The Personal Assistant

"Please Sam, I have been naked more than I've been dressed today."

I had to laugh at that. But I was determined not to tolerate her disobedience. I wanted her under my thumb completely, no matter how many times I had to strip her in my office. And this time she was really going to understand about consequences.

"Strip," I ordered, pushing her away. "Show me some of that new expensive underware."

Vickie looked stricken. She was sobbing softly as she slowly began removing her clothes. I was surprised to see that she was still naked under her skirt and camisole.

"You are such a slut," I said.

"Ginger would not let me wear the new things out of the store," she whimpered.

"No matter. You can put some on when I am finished with you."

In another minute she was in her stockings and heels and nothing else, clearly apprehensive as I looked her over with fire in my eyes. "Go over to the credenza and pick one of the paddles. You have a choice of a wooden one, or a leather one. And don't bend your knees when you are looking for them."

I have always found it very satisfying to make your victim bring you the instrument of their punishment. It adds to their humiliation and submission. In this case it had the added benefit of requiring Vickie to bend over with her ass in the air as she searched in the low cabinet.

My collection of sex toys includes two special paddles that I had purchased on line from 'Adam and Gillian's' website. One was solid oak in the shape of an enlarged ping pong paddle. The other was basically a short leather strap attached to a wooden handle. Numerous holes the size of a quarter were located throughout the strap. Vickie wisely chose this one, knowing that the flexibility would lessen the pain.

"Go stand by the window," I ordered, "down at the end."

My office is on a corner of the building, high up, with large windows on two sides. There are metal slat curtains that can be closed to keep out the sun, but that day the curtains were pulled to the sides. The windows go almost all the way to the floor, except for a radiator grill that runs along the base, about a foot high. It was summertime, and the radiators were off.

"Face the end window, bend over, and put your hands on top of the radiator. Don't move your hands, no matter what."

Vickie was resigned to her fate and did as I instructed. Her ass came up and presented a perfect target. At the same time her big tits hung below her, swinging slowly back and forth as she squirmed in anticipation. Her position in the windows exposed her profile on one side and her tearful face on the other. I wondered if any of my neighbors in the adjoining skyscrapers would be watching.

SLAPPP.... My first swing of the leather paddle caught her squarely in the middle of her ass. It was a hard spank that I knew would get her attention.

"OHHH..... THAT REALLY HURT....."

"It was supposed to. Now listen to me. The length and severity of your punishment will depend on how well you take it and your attitude. You are not to move or resist. If necessary I can tie you to the window with the cords on the curtains."

"Yes sir...."

Before resuming I teased the reddened skin on her ass with my fingernails. Then I began a systematic spanking of her ass cheeks and upper thighs—not too hard, but with enough force so that each blow stung sharply.

SLaap... Whapp.... Slapp... WHAAP... SLAPP.......

"Ohhhh.... goddddd..... ahhhh.... whaaaaa......" Vickie cried and twisted and squirmed, but she held her position.

I paused. "What are you learning?"

"OHHH... I am learning to do what you tell me... I promise.... I have learned."

"Spread your legs." She did and my hand dipped to feel her wetness. "I think your lesson needs reinforcement."

Just then my cell phone started vibrating in my pocket. I retrieved it with my free hand, while with the other I maneuvered the smooth leather of the paddle around between her legs. She moaned.

"Hello," I said into the phone. The caller was a friend of mine whose office was on the same floor in the building next door. He told me he was enjoying the show I was putting on in my window. It was a good opportunity to increase Vickie's humiliation.

"Yes Charlie. I'm glad you happen to be looking out your window. I have this new personal assistant who needs to be taught the importance of obedience."

Charlie and I had similar tastes and had often partied together. From the tone of his voice I knew he was excited by the idea that I had a new employee who could be abused in this way. He was hoping to be invited to participate. I egged him on to further torment Vickie.

"By all means, Charlie. Have your secretary bring your binoculars. I am not through yet. What's that? You want me to spank those hanging tits? But Charlie, that would hurt terribly, don't you think?"

