Sex Sells, Part 3: Being a Sugar Baby

This week’s mini blog series on my sex work experiences is coming to an end. For this instalment, I’ve partnered with Rachaels London Escorts to tell you a story I’ve never really opened up about in detail before: that time I was a sugar baby for a little while.

I used to dream of having a sugar daddy who would buy me lingerie and handbags and luxury sex toys. I mean, who hasn’t had some version of this fantasy at one time or another? Though I played around on SeekingArrangement (the best-known “sugar dating” site) and mentally mapped out how I’d spend a generous benefactor’s money, I didn’t think I’d ever actually have a sugar daddy; men with the means and desire for this type of relationship are usually inundated with fit blonde conventional beauties in their early twenties, and I am… none of those things, so it seemed like a long shot.

However, one day in 2017, I got a cordial email from a man whose name I didn’t recognize. He introduced himself, heaped on compliments about my blog and podcast, and asked if I’d be open to a (paid) phone-chat session with him sometime, as the phone “happened to be a favorite play medium” of his. He attached two photos of himself, serious black-and-white formal portraits in which he smouldered at the camera in a suit. I was intrigued.

I was used to charging in 15- or 30-minute increments for such services, so I was surprised when he wanted to book a whole hour. “Please let me know how to render the honorarium and I’ll handle immediately in good faith,” he wrote – music to the ears of someone who so often has to harangue potential clients to finally, reluctantly pay. We agreed on a price and a day and time, and he sent the money promptly, in advance. What a dream.

He opened our first phone call by telling me he planned to approach it as a “first date” of sorts – i.e. he wanted us to chat and get to know each other, hopefully as part of an ongoing connection, not just a one-off phone-sex encounter. That first night, chatting is all we did: he complimented me and my work profusely, told me about his career and interests, and explained his own journey with non-monogamy and kink, which had led him to me. He had a wife, but they both dated and fucked other people with each other’s full knowledge; he, however, preferred to pay dates rather than seek them out organically for free, because he said it simplified the process. He was a highly busy small-business owner and didn’t have the spare time and energy to trawl Tinder or OkCupid, besides which, those sites rarely connected him with the open-minded, kinky, smart women he was seeking. Hence paying me by the hour for a phone date.

We enjoyed our conversation so much that when the hour was up, he asked if I had time to stay for another – with proper compensation, of course. When I said yes, the amount landed in my account almost immediately, and we carried on chatting about our lives. I was amazed that I’d just made the equivalent of 20-30 hours of minimum-wage work for a two-hour phone call that hadn’t even felt like work. He was eloquent and charming and I’d enjoyed our chat. I’d basically been paid to be complimented and flirted with for an evening. Pretty ideal.

I took myself out for a fancy solo dinner the next night, spending some of his money on pasta and cocktails I worked my way through while leisurely reading a book. The decadence made me feel guilty. This wasn’t my life. But maybe it could be.

We continued having these get-to-know-ya phone chats on and off for a few weeks. I learned that he lived in New York, that he had followed me and my work for quite some time, and that some soul-searching on the topic of kink had brought him to the realization that he was a daddy dom. That role spoke to him because he liked guiding the action of scenes and having consensual control over sexual partners, sure, but also because he longed to give guidance, structure, and wisdom outside of the bedroom. I warned him that I wasn’t comfortable calling anyone “daddy” just yet, having recently had my heart broken by my first daddy dom, but I could open myself up to a new dom by another name, perhaps.

We had phone sex for the first time late one night, once he’d established I wanted it, and had (of course) paid for my time. It was long and slow and lovely. I felt guilty taking my time to come as I listened to him spin sentences about giving my clit and labia lots of attention, but he assured me repeatedly that he liked the arousal process, he liked listening to me getting closer and closer to orgasm, and he intended to pay me for any extra time we spent because he wanted to hear me come. He was true to his word.

