Sex With an Ex: Good Idea, or Worst Idea?

I’ve never had sex with an ex. This experience seems to be common, and being as sentimental and stubborn as I am, it seems like something I would do – but I never really have. Apart from one ill-advised encounter with an ex-FWB in a sweaty closet at a Pride party, I’ve never gone back to once again fuck someone I had previously decided I wasn’t going to fuck anymore.

Oh, I’ve certainly thought about it. Whenever someone dumps me, I walk around in a haze of regret for at least a few weeks, daydreaming about running into my ex in public while looking absolutely scintillating, and earning an invitation back to their place for comfortingly familiar sex that will inevitably lead us back into a comfortingly familiar relationship. But this never happens, and in the long run, I never really want it to.

Having sex with your ex is playing with fire. If you broke up, there was always a reason – and if you feel the desire to find ’em and fuck ’em again, it’s worth pondering: what was the reason you broke up, and is that reason still relevant?

It may not be. For example, I’ve broken up with people because I was in love with someone else and it was messing up my relationship, or because they were dating someone who decided they didn’t want to be polyamorous. Both of these are circumstantial roadblocks: they posed a problem at the time but may well have melted away in the intervening months or years. These are people with whom I might be tempted to rekindle things if I ever bumped into them on the subway or at a party, because – why not? If the attraction and compatibility are still there but the problems aren’t, what’s stopping us from giving it another go?

But that’s not why most breakups happen. Most breakups happen because you came up against some kind of fundamental incompatibility, or there was a big betrayal, or you just weren’t feelin’ it anymore. In those situations, it’d be tougher to justify a redo. Sure, your ex’s body and mind might still thrill you, or inspire a nostalgic frisson, but pursuing that half-extinguished spark is often more trouble than it’s worth.

Of my 30 lifetime sexual partners, 28 are people I’m no longer sleeping with. Of those 28, 10 are people I would happily fuck again if the opportunity presented itself – but that’s unlikely to happen. 5 are people I would consider fucking again, but we would have to have some heavy discussions and one or both of us would need to make some serious amends before I would feel comfortable jumping back into things with them. The remaining 13 are people I just don’t have any desire to be intimate with ever again – either because they hurt me too badly, or I’ve lost all attraction I once felt for them, or we just aren’t sexually compatible, or all of the above. I’d be curious to know what your ratio is, if you feel like sharing!

So, is sex with an ex a good idea? I think it’s a situation where you’d have to have a lot more pros than cons to justify even attempting it. Sex with someone who knows your body, who you feel comfortable around, and who you don’t have to explain yourself to is very tempting – but I think, in most cases, it’s not worth the complications and tricky feelings it could bring up. Whether I dumped them or they dumped me, I’d be verrrry hesitant to get back in bed with an ex. That’s not to say you should never do it, but be careful with your heart, okay?

 

This post was sponsored. As always, all writing and opinions are my own.

10 Tips For Incredible Kisses

You know, for the amount of kissing I do, I really haven’t written very much about it here! It’s often taken as self-explanatory, which I don’t think is strictly fair. All of us had to learn to kiss, in some sense, even if parts of this act came naturally to us. So here are 10 tips I think are worth considering, whether you’re smooching a new beau or a well-established partner…

1. Take good care of your lips

Boys, especially, often don’t know to do this, or don’t bother. But lip texture matters! If you can’t bring yourself to use a lip exfoliant (Lush makes some, or you can make your own by mixing sugar and honey or coconut oil), just give your wet lips a scrubdown with your also-wet toothbrush next time you brush your teeth. Follow up with a moisturizing lip balm – something natural, containing ingredients like coconut oil or shea butter, will work better than more synthetically-based options.

2. Have mints and/or gum on hand

Keep ’em in your bag or your pocket. Regularly restocking this stash is just as important as keeping your condom reserves topped up. Treat it as such!

