Escorting: It’s complicated

Many escorts have a straight forward, matter of fact, attitude towards the business. They understand exactly what they are doing and are clear about the pleasures of making good money from escorting. Other girls have a more complex relationship between their lives and escorting.

We got a very nice note from Julia – not her real name – who seems to have taken an almost entirely unique approach to the complications escorting creates in a busy life.

We reached out to Julia on Skype and had a marvelous conversation, but before we get to Julia’s story, here’s the note in full.

by Hannah Jay

Dear Miss Jay,

At the moment I live in a biggish California city. I am twenty eight. I’ve been escorting on and off since I was nineteen and, truth be told, I usually enjoy my dates.

So far so good. Now the complicated part. I have always had a bit of an attraction to girls. Not any girl in particular and I expect, when I grow up, I will be that lady with the two kids and the house in the burbs and a very nice, male, husband. But, at the moment, I have found myself in a bit of a fix.

I have a pretty deep submissive streak and I was trying to figure out a way to work that into my escorting. But, as I am sure you will agree, escorting can be dangerous enough without encouraging your dates to act aggressively. Though submission has nothing to do with aggression, if you advertise as a submissive you get all sorts of creeps and weirdos.

But there is a girl I know who is a bit of a domina. She actually has a lot of the gear and, more importantly, I trust her. We’ve done dates together and it has worked out very well. The problem is, well, along with being a domina, Clara is also exclusively interested in girls. More particularly, she is interested in me.

Now she wants to start offering our services to the very large lesbian community in our city exclusively. Again, I have no great objection to lesbians, but I want to continue seeing my straight male clients and Clara says I shouldn’t.

We make great money in either setting so that is not the thing.



As I read Julia’s note I wondered whether this was an escorting issue at all. I am a huge believer in individual choice and it sounded from the note as if Clara wanted to be the boss of Julia – which, given the domina submissive dynamic would make some sense; but this obviously went beyond that. I wrote Julia back and suggested a Skype call. A couple of days later there she was.

What a pretty, faintly ethereal, girl. Long, golden red hair which curled beautifully, the sort of porcelain white skin which only redheads have and which, so far as I could see, had never really seen the sun. She wore a sort of neo hippie peasant blouse which suited her perfectly and revealed a remarkably ample bust for a girl who seemed quite frail. I could see why she did well in the escorting game. She was softly spoken and very, very polite.

After we spent a few minutes of small talk I got to the point.

“It sounds to me as if Clara, along with being a domina, is also a bit of a bully.” I said not wishing to beat around any bushes.

“Maybe. I just don’t know. What it comes down to is that she has a great idea looking out at the lesbian market. There are just not that many escorts working with lesbian clients and our actual work together turns out to be very lucrative. Plus, once you are seen as a lesbian friendly escort you get lots of single dates too. But I don’t want to just be with girls. I have a lot of male clients and a lot of regulars who I want to keep seeing.” said Julia.

“Ok.” I said. “But let me get a bit of background. How did you and Clara end up working together?”

“It was pretty simple really. As I wrote, I have a really strong submissive side. I really like being told what to do. But the problem is that if you put that sort of thing in an escort ad you risk getting some really nasty clients. I knew there was a market and that the escorting clients in that market would pay a lot of money to be with a really submissive girl. But I also knew that there were really unacceptable risks to doing a submissive role escorting business. It really only took one bad date.

I tried to figure out a way to do those submissive escorting dates but I realized that I would not have enough control over the situation. I mean how much control do you have with even mild bondage? None.

So I looked around and eventually I found Clara who was advertising as a travelling domina. Which meant that rather than having a dungeon in-call she had what she called her “bag of tricks”. Ropes, whips, strap-ons, hand cuffs, a few extra large sized panties, masks – it was amazing.

We spent a bit of time talking about how we could do escorting dates together. I am perfectly happy to do what I am told by a male or a female client so long as Clara is there. And, of course, Clara loves having her little submissive to play with. But it is a very mixed message. Domina, submissive and escorting client. How does that work?

