What to Know Before Your First Time Booking an Escort in Chicago
Before my 5 tips, a story:
“It tastes like your cum.”
We were ten years into our clandestine romance and halfway through the first course at Indienne when it hit me: this canapé carried notes of sperm. And because we share his with a kiss sometimes, I thought he’d find the observation amusing. He did.
He’s always loved exploring new things with me, and he’s always been a planner. And that evening was no exception.
He’d curated a celebratory night that carried significance at every turn, each moment referencing highlights of our decade together.
There were drinks at the scene of our first date, a stay in the first hotel in which we ever fucked, and dinner at a spot that’s worth the hype.
Early in the evening, over cocktails, I handed him his Christmas gift: the book I had accidentally stolen from the workspace we’d shared in secret last year.
We laughed at the inside joke of it all, at the closeness. That chapter of us had been unconscionably hot, and I wanted him badly.
So I slipped him a room key, palmed the contraband publication, and excused myself to the room. I prepared for him to take me.
Knowing the book’s next home would be his home office, I got on my knees, placed it between my legs, and handcuffed my wrists behind my back. Then I waited, abuzz with the kind of anticipation only trust and time can build.
This anniversary was us at our best. And it never would have happened if he hadn’t once been a new client—a man totally unfamiliar with this space—who approached booking me with care, intention, and respect. He was committed to doing things right in the beginning.
Everyone has to start somewhere.
I meet a lot of men for their first Chicago escort experience, and they tend to say the same thing: the path from first considering booking someone, to finding me, and finally reaching out was long and process-driven.
What made them hesitate wasn’t fear that I was unsafe or AI. It was about wanting to make a good first impression—approaching something unfamiliar with care, and without misstepping.
The lover in this story was no different.
He didn’t arrive in this world confident or practiced. But he was thoughtful. And the way he moved at the beginning is what made everything that followed possible.
Here are the five things you can do to achieve an equally positive outcome:
1. Understand your why, even if it’s “I want to figure out my why.”
Maybe you’re a man on a well-defined mission, or maybe you’re not. First dates aren’t about having a perfect explanation for why you’re there, and often, simply spending time with someone helps bring that into focus.
Maybe intimacy has faded in your above-board life. Maybe you’re feeling urges you want to explore with the right person. Maybe you’re craving a kind of intimacy you haven’t felt in years, or maybe you just want to turn your brain off for a while.
Booking your first companion is a moment of honest self-reflection. Many people take the plunge during periods of transition or expansion, and there’s no wrong reason.
But self-awareness matters.
When you have a sense of what’s drawing you in—even if that reason is wanting to figure some stuff out—you’re better able to choose an experience that fits, communicate clearly, and show up fully present and in the moment.
2. Respect the verification / screening process.
Verification isn’t an invasion of your privacy; it’s what allows a companion to feel safe. And every companion offers a screening process that aligns with the risk mitigation level that makes the most sense for them.
By taking the time to fully complete it, you are showing respect for their safety and security.
I am often told that my verification process feels reassuring—that it signals care, discretion, and a shared commitment to minimizing risk on both sides.
At the same time, I recognize that some people would rather book a companion who takes a lighter approach, such as verification solely through P411. That preference isn’t wrong, it simply doesn’t work for me.
There truly is a lid for every pot. So if a companion’s process or requirement doesn’t feel comfortable to you, don’t try to circumvent it or provide incomplete details.
Instead, look for someone whose model is more in alignment.
3. Communicate clearly and appropriately.
When first contacting any companion, it’s best to write a message that is clear, respectful, and non-sexual. And just as you should never discuss specific sexual acts, you should never discuss money. (That’s what a companion’s rates section is for.)
A thoughtful introduction goes a long way, and it can be as brief or as detailed as you’d like.
Simply share a little about who you are, what drew you in, and the kind of experience you’re hoping to create, and do it all without writing anything explicit.
Referencing blog posts that resonated with you (like 27 Things That Turn Me On, Animalistic, or Night of a Thousand Pleasures) isn’t necessary. However, it can be a helpful way to communicate your prurient desires without crossing the line and sending anything graphic.
And finally, asking for clarification, within reason and when needed, is part of clear communication.
If you have a query and can’t find the answer in my FAQ or on my site’s other pages, you can always send a succinct, clear, and non-explicit note to alyxchi@proton.me.
(I find that asking and answering questions is especially important when booking an FMTY date.)
4. Be yourself.
If the first three steps are about how you arrive, this one is about how you stay.
I don’t want an actor. I want you. Introverted or gregarious, serious of brimming with dad jokes, cuddly or fit, none of that matters. And if you’re nervous? Fear not.
It’s my job to put you at ease, and that’s something I do well. Jitters are appealing, and a normal human response to such a pivotal moment.
Honesty, self-awareness, curiosity, and authenticity are what make you memorable and desirable. These are the qualities that make me want to see you again!
5. Don’t be afraid to make mistakes.
Even when you approach this process with care and intention, you may still misstep somewhere. That’s human. What matters is how you course-correct with humility, clarity, and respect. Those qualities go much further than getting everything “right” on the first try.
In conclusion...
The lover in this story didn’t begin as someone confident or practiced in this world. He even made a mistake or two.
But he began as someone thoughtful. Someone who was committed to doing right by the woman he desired most.
His initial decisions are what made everything that has unfolded since possible.
And because you’re reading this today, you’re already closer than you think to making a strong first impression.
As I write on my FAQ page:
“I value bold minds over flashy headlines. And you’re demonstrating admirable boldness by simply being here.”
And you really are. I promise, you’ve got this.
