When Sex Nerds Plan a Threesome

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This weekend, I’ll hop on a bus and ride it for 10 hours, into another country, where I’ll have my first out-of-homeland threesome. We’ve been planning it for six weeks. Those weeks have felt like years.

See, both of my previous threesomes were impromptu – happy accidents of timing and circumstance. This one was deliberate, chosen, considered. I can see the merits of both approaches: spontaneous sex gives my anxiety less time to take root and psych me out, while long-haul schemin’ allows for excitement to build like a pre-record-launch hype campaign.

Any activity is more fun if you’re doing it with people who love it. That’s true of sex, and it’s also true of planning sex. Both of my threesome co-conspirators in this case – Bex and a gentleman friend of ours – are as nerdy about sex as I am. This made our brainstorming, scheduling and co-ordinating into a delightful process, like planning a party… except with more sexting.

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The Negotiations

When you think about sex critically and deeply on a regular basis, you become more aware of what you want, what you like, what turns you on – and what doesn’t. Once you know what you want, the next step is to ask for it. That can be scary sometimes: our carnal cravings are so close to our hearts and entrenched in cultural shame that often our inclination is to downplay our desires. But I’m lucky enough to be having a threesome with two people I deeply trust, who I know would never shame me for articulating what I want.

In weeks of chatting and spitballing, we came up with some mutually exciting activities to include in our threesome docket. And the best part of it is, all three of us are so easygoing and invested in each other’s enthusiastic consent that we know we can abandon anything on the list if it feels wrong on the day of. “We’ll just be like a bunch of little puppies,” dude said to me in one of our many excited exchanges about threesome logistics. “We’ll try stuff out.”

Bex and I are solely-platonic friends who engage with each other sexually on a very limited basis, so part of our negotiations involved setting boundaries for what we will and won’t do to each other. Fortunately, we were on the same page about everything we discussed: we’re cool with doing a double BJ, making out, and some boob stuff, but below-the-belt action is off the table except for maybe manoeuvring dildos.

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The Feelz

Sex nerds understand that sometimes sex stirs up feelings, and the best defense against icky feelz is to talk them out, before, during and after your experience of them. Good communication where everyone feels respected, heard, and valued = good sex, with minimal drama.

The dude in our trio is someone with whom I have sexual history. He also gives me hella heart-eyes feelings, and I sometimes struggle with jealousy when I really like someone. Both he and Bex repeatedly made sure I was okay with “sharing him,” before and during the planning of our ménage. Though I might have felt gross if he’d jumped into the three-way headfirst without regard for my feelings, the amount of care he took with me put me at ease. As of right now, I’m not feeling a shred of jealousy – but I know that if I do feel strange on the day itself, I’ll have two friends there to talk it out with.

If you find yourself dealing with similar jealousies leading up to a threesome, think about what kinds of accommodations might help with that. I asked Bex if I could be the one to swallow dude’s cum after we blow him together, because being “rewarded” with jizz at the end of a beej feels satisfyingly intimate to me and I think I’d be sad if I missed out on it. Bex said yes, ’cause they’re an angel.

Bex has also recently started using they/them pronouns full-time and publicly identifying as non-binary, and that entered into our pre-threesome talks as well. Dude was amenable to learning about gender stuff, especially since he knows getting it wrong could kill the moment – so we talked about what pronouns, names and titles were and weren’t okay. Yay, respect and correctness!

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The Gear

I know all you sex toy nerds are curious about what I’m bringing, so here’s a rundown:

• Pegging may or may not happen, depending on the Whims of the Butthole. I’ve packed my pink Aslan Jaguar harness. Assuming we get the go-ahead, it could either be me or Bex who’ll do the fucking; we’ll see how we feel. I’ve also packed my bright blue Happy Valley Perk, because it feels the most like “my cock,” though I’m open to strapping on other dildos too.

• Dude likes using toys on people, and has proven his prowess at doing so. Bex and I think it’s hilarious to imagine him fucking us each simultaneously with our own Eleven or Double Trouble, so I’ve packed both of mine. Dual-wielding!!

• Vibe-wise, I’m bringing my Magic Wand Rechargeable and maybe my Tango. I just need something reliable to hold on my clit while dude finger-bangs me or pounds me with a toy or fucks me… Um, no, I’m not blushing! Why would you say that?!

• Bex and I like when I spank them, so that’ll probably happen during this threesome. They own all our favorite implements (including the almighty Pelt), so the only impact toy I’m bringing is my Maddie’s Dungeon wooden paddle, ’cause it’s cool.

