Author: Kate Sloan

The Anatomy of a Good Tinder Message

Kate Sloan

Ah, Tinder. Shallowest of shallow dating apps. Devourer of time, energy and brain cells. Cesspool of tiger-obsessed weirdos, hostile Felipes, and “Netflix and chill” jokes. So terrible, and yet so enslaving.

I’m currently in the throes of a full-blown Tinder fixation, which happens to me from time to time. The gameified rush of swiping left and swiping right turns me into a rabid date-seeker, desperately flipping through my available matches for anyone who seems not-awful. And even when the motivation to find partners is removed, I still find Tinder fascinating on a sociological level. Look how far we’ve come, us clever humans, that we can find companionship and sex just by flicking our fingers and staring at colorful images on a tiny screen.

But although I’m enthralled with Tinder, I still kind of hate it. And the thing I loathe most about it is that the people on it are boring. Or, rather, they’re generally not good at demonstrating how interesting they (probably) are.

Sending an initial Tinder message isn’t like walking up to a stranger at a bar. If we met in real life, the content of your greeting would be less important than its delivery, your attractiveness, and my mood. A simple “Hey, how are you?” at a bar could turn into a rollicking conversation if I found you cute, I was in a talkative state of mind, and we had good conversational chemistry after that opening line.

On Tinder, however, “Hey, how are you?” is boring. I get several messages like that every week. And though I could glance at your profile again when you message me, I might not. The content of your message is all I have to go on. So if it’s bad, I’m probably not gonna talk to you. Like, at all. Not even in weak pleasantries, the likes of which you might get if you “Hey, what’s up?”-ed me while I was grumpy-drunk at a bar.

Before I go any further, a caveat. This post might make it sound like I never initiate conversations on Tinder, or that I expect men to be the initiator in all cases. Neither of those things are true; however, that is how it’s gone down in most of my Tinder chats. Blame it on patriarchal gender roles or the Dickonomics of Tinder; men tend to drive the action on this app, and on most online dating services.

Since that is the case, I, as an active female user of Tinder, am by default an expert on what kinds of messages I do and don’t like to receive. Months of boring conversations and uninvigorated openers have sharpened my sense of this. Here are the three things I think you crucially must do when you send an initial Tinder message to someone you think is cute:

  1. Compliment them. Choose something specific about them that you genuinely like, and tell them that you like it. Assuming you’re looking for something more than a hook-up, it’d be smart to compliment something non-physical, like a personality trait that comes across in their bio or a hobby shown in one of their photos. If you can’t think of anything to compliment them on, well, why did you swipe right on them, then? Surely there was something about their pictures or description that appealed to you.
  2. Prove you’ve read their profile. Reference something from their bio or photos. If your message is so generic that you could copy-and-paste it to many different matches, you’re not trying hard enough.
  3. Ask a question or two. If you don’t, they’ll have nothing to respond to! Try to avoid boring, commonplace questions like “How’s your week going?” or “What are you up to tonight?” You can ask those later, once you’ve got the conversational ball rolling. To start, ask them a question they’ll be excited to answer – maybe something about one of their passions or interests.

Those are the three basic building blocks of a solid Tinder initiation. Bonus points if your message is also funny, properly spell-checked, and hints at an activity or interest that might make for a good first date if the conversation goes well.

To illustrate how and why a first message’s construction is important, I’ve pulled a few examples from my own Tinder inbox. They’re not pretty, but hopefully you’ll learn something from them.

imageThis dude had clearly read my profile, but maybe only the first sentence of it. I understand that it’s exciting to encounter a sex blogger if you’ve never met one before, but when guys take this tactic with me, it makes me feel objectified and reduced to this one small detail about who I am. And while he did ask a question, it’s a bad question: it only warrants a quick yes or no, and the answer is already in my profile. When you ask someone a question with the intent of starting a conversation, it should require more than a few words in response, and it should be a question you don’t already know the answer to. Finally, he complimented me, but it’s a generic compliment without much substance. I already know he finds me attractive, because he swiped right on me; now I want to know what else he finds interesting about me. And if the answer is “nothing,” then we’re probably not a good fit.