The answer was a lot of fun. On our escort dates I played the role of either an ingénue or a maid. I had outfits for either. For the ingénue it was all about a pretty, innocent dress, white lacy lingerie and pretty stockings. My mistress, dressed in her best jodhpurs and wielding a long black leather riding crop would “force” me to pleasure the client. I was Little Bo Peep and the client had the starring role of the Big Bad Wolf to mix our fairy tales entirely. Sometimes our client would spank me for not doing what I was told, other times Clara would use her crop to keep her innocent Miss at her work.

An escort date as a maid meant that I would arrive in uniform and serve the client and Clara drinks and snacks for a little while before Clara would start to find fault. With every fault she found I would have to do something a bit naughty. You can imagine. Eventually I would do something which required actual punishment and Clara would have the client give me a spanking or she would give me a whipping while the client watched. My level of actual punishment depended on what Clara had negotiated in advance and the more severe the more money we made.

Eventually, and this part I liked a lot, I would be sent to the bedroom and ordered to strip. Then Clara would tie me to the bed. To get the client going she would often use one of her strap-ons before telling our client exactly what he or she was to do to me. We gave new meaning to the idea of activities between consenting adults. Which was delicious and that’s why I am having trouble with what Clara wants to do now.”

“Which is?” I asked.

“Well, Clara has been advertising our, what, “thing” at a few sites where the audience is pretty much exclusively lesbian. We did a few dates with lesbian couples and then, well, she booked us into a really nice Palm Springs house for “The Dinah”. Which I had never heard of but it is pretty much the premier “girl” event in the US. For five days we played. I was the full time maid except when Clara took me out on a leash to events. We made a lot of money. I mean a lot.

But, probably as important as the money, we met a lot of women from all over California who wanted us to come to their place for a night or a weekend. Enough women that, if we wanted to, we could do nothing but lesbian escorting dates for the next year and make tons of money.

There was a problem though. A number of the women asked Clara if I ever went with men. Clara hummed and hawed but it really was a big deal. Apparently some of these women really cared and if Clara checked in with them later that was one of the biggest questions before these women were willing to book an escort date.

Of course I did go with men. I have a really good escorting business which doesn’t have anything to do with Clara. Clara says that if I quit escorting with men we’ll make even more money on the lesbian circuit in Cali and a few other states. I think it is dumb to miss out on business with clients who have been, in some cases, regulars for a couple of years.”

“Is there any reason given for why these women don’t want an escort who also sees men?” I asked.

“There are a lot of reasons. Right off the top there is a whole political thing. I had never realized it but there is an entire lesbian world that has its own clubs, parties, and, yes, escorts. While these women are “out” politically and are certainly not in the least bit secretive about the fact they are gay, they are very discreet about how they like to play. The whole maid thing was really transgressive.

In the lesbian community the whole question of dominance and submission, BDSM, can get really political really fast. So can the idea of escorting. When Clara and I work a lesbian escort date there is often a lot of awkwardness about how to characterize and present our fee. For some of our lesbian clients the whole “escort for money” thing was deeply problematic for their usually very egalitarian, New Age, view of the world. We’d always be able to work it out and the ladies usually dropped the whole New Agey thing when they had a pretty little maid in a very revealing outfit to boss around.

Into that sort of awkwardness the idea that I might be doing this same sort of submissive date but with men was a huge issue. I’m not saying that we stopped the date to have a consciousness raising session, but when I was intimate with a number of these women they would make it very clear they preferred if I stayed exclusively with women.

Part of that was a huge paranoia about STDs. Like any responsible escort I am super careful to avoid consenting adult activities which have high risk levels. Party hats to be worn at all times. Basic safety rules. But for our female clients the mere fact that I sometimes escorted men suggested that I had a much higher risk of STDs than I would if I had exclusively lesbian clients. Which may be true for all I know. The thing is that as an escort I take my precautions very seriously and I have never had a problem.

I think, that at root, a lot of the women who hire Clara and I for dominance and submission dates are just really uncomfortable with the fact I escort independently with men. It is not a reasoned thing. It is very much an emotional thing where they can’t imagine that I might actually be escorting men because I enjoy male sexuality.”

“So,” I asked, “If it was totally up to you what would you do?”

“I don’t know. Honestly. Clara has pretty much said that she will not do any more dominance and submission dates with men so that part of the equation is solved. Which is a bit of a relief because Clara really did not do well with men at all. She was awkward and the escorting dates usually fell a bit flat.

