Yes Yes Yes And: Fail More, Fail Harder

Yes Yes Yes And is my ongoing feature on the parallels between improv and sex. Yes, I am a nerd. Enjoy.

 

When I’m in the mood to get reeeeal esoteric about comedy, I listen to the Backline podcast. And Rob Norman and Adam Cawley, ever men after my own heart, always serve up exactly the joke-laced philosophizin’ I’m craving.

One truth-bomb I’ve heard Rob drop in multiple episodes is that failure is good for your improv. The harder you fail, the more you get out of your comfort zone. The more you fail, the more you learn. Rob says, when he gets into a place of stasis with his improv, where he feels like he’s playing the same characters and relying on the same schtick all the time, the cure is failure. Doing something badly – whether on purpose or by accident – can be the shake-up you need to see your blind spots, fix your issues, and do better.

Well, guess what? That applies to sex too.

There’s this shitty cultural idea that sex should be seamless and wonderful from the get-go. You’re supposed to be able to read your partner’s mind and give them exactly what they want, because sex is “dirty” and talking about it is “unromantic” or “kills the moment.”

Fuck that, dude: communication is key. And sexual failure is also key. Because you could sit around all day talking about likes and dislikes, turn-ons and turn-offs, but there are some things you’ll just never learn until you get messy and try ’em.

My sexual “failures” are some of my funniest and most treasured sex memories. The times I choked on cock and had a mid-blowjob coughing fit… The time I tried to get bossy in bed and discovered I can’t even convincingly pretend to be a domme… The time I faked an orgasm when someone fingered me for the first time because I was too scared to give directions… It’s all taught me so much.

And even the less-than-funny failures were beneficial to my sex life in the long run. For every consent-disrespecting douchebag I’ve made out with, my resolve and self-respect have grown stronger. For every boundary I’ve loosened to impress someone cute, I’ve either expanded my limits or hardened them where I needed to. For every kink I’ve explored, I’ve deepened my knowledge of my own sexuality in one way or another.

You might recall that I recently had my first threesome, and while it was far from a failure, I learned soooo much from it about how I operate as a sexual person and what my patterns are. (More on that in another post, I promise.) I would’ve never stumbled on those realizations if I hadn’t tried something scarily new to me and kinda (arguably) fucked it up. At least, parts of it.

So, don’t be afraid to fail at sex sometimes. When you do something badly, you learn how to do it better. Or – at the very least – you have a good long laugh with your partner. Either way, you win.

What’s In My Bag: Fall 2015

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Do you ever look through the contents of your bag and just think, “This really sums up my entire personality/life”? I do that on the regular, but today was a particularly great example.

I recently bought this Zatchels shoulder bag, and while it doesn’t fit the zillions of items I would like it to, it can still hold a good amount of mostly-flat stuff. And it’s so damn cute that I don’t mind its low capacity too much.

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Today the bag contained (clockwise from top-centre):

  • My journal, without which I rarely leave the house. I always bring this with me when I go to work (for epic emotional unpacking on my break-time) or when I’m going to be sitting and waiting anywhere for a while (like on the streetcar or at the doctor’s office). Writing about my life helps me process its events, figure shit out and decide what I want to do next.
  • My iPad mini. This was one of those purchases that I thought I “didn’t really need,” but then I’ve ended up using it for soooo many different things. I often bring it with me when I interview folks for articles I’m writing, so as to record our conversations; I also listen to music on it all day at work, take notes in Evernote on it at school, watch movies on it when I’m bored, and so much more. It’s my constant companion and my surrogate brain!
  • My iPhone earbuds. Crucial. What would life be without music and podcasts?! I love that these earbuds have a little remote on them, so I don’t have to take my phone out of my pocket to pause the audio or adjust the volume. Brilliant.
  • My wallet, which is by Danier Leather. It’s so simple and classic and sexy. You’ve gotta carry a wallet so it might as well be one you like the look of!
  • Maybelline Creamy Matte lipstick in “Rich Ruby.” This isn’t even available in Canada yet so I had to order it online, but it was worth it. It is such a perfect red, and the formula really stays put on my lips without being too drying. Best!
  • My beloved We-Vibe Tango. Normally this would be by my bedside, but I packed it in here a few days ago because I thought I might be having sex that night and wanted to be prepared. The sex didn’t pan out after all, but it’s still nice to have a good vibrator on hand for all eventualities…
  • Lifestyles Tuxedo condoms. I find these hilarious because they’re black and supposedly for “formal occasions.” They also get pretty good reviews, sensation-wise, from both internet commentators and my ex-boyfriend.
  • Junior Mints. I practically fell asleep multiple times at my desk today while at work, and bought these to pep me up. They worked, but they also made my stomach hurt. Sad trombone.
  • Extra pen + pencil. A writer is always prepared!