imageSome guys try to initiate convos in gimmicky ways like this, and it just doesn’t work. It makes me feel like you’re a con man and I’m the mark. It’s also an insult to my intelligence: this dude and I both know he isn’t really messaging me to get my help remembering the name of a movie he once saw, so why pretend that’s what’s going on? Online dating can feel so contrived anyway; it’s best to be genuine. Tell me about yourself and ask me about myself, instead of constructing this strange excuse to talk to me.

imageThis is an example of the kind of message that would go over better if it was spoken out loud at a bar or a party, but doesn’t work well in a medium like Tinder. More than half the messages I get are some variant of “Hi,” “Hello,” “What’s up?” and so on. These messages are boring, require the bare minimum of effort to send, and show zero indication of why the person finds me interesting. I’m only motivated to answer this kind of message if the person’s profile is very intriguing to me, which is rare.

imageI get the sense that this guy was probably just looking for a hook-up. If that was his goal, then his approach was a good one: he complimented me on my physical attractiveness, and later asked me straight-up if I wanted to “have some fun” (i.e. hook up). I didn’t answer because I was looking for something more relationshippy. Keep in mind that your messages can and should establish some sense of what you’re hoping to get out of the interaction. I find physical compliments unsatisfying on Tinder because, duh, I already know you’re attracted to my photos; now I want to know why you might be attracted to my brain. But if sex is all you’re after, a physically-based compliment could be a good way to subtly communicate that.

imageThis message is a question, and an interesting one, so it’s got that going for it. But I didn’t reply because the message contained no indication of why I should find this guy interesting. I’m not on Tinder to educate people or to have philosophical discussions; I’m on there to meet people for dates and/or a relationship. So, while it’s great that this guy wants to learn about the poly lifestyle, I’m gonna need a little more than “I don’t understand this thing; please explain it to me!” to get me interested in talking to someone.

imageThis message could have been copied-and-pasted to literally anyone, if he replaced my name with someone else’s. It’s fantastic to get a message from someone who shares my interests, but if that’s the case, I’d love to know what those interests are! All I could really reply to this is something like, “Oh yeah? Like what?” and that’s not the kind of message I’d be bursting to send. Be interesting and specific. Craft your message so I’m excited to answer it.

imageThis is a cool opener. It’s simple, but I like it. Asking someone about their passion is an easy, accessible way to capture their attention and get them talking. This guy could’ve improved his message, however, by relating the question back to himself so I’d be interested in answering him rather than just answering the question. For example, he could’ve mentioned a favorite journalist of his and asked if I’d heard of them, or he could’ve told me what led him down the road to his passion. Providing more information for the person to respond to is always better than not providing enough!

imageThis is the first message I received from the guy who is now my boyfriend (!!). It caught my attention because it’s straightforward and instantly proved he’d read my profile: he’s referencing my bio where I mention that I like old movies, celebrity impressions and Scrabble. He’s given me some information I can respond to (“Why The Wizard of Oz?” “What are your favorite board games?”) and pointed out some commonalities between us that might make me want to talk to him. He potentially could’ve improved this opener by complimenting me, but pointing out shared interests is a type of compliment – it means, “Hey, that thing that you like? I like it too, because it’s a good thing!”

What are the best first Tinder messages you’ve ever received (or sent)? Do you find that some approaches lead to actual conversations more often than others? I want to hear about your Tinder experiences in the comments section!

Review: Shibari Mini Halo Wand

Kate Sloan

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I wanted to like the Shibari Mini Halo Wand. And there is so much that I do like about it. But it has a fatal flaw that I just can’t get past, no matter how much I try to convince myself it doesn’t matter.

So let’s get the Mini Halo’s hamartia out of the way right off the top. When you turn it on, it starts at the strongest vibration speed. If you want to get to the lowest speed instead, you have to hit the “change speed” button eight times.

Please take a moment to visualize yourself trying to press a vibrator’s button exactly eight times in the middle of a masturbation session – no more, no less. And then imagine yourself needing to do that multiple times during any given session. And then imagine yourself throwing the vibrator across the room in a fit of rage. Congratulations, you have just experienced a fraction of the aggravation I endured while trying to test the Shibari Mini Halo Wand.

See, when I use vibrators, I always begin at the lowest speed. My clit is sensitive so I need to start gentle and ramp up from there. If I start at a moderate or high power level, not only will it feel painful and uncomfortable, but it’ll also get me real numb real fast. And that significantly lowers my likelihood of reaching orgasm. So the lowest speed is the way to go, at least at first.

