A Casual Love Letter to My Casual Lovers

I don’t love you, I’m certainly not in love with you, but we approach our time together with fondness, care, and – yes – love.

When I ask you to touch me a certain way, you do it – which is no small thing. When I want you to touch me a certain way, I feel comfortable asking for it – which is no small thing.

When someone else breaks my heart, it isn’t your responsibility to put it back together. But sometimes you do, a little bit. Maybe without even knowing that’s what you’re doing. Sometimes your touch heals me and it’s always a surprise, because it’s never something I expect to want or expect to get.

When my body feels broken and ugly and wrong, you remind me that it isn’t. You play me like a xylophone until we both can hear my nerve endings sing. I feel whole and gorgeous under your hands.

Beaten down by love’s little twists, I sink into the fiction that maybe no one will ever want me again and maybe I’ll deserve that. You break the spell and show me what I always know is the real truth: that I am wanted and wantable, loved and loveable.

You are both training ground and sacred soil. I try out new tricks without shame because the stakes are low and the payoff is high. I find my footing in your company. When I fuck up, you laugh, but with mirth and not malice.

Without the tangles of dashed hopes and unmet expectations hanging like cobwebs, I’m free to enjoy pleasure without heartache. I pull you closer without fearing I’ll scare you away. I hold on tight while we’re together, softening my heart and soaking you up, and when we’re apart I let you go. No effort, no struggle. It’s practically Zen.

For days or weeks, we forget each other, wrapped up in our respective adventures. And then a text or two. “I saw something that reminded me of you…” “Remember that time when we…” “I hope to see you again soon.”

You’re like a lucid dream within my waking world. A quiet burst of glee untethered to anything else I know. We show up, make each other laugh, make each other come, and part ways. An equable bargain, a cloudless reverie.

On the streetcar ride home from the sex club, I sit all chlorine-damp and fuck-drunk, smiling like the luckiest girl in the world. Because every time I see you, I am.

The 10 Commandments of Successful Friendships-with-Benefits

My first-ever sexual relationship was a friendship-with-benefits. So you would think I’d be better at that type of arrangement than the average person, since FWBs have been part of my sexual menu for literally my entire sexual career.

Nah, man. I wish. I have fucked up FWB situations in all manner of ways: I’ve fallen in love with fuckpals or turned the other cheek when they fell for me; I’ve undervalued them, or else heaped all my sexpectations onto them; I’ve ended things unceremoniously or not at all.

These are easy mistakes to make, because we don’t have clear social scripts for how FWB relationships (or, as I sometimes like to call them, “copulationships”) are supposed to go. However, these days, I have a rotating roster of occasional fuckbuddies, all of whom I adore – so I’m feeling much more motivated to do things right. Here are ten guidelines I think will serve you very well in copulationships of your own…

Only do it if you both want to. You’d think this would be obvious, but it isn’t always! Sometimes, people agree to a friendship-with-benefits because they think they have to. Maybe they want a romantic relationship with the other person, and think being their FWB is the closest thing they can get. Maybe they like their friend as a friend, and don’t quite know how to turn down the offer of sex without also severing the friendship. Maybe they’re just not a casual-sex type of person, but feel a social or societal obligation to pursue it anyway.

Before entering a FWB situation – or while the formation of a new one is still recent – give some thought to your reasons for wanting it, or not wanting it. Ask your pal how they feel about the situation as well. As in all things sexual, you cannot overprioritize clear, ongoing, informed, enthusiastic consent!

Set clear boundaries and expectations. You might think everyone shares your exact definition of “friend with benefits,” but they don’t! It’s important to hammer out what each of you expects from the other, and from the friendship in general. Emotional support? Seeing each other weekly or monthly? Are you seeing other people, and if so, are you going to tell each other when you do? Are certain sexual acts off the table, because they feel too intimate for a casual relationship, or for some other reason? If you run in the same social groups, are you okay with people knowing the two of you are sleeping together, or would you rather keep it on the down-low?

All of these factors can complicate a FWB sitch, so it’s best to figure them out before they become a problem. If there’s anything you’re not sure about, ask. Better to risk seeming a little uncool and find out what’s up, I say.

