The Ritz d*ck.
On telling the story of an audacious old acquaintance who thought he'd wine and dine me in exchange for a wild night in the Ritz Carlton.
I always told people, “Don’t do me wrong or you’ll end up in my book one day.” And this is one of those pieces. I originally wrote it in December of 2022, partly to practice recounting memories, and partly to let off steam.
This is the story of an experience I had with a high school classmate while he was in town on business. I went in expecting to have a couple of drinks and a meal with an old friend and he had other things on his mind. This story is 98.41% true with the 1.59% being a change in or redaction of identifying details.
The title of this is a tad misleading. This was no on-going rendezvous with some rich bachelor who could afford to splurge on rooms at the Ritz every Tuesday afternoon.
No, this was a dick. Who thought he could woo me with Ritz bar drinks and finger foods then whisk me up to his room and have his way with me.
Enjoy
I went to high school with Trent Jackson.
He was a year ahead of me but we had a couple of classes together and saw each other quite frequently. He never showed interest in me, and at times was mean to me and had a big crush on one of my friends who did not like him back.
Over the years after high school and college, he’d occasionally pop up in my DMs on Twitter. Mostly whenever I’d post a shot from one of my boudoir photoshoots. He’d say things like “It’s so wild seeing you like that but I can’t lie and say that I don’t like it. I’d love some exclusive shots sometime.” I would usually laugh them off or roll my eyes and ignore him while letting him know I wasn’t on that kind of time with him. Looking back, this probably should have been the red flag that kept me on alert.
One day he casually let me know that he’s in DC often for work and wanted to take me out for a drink to catch up if I’m ever available. He’d hit me up a few days before he’d be in town with an offer to grab drinks and dinner. The first few asks I initially declined because I was either unavailable when he came or bogged down by depression and not wanting to be out and about. Eventually, though, I’d finally agreed on a day I had nothing planned and wanted to get out of the house.
He was staying at the Ritz Carlton in DC and invited me to the restaurant inside. I had no reservations about meeting him there at his hotel because it was convenient for him after work and because it was lowkey. I didn’t want to be somewhere busy and booming with happy hour and after-work patrons.
The conversation was going well but I was a bit annoyed that he talked heavily about work. It’s no secret that I hate small talk and work talk and would much rather catch up about life on a deeper level. He let me know that he was now a consultant at Booz Allen Hamilton. He said that once he realized football was not going to work out for him in college, he set his sights on business and now he’s here. He made sure to gloat about all the perks of working for Booz that he enjoyed, making special mention of his generous per diem amount and option to stay at the Ritz. He told me to order whatever I wanted because it was all on the company. I internally rolled my eyes and said out loud “Well, you know I do work for Deloitte, right?” In a tone that I hoped said “I’m well acquainted with nice accommodations and per diems, sir, and mine is probably bigger.”
Eventually, I was pleasantly surprised by how the conversation evolved. We had two or three drinks each while catching up so we were both more relaxed and began shooting the shit about life in general since high school. As the conversation was winding down, Trent let me know that he had a couple of j’s he’d love to share with me if I was down. And I was because, why not? He bragged about being an expert at indulging undetected during his stays and I agreed to go to his room for privacy.
You may be thinking, “Okay Ashleigh, why would you go to his room?” I have no physical or sexual attraction to this man and I genuinely believed we were going to the room to get high and finish the conversation since it was going so well. He wasn’t being overly flirtatious and gave no inkling that that was where his mind was. I also wanted to chill on his room couch for an hour to sober up before making the drive home in DC traffic.
Once in the room, and after a few passes he started to get smiley and excited and I assumed that that was how the sativa was hitting him. Eventually, though, he started talking and said “Wow. I can’t believe we’re here. I’ve been looking forward to this for a minute. Like Ashleigh, I had THE BIGGEST crush on you in high school. Like what are the odds we’d end up in this moment? Like this is huge and I feel like we should make it memorable. You got any ideas on how we could make that happen?” His smile turned into a mischievous smirk.
My comfort level instantly sank as it set in what his intentions were.
I began the mental mission of sobering up quicker than I initially planned and get tf out of dodge. I started beating myself up thinking “Why the fuck did I drink AND smoke? Why couldn't I see he’d try something?” I did not believe he’d harm me because he’d always been respectful, but the discomfort increased the more I realized I’d have to reject him.
“Uhh, not THAT..,” I said with a nervous chuckle, “Besides, I’m on my period.” This was the truth, I was indeed on my cycle. But also I announced that to remove some of the awkwardness and unsuccessfully mask my discomfort.
“Well, I mean..” he says as he begins rubbing his legs so fucking creepily, making his shorts rise higher with each rub, “That’s no problem with me, but I mean, I did always love those lips. Yeah, Ashleigh with the lips.. You know you could uh..” he says with a slick smile on his face that made my stomach turn.
The fucking nerve of this man.
“I am not doing that either, Trent. I am not sucking your dick.” I said in a firm tone so that he knew I was serious and not feeling whatever he thought this was going to turn into.
After getting the hint from my tone and realizing he fucked up, he stopped rubbing his legs, put on a puppy dog face, and said “I didn’t mean to come on so strong I’m sorry that wasn’t my intention. If I made you uncomfortable I apologize. I was just excited to be here with you.”
I was already on the couch across the room from him and announced that I was going to use the restroom, an action meant to give even more separation. While in there I sobered up as much as I could, drinking water and washing my face, and got the fuck up out of there. I declined his offer to walk me all the way down and I blocked him on Twitter before I even got to my car.
When I got home I immediately texted my older sister who also knew him because I had to tell someone what just happened.
Me: Hey! Remember Trent Jackson from high school?
Sis: Yeah, why?
Me: Girl, why did I just meet up with him and [insert an abridged version of the story you just read]…
Sis: Oh woooooow, ain't he married?
Me: Excuse me, WHAT?! Trent Jackson?! Are you sure?!
Sis: Um, yeah, hold on.
Sis: Attachment: Image of Trent in a tuxedo standing next to a beautiful young woman in a white wedding gown.
Me: No fucking way. No way. No fucking way. The mother fucking audacity. The fucking gall.
I quickly found his wife’s Instagram account using the picture my sister sent. Her most recent picture was one of her and Trent post-hike with a caption singing his praises as a husband. I was even more appalled and thought “Girl if only you knew what your wonderful God-sent husband was up to behind your back!!!”
I spent the next hour or two going back and forth on whether I should hip her to what her husband is up to on his business trips and eventually decided against it. What ultimately kept me from doing so was the fact that 1. nothing happened, 2. they could have an open marriage, and 3. some random chick who went to high school with her husband messaging her about him propositioning her for sex probably wouldn’t go over well and I didn’t want to bring unnecessary drama to my world.
I hope he’s doing terribly.
Thank you for reading ‘here comes the sun.’
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I wasn’t ready for the “I hope he’s doing horribly.” 😆 or the fact that he is married! How slimey 😵💫
I am bookmarking to read this I wish I could devour all your work in a moment all at the same time!!!! But just wanted to say how I die at the sheer breadth depth and wonder of your writing I can’t!!!!!!!