If you read that last paragraph and thought, “That’s not just you, GJ – that’s how most people use vibrators,” well, yes, I think you’re probably right. Which is why it’s so annoying that Shibari chose to design their wand this way. I could understand having the wand remember the speed you used last time and starting there, like the Doxy Wand does; I could even understand having the wand start at the top speed if there was also a “go to the lowest speed” button, to make that process instantaneous. But there isn’t. You gotta hit that middle button eight fucking times to get it to speed number one.

If it seems like I’m harping on this a lot, that’s because I am. And also because it irritates the fuck out of me. This wand could have been so great if not for this one issue.

The Mini Halo is a wonderful size for a wand vibrator. It fits in my hand comfortably, and is large enough to feel impactful but small enough to fit into a purse. The head is shaped such that you can get broad or narrower stimulation depending on how you angle it. The vibe feels solidly constructed, but retails for just $59, less than lots of “fancier” wands on the market.

The vibrations are excellent. They are deep, rumbly and penetrating. The intervals between each of the eight speeds are small, so the cranking-up process feels smooth and gradual rather than jumpy or jarring. The toy is rechargeable and holds its charge for a long time – I’ve had mine for over three months and have only needed to charge it once in that period. Although, admittedly, I probably only used it 7 or 8 times before deciding the deep, strong orgasms it delivers aren’t worth the hassle of dealing with its tragic flaw.

If you want a rechargeable wand vibe, get the Magic Wand, Iconic Wand or PalmPower. If you just want a strong, rumbly, awesome vibrator, get the We-Vibe Tango, Lelo Siri 2 or (again) Magic Wand. If you think you can forgive the Shibari Mini Halo for its major defect, then go for it, because it’s otherwise a top-notch toy – but as for me, I am far too lazy and uncoordinated to press a button exactly eight times after each and every instance of turning my vibrator on.

 

Thanks to Peepshow Toys for sending me this vibe to review!

My Clit is a Diva and I’m Sorry-Not-Sorry

Kate Sloan

“Higher.”

He moves his fingers a centimeter higher on my clit, and keeps rubbing.

“No, higher,” I say again.

He looks at me quizzically. I grab his hand and move it where I want it. Ah, yes. That’s better.

A couple minutes later, his hand slides down to my opening and he pushes two thick fingers inside me, finding my G-spot and then my A-spot with ease. And that’s nice. Fuck, he’s good at that.

When he comes back up to my clit, though, he forgets everything he’s learned. Goes straight for the exposed bud in the middle of my folds. I wince.

“Higher.”

Without even looking at his face, I can feel his confusion in the slow way he drags his fingers upward an inch or two. Maybe this is the time when he’ll remember, when he’ll get it. I love that moment.

Later, after drinks and dinner and sly sex chats in a noisy pub, we walk back to his place together. Boots crunching in the snow, arms bumping against each other casually as we walk. “I think I’m starting to figure you out,” he says. “It seems like you like the shaft of your clit to be stimulated, not the clit itself.”

I brighten. “Yeah! Exactly.” And I want to hold his hand, but both of our hands are stuffed in our coat pockets to hide from the cold.

“In my experience, you’re definitely an outlier,” he tells me, “but it’s nothing I can’t work with.”

Later that night, he gets it just right, and I don’t even have to move his hand.

This is a process I’m used to. Because my clit, like me, is a finicky princess. It likes to be stimulated downward through the clitoral hood, or sideways through the inner lips. When I use vibrators, I usually hold them over my clit hood, or on one of my outer labia. My pussy can handle a lot, but one thing it cannot handle – one thing it actually hates – is direct clitoral stimulation.

I was inspired to write about this after reading JoEllen’s post about the Womanizer, a clitoral stimulator I tried and admittedly liked. In her review, she writes about her hatred for direct clitoral stimulation, and her distaste for the common sexual discourse which says, “Touch a woman’s clit and she’ll definitely come!” It got me thinking about how sexual outliers are often shamed, even within the sex-positive communities which claim to unjudgmentally accept all preferences and tastes.

As a sex toy reviewer and a routine user of vibrators, I’m often accused of having “desensitized” myself. When I explain to laypeople or even “sexperts” that I have trouble coming from the touch of a partner’s tongue, fingers, or dick, sometimes I’m told I should lay off the vibes for a bit and see if my sensitivity returns.