Now Vickie was really squirming. She knew how vulnerable her tits were in her position. I teased her by tapping them with the paddle and letting a nipple stick through one of the holes in the leather. By moving the paddle sideways I could agitate her nipple against the lining of the hole.

"OH GOD Sam... I'll be good....I really will.....please don't do this to me in the window in front of the whole world....."

I ignored her and continued my conversation with Charlie. "Charlie, why don't you call Phil and tell him what's going on? His office is directly under yours and he could see just as well..... okay, bye for now, we'll get together soon."

Vickie clearly had not learned her lesson. She persisted in telling me what she wanted and didn't want. It was going to take many sessions for her to realize that she should be concerned only for my pleasure. If I wanted to show her off in the window, she should not protest. The fact that she did gave me an excuse to punish her more, and do it in front of Charlie and Phil, and who knows who else. At the very least, Charlie's secretary was watching.

Chapter 14 – Vickie

Why had I rebuffed Ginger's advances? That was stupid. I should have known she would be like Karen and tell Sam everything. Sooner or later I was going to have to submit to a woman anyway. I had brought this punishment on myself.

Overhearing the phone conversation and knowing I was being watched by both men and women was so embarrassing. And any hope that my spanking would end soon was dashed with Sam's next words.

"So you don't like being put in the window. Too bad. Now that I know we have an audience, I think we should give them a better show. Stand up and face the glass."

Before I knew it Sam had raised my arms and tied my wrists to the curtain cords on either side of the big pane of glass. "Now spread your legs and press your toes into the vents in the radiator grill. That's it. Perfect."

I was stretched in front of the window like an animal skin, facing outside for all to see. Except for my stockings and heels I was completely naked. Sam pushed me in the back and my tits flattened against the cool glass. Looking down I could see little figures on the sidewalk. I was terrified of falling through the glass.

"Sam, please let me down..... I'm scared of crashing through the window."

His answer was to rain a series of hard slaps on my ass with the leather paddle. Every time I knew one was coming I tried to lessen the sting by pushing my hips forward, which of course pressed me against the window.

"Ohhhh..... arrrrrwww......"

"Did I not tell you before you accepted this job that any disobedience would be dealt with swiftly and painfully?"

"Yes Sir... I am sorry Sir...."

"You are now going to get twenty spanks, and you are to count each one and thank me for correcting you."

SMACK

"One.... thank you Sir."

SMACK

"Two... thank you Sir."

I kept up the count and tried not to press against the glass. My stomach was churning from looking down from that dizzying height. After the tenth spank I clenched my eyes tightly shut. I was trembling.

Sam would not have it. "Open your eyes, Vickie. Look at the buildings across the way and see if you see anyone watching you."

Looking up I could see groups of people at several of the windows in the closest building. "Ohh.. nooooo...."

"You like it Vickie. Your nipples are hard as rocks, and your pussy has smeared stuff all over the glass."

It was true. I was turned on by the whole scene. As I counted out the remaining spanks I realized I was close to orgasm. If Sam had put that leather up between my legs it would have been all over. But he stopped and whispered in my ear.

"Are you ready to abide by the rules of your employment?"

"Yes Sir. I will do anything and everything that you want. Just please let me get away from this window. I am so dizzy."

"OK, I will untie you. But the first thing you have to do is clean my window... using your tongue."

Oh, the humiliation! Sam kept coming up with things to degrade me. Why was it that with each new abomination I felt a fresh wave of excitement? He released my wrists, and I bent over to put my mouth on the glass where I had wet it with my juices. The view looking down sent adrenalin rushing through my veins. I closed my eyes and licked.

"Good girl," he said as he patted my sore ass like I was his pet dog.

Chapter 15 – Sam

Spanking Vickie in the window was very exciting, and I was ready to lay her out on my desk and fuck her again. But there was work to be done. I couldn't spend the entire day playing.

"That's enough. You can get dressed now. And put on some underware for god's sake. You now have to become a normal office worker and get busy making arrangements for George Stockwell's visit."

"My new undies are still my car," she whined.

"Well," I laughed, "you can get them when you go to lunch. In the meantime put your clothes back on so I can think about something other than fucking you."

