How to Prepare For a Casual Sex Date

I’ve written to you before, dear readers, about my fascination with casual sex. It was one of my sexual goals for 2015 to have casual sex at least one time, and I defined it thusly: “sex with someone I am not, and do not intend to be, in a romantic relationship with.” And by that metric, I have indeed achieved this goal as of late. Hooray!

As an anxious person, I like to be hyper-prepared for every eventuality. And this is why, before a potentially nerve-wracking situation like a hook-up, I have a pre-game ritual that gets me happy and hyped while keeping me safe and sound. Whether you’re finally gettin’ physical with a long-time crush or just looking to meet a fuck buddy online for a quick bang, I hope these tips will be helpful to you!

 

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Physically…

• Do whatever “body maintenance” is going to make you feel sexiest and most confident. Shave your legs, trim your pubes, groom your beard… Condition your curls, paint your nails, exfoliate your lips… Rinse your vag, scrub your balls, wax your butt… Whatever’s going to amp up your self-esteem for the evening, do that. Try not to let conventional beauty standards muddle your own personal standards too much, because if your date doesn’t enjoy the typical state of you, you probably shouldn’t be fucking that person anyway, right?

• Pick out an outfit that makes you feel hella desirable and cute. Bonus points if it’s relatively easy to remove in a hurry (you never know when things will suddenly get sexy) and if your undergarments are on-point.

• Get checked for STIs if it’s been more than a reasonable amount of time since you’ve done that (i.e. if you’ve engaged in any potentially risky sexual activity since your last test). Know the score before you get in the game. That way, you can confidently tell your partner what’s up and neither of you will have to worry. (Hopefully they’ll be as considerate as you in this regard!)

• Stock your bag and/or pockets with any sex supplies you’ll need. Fragile stuff like condoms and dental dams should ideally go in some kind of hard case to keep it safe from heat and warping (don’t cram your condoms into your back pocket and then sit on them all night!). If you bring a vibrator – which, if you like vibration, you should; don’t let anyone shame you! – do your best to pick one with a travel lock function, or at least place it in your bag in such a way that it won’t turn on before you want it to. If you want to be extra prepared, bring along some lube samples as well.

 

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Mentally…

• If you have any hangups whatsoever around the sex you’ll be having or the person you’ll be having it with, I prescribe a good long journaling session. Ask yourself: how do I feel about this? What do I hope will happen? What do I hope to get out of this? What is it that I like about this person? Where do I see this going? Some people are blessed with the ability to have sex without overanalyzing it, but if, like me, you just didn’t get that gene, journaling may help you get your head on straight.

• Consider your dealbreakers and know when you’d walk out. This is a scary thought, but it’s worth thinking about in advance. If someone exhibits a red flag, like refusing to go down on you or making a weird comment about your body, it’ll be that much easier to get up and leave if you’ve already identified your red flags in your mind.

• Figure out where you’re going, how you’ll get home, how much transportation will cost, etc. Don’t get stranded! And since casual sex goes hand-in-hand with intoxicants for some people, make sure you know this information well enough that you could recall it even if you were kinda tipsy (or more than “kinda”). Don’t be that shitfaced sadsack on the subway who can’t figure out where the hell they’re going.

• While you’re getting dressed, doing your face/hair, etc., put on a playlist that puts you into the optimum sexy mood for your fuck-date. I am all about Alina Baraz and Reverie Sound Revue; there are also tons of sultry mixes on 8Tracks that’ll help you get your vibe right.

 

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Verbally…

• I know it’s hard, especially if you’re shy, but try to establish some expectations with your sex-partner-to-be. It’s tough to be brave and say exactly what you want and what you don’t want, but it’s worth doing to avoid the hassles that accompany miscommunications. What if you like your casual sex with a side of cuddling and talking about feelings, but your potential fuck-buddy just wants to get ‘er done and leave? What if you absolutely hate sleeping next to someone but your dalliance expects to stay all night? You don’t necessarily have to spell these things out so explicitly, but try to read the person’s tone in your communiqué, at least, to get some sense of whether you’re on the same page.