Granted, I am more sensitive when I take a vibrator sabbatical. And I make a habit of avoiding vibration and orgasms for 2-3 days before a scheduled encounter, so I’ll feel everything my partner does to me and reach orgasm more easily. But it’s not vibrators that made me this way. I think my body’s just naturally a tougher nut to crack.

You know how I know that? It’s because my orgasm difficulties aren’t related to a lack of sensitivity, they’re often caused by an excess of sensitivity. When a partner’s tongue grazes my exposed clit, it hurts and I get wrenched out of the moment. When a vibrator slides too low on my clit hood and makes direct contact with that bundle of nerves, I feel overloaded and have to crank down the power. When someone’s fingering me and goes straight for my clit, instead of spending time turning me on by touching the rest of my vulva first, I get overstimulated and that makes me feel numb. It’s like my clit panics and hides under a blanket, if by “hides under a blanket” I mean “gets desensitized by the onslaught of sensation.”

It’s been nearly two years since I’ve had an orgasm from oral sex. This is big news, considering how obsessed with cunnilingus I used to be. But, yes: the last person to get me off orally was my ex, with whom I ended things in late 2014. I’ve slept with several more people since then but none of them have made me come with their mouth.

I think that’s partly owing to how my body has changed: I tend to need more intense stimulation now than I used to, for a longer period of time, to reach orgasm – and tongues get tired sometimes. I also rarely come without some form of penetration these days, which – let’s be real – is a difficult thing to incorporate into cunnilingus and often isn’t done very well when people try, at least in my experience.

But the other reason, and maybe the main reason, I haven’t come from oral in ages is that I haven’t had a partner stick around long enough to learn how I like it. Most of my sexual flings in the past two years have been short-term or one-offs, always with people who had other partners at the time and therefore couldn’t be expected to keep my Very Specific preferences programmed into their muscle memory. My ex had time to learn my rhythms, signals, noises, and most importantly, how to lick my clit without causing me actual pain.

My clit needs to be romanced, seduced, won over. It needs you to play hard-to-get, while knowing the whole time that you’ll eventually give it what it wants. I want you to ignore my clit for a long, long time, while you kiss my mouth and neck, suck and lick my nipples, smack my ass and thighs, bite my mons and fleshy hips. I want you to shower my labia and vaginal opening with attention, because most people don’t. I want to be at the point of begging you and punching the bed and moaning in despair for at least five whole minutes before you even hint at going near my clit.

The reason for this rigamarole, you see, is that it amps up my sensitivity while also increasing what I can handle. If I’m halfway to coming by the time you make clit contact, I will almost certainly come at some point. What guarantees me not coming is if you jump straight to my clit and short-circuit the whole system. Be careful. Approach with caution. Don’t cannonball into the pool; just trail a few fingers in the shallow end and see what happens.

My ex understood this. He also understood how to use his lips and tongue around the periphery of my clit instead of stroking it directly. He knew when to wander away from my clit for a while, to lick my opening or nibble my labia, so the main attraction could take a breather and gain back that original fervor to be touched. And when the time came to buckle down and do identical tongue-circles for a couple minutes to actually get me off, he knew how to do that too.

Once, he asked me, “Is there ever a situation in which you want me to lick your clit directly?” My first instinct was to shout “NO! NEVER!” but when I thought about it some more, I reconsidered. “You can try it, as long as you’re very gentle,” I told him. After that, he would occasionally – as sparse punctuation in a widely varied cunnilingus session – pull my clit hood back and press the lightest, softest, slowest of licks to my exposed clit. It felt almost like an act of kink: I was giving him the power to do something potentially painful, and he was doing it without hurting me. I trusted him, handed over a particular power I rarely trust partners with, and he used that power for good. It was kind of magical.

Going down on someone with a picky clit is a complicated business, man. It requires showmanship paired with tenacity. Decorum married to determination. A sense of flair, and some elbow grease. But yeesh, those orgasms were worth it.

In fact, since my ex, I haven’t had any orgasms with partners that didn’t involve me assisting in some way: holding a vibe to my clit, or rubbing it with my fingers. Because, as I said, none of them were in my life long enough to learn what I like, remember it, and get good at it.

But I live in hope that I will have another partner who’ll put in the time, effort, and brainpower to figure me out. Who’ll get to know my clit’s weird ways, the same way he gets to know mine. Who’ll learn me like a video game, patiently, and never get annoyed that there’s no cheat codes.

