The Personal Assistant

Karen knocked on my door and opened it. "Good morning Sam. I met your new assistant in the parking garage and have brought her to you."

"Thank you Karen. I will take care of her from here. Come in Vickie."

With an evil grin Karen dropped her eyes to indicate I should check out Vickie's stockings. Then she turned and left. "See you later," she said cheerfully.

Vickie stood in front of me smiling nervously. "Good morning, Sir," she said.

Reaching out I took hold of her hand. "Good morning, Vickie. Welcome to my company." I could feel the tension in her body, and she trembled slightly, as if my touch were electric. Good, she was just anxious enough to make conquering her a pleasure.

I took a step back and spoke sternly. "Please stand still so I can inspect you. Appearances are very important in our business, and I will check you over every morning to make sure your attire and demeanor are impeccable. No matter what your assignment is for the day, you are to come to my office first thing to be inspected, and to make my coffee, which is to be ready promptly at 9 am."

"Yes Sir," she said.

She was off balance and I wanted to keep her that way. I relished the power I had over her and the way she reacted to my manner. Continuing in a harsh tone I warned her about displeasing me.

"Any error in how you present yourself will be dealt with swiftly and painfully. Do you understand?" As I said those words I turned and looked at the crop on my desk. Vickie followed my eyes and gasped. I saw a rustle in her skirt as she reflexively clenched her thighs together.

"Now for the first few days, until I can be sure you have learned to wear the right underware, I will require that you take off your skirt and jacket, just as you did in the interview. I trust you are not wearing panty hose again."

"Oh no Sir," she said quickly.

"Well then get on with it." I picked the crop up off of my desk and sat on one of the stools. "And you can leave your clothes off while you make the coffee."

Her face was flushed and her chest heaved as my words sunk in. She seemed paralyzed.

I tapped the crop on my leg. "I'm waiting," I said.

Chapter 10 – Vickie

The tapping of the crop was like the clock ticking in the old Gary Cooper movie "High Noon." Even though I had expected something like this, it was still so foreign to my experience that I held back. I was literally trembling.

Sam seemed in no hurry. It was like he wanted to make me cross the threshold on my own. Then I would be fully committed. This would be the first day of the rest of my life under his command.

Finally I found my voice. "Can you please lock the door first?"

"No."

"No?"

"I said No!"

"But... but....."

"Yes, someone might come in, but it won't matter. You are now my personal assistant, and the other employees are soon going to know the nature of your job. We have few secrets here."

"Do the other executives do things like this in their offices?"

"Of course. We are known for our ultra liberal atmosphere. It's one of the reasons we are so successful in signing up new clients. Now take off those clothes before I get angry."

The crop slapped against the leg of his stool in a way that sent an unambiguous signal. If I did not get with the program I was going to suffer. I inhaled deeply and resigned to give it my best shot. My jacket, skirt, and lace camisole soon lay in a heap on the floor. Standing before him I hoped he liked my lingerie. He looked me over but didn't say anything.

To cover my embarrassment I tried to act like everything was normal. "How would you like your coffee Sir?"

"Black. I made it for you this morning, but from now on you get here earlier and have it ready."

"Yes Sir."

As I turned to the coffee machine on the credenza I caught a glimpse of a smile cross his lips. I moved slowly, giving him a good look at my nearly naked body. When I had filled his cup and started back toward him, the smile was gone, replaced by as powerful a look of lust as I have ever seen. Just looking into his eyes made me weak in the knees. I leaned forward to hand him the cup and deliberately hung my tits in front of his face. Surely he would grab me and pull me into his lap.

Instead he leaned back and sipped on the coffee. "Thank you Vickie."

I stood before him like a supplicant slave girl, not knowing what to say or do next. My heart was pounding. He continued to sip his coffee and move his hot eyes over my body. It was clear he would act when he was good and ready; my uncomfortable situation didn't matter. Or maybe he wanted to prolong it.

Suddenly he put his cup on the floor and stood. The crop appeared in his hand and extended toward me, the little flap just touching the point of one breast. The sensual smell of the oiled leather was over powering. He raised the crop and traced the curve of my tits through the bra until the flap arrived at the other nipple. My chest heaved as I tried to press my nipple against the leather tormentor.

