Here’s To You

Posted on 2019.06.24

When I first crossed over to the “Mature” category, I found myself in the company of Clients who preferred a Companion closer to their own age. We had similar points of reference, and enjoyed many of the same activities. But lately, quite a few of my requests have been with men much younger than I would have ever expected. I know it’s become a “thing” and I’m not offended by it at all. I actually find it amusing.

When they book, they know I’m a mature Companion, but the look of surprise when the meet me in person always gives me a laugh. Darling boy what did you expect? A walker? Orthopedic stilettos? Women today take care of themselves in much better ways than the generations before us and our efforts are going to show. Despite what many of them think, I’m natural. Still, they sit across from me and study my features, looking for evidence of work done.

The younger Clients look up to me like some sort of oracle and I enjoy my new status thoroughly. My younger Clients are usually inexperienced and shy around women. I think they choose me in hopes that I will “educate” them and that’s what I try to do. I tell them stories from my past and watch them hang on my every word; sometimes I get the impression that they want to break out a pen and paper to take notes. I always tell them that if they want to hear the story again, all they have to do is book another date with me.

One younger Client actually refused to believe my age and thought that Cupid’s had lied to him. I laughed and explained that we don’t need to lie; there are plenty of young Companions available. He then asked to see my ID, which I of course refused since my ID has my real name. Disappointed at being told no, he was respectful of my privacy. I did manage to convince him that I was indeed a mature and experienced Companion. I taught him to recognize some signs, to listen for clues, and few other things I’ve learned. Once he was satisfied, we continued to enjoy each other’s company.

I also enjoy what my younger Clients are able to teach me. Younger men tend to be more open minded, more adventurous, and despite what many people say about millennials, I actually find my younger Clients to be very considerate and appreciative.

There was one young man who spent all of his teens and early twenties focused on his studies. His parents had allowed very little social time which meant that he found himself feeling very awkward in situations. He was confused as to how to approach or engage with a woman without becoming a bundle of nerves. Eventually he gave up on traditional social interactions and found himself approaching 30 and feeling quite depressed about it. All those years in university paid off because once he started to do his research into improving the social part of his life, he discovered the benefits of Companionship. He was one of those men who thought that my age automatically meant that I was a teacher. Between you and I, I think men who feel that way just used to have a crush on one of their teachers when they were younger and being with me fulfills that fantasy. My young Client explained all this to me over drinks on our very first dates and I was fascinated – this was one of the first times I had gone on a date with a younger Client. He had booked me for a GFE and in the morning, he asked to book me again. Soon enough we were meeting almost monthly; whenever our schedules aligned. Dinners. Lunches. Even a vacation to St. Bart’s for New Year’s Eve.

As time went on, I could tell that his confidence levels had grown. He was more outgoing and self assured in public. In private, he was still sweet, but definitely less shy. One day over lunch he told me that he had started his first relationship and that he hoped I wasn’t offended. I wasn’t offended at all! I was feeling quite proud. It was almost as if he had graduated. I raised my glass in a toast to his good news. He said that he had told his girlfriend about me and that he wanted to continue seeing us both. I told him that if they were okay with that arrangement, I was happy to continue seeing him. I watched his shoulders relax and smile spread across his face and we proceeded to catch up over the rest of our lunch.

I still see him a few times a year. A promotion at work means that he travels a lot more than he used to. His birthday is coming up, and he’s already informed me that he’ll be booking me for the entire weekend.

Photo by Pexels

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Jillian Hollander Jillian Hollander