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.

 

How to Celebrate your Breakupiversary

Holy shit, y’all: as of today, it’s been an entire year since the end of my last, longest relationship. It’s cliché, but it really feels like so much more time has passed than actually has. My reality has shifted, my identity has transformed. I am very much no longer that girl who blubbered her way through a break-up speech after months upon months of waffling.

However, not being sad about a break-up anymore doesn’t mean it completely fades into the history of your life. The anniversary of a relationship ending can still feel momentous and significant. I’m sentimental and I like to celebrate milestones as they pass, if just because it encourages personal growth. So here are some ways you could celebrate your “breakupiversary” if you feel like you want to…

Invite friends. Make it an event.

Your friends probably saw you through the break-up and the relationship itself. They remember how it affected you, what it meant to you. So they’re the perfect people to help you laugh about it, forget it, and move on from it.

Most of the suggestions below can be accomplished just as well with friends as they could if you were alone. How fun it would it be to put together an itinerary for a break-up party and email a detailed invitation to your nearest and dearest? The event could even have a dress code, like all black (for mourning), all bright colors (for optimism), or “wear something your ex hated.” Amazing!

Ceremonially destroy something.

The traditional way to do this is by burning: you could make a bonfire for the destruction of old letters and photos, or you could get witchy like Gala and burn that shit in a miniature cauldron.

If burning isn’t feasible for you, because it’s illegal, dangerous, or just unappealing, there are other ways to destroy old mementos. You could tear them up and throw them away, stomp on them, toss them in a body of water (if they’re biodegradable), or run them through a shredder. You could use them as the basis for an art journal spread, or shove the remnants into the bottom of a planter that you then fill with soil and a seedling, as a symbolic gesture that you’re movin’ on up.

Replace something that reminds you of your ex.

I know you have some object in your house that, every time it catches your eye, takes you to a dark place, even if it’s just for a second. It could be a perfume that smells like your first date, a stuffed animal your ex won for you at a carnival, or a sleep shirt you “accidentally” stole from him when the relationship ended.

Whatever it is, you should find a decent – better, in fact – replacement for that thing. Ideally, bring a friend or two on the shopping expedition when you do this, so there will be fun and funny memories attached to your new acquisition from the get-go.

Make a list of reasons your current life is better than it was during that past relationship.

I bet you can come up with like a zillion reasons.

Put on an angry/triumphant/sweet-ass playlist.

8Tracks has some good break-up ones. They might be a bit mopey for this celebratory occasion, though. “Emotionally Intense ’90s Women” is my favorite playlist for when I feel like being ridiculous and angry (thank you to the friend who turned me onto this playlist when my cat died and I just needed to scream along to Alanis). Anything that ignites that “hell hath no fury like a woman[/man/non-binary person] scorned” feeling in your gut is a good pick.

Dig out old journals and read them dramatically.

If your friends aren’t around for this part, hop on Periscope and do it there. You really need some kind of audience for this one (although, admittedly, I have spent many an afternoon re-reading my old journals by myself and absolutely guffawing over how silly past-me was).

If you’re in a boozy mood, you can make this into a drinking game. You know what your patterns are in relationships, so you’re best equipped to create the rules of your own game. But, for me, I’d probably take a shot every time I used the word “compatible,” wrote about a sex session in greater-than-necessary detail, or complained about a problem that could have been solved by better communication. Yawn. (Boozin’ aside, though: laughing at old diary entries is one of the best-ever ways to turn a sad situation into a funny one. You’ll feel so much lighter once you’ve cackled at your own misery.)

Have sex.

So many options! You could stay in and have sex with yourself. You could get it on with your current partner, if you have one, and reflect on what a better sexual match they are for you than your ex was. You could get your ass on OkCupid or Tinder and find a hookup for the night, and use that stranger-wang/stranger-tang to exorcise your break-up demons. You could finally ask out that cute friend of yours for whom you’ve had the hots for ages. You could sign up for a cam site and jerk off for horny randos (this is especially effective if your ex would have hated you doing this).