Sometime after that, he floated an idea he’d been pondering this entire time but hadn’t felt brave enough to bring up yet. He wanted to work out an “arrangement”: he would pay me an agreed-upon monthly allowance so we could talk and text and email organically as our schedules allowed, in lieu of paying by the hour to talk only at certain times. He offered, too, to cover my airfare for all trips I took to and from New York while we were “a thing,” even if I only saw him once during the entire trip. This especially excited me, as my best friend lives there and so did a new person I was flirting with and potentially wanted to date. I’d been wishing I could afford more NYC trips, and now here was a person offering to fly me there once every month or two. How perfect!

The arrangement began; the money flowed in. I bought a Coach handbag and a microwave. I stared at my bank balance sometimes, half-bewildered, half-turned on. I felt better about my financial situation than I have ever felt in my life.

We started planning our first in-person date, slated for mid-December. Pasta, musical theatre, a night in a hotel. I mentioned casually in passing that I’d also be seeing my new beau while there, and I heard my sugar daddy’s voice waver a bit. He told me that, despite having been non-monogamous for years, he still struggled with jealousy occasionally – and this situation triggered it especially, because the other person was “right in [his] own back yard.” I was confused, because he’d known going into this that I had other partners, but I told him I was sure he could work through those feelings and that I could provide some poly-newbie resources if need be.

However, just 10 days before I was scheduled to fly down to see him, he called me and confessed that his jealousy had gotten the better of him. He wanted to “bow out” of our arrangement. He’d thought he could handle me dating another New Yorker, but he couldn’t. I was disappointed – not just because of the money, and not just because it was another rejection in a year that had been full of rejections for me, but also because I had grown genuinely fond of this man. Hearing his supportive voice over the phone had become a comfortingly dependable tradition, and I was sad to lose that. I went over to another partner’s house later that day for a scheduled date and he held me and consoled me and got me high and fucked me well. (Good poly is so good.)

I’m still sad from time to time about the loss of that arrangement. It fulfilled so many of my core desires: to be cared for, and appreciated, and listened to, and pleasured, and spoiled. It topped up my bank account while also topping up my self-worth and my sense of being supported by someone who wanted the best for me.

But there is also joy to be found in making my own money, treating myself to nice things when I can, and developing relationships with people who aren’t threatened by my other potential paramours. I like having people I can depend on, and I also like feeling independent to some extent. This foray into sugar dating taught me more about my ideal balance in between.

 

Thanks to Rachaels London Escorts for sponsoring this post! They’re open from 10AM to 1AM (amazing!) and are available for a range of booking opportunities, such as dates, massages, parties, and naughty nights in hotels.

Sex Sells, Part 2: Camming

I log onto Skype. I send a quick “I’m ready when you are!” message to the stranger who paid me a few minutes ago. They call me up, and I put on my best Flirty Face. Maybe my clothes come off; maybe not. Maybe I have an orgasm; maybe not. By the end of the 15- or 30-minute show, my face is flushed – from nerves or pleasure or both – and I’m marginally richer than I was before.

When I partnered with Bubbles London Escorts to create this blog series on my experiences with sex work, I knew I’d have to touch on camming. And truth be told, I was reluctant. I don’t think of myself as a camgirl, not really; I don’t put in the hours upon hours of self-promotion and primping and flirting with silent time-wasters that people who cam for a living have to do. Folks occasionally ask me for advice on “getting into” camming, and I always bashfully tell them: I don’t use cam sites or seek out customers. They come to me, via DM or email, because they’ve enjoyed something I tweeted or read something I wrote or fixated on a selfie I Instagrammed, and they – inexplicably, to my mind – want to see me get lascivious just for them. I like money, and I like feeling desired, so when the opportunity arises, I often say yes.

I don’t cam very often – usually just a handful of times a year. It’s not something I seek out or advertise all that much, because honestly, it makes me anxious as hell. The process of scheduling a show, attiring myself appealingly, and then performing on camera directly conflicts with my insecurities and awkwardness and shyness. It requires a certain brassy confidence that I can convincingly fake for the duration of a show, maybe, on a good day. It’s for these reasons that I decided late last year to stop taking on new cam clients unless they seemed really great and made me feel really comfortable. The money I got from putting on these shows just wasn’t enough to justify how nervous and drained they made me feel.