What do you keep in your bag on the regular?

My First Threesome Was a Smash Success

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On Friday night I cracked open a fortune cookie and it told me my life is becoming more of an adventure… in bed. I didn’t give this prediction much thought, because, you know, it came from a fortune cookie.

But then, the next night, I had my first threesome, so maybe the cookie was onto something.

 

I have a beautiful, blonde, effervescent friend who I’ve known for almost 10 years. We met through Livejournal and bonded over a shared dorky enthusiasm for musical theatre. As it happened, we both ended up running in the same sex-positive feminist circles as we got older, so we’ve been reconnecting recently after a long period of mostly being casual-pals-from-afar.

She invited me over for what we thought was going to be a quiet night: dinner, conversation, and “Netflix and chill” in the literal sense. But then we went a little hard on the wine, some clothes came off, and we got into some slutty chats with her rowdy roommate… One thing led to another, and it was decided we should go out. My friend gave me a cute dress and jacket to wear, and we put on some sky-high heels and headed out to a loud underground bar.

She and I got to talking about a dapper dom guy we both know and have both banged, and we agreed (half-jokingly, except completely-seriously) that we should have a three-way with him someday. I am standing on the precipice of having a full-on Slut Phase and my blondie pal had agreed to be my mentor in this endeavor – my Slut Sherpa, or the Dumblewhore to my Ron Sleazy, if you will – and orchestrating a threesome seemed like a great way to kick that off.

When I get tipsy, I get flirty and text-happy, so of course we notified our mutual bang-buddy of our plan, not really expecting him to take us seriously. But, y’know, we’re foxy babes with feminine wiles, so he agreed pretty quick. “That’s a lot of babe for one dude,” he texted, to which I replied: “I think you can handle it.”

He met us at the bar and we cabbed back to his place. We talked for a long while, and did that tipsy thing where you all giggle over Facebook photos of your exes, and the boy let me borrow a pair of his socks because my feet were cold (quel gentleman). And then we migrated to the bed and cuddled a bunch. And boobs were (consensually) shoved into faces, and then she started giving him a blowjob while I kissed him… which I wish I’d been more alert/sober for, honestly, because holy shit, it was the logical next step in my blowjob porn obsession. Hnnnggg.

It’s often hard for me to remember the order of events in sex with just two people, because bodies blur together and pleasure makes brains into mush… so with three people, obviously this problem is exacerbated. Plus, when cute people are doing pleasurable things to me, my eyes tend to drift closed, making it hard to follow the action. But I do remember a cock in my hand, and mouths on my nipples, and a hand rubbing me through my panties, and fingers in my mouth, and a hand on my throat, and my tits being slapped, and and and… smiling-face-with-heart-shaped-eyes

Eventually my beautiful friend took off my panties and started going down on me. She had already displayed her blowjob prowess earlier in the night and now she was proving her cunnilingual skills too. I don’t know if you have ever had the experience of knowing someone platonically for a long-ass time and then having sex with them, but… wow. It is eye-opening and strange and fantastic.

If our threesome was a porn scene, what happened next would’ve been the centrepiece shot: he started fucking her from behind while she continued licking and finger-fucking me. His thrusts reverberated through her body so I could feel their impact too, so it was like he was fucking both of us. Ummm, yes.

I can’t remember too clearly but I think we wrapped things up with him coming in her mouth while I dozed beside them. (I am a sleepy person and had had a lot to drink, okay?!) And then we cuddled some more, and checked in with each other about our feeeeelings, and it was niiiice.