"Yes Sir," she said and hurried to pick up her clothes from the floor. I noted how glad she was to be away from the window. Since she was so uncomfortable there, it would be a good place to discipline her in the future.

I sat at my desk and watched her put on her clothes. As she covered herself her confidence seemed to return. Her expression changed from one of defeated resignation to one that said she could take whatever I dished out. I was pleased that she was not a push over; it made it more fun to train her.

When she was fully dressed I held out a file for her to take. "Here is the information on a yacht rental service. Stockwell will be here on Friday. Make arrangements for a two night private cruise. The ship should have a full crew and at least four staterooms. You should make sure that one of the crew is young, pretty, and willing... if you know what I mean."

She didn't bat an eye. "I understand. Will I be going on the cruise too?"

"Yes. I told you that you would be the hostess. You will be there and on call to make sure everything goes smoothly. You and I will share a stateroom."

"What kinds of activities does Mr. Stockwell like? Should I arrange for fishing, or scuba diving?"

I laughed. "Stockwell likes to eat, drink, and fuck. But I don't know about his new wife. You should be prepared for everything and anything."

"How do I make a deposit to secure the yacht rental?

"Take this credit card. It's good up to $10,000. The full price will be more than that, and when you need to pay give me the details so I can do a bank transfer."

"Okay boss," she said with a smile. "Do I have a desk and phone somewhere?"

"Of course, right next door. Turn left down the hall and it's the first door on your right. You even have your own private bathroom."

Vickie took the folder and exited my office, swinging her hips ever so slightly. "Classy," she said as she went out the door. I detected a little sauciness in her tone and smiled. It would be more fun breaking her if she was a bit feisty.

Chapter 16 – Vickie

I was mortified to have to lick the window clean. When Sam patted my ass like I was his pet dog and said "good girl" I swear I could have just exploded right then. Why oh why am I so turned on by all this humiliation? I was glad when Sam told me to get dressed and I could finally get down to some work. A warm rush had surged through my body when Sam said I would be staying in his cabin with him. Maybe he would treat me more as an equal if we were sleeping together.

Even though I know Sam is enjoying what he does to me and at times so am I, I just can't help thinking that all this is wrong. His touch and the touch of the paddle and crop excite me so much, but my mind still is awash in conflicting emotions. I wish I had someone I could talk to about all this, but I would be too ashamed and embarrassed.

My office was small and had no window, but it was adequate, and at least it gave me some privacy. After what I had been put through that day a little seclusion felt good.

The first thing I did was go down to my car to bring up the packages from Victoria's Secret. I wasn't hungry so I skipped lunch and spent time in my bathroom trying on my new outfits. My bum was still burning from Sam's twenty whacks, and I made sure to put on only the softest and silkiest of panties. I felt even sexier in the new lingerie than I had wearing nothing.

Without a doubt I was enthralled by Sam and the situation I was in. He had been hard on me, but at the same time I knew he desired me and was experimenting with ways to excite me and make me want him. As I thought about the way he masterfully played on my submissive sexuality the little birds in my stomach woke up and began fluttering around again. I had to get a grip on myself.

In my past life I had once been a successful administrator in a bank and knew I had the ability to be good at the 'regular' part of this new job. I wanted to be more than just a fuck toy for my boss. In my gut I knew he would enjoy me more if he also respected me. Plus I would feel a lot better about myself.

Now how had I come up with that term 'fuck toy'? It was so vulgar and so humiliating. But as I repeated those words in my head I felt myself getting wet. It reminded me of all the submission stories I had read and found so exciting. The idea of being a man's fuck toy with no control over what he did to me sent shivers down my spine.

I sat at my desk and opened the folder Sam had given me. There were three fancy brochures from companies who chartered large motor yachts. The ships were huge, with multiple bedrooms, sitting areas, bars, sun decks, and even small swimming pools. Costs ranged from $50,000 to $100,000 a week. Crews of 4 to 6 people were advertised to cater to your every whim. I smiled at that one.

Picking up the phone I dialed the number on the first brochure. A man answered.

"Luxury Charters, good afternoon. May I help you?"

"Yes, I am calling from the Atwood Advertising Agency. I would like some information on a two night cruise this coming weekend."

