The Mistress Option

Mady had two girlfriends come to stay just after New Years. We had great fun dressing elliot as a maid of all work and having him serve the ladies at lunch and for cocktails and dinner. Needless to say the girls were both amazed and eventually amused as Mady and I put elliot through his paces.

His humiliation was enhanced when, each afternoon, he was required to submit to a punishment: the first day it was a good hard shower brushing because he had stared just a little too hard as Chriss - one of the girls - very ample chest. He had to lift his maid's skirt and pull down his frilly rumba panties before I gave him a lecture about respecting women and then two dozen good swats.

The next day Mady wanted to show her friends how easy it was to make a man ejaculate even when he is locked in a chastity cage. She bent him over a cane backed chair with a saucer below his imprisoned cock flipped his skirt up and pushed his remote-controlled prostate massager up his backdoor. It only took a few minutes before he was dripping ejaculate onto the saucer. And, of course, when he was drained he had to drink up his mess. The girls were mesmerized.

The last day they were with us, Mady and I thought they should have a bit of fun. First, each girl practised with a light cane on poor elliot's bruised bottom. It took a little while, and many "vocalizations" from elliot before each was able to accurately deliver her dozen strokes. "No, dear, you have to hit both cheeks otherwise you won't get the right welt pattern." Then elliot was required to thank each of the girls with his tongue before being sent to his corner. Great fun for the girls and for Mady and I. Not so much for elliot but that really doesn't matter.

I had a wonderful time as both Chriss and Amber were intelligent, pretty and polite. We had lovely dinners where the ladies dressed - which kept elliot in his role as lady's maid busy and deeply excited. All that perfect young female flesh to help groom and dress. I kept him in his little cell when he was off duty so he could think about the lovely breasts and pretty pussies he had to tend. Which meant that, after dinner we could talk very freely.

Both girls loved the idea of female dominance and both were intrigued at the idea of female led relationships and, eventually, wife led marriages. But, as Amber asked, "What do we do while we look for the right man?"

They were a bit taken aback when I said, "Have some fun, make some money, become mistresses."

"You mean like dommes?" said Chriss.

"Good Heavens, no," I said laughing. "Too risky, too boring and there is actually an upfront cost to set up a dungeon - which is what men who visit pro-dommes often expect. No, I mean mistresses in the old fashioned sense of the word. A girl kept by a wealthy older man."

"When you go to bed tonight I'll leave Miss Jay's book, Modern Mistress on your tablets," said Mady.

Which she did and both girls read the first fifty or sixty pages in bed.

The next morning we left elliot in his cell and the girls in their pretty nighties (I insist on them wearing white cotton Victorian nighties which matched Mady's) sat around the breakfast table.

"Well, girls," I said, "What did you think?"

"It all sounds great Miss Jay, but, really, in this day and age don't you think it is a little oppressive for a woman to be "kept" by a man?" said Amber...And we were off.

"Not at all," I said. "In fact, if anything, it is a huge first step towards a woman's freedom and, if she chooses, her leadership in her relationships and her marriage."

"How is sleeping with a man for money a step towards freedom?" asked Chriss. Mady smiled having heard this before.

"Chriss, the fact is that money is, in fact, power," I said settling back in my chair and sipping on a very pleasing latte. "When a man gives a woman money he is, in fact, giving her a bit of power. The opportunity to take advantage of a broader array of choices. In exchange, she gives him the pleasure of her company. Escorts have known this since pretty much forever."

"However, escorting, even at the highest end, is essentially transactional. I talk about all that in my book Avails. Lots of girls have escorted but very few of them have really understood how they can make top dollar at minimal risk," I said. "And the biggest problem with escorting is risk. Physical risk, legal risk and, frankly, moral hazard: it is very easy to become very cynical when you sleep with, to use the euphemism, even three or four men a week, much less a night. Cynical girls lose their charm very quickly which is tragic because charm lasts very much longer than youth or beauty."

"Fair enough," said Amber. "Having one man give you money for your company makes more sense but I still can't see how it is particularly liberating. You still pretty much have to sleep with the guy."

"Eventually," I said. "But not until you have made your arrangement. And that arrangement can be very liberating indeed. Have you ever been poor? I mean not knowing where your next meal is coming from poor?"

"Not really," said Amber. "My parents have a bit of money and I can always go home if stuff gets bad."

"I have," said Chriss. "It really sucks."

"And have you ever had more money than you really needed?" I asked. "Money where you could get a blowout and your nails done and buy the dress, the shoes and the bag?"

"All the same day? asked Amber.

"The same day," I replied.