• Think about what you want and practice asking for it. This can be especially hard with someone you’ve never slept with before and/or don’t particularly intend on sleeping with again, but it’s worth doing if you want your experience to be a good one. People generally enjoy knowing what’s expected of them and being asked to do sexy things in a respectful, polite way, so if you can nail that skill, you’ll ensure a more fun time for both of you.

• Tell a friend or two about your plans. Fill them in on where you’re going, when you expect to be back, whether or not you’ll be reachable, who you’re going to see, and where potential sexytimes might be taking place. If you’re worried about your safety, maybe set up a codeword system with a friend: she’ll call you at a specific time and you’ll have a fake conversation, during which you’ll casually use a particular word if everything’s fine, and a different word if things are going downhill and you need her to send help.

 

What’s your pre-sex-date ritual? Do you define “casual sex” differently than I do?

 

Note: this post was sponsored, but as always, all writing and opinions are my own!

A Tale of Three Blowjobs: Getting Over Penis Terror, Continued

My very first post on this blog was about something I termed “penis terror.” Maybe that doesn’t bode especially well as a kick-off to a sex blog… but at the time, it was the main sexual issue occupying my mind.

See, when I was a youngin (by which I mean age 15–18), penises – and men in general – made me very, very nervous. I had a plethora of anxieties and neuroses about male sexuality. I believed men were hard-wired to be sexually aggressive, to put their own sexual desires above women’s, and to judge women’s sexual performance against impossible pornographic standards. And that shit terrified me.

It’s so embarrassing and strange to recount this now, but in my first sexual relationship with a cis guy, I literally cried the first several times his penis was brought up in sexual conversation. I was so fucking nervous and I can’t even explicitly identify, in retrospect, what was making me so nervous. It was just a fear of the unknown, I guess.

I worried I would be bad at pleasing penises, and that my boyfriend would judge me or leave me for it; I worried that touching penises would somehow make me “slutty” or “tainted,” even though I intellectually knew these are bullshit concepts; and, maybe most frighteningly of all, I worried I wouldn’t like penises. I was petrified that I’d turn out to be biromantic but homosexual – because I knew I wanted to date and kiss and cuddle with men most of the time, but I didn’t know if I also wanted to fuck them. And that was a scary, dicey question hanging in the air.

 

But my feelings about penises have transformed monumentally over the years. I crave them, I appreciate them, I write them love songs and gratitude missives. They’re kind of one of my favorite things.

There’s no clearer barometer of my penis-comfort than my attitude about performing oral sex on them. So, for your amusement: a tale of three blowjobs.

 

1.

My journal entry for July 5th, 2011 begins: “Today will go down in history as the first time I ever put a penis in my mouth.” A tad dramatic, perhaps, but it really did feel that significant to me.

I was nineteen years old. My very non-scientific Twitter poll indicates that this makes me a relatively late bloomer. What can I say? Willies gave me the willies. But when I did finally get around to it (with some very gentle prompting from my then-boyfriend), it wasn’t anywhere near as bad as I thought it was going to be.

Granted, he didn’t come in my mouth that first time, which definitely made it easier to handle. But, overall, I considered it a huge step forward and an even huger relief. I had a major fear reference; I felt invincible.

“Throughout all of this penis stuff,” I wrote in my journal, “I have learned that there are two things I need in order to comfortably jump into a fear: a supportive, loving, respectful environment, and a little push.”

 

2.

After the aforementioned First Penis In My Mouth (and its owner) exited my life, I started to wonder if the same fears would rear their head again when I got another dude into my bed.

I broke a long dry spell by romancing a cute guy from the internet. During the proceedings, he very politely asked if I’d go down on him, and I immediately did, and it was good.

It wasn’t until a couple days later that it occurred to me: Huh. What took me literal months of waffling and wailing with my first serious boyfriend only took one respectful request with a hook-up. I guess I really am over that fear at long last.

