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.
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.
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.
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.
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.