3. Get consent

The debate about the necessity of clear consent rages on, especially when it comes to kissing, which often isn’t viewed as “intense enough” to warrant asking for permission. Here’s my stance: nonverbal consent is certainly a thing, and if you’re well-attuned to your partner then you may well be equipped to kiss them out of the blue without incident, but “Can I kiss you?” or “I really wanna kiss you right now” are still hot and cute even when you know for sure you’re gonna get a “yes.” You’re not going to “ruin the moment” by making sure your partner is comfortable and amenable, trust me.

4. Use less tongue than you think you should

So-called French kissing isn’t as mysterious or confusing as it once seemed to me… The trick is to use your tongue as punctuation, not the whole sentence; as seasoning, not the whole meal. As Dan Beirne once wrote: “I would recommend thinking of the kiss as a sleep and your tongue as the dream. It’s not right away, and it doesn’t last the whole time.”

5. Vary your rhythm

Kissing shouldn’t be like a metronome; your speed and intensity should vary according to the needs of the moment. Pay attention to what your partner is doing and how they’re reacting, and mix up your rhythm accordingly. Some moments call for slow sensuality, while others are better suited to fast, hard passion!

6. “Yes, and”

The improv-based practice of “yes-and”-ing is simply the process of paying attention to what your partner is doing, matching it, and adding onto it. To give a more concrete example: if they lick your lip a little, you could lick theirs a little harder. If they pull you closer, you could tilt them into a deeper kiss. If they press their body against yours, you could grind your thigh against their bits. This is not to say that you should only ever follow your partner’s lead – I’m sure you have some great ideas of your own – but launching a new move out of nowhere is often not as effective as simply building upon what’s been done already.

7. Give an oral sex preview

If you’re doing the kind of kissing that you think could lead to sex – whether immediately or eventually – then you can rev up your partner’s arousal by showing them what else your lips and tongue can do. You could, for example, flick your tongue over their lower lip in a cunnilingus-esque manner, or gently suck on it the way you’re going to suck their cock later. They’ll get the message!

8. Convey passion with your hands

Good kisses don’t just involve your lips, but your whole body. This includes your hands, which shouldn’t just be floating there. Provided you have consent for such things, feel free to let them roam over your partner’s hair, neck, shoulders, back, waist, hips, boobs, and/or thighs. This makes your kisses into a bigger, deeper experience than they would be if your mouth was the only body part at play.

9. Use your words

This one may not work so well if you’re super shy – but even if that’s the case, sometimes it’s worthwhile to push through and do it anyway! Try peppering little phrases, confessions, and observations in between your kisses, if it feels right. “Your lips are so soft.” “You taste amazing.” “You’re really good at that.” “I love kissing you.” These sentiments are small but they can make a big difference in your partner’s confidence and comfort.

10. Your thighs can do amazing things

I wax evangelical about “the thigh-grind” in every medium, and this blog is no different… Your thigh is a nice, firm, broad surface that can feel oh-so-good when pressed up against the genitals of someone who wants that. This move is an easy and hot way to turn up the heat during a kiss, and it can be carried out just as well whether you’re in bed, on the floor, in an elevator or in an alley.

What are your favorite tips ‘n’ tricks for kissing?

 

This post was sponsored. As always, all writing and opinions are my own.

Why Sex Skills Are More Important Than “Sex Moves”

Sex guides that focus on particular “moves” have entertained me for years. I read them like they’re porn, and in a way, they are. “Swirl your tongue in circles around the clit.” “Stroke the G-spot firmly with two fingers until you feel it swelling.” “Lick the frenulum while cupping the balls.” They’re so vivid and visceral, they conjure up images with almost as much immediacy as porn. So I’d be lying if I said I’ve never jerked off to an article with a clickbait-y title like “10 Easy Tricks For Getting Her Off” or “Blow His Mind With These Foolproof Blowjob Moves.”

But, also like (mainstream) porn, these guides don’t teach you much about how to have actually good sex with actual humans. They try to pin sex down, like it’s a recipe or a location on a map, without acknowledging how variable and fluid it can be in reality.

