casual sex

23 Things I Learned About Sex & Relationships At Age 23

Kate Sloan

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Today’s my 24th birthday! It’s a good day to reflect on the past year, because I think 23 was my most transformative and educational year yet. I banged and dated a bunch of different people, and it was essentially a crash course in emotional maturity and sexual confidence. Here are 23 of the most valuable lessons I learned about sex and relationships over the past year!

  1. I have a DD/lg kink. I first noticed these feelings back in late 2014 when a hot lawyer inspired some surprising fantasies in my bad little brain. In November I started seeing a dude who was muuuch kinkier and more kink-experienced than me, and when I disclosed to him that I had burgeoning DD/lg fantasies, he knew exactly what to do with that information. I still vividly remember the time I sassily asked him why I should follow his instruction to jerk off for him and he said, “Because you’re a good little girl.” It was the first time anyone had ever said anything like that to me before, and my vagina did cartwheels.
  2. Terrible mental health days are terrible kink days. At least, for me. If I’m already feeling extremely shaky, anxious, or depressed, kink tends to just worsen my mood. I learned my lesson from the time in January when an intense spanking on an already-anxious day made me burst into tears and sob deeply for several minutes while my confused partner tried to comfort me.
  3. …but, kink can help with mental health. Paradoxical, yes – but for me, there’s a fine and important line between “too distraught to submit” and “just distraught enough that submitting will actually help.” Pain, punishment and praise can help shake me out of a poor mental health day, used judiciously with a trusted partner.
  4. I can have casual sex… with people I don’t really like. Sex tends to open up my emotional floodgates, intensifying any burgeoning crush-y feels that already exist there. I was able to have some casual, feels-free fuckbuddies this year, but only because we didn’t click romantically. This is useful info for me to know going forward, though it does mean I’m incapable of being “chill” with anyone I even remotely like.
  5. I like pain (in some places). I’ve dabbled in spanking over the years, but it wasn’t until age 23 that I really grasped how much pleasure I can get from pain. Getting my tits and/or ass slapped has become one of my favorite foreplay activities. I even like getting my hair pulled, a proclivity that used to mystify me.
  6. I love giving blowjobs. HOO BOY, this was a big theme of my year. My previous blowjob experience encompassed only one partner, and while he was lovely, his dick and my mouth just didn’t have chemistry. In broadening my BJ horizons, I’ve discovered how much I can crave having a cock in my mouth when the right one comes along. (I’ve gotten pretty damn good at it, too.)
  7. I’m more of a size queen than I thought. Remember when I first started this blog and dildos over 1.5″ in diameter were a stretch for me? That is certainly not the case anymore… Just ask my Eleven, Double Trouble, and Seaside Steamroller!
  8. I need to trust my intuition more. My anxiety is excellent at talking me out of what I know, deep down, to be true. When I let myself listen to my hunches, I can usually tell when someone is flirting with me, likes me, or wants to get in my pants – and it happens more often than my anxiety wants me to realize.
  9. Aftercare is important. Coming from a pretty vanilla history, I never thought much about the importance of aftercare until I really needed it. Fortunately, all my kinky partners this past year (and even the vanilla ones) gave me the post-sex cuddles and reassurances I needed.
  10. Most men like thigh-high socks. They just do.
  11. Sex is grown-up playtime. My favorite sex is the goofy, unstructured kind. I love trying stuff, experimenting, playing around. I’m happiest in sexual partnerships with people who are similarly fun-oriented, rather than goal-oriented.
  12. I like being pinned down. Have you ever had a moment where, suddenly and all at once, you noticed a kink of yours that you never knew you had? That was me last summer when a partner put a firm hand on my upper chest and held me down while finger-fucking me. I went from “huh, that feels pretty good” to “holy shit, I am coming right now!” in about three seconds flat. I’ve been pinned down during sex a bunch of times since then, with similar outcomes. Now that I know I like this, I want to get better at asking for it!
  13. Threesomes are fun, but not really my jam. I’ve gained a reputation among my friends for constantly having threesomes. I’ve only had two, but I guess that’s still more than the average person? In any case, while I enjoyed myself both times, I still prefer the intense, focused connection of a standard one-on-one encounter. (Talk to me in a month, though… I have a rather epic threesome coming up on my calendar that might get me more on board with group sex.)
  14. When you’re sad, sometimes you just gotta feel your feelings. A couple of painful rejections left me in emotional shambles at times this year. I spent a lot of time crying on friends’ shoulders and saying things like, “I’m just so sad! I don’t know what to do!” My friends are fantastic and a lot of the advice they gave me boiled down to this: it’s okay to be sad when sad shit happens. Don’t try to run away from those feelings or distract yourself from them; just live in them for a while. It’s so much easier to move on when you’ve processed your feelings properly.
  15. You can like someone very, very much and they can still be wrong for you. You are not obligated to try to “make things work” with someone who’s a deeply bad match for you. Even if they’re a good person. Even if you adore them in many ways. Even if they don’t understand your reasoning.
  16. Platonic kink is a thing. I learned so much about kink this year, including that it can exist independently of sex. I have friends who fuel me by calling me a “good girl” when I finish my work; I have friends who phone me and speak to me in commanding, daddy-dom tones to calm me down when I’m anxious; I have friends whose kinks I know intimately and (consensually) use to guide them into healthier and happier behaviors. Kink is more than a sexual interest; it can be a psychological tool, a powerful motivator, a framework in which to understand yourself and your place in the world.
  17. Twitter is a great place to meet sexual partners. Half of the new people I banged at age 23 are folks I met on Twitter. Obviously it’s a problematic space and women receive a lot of harassment and abuse through tweets and DMs, but I’ve also built an audience there of clever, compassionate sex nerds, some of whom are pretty great sex partners.
  18. When you like someone, it’s okay to act like you like them. My anxiety makes this tricky, because even the smallest braveries feel like ballsy overtures to me. But I’m working on it. More people should know that they’re cute, and I should tell ’em.
  19. Don’t stake your mood on other people’s behavior. Most of my miserable-est days this year were the result of me believing, “If [person] would just [action], I could be happy right now.” I learned that I need to either change my expectations, or try to make things happen myself; waiting for someone else to read your mind and do what you want them to do is a fool’s errand.
  20. Anxiety-friends are invaluable flirting sherpas. This is no joke: I owe most of my romantic and sexual success this past year to Bex. Any time I didn’t know how to interpret a romantic interest’s flirty behavior, or couldn’t parse a cryptic text, or needed a push in a flirty direction, I went to them for advice. I have other “anxiety-friends,” too, who are willing and able to answer texts like, “[Person] said [thing], are they into me?!” and “What do I wear to a date-that-might-not-be-a-date?!”
  21. I like anal sex. I wasn’t sure how I’d feel about it, because my past adventures with butt plugs and anal beads had been inconsistently pleasurable. But, holy fuck, I was into it and I want to do it more.
  22. I don’t need (or want) monogamy, but I do need to feel special. I don’t mind having partners who have other partners. (Yay, #PolyLyfe and compersion!) But I do need my partners to make me feel valued, seen, and focused on when we spend time together. I received a few propositions this year from folks who date/bang a lot of people, and I learned that that only ever feels okay to me if they clearly like me for me – not because they like dating/banging whoever. I’m definitely not anti-promiscuity and there’s nothing wrong with being slutty! I just need a side order of emotional connection with my sluttiness.
  23. Life is too short for bad sex. I believe there are two main ways to be bad at sex: you can be bad at technical skills (“He kisses like a snake!” “Her fingering rhythm is inconsistent!”), and you can have a bad attitude about sex (“He refused to use toys on me!” “She got all sulky when she couldn’t get me off!”). I’d rather be with an enthusiastic newbie than a mopey pro any day. If you’re fun to bone, I’ll probably gladly teach you how I like to be fucked so you’ll know for next time – but if you’re a sad and draining lay, there probably won’t be a “next time.” I’ve raised my standards enough to say no to bad sex – because, frankly, I’d rather just masturbate.