Because, dammit, my clit’s an outlier, but it still deserves pleasure.

Monthly Faves: Show-Offs, Blowjobs, Butt Stuff & Balconies

Kate Sloan

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February was a super tough month for me emotionally, but in between cry-a-thons and anxiety attacks, I also managed to have plenty of good sex. Here’s a breakdown of the highlights…

 

Sex toys

• I have said this to you before… like, many, many times… but I really enjoyed the Eleven this month. It helps that I used it in a porn shoot (more on that in a second), but holy shit, it’s just a classic as far as I’m concerned. Sometimes I’m struggling to reach orgasm and I break out the Eleven as a last resort, and it always, always does the trick, somehow.

• To flagrantly repeat another toy that’s gotten its fair share of mentions in my monthly faves: the Magic Wand Rechargeable really earned its keep this month. I used it in the aforementioned porn shoot, as well as during my first anal sex experience and many solo sexytimes. It’s nice to have a vibe that works so reliably well that I don’t even have to think about it.

• When Bex visited early in the month, we took a trip to Come As You Are and I became fixated on the limited-edition pink version of Aslan Leather’s Jaguar harness. It’s $130, I already owned a Jaguar harness in black, I’m trying to save money for an upcoming trip, and I don’t even have an opportunity on my horizon to use a harness – but nonetheless, I wanted one, because it’s femmey and perfect. So I posted in a local kinky trading group to ask if anyone wanted to buy me a pink Jag in exchange for my black one plus some other toys I’d throw in, and a lovely lady took me up on my offer. I’m soooo happy I own it. It looks gorgeous on me and I’m going to make someone’s fucked-by-a-femme fantasy come true someday.

 

Fantasy fodder

• If you follow me on Twitter, you may have noticed it’s been a bit of a blowjobby month for me. My ideal blowjob recipient was in town so I had some mouth cravings to contend with. One of my favorite encounters in February was an impromptu blowjob date, which resulted when I messaged dude to offer him BJ carte blanche. I got to suck off one of my fave dicks in the known universe in a dimly lit room while we listened to R&B slowjams. Twice: once before dinner/drinks and once after. It was pretty much the best. And I continued to think about it a lot through the month, because unf, yes, all the good dicks in my mouth, please.

• My friends, you have not lived until a hot androgyne has rammed the shit out of you with an Eleven at a sex club in front of an audience as part of a live porn shoot. I thought I’d be too nervous to have a real orgasm, and was entirely prepared to fake one (which I know is bad, but it was a performance!) – but then my babely scene partner leaned close to my ear and whispered, “Does it turn you on that all these people are watching you?” That, combined with the well-wielded Eleven and the Hitachi I was pressing to my clit, triggered a very-real orgasm almost instantly. Welp. I didn’t think I was an exhibitionist, but it seems my fantasy landscape has been forever revolutionized by this incident…

• Ugh, there is something so hot to me about the process of teaching someone how to get you off. And especially that moment where they start to get it and do it how you want it without being told. I got to be on both sides of that this month, with regards to spanking, fingering, and blowjobs, and maaaan I was into it. Good sexual communication forever!

 

Sexcetera

• My main sexual adventure this month was losing my anal virginity. It was awesome. I want to do more butt stuff real soon. (I probably won’t get to, though, because it’s something I’d only want to explore with a trusted partner, and I don’t really have access to any of those at the moment. Booooo!)

• The award for weirdest sexual adventure of the month goes to the time I got kissed, fingered and felt up on an Airbnb balcony while slightly stoned, as snow came down around us. Marijuana often impedes my ability to tell whether the situation I’m in is strange or not, because everything feels strange when I’m high. But yeah, even looking back, it was a surreal experience. I don’t think I will ever forget the feeling of his hands sliding up under my bulky winter coat as he backed me up against that cold glass railing. Swoon.

• My friend is developing a party game called Don’t You Dare and I got to play it a few times this month. It’s really fun! I have some feelz about the ways in which games like Truth or Dare can be immensely helpful and world-widening for anxious folks like me… Maybe I’ll blog about that one of these days. (If you wanna help fund the game so it can liven up your parties someday, you can do so at its GoFundMe page!)

