hotel sex

12 Days of Girly Juice 2020: 3 Fave Encounters

Kate Sloan

This has been a more difficult year than usual for me to keep track of memorable sexual experiences in my mind. Not because I didn’t have any good or great sex this year – I had a lot! – but because normally I have some situational or locational markers to help me remember specific instances better. In 2020, there was no “that time we did watersports after a night out at a cocktail bar” or “that time we used a new toy we’d just picked up at the local sex shop” or “that time we fucked immediately upon finally arriving at our hotel after a cross-country flight.” There was, however, a lot of “that time we had sex in bed after hanging out in bed all day.” 😂

As a result of these circumstances + the way my brain organizes sexual experiences, I don’t remember the exact dates of every stellar rendezvous I had this year, despite (still) keeping a sex spreadsheet. But I remember the feelings, and the vibes (so to speak), and the highlights – which is sort of how I feel about 2020, too. So today I’ll tell you about some of the best encounters I do remember.

I’ve also thrown in a little write-up from Matt about each of these, like I did last year, because it’s fun to hear both perspectives sometimes. Enjoy!

 

Non-reciprocal (but surprisingly reciprocal) oral

My very first sexual partner, back in 2008–2009, could have orgasms from going down on me. You can see how this experience might lead a person to be disappointed by subsequent relationships where that didn’t happen!

Of course, I know how uncommon and unrealistic this is for most people. It makes for a great fantasy – that someone could find your pleasure and your genitals soooo hot that it could make them come, basically untouched – but it just isn’t how most people’s bodies work. And yet, somehow, a decade after that first sexual relationship, I found myself dating (and eventually married to) someone who happened to have the same talent.

Some of my most satisfying sexual experiences this year were times when my love went down on me – slow, gradually escalating, dedicated, and reverent – and brought me to an orgasm so intense that it made them come against the bedsheets in the same moment. Sometimes this happened while they were in chastity, which makes sense, what with their sensitivity being amped up and orgasm threshold lowered – but sometimes it was just sorta random.

I am very lucky to have a sweetheart who loves giving oral sex that much. It feels powerful to me every time, and affirms that I am actually hot, even at times when I severely doubt that to be true. Some people chase and fetishize the elusive simultaneous orgasm during PIV – but I prefer a simultaneous orgasm during oral, tbh!

Matt says: I’ve always been a little embarrassed with past partners when I’ve come from going down on them, because of what culture tells us about “premature” ejaculation. The fact is that eating pussy is one of my all-time favorite sex acts, so of course it turns me on. And sometimes tasting someone come in my mouth is enough to push me over the edge. The first time this happened with you, I was shy to admit it at first, but when you reacted with a loving giggle and a beaming smile, I knew you were into it. This is also the most frequent way I experience simultaneous orgasms, with my orgasm almost always beginning just as you start to come and peaking as I work hard to maintain the rhythm of my tongue on your clit and ride out the waves of pleasure. It’s definitely worth the cleanup. 

 

Slapping their cock to orgasm (content note: inflicting pain on a penis)

One of the kinks Matt and I explored more this year was CBT (that’s cock and ball torture, not cognitive-behavioral therapy!). While many people with dicks are scared to death of any pain or injury befalling that area (and reasonably so), personally I think it’s nice to mix a little pain in with my pleasure – and fortunately, my spouse agrees.

We had experimented with occasional cock-slaps here and there, but one night in June after they’d already made me come with my Bandit and Eroscillator, we got into some dick-slapping that was much more purposeful and concentrated. After a few minutes of teasing slaps, I realized that it seemed like they could come from the hits I was raining down on their dick. (One of the benefits of being in a long-term sexual relationship can be developing the ability to sense such things.) I kept up my rhythm, the slaps becoming gradually more firm and fast, until eventually, they came hard, whining and whimpering.

Though I’m not much of a natural domme, there is something thrillingly powerful about being able to give someone a totally new-to-them type of orgasm. I’ve subsequently improved my CBT skillz and can now make them come with slaps pretty easily and consistently. Cool!