One of the things that struck me most about Ian Kerner’s classic oral sex bible She Comes First is that it’s absolutely chock full of “moves.” He groups these manoeuvres together into what he calls “routines,” which are broken down into “stages”; he offers estimates on the proper amount of time to spend on each. One such section advises, for example, “Alternate vertical strokes of the tongue with horizontal strokes. On vertical strokes, try to just graze bottom of the clitoral head without fully hitting it. Focus on brushing the head on horizontal strokes. For every five vertical, do one horizontal.” Seeing a problem here?

These “routines” are a great starting point for someone who’s never eaten pussy before and has no idea how to begin, but to treat them as gospel is to miss the point of sex entirely. So much of good sex is about paying attention to your partner’s body and their responses and adjusting your approach accordingly. This give-and-take, back-and-forth interplay is the intimacy, the connection, the dynamism, the fun of good sex. Without it, you might as well be fucking a robot or a computer: input x and you’ll get y.

One of the most popular and well-known “sex moves” is the one where you lick the letters of the alphabet on someone’s clit, starting with A and working your way through to Z. However, used properly, this technique is really more about gathering information than it is about getting someone off. By licking the alphabet, you’ll be trying out a wide variety of different types of tongue strokes – different directions, placements, and lengths – and so you’ll learn a lot, very quickly, about how your partner likes their clit touched. At least, you will if you’re paying attention, rather than trying to remember what letter comes next!

So, if “moves” aren’t important, what is? I think the answer is sex skills. Someone who knows a few recipes will effectively only be able to make those recipes, whereas someone who’s picked up culinary skills will be able to improvise a meal with basically any ingredients you throw at them. That’s how sex should be approached, I think: great sexual partners are not just great at the things they do but also great in the way they do them.

Some of the most important sexual skills are reading a partner’s body, taking feedback well, communicating your needs without being overly critical, and learning and remembering what particular partners like. There are also more physically-based skills, like staying in rhythm, fingerbanging with precision, taking a dick deep in your throat, and relaxing your muscles to take penetration. But I think the mental ones are more important, because once you have those, you’re much better equipped to work on everything else. You’ll have your partner(s) moaning your name – and you’ll know it’s because of you, not some guide you read on the internet.

 

Do you have any favorite “sex moves”? What do you think are the most vital sexual skills?

 

This post was sponsored. As always, all writing and opinions are my own.

Freelance Friday: Ruination & Regret

Q. Has there ever been a time/incident where your work “ruined” masturbation or other specific sex things for you (temporarily)?

A. This is, unfortunately, a frequent occurrence for sex toy reviewers. There’s increasing discourse about how monetizing hobbies can make them feel less fun, and I’ve found this to be true about both masturbation and writing at different times in my life.

There were, for example, two years in a row where I issued myself a daily masturbation challenge in May (#DidYouJerkOffToday) and found that by the end of the month, I could barely dredge up any enthusiasm for getting myself off. Yes, even orgasms had lost their lustre. How sad!

I’ve dealt with this by drastically cutting down the number of toys I accept for review, and by generally only accepting toys I think will be good or at least amusingly weird. My most frustrating experiences of sex toy reviewing usually centered around toys that were not good, not bad, but mediocre: decent enough to get me off, but not fun or flashy or earth-shattering or world-shifting. When using a toy is just as boring as trying to string together sentences about that toy, you know your vocation has truly drained the fun from your sex life. So I try to say no to that type of toy these days.

Sometimes people (mostly Tinder matches) express concern that because I write about sex and dating, my actual experiences of sex and dating aren’t authentic because I must be constantly filtering them through the question of “Can I write about this?” I’ve actually taken great care not to do this. I deemphasize actual dates and sex sessions in my writing, usually choosing to write about sexual and romantic concepts more generally, so that I only write about specific incidents when they’re interesting enough that I feel moved to do so. This keeps me from ruining my own romantic life by being too goal-oriented about my writing.