"Please......."

"Please what?" he asked as he walked around me, dragging the crop over my shoulders and down my spine. When it reached the top of my ass he let it go lower, right into the valley between my cheeks, inching ever so slowly downward toward my pussy. "Please stop, or please continue?"

It took all my will power to remain still. My pussy was completely soaked, and I was hoping he wouldn't touch me there and see what he had already done to me. "I... oh god... please don't tease me any more ...."

Grabbing my arm he spun me around so we were facing each other, inches apart. Then he dropped the crop and put both hands on my ass, pulling me against the hard rod in his pants. "You're lucky I even want to tease you, considering your ugly old lady underware. Just because you are wearing a thong does not make it sexy. It has no style. And your bra covers too much and is so stiff I can barely feel your nipples, even though I know they are hard as marbles."

It was true. My nipples were like stone pebbles and my pussy was soaking. His big hand slipped under the back strap of my bra and jerked until it broke free. Then he did the same thing to the thin bands of my thong.

"We will be getting you some more appropriate undergarments," he growled as he pushed me back and lifted the torn lingerie from my body. Except for my garter belt, stockings, and heels, I was now naked. He looked me over like he was appraising a painting in a gallery.

"Very nice. Beautiful breasts and ample hips, not too big. I am going to enjoy you, starting now. Get over there and lie across my desk."

When I hesitated he stooped and picked up the crop. As fast as I could I moved toward the desk, but still he caught my ass with two sharp blows. As my thighs hit the edge of the heavy, wooden desk, I felt his hand on my back bending me over. His voice was horse with desire.

"Grab the far edge and hang on. Good... Now spread your legs..."

It is difficult to describe how I felt at that moment. I could picture the lewd spectacle I was making, my bare ass up in the air hanging off the edge of my boss's desk. With my thighs open the damp hairs on my pussy would be glistening at him in open invitation. My ass stung from where he had spanked me. I was embarrassed and humiliated, but also as turned on as I have ever been.

He ran his fingers lightly over my exposed pussy and taunted me. "You need this, don't you Vickie?" I heard the unmistakable sound of a zipper being opened.

"Ohh......", was all I could manage.

"Tell me what you want, Vickie."

"Goddddd....... ahhhhh... you know.... don't make me say it...."

"Say it bitch!"

I was broken. There was no point in denying him. "I want your cock in me.... fuck me...... pleassssse.. fuck me NOW.."

His attack was so sudden and powerful that I could hardly catch my breath. The first stroke opened me like pealed fruit, and the second reached deep into my gut. After the third I was close to orgasm, shaking and pushing back against him. His mouth was against my ear.

"No," he growled. "You don't get to cum unless I give you permission. I want to keep you on edge all day. Now use your pussy muscles to milk me. I am very close."

"Pleassssseee..", I moaned, desperate for release.

A hand closed on one breast, pinching the nipple cruelly. "I told you to squeeze me," he whispered.

Without my even thinking about it my pussy spasmed on his cock. It was like he had direct control over that part of my body. The pressure set him off, and I felt a gusher erupt into me. He moaned, kissing my ear and cheek. I wanted so badly to cum, but he pulled out and left me just below the peak.

"Not bad," he said, still breathing heavily. "You have a nice tight pussy."

He walked around the desk until his wet cock was hanging in front of my face. Wrapping his hand in my hair, he pulled me toward him. The odor of sex stimulated my juices even more.

"Now look at the mess you've made," he said. "I don't want any of this on my pants. Use your mouth to clean me."

I did as he ordered, enjoying hearing the little sounds of pleasure come from his throat. The taste of him kept my blood boiling. But after a minute he seemed satisfied and eased his cock back in his pants.

"Very good, Vickie," he said. "I wanted you to have an energy drink to start your day. Now get dressed. I am sending you shopping."

With that he picked up my torn thong and bra and threw them in the waste basket. I was just starting to get up off the desk when he picked up the phone and dialed a number from memory.

Chapter 11 – Sam

Looking down at Vickie as she licked my cock clean I couldn't help feeling pleased with myself for choosing such a perfect personal assistant. I had expected some hesitation this morning, and was pleasantly surprised at her reactions. I may just have to feed her a breakfast energy drink every morning.