Matt says: I don’t remember exactly how we started doing CBT together. But I definitely remember the first time I came from it. I was in a subby, trancey headspace and every one of your slaps was making my cock harder. I felt myself beginning to leak precum against your hand and craving release. I didn’t know it was possible for me to come from slapping alone, but I felt myself getting closer as your hits became more rhythmic and focused on my frenulum. I asked for permission to come, and had one of the most intense orgasms of the entire year. It’s amazing to learn a new way to come, and we’ve had a lot of fun playing with it since.

 

Wedding night sex

Of course, there are traditionally a lot of expectations heaped onto the night of one’s wedding, sexually speaking – and though we wanted to make it special, we also knew it was just one night of many, many, many nights we’ll spend together as a married couple, so there was no need to put undue pressure on ourselves.

After our post-wedding dinner with a few friends, we checked into the Conrad Hotel for the night, where they had set up champagne and chocolate-covered strawberries in our suite (aww). After some kissing, cuddling, and decompressing, Matt fucked me with the Njoy Eleven – the dildo that indirectly led to us meeting in 2017, because they mentioned on Twitter that they liked my review of it – while I used the Eroscillator on myself. (I remember the way their brand-new wedding ring clinked against the metal of the Eleven…) Then we had good ol’ PIV. Classic.

It surprised me to notice that despite wedding night sex being considered “special,” an anomaly, in real life it actually felt pretty similar to great sex we might have on an average day, save for the location (and the fact that we had to peel off our formalwear beforehand!). I reject the idea of waiting until marriage to have sex (for myself, anyway – you do you), because it prevents you from assessing your sexual compatibility with the person you plan on tethering your life to – and the flipside of that coin is that I already knew I love fucking Matt, and that I could be happy doing so for the rest of my life. That night just confirmed it.

Matt says: Romantic! We were a little drunk and a lot exhausted, but we weren’t going to waste a beautiful hotel room and our wedding night by going to bed early. After some champagne and chocolate-covered strawberries, I fumbled around trying to figure out the complicated lighting system and went down on you in the dark for what felt like the perfect amount of time. I knew I wanted you to come on the Eleven, like we discussed. And I knew I wanted to come inside you. So that’s exactly what happened. It couldn’t have been more perfect. And then we fucked once more in the morning, for good measure.

 

Hope it was a wonderful year in your sex life, too (if that’s what you want/enjoy)!

12 Days of Girly Juice 2018: 3 Fave Encounters

Kate Sloan

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?

Come Fly With Me: 5 Travel-Sex Stories

Kate Sloan

A rumpled morning-after bed at the Wythe Hotel in Brooklyn.

I truly felt like a jetsetter the first time I sexted in a TSA line.

Leaving New York felt impossibly sad, in no small part because of the cute boy I’d just met there – but my bleary travel day was brightened by the salacious selfie I suddenly received from him as I traversed that long, slow line.

“HEEELLLPPP,” I replied immediately, my eyes sweeping over his hairy chest, blue eyes, and full pink lips. “911? Yes, sorry, I received a very fire selfie and my heart exploded. What do I do?”

Without missing a beat, he wrote back: “Yes, this is emergency services. Deep breaths, and don’t take your eyes off it. Your heart will repair itself in a few minutes once it adjusts.”

I giggled maniacally at my screen, blushed hard, tried to collect myself. “I’m in a TSA line,” I explained, “and the people around me 100% must think I’m an idiot right now.”

“Welp,” he replied, “sorry if I set off any alarms.”

“Yeah, I’m probably gonna end up on the no-fly list because of all the stars in my eyes,” I mused. “Those seem hazardous.”

I watched the undulating ellipsis as he typed, until his next words appeared: “Guess you’d be stuck in New York then…” Oh, what a tragedy that would be.

After dropping my friend Mia off at her swanky Airbnb post-drankz one night.

The sluttiest night of my life was the time I accidentally booked two sex-dates for one night. It was purely a scheduling error, not intentional at all – but fortunately, both dudes were amenable to the situation.

Dude #1 was my dommy fuckbuddy at the time. I dropped by his place for an early-evening fuck around 6PM. Wanting to try something new, I’d packed some Kegel balls to insert pre-spanking. A far cry away from traditional vibrators, these jiggly little balls vibrate your bits from the inside out every time you get hit, and they don’t even have a motor. It’s a neat trick, and it went over smashingly.