We all move on from break-ups at different paces. If you – like me until recently – have been stuck in a dry spell since your relationship ended, it might be enormously healing for you to get back out there and get laid. It’s kind of one of those “you won’t learn to swim until someone pushes you into the pool” situations, except you have to be the person to push yourself into that pool. The confidence you gain from even one decent fuck will help propel you forward into more. Break-ups can decimate your self-image, but there are ways to deal with that, and sex is a fabulous one.

Dream up an ideal partner.

Grab a big sheet of paper. At the top, write a phrase that stirs romantic feelings in your heart, like “DREAM LOVER” or “MR. SO SO RIGHT” or “BANG-BUDDY EXTRAORDINAIRE.”

Then make a list of all the qualities that matter to you in a partner. They can be physical, mental, emotional. They can be hobbies and activities that person would love, interests they’d have, goals and ambitions that’d be on their bucket list. You can refer to pieces of celebrities and exes you particularly like: “Jack Black’s sense of humor,” “Emma Stone’s smile,” “high school girlfriend’s confidence,” “college boyfriend’s nerdiness.” If you’re artistically inclined, you can draw or collage some imagery into this spread, to amp up the lovey feelings you get when you look at it.

Now look over your whole page and let the feelings well up in you. Imagine how it would actually feel to meet that person, to flirt with them, kiss them, fuck them, hold their hand in public, laugh hysterically with them, cry on their shoulder, fall asleep in their arms. Let those images feel real and seem attainable – because they are attainable and they will be real, my love.

Whether you believe this type of visualization makes magic or just feels good, the fact remains: you need to convince yourself of your inherent value, and of your ability to attract better and better relationships into your life. I think visualizing your dream partner would be an amaaaazing way to cap off a breakupiversary party, because it would set your sights on the future – right where you oughta be looking.

 

Have you ever celebrated or commemorated the anniversary of a break-up? How did you do it?

5 Non-Boring Answers to “What’s Up?” When Nothing is Up

We’ve all been there. You get together with a friend who you haven’t seen in a little while, and they ask you, “So what’s up?” or, “What’s going on in your life?” or, “What have you been up to lately?” And your mind goes totally blank.

It’s not that your life is boring, but maybe there just hasn’t been a lot of drama lately. Everything’s kind of stayed the same. Nothing new to report.

Of course, the whole reason your friend asked you that question in the first place – aside from genuinely wanting to know how your life is going – is that they wanted to spark a conversation, and those standard questions are an easy way to do it.

So, with that in mind, here are five ways you can answer that question if you don’t have a “real” answer. Let me know how they work for you!

 

1. “Right now I’m obsessed with…”

In my journal-writing, I often talk about things that feel “emotionally significant” to me at the moment even if they’re not significant to my life in a tangible, physical sense.

You might be binge-watching a show on Netflix, fanatically following a particular news story, or ploughing through a delightful novel. You might have seen a rad YouTube video you want to ramble about, or maybe you just learned to cook a new meal and now you want to make it every damn day.

Whatever you’re fixated on at the moment, you don’t need to hide it away and look for something “more interesting” to talk about. Your friend is your friend for a reason. They’ll probably find your obsession charming. Or at least it’ll get a conversation started.

 

2. “Sometime soon, I’d like to…”

If nothing riveting is happening in your present, you can always talk about what’s gonna happen in your future.

For example, lately when friends ask me what I’m doing, my answer tends to include, “I think I might go on a trip to Newfoundland next year!” There’s nothing concrete about that, but it’s okay, because my friends still tend to find it interesting and it leads us into a conversation about travel, saving up, future plans, et cetera. That type of conversation is always exciting, even if none of our plans have officially been made yet!

 

3. “I was just thinking about that time that we…”

Just as projecting into your future can prompt fun conversations, so can reaching back into your past.

This can be especially enlightening with friends you’ve known for a long time. By talking about experiences you’ve shared, you strengthen your bond, and you can also reflect on how far both of you have come.

I have one friend who loves this type of conversation and approaches each one very thoughtfully. Some questions we’ll often ask each other as we talk about our past are, “What do you think you learned from that?” and “If you could do that over again, what would you do differently?” You can learn so much about your friend – and yourself! – by contemplating these questions together!

 

4. “This might seem small, but…”

If you haven’t got any “big” life updates to share, it’s perfectly fine to rattle off some small ones. You never know where you might find some common ground with a friend. They might have some advice for you, or they might be going through something similar.

