How I Did It Then

I started this in 1996. You can read about my inner journey to my decision to be a Courtesan, here and here. Here, you will see how I began my stint once I had made the decision.

When I divorced, I did not drink, did not go to bars (except one for Irish music occasionally), did not party, had always been self employed so did not have a large pool of business friends. My community was made up of couples. As a result, I used our local paper's personal ads to meet people as I was not yet an internet person. When I started this, I had an idea sortakinda of how escorts worked- they worked for an agency for all I knew. But I did not want to be an escort. I wanted a relationship. It was logical for me to place a discreet specialized Mistress ad in the personals of my local paper.

Again- I had no idea what to "charge." No idea how to do figure out how to figure it out. I had the Old Guy advising me on it as he had done it before, but he is...as I always used to tease him...a "frugal" sort of guy. As I have said in other posts, I was not ready to sleep with lots of guys (had already done that as a teen, wink, wink). I flipped out after about six months of sleeping with what was for me too many men who I had no connection to. After my hiatus with only the Old Guy, I got very very particular and exclusive.

I discovered the internet and the world of online personals. I put an ad on Yahoo and got tremendous response because I posted a picture. The ad was very discreet, but flowery, stressing all the things I had to offer a few very select gentlemen. I got very clear about my intention, what I wanted to create for the men and why. I then did my best to communicate this. I talked about building a relationship of love without falling in love. That I would only be with people I genuinely liked. About how I could provide all the wonderful aspects of a relationship without the entanglements. I said things like "generous" but also added that I was looking for someone who would be supportive of me in all ways, like I would be to them. That I would create a time out of time for them. I mentioned I was trained in the arts of love and companionship both modern and ancient, and would consider men with sexual challenges. I stressed that I would only see people long term, so that if they were seeking a one night stand, we were not a match. I got over 600 responses in a very short time. My ad was so discreet that only the ones who had done a relationship like this before or who were on the ball "got" it.

I got very very particular in my screening. As time went on, I got even more so. I was intense and brutal, in fact. Given all the "odds" against me (age, level of support and time commitment I eventually asked for), one would think that I would have been more accomodating. But I learned that the more exclusive I made myself, the higher I set my standards and requirements, the more I screened out, the more perfect people ended up showing up. It took time. And lots of weeding, talking, IMing. But this worked for me because I ended up only sleeping with men who stayed for years. I believe it is because I developed a friendship first. I listened to the gents with my body and my mind. I listened to my guts most of all. Any internal glitches in the matrix, or if they got "three strikes" I moved on. Quickly. I did not look back.

I had lots of "rules." Any penis pictures...gone. Rude or arrogant...gone. Pleading to meet me before I was ready, gone. No interesting note in the response, delete. Under 50= gone, 50-55 were maybes, over 55 best. I was brutal about the age thing. You would be amazed at how good I got at guessing ages on IM just by the way I was approached. They start by asking for another picture, they never heard from me again. Boring gone. Players gone. No cyber sex. Ask about freebies or sampling, gone. I had very specific reasons for my weeding catagories and they served me well.

If they got past that initial stage, I was intense with those I allowed to the first level of screening. My first questions were:

What is your definition of a Mistress relationship? If they didn't mention financial support, I would change the subject to find out other things in a round about way before broaching the subject. There were times when I would stop contact before they ever figured out that I wanted to be financially supported if they did not seem open to the idea or other factors weeded them out.

What is your job? Do you like it? If not what would you prefer doing? If so, what is it that excites you about it?- I asked this for a number of reasons. A job is a big part of men's lives. If a man is happy in his job, this says lots to me about how much of his life is going. The question and the way I asked it was also a way to tap into learning about what makes this person "tick." In addition, I did this to assess if I thought they could financially sustain this type of relationship for a long period of time. I will talk more about this one in the next post.

