Sam meets a Mistress

I was a bit taken aback at the sudden request to get naked, but when I realized I had had half my hand shoved in her dripping pussy just 15 minutes ago, it seemed kind of silly to refuse. So I complied with the request and began to strip. I made no effort to show off or try to make it sensual in any way. Just shucked the clothes and let them drop into a pile on the floor. Considering my chosen form of recreation, I have little body modesty left.

"Shoes too, please"

And I stepped out of the rather conservative low heels I had been wearing and kicked them onto the pile of clothes. She asked me to hold my arms out to the side and proceeded to use the tape to record all my vital measurements right down to my shoe size. I felt she might have spent a little more time than necessary getting my bust measurements and estimating cup size didn't require a hands-on approach. But I didn't mind and was actually enjoying the intimacy of the process.

When she was done with the measurements, she said "The next information I am to collect is of a rather intimate nature. I hope that will be ok. But considering the rather unusual nature of this interview so far, I don't think you will be overly shocked. After all it isn't every day you conduct a job interview where the interviewee practically fists me in the middle of the interview".

I wasn't sure where this was going and this was by far the most detailed anyone had gotten yet before engaging me for my services. I have had requests for clothing sizes before, if the client wanted to have me wear something specific, but nothing like this. Exactly what kind of job was this leading to?

With me still standing naked beside the conference table, Ehri walked over to a low cabinet, which she opened, and removed what appeared to be an oversized briefcase. She brought the case over to the conference table and set it down in front of me. I head the latches pop and saw her make a motion to lift the lid. Then she stepped to the side so I could see what was inside.

I had never seen the like. Inside the case was an array of what appeared to be more than a dozen stainless steel dildos. They were all the same basic shape but varied in size from something 6 inches long and maybe an inch in diameter, to a truly gargantuan specimen that had to be nearly 18 inches long and more than 4 inches thick.

Ehri let me contemplate the sight for a bit before she spoke up saying, "I am tasked with finding out your limits, both vaginally and anally." She did her best to say it matter of factly, like it was a normal thing. I think she was expecting me to immediately object. But to the contrary, I was intrigued and I think I surprised her when I said in an upbeat voice "Let's do it! How would you like to proceed?"

She said, "If you could lay on your back on the table and spread your legs I will take care of the rest. We will start vaginally if that is ok with you."

It was fine with me and I moved over to the heavy conference table, sat on the edge and scooted myself onto the table. I was lying on my back and I spread my legs wide apart, exposing my shaved pussy. I can actually do the splits and I spread wider than was really necessary for what she needed to be able to do.

Her eyes were on my exposed pussy a bit longer than was necessary before she said, "Where should we begin?". I was pretty sure of what I was capable of. Probably two and three quarters inches in diameter and ten inches long in my pussy and somewhat larger in my ass. (Yes, I'm an anal whore, don't judge me).

I pointed into the case and said "Maybe that one.", pointing to one that was about eight inches long and two thick. I knew I could take it but I didn't want the fun to be over too soon.

Ehri crossed back to the cabinet where she had gotten the case and returned with a bottle of lubricant. She applied some to her fingers and squirted a good amount on the tip of the steel phallus she was about to slide into me. She used her fingers to apply the lube to my exposed pussy, including sliding two fingers all the way into me and rolling them around to get me well lubed. The fingers went in easily and I saw her look to the steel dildo. She knew I could take more.

She pulled her fingers out and grabbed the dildo. She positioned the tip of it against the entrance to my pussy and with a slow push, made all eight inches, right up to the flared base, disappear inside me. She held it there for just a few seconds and slowly and smoothly removed it.

She set it off to the side and said "I think we can do better" and she grabbed the next size up. This one was about two and a half inches thick and nine long. This was a good size but still wouldn't be a challenge. She again lubed the steel shaft and positioned it to push into be. This time she went slower, and there was some resistance, I could feel it stretching me a little and felt it when the tip bottomed out inside me. It was a big toy, but certainly manageable and not uncomfortable. She stroked it in and out of me a few times. The heavy steel dildo felt good in me but this seemed to go past the purely clinical examination. I looked up at her and she said "Just making sure it fits", and gave a small smile.

She slid it out of me and reached for the next one. This one was ten inches long and thicker than the last one. Without some additionally stretching this might be near my limit. Ehri again lubed the steel dildo and rubbed a bit more into my pussy. She positioned the head of the shaft against my pussy entrance and said "Ready?". I replied "Yes." and took a deep breath. I felt her begin to apply pressure and could feel my pussy spreading open to take it. She must have felt the resistance and slowed the pressure.

I would call myself a size queen. I love the full stretched feeling of a big toy inside me and this one was stretching me. But it wasn't so bit that I had any doubt about being able to take it. I relaxed, breathed, and focused on the incredible feeling of my pussy being opened wider and wider. Ehri could feel the resistance, but she pushed the toy slow but firmly into me.