Maybe you just installed a new TV in your house… or your ex-girlfriend posted something questionable on Facebook… or you ran into a former teacher. Whatever. It doesn’t need to be earthshattering. Your friend is your friend because, at least in part, they find you entertaining and pleasant – including your more mundane tales.

 

5. “Not much! So I think I need to…”

If you routinely find it difficult to answer when a friend asks you what’s going on, maybe that’s because you’re in a bit of a rut.

It’s totally okay to be happy with the status quo, but if you’re finding that you want to make some changes, maybe you can tell a friend that and see what suggestions they have for you.

If your job bores the fuck out of you, maybe it’s time to look for a new one. If your relationship feels stagnant, maybe you need to re-ignite it or call the whole thing off. If you’re feeling unchallenged across the board, maybe it’s time to learn a new skill or force yourself to try something new.

Your friend may be able to see a blind spot or destructive pattern that’s preventing you from moving forward, which is why it’s useful to have this type of conversation with a friend instead of just mulling it over inside your head.

 

I’m curious: how do you answer the “What’s going on in your life?” question if you don’t have much to say?

10 Reasons Why Sex-Positive Friendship is Important

L to R: Reenie, Aerie, Bex, Penny, Kate, Epiphora, GJ
L to R: Reenie, Aerie, Bex, Penny, Kate, Epiphora, me!

 

#DildoHoliday is decidedly over, and dildrop is real.

I miss the beautiful house we stayed in. I miss the delicious group meals. I miss the mid-day masturbation breaks.

But mostly, I miss my friends.

When my dad was driving me to the airport to depart for Portland, he asked me, “Won’t it be weird to stay in a house with strangers?” but that’s not how I felt at all. These people weren’t strangers; I’d been corresponding with them on Twitter and other mediums for years. I already knew them better than I know most of the acquaintances I regularly see at home in Toronto: the guy who owns my favorite café, the distant classmates in some of my courses, the boys in my brother’s rock band.

I have sex-positive friends “in real life” as well, but #DildoHoliday really showed me just how important it is to have friends who are on the same page as you in as many ways as possible. There’s comfort and strength in that, for all of us, I think. Here are 10 reasons why sex-positive friendship is so valuable and crucial…

1. There’s no sexual shame. With my deeply sex-positive friends, I can talk about my kinks – even the ones I consider weird, taboo, or potentially unethical – and there’s no shame associated with it, from me or from my friends. If someone mentions fantasizing about exhibitionism or incest or watersports, no one even bats an eye. The most reaction you might get is something like, “Cool! Sounds fun!” or “Interesting! How’d you get into that?”

2. There’s no body shame, either. Body-positivity and sex-positivity are two different concepts with two different communities, but there’s a lot of overlap; most of my friends in each category also fall into the other. Being a chubby lady, I sometimes feel weird about getting naked (or even just exposing “problem areas” of my body) around people who I think might judge me; that’s not an issue with my body-positive pals. I can also eat what I want without worrying about how my food choices are being perceived. And in seeing all the carefree, happy body acceptance exhibited by my friends, I can get a little closer to that goal myself.

3. We don’t have to explain ourselves. Yeah, I own a lot of sex toys. Yeah, I sometimes post nudes on the internet. Yeah, I’m ideally looking for a kinky, non-monogamous person to be my next beau. There’s nothing wrong with any of that, and my sex-positive friends understand that without having to be convinced. Likewise, I accept their kinks and quirks, because that’s what “sex-positive” means: everything is A-OK as long as it’s safe, sane and consensual.

4. We don’t have to provide basic education. Look, I’m all for making the world a better place by teaching folks about sex, but I don’t want to do it all the time. It takes a lot of energy to explain, for example, why penetrative orgasms are an unreasonable goal for most vagina-havers, why a particular advertisement is sexist or racist, or what it means to be a sex toy reviewer. It’s nice to be around people who’ve taken the time to educate themselves and who therefore understand me without requiring me to explain what I consider basic-level concepts.

