an attempt to get the sexy ball rolling. These are all lines that worked, i.e. happy and enthusiastic sex resulted soon thereafter. I share these not so much as prescriptive suggestions, but as a reminder that you can be silly and strange in bed and still be sexually successful (whatever that means to you). If you’re a weirdo and someone is excited to bang you, that excitement is partially because you’re a weirdo, I promise. Own that, use it, and don’t be ashamed of it!

“I kinda wanna cuddle you. Would that be weird?”

A lot of my sexual initiations begin with “I kinda wanna,” actually. It’s less anxiety-provoking for me than a cocksure proclamation of intent, but it still communicates desire. “Would that be weird?” is really just another way of asking “Would that be okay?” or “How would you feel about that?” – a.k.a. requesting consent.

I said this while lying in bed talking with someone who I found intensely attractive but whose feelings about me I wasn’t sure of. I wanted to do much more than cuddle him (and eventually we did), but I figured this request would be a gentle way to test the waters. He laughed and said, “No, that wouldn’t be weird!” and I breathed a sigh of relief as he pulled me in toward him, because I had a much better sense of where I stood.

“Hey, you should spank me, if you want to.”

“You should…” is definitely bolder than “Do you want to…?” or “I kind of want you to…” but I felt okay being bold in this case, because the person in question had already told me he enjoys spanking people. And we had been flirting a bit, so I ventured to guess he’d be open to spanking me.

Knowing this was a ballsy way to phrase my request, I opted to soften it by adding, “If you want to.” This builds consent into the statement. I probably wouldn’t use this approach with someone shy and accommodating, because I’d want to make sure they actually wanted to do it, rather than just agreeing out of a sense of obligation. But the person in this case was someone I believed would state his objections if he had any. Lucky for me, he was on-board.

“I wanna kiss you, but I’m nervous.”

I said this to someone who made me feel even shyer and awkward-er than I am normally. So much so, in fact, that my eyes were squeezed shut when I said this to him. Admitting my desire felt monumental, embarrassing, huge, even though I knew he wanted to kiss me too.

I often find that owning up to my anxiety – speaking it out loud – helps diffuse some of its power. Built into my confession is an unspoken request for validation. An understanding partner would respond with something like, “Aw, don’t be nervous. C’mere.” I think the person in question did indeed say something like that to me. But I can’t really remember; the excellent kisses have blurred my recollections.

“Would you like some boobs in your face?”

I said this to a friend while cuddling with her and another person in bed, and it ended up leading to my first threesome. She had mentioned that cuddling made her slightly uncomfortable because it’s so intimate, and that adding a sexual element can help mitigate that for her. So I offered up a solution that might make her feel better. All three of us knew we were headed toward threesome-town; this was my gentle way of setting that process into motion.

A lot of folks bristle at the thought of direct consent-asks – “Would you like…?” “May I…?” “Do you want me to…?” It’s true that these can sometimes be a bit clunky or unnatural, but I’ve never found that asking for consent “kills the moment,” no matter how artlessly it’s done. I’d always rather be too sure of my partner’s “yes” than not sure enough. Don’t let anyone shame you out of directness; it’s a good, useful, conscientious approach.

“I really liked going down on you and would love to do it again sometime.”

I sent this via Twitter DM, buried in a paragraph of spluttering explanations and excuses, because I was embarrassed by the intensity of my hunger for dat dick. This initiation probably would’ve been more effective if I’d just said it straight-up, instead of insulating it with clauses like “Sorry if this is crass and un-chill, but…” and “Feel free to ignore this if you think I’m being weird.” I already knew this guy liked having my mouth on his junk, so I didn’t need to be so cagey about what I wanted.

Enthusiasm is such a key part of an effective sexual initiation. In fact, I’d say that the basic recipe is “express enthusiasm + ask for consent.” Initiating sex isn’t just about asking, “Do you want to do this?” – it’s also about establishing, “…because I really, really do.”

 

What are your favorite ways to verbally initiate sex? What are the best initiations other people have said to you?

 

5 Ways to Know You’re Buying From an Ethical Sex Toy Shop

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You always remember your first… The first sex shop you went to, that is.

Mine was well-lit and well-stocked. Friendly sales associates checked in with me just enough to make sure I was doing okay. Products were labeled descriptively and helpfully. I felt neither rushed nor judged as I perused the wares, picked out what I wanted, and paid for it.

I don’t recall many details, because what matters is how that shop made me feel. Sex is so tied up in our emotions – everything from shame to joy – that a sex shop needs to not only be good but feel good, too. You are giving these businesses not only your money, but also your vulnerability and your trust. They have to earn that shit.

Here are five ways that sex shops can prove they’ve earned that shit.