 

Here’s to another sexy, educational year!

My First Threesome Was a Smash Success

Kate Sloan

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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 Prepare For a Casual Sex Date

Kate Sloan

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!

Why Casual Sex is Brilliant (& Why I Wish I Was Having Some)

Kate Sloan

Because my first sexual relationship was with a friend and not a romantic partner, I’ve been asked plenty of times, “How do you separate love from sex like that?! I could never do that!”

This question used to make me nod thoughtfully and say things like, “Yeah, I can see why it could be difficult,” and “It’s a process, that’s for sure!”

Now, though, I just kinda… laugh. Because love and sex are soooo separate in my mind these days. Ever since my break-up last August, I feel an occasional pang of desire for emotional intimacy, cuddling, romantic dates, and declarations of adoration – but what I crave ceaselessly is sex. With or without love. Whatever. I just want it.

I have yet to have casual sex – my past dalliances with a friend-with-benefits were hardly “casual,” partly because we hung out all the damn time and partly because she was in love with me – but the idea of it glitters in my mind as the solution to countless sexual dilemmas. Here are some reasons why casual sex is a fucking terrific advent…

It’s fast. Truthfully, one of the reasons I ended my last relationship (aside from, y’know, just not feelin’ it anymore) was that I didn’t have the time or energy to invest in a romantic partner like I used to. Having a beau is a massive time commitment: dates, meandering conversations, ongoing negotiations, reassurances when needed, and so on. That stuff can be great when you’re able to put time into it, but when you’re not, casual sex is the better way to get your libidinal needs met.