• I threw my Ryder in there because last time I slept with this dude, he liked how tight my vag felt when the Ryder was in my butt. I am always eager to please.

• Like a Boy Scout, I am prepared as hell: my sex toy bag is topped off with dude’s favorite condoms, some lube samples, and black latex gloves.

Have you ever planned a threesome? What was the process like for you? (And what toys did you bring?!)

12 Days of Girly Juice: 5 Sex-Positive Superheroes

I’ve been avoiding writing this post, because… it feels weird to single out just five people who affected my life in the sex-positive realm this year. There are so many of you, and all of you affect me in different and important ways. The world is full of badass sex educators, brilliant sex bloggers, and magnificent sex mentors. It was so, so hard to choose just five!

That said, it also wasn’t hard, once I sat down to really think about it. These are the five people whose contributions to my sex-positive endeavors meant the most to me this year. I’d love to know who your sex heroes were in 2015!

 

Sophie Delancey

Sophie had a really tough year. She had a series of strokes early in 2015 that affected her mobility, eyesight, voice, sensation, and – yes – sexuality.

I haven’t known Sophie that long, but for the entire time I’ve known her, what I’ve admired most about her is her tenacity and how hard she works – all while managing to stay sweet and positive. She held onto those qualities even in the face of extreme adversity, and that is absolutely astonishing to me.

When I did the Miracle Worker course earlier this year, one of the exercises was to reflect on whose career makes you jealous, and why. Sophie was one of the names I wrote down (along with Piph – see below), because her work spans multiple mediums in sexuality and seems fascinating and fulfilling. She’s always busy and always hustlin’, and I admire the hell out of that.

Here’s sincerely hoping for a better 2016 for Sophie – she deserves it!

 

Samantha Fraser

Samantha is the brains, brawn and beauty behind the Playground Conference. If you were there and (like me) had a fantastic time socializing, learning, and laughing, you owe all of that to Samantha. She worked tirelessly to make the conference happen and has done so for the past five years – and it’s paid off, in the form of an event that everyone loves.

Along with Sophie, Samantha also runs Tell Me Something Good, a local sexy storytelling event (more on that in my next post, which is all about events!). Obviously, she is a master community-builder, and that is a remarkable and rare skill.

I recently started reading Samantha’s book on ethical non-monogamy, Not Your Mother’s Playground, and it’s made me reflect on how much I owe to the polyamorous role models in my life, Samantha included. I can’t imagine viewing poly life as a viable choice for myself without the influence of those people, telling and showing me it’s okay if monogamy doesn’t feel right for me. Samantha’s contributions to Toronto’s vibrant sex-positive community are huge and shouldn’t be underestimated!

 

Stoya

I don’t have a lot to say about this situation, because it pretty much speaks for itself. Stoya spoke out publicly about James Deen raping her, and this admission triggered an avalanche of similar revelations in the industry. She is singlehandedly responsible for toppling an insidious industry giant, and she should be revered for her bravery forever.

 

Epiphora

2015 was the year when Epiphora transformed from my far-away hero into my real-life friend – but, let’s face it: she’s still a hero of mine.

It was Piph’s blog that made me first want to start this one, way back in 2012. She widened my purview of what a blog could be, what sex toys could do, and what women are “allowed” to say about our own masturbation and sexuality. She’s one of my favorite writers in the whole world and certainly the funniest and most thorough sex toy reviewer on the entire internet.

Piph also deserves props for helping – by which I mean, forcing – me to move my blog from Tumblr to self-hosted WordPress this year. “Your blog is too good for Tumblr,” she said to me the very first night I met her, over mac and cheese and red wine. “You need to buy hosting. Like, now.” I had always been apprehensive about doing this because of my lack of back-end blog knowledge, but Piph saved the day: she got me a terrific deal on hosting, set everything up for me, and helped me with countless coding quandaries in the months to come. This blog would be nothing without her.

Piph is amazingly strong and outspoken, and she taught me a number of lessons along those lines in 2015: “Never apologize.” “Always get paid before you do the work.” “Believe in your vagina.” She’s like the cool, tech-savvy older sister I never had – who just happens to own more than 500 sex toys.

 

Bex

Welp. Let’s see if I can write this without crying…

I met Bex at the sex bloggers’ retreat she helped plan in Oregon this past June. Prior to that trip, she and I weren’t all that familiar with each other’s blogs – but as we got to know each other in Oregon and in the months that followed, it became abundantly clear that we are #SexBrainTwins. Seriously, I can’t even count the number of times that we’ve stumbled upon a similarity in our kinks, desires, or experiences, and shouted at each other, “TWINS!!”  or “WE’RE THE SAME!!”