Afterwards, the boy asked me, “How many threesomes have you had before?” and I sleepily held up my hand in an “O” shape and said, “This many.” And then probably grinned like an idiot.
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When we got up to put our clothes back on, I found that my friend had neatly folded my underwear and the dress she’d let me borrow, and had put them in a pile for me. (Perfect sex partner etiquette.) We kissed our gentleman-pal goodbye and walked to the subway station together. She took this photo of me on the platform, and it sums up the whole evening pretty well: dishevelled post-sex hair, cute dress and jacket borrowed from her, warm boy-socks borrowed from him, red wedge heels I’d switched out for flats, and a goofy, sleepy smile on my face.

Shortly after this photo was taken, a random guy came up to us and asked us how our night had been. We burst out laughing, and my lovely amiga told him we’d “cemented our friendship” that night. He kept pressing us for details, and I don’t know if it was because I was tipsy or tired or just bursting to share the news with someone, but eventually I told him, “We just had a threesome with a guy we’ve both banged before.” The dude’s eyes practically fell out of his head, and we just laughed.

 

3 Cute Sex Toys For My Inner “Little”

My sexuality has taken a strange turn. And it’s fantastic.

It all started in a university class late last year. While listening to a hot lawyer lecture about freedom of expression and the Information Act, I found my mind drifting. “You’ve been a very bad girl,” said lawyer-dude in my transient fantasy, before tossing me over his lap, lifting my skirt and giving me a stern spanking.

When my mind finally snapped back to reality, I wondered, What the hell was that? Spanking had always been a mild interest of mine, but never in those fantasies had I regressed in age or craved a scolding. This handsome suited gentleman had awakened a long-dormant sexual persona in me: the bratty little girl who’s cruisin’ for a (consensual) bruisin’.

The age-play episode of Why Are People Into That?! just fanned the flames of my curiosity. And when I realized I had always felt sexiest in pigtails and schoolgirl skirts, everything made even more sense.

 

One of the ways you can explore “little space” to see if it’s right for you is by incorporating it into your masturbation. That way, you can experience that mindset before deciding whether to share it with a partner. And one of the most fun ways to do that, obviously, is with toys.

Here, then, are three products from OohSexToys.com.au that make my inner little girl want to cross her legs tightly and wriggle around in her chair…

 

If you’re gonna make-believe you’re a bunny rabbit, you might as well do it with a sweet-ass butt plug. This one comes in either silver- or gold-tone stainless steel, and the (faux) fur tail looks delightfully soft and sensual. Finish off the look with some bunny ears and a spot of pink face-paint on your nose, and you’ll be all set for a little-girl-pretending-to-be-a-rabbit scene. (A roleplay inside a roleplay? Is this Sexception?!)

 

Not to get too gender-essentialist on you, but hot pink is traditionally the color for little girls. Or at least, wearing hot pink makes me feel pretty damn little, in a very sweet way. Luckily, one of my favorite vibrators of all time, the We-Vibe Tango, comes in this saucy hue. Tie your hair into pigtails with some matching pink ribbon, pull up your magenta nightgown and go to town on yourself, little one.

 

Little girls like pretty things, and this glass dildo is basically a stained-glass work of art you can fuck yourself with. Its 1.3″ diameter also makes it a believable choice if you’re roleplaying as someone tiny: I love massive toys as much as the next size queen but I think my inner little might be put off by them.

 

Have you ever tried age-play, by yourself or with a partner? Does it creep you out or turn you on (or both)?

 

This post was sponsored, but as always, all writing and opinions are my own!

Monthly Faves: Spanking, Sexpo & Sideboob

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September was very sweet to me! (More like Sextember, am I right?!) Here’s what I enjoyed this month…

 

Toys

• It’s rare that I put a toy on this list that isn’t genitally-focused, but I would be remiss not to mention the glory that is the Tantus Pelt. I snapped one up this month after quietly lusting over it since its release, and it is absolutely the perfect paddle for me. The size, weight, thickness, and stingy-to-thuddy ratio are all on-point. Oh Tantus, you pervy geniuses.