But while I was doing it more actively, I had some regular customers I adored. There was the breezily confident guy who would tell me to “just do whatever feels good,” and would sit back in his chair, smoking a cigar and not jerking off at all, while I held a vibe on my clit and writhed. There was the sweet dork who only ever wanted to watch me give head to a realistic dildo, and then would chat with me about social justice in comic book universes once he’d come. There was the woman in her first queer relationship who wanted to learn more about how vulvas work from watching me touch mine. (Secretly, she was my fave.)

Camming wasn’t all smooth ‘n’ sexy; there were hijinks and misadventures, too. A client once requested a show while I was staying in a hotel in Italy with my mom, so I had to stake out a corner of our marble bathroom during a lull in the day and center my laptop between my splayed legs. Another client once reached out to schedule an impromptu show just as I was stumbling home drunk from a night out with friends, so the show he eventually got was probably more raucous than mine typically are. Adorably, someone once bought a camshow from me as a gift for her boyfriend, who she said would’ve been too shy to set one up himself.

My favorite cam clients were always the ones who treated me respectfully and gently, knowing I’m a human, not an object. They’d politely inquire mid-show, “Is it okay if I…?” or “Would you mind showing me…?” and I’d usually be happy to oblige. Sometimes I’d even get a reverent thank-you message from them the next day. “I learned so much from talking with you and watching you,” one such message read. “It opened up something in me.” I cried a little, finding it hard to wrap my mind around the idea that someone found the sight of me jerking off to be not only sexy but revelatory.

I haven’t cammed in quite a while. These days, I’d mostly rather lie in bed in my pajamas, talking to my partner on the phone or reading a book or watching Netflix, not caring what I look like. But I’m still grateful to the clients I had, and those I might have in the future. Though camming makes me incredibly nervous, it also – like many other daunting activities – leaves me flushed and grinning with the knowledge that I “felt the fear and did it anyway.”

 

Thanks to Bubbles London Escorts for sponsoring this post! The owner of this agency is very friendly and makes sure all client requests are dealt with promptly.

Sex Sells, Part 1: Selling Nudes

I’ve always loved good-lookin’ nudes. When I was a young(er) pervy little thing, I would creep to the family computer in the dead of night and surf SuicideGirls, GodsGirls, and archives of old Bettie Page prints – always taking care to clear my browser history afterward, of course. These women, with their lush curves and hard-femme aesthetics, had something I thought I could achieve someday, once I came of age: the confidence to pose nude on the internet.

Especially in light of the recent SESTA/FOSTA laws which are jeopardizing many sex workers’ livelihoods, I was excited when the folks at Dior London Escorts agreed to sponsor a blog series here on my experiences with sex work (the mild forms of it that I have done), so I would have an opportunity to do some destigmatizing through storytelling. I thought immediately of those formative late nights, scrolling through elegant porn. At one point, my desire to join these naked women’s ranks was so great that I shot some provocative (non-nude) photos of myself on my little digital camera and carefully photoshopped the SuicideGirls logo into the corner of one, just to see what it would look like. My mom later found that illicit jpeg on our computer and told me she hoped I was being careful with my images. I still don’t know whether she thought I’d actually somehow been accepted to model for the site despite being underage.

Those early signs of exhibitionism didn’t really bear out in my adult life. I’ve performed in porn from time to time, with friends behind the camera or on camera with me or both, but it was always more for the goofy fun of the experience than for a sexual desire to show off. When I’ve shared lascivious photos online, it’s typically been out of boredom or the need for an ego boost. Even sending nudes to partners doesn’t really get my rocks off in and of itself; I typically don’t do it unless asked to, because it doesn’t often occur to me, and it’s the other person’s desirous reactions that thrill me and make me feel hot.