We get anxious about a lot of the same things, but we each have a nurturing, supportive streak that means we’re able to talk each other down in times of anxiety. I owe a lot of my sexual and romantic success this year to Bex, because whenever I wonder “Does [boy] really like me?!” or “Should I ask him out?!” or “Am I actually worthy of desire?!” my friend Bex is always there to remind me of my inherent value, and to calm my nerves.

We even had a threesome together with a cute boy we both like, and it wasn’t weird at all. Our relationship is platonic, but also not. “We have sex near each other, not with each other,” I remarked to her recently, while staying at her house, where I masturbated in front of her, spanked her, and told her what a babe she is, without any of that feeling strange.

Bex is one of the most organized, prepared, patient people I know. I never tire of talking about sex with her, but let’s be real: we could probably talk about anything and make each other giggle hysterically. She understands me and she also punderstands me. I feel so blessed to have such a wonderful friend.

 

Thanks so much to all the sex-positive people I communed with in 2015, not just these five. I love you all and you add so much value and joy to my life on a daily basis. ♥

Playground Diary, Part 2: Macarena, Mollena, & Mac & Cheese

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Where I left off, Bex was patiently waiting for me to put my makeup on for Playground prom. (Applying silver glitter eyeshadow can be a fairly involved process, as you might know.) We put on our sparkly dresses, grabbed Greek takeout, and shoved it messily into our faces while riding the subway back to the hotel. (We classy.)

The prom was sooooo much fun, and I say that as someone who normally hates anything involving a club-y or dance-y atmosphere. Usually that sort of vibe gives me massive anxiety and introvert exhaustion in short order. But the entire Playground Conference was set up to be a safe(r) space, and there were so many friendly faces everywhere I went, that I didn’t feel nervous at all. I danced my ass off with lovely humans the whole night: we literally stayed until the DJ said goodnight and they turned the lights back on.

Some prom highlights: Shrieking with excitement when a Justin Bieber song came on. ♥ Rogue (who is more outgoing than me, and therefore more capable of interacting with strangers) asking the DJ to play the Macarena on my behalf, and then getting to Macarena real hard with a bunch of other enthusiastic weirdos on the dance floor. ♥ Remembering midway through the evening that I had a paddle in my bag, and letting folks use it on each other. ♥ Laughing so hard at a cute boy’s Christopher Walken and James Spader impressions that I had to immediately announce “I have a huge crush on you,” which caused him to kiss me. ♥ Shrieking along with the high notes in Senorita. ♥ The total acceptance with which Lavender was greeted when she decided the dance floor was too hot and took her dress off.

There was to be a sexy after-party when prom ended – after all, post-prom is the time to lose your virginity… or, um, have a kinky orgy in a hotel room… – but I was too tired to party any more, so I ended up going home to sleep in a handsome man’s bed. (No, really. Just to sleep. I was tired as fuck from all that dancing!)

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After creeping home in the morning to shower and get dressed, I subwayed back to the hotel just in time for JoEllen and Stephen‘s talk on sex and depression. There was a remarkable feeling in that room: it felt like the crowd was hungry for the information being shared. Like all of us who’ve suffered from depression, and who have struggled with our sexuality as a result, were dying to both hear about others’ experiences in this regard and share our own. It’s true what JoEllen says about sex and depression, that it’s a difficult topic because it’s the intersection of two taboos – and that’s also what makes it so intensely freeing when you do get to hear about, and talk about, that intersection.

That session was fantastic, but also quite heavy, as you might expect. So when I received an invitation to a hotel room cuddle party immediately afterward, I accepted on the spot. Cuddles with sex-positive cuties are an excellent treatment for the sads. We took the elevator up, and our cuddle party devolved into a sleepy sex-pile. (I mean… It was a sex conference. Did you really expect our cuddles to be chaste?)

12224521_1132535596757421_182425694_nWhen the owner of the aforementioned hotel room had to check out of it, we were faced with the task of finding a new location for what had become an emergency threesome. I hesitate to write too much about the fun and funny fuck-times that ensued – I’d rather keep it in reserve for Tell Me Something Good or more private settings – but let’s just say it was gooooood.

Threesomes, and group sex in general, make me nervous as hell in theory. It feels like there’s so much that can go wrong, so many ways that one person can feel like a third wheel or that everyone can feel awkward and uncertain. But luckily, that hasn’t been my experience with either of the threesomes I’ve been in. I guess I know some good people!