I wanted to feel that big, heavy toy inside me and I wanted to show Ehri what I could do. As she applied pressure, I pushed my hips up, to force the toy into me harder and faster. When I pushed, I felt Ehri ease up a bit and I said "No, harder, fuck me!". And she did!

I was scarcely ready when, with a quick hard thrust, she buried the toy half way into my eager cunt. I set out a small groan and my back arched up off the table. But she wasn't done. I felt the toy going deeper and deeper and heard myself saying " Yes, Yes!" as I felt it bottom out. In her clinical vice, I heard her say "Very Good. All 10 inches." And she left the toy in me as she picked up her notebook and jotted down some notes.

She had trouble grabbing the slick base as it was buried up to the hilt in my pussy, but she managed to ease it out of me. This whole episode had me feeling a bit worked up and I was hoping for more. I said "You might need to put it back and double check....a few times." But she replied that that was outside her instructions and she didn't want to displease Mistress Angela. I did my best pout and spread my legs even wider, almost into a full splits. Her eyes were on my spread pussy, but she was shaking her head no.

After takin in the sight for several seconds she asked, "Are you ready to proceed?" I was still disappointed, but just said "If we must". After the dildo exercise, I was pretty sure what was next and I waited for instructions. She said "Please stand and lean across the table as I did before. Legs apart as is comfortable.

I slid off the table, leafing not an inconsiderable amount of wetness (Not my problem to clean up), and stood, turned and assumed a position similar to what Ehri had when I amused myself with her ass. The only difference is that I am taller and had to spread my legs a bit wider to fully lay down on the table.

As I was getting into position, Ehri was putting away the steel dildo collection and then returned with a second case, smaller than the one that had contained the dildos. I had assumed the dildos would also be used to measure how much I could take in my ass, but apparently I was in store for something new. The case what out of my eyeline as she opened it, but based on how the encounter had gone so far, I wasn't overly concerned.

I sensed Ehri moving up behind me, between my legs. She said "Now I am to measure your sphincter dilation ability. I am to test your limits, so there may be some discomfort. If there is any problem or you need me to stop, say 'slow' or 'stop' and I will do as instructed."

The lube was a little cool on my veteran hole, but not cold. She applied it generously and I felt a slippery finger or two push their way into my ass. She worked them around a bit more than was probably required but I certainly didn't complain. Maybe she felt this was within the limits of her instructions.

I felt her fingers slide out of me and something hard and cool slide in. Whatever it was wasn't very big, at least not by my standards and I assumed it was made of stainless steel like the dildos. Ehri asked "Are you ready?". Since I didn't know what was happening, I just went with it, nodded my head and said "Lets do it." I closed my eyes and tried to relax.

The first click came as a bit of a surprise as it wasn't a sound I had expected to hear. The shock of the sound had almost cause me not to notice that my asshole had been force slightly open. There was another click, my ass opened a bit more and then I got it. It was some kind of mechanical device to stretch me open. Now I was interested. Was this something Mistress Angela had custom made. I had never experienced anything like it. And there was another click followed by my ass being opened wider. I have to say, it was a strange sensation. Normally when my ass is being opened like this, there is something solid filling me. In this case, my ass was open, but there was none of that filling sensation you get with a dildo or plug. I'm not saying it was bad, just very, very different.

Then there was another click and another and another, and I was starting to feel a bit of a stretch now. I'm not sure how wide I had been opened already, but I could take a fair amount more. I was trying to keep count of the clicks and I thought I was up to 5. Then I had another thought, Ehri could see all the way up inside me.

My ass gapes after a vigorous workout but that usually only last a very short while and the gape is pretty small since there is nothing holding it open. But in this case, I am wide open and staying that way. I really wanted to know what my ass looked like right at this moment.

More clicks, and now I was feeling the stretch. I think I was up to 8 or 9 clicks. It wasn't painful, and I estimated my ass was probably spread nearly 3 inches, but the clinical nature of the examination and the lack of penetration did not provide the same pleasure as a big, thick dildo. And I needed the pleasure to really let myself be pushed. You can take a lot more pain if there is a good amount of pleasure mixed in.

A click, and another.

That last click was a bit uncomfortable. Still not what I would call painful, but I must have moved a bit because Ehri asked, "Are you alright?". I nodded my head but she said, "I need you to answer verbally that you are ok to continue." I said "Proceed", and there was another click.

Now it was definitely uncomfortable, but I had something to prove and said "One more, I can do one more." The click was slow in coming and I felt the increasing pressure as I was stretched even further. There was the first twinge of pain, but I could handle it. Slow breaths, controlled breathing, give the muscles time to adjust.

After half a dozen slow breaths, I could manage to say, "I think that all I can do."

Ehri replied "I am impressed. I have never done 13. Maybe its will be a lucky number for you."