And yet… I like selling nudes. There is something powerful and sexy about it. Maybe I have a bit of a money kink; maybe it’s just that strangers buying photos of my body makes me feel somehow more “legitimately” hot than when partners enjoy those same photos, because the strangers don’t even know about my charming personality and still want to jerk off to me. Weird but true.

I don’t recall the first time I sold a nude, but I would imagine the interaction originated in a Twitter DM. Maintaining an active Twitter presence full of sex jokes and snazzy selfies, I attract a fair amount of sexually motivated looky-loos. Sometimes random men slide into my DMs with a simple “Hey” and it turns out they want to see me naked; other times they’re upfront about wanting to buy pictures (guess which approach I prefer?!). On the advice of my friend Bex, a gifted salesman, I’ve started answering every vague DM from a stranger with a concise “What can I help you with?” This sets a businessy tone for our conversation and helps me quickly filter out flirty time-wasters so only actual customers remain.

I always ask interested buyers if there’s anything in particular they want to see. If it’s something fairly basic (say, tits or ass – the classics), typically I already have some great shots on tap that I can send along. If they want something more niche or involved, I set aside some time to shoot what they’re looking for. I don’t even necessarily have to be at home to pull this off; I have fond memories of snapping impromptu nudes for clients in bar bathrooms and a boyfriend’s bed (the boyfriend knew what was up!). I feel like a badass every time I make quick cash just taking pictures of my body, a body that feels utterly ordinary to me because I walk around in it all day every day. What a revelation and a joy that some people like this chubby, flawed body enough to pay for digital glimpses of it, even without knowing anything about me.

The only times selling my nudes has gotten awkward were when the buyer was someone I knew. Either I felt guilty about charging them money (even though they were proactively trying to pay me) or the interaction added a sexual element to a relationship that previously lacked that dimension. But in every case, these people have been cordial and respectful throughout the process. I’ve even said “no” to a few of them and gotten nothing but sweet understanding in return.

I’m always happy to sell nudes, so slide into my Twitter DMs or send me an email if you want to buy some. I love that this exchange is a total win-win: my buyer walks away happy (and hopefully jerkin’ it), and in return I get a fistful of cash and the knowledge that someone, somewhere, thinks my body is beautiful.

 

Thanks to Dior London Escorts for sponsoring this post! They’re one of the most popular escort agencies in London, known for their high-quality service and employing a wide range of women.

Review: Blush Novelties Avant Pride P1

There have been many debates on my social media timelines recently about objects’ aesthetics versus their usefulness. Some people say, for example, that there’s no reason to keep books once you’ve read them, because you’ve already absorbed the information therein, while others insist books are personal objects worth keeping and curating into visually pleasing collections. Some people tuck their lingerie, neatly folded, into drawers, while others proudly drape their silks and satins everywhere. Some people have a practical lamp hanging from their bedroom ceiling, while others – like me – have a fucking disco ball.

When it comes to sex toys, however, for the most part I am more interested in function than appearance. My favorite vibrators are the Magic Wand and Eroscillator, both widely considered some of the ugliest in the biz. My favorite dildos are made of glass, not because they’re gorgeous (though they are) but because they press firmly against my internal spots. I chose the simple black Liberator Throe, because I want it to keep squirt and blood off my sheets, not jazz up my decor. Y’know?

But when Tabu Toys offered me a product of my choice from their “lesbian sex toys” section (which, by the way, other types of people can use these toys, and lesbians can use other types of toys, and not all lesbians are cis women!), my eyes fixed immediately on the Blush Avant Pride P1 dildo. I had no idea if it would work for me, or for my partners. I just knew it looked gay as heck and I wanted it.

Pegging is still a relatively new thing for me, and wearing a cock still feels a little odd. It helps to use dicks that are glitzy and bright, dicks that make me feel aggressively girly, dicks that pointedly are not flesh-and-blood dicks. So I figured I would like strapping on the P1 and pushing it into my partner.

