The Best Sex We Had This Year
InsideHook contributors share their most memorable sexual experiences of 2021
While attending an alumni holiday party for my semi-elite alma mater earlier this month, I learned that it can be difficult to tell a room full of people who all seem to work in finance that you make a living writing about sex for the internet. It shouldn’t be; this was a career I dreamed of and pursued actively, but it turns out that even if you love what you do, telling a Goldman Sachs employee that you’re honoring your shared alma mater by writing about sex toys and blow jobs is demoralizing in a way for which I simply was not prepared.
So, like many people, I’ve spent the last few weeks of this year thinking about why I do what I do.
When you write about sex for a living, people often assume you are very horny or very sexy, very experienced or perhaps just morally depraved. I am some of these things, I wish I were others. But that’s not why I do it. It’s not because I love writing product blurbs about waterproof sex toys, explaining why everyone on the internet wants to fuck the Grinch or even doing my small part to combat the pervasive sexual shame and censorship that still lingers like a puritanical vestige at the heart of society. I enjoy those things, too, and I’m even passionate about some of them, but that’s not why I’ve built a career around sex.
I did that because I’m fascinated by desire, in all its forms: illicit or sanctioned, fulfilled or thwarted, expressed or repressed. Desire, of course, can be many things, can have many objects. But one of the most prominent, ubiquitous and arguably powerful ways in which human desire manifests is sex, whether real or imagined. I am obsessed with the kind of desire that makes you want to crawl inside another person’s skin in search of a form of intimacy we can only approximate by pressing our naked bodies together, the kind of desire that makes men willing to burn their entire lives to the ground for a stolen moment with a coworker or a stranger they met on the internet. I am even obsessed with the desire that makes them marry the wives they cheat on in the first place, the kind that makes us say, “Yes, this one. I want this one so much that I want to have her forever.” The kind of desire that makes us believe that could ever be possible.
In college, I had a writing professor who often waxed poetic about the power of sex. After all, it can create human life, she would remind us, daring us to name another force capable of such a feat. “What a serious thing sex is,” she would muse.
I sometimes took issue with this lecture, specifically the emphasis on the procreative powers of sex when, in practice, sex so often has nothing to do with reproduction at all (at least not intentionally). A queer atheist, however, she wasn’t trying to preach to us about saving sex for the sanctity of love, marriage or babymaking. Rather, I believe she was simply trying to remind us that sex, and the desire that fuels it, is a very powerful force, that whether you do it with one person or thousands, with a life partner or a stranger, it should be respected as a very serious thing.
That doesn’t mean, of course, that it can’t be fun, beautiful or silly. Sex can be all of these things, and often it is. But, like all other forces brilliant and powerful, desire can destroy as much as it can create. We should be careful with it, yes, we should respect it for the very serious thing that it is, but we shouldn’t fear it, or hide from it, undermine or be ashamed of it.
It’s easy to forget, even when it’s your job, but sex is something worth taking seriously. In honor of this very serious thing, I’ve asked a few of InsideHook’s sex and dating contributors to share personal stories of their own most memorable sexual experiences this past year. These are stories of sex, yes, but they are also stories of desire. Some are funny, some are delicate, some are raunchy, some are sweet and some are silly, but they are all, on some level, very serious.
Melting Into a Moment
After a year of pandemic isolation, I had high hopes for a hot vax summer. But a few weeks after I got my second Pfizer dose, a dental x-ray upended my plans. It showed a tumor growing inside my jawbone, eating away healthy tissue and slowly warping the bone outwards. A few frantic days and invasive tests later, I learned this particular tumor was both exceptionally rare and aggressive. To prevent it from gradually destroying my face, and potentially metastasizing into full-on bone cancer, I needed about half of my lower jaw removed — and a big chunk of bone and flesh taken from my leg to rebuild it — ASAP.
In the weeks leading up to that surgery, a toxic mix of stress, anxiety and insurance shenanigans obliterated my sex drive. And in the months since, I’ve had to grapple with a slew of long-term side effects: My leg is less stable than it used to be, and still hurts if I overtax it. Scar tissue in my neck and face have changed the shape and mobility of my jaw, slightly but still noticeably. A severed nerve has left a fourth of my mouth and half of my tongue numb, save for a faint pins-and-needles pain triggered by touch. It’s also left me with limited control over my lower lip.
I’ve lived with a balance and movement disorder since I was six, accumulated a slew of injuries over the years, and come to terms with all of it. I write about navigating sex with disabilities. (In my own case, I steer clear of positions my disorder won’t let me hold, accept that I’ll never have dexterous fingers, and find fun uses for my tremors — they’re a source of all-natural vibration, no batteries or recharging required.) So, you might think I could take these changes in stride. But getting blindsided like this is enough to throw anyone for a loop — and more than enough to throw those of us prone to depression into a funk. And so, I fell into fear:
If I can’t control my lips or feel my tongue, can I kiss worth a damn anymore? Fuck that, can I even go down on people now? What if a partner touches my face and it turns to fire? What if my leg won’t let me hold the positions I love? Who’s going to want to deal with this cursed body?