Both girls shook their heads.

"I'm not surprised," I said. "Most young women, even as well educated as the two of you are, don't start earning significant money until they are in their mid-thirties and, realistically, that is usually when they really want to have kids. Soooo."

"A bit of sexual economics. Your "arm candy" years begin at about twenty and end around twenty-five or six. Now, the fact is that women are actually more beautiful in their late twenties and early thirties and if they do it right, keep becoming more interesting as they get older. But a pretty girl commands peak market price for all of six or seven years," I said. "Most girls waste those years looking for Mr. Right or chasing the entry-level jobs they think will create a payoff down the road or going to school. But, mainly, they waste the time because they can't think of what else they might be doing."

"Being kept by a wealthy older man is not a huge time commitment," I continued. "Usually an evening mid-week and, perhaps, a Saturday afternoon."

"No way," said Chriss. "That's what, maybe eight hours a week?"

"At most, dear, at most," I said.

"And you get your rent covered, pretty clothes, spa days," said Amber.

"If you negotiate well, that and lots more," I said. "Remember, the sort of man who keeps a mistress is taking home serious money. He is probably billing out his time at $500+ an hour or running a company or fixing people's teeth. A couple of thousand a month is nothing, 10K and you are beginning to be a noticeable expense. Keep reading Modern Mistress, some of the girls I talked to have really luxurious lives and they tuck money away every month."

"I flipped forward, Miss Jay, and you're right. The girls do make fabulous money sometimes," said Amber. "But how does that make me "free" if I have to put up with some guy old enough, as the saying goes, to be my father being able to have me whenever he wants?"

"Amber, you need to read the whole thing and a few of my extended interviews as well," I said. "No mistress gives her patron unlimited access. That's for escorts, sugar babies and side pieces: a mistress is none of those things nor would a suitable patron ever expect such a thing. And, truth to tell, ladies, past a certain age, most men are simply not that interested in 24/7 sex. They will be delighted to see their mistress once or twice a week."

"OK, but how does even that make me "free"?" asked Amber.

"It makes you better than "free"; it gives you actual power," I said. "Earning an allowance and treats by being a beautiful, intelligent, interested woman lets you do what you want with the rest of your time. Finish a degree, learn to trade stocks, master the PR game but with the sure knowledge that you are not going to miss a meal or be short on rent. Instead of being a "starving student" or an "unpaid intern" struggling to get by with a side gig, a mistress has the luxury of her own time to do what she wants."

"But that depends on a man," said Chriss.

"It does," I replied. "Here's a hint ladies...men want us to depend on them and when we do we take control. As a mistress, you have control of a part of a man's life, as a wife you have the whole thing."

Which I left them with as I had things to do but later that afternoon Amber and Chriss came into my sitting room.

"Miss Jay, do you have a few minutes?" asked Amber.

"Of course...more questions?"

"A few," said Chriss. "We've been reading and talking and, well, ok. How is it fair that to gain any power, girls have to sleep with men who..."

"Stop right there Chriss. Girls always have huge potential power," I said. "The question is will they use it? And if they use it will they use it with any sort of strategy."

"A million years ago I would put on a pretty dress and a nice pair of heels, walk a couple of blocks to a well known steakhouse and, in no more than twenty minutes, be bought a drink or two and, if the gentleman seemed interesting, a very good steak and a bottle of wine. Yes, there were "expectations" but, no, I never felt the slightest obligation. If I was on heat I might well have taken the gentleman home, but not always. And never if I didn't want to. That, of course, was purely tactical. A near term objective as it were. But, and here is the thing, there was an older gentleman who noticed me. He could easily have bought the steakhouse with pocket change. He certainly bought a lot of girls dinner and there was no messing about. Take the dinner you went home with the man. He invited me several times and I declined. He was my first patron."

"Played hard to get," said Amber giggling.

"Not at all. Just hard to get for him. Because I wanted him."

"How could you tell?" asked Chriss.

"When elliot is out of uniform, take a look at his watch. It is one of several but it is my favourite because I gave it to him. It is not a show off's watch, white gold, no diamonds, a Patek Philippe Calatrava. My first patron wore a very similar watch but in 18k gold," I said. "Then shoes, then suit. Now, to be fair, this was when successful men dressed. Now it may be a matter of recognizing a good sweater or the right phone, but the point is the same. Men who have done well have a look. To find them you go to the places they like to go, a couple of bars, a couple of steakhouses, certain sorts of events."

"And you're saying we should not be cynical," said Chriss.