Before I go any further, I gotta say: this dildo is smaller than I was expecting. At only 6 inches total in length, it’s not ideal if you or your receiving partner are fans of deep penetration. Once you factor in the base and the harness, there’s really only about 5 inches of insertable length. That’s fine for hitting most G-spots and prostates, but it doesn’t give you a whole lotta leeway.

It has a big bump near the base that tops out at 1.4″ wide, but I feel it’s a bit oddly positioned: it doesn’t even go in unless I push almost uncomfortably deep, whether I’m pegging a partner or just fucking myself with this toy. The head is smaller, and it does press against good spots, but there’s no “wow” factor. It’s like someone is warming up my G-spot with one gentle finger, rather than pounding against it with two or three strong ones. My partner agreed: he said it didn’t leave him panting from prostate stimulation the way something made of steel or firmer silicone can, but it was enjoyable nonetheless.

The neck of the toy, too, leaves something to be desired. It’s nicely shaped – I like the way it gently tapers from the head, making my vag want to pull the toy deeper – but it’s just too floppy to make this dildo a decent G-spotter or prostate toy. Those spots tend to need firm touch, and the P1 bends under pressure.

All of that said – the aesthetics of this toy still appeal to me. I feel cute wearing it; I like seeing it on my nightstand; I dream of wearing it strapped into my red leather thigh harness to some kind of X-rated Pride event someday. It looks adorable sliding in and out of someone’s mouth, like a vibrant little lollipop. My partner likes how the colored stripes give you a way to measure how much of the toy you take on each try, so you can challenge yourself to take more: “I got up to blue this time!”

I admire that Blush offers high-quality silicone dildos at reasonable prices – this one is $45 – and that much of their marketing is relatively gender-neutral. This is a dildo I might recommend for someone who was new to prostate stimulation and/or pegging and wanted something comfortable and unintimidating; it’s just not going to be a go-to for people like me and my partner, who’ve already stuck a bunch of stuff in our holes and have grander visions for them now.

There should be more rainbow dicks in the world, is what I’m saying.

 

Thanks to Tabu Toys for sending me the Blush Novelties Avant Pride P1 to try! This review was sponsored, and as always, all writing and opinions are my own.

Roleplay and Rapport at the Library Bar

Maybe I shouldn’t have arrived so early. Why do I always do this? I glance over my shoulder at the door again. Maybe he’ll show up in five minutes. Maybe he’ll show up now.

I always get nervous before interviews, even though I’ve been doing the whole professional-sex-journalist thing for going-on-7 years now. It’s just stagefright, harmless jitters, but it happens like clockwork. It’s why I rolled up to the Library Bar 10 minutes early. It’s why I keep sneaking peeks at the door.

Is that him? He’s wearing a dark button-down shirt. He’s looking my way. He’s smiling and waving. (He is my partner.) He’s coming over to sit next to me. (He is my partner.) He’s shaking my hand and saying, “Hi, I’m mb.” (I know who he is. He is my partner.)


Let me back up for a second. Months ago, when discussing potential roleplay scenarios, my boyfriend and I struck upon the idea of a journalist/source roleplay. I am a journalist, after all, and he is a semi-frequent media interviewee, being a tech fancyboy in New York, so we’re already comfortable in these roles.

Initially we envisioned it as a scene of strategic outsmarting, psychological manipulation, me trying to get info out of him for an investigative exposé and him trying to keep me at arm’s length. But the more we thought about it and discussed it, the more we wanted it to be a different type of scene entirely. We still wanted to play ourselves – me, a reporter; him, a tech CEO – but our focus shifted more toward the flirtation and chemistry that could naturally develop during an interview.

Storytelling dynamo Claire AH has talked often about how roleplay – which she calls “sexy improv” – can be an opportunity to explore ways you and your partner didn’t meet, but could’ve. She sometimes envisions, for example, having met her musician husband by being a groupie of his band, rather than on OkCupid. I love this idea, and how it allows you to re-access a state of charged unfamiliarity with your partner, flirting in double entendres and meaningful glances in ways you can’t do as readily when you’ve been dating for months or years.

