Despair?

Despair is too strong a word for how I am feeling.  But I am upset.  I've just now discovered that a man with whom I had a brief S/M liason, passed away in 2009.  I was required to call him "Master Ian."  I had met him after his wife, "Mistress Helen" interviewed me over the telephone.  "Have you ever been buggered?" she stated.  She spoke with a kind of distainful authority.  I met the pair at a tea room in the Peninsula Hotel in New York.  I brought with me and off-white apron, as I'd been instructed.  I wore a charcoal grey suit.  Underneath I wore stockings, as Ian had required of me.  We sat down around a knee high coffee table surrounded by three plush seats.  Ian instructed me to raise my trouser cuff, allowing him to see my stocking'd leg.  Ian was a distinguished man in an elegant suit.  Helen was Asian.  She was attractive.  Ian spoke with a Scottish accent.  A server approached the table and took our order.  Ian spoke, ordering for both he and Helen.  "And for the gentleman?" the server asked.  Ian piped up, "He's having nothing."

The place was filled with people.  We spoke in hushed tones.  He asked me about my life and my intentions for the future.  He wanted a sissy girl slave who would live near him in my own apartment, but would be available to him upon request.  He stated that he was renaming me Kimberly, and that's how he and Helen addressed me from then on.  All of this excited me very much.  I had never seen a dominant couple who appeared to actually live the lifestyle.  Ian told me that he worked for the U.N. in some diplomatic capacity.  I told him I was from Los Angeles.  He asked me who I knew in Los Angeles.  When I told him that I did not socialize with the entertainment society, he stated that he only knew industry people in Los Angeles.

Ian stood up and commanded that I accompany him to the bathroom.  He had me enter a stall and place my hands against the back wall over the toilet.  He pulled down my trousers and started massaging my genitalia.  Then he grabbed me hard, making me recoil and twist from the pain.  As someone entered the bathroom, and we waited for them to leave.  He again was molesting me.  The door to the restroom opened again.  "God.  It's like Grand Central Station in here."  We returned to table.

"I will own you, if you're lucky," he stated to me plainly.  He was firm.  His demeanor seemed angry.  I would transform, completely.  My male self was to be crushed out of me until only a feminine shell remained.  It seemed a bit preposterous to me at the thime.  They finished their tea and we prepared to leave.  Ian handed me a sports bag for me to carry, out of which poked a heavy riding crop hidden within a plastic bag.  Ian ordered that I walk behind them at 10 paces. 

We travelled by subway to Queens, arriving at a quite empty apartment that had been cleaned in preparation for moving.  There was little furnature.  The place was to be sold by Helen.  I was informed that she was moving in with Ian and that she was selling her place.  Ian instructed me to strip naked, and put the apron on.  I was ordered to go clean the bathroom, and to pay particular attention to cleaning the toilet.  I worked hard cleaning the already spotless, empty bathroom.  I began to perspire from the futile task.  Ian came to inspect my work.  He held the riding crop, like some Nazi Gestopo Officer.  It seemed rather silly to me, the whole ritual of cleaning an already spotless bathroom.  He ran his fingers over the medicine cabinet, and inspected the toilet.  He ran his fingers over the top frame of the toilet paper dispenser that was built into the wall.  He inspected his finger, and apparently finding it unclean, ordered me to open my mouth, into which he inserted the finger.  He ordered me to suck the finger clean, which I did.  He ordered me into the empty living room, where I was told to kneel.  I got down on all fours.  "Put your cheek on the ground," he commanded.  I placed my face down on the dark hardwood floor.  My ass was in the air.  Helen stood near me.

Ian hit my ass profoundly hard with the riding crop.  He wasn't playing.  One.  Two.  Three, strikes he hit me.  I rose up in agony.  "Get down or double the punishment," he yelled.  I got down.  This was not what I had expected.  Another three hard thwats.  He was a grown man giving it to me with all his strength.  "When I tell you to do something, you damn well do it," he stated.  I looked up at him.  "Get your eyes off of me," he commanded, "Don't ever look me in the eye.  Cast your eyes down."  I did as I was instructed.  He put the end of the riding crop under my penis and lifted it, saying something at a "clitty."

Ian then ordered Helen to bend over.  She angled her bottom toward him.  He face had a expression of disregard.  He ceremoniously put the cane to her three times.  She straightened herself, unmoved.  She had been "punished" for my misdeed.  That was the chain of command.  Ian, Helen, and then me.

We travelled back to Manhattan.  We went to a restaurant, that I barely recollect.  I was allowed to speak with a bit more freedom.  When the server approached, Ian ordered for both me and Helen.  He assigned me homework at dinner.  I was to prepare some large number of cards...maybe a hundred.  I don't recall.  I was to apply lipstick, kis the card, and write a mantra.  I don't recall the words, except that it was to end with the word "sissykins." 

I had not expected to be spending so much time in this adventure.  I was getting a bit nervous.  Was I going into slavery now?  This was the first time I met them.  What I thought was to be an interview had turned into an already long day.  It was getting late, and I didn't know when/if I would be excused.

We left the restraunt and Ian chastened me for not helping Helen on with her green overcoat.  He came at me like he was about to him me.  I cringed.  When I understood my transgression, I immediately took possession of her overcoat off the hook and helped her on with it.  It felt kind of good to be so out of control, and always on edge.  I knew by now that any little trangressions could be handled quite brutally.

We started off, to what I came to realize was Ian's apartment building.  It was in an elegant location, that in my years in New York, did not know.  I don't know if I could find it today.  I was instructed to enter the building after them, and make it appear that we were not together.  He appeared a tad concerned that his personally life could bleed into his professional world.  Into the elevator and up and up and up, until we reached a point with a very nice view.  I cannot recall what happened there, except that I was now his property and that I was about to be excused (for which I was profoundly grateful).  Before I left though, I was gain ordered to strip down.  He put me on my knees in the kitchen area, where there was no carpet.  He informed me that, although there would be occassions that I would be sharing their bed, I would never be allowed to penetrate Helen.  It hadn't crossed my mind really.  I, on the otherhand, would be penetrated.  He ordered Helen into her room to put on high heels.  "You won't be allowed to have any other relationships, either.  If you want children, maybe I can find a dominant woman for you to marry."  Helen returned, wearing blue pumps.  She positioned herself in front of me, and stuck a feminine pose with her shoes, one foot catty corner from the other.  Ian ordered me to masturbate and ejaculate onto the kitchen floor.  I knew where this was going.  I suspected that he would have me lick the cum off the floor.

I was physically unable to reach climax, mostly because I was profoundly nervous.  After an uncomfortable effort on my part to inseminate the lenolium, Ian asked me what was going on.  I told him that I couldn't.  He seemed resigned, and allowed me to get dressed.  I don't recall his parting words that evening, but I left that building dazed.  It had been a profoundly long day.