• For one profoundly pleasurable evening, I borrowed a Fucking Sculptures Double Trouble from Bex, who was, in turn, borrowing it from Caitlin. I’m not sure I like it enough to drop $180 USD (~$240 CAD) on one of my own, but good heavens, the A-spot stimulation from the DT’s thinner/longer end made $240 seem like a small price to pay. Hmmm…

• I bought a Liberator Throe this month in a dark, glamorous New York sex shop. From my very first session with it, I could tell it was going to revolutionize my squirting adventures. It is a game-changer when you know you can actually relax and you won’t end up having to sleep on sodden sheets (or, worse, needing to wait until you finish your laundry before going to sleep). I used all my favorite G-spot toys with it and it valiantly protected my bed from squirt damage.

 

Fantasy fodder

• I’ve spent most of my adult life banging exclusively submissive and vanilla folks, despite knowing in my kinky little heart that I lean submissive. But then recently, I boned a handsome gent who is, as it turns out, very dom indeed. Needless to say, he occupied many of my saucier thoughts this month.

• My fave Toronto-based pornographers, Spit, put out a new video and it’s my favorite thing they’ve ever done. Granted, I know Jack and Lydia in person, so I feel a little closer to the action… but daaaamn, the subtle D/s dynamic in this scene is hot as hell and the performers’ playfulness melts my heart. (Side note: I dream of performing in a Spit scene someday… if I can find the right partner…)

• I am having aaaaall the little-girl feels lately. I mentioned “daddy kink” in my April faves when it first surfaced into my consciousness, and back then I felt very weird about it and struggled not to kink-shame myself every time it came up. However, I can’t deny that certain people just set off feelings of lusty littleness in me – like toppy partners who call me “good girl” and hot professors who teach me about child development. Unf.

 

Sexcetera

• In mid-September I went to a sexual health expo in New York, along with blogger pals Bex, Penny, Lilly, Lena, Hedonish, and more. We had some mixed feelings about the sexpo itself, but some of the presenters really blew my little sex-nerd mind. We learned about internal clit stimulation from Allison Moon, D/s boundary-setting from Mollena Williams, and sexual rut-breaking from Ducky Doolittle. It’s delicious to come home from an educational event with so many new ideas bouncing around in your brain!

• I’m writing a feature story about the Hitachi Magic Wand. As such, I’ve been carting my wand with me everywhere and occasionally delivering it to people’s homes so I can watch them use it as research. (Legitimate research… not pervy research… although, sometimes that too.) Life seems so much sunnier when you’ve got a Magic Wand in your inventory!

• I read through a lot of old journals this month, while trying to find one specific entry I wanted to reference in my blowjobs post, and I was struck by how gross it feels to read explicit descriptions of sex you once had with people you are no longer dating/attracted to. I’m glad I kept such a detailed history of my sex life from the get-go, because it’s crucial information when I want to look back and see how far I’ve come, but gawd it’s hard to slog through without gagging.

 

Fashion & beauty

• I did a lot of shopping in September. Whoops. Highlights: this Wednesday Addams dress from Modcloth (I was gonna wait til Halloween to show it off, but c’mon), a blue printed dress from H&M, and the glorious American Apparel acquisition I’ve been calling my “sideboob dress” (magically, it looks good on everyone). And speaking of my aforementioned little-girl inclinations: I ordered this from ASOS, and I think I need to put it on and convince some authoritative daddy-esque man to take me to a carnival and win me a stuffed animal or something. #LittleGirlSwag

• I am now the proud owner of a ring made to look like my vulva. Please give Catstache Accessories all your money because they did an incredibly beautiful job and got this masterpiece to me in a very reasonable amount of time. If you have fantasized about owning custom jewelry that resembles your genitals (and who hasn’t?!), I am telling you: now’s the time and Catstache is the place.

• Fall is officially here, and as such, dark lipsticks are my current jam. MAC Viva Glam 3 is the brownish-burgundy of my autumnal dreams.

 

What toys, fantasies and miscellany did you dig this month, lovelies?