The one fellatio-related anxiety that lingered for me, though, was being watched while going down. Maybe it’s linked to my fanaticism over blowjob porn and some shitty internalized ideas about “sluttiness,” or maybe it’s just insecurity about the way I look, but I’ve always hated being watched while giving a BJ.

I explained this to Adorable Internet Hook-up and he seemed to have no problem with it whatsoever. We turned off the light and all was fine and good. But, well, you hear a lot of things about how the visual of a BJ is almost as important for men as the actual sensations. Obviously preferences vary from person to person, but as someone who loves watching, say, Heather Harmon inhale a dick, I totally get the appeal. And I was bummed I still couldn’t be looked at while my mouth was full of cock.

 

3.

Shortly thereafter, I had sex with a… uh, how do I even put this? A friend who I also now like to kiss and have sex with? (Um, obviously I am new to this whole sex-outside-of-relationships thing, but, semantic difficulties aside, it is fucking great.)

When a blowjob became imminent, he grabbed his glasses off the nightstand where he had set them during our makeouts. I asked him what he was doing and he said, “I want to watch.”

For some reason I didn’t even think twice about this. I guess I was preoccupied by the prospect of a cock in my mouth. (Cocks!!!) As before, it took a day or two for my brain to properly process the magnitude of what had happened. I had let someone watch me blow him! And this had previously been one of my biggest sexual insecurities!

As we were putting our clothes back on afterward and getting ready to leave, the guy even said to me that he thought I’d look hot giving him a beej on my knees, and instead of reacting with terror, I just giggled with delight. Because, yes, this is a thing that I would like to do…

 

Did you have any anxieties or insecurities to deal with when you first started giving oral sex? How did you overcome them?

Review: Aslan Leather Crystal Blue Cuffs

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One of the reasons it’s so exciting to be sex-positive in Toronto is our proximity to Aslan Leather. They make top-quality leather kink goods in their tucked-away downtown hideout. Their stuff is handmade, gorgeous, and all comes with a lifetime guarantee. Ooh, baby, yeah.

They were nice enough to hook me up with some Crystal Blue Cuffs to try. Actually they offered me anything I wanted, but since I already have what is perhaps their best-known and most-lusted-after product – the Jaguar harness – I figured I’d give their bondage goods a shot.

These cuffs are right up my alley: blue (my fave!) and white, classic kinky styling, and androgynous in such a way that they can look super femmey on someone like me but could be boyish in someone else’s aesthetic context. Yuuuum.

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The cuffs are 2″ wide and have six holes that the buckle can go into. On my average-sized lady-wrists, the 3rd hole is the one in that sweet spot where comfort meets security. I’ve heard from other folks that Aslan is open to customization requests, so if you have particularly tiny or large wrists that these cuffs can’t accommodate (unlikely), they could probably help you out.

I find these cuffs verrrrry comfortable. They’re lined with vegan (a.k.a. fake) leather, which is softer than real leather and cushions your wrists slightly. The vegan leather is also a great feature for if your wrists get sweaty, because the moisture that could potentially stain real leather has no effect on the fake stuff. Brilliant.

aslan-leather-crystal-blue-cuffs-3As always with Aslan products, the leather of these cuffs feels gorgeously soft and broken-in, and has that classic leather smell that is deeply sexy but not overpowering.

The buckles have a hole in them that enables you to padlock them, if you’re so inclined. Unlike kink products made by companies who don’t know their shit, these are designed with practicality in mind. You can’t wriggle out of them once they’re properly buckled and connected. In fact, during the photoshoot for this review, I kept having to ask my photographer friend to uncuff me so I could get into different positions!