Then, a few weeks ago, a close friend and occasional partner asked if I’d be up for a hookup. I was nervous. But the trust and connection I have with her trumped all of my irrational concerns.
So, I said yes.
She didn’t say a word about my face, leg, any of it. She just went in for a kiss, and minutes later we were tangled together on my bed, melting into a moment. As we tumbled about, I’d bump my leg, or she’d brush my face, and she’d clock me wincing slightly. But rather than breaking the moment with worry, she’d just pull back a bit — enough to let me shift her body or my own.
Through her willingness to roll around until we hit a groove, she made space for me to re-learn my own body. She helped me integrate surgical recovery into the pleasure of sexual exploration.
Objectively, this romp was run-of-the-mill for the two of us: Sweaty, spit-drenched and spine- tingling, sure. But no more than usual. Yet it was still some of the best sex I’ve ever had because it was exactly what I needed after a year of pain that came hot on the heels of a year of isolation.
Great sex doesn’t have to be utterly toe-curling and mind-bending. Sometimes, great sex is just the sex that helps you to reconnect with your body. To feel at home in your own skin once more.
The Happiest Ending
It’s our last night in Tokyo, and we’re racing from the sex club in Ginza to our hotel in Shinjuku because I’m running late for my happy ending massage. I finally get to the hotel room, and there’s a cute boy who looks vaguely like a K-Pop star holding a gift bag waiting for me by the door. “I’m sorry I’m late!” I shriek as I run toward him. He laughs. We don’t have a language in common, but we don’t need many words for what we are about to do.
After we get inside the room, I tap out, “It’s my first time, you show me what to do,” on Google translate. He nods, kisses my neck, and leads me to the shower. We each take our turn rinsing off, then the sex toys come out of the gift bag, and a strange man begins to pleasure me until there’s a knock at the door — and a new strange man arrives to take over for my best friend’s turn.
We didn’t go to Tokyo intending to be sex tourists, we went for our sex podcast, but our last interviewee dared us. Sure, we can talk about the different levels of sex work in Japan all day, but would we try one of them ourselves?
So we tried “home delivery health” — basically UberEats for erotic massage — and we liked the experience so much we skipped around the next day, high-fiving anything that would let us. “How cool is my boyfriend?!” I exclaimed. “How cool is my husband?!” Sofiya chirped back. Neither of us could believe how chill our partners had been when we asked for permission. It made me love my boyfriend even more. We’ve been together for over five years now, and I don’t care who you are, it’s hard to keep sex as spicy as time goes on. I don’t have any polyamorous ambitions, but just knowing my partner is DTExplore was awesome, even kind of a relief — especially since we’re talking about being together for the rest of our lives.
This new spirit of exploration continues to echo throughout our partnered sex life, including some of the best sex we had this year, on a mini-vacay in Vegas. Our room had a glass wall leading out to the balcony and was slightly visible to people in the pool (I’m an exhibitioist, I love that shit). And honestly, fucking on fresh hotel sheets is unbeatable. Yes, our dog was on the bed (she always wants to be next to us), but we still managed to bang it out in all of our favorite positions.
The irony is, after all this exploring and semi-exhibiting, the best sex I had this year was actually plain vanilla, just my boyfriend and I at home alone on Christmas Day thanks to Omicron, totally relaxed, with nowhere else to be.
800 Pounds of Man
I love being the center of attention, especially when it comes to sex. (What can I say? I’m a greedy slut.) That’s why, whenever I have a threesome, I end up in the middle of a daisy chain (i.e., the center position, where someone is penetrating me as I penetrate the third).
But this evening’s itinerary — a five-person gangbang — wasn’t about me. It was about a friend of a friend who lives on a farm in rural Connecticut. Unsurprisingly, Grindr is dead up there, which is why he needed to get railed by enough men to keep him sexually satisfied through the brutal COVID winter ahead — a final hurrah before his impending sexual hibernation.
I knew nothing of this man — not even his face. My friend Javier had simply sent me, my boyfriend and his other boyfriend (not a typo, just polyamory) a picture of his juicy, hairy ass, and we all simultaneously replied in the group chat: “Yeah, we’re down.”
We scheduled the event for Monday evening. “Come to mine at 6:30 sharp,” I messaged everyone. “It’s a school night, and I gotta be in bed by 10.”
Everyone arrived right on time, and that’s when we got our first look at Peter IRL. The farmboy had a bawdy. I guess that’s expected when you work on a farm performing manual labor daily. Still, a 6’3’’ bottom with a big, plump booty is hard to come by. He also had a very handsome mustachioed face, but to be honest, his face wasn’t all that important for the evening’s plans.
We had a few drinks, and then the festivities commenced. It was an hour of sex every which way. Everyone had sex with everyone. Everyone had their penises in everyone else’s mouth, and everyone came, except for me. They all began catering to me, but since everyone had just orgasmed, no one could get hard. Luckily, I have enough dildos to fill a swimming pool, and my boyfriend grabbed the newest in my collection, a 15-inch, maroon tentacle number.
Then, despite it not being my gangbang, I got all the attention. My boyfriend worked the tentacle into my booty as his boyfriend went down on me, while Peter kissed my lips and Javier sucked on my nipples.