She moved up beside my left hip, on hand on my left ass cheek and leaned in toward my ear and whispered, "I will get the dilator out of you but can I take a liberty with you first?". My ass was becoming more used to its gaping position and I thought, why not.

I said with just the slightest bit of strain in my voice, "After the intimacies of the last hour I don't think you need to ask".

She said "Promise you wont tell Mistress?"

To which I replied "I promise."

I felt her slide her hand along the curve of my ass, and though maybe she had changed her mind about whatever it was she had wanted to do. I was sure whatever she had in mind was against her Mistresses instructions.

She took her hand off my ass and I didn't feel anything for a moment. I thought she is probably getting ready to do whatever is necessary to release the dilator. But then I felt it. Deep in me. Her hand inside me. She was fisting me! Or at least her hand was inside my widely gaping ass. The sensation was strange. Not like I was used to being fisted in my ass (which happens a fair amount), but it was inside me, it felt almost alien.

And then it was over, she had withdrawn her hand and I was left a bit confused over how I had felt about it. It was just so different a sensation. I think this is something to be explored later. But for now I felt the dilator relax and the pressure taken off my stretched rear entry.

Ehri said "That's the end of the examination. There is a restroom through that door if you need to clean up. And just so you know, I don't know anybody else who has taken 13." This surprised me a bit as I felt I could have done one or maybe even two more with the right motivation. But for now I just smiled and felt a little pride.

I headed to the bathroom and cleaned up a bit, removing most of the generous amount of lube on my privates and doing my best to make sure I looked presentable for my walk back to my car. Ten minutes later I returned to the conference room where Ehri was seated in one of the leather chairs.

She said, "Please come sit a minute. The exam is over, but there is still a bit of business."

I took a seat beside her and she said, Please open the large envelope labeled number 1 and review its contents."

I reached across the table to where the envelopes had been left. I opened the envelope marked "1" and took out the approximately 50 pages contained therein. A quick scan of the first page sent my heart racing. Right there at the top of the page was my name, my real name. Followed by my real address and the subsequent pages contained my college transcripts, a summary of my real estate and stock holdings, and it went on and on. Before I was even half way through it I stood and practically ran toward the door. But when I got there, I found it locked. I looked for something to smash into the door so I could get out, escape before I found out just how much they knew.

As I turned to reach for a chair to try to use as a battering ram, two things happened almost simultaneously. Ehri said "I'm Sorry" and an authoritative voice said "Please sit down and allow me to explain."

A woman's face appeared on the screens at the end of the room. She appeared to maybe be in her fifties or maybe even well maintained sixties. She wasn't beautiful, but she was striking. She had an angular face with Slavic features and intense piercing eyes. Her hair was gray. Not the gray of age, but the gray of experience and strength. The gray of cold steel.

I stopped trying to break down the doors, but I didn't move back to the table. I felt staying near the only exit I knew was the best option.

The face on the screen said, "Allow me to introduce myself. You will call me Mistress Angela....assuming we ever see each other again after today. I apologize for invading the privacy you have worked so hard to maintain. But you can't deny that I have the right to try to protect my public life from my private life much as you do. I have no interest in exposing your secrets. Quite to the contrary, your ability to keep a secret is what brought us together. Most woman I use for my entertainment can be bought. But I still have to be careful. I don't tolerate blackmail and trust me, some have tried. But the kind of money I have buys a lot of lawyers. And if the lawyers don't work, there are other ways. But with you, you have as much reason to keep secrets as I do. However, that only applies if you know that I know who you really are. We both have the power and resources to reveal secrets, but I don't think either of us wants that."

I took a few steps back toward the chair I had been seated in and she went on, "I was watching your meeting with Ehri and I can tell you want what I have to offer. Essentially, I want to hire you for the services which you have already been providing. While there is a certain appeal to luring a novice. There are some things they just can't be taught in a reasonable amount of time; like taking a good fisting and wanting more.

Then the face on the screen turned toward where Ehri sat and said, "Don't think I didn't see that little unauthorized indiscretion. We will talk about that later."

Then back to me, "I want to hire you for a full week. During that week you will make yourself available to myself and any others I chose to share you with. For that week, you will essentially be my property. I literal slave to my whims. "

Even though I hadn't said it yet, I knew I was hooked. I stood there for a minute, then two, staring into those intense eyes. The I nodded my head and said, "I have a few conditions."

I sat back down and we got to the business of negotiating details. The second sealed envelope was a legal contract, with surprisingly specific language. I wondered what the legal secretary had thought who had typed up phrases like......'all dildos, plugs or other objects inserted anally, vaginally, or orally shall be of body safe materials'. But with her money and influence, maybe the lawyer who drafted it was well aware of her interests, or maybe even participated.

In principle, I agreed with the contents, but asked for, and was granted, a few days to review it.

A week later I sent the signed contract back to Ehri.