The Demanding Duchess

So, because my marriage was dull and my wife refused to talk about how to improve things in the bedroom, I posted on one of those sex/dating sites that I was looking for a mature lady, 50 plus, preferably a widow, divorcee, or some version of single, hopefully upper middle class, who needed a man for discreet, special, and intimate encounters. As I saw it, she'd be solving a need that only she and her prospective partner knew possessed her. And since I was living in one of the most upper crust communities in the northeastern United States, I figured she was around. It was just a matter of finding her.

Of course, she wasn't about to discuss her needs with anyone, not even with those closest to her, whether a friend or family member or, potentially, someone who worked for her. And the demands she would make on someone providing this service could be extraordinary, anything from a contract to mentioning she knew people who knew people who could bring about their silence -- forever!

Nearly eight months after posting my ad there was a reply.

"Young man," she wrote, "I'm likely the one you seek. But before we meet, you'll need to tell me more about you. What do you look like? What's your social background? And what about your education? Finally, do you know how to mind your manners at the dinner table?"

I was both excited and yet worried I could easily misstep in my response.

After mentioning I was married with children, employed, and held a graduate degree and had traveled across Europe and parts of Asia, she asked a question I never expected -- where did I live? This bothered me. Discretion is discretion I figured but this worried me. It would be giving away far too much information.

"Young man," she wrote after not hearing from me soon enough, "I need to know where you're coming from and that your social situation is, well, similar to mine. It sounds like much of it is. But, of course, your answer remains incomplete."

In other words, if she was going to move forward, she demanded to know where I lived. There was no other choice. Answer her -- or else!

So, with great fear and reluctance, I told her.

"Good," she replied. "And, by the way, what's your address."

This, too, was more than I bargained for but, again, she was saying, in so many words, cough it up -- or else!

As it turned out, she was a few towns over, in one that likely had a GDP larger than most small countries.

The following day, she made another demand: She wanted a picture -- clothed, one that showed me looking professional.

Again, I hesitated. But, as I did previously, I thought either the goods are delivered or this ends. I asked her for a couple of days, when I could take the picture discreetly. That was fine, she said. "Just deliver what I require," she added.

Forty-eight hours later, after my wife had taken the kids for a weekend playdate, I sent off a picture. I was in two-piece suit, a white shirt and red necktie.

I passed.

"Of course," she continued, "you won't be receiving a picture of me. But you're passing muster so we should figure out a time to meet. What do either late mornings, around 10:30 or early afternoons, around 1:30, look like for you? Are you available?"

Since I was an independent contractor and my wife worked in the city, and the kids were in school and daycare, it would be fairly easy for me to get away. Finally, we settled that I would show up at 10:30 on a Tuesday morning -- "for coffee," she stated.

The anointed day arrived. After returning from dropping the kids to school, I dressed as I did in the picture I sent. While driving over, I was more nervous than the first time I had sex. I worried about her looks -- was she rundown, old and ugly? -- and how big her dwelling was. Would she have staff? Would my Toyota Highlander make me look as if I hailed from the dregs of society?

Finally, I found her place. It was 10,000 square foot mansion, tucked into a very quiet neighborhood, behind a gated, eight-foot wall. One had to press '0' and announce their arrival in the voice box before the gate was opened.

After pulling up in the circled driveway, I parked, got out, put on my suit jacket, and went to the front door. Soon the butler was escorting me across a white marbled floor, past the living room, then the dining room before remarking that I was to wait in the library. It was small, carpeted, with a wall of shelves filled with books. The furniture included a loveseat, four wingback chairs, and two tables. Clearly, this was a place for a discreet talk, whether it was finances, prospective marriage partners, the future or anything else that needed to be kept, well, off the record, discreet. In silence!

I was directed to sit down in one of the wingbacks across from the loveseat before being asked how I took my coffee. Madam would be with me shortly, the butler mentioned. This was a job interview.

Elsa soon arrived. The first thing I noticed was that she was very well preserved. She walked with determination and was in a blue blouse and long skirt that went to her ankles. She was about 5'5" with gray hair that covered her ears, appearing to be in her mid-70s, and weighing around 160 lbs., I guessed.

"Good morning," she said with a smile as she entered.

I stood up, replying, "Good morning," as she insisted I remain seated, while briefly shaking my hand.

"It's nice to meet you," she said.

"Likewise, a pleasure."

"So, tell me," she inquired, with a hint of an English accent, while sitting down, "How long have you been on this search?"

"Well, that was the first post I ever made," I said.

"Really? The way it was written I figured you would have put it up there numerous times. But, perhaps, that's due to my not being entirely familiar with the internet."

"That was the only time I put it up there," I said. "I mean I did need to renew it, of course, but it was up there for almost nine months before you replied."

"I see," she said as the butler entered the room with two cups of coffee. After placing the cups on the table between us, she started talking again.

"You know," she continued, "something like this needs to be kept highly confidential. And I would think that would suit your purposes, too."

"Elsa, you're taking a huge risk, and I am, too. I'm not here to ruin your life, your stature, and what I've noticed about our notes -- emails -- is that you're not out to ruin mine. Still, it would seem that we have both have needs that aren't being met."

"Oh, you're quite right about that," she said. "My husband died more than a decade ago. Of course, my sons and daughters, the grandchildren, think I'm some sort of nun. I did really love my husband but the idea of a partner, someone, who could spend time with me on occasion has a certain appeal."

"Good to know," I said.

"But tell me," she inquired, "how much of a commitment are you prepared to make? Something like this, where we're well, in a compromising position, to say the least, can't be a one-time thing. At least not for me."