 

Femme stuff

• It was a big lingerie month for me. I am expanding my “porndrobe,” as it were. Some of my fave new sexy acquisitions are a navy and teal lace set by QT Intimates and a pink floral lace set by American Apparel. Now I wanna get more boy briefs and thigh-high socks, but what else is new?

• While searching Redbubble for “heart-eyes emoji” – as you do – I found this zip-up pouch. I had been in the market for a case in which to carry safer sex supplies (condoms, lube sample packs, gloves, dental dams, maybe a small vibrator), and this fit the bill, so I bought it. It’s actually a little bigger than I would prefer for everyday sex-supply totin’, but when I packed a huge bag for my hotel-sex date, it fit a noble quantity of latex barriers and butt plugs. Hooray!

• I bought a black and white skull-print scarf for something like $4 at a vintage shop and it is the ideal thing for tying around my hair when it’s in pincurls. Such glamour!

 

What were your fave sexy things this month, darlings?

How to Have Anal Sex For the First Time (If You Are Me)

Kate Sloan

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Begin innocuously enough. Go out for dinner with the crush/bang-buddy/friend to whom you’ve just given a blowjob. Get a little drunk with him, on big pints of locally-brewed beer, and laugh at all the jokes he’s making because weed and BJs make him cheerful.

While talking about your sexual goals for the year, suddenly have a brilliant idea – but the kind of idea that maybe only seems brilliant because you’re drunk. Start to tell him, but think better of it. Cover your mouth with your hand. Blush a lot. Shake your head. Let him pry it out of you, because the more that you keep it inside, the better an idea it seems. Finally: ask him if he wants to be the first person to fuck you in the ass. Because you want it. Because you trust him. Because he’s been on both sides of butt stuff plenty of times before and knows what he’s doing.

Be pleasantly surprised when he immediately agrees, and yet also not surprised at all, because he’s sweet and chill and adventurous and seems to genuinely like you. Concoct a plan with him, involving a hotel room and hours of slow, luxurious warm-up. Nod sagely when he tells you, “Let’s sleep on it and decide tomorrow,” while knowing in your heart of hearts and butt of butts that you’ve already decided and the answer is yes. Pay the cheque and tipsily stumble back to his place together. Give him one more BJ for good measure before saying goodnight.

The day before, text all your friends and tweet to all your followers about your sodomous plans and get their advice. Put your favorite butt plug in and leave it in for hours on end, to re-acclimatize your ass to penetration after a long stretch of none whatsoever. Masturbate idly while the plug is inside you, savoring that weird mix of pleasure and unfamiliarity. Wonder idly if you should’ve invested in an anal thruster for a more realistic warm-up.

Send dude a link to a cheap hotel listing, which is your indirect-and-yet-very-direct way of saying, “Yes, I still want you to fuck my ass.”

Pack a bag full – and I do mean full – of toys and other sexual accoutrements. Two Pure Plugs, the Ryder, and the large Ripple. Two bottles of lube. Black latex gloves. A zillion condoms. A tightly-folded Throe. The Pelt, incase of spanking. Salsa, Tango, and Hitachi. Put the Uncut #1 in there because you’ll want something roughly the same size as the dick that’ll be going in your ass, and when you put the Uncut in your mouth to test its size, you think, “Yeah, that feels about right.” Start getting real fucking excited.

While tipsy at a Valentine’s Day party, hide in the bathroom and sext the dude: “Very much looking forward to doing things to you with my mouth tomorrow.” Because you’re slightly obsessed with blowing him. Squeal when he texts back, “Bring toys.” Later, actually scream, at a totally inappropriate moment during the Valentine’s party, when he sends you a picture of a woman getting DP‘ed with toys. Because, holy shit, he’s going to DP you. Go home and add the Eleven and Double Trouble to your already-bulging toy bag because you suddenly want him to ram you with something big and heavy.

The morning of, do what you usually do when you’re anxious: journal a lot, listen to soothing music, and worry disproportionately about how to do your makeup. Have a breakfast of 3 Oreos and a cup of coffee, because you’re too nervous to eat real food and also because coffee will help clear out your system. Go about your day, running errands and writing and doing chores, while inevitably unable to focus on any of it.