Having defined our goals for the scene, BF and I started emailing back and forth, the way we would if we were actually setting up an interview with a stranger. My character needed to speak to an app developer for a story – and his character, it so happened, would be in Toronto for a “conference” soon. We settled on a day, time, and location. I started prepping my questions. It all began feeling very real.


Back to the Library Bar. “Hi, I’m mb,” this ridiculously handsome man says, grabbing my hand in a firm, CEO-appropriate handshake. “I’m Kate,” I reply. “Nice to finally meet you!”

He sits down next to me at the bar. (Was the bar the right spot to choose? Is it more professional to sit opposite a source, at a table?) He asks me what I’m drinking. (A Bulleit bourbon on the rocks. One of my fave orders when I’m trying to impress a dude who probably knows more than me about such things.) He orders an old fashioned. We small-talk about how he’s enjoying Toronto, what he’s been up to, what he thinks of his hotel.

Then he asks me what my piece is about, and I brighten. “So… It’s for Playboy. Ever heard of it?”

He laughs. “I only read it for the articles.”

“Well, great, ’cause I’m writing one of those articles! It’s about how I think nerds are better in bed.” I watch his eyes widen. We didn’t discuss this in our pre-interview emails. Sometimes I prefer to take sources by surprise. “I spoke to a web dev; I spoke to a game dev; I needed to speak to an app dev. So, thanks for agreeing to talk to me!” He is immediately on board, engaged and listening hard. I flip open my notebook to my list of questions. I begin.

“Do you think nerds are, on average, better in bed?” “Which subsets of the tech community do you think would be especially sexually skilled?” “What sexual acts do you think programmers would tend to be good at?”

His answers are measured, thoughtful, yet enthusiastic and off-the-cuff. He posits theories, tells stories from his own life, and cites thinkers he admires, like Michael Lopp and Evie Lupine. His blue eyes flash with intelligence and wit. Occasionally, when I ask him something, he gives me this pure-of-heart little smirk and says, “Good question!” I wonder if he can see how much it melts me when he compliments my competence, even though I’m a grown-ass journalist who knows her shit and knows her worth.

The thing about being a sex writer is, there will be opportunities for interviews to get flirty. In 99% of cases, I neither want this outcome nor think it’s smart to pursue it; it’s unprofessional, usually unwanted (by one or both parties), skews the story, and can get messy.

But this app mogul on the barstool next to me is… very cute. And he has been essentially selling himself to me as a promising hookup for the past hour. And he keeps reaching out to gently shove my shoulder to make a point, or holding my gaze a little too long while describing skilful fingerbanging. At one point he loses his train of thought mid-sentence and says, “Sorry, that dress is just… really good.” It’s a new one, vintage Betsey Johnson. “It’s kind of a ‘professional reporter lady’ dress,” I say, blushing, and he shoots back, “More like a ‘turning on a source’ dress. Wow.” I laugh and hide my warm face behind one shy hand.

I’ve asked all my questions, taken all my notes, and closed my notebook. “Want to get another drink, now that you’re off the clock?” he offers, so easily, and we order two more cocktails from the busy bartender. Flipping the script, this articulate interviewee asks me about my work – what I like about it, what I don’t – and I mention, in passing, that it can get complicated when a source wants to fuck me and I’m not into it. Or when I want to fuck a source, but my editor isn’t into it. “So is this the type of assignment where you might sleep with a source, or no?” he asks innocently, and I practically choke on my drink.

As the alcohol plies us further, we get to talking about FetLife: neither of us use it much, and he knows some nerds who are trying to build a better alternative. “What’s on your fetishes list?” he wonders, and I wrack my brain for the answer least likely to freak out this near-stranger. “Uhh, spanking?” I try, and he bites his lip like a sadistic Cheshire cat. “I actually have some impact implements up in my hotel room,” he mentions, so casually, and that room is now the only place I want to be.