And I have to say the dominance and submission escorting dates with women are amazing. Once we get past the money thing, which is a lot easier the second and third time, these women just have a wonderful time. A lot of our lesbian escorting dates are with couples and these girls are wonderfully kinky. Clara fits right in and I have a lot of fun playing the naughty maid or the pretty young virgin or, a new one, the waitress. Or I am just Clara’s super submissive girlfriend who is shared around with the other ladies. It doesn’t really matter because I like all of it.

The thing is that if you are a submissive woman and an escort it is a lot safer to do that with other women. They have all sorts of wonderfully inventive kinks but, so far, I have yet to run into the sort of scary, aggressive behavior you see with so called “dominant” men. The women come from a different and, I think, healthier place.

A lot of the lesbian dates are way longer than the regular escorting dates. We will arrive at someone’s house at five for drinks – which I usually have to serve – and then have dinner – which I usually have to serve – and then after dinner entertainment and, usually, time in the bedroom with one or both of the ladies whose house we are visiting. Nothing is rushed. And, of course, our lesbian clients understand that they are paying for our time, all our time, so it can be a very lucrative evening.

What I would really like to do is have three nights a week for my straight male escorting and the rest of the time devoted to Clara and her sort of dates. That would be ideal. But, as I said, it’s complicated.”

“Is it really Julia?” I asked. “It seems to me that, even though you are sexually submissive, you are the star attraction in the whole lesbian thing. Clara may act the mistress of the situation, but the whole party turns on the idea and reality of a sweet, submissive girl being introduced into the mysteries of Sappho. You are that girl. Which puts a lot of bargaining power in your hands.”

“But Clara says…”

“Never mind what Clara says.” I said rather strictly, “When girls work together there needs to be a partnership. Clara may be a domina but that is a role she plays when you are escorting. And she may be essentially lesbian in her personal sexual orientation and good for her; but she is not your boss or your owner or any other unequal thing. Your role as a submissive, bisexual, escort is just as valuable as hers if not more so. Which means you have a say if you are willing to be firm.”

Poor Julia. Being firm was not something she was very good at. Or at least she didn’t think she was.

“But Clara will be angry. She’ll probably stop escorting with me and I really don’t know if I could do the lesbian dates on my own even if I could get them.”

Whether it is escorting or any other business, you get what you want because you make a plan and stick to it. Which I explained to Julia and we ended her call with her promising to call back with results. Two hours later my Skype went off and there was Julia.

“It worked. It was amazing.”

“It” was, of course, a very simple plan for Julia to equalize her escorting relationship with Clara. It turned on one simple fact – Julia was very much in demand with both her male and her female clients. And, clever girl that she actually was, she had kept track of all her clients. I had suggested she phone her three favorite lesbian clients and ask if they would be interested in her services on her own if she decided to offer that option.

As you might guess, all three couples jumped at the chance. Julia was, after all, the star attraction, Clara was much less essential.

“I booked two solo dates next weekend.” said Julia somewhat breathlessly. One of them is an overnight where I will be the ladies’ intimate maid from Saturday afternoon to late Sunday. Which is such a lot of money and they are such nice women.”

“Did any of them mention Clara?” I asked knowing the answer.

“No. They all seemed okay with the idea that I would be doing their escort date on my own.” said Julia.

“And how did your call with Clara go?”

“She was pretty mad. But I told her I would still do some dates with her and that calmed her down a bit. But then she started to get mad again when I told her I would be doing three nights a week of straight dating.”

“Which was when…” I left it hanging.

“Which was when I told her I was seeing the two couples solo. She calmed right down and started making nice. So we’ve worked it out. I will keep seeing my male escorting clients and I will do a few solo lesbian escorting dates. But, I told Clara that I was happy to work with her on dominance and submission dates with lesbians a couple of nights a week. She has to book the dates and I will try very hard to be free to do the work. By the end of our call I think she had convinced herself it was her idea.” said Julia, “Thank you Miss Jay.”

“You’re welcome.” I said. The fact was that Clara needs Julia. But Julia just proved to Clara that she could escort on her own. The power shifted.