It’s easy. At least, compared to wading through the sea of romantic options to find That One Person you click with on all the levels that matter in a relationship. Most people’s criteria for a casual sex partner are basically “Am I attracted to this person?” and “Can I stand to be around this person for short stretches of time?” Those requirements are pretty easy to meet. And the internet has made this process even simpler, by providing us with services like mysexhookups.com so we can get to the good stuff ASAP with minimal wasted time.

It’s shameless. Well… relatively. We all have some sexual shame to work through, because of our bullshit sex-negative culture. But I’d imagine it’s a lot easier to cop to your kinks when you know you’ll never see the person again. A long-term partner yucking your yum is a lot tougher to take; with a casual partner, if an incompatibility becomes clear, you can just say, “See ya! Onto the next.” And if they do share your kink? Then you’re probably in for some stellar sex.

Are you a casual sex devotee? Any tips for someone who’s new to this world (and kinda, maybe, extremely shy)?

This post was made possible by the folks at mysexhookups.com. Kisses!

My Big, Exciting, Scary, Sexy Goals for 2015

Kate Sloan

The new year is upon us! I hope you had a fun New Year’s Eve last night, and that you woke up this morning feeling refreshed and renewed, as opposed to hungover and grumbling!

Come the new year, a lot of people set resolutions for themselves. I think self-improvement is always a good use of time, but something about the vagueness of resolutions just doesn’t work for my brain. I like to set GOALS: specific, actionable tasks or projects whose completion will be immediately and entirely clear to me when it happens.

Here are some of the sex-related goals I’ve set for myself this year… Hopefully, a year from today, they’ll all be checked off my list!

1. Have casual sex.

For a sex blogger, my sexual history sure isn’t very adventurous. I’ve only ever had sex with two people: one a long-term friend with benefits and the other a long-term boyfriend.

Right now I’m too damn busy to get into another relationship so soon after ending the last one, plus I’m just not feelin’ the whole commitment/obligation thing right now. I’d rather be free and clear, at least until I find myself so head-over-heels for someone that coupledom looks more attractive than the alternative.

But although I’m relationship-phobic at the moment, I’m certainly not sex-phobic. In fact, it kind of feels like a part of me has shrivelled up and died from how long I’ve gone without sex at this point. (About eight months, I think? Shh, don’t tell anyone!!)

So one of my goals for the year is to figure out how to have casual sex in a way that feels safe, healthy and positive for me, and then do it. I’m defining “casual sex” as “sex with someone I am not, and do not intend to be, in a romantic relationship with.” I am super shy and awkward and don’t even know that many people I’d want to have sex with, so we’ll see how this goes…

(Last night I was having dinner with some friends and we got onto the topic of 2015 goals. I mentioned that this was one of mine, and one of my friends said, “Do you have a particular gender in mind for the person you want to have sex with?” I shrugged and said, “I just need to find them hot. That’s the only criteria.”)

2. Learn to get off in several different positions.

98% of the orgasms I’ve ever had in my life have happened while I was lying on my back with my legs slightly raised. It’s how I initially learned to get off so it’s always worked for me. But it can be inconvenient sometimes.

I’ve managed to come while sitting up (like on a chair while a partner kneels in front of me – oh swoon, I miss that, it was hot) and while sitting on someone’s face (definitely a lot easier if I can lean my weight on something, like the headboard of the bed) but it’s usually a lot of extra effort for me. So I’d like to practice getting off in various different positions until it starts to feel easier and more natural.

(Side note: I was inspired to take on this goal after going to see Canadian playwright Morris Panych’s latest play Sextet a few weeks ago. There is a character whose legs need to be above his penis – like, propped up on a wall – for him to reach orgasm. I won’t spoil it for you, but… comedy ensues. And it made me realize just how silly it is to limit myself to only one position!)

3. Get spanked.

This is one of those wishes I have to kind of release to the universe instead of trying to figure out how to make it happen. I don’t currently have any idea who I want to spank me or how I intend to get into a situation where this can take place. I just know that I want it, somehow, somewhere, some way.

I’ve done a fair bit of spanking play in previous relationships but now I want to try it with someone new. (Oh man. I got sexy chills just typing that.)

Interestingly, spanking also played a role in one of my 2013 goals, so apparently it’s something in which I have a keen interest…

4. Two big blog announcements.

Because I’m the queen of mystery (ha), I’m not going to tell you what they are… yet. But I have two big things planned for this blog in 2015. Both will require a lot of work and preparation, but it’s work that I am very excited about, which is the best kind!

What are your goals for 2015, sex-themed or otherwise? Got any tips for me as I pursue mine?