Why do you want this kind of relationship? As I had as my prime directive to find men in a difficult situation, primarily the "holding hostage" reason, this was an important one that I went into pretty deeply by asking lots of questions. If they whined, bad mouthed or blamed their wives, I screened them out. If their story touched me, I continued to listen. If I felt they could get this need met easily for one reason or another, like if they had had a number of mistresses, I moved on.

What does a relationship like this look like to you? How often do you want to meet? What time of day? How long of sessions did you envision? Did you want an activity partner, too? Or was it mostly about bedding? Do you see travel involved? Any overnighters downline? How long do you see it lasting? (Note...many had not thought this through and it got them thinking more.)

Had you ever had a relationship like this before? If so, what did it look like? (re: in regards to questions above that you envision here)

Are you willing to go slowly in getting to know each other before bedding? I told them I want to get to know you as I am more interested in what is between your ears than what is between your legs.

Are you willing to get tested for STD's? Ever had any? Are you willing to practice safe sex? What is your definition of safe sex? If your definition of safe sex is different than mine, are you willing to practice my way? (Always...I mean ALWAYS mine were more stringent. People do NOT know safe sex. It's fucking scary.)

(Wow...so long since I have written these out...used to do them lots in responses, but it has been so so long. Funny how it's kind of like riding a bike after a long break...hehehehe....)

I was pretty intense. I would spend lots of time emailing and IMing. I would take weeks to meet in person. I figured that if they stuck around there online, that meant an interest that would have a much higher possibility of sticking around in the real world. I also like the art of subtle seduction and the ways that things come out over time. If we sparked intellectually before involving bodies, I thought we had a much stronger chance of making something work.

My spiel about what I wanted:

I was clear that I had a few others but they were long term relationships. All knew of each other, but did not know each other. Everyone knew this and knew that if they had a special something they wanted to book, they had to do so in advance. And that if a particular date was gone, everyone worked together to make things flow.

I told them that I needed to meet them in person AT LEAST twice for long lunches with lots of thinking time in between with IM or email to learn each other before bedding. Generally I met with them more than this. It was a good system and the longer I did it, the more I liked it. It weeded out people. During a first date, the excitement can be high. Moving forward always seems like a good idea in the moment. But with time and piercing questions on my part, there were men who decided this was not for them.* This was always a relief to me, and I was happy I had not slept with them.

I asked that they come into this with the intent of it lasting a minimum of six months, perferably a year. That while I was not asking them to sign a contract, I was counting on their honor and to really look within and be honest with themselves and me as I really did not want to sleep with lots of men. I knew life could not be predicted and they might not be able to not stay that long, but that I was looking and asking for honesty about intent.

I told them I wanted to learn them, so would be listening with all of me, to learn not only their likes and dislikes that they were aware of, but that I would do my best to also discern their unspoken needs as well. I had an apartment/temple because I did not want to build a relationship in a hotel. I wanted it to be familiar, home, a haven for all who entered. I bought them the soap, shampoo, and deodorant they used at home so they would not smell different. Their little personal basket also had a razor (Gillette???...hehehe...this was pre-Loverman so I was not Gillette then), comb, toothbrush and their favorite brand of toothpaste. After they had been with me for three months I bought them a robe that was theirs. I did a detailed interview of foods, beverages, music, etc, that they liked so they had their creature comforts there. I had a massage table if they wanted that, toys, outfits. It was heaven for them.

Inevitably, the money question would come up. And that was a whole other spiel.

To be continued.....

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*Due to the nature of my my ad, which everyone said was different than any other they had ever seen, I talked to quite a few men who were getting the nerve to go outside their relationships for the first time. Some of them, after talking to me, decided to not continue down this path. I think it's important for people to get support for themselves. Sometimes, when the idea is met with support, love and acceptance they are then truly free to see how they would be in the situation and choose differently. This is not an easy topic to talk about for men. They are in pain, they don't know what to do and they have no one to talk to. Just talking can shift things....but I digress.....