Eight hundred pounds of man devoting all their attention to me; I thought I had died and gone to heaven. After about 20 minutes of paradise, during which I received multiple prostate orgasms, the pizza had arrived, and we feasted like the ravenous pigs we were.
They left soon after, and I was in bed by 10, just as planned. “Well, you did it again,” I thought to myself. “Somehow, you managed to make yourself the center of attention at some else’s gangbang.”
I almost felt guilty — almost — until I remembered the joy on everyone’s face when they saw just how much of that tentacle I took.
It turns out when I’m a greedy a slut, everyone wins.
I didn’t intend to spend 2021 celibate. It wasn’t a goal — I only wanted a brief hiatus after an afternoon spent fucking and anally fisting a man that left me feeling empty. I tried to fill the hole with milkshakes on the drive home, only to end up pooping myself in an office parking lot. As I wiped shit from my ankles with Baskin Robbins napkins, I thought, “Maybe I should pump the brakes.” I wanted to take a step back to really think about the role sex was playing in my life.
I came close to ending my celibacy on a few occasions — on a date with a couple at the new dungeon where we played sexy Jenga and watched others, a few FetLife and Feeld exchanges that fizzled — but never took the trip to pound town.
In the meantime, sexting felt like a way to keep exploring and auditioning future partners. I have been sexting since we called it “cybering.” It adds a fun call and response element to masturbation, as well a way to gather intel on what someone’s into. I sexted with a local chef, a dom from Chicago, an artist in Michigan, a few randoms on Kik, a French exhibitionist and a TikTok DILF.
Daddy TikTok was the best of my sextual partners. I found him on my FYP and slid into his Instagram DMs. We flirted until it turned sexual.
One Saturday morning he sent a selfie from bed and texted, “Good morning.” I sent back a similar picture, making sure my bare shoulders were visible to subtly indicate I was topless.
“Wish I could slide right in.”
“Slide right in, then slide right in?” I messaged with a winky face. Not my best line, but I’d just woken up.
“Exactly. I woke up rock hard.” I liked the message with a heart and asked if he was busy. I didn’t want to get started if he had to hop out of bed to make his kids breakfast.
I recorded myself saying “Good, because I’m touching myself and thinking about you fucking me,” and hit send.
He texted back, “That’s so hot. Sexy ass voice”.
I continued sending voice notes, hoping he’d catch on.
He did, lowering his voice and calling me “good girl.” Was he so good at this because of TikTok and knowing how to make the most of 30-second content? Or because I hadn’t had sex in months?
I didn’t care. I grabbed my Magic Wand and went to town on myself as we continued exchanging explicit voice notes. It was the best parts of sexting and phone sex combined: the time to craft a response, and the perfect balance of fantasy and reality. I loved knowing he was jerking off to me and not sending recycled pictures, as I’d often done while sexting and scooping cat litter. His voice changed as he got closer, combining with his grunts and moans like an interactive erotic audiobook.
I usually take a while to get close, but not this time. After a few minutes I asked permission to come, adding the requisite “Please, daddy.” I wasn’t sure I’d last much longer and didn’t want to pause.
“Yes, but I want to hear you.”
I held down the button and tried to ensure I recorded all of my gasps and moans while also holding the vibrator on my clit. I hit send, grateful to feel tingly bliss instead of emptiness, regret or shit running down the back of my leg.
At the beach with this new man, eyes on fresh landscapes of skin. Under the guise of sunscreen, hands course over shoulder blades and the gentle curve of a spine. We are with his friends, so I keep myself from pressing my lips softly on his chest, just under his collarbone, on the nape of his neck, running my fingers along the shapes of his back.
I wonder if he has seen these mental gymnastics because he says we could make dinner at my place. I say something like sure, but what I mean is *a cheerleading squad gleefully flinging their pom-poms in the air.*
Later, kissing on his couch, his feet keep banging into the lampstand and we laugh. It’s a little too small for two bodies. His bed stares at us from the next room. Linen sheets, more space. New space.
I remember his textures, roughness of hands with a light touch, buzz of hair on the back of his neck, heat of skin still warm from the sun. The slow removal of layers in between kisses, in between the answers to what turns you on? He listens. I listen. I am not afraid to ask for what I want.
Later, words whispered softly in my ear and hands moving slowly over my ass. Yes, more please. A hungry kiss on my hip under a bikini string. We are nervous, we say. I feel safe. Liberated. Places generally not easy for me to go.
Later, a finger that slides between my thighs, a voice that praises me for being so soft and wet. Yes, more please. I love that.
Later, long slow strokes that twist my back into arches. Later, my hips on top of his, his hand wrapping around mine on his chest; eyes, tiny oceans, staring up at me. No, not staring, looking at me and not through me. Watching. Enjoying. He sits up, our chests closer. The shape of his arms, the hair on his chest, those eyes again, so clear and full.
My hand slides softly around the back of his neck, that buzz on my fingertips. I sink my teeth gently into his shoulder and he moans. We are a duet of breaths. I feel seen, desired. Free.
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