But that underware was terrible. I had to teach her to stop thinking of herself as a middle-aged woman, and more like a vamp. My friend Ginger at Victoria's Secret was just the person to help me do that.

As I dialed Ginger's private line I enjoyed watching Vickie slip her camisole over her head and then struggle into her business suit, minus any other under garments. Ginger would be amused when I sent her a customer dressed liked that.

"When you are dressed, go sit on the stool," I said to Vickie as Ginger's line was ringing. "Keep your skirt raised so I can see your legs."

Ginger answered after the fourth ring. "Hello, Ginger speaking," she said in her sultry voice. Only her best private clients had this number. "How might I serve you today?"

I laughed at her suggestive tone. "Hello my dear. This is Sam, and I have a new customer for you."

"Sam! It is so good to hear from you. I thought you had forgotten about me. It has been ages since you sent one of your special friends to see me."

"No way I would ever forget you and your services," I said cheerily. "After my friends visit you they come back much improved, in both appearance and attitude."

"That's my job," she chirped. "Who do you have for me this time?"

"Her name is Vicky, and she is my new personal assistant. She will be involved in entertaining me and my clients, and I want her to look good in all situations." Saying this I scanned Vicky up and down and gave her wink. In response she squirmed on the stool and stuck out her tongue at me. She was really getting into the spirit of things.

Ginger replied in her usual straightforward way. "What kind of body are you sending me to work with?"

I was glad Vickie could not hear Ginger's end of the conversation. It might have put her off. "You will have no problem there," I said. "She is a little older than the others, but she has all the right assets."

"Any special requests?"

"You know what I like. Make what she wears a sexy surprise under her conservative business clothes."

"No problem. When is she coming?"

"She'll be there in half an hour. You have a $2,000 budget. Spend it all."

"Yum."

"Bye for now," I said and hung up the phone.

At the mention of the budget for just lingerie, Vickie's eyes lit up. "That's very generous Sir," she said.

"Go now. I want you back by lunch time, as I have an important assignment for you this afternoon. And don't give Ginger any problems or you will suffer the consequences. Understood?"

"Yes Sir."

Chapter 12 – Vickie

I couldn't believe what happened that morning! What a way to start a new job! I wondered if he was going to fuck me make me suck his cock every morning. As I slid off of the stool I was aware of the continued dampness on my bare pussy. I thought of what I had done the day before in the parking garage.

It was exciting that Sam wanted me to have erotic lingerie to please him and his clients, but I hoped he was not going to make me service his clients the way I had to service him. Heading to my car I could not help but feel excited as the cool air wafted over my warm, damp pussy. With no panties on to soak up my juices I would have to resort to using a paper towel to wipe myself dry. I certainly could not go into Victoria's Secret and let Ginger see me dripping.

It took me only twenty minutes to drive across town to the store. I checked my watch to make sure I got back by lunch time. As I walked into the store there was bubbly, voluptuous Ginger waiting for me.

"Hi there. You must be Vickie. I'm Ginger."

Ginger was very attractive and super friendly. With her young, lush body she could be one of the Victoria's Secret models. I suddenly felt very old. But then I remembered that Ginger knew my boss had sent me to buy lingerie to please him, and I was embarrassed.

"Hello Ginger. This must seem like a strange situation to you."

She laughed. "Not at all. Our best customers are the men with charge accounts who send their women to see us. Any woman who doesn't take advantage of that is crazy."

"I'm not sure exactly what he wants me to buy."

"Leave that to me," said Ginger. "I have already laid out some items for you to try on. It's important to get the size right."

Taking my arm Ginger led me to a large dressing room at the back of the store. Several other clerks smiled at us as we passed them, making my face even redder.

"Here we are," she said. "I'll lock the door so we won't be disturbed. Now take off all your clothes except for your stockings and heels, and we can begin. I understand you have to be back on the job by noon."

I was surprised that Ginger was staying in the room with me. Looking around I searched for a door or curtain to a private cubicle where I could try on things, but there was none. Instead there was a low platform in the middle of the room, and beside it an upholstered arm chair, which is where Ginger settled herself. Many pieces of lingerie were scattered on top of a long wooden table against one wall.

"Could I please have some privacy while I try these things on?" I asked.

