A Clients Point Of View

My First Escort Experience: Tales From the Male Point of View

A Louisville, KY business executive shares some details from his first foray into the world of a professional escort.

For years, a good friend of mine has been trying to convince me to consider utilizing the services of a professional escort. I have always had a bit of an aversion to the idea because my perceptions have been built by watching television shows where the profession is not always portrayed in a good light. Plus, I always thought to myself, “what kind of a guy hires an escort, anyway?” As I have recently learned, many of my preconceived notions and biases were completely off-base.

First, let’s talk about the men who utilize this type of service. After discreetly asking around some of my social and work circles, I learned that there is not a single stereotype for men who have hired an escort. Rather, my inquiries led me to wide array of professionals, business owners, entrepreneurs and philanthropists. These are intelligent, educated, respected men. And these are the types of people from whom I received testimonials once I started talking honestly about this subject. I discovered that I had been judging not only the profession, but also the individuals who participated in the rewards. So, somewhere along the way my line of thought started to shift. And I opened to some previously unexplored options in my life. After all, there are only so many years that can go by where a married man can be left to feel unloved, unwanted and undesirable. So this shift in thinking is what led me to my first encounter with Joann.

This leads us to the ladies who have chosen this as their profession. If your background is anything like mine, you’re probably not picturing the type of experience that I had. Again, too much television depicting drug-riddled street corners and less than desirable people.  My first experience introduced me to a woman who is kind, thoughtful, intelligent and ambitious. In other words, a true professional. We met in her apartment and she was immediately warm and gracious.  I had told her up front that this was my first experience, and so she was incredibly patient with me as I asked several questions. Actually, my intention was to spend the entire first visit just getting to know Joann. After all of my introspection and soul searching regarding this decision, I wanted to get some insight into the person with whom I would be sharing a brief but intimate encounter. I’m not sure how typical this is, but did enjoy our conversation and I’m grateful for Joann’s honesty and patience with me. Primarily, I just enjoyed getting to know her a little better. So, by the time things became intimate I felt like I was with a friend.

Finally, I wanted to relay some of the things I learned along the way – before my first meeting with Joann. The whole thing started kind of rocky because I listened to some bad advice.

1.       Finding someone – even a cursory web search will probably land you on some pages that advertise professional escorts. As with anything else on the internet, be careful what you click. Most of the initial websites I encountered were legitimate, but there were some phishing sites out there just trying to get information from unsuspecting individuals. I ended up utilizing tryst.link, but there are many others out there.

2.       First contact – here’s where I made my biggest mistake. Someone told me, “If you text an escort, be vague about who you are and what you want.” Turns out, that’s a terrible approach. From my end, I felt like I was protecting myself. But, think about it from the ladies’ perspective. They need to be careful and protect themselves as well! If you’re not giving them solid information to go on, how are they going to make a decision about whether they can trust you. From a safety standpoint, they are taking a bigger risk than you!  And you might encounter someone who doesn’t trust you. Here’s an excerpt from a text exchange with the first person I reached out to:

Me: Hey there, I heard you’re a good person to contact if I wanted to do a wine tasting? (TERRIBLE opening, gives no information, and why would she even respond?)

Her: Where did you here that from?

Me: A friend of mine pointed me to a place called tryst and said it’s a good place to find someone who might be able to help me out with an inquiry like this.

Her: What a helpful friend you have… Unless you have 2 providers u have met before able to verify ur legit and safe and they are reputable… then I cannot meet you. I’m sorry. To much bullshit on the phone and shit and I’m tired of weeding through what is fake and what is not. Sorry other people have ruined it for everyone.

Me: hey, no worries, That makes complete sense. If there weren’t some kind of process, it would concern me. Not sure how to get started but I do appreciate your frank/honest response. Any advice or direction for someone just looking to make a friend in this way?

Her: It’s not a make friends site. We all get paid. My frank response yes because you know I already know. If you really wanted to be my friend then you would be legit and cut the games. High schoolers play games not adults who are almost or over 40.

Me: Okay, look, I’m sorry – I just wasn’t sure how to approach this. If I said or did anything incorrectly or appropriately, It definitely wasn’t my intention. In the same way you need to be cautious, so do I. I’m not interested in games either. Apologies for my misstep and best wishes.


(here’s where it really goes off the rails)

Her: And all that is exactly how I know it’s Katie or one of her friends she had put up to fucking with me. Isn’t old yet? Must be exhausting to have me on ur mind constantly every day. Flattering but ridiculous and petty and very childish…

Me: Lol. I have no idea what all of that means, but it sounds like you think I’m someone else. No worries. I’ll try to figure something else out. Have a good night!

Her: Again you say the exact same shit every time. Like, the only one that is fucking putting so much effort and time into this is you and it’s so stupid you should be embarrassed of yourself. That’s the most childish stupidest shit I’ve ever seen.

Wow. This is where I removed myself from the conversation and initially decided that I would never try something like this again. And that’s when I saw the link to workinggirlky.com and read some of the stuff that Joann has written on there. Which leads me to point number three…

3.       Be prepared – if they have a website or a blog, go read it. Many of these ladies will give you ample information about themselves that will help you understand the rules a bit better. I devoured the information provided on workinggirlky.com and it left me feeling much more prepared than I would have been otherwise. I walked in with a complete understanding of appropriate donations and how they are to be handled. The information is out there, you just have to be willing to read it.

Now that I’m on the other side of my first escort experience I’m truly glad that I took the time to figure it out.  Despite that initial, terrible text exchange, I pushed on and was able to meet someone that I’m comfortable with. We’ve already had our second appointment and I’m looking forward to more. My last bit of advice is this: be respectful and kind in every encounter. From my limited experience and the feedback that I’ve been given by others, these are professionals who want to deliver a great, personalized experience to each of their clients. And, like many other things in life, you get out of it what you put into it. She’ll do her job, yours is to come prepared, follow her rules and treat her well. It should be well worth it in the end.  

Good luck, and feel free to share your own experiences in the comments below. I’d love to hear them!

Lucky In Louisville

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