"What's cynical about wanting a very good man who can afford to keep you?" I said. "In fact, for a small, select, minority of women spending a few years as a mistress allows them to reach their full potential. Plus, for a small, select, minority of men, keeping a mistress acknowledges their own proper position as subservient to at least one woman. Even if the acknowledgement is only tacit."

"Really? said Chriss. "I am not sure how being serviced once a week by a girl young enough to be your daughter is exactly subservient."

"Because you are not seeing the whole picture," I said smiling. "First off, he is being "serviced" by a girl who is receiving a significant allowance, is likely living in a nice apartment with good furniture rent free and who, if she has negotiated cleverly, will have a wardrobe and grooming allowance. Second, a mistress, by her nature and position is "in charge" of the time her patron spends with her. She sets the rules, she decides if she will have sex and what sort of sex she'll have. A good mistress is demanding. Her patron has to satisfy her. Which is what keeps him coming back."

"That never seems to be the way it works in my relationships," said Amber.

"Of course not," I said. "You are likely dating and sleeping with boys your own age using the currency of lust and love. Which is wonderful at your age but, frankly, a bit of a waste of your time. I gather neither of you are rushing to find a husband right now."

Both girls shook their head. "Way too soon."

"So, if you decided to take the mistress option one big change you'd make is to move away from the boy/girl sex world of high school. For a mistress, sex and pleasure are part of a fantasy which her patron is buying," I said. "While patrons often think they want their mistress for sex, a clever mistress offers much more than that."

"At the same time, a mistress knows that the best sex a man is ever likely to have is with an enthusiastic, uninhibited, young woman who actually takes charge in the bedroom," I said. "And, of course, that carries right through to a female-led relationship or marriage. For a variety of reasons, even now, men think they have to take the sexual initiative. There is no good reason for that, but there it is. A smart mistress will take matters in hand as it were."

"But why would a man want that?" asked Chriss.

"Two reasons, first the sheer novelty of a pretty young girl having her wicked way with him, second, and more importantly, men take mistresses for the luxury of real relaxation. Most men who can afford a mistress are insanely busy and are making decisions all day," I said. "Knowing that for a few hours a couple of times a week there are no decisions, no real choices, is really what a patron ends up valuing most in his mistress."

"You make that sound so easy, Miss Jay," said Amber. "But, at the end of the day, a patron is still going to want to have sex."

"Indeed. Or at least that's what he thinks he wants," I said. "Men are not very subtle and they are not very good at actually knowing or articulating what they want. In fact, most men want to be listened to, teased a little, seduced and know that, if they do what they are told, the evening will end happily. For a mistress an evening will be about comfort food, a moderate amount of good wine, a sexy - but not slutty - outfit, flowers, candles and enthusiasm. A few evenings like that and a patron will wonder how he ever lived without his mistress."

"The other great benefit of being a mistress, besides the money and the freedom that money brings, is that a girl learns how to manage, take charge of a man," I said. "If I had not been a mistress there is no way I would have been able to give my darling elliot what he so desperately needed. The experience of having a non-romantic, sexual relationship with a strong, successful, man is something every girl should have. But very few girls will because they are content to drift along in peer relationships."

"OK, so let's say I wanted to try being a mistress," said Amber. "Where would I find this wonderful, wealthy, patron?"

"Well, if both of you were looking..."

"We might be," said Chriss.

"Then you'll have a great advantage. One pretty girl is not entirely safe, two and you can take care of each other," I said. "Unfortunately, the nicest way, which is to be introduced by an older lady such as myself, is not really available as I am very much a homebody. However, there is a simple rule: go where the fish are. In the little city you both live in there are, in no particular order, car shows, boat shows, gallery openings, at least one excellent book store and, as I recall, a couple of fairly high end restaurants. It is not difficult to get on the PR lists for openings. And there is nothing at all wrong with a bit of discrete advertising. And don't worry too much about age, there are plenty of men in their late thirties who would love to take a mistress if they had any clue what that was."

Amber looked a bit troubled. "Miss Jay, one thing bothers me about this. A lot of these prospective patrons are married."

"Ideally," I said. "It makes everything much simpler."

"But isn't that cheating?" asked Amber.

"It is. A mistress, however, is a realist. The fact is that men of a certain age and success often cheat. Often with disastrous consequences. A powerful man is surrounded by temptation - personal assistants, work colleagues, vendors, professionals, girls at conferences - the list is endless and involvement with any of them can lead to sexual harassment claims, long hours with the HR department and, of course, the girl falling in love with the man with all that can lead to including a very expensive divorce."