The cuffs don’t come with a connector, but Aslan sells a basic one, as do a lot of sex shops. You can also just tie the D-rings together with string or rope if you’re feeling lo-fi (but make sure you’re able to cut yourself or your partner free in a hurry, incase of an emergency!).

aslan-leather-crystal-blue-cuffs-5The comfort and prettiness of these cuffs makes me inclined to wear them in non-sexual scenarios too, as fashion accessories. They’re just so damn lovely. If you can pull it off, I say, go for it: it’s a kinda-subtle and adorable way to advertise your kinkiness on the streets!

If you, like me, enjoy matching your ensembles, Aslan can fill that need for you: the Crystal Blue color scheme is also available in ankle cuffs, a collar, a Jaguar harness and a Minx harness. You would be the cutest submissive on the block if you had a little ensemble of co-ordinating kink-wear!

You can buy Aslan products on their website; a smaller selection of their pieces is also available through various other shops, like SheVibe, Come As You Are, and Early to Bed. And buy them, you should, because they are stunning, high-quality, and they actually do what they’re supposed to do: make your BDSM fantasies a reality.

Thank you so much to Aslan Leather for these wonderful cuffs!

Also: shout-out to my friend C.P. for taking these awesome photos. She also shot my bio photo and various other photos on my site, and is generally the best.

Review: Jimmyjane Iconic Wand

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It’s funny that Jimmyjane made a toy called the Iconic Wand when the sex toy world already has an iconic wand. It’s a bit like if Samsung launched a phone called the Iconic Smartphone (bonus points if it was formatted like “iConic”). Like, dude: you’re not fooling anyone.

But I should quit hatin’ on this toy, because it’s actually pretty decent.

My first exposure to the Iconic Wand was when JoEllen mentioned it while I was in Portland. She said that the controls were in an inconvenient place (which they are – more on that in a minute) but I was nonetheless intrigued by the wand’s beautifully simplistic look and its promise of “deep, rumbling vibrations.” So I asked Peepshow Toys to send me one to try, and they hooked me up, like the vibrator angels that they are.

Let’s get this out of the way: the Iconic Wand’s buttons are positioned so oddly that it seems like the toy wasn’t tested by humans prior to its release. Or at least, not by humans with normal wrists with bones and tendons. In order to switch the wand’s mode or speed one-handed, you have to hold it so far down the handle that you’re almost touching the head. Not ideal, Jimmyjane. The toy’s gently curved handle is otherwise very ergonomic and feels good in the hand; this vibe could’ve been improved substantially by just shifting the buttons a few inches up. But alas.

The controls themselves are easy to figure out. There’s a power button and a button that cycles through the wand’s modes and speeds. It has three solid speeds and four patterns, and while I don’t normally love patterns, these ones are kind of great: there’s not a lot of space in between pulses and escalations, so they can actually be a turn-on rather than a drag.

The vibrations are, as advertised, rumbly and strong. YAY. It’s damn impressive that Jimmyjane managed to pack such a punch into a toy that’s only about two-thirds the size of the Hitachi, especially given that Jimmyjane’s vibrations have historically erred on the side of buzzy and inconsistent.

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While I think the Iconic Wand’s vibrations are more than strong enough to give wonderful orgasms to most folks, it doesn’t work all that well for me, because of its shape. The top of the wand is completely rounded off, so I can’t tilt it for a more pinpointed sensation on my clit like I can with more angular wands. It delivers broad, all-over vulva stimulation, unless I use my other hand to hold my labia wide open – and who wants to do that when that hand could be operating a dildo instead?

The Iconic Wand also vibrates the fuck out of my hand no matter where I grip it. Grrr.

But, you know, it looks very pretty while it’s doing that.

I think the Iconic Wand is a marvelous choice if you want a super-powerful vibrator without the size or weight of a standard massager vibe. It’s elegant, waterproof (!!), has great speeds and patterns, and is possibly one of the best things Jimmyjane’s ever made. But if you need pinpoint stimulation or subtler vibrations, or if you have any wrist mobility issues at all, I would skip this one. After all, the Magic Wand Rechargeable is about $10 cheaper and it’s a tried-and-true classic – it is actually iconic, and for good reason.