"Sorry dear. Store policy is that a sales clerk must be present. You would not believe how many of our expensive pieces get stolen by women if we leave them alone. Sometimes women will come in wearing no under garments under their clothes, and then leave wearing our best stuff. It's incredible."

Now I was really embarrassed. I could not take off my clothes and reveal that I was like those women. "You don't have to worry about me stealing anything. Now please leave. I have never undressed in front of another woman."

Ginger's face took on a hard appearance. "Do I have to call Sam and tell him you think you are too special to abide by store policy? Other women he has sent have had no problem. Knowing Sam, you will be in big trouble."

She was right. Sam would not be pleased to hear complaints from Ginger. I had no choice.

"Oh all right," I said. "But I am not like those other women—the ones who come in to steal things."

As nonchalantly as I could manage I began taking off my clothes. Ginger sat silently, watching me with a satisfied look on her face. When it became obvious that I was wearing neither bra nor panties, her eyes opened wide.

"Well, I see why you didn't want me here," she smirked.

My face was very red. "It's not what you think. Sam made me throw away my old underware."

"Good for Sam. You have a great body and we are going to fit you in things to show it off properly." She pointed to my garter belt and hose. "Take those off too. I want to outfit you totally in our garments. After all, we have to spend $2,000."

For the next hour I tried on endless combinations of the sexiest lingerie I had ever seen. There wasn't one bra that covered half as much as my old one – the one Sam had ripped off of me. Ginger had brought in items of various sizes and made sure I selected the ones that fit properly. The materials were of the finest silk, with each outfit more beautiful and sexy than the last.

When I had put on the last set, a filmy blue half bra with matching thong, Ginger got up from her chair and walked up to the edge of the platform. "You are a beautiful woman," she said.

I did not like the lustful look in her eyes. "Thank you," I mumbled and started to step down.

"Wait," she said. "I am not sure this outfit is the proper size." One hand went to the cleavage between my breasts and the other started sliding down my lower stomach.

"No," I said and pushed her hands away. "Everything fits just fine."

Her eyes flashed. "As you wish," she said sharply. "I just hope that Sam agrees. Take off those items you are wearing so I can pack everything up and prepare the bill."

"I would like to wear these last pieces so that I can go back to work feeling dressed."

"Sorry," she said in a tone that indicated she was getting even. "Store policy is that I must pack everything. You must leave the way you came in."

She left and I got dressed. Ten minutes later I picked up my packages and went back to my car. Unbeknownst to me she had immediately picked up the phone and called Sam, because when I got back to Sam's office he was waiting for me with an angry look on this face.

Chapter 13 – Sam

I knew when Vickie left that she would come back with some very enticing lingerie to entertain both me and my clients. I could always count on Ginger knowing my taste. Sitting back and looking out the big windows in my penthouse office I planned the rest of my day with Vickie in mind. I managed to do a little useful work, and the morning went quickly.

It was almost noon when Ginger called to tell me that Vickie had pushed Ginger's hands away when she was trying to check the fit of some items. I knew that Ginger was bisexual, but that did not matter. I had specifically told Vickie not to give Ginger any trouble. That kind of disobedience had to be dealt with severely, and right away. It was obvious that Vickie had not been broken in yet.

When Vickie came into my office I was sitting on the stool waiting for her. "How did things go with Ginger?" I asked.

"Very well," she replied. "I think you will be pleased with what I bought."

"That's not what I heard," I said with a scowl. "Come here and look at me."

Vickie looked alarmed, but came and stood before me. "What do you mean?"

I stood and grabbed her by the hair, bending her neck back. "I'll ask you again. How did things go with Ginger?"

All at once it seemed to dawn on her. "Did that bitch call you and tell you I had pushed her away when she started caressing me?"

"She's not a bitch; she's my friend. And I told you to obey her. You are to follow my instructions whether I am with you or not." I pulled harder on her hair, and her eyes started to water.

"I'm sorry Sam.... she was getting fresh.... you didn't tell me I was supposed to have sex with her. I have never been with a woman before."

"When I tell you to obey someone that means you do whatever they want. You have to be taught a lesson. Now get out of those clothes again." I felt myself getting hard. The fact that she had never been with a woman was going to make for an interesting evening with Karen.