My partners have sometimes gotten frustrated when we needed to test a terrible toy multiple times – Lelo Ida, anyone? – and, as Epiphora has documented, this can put a surprising strain on relationships. It’s for this reason – as well as the whole “I’m in a long-distance relationship” thing – that I almost never accept couples’ toys for review. My job is ridiculous and nonsensical in many ways, and while my current partner is as GGG as I could ever hope for, I’m not prepared to risk my relationships’ stability just for a review!

Q. Have you ever published something you later regretted (e.g. because it was too personal)?

A. The week after an OkCupid boy cruelly ghosted me, I lamented to my therapist that I was already embarrassed by the post I’d written and published about it. The piece had spilled out of me in a tearstained whirlwind, and it had seemed so important that I get it out into the world. But in retrospect, it’s messy, and melodramatic, and god help me if that boy ever stumbled across it. I wish I had waited even a week before pulling the trigger.

This has become a less frequent problem since I’ve gotten serious about my blog as a full-time job over the past few years, because these days I always pre-schedule content, sometimes weeks in advance. I can’t count the number of times I’ve written something vulnerable, queued it up, and then thought, “Actually, no,” and filed it back into my drafts. There’s a piece in there right now called “10 Thoughts Upon Learning My First Daddy Dom Is Someone Else’s Daddy Now” that will probably never see the light of day, because I wrote it in 2017 after a grotesque breakup and that level of grief is akin to a state of intoxication: not a good space for decision-making.

When I showed that piece to Bex, he asked me, “Does it say useful, important things, or is it navel-gazing? Will it teach people something, or was writing it just a good way to process your feelings?” This is still my metric for the usefulness of personal essays. The great Glennon Doyle, a memoirist and blogger, says, “I never put my writing out there until I’ve figured out how this thing that happened to me is really about all of us,” and she’s so right: the specifics of your personal experience, while they might be cathartic for you to get out on the page, probably aren’t artful or interesting until you shape them into something more universal and broad. That’s not to say there’s no place in the world for telling our own unique stories – heaven knows I do it all the time – but I have noticed that the pieces I most regret publishing are the ones filled with unprocessed emotions, word-vomited up without care or consideration.

My friend Kate Sinclaire often says that if you want to do porn, you should first imagine the worst possible person to discover your porn doing exactly that, and if you can live with the reality that they probably will, then you can go ahead and do it. I think the same is true for sex writing. It might seem like a terribly good idea to publish an emotional screed about that Tinder hookup from last week, but what if the person you fucked finds it and reads it? What if your boss does? What if your grandmother does? Self-censorship can poison your creativity, but you need a certain amount of it, or you’ll drown in regret pretty quickly. Imagine the most embarrassing possible person reading your piece, and if that feels alright, then you can hit “Publish.” But please don’t do it before then, you impulsive little imp.

 

Got questions for this series? Drop ’em in the comments or in my contact form.

Monthly Faves: Gush, Good Guys, & Gold Glitter

April was a bit of a tumultuous month – I got my PayPal account shut down for being a sex writer and had to reshuffle a bunch of career stuff as a result – but I think I managed to salvage it, for the most part! Here’s some of the sexy/sensual/smart stuff I liked this month…

Sex toys

Rock Candy sent me an 8-inch blue dildo that is just a glorious hunk o’ silicone. I requested it for pegging purposes, because my Ambit is feeling a little too small these days, but the Rock Candy Suga Daddy (what a name) is probably too big for my partner to take unless we’re in the mood for a lot of warm-up. I really like it for vaginal use, though! It’s girthy but not ridiculously so, long enough to hit my A-spot, and partway between realistic and whimsical. Perf.

• I snapped up a glittery gold April Fool’s Day version of Funkit Toys’ NoFrillDo X, fully expecting to enjoy it more for its aesthetic charms than its tactile ones, but actually, it’s delightful on both axes! The silicone is firm, the length is sufficient for A-spotting, and the ripply ridges are lovely. Yay!

• Another dildo? Yep! Still enamored with the VixSkin Bandit. The dimensions are perfect for me, and my partner likes that he can easily change the angle of penetration by varying how he holds the toy.