After that date was done, I rushed home and showered for my next one. Dude #2, a Twitter crush visiting from out of town, picked me up and drove us to my favorite pub. Midway through a giggly, tipsy dinner, I texted my dom from earlier, “Should I fuck this guy? I can’t decide.” He weighed the options carefully, taking the decision seriously, and eventually decreed that yes, I should return to this bro’s hotel with him. It turned my dom on, he said, to imagine me fucking someone else just hours after fucking him. (Dude #2, I should say, knew about this whole exchange and was on board.)

Hours upon hours of hotel-sex and fitful sleep later, I got up at 5AM to head out to my 6AM dayjob. As I walked down the creaky old hotel hallway, I heard a creepy clicking sound that seemed to follow me. When I stopped, it stopped; when I continued walking, it started up again. I looked behind me, ahead of me, and around me, but there was no one. My heart froze in my throat.

And then I realized it was the Kegel balls in my coat pocket, clacking together like a taunting soundtrack for my walk of shame. Whoops.

Dressed up at the Holiday Inn Toronto Downtown Centre.

At Woodhull 2016, a fellow blogger held a gathering in her hotel room. She offered up her collection of reject dildos for us to choose from. What an absolute saint.

I knew what I wanted as soon as I saw it. Unlike vibrators that are inspired by nature, this one was inspired by the utterly unsubtle dick of a fantasy creature. It was a behemoth of a dildo, in my blog’s branding colors: pink and blue. I thanked Luna, its original owner, and then cradled it under one arm as I walked down the hall and got on the elevator to take my prize back to my room.

The thing about conferences held at hotels, though, is that there are always guests who aren’t part of the conference, and you have to contend with them. I’d learned this when I took the elevator down in a loud vulva-print dress the day before – and I learned it again, as I endured an uncomfortable elevator ride with two suit-clad blushing businessmen and one giant dildo in plain sight.

I prayed for time to pass more quickly, and wished I’d brought a bigger purse. And as soon as I stepped off the elevator on my floor, I burst into humiliated giggles. What a trip.

At a hotel somewhere in Chicago.

Pros of using Hotwire to find a hotel room: it’s easy, allows for impulsive sex getaways, and is, above all, cheap.

Cons of using Hotwire to find a hotel room: you have no idea, really, what kind of hotel you’ll end up in until it’s already booked. And that’s scary. Sometimes in a sexy way. Sometimes not so much.

My first anal sex experience took place at the Knights Inn, a low-budget hideaway in Toronto’s infamously rough Regent Park neighborhood. The inn itself was sketchy and mildly unsettling, like a scene from The Shining if the film had gone a little tattered and yellow at the edges.

My valiant fuckbuddy knew what a momentous occasion this was, and how much preparation should go into it. He spent long minutes relaxing me, making me giggle, turning me on. And though he is vanilla as fuck, one way he attempted to rev my engine was by spanking me.

The trouble was, the walls were paper-thin. We could hear a cadre of frat boys getting drunk and rowdy in the next room, and though I considered this par for the course, my FWB was spooked. I could feel him backing off the spanking again and again, terrified of making noise, even though the guys on the other side of the wall were being louder than we would be all night.

My handsome friend bunched the thin hotel-bed sheets in his palms and draped them over my upturned ass, as if that would muffle the sound. He experimented with punching instead of slapping. He fretted and overanalyzed and adjusted and readjusted. Finally, enough was enough, and I told him – laughingly, lovingly – to stop.

Hotel sex is supposed to be an escape, but sometimes you still can’t escape your own inhibitions. It’s okay. There are always other things you can do.

Naked and incredulous at the Standard.

The first time I banged my Sir, we were staying at the Standard High Line in New York, one of the most beautiful hotels I’d ever stayed in. I was so nervous I could hardly walk in a straight line.

As we checked in, the clerk asked, “Are you sensitive to noise? This room is right underneath a nightclub, so it can get loud.” It wasn’t an issue. We had no intention of sleeping, and we planned to be pretty loud ourselves. Not that we told the clerk any of that.

My beau pressed the wrong elevator button twice before he got his shit together and hit the right one. He was nervous. It was cute. I was smitten.

I had packed a slew of sex toys, anything and everything I thought we’d need: impact toys, fancy glass dildos, travel-friendly vibrators, cuffs, a blindfold, a book we both loved (which is indeed a sex toy, depending on how you look at it). At his command, I laid it all out for him to look at, arranged it carefully like an Instagram flat-lay, because I wanted him to be impressed.