They emphasize body-safe products. Despite the known dangers of phthalates and porous toys, some shops continue to sell products that are demonstrably unhealthy. Jelly vibes, rubber dildos, butt plugs that lack a flared base, lubes chock full of glycerine, “numbing” creams for anal sex – none of these things should be present in the stock of a decent sex shop. High-quality shops carry toys made of body-safe materials like silicone, hard plastic, glass, and stainless steel. Your body deserves only the best, and trustworthy shops know that!

They offer plentiful, accurate information about their products. Brick-and-mortar shops should have salespeople who are knowledgeable about toy materials and how their products can be used (both on- and off-label uses). Online shops should list product materials and/or ingredients on each product page, so you can make informed decisions. You shouldn’t have to ask a barrage of questions or click through a zillion pages to find the information you need: good shops want to equip you to make the best sex toy decisions for you. This should be true whether you’re buying something small, like a bullet vibe, or something pricey, like a fancy realistic dildo.

Their language is sex-positive and inclusive. It’s problematic as hell to say (or even just to imply) that only women have vaginas, only men have penises, all couples are cis straight couples, all bodies are thin and mobile, or every member of “x” group likes “y” sex act. Sex is a sensitive topic, full of nuance and variation, and the employees of any good sex shop will be aware of that. Steer clear of shops whose salespeople, marketing copy, or website makes assumptions about what kind of body you have or what kind of sex you have. Also avoid any shop that plays up themes of “naughtiness” or shame around sex – you deserve to get your toys from stores that ensure they’re accessible, joyful and welcoming for everyone.

Sex toy professionals speak well of them. Some shops send products to reviewers (like me!), and our opinions on those shops will tell you a lot about them. Ethical companies treat their reviewers, suppliers, affiliates and colleagues with respect and kindness. You already know we’re a wealth of information about sex toys themselves, but we also know shit about companies and shops. If you’re looking for a quick opinion, ask a sex toy pro who you trust!

They fix their mistakes. I’ve seen sex shops make countless missteps, from partnering with transphobic corporate sponsors to abruptly changing their rewards program to accidentally invoking sexual assault in their newsletter. The measure of a good shop is how they react to these mistakes. It’s no good to sweep errors under the rug, tell complainants they’re overreacting, or shut down the dialogue entirely: shops should step up and take accountability for what they’ve done, express genuine regret, and explain how they’re going to do better in the future. This is about so much more than sex toys; it’s about creating a shopping environment that feels safe and respectful. That is absolutely vital, especially in the sometimes-fraught world of sex.

What are your red flags and green lights when it comes to sex shops?

Sponsored by EdenFantasys.com

How to Get a Vanilla Person to Spank You Properly

Photo on 2016-06-21 at 3.36 PMI date and bang people who are older than me. Always have. They’ve ranged from one month to eight years my senior, with the average coming in at 28 to my 24. When asked why I skew older, I usually tell people, “I’ve always been mature for my age, so I get along better with older people. Plus, they know what they’re doing in bed!”

I’ve been saying this less lately, though, because actually I’ve given a lot of sexual instruction in the past year. It’s not that my partners are inexperienced or unknowledgeable; most are neither. But several of them were of the vanilla persuasion, so they had little to no experience with one of my biggest kinks: spanking.

Let me be clear. Sometimes it is not worthwhile, or even possible, to get a vanilla person on-board with your kinks. It depends on how “out-there” the kink is, how much commitment it requires, and where your partner’s personal boundaries are. If your partner isn’t interested in fulfilling your kink, or if your enjoyment would rely on a far higher level of enthusiasm from them than they can comfortably conjure or feign, then you may need to have a tough conversation about whether the two of you are sexually compatible.

But assuming your vanilla partner is willing to give your kink a shot, there are ways to help them along. I wrote this about spanking specifically, since that’s the proclivity I’ve schooled people in, but I’m sure these tips apply to various other kinks, too, with a bit of tweaking.

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Broach the topic casually and confidently. If you cringe, blush, wring your hands and apologize as the word “spanking” falls from your lips, you won’t exactly set your partner at ease. Granted, talking about what you want in bed is hard, but the more coolly you can approach the discussion, the calmer your partner is likely to feel about it. Remember: there is nothing immoral or shameful about consenting adults participating in risk-aware kink together, and you don’t need to feel bad about wanting what you want.

Identify and address their fears. Do they think they’ll hurt you? Explain that you want to be hurt. Explain how pain can feel good, euphoric, cathartic. Remind them of the existence of “good pain,” like stretching your muscles or getting a deep-tissue massage. Teach them about safewords and check-ins. Practice and drill these skills together. Tell them “no” when you need to, so they know they can trust your “yes.”

Does it baffle them that you enjoy being spanked? Watch spanking porn or read spanking erotica with them. Tell them what turns you on about it. Explain what Jillian Keenan says about the common iliac artery and its role in spanking-based sexual arousal. Listen to “Why Are People Into… Spanking?” together. Explain the emotional and psychological appeal of being spanked. Tell them your specific fantasies. Tell them about a time spanking got you soaking wet, rock hard, or even made you come.