Fantasy fodder

• My Sir and I watched GUSH, a film by my pal Kate Sinclaire, together over the phone this month. It depicts a cis man squirting – not ejaculating in the usual sense, but something more akin to vaginal ejaculation, only from a penis – and it’s amazing. It made me think a lot about how gender is a construct and you can play with androgynous energy in all sorts of fun ways during sex.

• I got an email from male companion Madison James about a hypno audio track he made (his voice is very good, wow), and it got me thinking about wanting to do a roleplay with my Sir where he plays a sex worker and I’m the client. Sex as a service has been a big fantasy of mine for many years so this makes sense. Maybe one day we’ll pick a swanky hotel bar and do the thing.

• This month I fucked my lovely FWB for the first time in a while and I found myself thinking a lot afterward about how good he smells… and also how hard he works to make me feel good… I’ve only had two sexual partners over the past 14 months and that feels jarring to me, as a former major slut, but they’re both so excellent that who even cares?

Sexcetera

• I’m pleased to announce that my new newsletter, Sub Missives, is live! It’s a place for writing that’s more vulnerable and personal than I would typically get into here. The first edition, about phone sex and mental health, is free, but subsequent editions (including one about service submission and an upcoming one about polyamory and introversion) can be accessed by paying $5/month or $50/year. I hope you’ll sign up if you want more of my words!

• Sextistics: this month I had phone sex 21 times and in-person sex 17 times, totalling 38 sessions in all, making this my most sexually active month of the year so far.

Femme stuff

• I got my first Brazilian wax this month. I grew out my pubes for about three and a half weeks beforehand, which is the longest I’ve ever gone without shaving them, and then a nice lady ripped them out of me. It was painful, but not as bad as I thought it was gonna be, and I loved the results. Still debating whether needing to grow out the hair in between waxes is worth it to me for the thrillingly bare outcome (and high price tag).

• My velvet obsession continues: I bought a pale pink velvet slip from H&M and fell in love with its ethereal vibes. I wore it to my birthday drinks get-together with a grey cardigan, a blue sparkly heart necklace, black boots, and a smoky eye.

• My boy Paul at Avalon Hair Design darkened up my hair again and made me feel like a queen, as always. Thanks, Paul!

Media

• I read Laurie Essig’s book Love, Inc. after acquiring it through the magical media portal that is NetGalley, and it kind of blew my mind. Essig argues in it that the ideology of romance is distracting us and giving us false optimism at a time in human history when we really need to focus on bigger, more pressing issues (like that whole climate change thing, not to mention fascism and late-stage capitalism). While this book didn’t quite convince me to give up my idealistic romanticism, it did remind me to look at romantic myths critically and to pay more attention to the world outside my window instead of getting caught up in insular relationships.

• If you’re interested in the restaurant/bar business, you’ve gotta watch episode 2 of 7 Days Out on Netflix! It’s a short documentary about Eleven Madison Park, a fancy-as-fuck restaurant in New York. This piece of cinematic mastery is a devastatingly well-edited and often hilarious story of hard work, setbacks, passion, and obsession. Would recommend!

• My brother’s band Goodbye Honolulu has a new single out called U Got It and it’s a bop!

Little things

Exciting career developments. The great turquoise wall in my neighborhood that makes for the best selfies. Getting my friend high for his first time ever. Big diner breakfasts while I work. Our new relationship check-in questions, which mb came up with after doing a bunch of research on relationship health (what a nerd). Surprisingly okay margaritas at cheap bars. Making plans to move in with a friend! Massively culling my wardrobe to prepare for the move. Having a decent pain tolerance. Satisfyingly organized suitcases. Being interviewed by smart folks. The new Pride Converse line. Dramatic readings of Passover poems. Hanging out with my brilliant cousin and his wife and son. Espresso at Café Olimpico. Dining in the dark at O’Noir. Montreal bagels. Riding a giant Ferris wheel with a bunch of iOS nerds. Discussing sex robots and Japanese dating culture at a fancy banquet. “I’m not a trusting man…” Oysters and champagne. Morning sex.