"Well, normally our rentals are by the week, but our premier yacht, 'The Lady Jane', happens to be idle this weekend. For three days and two nights with a full crew the cost would be $30,000."

I did not let his early reference to the price phase me. "I see pictures and specifications for 'The Lady Jane' in your brochure. It has four staterooms, correct?"

"That's right, each with its own bath. And 'The Lady Jane' is not an 'it'. She is a 'she'."

This guy was a snob of the first order. "I'm sure 'she' is beautiful. What about the crew?"

"They are beautiful too," he laughed. "There is captain, a first mate, a cook, and a stewardess."

"Excellent. But I would need a special kind of stewardess."

"What do you mean?"

"My boss will be entertaining an important client who likes to party, if you get my drift."

"Oh, I see...."

"His actual instructions were: 'young, pretty, and willing.'"

"Ahm..... I think that can be arranged. We have had similar requests before. It would of course cost more."

"Not a problem, but I would have to interview the girl first."

"The girl I have in mind is named Felicia, and I know you would approve. She is a petite Latin beauty who likes to party. But how do I know you are serious?"

"I will give you a credit card number now, with authorization to charge me $1,000 whether I take the charter or not. If after meeting your stewardess I decide to go ahead, I will transfer half of the charter amount to your bank account immediately, and the balance on Friday when we board the yacht."

The tone of his voice changed. "You have yourself a deal. Give me the credit card information and I will call you when you can come by our office to meet the stewardess and sign the papers."

"I'm afraid it will have to be this afternoon at 4 pm. Otherwise I must call someone else."

Now he knew he was not dealing with a namby-pamby secretary. There was a long pause. "Very good madam. Come to the address on the brochure at 4 pm."

I gave him the credit card information and promised to fax a confirmation. Then feeling very satisfied with myself I leaned back in my chair. It was amazing what you could do with money. I could do things like this all day. This was easy. The hard part of my job was going to be keeping Sam satisfied. But then keeping him satisfied was going to do the same for me.

Chapter 17 – Sam

Six o'clock finally arrived, and Karen appeared at my office door. "Party time, boss," she announced cheerfully. "Where's your new assistant?"

"She has been out arranging for a boat trip to entertain the Stockwells this weekend. I do have legitimate work for her you know."

"Sure, sure," she laughed. "I'll bet our Vickie is very efficient. But we can always find excuses to punish her."

"You are the personnel manger from hell," I said. "As a matter of fact I already had to punish her today. She resisted Ginger's sexual advances when Ginger was fitting her with new underware, in spite of the fact I told her not to give Ginger any trouble."

Karen's eyes lit up. "Really? That is a serious offense. I am going to have to add my chastisement to whatever you did to her. She must learn to submit to women as well as to men."

"I thought you might have that attitude. Start the video recording system and pour us a drink while I go see if she's back in her office."

I left Karen fidgeting with the video controls and went down the hall to Vickie's office. She was sitting at her desk with various documents and pictures spread out in front of her. One of the pictures was of a striking young brunette in an iridescent blue bikini. The others were shots of the exteriors and interiors of a luxury yacht.

"Is this the boat you have chartered for us?"

She smiled prettily and handed me a paper. "It is as soon as you transfer $20,000 to this bank account. The other half will be due on Friday when we board."

"Not cheap, but a fraction of what Stockwell pays us every year. Does the girl come with the boat?"

"She does indeed. And I have interviewed her in depth. Her name is Felicia. You will not be disappointed in either her beauty or her attitude."

I was beginning to have new respect for Vickie. The fact that she had taken it on herself to interview the key member of the crew told me a lot about her intelligence and initiative. "Make sure she brings that blue bikini," I said. "She looks fantastic in that picture."

Vickie smiled. "I already told her that. And she knows she can expect a big tip if the weekend goes well. She is taking care of a sick sister and really needs the money."

"You have impressed me. Good job. But now you must come to my office to meet with Karen and me so we can review your overall performance on your first day."

She raised her eyebrows in surprise, but followed me down the hall to my office. Karen was leaning up against the glass table sipping her wine. There was fire in her eyes.