"Of course it can't. This needs to be a long-term arrangement. But conducted in silence. Discreet. No one knows -- ever. Taken to the grave."

"That's reassuring," she said before warning, "But, of course, you can't be with others if you're going to be with me."

I was just about to answer, when she said, "Of course, I know you're married, and you have those obligations. But you can't be with anyone else other than your wife if you're also going to be with me."

"Elsa, if this works out, I'm with you only. Other than my family obligations."

"Good," she stated smiling. "My late husband a few affairs, but I always found out about them. Some women do not know how to keep their mouths shut. This one does. And, of course, it sounds like you do, too."

"I do," I said.

"So," she continued, "have you done this often?"

"There was one other woman -- years ago. But she moved after her divorce."

"Oh, did her husband find out about you?"

"Nothing like that. It her second marriage and as she described it, there wasn't much left to it after 15 years. She left for Savannah."

"I see," Elsa remarked.

There was a brief silence between us before she broke it.

"So, intimately speaking, what is it you enjoy?"

There was no messing with Elsa. She was almost like Queen Victoria. She crossed every 't' and dotted every 'I' -- and asked every question! -- before signing a contract. She was the family's matriarch, and it was old, long-established blueblood family. For lack of a better description, I was being vetted as her consort, and the discreet one at that, one who could be easily disposed.

I went through what I enjoyed sexually, and she nodded.

"I see," she said. "And can you imagine doing those things with me?"

"Yes," I said without hesitation.

"And why do you say that? I mean, we barely know each other. You haven't seen me in a bathing suit or in any kind of intimate clothing. I must look like your grandmother.

"Well," I stumbled somewhat, "you're not my grandmother. And we wouldn't have exchanged those emails or be having this meeting unless you were interested. You're in charge here. That's very clear."

"You've got that right, young man," she said with a smile. "Do you have any questions for me?"

"Sure. I mean, does this really interest you? Do you have the time for this sort of thing? And what do you enjoy, intimately speaking, of course?"

"Well, kissing is critical. My breasts and clitoris are all very sensitive and require attention, of course. You might be surprised by some of my physical attributes. And I hope you're not turned off by them."

"What could possibly be wrong about you? You're very attractive, quite beautiful even."

"Things aren't always the way they seem. Age has a way of catching up. But long before there was age, there was just how I am."

"I see," I said.

"We can go through it later," she added.

There was another silent interlude before asked, "How much time do you have?"

"I'm good for about another hour or so," I said.

"Good. Well do follow me," she said, as she got up from the loveseat.

We went back toward the front of the house, near the living room, toward the center stairwell. She asked me to remove my shoes -- "Oh, they'll be shined before you leave" -- and to follow her upstairs.

We soon entered an oversize bathroom in the hall. It included two sinks, a tub, a separate shower that could hold three people, and, off to the side, behind a door, the toilet. She told me to close the door behind me. I did as instructed before turning to face her.

"So, young man, I'll need to know what you're all about before anything happens."

"Of course," I said, worried what was next.

"Can you please remove your jacket? I'll hang it up for you."

I did as she said, and she looked me over after hanging it up on the door's hook.

"Nice tie, by the way," she said while staring at me before saying, "Remove it and your shirt."

Soon came the next instruction.

"You'll need to do me another favor," she said.

"Of course."

"Remove your pants -- and underwear. I need to know what you have."

Hers was a thorough vetting, I thought, before unbuckling my pants and pulling them down and off along with my underwear.

Before long, I was standing there in the middle of the bathroom nude.

She looked me over and over before saying, "Turn around."

I did as I was told.

"Bend over, grab your buttocks and spread them apart," she said next.

In the mirror, I saw her nodding in approval before telling me to turn back to face her.

Then she came up to me and held my penis. It grew long and hard in her soft hand.

"Well," she said, still looking and holding it, "that's a very nice one you have."

"Thank you."

"Do like it when I rub it," she asked while moving her palm and fingers across my penis.

"Yes, of course."

After a few minutes, she said, "Pardon me," before heading into the bedroom.

A number of minutes passed -- maybe 10 -- before she returned to the bathroom in a long white robe.

"Now come up to me and pull my robe apart so you can see me."

Again, I did as instructed. Her breasts were small but nice. Her stomach carried a few pounds, and her vagina was covered in pubic hair. Still, I thought she was quite beautiful. And if I didn't think so, my dick certainly showed its approval.

"Uh, you look great," I said. "I mean you're very, very attractive. Quite beautiful. I can imagine making love to you."

"Well, that's wonderful and quite the relief. But there's still one more thing we should take into consideration.

"What's that?" I asked.

"Come with me," she said, as she entered the bedroom and sat on the bed.

"I want to take a look at this," she said while lying back on the bed, and pointing to her vagina.

"I want to you take a close look at my clitoris."

"Uh, okay," I said. "But if you don't mind my asking, why is this so important?"

"You'll know soon enough," she said before telling me to get on my knees.

After spreading her legs apart, she said, "Touch my vagina very gently and feel my clitoris."

I did as I was told and, before long, noticed that hers was larger than average, more than an inch in length when erect.

"Well, it all looks great to me," I said. "You're terrific. Very beautiful."

"You're not embarrassed or turned off by it," she said.

"No."

"Good to know. My husband always thought it was another penis and, well, it caused a few issues."

"Well, it's not a problem for me. I'm here to make you happy."

"Well, you're going to need to suck it," she said, "for me to have any sort of satisfaction. And you'll also need to stroke it with your fingers."

"No problem. I'm happy too."

"Then get to work," she demanded.