5. We nerd out about the same stuff. We refer to Tristan by her first name only, because we all know who she is and what she does. We get enthused about new sex toys on the market and discuss ‘em with wild abandon. Making our own glass dildos sounds 100% fun and 0% weird. (More about that in a future blog post, OF COURSE!) Sharing in each other’s enthusiasms brings us closer and – yes – makes life a ton more fun.

6. We can give each other advice. And not just basic, unhelpful advice that you could find on Google or Yahoo Answers – high-level advice tailored to the person asking. If I’m on the hunt for a new sex toy and I ask an in-the-know friend, she can suggest a toy that’s not only good but good for me specifically. Or I can ask a friend how to approach a difficult sexual conversation, knowing that she’ll keep my anxiety issues in mind when she answers. Or I can help my friend craft a tricky email to a sex toy retailer, knowing exactly what’s at stake and why she’s struggling with it. The better you know your friends and the worlds they’re a part of, the better equipped you are to help them navigate those worlds.

7. We can be sexual around each other without it getting weird. I once had sex with my then-FWB while my best friend photographed us. I’ve masturbated in front of friends, and watched them do the same. I’ve told friends explicit stories about sex and masturbation, and listened to theirs. I’ve watched porn with friends, groaned at the hottest parts, and talked in detail about how our vaginas were reacting to the scenes’ events. When you do this stuff with sex-positive pals, it tends to feel like a natural extension of your friendship instead of like some strange, stilted step into another realm. Sexual pleasure is a massive source of joy and I see no reason to fence it into my romantic relationships exclusively.

8. We get excited about each other’s sexy adventures. I still remember the time I texted a friend to tell her I’d given my first-ever blowjob and she responded by telling me she didn’t want to hear about stuff like that. It hurt to have a friend snub me about something I considered thrilling and momentous. With my present-day sex-positive friends, that kind of thing would never happen. My family and casual pals may not applaud me when I manage to insert a large dildo for the first time or gasp in delight when I tell them I met my favorite porn star, but my sex-positive friends do – because they get it.

9. We complain and commiserate for the greater good. My friends understand that it’s gross when some dude silently favorites all my selfies, that mansplainers are the scum of the earth, and that weak vibrators make clits sad. When we complain together about stuff like this, we can make it into a joke, something to laugh at, so it becomes more palatable and easier to tolerate. We may not be able to rid the world of douchebros and shitty toys, but we can laugh our asses off about them, which is almost as good.

10. We help each other expand and explore. I would never have gotten naked on camera if I didn’t have friends who shoot porn and nudes, but I’ve loved doing it and it’s helped me evolve as a sexual person. I would have taken much longer to end my last relationship, even though it was clearly dead, if my friends hadn’t encouraged me to go through with it. One of my most treasured memories from #DildoHoliday is a round-table discussion we had where we all shared what we’d like to see each other blog about. When your friends are living sex-positive lives, they can help you see how to live that way too, in bigger and better ways every day. And that’s a very good thing.

What do you appreciate most about your sex-positive amigos?

How to Date When You Have Anxiety

“You should write a blog post about how to date when you’re an anxious person!” my friend said excitedly, as we gossiped about boys (and mental health struggles) over lattes and cupcakes.

“HAAHAHAHAHAhahahaha,” I replied. “I have no idea how to deal with my anxiety while dating. I barely even manage it myself. How can I tell other people how to do it?”

The more that I thought about this exchange, though, the more I wondered if I could actually be more helpful than I’d realized. I don’t think you have to be an expert in order to help someone. The experiences you’ve had, and the lessons you’ve learned, can be of use to others even if you’re still in the midst of your own journey.

So, with that in mind, here are some things I’ve learned about navigating the dating world when your brain’s fear-meter is a little out of whack. I hope this helps you, at least a little.

1. Enlist socially competent friends.

It feels a little “high school” to constantly text friends whenever anything happens with your crush, I know. But if you’re lucky enough, as I am, to have friends who appreciate (or at least tolerate) this behavior instead of blocking your number, I think you should let those friends support you and help you.

Here are some examples of ways my more socially skilled friends have saved my ass when anxiety was clouding my brain:

• I texted my pal E., “[Boy] said he might want to see a movie with me today, but now I feel like it would be too forward for me to text him and ask him about it!” E. reminded me, “[Boy] said he wanted to see a movie with you, so it’s not forward,” and then suggested a possible wording for the text I could send. What an angel.