"A smart wife wants to limit her exposure to any of these consequences," I said. "Now most wives will not be lucky enough to have a Mady but, in a sense, they should welcome a young woman who has no long term designs on their husband. Most men are very discrete about their mistresses but women have a sixth sense when it comes to another woman and this poses an intelligence test. If a wife finds out about a mistress what does she do?"

"So, I will tell you one story and then I have to get on with the day. When I was about your age and was being kept by what was known as a "lumber baron", sweet man, I got a call one afternoon from his wife. She introduced herself on the phone as Mrs. X, Ken X's wife and asked if might meet for lunch the following day.

I agreed, what else could I do, and having dressed carefully, went to a very pleasant little restaurant where the maitre d' escorted me to a table where a wonderfully attractive woman of a certain age rose to greet me.

"So you're Hannah. Turn," she said making a little gesture with a perfectly manicured hand. "Oh you are just perfect. Me, thirty years ago. What a pretty dress. Sit down."

"I suppose you wonder how I know about you," said Mrs. X. "Ken has always talked in his sleep. For the last few weeks he has been saying lovely things about a girl named Hannah and two nights ago he actually said, "Time to play with Hannah Jay."

"No..."

"Oh yes. It was perfect, just like Ken." said Mrs. X.

"You seem very relaxed about all this," I said to her.

"Of course, my dear. Ken has worked hard, cut down a lot of trees and treated me and the children beautifully. We are very dear friends, more than a little in love but he's at that age where he realizes the road ahead is shorter than the one behind. That bothers men. A lot. I was worried that you might be a secretary or something but a quick look at the account Ken doesn't think I know about told the story. You're his mistress! Which is wonderful but I thought we should meet. And you should call me Jean."

Quite honestly this was the last thing I expected. I was prepared to be called a hussy and a lot worse. Or for a tearful, "Please don't take my man" scene. But this was extraordinary.

"I'm delighted you approve," I said.

"Approve? My only regret is that I didn't think of the solution myself. You've put a bounce in Ken's step and he's taking things a day at a time rather than brooding over what he is going to do in retirement. But you mustn't tell him," said Jean.

"Tell him what?"

"That I know," said Jean. "I think half the fun of having a mistress is in the sneaking around, the stolen hours. Men love that sort of thing and it would take a lot of the fun out of it if Ken knew I knew and approved."

I laughed out loud. "You know him very well."

"I do," said Jean. "Being married to someone for thirty years has that effect."

"And you really don't mind?"

"Not at all. You are pretty, and nicely built if I may say so, obviously intelligent and on the payroll. Quite seriously, my great worry was that Ken would find some young girl who would think she was in love with him. That can get very messy for everyone," said Jean. "Looking at Ken's account, you are a very practical young woman."

"I've had to be," I said.

"True for most young girls," said Jean. "Now you can have a bit of fun and, if you can keep Ken interested, earn a tidy little nest egg. Something you should know is that Ken absolutely loves giving people presents. Just out of the blue."

"I've noticed that already. Very thoughtful things like a perfect hairbrush and practical things like a dozen pairs of fully fashioned stockings."

"You wear stockings! No wonder Ken enjoys you. I've always worn stockings because Ken loves them but the young girls today, if they wear hose at all, wear those awful pantihose. For a big, rough, lumberjack, Ken is actually quite smart about pretty lingerie and fine leather goods, gloves, shoes, purses, I have a closet full of really beautiful bags he picked out. In fact, maybe that is why he's taken a mistress, I already have everything I want or need."

We had a very good lunch, a bottle of good wine and a nice hug, "Take care of Ken, Hannah. He is a wonderful guy."

"It would make a better story if Jean and I had lunched monthly but we didn't. Ken kept me for a little over two years when I moved to another city," I said. "I missed him for years."

"No wonder you are such a fan of mistresshood," said Amber. "That sounds perfect."

"It was. And, interestingly, it was as a twenty-something mistress that I learned a key fact about successful, wealthy, men; more often than not they need a place in their lives where they are not under stress, don't have to make decisions, can simply do what they are told," I said. "Ken would never have thought of himself as submissive but when he came to my apartment I was completely in charge. And that grew over time. Especially as I found myself enjoying being in charge."

"About twenty years ago, elliot and I were at a party and we ran into Ken and Jean. It was one of those moments which could have gone either way but Ken marched over and said, "Hannah, you must introduce me to your husband". I did and he introduced me to his wife and not another word was said. We were simply old friends who had not seen each other for years. But I did notice that Ken watched how I led, subtly, elliot even in a completely social situation. At the end of the evening, he came back over. "You're a very lucky man, Elliot," was all he said.