We finished up and got on a streetcar back to the hotel, where we arrived just in time for the final keynote with Mollena Williams and Herr Meister. It was a really wonderful ending to the conference because it was so low-key: instead of being a structured speech/talk, it was really just a dialogue between Mollena and her Master about their relationship. I think it was exactly the emotional cooldown we needed to help us transition back into “real life” – almost like non-sexual aftercare.

In her closing remarks, Samantha suggested mac and cheese as a viable self-care strategy for dealing with con drop. Bex and I took that idea and ran with it. After hugging folks goodbye – and returning the threesome-location key we’d borrowed – we returned to 7 West for massive quantities of comfort food. We ended up talking for 4 hours or more, just debriefing about the weekend, and it was truly the perfect conference wrap-up. ♥

Thanks so much to Samantha Fraser for making the Playground Conference happen, and to all the folks who traveled from near and from far to attend it. It was ridiculous amounts of fun and I feel so grateful to be a part of this community. Love love love!

Playground Diary, Part 1: Biscuit Porn, Short Skirts & Special Brownies

Ha. Remember last week when I prophesied that Playground would be “one of the best weekends of my year”? Yep, I was right.

imageMy Playground adventure began with a Thursday-night porn party hosted by the beautiful and wonderful Kate Sinclaire. Kate knows porn: her softcore site Cherrystems and soon-to-launch porn site Ciné Sinclaire are the cat’s pajamas. She showed us some stuff she’d been working on, all of which was hot and fresh and compelling. Then we watched various other clips, including this adorable one in which Zander Storm shows you how to make biscuits, while wearing nothing but an apron. CUTEST.

I got to meet several cool folks at that get-together who I would see intermittently for the rest of the weekend – including Rogue, who has been a Snapchat buddy of mine for ages! Yay!

The next day, I had two psychology exams practically back-to-back, and got through them only by reminding myself that I was going to Playground that night.

imageBex came over to my house and it was sooooo good to see her again. (We last hung out at SHE and, before that, at DildoHoliday.) She waited around for me while I got ready (a recurring theme of the weekend – sorry, Bex) and then went for dinner at my fave, 7 West. From there, we headed over to the hotel where Playground was taking place.

We missed the opening keynote but arrived in time for Tell Me Something Good, the monthly sexy storytelling event which is always one of the highlights of my month. I got to see (and introduce Bex to) a bunch of my favorite folks from the local sex-positive community. We got drinks, listened to stories, and laughed our asses off. (Dan and Tynan are two of the most hilarious people I know.) I even got to tell a story of my own – in a very, very short dress. Whoops.

We went upstairs for a tiny, intimate hotel room party that involved “special” brownies, Truth or Dare, and ridiculous mispronunciations of the word “boudoir.” Ooh la la.

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Bex and I began our Saturday morning at a talk on solo polyamory, given by Eva Dusome of Polyamory Toronto. I am just at the veeeery beginning of my foray into poly life, and while this workshop wasn’t the 101-level introduction I probably needed, it still gave me a ton of insight and food for thought about what kind of poly person I might want to be. By the time the session ended, my brain was positively abuzz with thoughts of autonomy, connection, individuality, introversion, the illusion of control, and the ways in which self-care is vital to relationships.

After that, we went to Create Your Own Porn, a panel featuring (among others) Kate Sinclaire, Sophie Delancey, and Taylor J. Mace, three of my favorite pornographers who also happen to be three truly delightful people. Also there was Sonya JF Barnett, whose work I remembered from a feminist porn screening I attended earlier this year. They shared many useful tidbits about the technical and back-end side of porn creation, probably launching the careers of several audience members with porn ambitions!

imageAfter lunch, we had intended to go to the Spit erotic boudoir shoot, but there was a huge lineup (yay, good for them!) so we went back down to the exhibitor room instead. I bought some fancy lingerie from EmMeMa and we also ogled leather kink goods, stainless steel sex toys, and fetishistic femme hair accessories. It was truly a cornucopia of Cool Sex Stuff.

It was fitting that I followed up lingerie shopping with a panel on femme identity. Some femmes on this panel I already knew, and some I didn’t, but all of them brought perspectives to the table that opened my eyes and engaged my heart. This was easily the most emotional session of the weekend for me, because femme erasure, femme competition, and femme underappreciation are all things I’ve experienced and things I’ve felt stupidly alone in. So much of what the speakers said was relatable, not only to me but seemingly to everyone else in the room. The sense of crowd-wide solidarity was palpable and it took a lot of restraint for me not to cry – but I don’t think anyone would’ve judged me if I had.

After that last session, I located Bex and we headed back to my place to get ready for prom night… (This story to be continued in part 2 of my Playground diary!)

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?