• I spoke to a number of friends about the situation with a boy I liked, and several of them said, “Go for it!” I wasn’t really sure what this meant, precisely. I asked my friend E. what he meant when he said “Go for it” and he said, “Tell him you like him, or ask him out.” Ahhh, okay, I thought. The specificity helped.

• While chatting with my friend A., I listed a bunch of things that [Boy] had said and done the last time we hung out, all of which I thought were ambiguous and could have been flirty or just friendly; I really didn’t know. When I finished, A. laughed for a good minute and said, very sarcastically, “Yeah, he’s totally just into you as a friend.” Her third-party viewpoint helped me see what my anxiety had been hiding from me.

• Soon before my last break-up, I realized I didn’t actually know how to break up with someone. People kept telling me, “Just get it over with!” and “Be respectful but firm!” but I was missing basic information like where to do it and what to actually say. My pal A. helped me rehearse a little script and weighed the pros and cons of various break-up locations with me. We even discussed what to wear to a break-up, because that’s the kind of thing I worry about.

See? Friends can be sooooo helpful when your brain is being your worst enemy.

2. Journal about it.

Where would I be without journaling? Maybe dead. Definitely sad and confused.

I find journaling absolutely essential as an anxious person because it helps me process all my zillions of thoughts. I can go on a 5-page-long ramble about all the worries and insecurities I have around a particular situation, and by the end of it, a) those thoughts no longer occupy my brain quite so firmly, and b) I can see very clearly just how ridiculous those thoughts are. Journaling gives me some distance, some objectivity.

I can also tell you from firsthand experience that it is hilarious to re-read your old journal entries from the nervous beginnings of relationships. “You silly twit,” you’ll shout at your past self, “of COURSE he meant he liked you when he said ‘I like you’!!”

3. It’s okay to be honest.

Sometimes when I start dating someone, or even when dating seems possibly imminent, I’ll bust out a little speech. It goes something like this:

“Hey, so, just so you know, I have anxiety. That means that sometimes I’ll get really nervous around you and act weird. It doesn’t mean I feel uncomfortable or unsafe with you; it’s just how my brain works. I also might need a little extra reassurance and validation from you sometimes, because my anxiety is always telling me that people don’t like me and that I’m worthless. So if you could try to assure me once in a while that you actually do like me, that would be really helpful. I’ll try not to be too weird.”

People tend to respond favorably to this kind of honesty, actually. Some people even find it adorable. (That’s a whole other can of worms – my mental health issue is not cute, okay?! – but it’s certainly better than them shaming me for my anxiety or dumping me because of it.)

4. Find your self-care practices and use them.

Here are some things I like to do when I’m getting ready to go on a date or to spend time with someone I like:

• Spend ages choosing the ideal outfit, doing my makeup and hair, and making sure I look adorable. (Some would call this obsessive, maybe, but it helps me calm down.)

• Make sure I know, with 100% certainty, where we are going, how much it’s going to cost, what time I have to leave my house in order to get there on time, and any other relevant information. (I eliminate all possible stressors. This is an act of self-love and self-protection.)

• Play Scrabble on my phone while traveling to the destination. (It calms my brain somewhat, by giving me something to focus on besides my stomach-curdling fear. Podcasts and music also help.)

• Breathe deeply and slowly. (“Fear is just excitement without breath,” after all.)

Whatever your own self-care and self-calming practices are, make sure you actually remember to do them when you need to. It might be helpful to write them on a card and keep them in your wallet, or set them as your phone background, or whatever. Keep ’em close and do ’em often.

5. Assess the situation objectively.

As objectively as you can, anyway. I know it’s difficult.

If you find yourself thinking an anxious thought – for example, “He doesn’t like me anymore!” – look for evidence of that thought. Odds are, there won’t be as much as you thought (or any).

Then look for evidence of the opposite thought (e.g. “He likes me a lot!”). There will probably be some.

Breathe. It’s okay. Your fear is inside your own head and nowhere else. You don’t have to listen to it. It doesn’t reflect reality.

Anxious folks: how do YOU navigate the dating world without vomiting on your suitors’ shoes?