He must have been impressed, because as soon as I was done, he bolted toward me and pushed me against the floor-to-ceiling plate-glass window looking out on the city. His kisses were fierce and hot and immediate. I knew what was coming and I knew I would be taken care of. I will never forget the way he looked at me, so tenderly and searchingly, as he removed my clothes for the first time – and the way that cold, cold glass felt against my back as my heart pounded in my chest.

Hotel sex can be many things, but it is almost never boring. I can tell you that much.

 

This post was sponsored by THE LILY by Fleurotics. (They’re running a crowdfunding campaign currently that you should get in on!) As always, all writing and opinions are my own.

How to Have Anal Sex For the First Time (If You Are Me)

Kate Sloan

image

Begin innocuously enough. Go out for dinner with the crush/bang-buddy/friend to whom you’ve just given a blowjob. Get a little drunk with him, on big pints of locally-brewed beer, and laugh at all the jokes he’s making because weed and BJs make him cheerful.

While talking about your sexual goals for the year, suddenly have a brilliant idea – but the kind of idea that maybe only seems brilliant because you’re drunk. Start to tell him, but think better of it. Cover your mouth with your hand. Blush a lot. Shake your head. Let him pry it out of you, because the more that you keep it inside, the better an idea it seems. Finally: ask him if he wants to be the first person to fuck you in the ass. Because you want it. Because you trust him. Because he’s been on both sides of butt stuff plenty of times before and knows what he’s doing.

Be pleasantly surprised when he immediately agrees, and yet also not surprised at all, because he’s sweet and chill and adventurous and seems to genuinely like you. Concoct a plan with him, involving a hotel room and hours of slow, luxurious warm-up. Nod sagely when he tells you, “Let’s sleep on it and decide tomorrow,” while knowing in your heart of hearts and butt of butts that you’ve already decided and the answer is yes. Pay the cheque and tipsily stumble back to his place together. Give him one more BJ for good measure before saying goodnight.

The day before, text all your friends and tweet to all your followers about your sodomous plans and get their advice. Put your favorite butt plug in and leave it in for hours on end, to re-acclimatize your ass to penetration after a long stretch of none whatsoever. Masturbate idly while the plug is inside you, savoring that weird mix of pleasure and unfamiliarity. Wonder idly if you should’ve invested in an anal thruster for a more realistic warm-up.

Send dude a link to a cheap hotel listing, which is your indirect-and-yet-very-direct way of saying, “Yes, I still want you to fuck my ass.”

Pack a bag full – and I do mean full – of toys and other sexual accoutrements. Two Pure Plugs, the Ryder, and the large Ripple. Two bottles of lube. Black latex gloves. A zillion condoms. A tightly-folded Throe. The Pelt, incase of spanking. Salsa, Tango, and Hitachi. Put the Uncut #1 in there because you’ll want something roughly the same size as the dick that’ll be going in your ass, and when you put the Uncut in your mouth to test its size, you think, “Yeah, that feels about right.” Start getting real fucking excited.

While tipsy at a Valentine’s Day party, hide in the bathroom and sext the dude: “Very much looking forward to doing things to you with my mouth tomorrow.” Because you’re slightly obsessed with blowing him. Squeal when he texts back, “Bring toys.” Later, actually scream, at a totally inappropriate moment during the Valentine’s party, when he sends you a picture of a woman getting DP‘ed with toys. Because, holy shit, he’s going to DP you. Go home and add the Eleven and Double Trouble to your already-bulging toy bag because you suddenly want him to ram you with something big and heavy.

The morning of, do what you usually do when you’re anxious: journal a lot, listen to soothing music, and worry disproportionately about how to do your makeup. Have a breakfast of 3 Oreos and a cup of coffee, because you’re too nervous to eat real food and also because coffee will help clear out your system. Go about your day, running errands and writing and doing chores, while inevitably unable to focus on any of it.

As the sun starts to set, glaze your body in coconut oil so you’ll be nice and soft for him. Get in the shower and shave your legs, your armpits, your vulva, your butt. Like most lengthy femme rituals, this is more about the way it makes you feel than the way it makes you look: eliminate some of your anxiety by eliminating all of your body hair. Wash your body with Lush’s “The Comforter” shower cream, because smelling like berry candy makes you feel like the hottest, beautifulest babe. Fill a bulb syringe with lukewarm water, squirt it into your ass, jump up and down a bit, then let the water flow out of you. Do this a few times, until you feel confident and clean.