As the sun starts to set, glaze your body in coconut oil so you’ll be nice and soft for him. Get in the shower and shave your legs, your armpits, your vulva, your butt. Like most lengthy femme rituals, this is more about the way it makes you feel than the way it makes you look: eliminate some of your anxiety by eliminating all of your body hair. Wash your body with Lush’s “The Comforter” shower cream, because smelling like berry candy makes you feel like the hottest, beautifulest babe. Fill a bulb syringe with lukewarm water, squirt it into your ass, jump up and down a bit, then let the water flow out of you. Do this a few times, until you feel confident and clean.

Put on some cute underwear, a comfortable outfit that’s easy to remove, and minimal makeup that won’t flake off if you end up face-down on a bed. Take deep, calming breaths and then dance your ass off (no pun intended) to energizing songs for a last-minute burst of confidence.

Walk to the streetcar stop, carrying your heavy-as-fuck toy bag. Ride the streetcar and wonder what the other patrons would think if the bag accidentally spilled open and they saw all your butt plugs and fancy dildos. Get off where Google Maps tells you to, and walk toward the hotel. Start feeling intensely dizzy, partly from anxiety and partly from the exertion of toting sixteen pounds of sex toys through snowy city streets.

Arrive at the hotel, which is small and strange and reminds you of The Shining if it was shot on no budget. Schlep your stuff up to the second floor and find the room number that the dude texted you. Smile when he opens the door for you, because he’s cute and you like him and you’re happy you’re gonna do this with him of all people.

Tell him you’re anxious. He is too. Assuage your nervous hearts with weed for him, gin and chocolate for you, and giggly makeouts for both of you. This is a never-fail prescription.

Give him a beej. For two reasons. One: his dick is excellent, and having it in your mouth turns you on faster than just about anything else. And two: if you get nervous and back out of your buttsex plans, you won’t feel as bad about it if he’s already come. This move is strategic. Or… strabeejic, if you will.

Lube up a Pure Plug and slide it into your ass, while he gives you sage advice on technique and angle, like some kind of butt sherpa. Laugh a lot, because he’s doing silly impressions and voices for your amusement, and think: yeah, I definitely chose the right person to do this with.

Let him do stuff to your nipples and clit and G-spot, because holy fuck, he has talented hands. Do your best to give directions, because sometimes you get too shy to boss people around but you know you’ll need to be a top-notch communicator tonight if he’s gonna fuck your ass. Don’t come yet – you wanna save that for later.

Bend over and let him take out your Pure Plug and switch it for the Ryder. Recall when you first bought your Ryder, years ago, and tried to put it in with no warm-up and not enough lube, and how goddamn awful and stupid that was. Enjoy the contrast between that moment and this one: the slick way he slathers lube on the plug and lines it up just right. The utter ease of taking a big toy when you’re really ready for it. The encouraging words in your ear as you back up onto it and it slides in, pop, no pain, no problem.

Make out some more. Touch each other. Giggle. Play. This isn’t a race. There’s no schedule. No marks to hit. No obligation to follow through. Just do what you feel like. Teach him how to spank you. Show him how you like your clit touched. Tug on his chest hair. Kiss his cute face.

Recognize your readiness by how relaxed you feel. Anxiety dissolved and apprehension bested, grab a condom and some lube and get him hard in your mouth. Pull the plug out, slowly. Bend over the edge of the bed with a Hitachi pinned between your clit and the mattress. Smile against the sheets, because this feels like a game.

As he slides into you, breathe deep, cleansing breaths of calm focus, and then fast, heavy breaths of unexpected pleasure. Moan, writhe, bite your lip, grind against the Hitachi. Think about how easy it was for him to push into you. How hot, hard and slippery he feels inside you. How good this is, how much better it is than you even expected. Feel completely safe, and taken care of, and respected, and filled, and fucked.

Stop him after a couple minutes, because the sensation is… a lot. Curl up beside him and high-five him when he announces, “So, you’ve officially had anal sex now!”

When he asks how he can get you off, let him choose between the Eleven and the Double Trouble. Smile as he weighs each in his hands, taking the decision as seriously as you knew he would. And then lay back and let him fuck you so perfectly with the DT while the Hitachi’s mashed against your clit, until you come in the long and loud and wild way that you only ever come with partners who make you feel unashamed. Kiss his big lubey hands when he wraps his arms around you afterward and says, “That was hot.”

Once you’ve come back to earth, put your clothes on and go out for celebratory dinner and drinks at a nearby pub. Because, hell yeah, good sex is worth celebrating.

 

This post contains a sponsored link. As always, all writing and opinions are my own.