Thanks so much to the good folks at Peepshow Toys for supplying me with this toy!

I Wear My Heart on My Belly: My First Tattoo!

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Way back in February 2015, I wrote this in my journal:

I want to get a tattoo this year. Maybe a heart on my lower belly. Something meaningful and sweet and pretty.

Seven months later, I finally made it happen: my external G-spot is now emblazoned with a red heart for all time. And I love it so much.

The day before getting inked, I did a marathon journaling session where I unpacked all the reasons, symbols and meanings behind this tattoo, to make sure that I really, really wanted it. And I did. Below, basically unedited, is that journal entry.

 


 

My “external G-spot” is an erogenous zone I discovered when I was with [my ex]. It likes firm pressure, especially when I’ve just had an orgasm. I wrote a blog post about this spot earlier this year, and for the post photo, I drew a red heart over the spot as a visual guide for readers. But I grew to like it so much after that that I wanted it tattooed.

I liked the idea of having a small tattoo there as a sort of “press here!” guide for sexual partners, and I toyed with the idea of making it a flower or even a 3D-looking button of some kind, but I just kept coming back to that red heart.

I’ve been made fun of by some friends for feeling such a deep connection to the symbol of the heart. It’s a little obvious, like saying your favorite band is the Beatles. But I just love it. It feels peaceful and encouraging and juicy and joyful and optimistic and romantic. It reminds me of first loves, first kisses, exciting crushes, youthful optimism about love. Hearts show up in my gratitude lists and happy journal entries a lot; drawing them in the margins of a notebook is like a little ritual that affirms: thank you, universe, for this blessing. I see it and I appreciate it and I love you.

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Having a heart in this particular spot would symbolize a number of different things. Like: I love my sexuality, my desires, my pleasure. I love my femininity, my vulva, my powerful babeliness. I love my belly, that little dip where it meets my mons, my chubbiness, my Venus de Milo-esque voluptuous foxiness.

Also, in the sense that the tattoo idea originated with me wanting it half-jokingly as a visual aid for partners, it is sort of an ode to sexual assertiveness and a reminder to always ask for what I want and to not be afraid to be specific, bossy, and slightly selfish in bed. It is okay to want things and to want a partner who will give you those things!

It’s difficult to be entirely coherent about this, I’m finding. But something just feels viscerally right about having a red heart at the literal centre and sexual centre and fertility centre of my body. As if to say: this body, this life, is dedicated to love. Love is at the centre of it, now and forever.

2015 feels like the right year for this heart to be branded on me. I’m 23: a woman, but still becoming an adult. Started on a trajectory that seems it’ll take me where I want to go, but unsure where that is, exactly. This has been SUCH a big year for me in terms of professional development, mental and emotional healing, relationship upheaval, gaining romantic and sexual confidence, and so much more, and it feels right to commemorate that.

I used to have a lot more tattoo ideas… Symbols and illustrations and phrases that I found meaningful at the time. But I can’t think of one more enduring and timeless than a red heart. I will always be committed to love and to self-love. And even if one day I’m not, it’ll always be something of which I ought to be reminded. Love is the most important, powerful touchstone, the fuel of my life, my guidepost and beacon and motivation. I want it on me, tangibly, visibly.

I was considering getting said tattoo on my left ring finger – a self-love reminder in the very place where a conventional symbol of love would go if I was engaged or married. But more and more things felt wrong about that, the more that I considered it. Finger tattoos fade more quickly; they are more difficult to conceal, should I ever need to; and I think it might take up weird psychic space if I were to have a pre-existing symbol in a place where a love symbol ought to go. That’s not to say I definitely intend to get engaged or married, but it feels sacred and proper to reserve that real estate on my finger, just incase. Hold space for what you want and the universe is likelier to deliver it.

Besides which: the origin of all the love and romance in my body feels intuitively much closer to my belly than it does to my finger.


 

Do you have any tattoos? What do they mean to you?