He offers me a sip of his martini. “Ooh, that’s a daddy drink,” I say when I try it. “What does that mean?!” he asks with a quizzical smile. “Oh, you know, like something a daddy would drink.” I hide behind my glass when he intuits effortlessly, “Oh, so you’re into DD/lg, then.”

He’s getting closer and closer to me, as we’re getting tipsier and flirtier and farther off the path of our initial conversation. He’s got his arm draped over the back of my chair, and is gazing into my eyes like nobody else in this crowded bar exists. I lose my words, lose my breath. “Kiss me,” he says, out of nowhere, and I do, because I need to.

At some point we decide that yes, I will go up to his room with him – and I will disclose this key information to my editor when I file the story. We settle up and amble to the elevator. Inside, he pushes me against a wall and kisses me, like he’s wanted to do that ever since he first saw me from across the bar.


If you’re interested in trying a roleplay like this – in person, out in public, pretending not to know each other – here are some tips I took away from our first attempt that I think might be useful to you too:

• Define your intentions. As with any kink endeavor, it’s good to make sure you and your partner are hoping to get something similar out of the scene, or at least that your hopes for the scene are compatible. My partner and I are both into flirting, and knowing that that was the primary intention of our roleplay allowed us to focus on that aspect fully and enjoy it even more.

• Set the stage. Whatever the scenario you choose for your roleplay – meeting someone new at a bar; striking up a convo with the stranger beside you at the theatre; going on a first Tinder date – prepare for that situation however you normally would. It’ll help get you into the appropriate headspace. For this roleplay, for example, my partner and I exchanged businessy emails weeks beforehand, and I prepped and researched just as I would for an actual interview.

• Dress the part. Clothes and other self-presentation details can help you get into character, even if your “character” is just an alternate-universe version of yourself. This can be especially helpful if you and your partner hang out earlier in the day and then go do a roleplay; my partner changed his shirt before our interview, for example, and it was a small thing that nonetheless made him feel like a slightly different person to me. You can also change stuff like your perfume, jewelry, and hairstyle, to set your character apart from your regular self.

• Do something, dammit. Decide on a concrete task or interaction that the roleplay will center around; don’t just show up at the location and stand around awkwardly. Our roleplay hinged on an interview, and I did an actual interview, because I knew it would make me less nervous and would lend some purpose and direction to the scene. Even if your roleplay is pretty straightforward, like a chance meeting with a cute stranger at a bar, have some idea of what you want to do: bring a book to read, or have a specific drink you want to try, or a specific occasion your character is celebrating, or something.

• Commit to the scene. The #1 question I got from my Twitter followers about this roleplay was essentially, “How do you stay in character?” and the answer is… just decide to stay in character. As with dirty talk – not to mention improv, which roleplay essentially is! – you will actually seem (and feel) sillier if you half-ass it. Hopefully your partner is someone you trust not to laugh at you for wholeheartedly throwing yourself into the scene – because if that’s all they want to do, why do the roleplay at all?!

• Making mistakes is okay. A few times during our roleplay, my partner and I accidentally referenced some of our real-life inside jokes, or responded to things how we ourselves – but not our “characters” – would respond. Slip-ups are bound to happen, especially if you’re not accustomed to this type of improvisation. That’s fine. There is nothing wrong with laughing for a moment at the mistake you’ve made and then moving on with the scene. The entire narrative doesn’t have to fall apart just because you screwed up for a second.

• Debrief and discuss afterward. You should do this when you try any new kink activity. Talk about what went wrong, what went right, what you want more of in the future, and what you want less of. Talk about what was hot, what felt weird, what surprised you. My partner and I have already figured out some other roleplay scenarios we want to try in public, having learned more about our desires and fantasies from this first one. This experience has opened up a whole new avenue of play for us, and we can only continue further down this path because we’ve thoroughly compared notes about this first scene.

Have you ever done a roleplay like this before? Would you like to?