Ask for what you want – and encourage them to do the same. One of the best things about casual sexual relationships is that the stakes are lower, so you might find it easier to be frank about your desires. If they’re fucking you, presumably they want you to have fun and feel good – so ask for the specific things that would accomplish that! This could be anything from a small adjustment in technique to “Wanna put this huge dildo in my ass?”

As always, be prepared to accept a “No” if that’s their answer, and try not to take it personally. Likewise, you should encourage them to open up about what they’d like you to do – it’s important to be a good sexual partner, even if the situation is casual!

Talk about any feelings that come up. Learn from my mistakes: if you develop romantic feelings for your FWB, it feels like the best thing to do is hide that fact from them. But everything will just get worse over time, and then you’ll have massive emotional chaos on your hands instead of a small blip of a crush that could’ve been nipped in the bud.

Personally, I think that if either party begins to have romantic feelings for the other, it’s best to take a break from sex – and maybe even from seeing each other – until that situation is handled. That can feel difficult bordering on impossible, but trust me: it’s better than full-on falling for your fuckbuddy. You do not want that. It is a mess. Communicate and come up with a solution before you get to that stage, if at all possible.

(Pro tip: this was a chronic problem for me until I met my current main FWB, who is emotionally monogamous to his primary partner and who is also just not the type of person I’d want to date, personality-wise. It can be difficult to find someone who you find sexually attractive, enjoy spending time around, and have no romantic desire for whatsoever, but trust me, it is possible. If I, a severely crush-prone sap, could do it, I believe almost anyone can.)

Keep putting in the effort. It’s easy to feel like you don’t have to try to “impress” your FWB, because they’re not a romantic partner. But that’s a bullshit attitude. They’re your friend, and they’re sharing a sexual experience with you. They’re worthy of your respect and good treatment. If you don’t think so, why are you sleeping with them?

Make sure your sheets are clean when they come over. Shower and groom yourself appropriately. Don’t rush them out the door when you’re done. Treat them like a hot date you’re trying to impress, even if they’re the goofy pal you’ve seen laugh beer out their nose a dozen times. Be worthy of the experiences you’re sharing; they may be casual, but they’re not worthless.

Value their mind, not just their body. If you’re both cool with an “wham-bam-thank-you-fam” arrangement, that’s a different matter. But at that point, they become less a friend-with-benefits and more just a booty call. Keep up with their life, their hopes and dreams, their ups and downs, if they seem to want to share that stuff with you. A solid friendship will make the sex better, too!

Be respectful and polite. Don’t be late to your meetups if you can avoid it. Don’t cancel plans at the last minute unless you absolutely have to. Answer their texts in a timely manner when you can. You know, like… a good friend?

Be a friend, even when times are tough. I’ll never forget the time my FWB came over a week after I’d gotten dumped, and told me, “I’m sorry you’ve had such a rough week. You don’t deserve that. If you just wanna cuddle and talk tonight, I’d be totally fine with that. I don’t want to rush you or pressure you into anything you don’t feel like doing.” Admittedly, I wanted him to fuck me, too – but that was partly because he’d shown his true colors as a genuinely good guy! With this simple speech, he proved he viewed me as a person, not just a series of holes to fuck.

It can be awkward to try to emotionally support someone who you usually only see naked, sweaty, and grunting – but it’s nice to offer. They might not take you up on it, but they’ll probably feel better about the copulationship knowing it’s with someone who has their back.

Cultivate compersion. Incase you haven’t heard, compersion is the term the polyamorous community uses to describe the opposite of jealousy: it’s the feeling of being happy for a partner’s romantic and/or sexual happiness with other people.

Assuming your friendship-with-benefits isn’t monogamous (and most aren’t!), your fuckpal will probably date and/or bang other people while seeing you. They may even end things with you to pursue something with someone else. While this can be painful, it’s also an opportunity for you to hone your compersion skills. I have even found FWB situations to be excellent practice for navigating jealousy in my serious romantic relationships. It’s a win-win!