Do they worry they’ll look silly or be “bad at” spanking? Teach them some concrete skills (see below). Watch porn together where the top/dom turns you on, to give them an idea of what you want. Assign them a character or archetype to play, if they are dramatically inclined. Remind them that you’ll be so deep in the throes of lust and carnal gratitude that you won’t be paying much attention to how they look.

Put safety measures in place. So basic and so important. Make sure they know what a safeword is, what your safeword is, and what they should do if and when you use it. Keep post-spanking treatments on hand, like arnica cream or refrigerated aloe gel. If bondage is part of your play, have your safety scissors, keys, etc. at the ready. Make sure your home is stocked with possible emergency aftercare requirements, like blankets, ice cream, Gatorade, and Pixar movies. Be slightly overprepared, if possible; the knowledge of these protections will help your partner feel more confident and capable.

Prepare them for what might happen. When I get spanked, I tend to go into subspace. I get nonverbal, finding it difficult to form thoughts more complex than “Yes,” “No,” “More” or “Stop.” I might scream or cry from the pain, but that generally doesn’t mean I want to stop. And I might get very, very wet. These are all things I tell a partner when they’re about to spank me for the first time, because these are things that could scare or startle someone if they’re not prepared. Whatever knowledge you have about how your body and mind react to being spanked, you should share that information upfront with your partner so they’ll know what to expect.

Additionally, make sure to explain to them what aftercare is, and what specific aftercare you tend to need after a spanking. If they’re a gold-star vanilla, they might never have encountered the concept of aftercare before, so explain this thoroughly – it’s important!

Give them specific dos and don’ts. A spanking veteran might assume that the instruction “Slap my ass!” is detailed enough. But for a true novice, it isn’t. They might not know where to hit you, how hard they can go, how hard they should start, how much to vary the position and power of their smacks, how to hold their hand, how to wield a spanking implement, what to say to you while they spank you (if anything), when to know it’s time to stop, what else to do to you while they hit you, or whether they’re allowed to leave marks on you. And that’s just for starters.

Lay this stuff out really clearly for them, in advance. “I like to be hit here, here, and sometimes here – but never here.” “It’s best if you start off slow and light, and build up from there.” “Don’t hit the same spot a bunch of times in a row… unless you wanna be really mean.” “You can pull my hair/hold me down/call me ‘dumb slut’ while you do that.” “Stroking the paddle over my skin in between hits feels really nice.” Whatever your particular preferences are, communicate them lucidly and with gusto. The better your partner understands what you want, the likelier they are to give it to you, and the lower their anxiety level will be while they do it.

Teach them to use a 1-to-10 scale. This is an absolutely invaluable tool that I’ve used time and time again, not just for spanking but for other things too. Tell your partner to ask you two questions when they check in with you mid-spanking: “Where was that?” (as in, where would you rate that last hit, pain-wise, on a scale from 1 to 10?) and “Where would you like to be?”

This is fantastic because numbers are really easy and quick to say, even when your brain is addled with pain/pleasure and words are hard. It’s also a useful tool because it gives your partner a concrete way to understand how much pain you are actually asking for. I’ll always remember the time a fuckbuddy asked me how hard he was hitting me, and I said, “I dunno, a 3 or a 4?” His eyes bugged out of his head, and he replied, “I’ve never hit anyone this hard in my life!” With the knowledge that he was currently at a 3 and I wanted to reach an 8, he knew with increased certainty how hard he could actually hit me, and didn’t have to be so scared about overdoing it. This tool rules; use it often!

Give honest but affirming feedback. It’s all too easy to lie about your sexual enjoyment level – especially for folks socialized as women, who were taught to be polite and accommodating even at the expense of honesty. But it’s vital that you tell the truth about kink, not only so your own experience will improve, but so that your partner can trust you.

When you’re learning a new skill and you ask the person teaching you, “How can I improve?” it’s because you actually want to improve. So when you’re lying in bed with your partner after a spanking and they ask you (once you’re able to speak and think again) for feedback, be honest and get specific. A comment like “You could’ve hit me a little more on my upper thighs and less on my buttcrack” might sound like nit-picking, but the more you display your willingness to communicate about details, the more your partner will trust you to tell the truth about big and small aspects of your sex life together. And that means they’re likelier to give you the proper thrashing you’re after!

That said, as with any topic as sensitive as sex, you’ll want to be diplomatic in the way you phrase these suggestions. Tell a kinkster-in-training that they did a bad job, and they’ll never want to try again; tell them they did [a, b, c] right but could improve monumentally by working on [x, y, z], and they’ll be eager to give it another shot.

 

Have you ever taught a kink newbie to enter the life less vanilla with you? How did you do it? How did it go over? Got any tips?