Confession One: The Hotel Room

I wasn’t planning on taking another booking. It was my last day touring in Georgetown, and I’d already made 4K. The day had been exciting and honestly, a bit more intense than I’d expected. As soon as my date left, I went straight to peek inside the envelope. He’d been generous. They usually are. But no matter how many times it happens, there’s still this little voice in my head that goes, “Are they really paying this much… for me?”

So I started packing. I was done for the week and already thinking about Miami. Back then I had a roommate, and was shamelessly living a full-on double life. These little “work trips” had to be planned down to the hour so I’d never raise suspicion.

While daydreaming about my bed and a pint of Jen & Berry’s in a hot tub, my logical brain was already busy crafting the absurd stories I’d have to tell Jenny. She was a chill girl, managed a beauty clinic, and never crossed boundaries. The problem was her bestie.

They both knew I was always loaded and mysteriously out of town every two weeks. And that nosy friend started whispering doubts. That maybe I was into something more than just freelancing as a PA.

Plus, she had this snoopy, chubby little dog that was weirdly obsessed with my dirty lingerie. But that, I’ll save for another confession.

Anywho, just as I was patting myself on the back for surviving another DC tour, my work phone lit up. That was a last-minute outcall request at the Ritz-Carlton. As soon as I read it, my stomach did a little flip and I felt something warm coming from my legs. Thought it was arousal. Nope. It was a curse. I laughed, prepped my sponge, and moved on to business.

He was polite, straightforward and had enough references on TER to put me at ease with just a couple of words. But it wasn't just that. 

Friday night. 9 PM. The Ritz Georgetown. There’s something about that combo that just hits different. Maybe it was the way he said it. Maybe it was me flirting with the extra 2K I’d pocket. Or maybe it was how effortlessly he assumed I’d say yes. I let it sit for a moment… then said, “Sure,” and immediately spiraled.

I’d never been to the Ritz Georgetown. And listen, I know I don’t seem shy, but stepping into that lobby dressed like sin in a black cocktail dress, sheer tights, and fuck-me heels, well that takes Olympic-level training. I wasn’t staying there. I wasn’t even supposed to be working. But there I was. I left my cab and walked past businessmen and bored wives like I belonged, like I wasn’t about to be railed in a room I didn’t book.

The good thing was he already knew what I looked like. I mean, I’ve been advertising myself as a high class escort all over TER and EROS, and not to flex but being ranked top 20 in DC does come with its perks.

So while I was playing dumb in front of the elevator panel like I had a room key, this tall, mid 50s gentleman came up to me smirking like we had a life secret. As soon as his lips touched my cheeks I knew what was about to happen. 

Inside the hotel room I could feel his energy shift. There was no rush. I sat on a side chair and crossed my legs to discreetly reveal my garter belt while he stood up to offer me a drink. I’ll drink occasionally, but even if that bottle screamed money, I was still meeting a stranger in a hotel room. 

He threw himself onto the bed like I was his new psychologist and started spilling the tea about his ex-lover and how she broke his heart. I actually thought it was adorable when he pulled out a photo of her. A few drinks in and it was clear his marriage wasn’t in the same shape as his business ventures. He played golf, liked chardonnay, didn’t smoke, and seemed so damn genuine — not me falling on the first date with a client after being professionally rearranged all day.

With time passing, this man really had me looking forward to the scene I came for. He invited me to his bed and wrapped his arms around my waist. I have a weakness for a bear hug. We started making out, and even if it was technically a date with a price tag, I was loving being on top of this man in those bougie-ass sheets.

I was getting dangerously high on oxytocin, so it was time for condoms. I reached into my purse to grab one and that’s when I realized I fucked up. My head started spiraling. I had forgotten them and I was mortified. In my head, I was flooded with one intrusive thought screaming: he will never book you again.

But this man got up, laughed, called room service, slipped 300 to the guy from room service, and I guess that counted as him asking for discretion. Because all I know is he got his condoms in under two minutes. I was like, damn. That DC power.

With condoms secured, I let myself go. He kissed me like he meant it. I blew him like an ex-girlfriend begging for forgiveness. When I felt his knees shaking, I did what any self-respecting slut would do — I climbed on top. He was generous. I left with sore thighs and a new regular.