Put on some cute underwear, a comfortable outfit that’s easy to remove, and minimal makeup that won’t flake off if you end up face-down on a bed. Take deep, calming breaths and then dance your ass off (no pun intended) to energizing songs for a last-minute burst of confidence.

Walk to the streetcar stop, carrying your heavy-as-fuck toy bag. Ride the streetcar and wonder what the other patrons would think if the bag accidentally spilled open and they saw all your butt plugs and fancy dildos. Get off where Google Maps tells you to, and walk toward the hotel. Start feeling intensely dizzy, partly from anxiety and partly from the exertion of toting sixteen pounds of sex toys through snowy city streets.

Arrive at the hotel, which is small and strange and reminds you of The Shining if it was shot on no budget. Schlep your stuff up to the second floor and find the room number that the dude texted you. Smile when he opens the door for you, because he’s cute and you like him and you’re happy you’re gonna do this with him of all people.

Tell him you’re anxious. He is too. Assuage your nervous hearts with weed for him, gin and chocolate for you, and giggly makeouts for both of you. This is a never-fail prescription.

Give him a beej. For two reasons. One: his dick is excellent, and having it in your mouth turns you on faster than just about anything else. And two: if you get nervous and back out of your buttsex plans, you won’t feel as bad about it if he’s already come. This move is strategic. Or… strabeejic, if you will.

Lube up a Pure Plug and slide it into your ass, while he gives you sage advice on technique and angle, like some kind of butt sherpa. Laugh a lot, because he’s doing silly impressions and voices for your amusement, and think: yeah, I definitely chose the right person to do this with.

Let him do stuff to your nipples and clit and G-spot, because holy fuck, he has talented hands. Do your best to give directions, because sometimes you get too shy to boss people around but you know you’ll need to be a top-notch communicator tonight if he’s gonna fuck your ass. Don’t come yet – you wanna save that for later.

Bend over and let him take out your Pure Plug and switch it for the Ryder. Recall when you first bought your Ryder, years ago, and tried to put it in with no warm-up and not enough lube, and how goddamn awful and stupid that was. Enjoy the contrast between that moment and this one: the slick way he slathers lube on the plug and lines it up just right. The utter ease of taking a big toy when you’re really ready for it. The encouraging words in your ear as you back up onto it and it slides in, pop, no pain, no problem.

Make out some more. Touch each other. Giggle. Play. This isn’t a race. There’s no schedule. No marks to hit. No obligation to follow through. Just do what you feel like. Teach him how to spank you. Show him how you like your clit touched. Tug on his chest hair. Kiss his cute face.

Recognize your readiness by how relaxed you feel. Anxiety dissolved and apprehension bested, grab a condom and some lube and get him hard in your mouth. Pull the plug out, slowly. Bend over the edge of the bed with a Hitachi pinned between your clit and the mattress. Smile against the sheets, because this feels like a game.

As he slides into you, breathe deep, cleansing breaths of calm focus, and then fast, heavy breaths of unexpected pleasure. Moan, writhe, bite your lip, grind against the Hitachi. Think about how easy it was for him to push into you. How hot, hard and slippery he feels inside you. How good this is, how much better it is than you even expected. Feel completely safe, and taken care of, and respected, and filled, and fucked.

Stop him after a couple minutes, because the sensation is… a lot. Curl up beside him and high-five him when he announces, “So, you’ve officially had anal sex now!”

When he asks how he can get you off, let him choose between the Eleven and the Double Trouble. Smile as he weighs each in his hands, taking the decision as seriously as you knew he would. And then lay back and let him fuck you so perfectly with the DT while the Hitachi’s mashed against your clit, until you come in the long and loud and wild way that you only ever come with partners who make you feel unashamed. Kiss his big lubey hands when he wraps his arms around you afterward and says, “That was hot.”

Once you’ve come back to earth, put your clothes on and go out for celebratory dinner and drinks at a nearby pub. Because, hell yeah, good sex is worth celebrating.

 

This post contains a sponsored link. As always, all writing and opinions are my own.