Welcome to what is always the filthiest entry in my 12 Days of Girly Juice series: the one where I write about my favorite 3 sexual encounters of the entire year.
Moreso than being the best sex of my year, these are usually more like the most memorable, emotional, and/or ground-breaking encounters of my year. But yeah, sometimes they were also the best.
Predictably, this year all three of these were with the same person: my boyfriend/Sir/daddy, who I jokingly-but-not-at-all-jokingly refer to variously as my “dream dom” and a “sex god.” The only time this has happened previously was in 2016, when I guiltily chose 3 encounters with the FWB I was in unrequited love with, and he mimed affixing a badge of honor to his chest when I told him about it. But this time, it’s not embarrassing, because my BF not only knows I love doing sex and kink stuff with him – he works hard to make that the case. Aww. So without further ado, here are the 3 most memorable sex sessions of my 2018…
High Line First Time
I’m sentimental about first times. Many of us are. It’s a particularly useful trait for a sex writer, though, because first times are often juicy and exciting and strange and interesting and worth writing about. This can be true even if the sex itself is straight-up bad, as it often is when you’re learning a new person’s body.
However, my first time with my partner wasn’t bad at all, and I imagine that’s because at that point we’d spent many dozens of hours discussing and dissecting our kinks, sexting voraciously, and having phone sex in the dead of night. As a sex educator, I often advise people that sexting and discussing sex before the actual event can make it a lot better, but I think I didn’t fully realize that in practice until this year, when a boy I’d only spent about 2 hours with in person ever somehow fucked me better than… well, let’s just say… probably everyone I’ve ever met on Tinder, combined.
It happened at the Standard High Line, truly one of the most beautiful hotels I have ever seen, let alone stayed in. After checking in, we rode the elevator up to our room; he pressed the wrong button twice before finally getting us to our floor, because he was nervous, though he seemed otherwise as cool and collected as ever. The room had floor-to-ceiling plate-glass windows all along one wall, so I stared out at the city while we talked and giggled and took our coats off and laid out all our sex toys on a table. When a lull fell upon our conversation, he growled and pounced and shoved me up against that windowed wall, its coldness pressing into my back while his warmth pinned me there. He kissed me breathless and then started peeling my clothes off while looking up at me with utter reverence, like, “I can’t believe this is happening; I can’t believe I’m this lucky,” and that’s how I felt, too.
What followed was about 6 hours of sex, so things get a little blurry here. I remember feeling nervous and comfortable all at once, and crying out in pain while he scratched and bruised me in our big white bed. I remember that he hypnotized me in person for the first time, and I felt astonished all over again by his competence and the depth of perversion that matched my own. I remember that he bent me over his lap and spanked me with a paperback copy of Bluets – the first gift he ever got me – while intermittently reading passages from it aloud, which seemed to me then (and still) like the most goddamn romantic thing I could imagine.
When he held me down with one hand and pushed the Eleven into me over and over with the other, I thought about how this very dildo was the first thing we ever talked about, in a quirky and casual exchange on Twitter – and how it felt like things had finally come full-circle. And inside that circle was a lot of goddamn orgasms.
Melting in His Mouth
Speaking of orgasms… The gendered orgasm gap is still a rampant issue culture-wide, with countless factors contributing to its existence. In my own life, where this gap has existed, it’s usually been due to two main factors: the men I was fucking weren’t very good at touching vulvas, and I wasn’t very good at telling them how to touch mine. (If these problems sound familiar to you, please read and/or ask your partner[s] to read She Comes First and Becoming Cliterate, stat!)
This pattern explains why I’ve grown so blasé about new partners going down on me: they’re often not great at it, and it’s rare I feel brave enough or even invested enough to want to give them a crash course. But if someone makes it clear that they want to stick around in my life – and I want that too – I’m much more inclined to put the work in so they can learn how to get me off, especially if they’re appropriately enthused about this prospect.
My partner told me in some of our first explicit text conversations about his passion for eating pussy, but unlike many men who brag about this, he dropped some words and phrases that displayed a deeper-than-average understanding of cunnilingus, such as “stamina,” “enthusiasm,” and, uh, “Ian Kerner.” (Sex nerd in the haus!) My interest was piqued, though I remained skeptical.
The first time he made me come with his mouth, we had been dating for 6 months. I’m confident it would’ve been sooner if we weren’t long-distance, but even local partners usually take a while to figure it out. We made out for a long time, him grinding a thigh firmly against my vulva (a mutual fave) and biting and spanking me. He told me I’d been so good that I could choose how I wanted him to get me off, and I requested the Eleven and Magic Wand – but we didn’t even get that far, because in the midst of him warming me up with his mouth on my clit and his fingers pressing into my G-spot, I realized I was quite possibly going to come that way. I managed to choke out, “I’m getting really close, Sir,” and he knew just what to do, staying the course until my whole body tensed, spasmed, and finally relaxed.
He kept pounding me with his fingers afterward, because he knows I like that and is a gem. Hot tears poured out of my eyes. I know orgasms aren’t a dependable measure of love, devotion, or even attraction or skill, but it felt to me in that moment like he had found yet another way to prove how much he loved me. Figuring out how to make me come is hard, and actually executing the process is hard too, but 5 of my 30 lifetime sexual partners (!!) have managed it. In each case, they were people who really, really cared about me, and who made me feel comfortable and safe. What a beautiful thing.
His eyes sparkled with emotion when he crawled up my body to lie beside me. I asked him what he was feeling and he said, “You just came in my mouth. That’s really fucking intimate.” I had to agree.
Woodhull Wonderment
A friend-who-shall-not-be-named was able to procure me some marijuana-spiked edibles at the Sexual Freedom Summit (shh), and it led to some of the best sex of my year. Thank you, anonymous and resourceful friend o’ mine.
Prior to meeting me, my boyfriend had never tried weed, but under my careful stoner tutelage, he waded into high sex this year with me. While I’ll gladly smoke up and bone down any day, there is something special about sex on edibles: the high is (in my experience) slower, trippier, and more all-encompassing. True, you can overdo it more easily with edibles and it’ll take longer to come down from your fuck-up if you do, but if you get the balance of intoxication just right, it can be some of the best sex ever.
That was the case, this one fateful night at Woodhull. We each munched half a weed cookie, and by the time it hit us, we were on the balcony of our hotel room, kissing and pawing at each other in the stupefying heat. I’d paid extra for a room with a balcony, wondering when I booked it whether we would even use it – and because of this night, I’m glad I did.
Our makeouts got intense on that balcony, the way they can when inebriation strips away your self-awareness. I was craving pain, as I often do when high, so I asked him to slap my tits; he slipped them out of my dress, standing in front of me so no onlookers would get an eyeful, and smacked me around until I was panting. Then he switched to slapping my face, bringing me down full-force into a deep and disorienting subspacey state.
We wandered back inside and partook of what would soon become one of our favorite activities: high facesitting. Though we’re both fans of facesitting in just about any state, weed really amps up our enjoyment. The time dilation and disinhibition of a good high helps me relax into riding a partner’s face without worrying that I look weird, sound weird, or am taking too long. Meanwhile, I am sure the sense-heightening effects of weed help my BF enjoy tastes, smells, and sensations even more than usual – and in a reclining position, he can enjoy them in lavish repose. Ideal.
I fucked his face for who knows how long. Time didn’t fucking matter. When we were done, he told me, “You sat on my face for the perfect amount of time,” although neither of us could say with any certainty what that amount had been. As with most good sex, in retrospect I don’t remember many details – just the overall sense of hotness, closeness, and wild abandon.
What was the best or most memorable sex you had this year?