If it’s over, say so. Don’t ghost or fade away; it’s weak and rude. If you’ve been fucking someone consistently for a while, you owe them an explanation if that has to stop. End it like you’d endeavor to end a romantic relationship: politely, compassionately, and definitively. Don’t leave them wondering why you keep canceling plans or won’t answer their texts; you’re better than that.

Have you had successful friendships-with-benefits? To what did you owe their success?

How to Prepare For a Casual Sex Date

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

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

 

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Physically…

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

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

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

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

 

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Mentally…

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

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

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

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

 

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Verbally…

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

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

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

 

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

 

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

Things I Learned From My Friend With Benefits

When I was fifteen years old, I came out as bisexual. A lot of shit went down – I came out on Facebook, I got hit on by random queer schoolmates who came out of the woodwork, I had my first girlfriend (NBD, we only dated for a month), I attended my first Pride Parade… but maybe the most interesting thing that happened was that my female friend fell in love with me.

She was actually in love with me before we really became friends. She watched from afar, using social media and secondhand gossip as her telescope – and then we started talking, and then we became close. And then, eventually, we began a sexual relationship that would last a year and a half.

I’m not going to lie to you: it was weird. She loved me; I had no feelings for her beyond a friendly fondness. She worshipped my body; I thought she was kinda cute. She put her heart and soul into making love to me; I enjoyed our regular fucks. There’s a lot about that relationship that makes me feel kind of shitty in retrospect, but all the same, I’m very glad it happened, because it taught me most of what I know about the practical applications of sex.

1. Communication is hard. I grew up listening to Sex is Fun and Open Source Sex, so I knew how important it is to communicate with your sexual partner… but I guess I never realized how embarrassing and vulnerable it can be, until I actually had to do it. Even knowing that my partner was deadset on me and wouldn’t leave no matter what I said or did, it was still difficult for me to form basic sentences like “Could you lick a little harder?” Now, I have a lot more respect and understanding for people who get nervous about asking for what they want. There’s still no excuse for not stepping up to that responsibility, but I get it: it’s tough.

2. I love cunnilingus. Really, I do. It’s perfect and beautiful. It’s intimate and hot. It’s smooth and wet and tangy. It can be about dominance or submission or neither or both. I used to watch cunnilingus porn exclusively, thinking maybe my obsession would get diluted a little when I started having Real-Life Sex, and it did, a bit, but not really.

3. Sexual equality doesn’t always appear equal. This girl, she loved giving head. She could literally orgasm just from going down on me. She was way more of a giver than a receiver – and as I’m more on the receiver side of the spectrum, this worked for us. But at the same time, our friends viewed our connection from the outside and worried that we weren’t practicing equality. I see why they would wonder about that, but what they didn’t understand was that sexual equality isn’t about making sure each person gets the exact same treatment – it means making sure that each person gets exactly the same amount of what they really want. And we had that.

4. I love my body. If there’s one thing that can quell adolescent body image problems, it’s an adamant lover. Having someone obsess over the parts of you that you hate the most is indescribably wonderful. I frequently suffered spells of emotion when my lady-lover would say things like, “Please don’t talk about losing weight. You’re perfect the way you are.” Sometimes I think I’d still be insecure today, if not for that fateful tryst.

5. Friends-with-benefits situations can work… if handled properly. We always talked about our feelings. We always confessed if we were feeling jealous or smothered or neglected. We always told each other “where we were at,” even when that was scary or potentially hurtful. And we made our decisions accordingly, like when to take a break from each other, when to spend more time together, who to tell about us and who to keep in the dark. As a result, we both felt heard and respected, even if that sometimes meant getting our feelings bruised a little. I think that’s why we lasted so long.

6. Lesbian sex is great. Yup, the rumours are true – girly bodies, brought together in sexual union, are hot. But the thing is, good sex is good sex, regardless of gender. I learned that later, when I dated a guy. If your partner is enthusiastic, communicative, adventurous, and kind, the sex will be good, no matter who has what anatomy.

I learned so much from my teenage FWB. How to talk about sex, how to negotiate boundaries, how to enjoy my body with someone else’s. So even though our relationship ended on a sour note, I wouldn’t take it back – it formed the basis of all the awesome sex I’m having nowadays and will have for the rest of my days.