THE BOSS’S SLUT 2: THE TRANSITION

CHAPTER 2: THE TRANSITION

After my usual long commute home (two subways and a train), I drove my little car the last five miles to my efficiency apartment. I lived in the Western suburbs where we lived when married. After the divorce, he moved away so I stayed put, downsized. It was a relatively safe area and apartments were affordable for a lowly Accounts Specialist. Within the last mile, I stopped to buy two bottles of cheap wine. I was anticipating a long weekend of turmoil.

I committed to putting my mind to rest for the night and looking at the proposition from Mr. Woodburn with a fresh mind tomorrow. It didn’t work. I tried losing myself in something mindless on Netflix but that didn’t work. I then tried to get into the novel I was currently in the middle of, but that didn’t work, either. I walked around the little apartment. It didn’t take much time. I went to the kitchen counter, opened one of the bottles, and poured myself a glass. I walked back to the center of the apartment and turned a full 360 degrees. I had just viewed everything that was my current existence except for the cubicle where I processed accounts from information someone above me provided and even that might not have been from a first-hand contact with a customer. I specialized in forms, not clients.

I poured a little more wine into my glass and sat down at the little table in my little kitchen in my little apartment. I retrieved the three-page job description and benefits sheet. I reread the job description and pushed it aside. As Mr. Woodburn said, it didn’t really say anything meaningful. It was corporate words to satisfy auditors and HR managers. It was a new position and the real job requirements would evolve from the activity. But, there were real necessities that needed to be considered as I suggested to him. I started writing out my ideas, issues, concerns, possible ideas, and crazy ideas. Before I knew it, it was 11:00 PM and I had pages of written thoughts and an empty bottle spread over the table. I went to bed.

* * * * *

Saturday, I began wondering why I wasn’t more fixated on the “other” part of the job. I had never been a slut before. Could I even really imagine what that was like or what to expect? The last couple years I have had my share of guys coming through and I had been married so it wasn’t like I wasn’t familiar with sex, but … a slut …

I Googled it. Slut: noun; a woman who has sexual relationships with a lot of men without any emotional involvement. Well, yeah, that was already established. Mr. Woodburn and clients. But, what did that mean? What kind of sex? My mind led me to a conclusion that there might not be any defined answer for that. Now that my mind was working around this aspect, though, I decided to seek some guidance and took a chance to call Trudy Michaels. I logged into the firm’s system and found her contact information. Her cell phone was listed. I called late afternoon.

“Trudy, this is …”

“Tina, hi.” She laughed on the other end. “I already put you into my phone’s contacts.”

I wasn’t sure how to take that. She was so confident I would be taking the position? There was a period of silence and I realized I was causing it. “Trudy, I apologize to be bothering you on the weekend, but … I was wondering if I could ask you some questions … you know … about …”

She giggled, “I’ve actually been expecting you to call. Yes, I know what about.”

“The sex. You were his mistress so you know what he is like. What kind of sex might I expect if …”

“If you took this position? Tina, what I was and what you will be are quite different. I was strictly him. You will not be. He will be a primary for you, but not the only one. All I can help you with is what he was like.”

“It’s something …”

“Okay. Mr. Woodburn is an aggressive lover. Think of it as fucking, not making love. Count on oral and pussy with him.”

“Not anal, though.”

“Tina, that’s the thing about your position. The clients. Even if Mr. Woodburn didn’t want anal, and he might with you, some clients probably will. The client aspect is the wild card here. My personal advice for you is to expect anything. If you take this, you should anticipate someone wanting almost anything.”

Almost anything. What don’t I even know about?

I decided to change and do some necessary shopping. I slipped out of the loose shorts I had been wearing and only then realized my panties were soaked through. I took them off and couldn’t resist holding them up to my face. I had never noticed my panties so thoroughly soaking. My scent off the panties was intoxicating even to me. I had planned to wear leggings to shop, but decided on a simple dress. I might be buying some thigh-high stockings.

* * * * *

It was only 8:50 AM but I was outside Mr. Woodburn’s office. I paced around the area of his door but remained close by. At precisely 9:00 AM, I knocked on his door. Trudy looked up from her work and smiled at me as I heard Mr. Woodburn say come in.

I took a deep breath, turned the handle and stepped into the room. I walked deliberately past the sitting area and small conference table. As I approach, I decided on the proper location, between the two visitor chairs where I would be directly in front of him. As I took my position, I noticed him lean back into his chair, seeing it tilt back as he did. His elbows were on the armrests and his fingers were steepled at his lips. His eyes were solidly on me. He didn’t say a word. He only watched.

I had elected to wear one of my few dresses I felt might be close to executive appearance. It was a black sleeveless, sheath dress that went to a few inches above the knees. I took a breath as my hands moved behind my neck to unclasp the catch, then unzippered it down the back. The dress sagged. I moved my hands to the shoulders and pulled the dress slightly forward and down until it would fall to my waist. I pushed it over my hips and legs. Holding the dress from the top, I stepped out of it and laid it over the back of one of the chairs next to me. This time I was wearing black lace bra and panties. For some reason, even though I wouldn’t be showing them for long, it seemed important that my underwear be sexy. By the approving look on his face, I was correct. I unclasped the bra and dropped it onto the chair and quickly pushed the bikini panties down my legs. They followed onto the chair. I now stood before him in sheer black thigh-high stocking and black three-inch heels, the tallest I owned.

He remained as he was still looking at me unabashedly from my face down my body and back up. He smiled. “I am very pleased, Tina. I think we will make an extraordinary team.”

“Thank you, Mr. Woodburn, Sir.”

He chuckled, “Mr. Woodburn or Sir will be sufficient, Tina.” He turned his chair to the side. “Now that you have agreed to the position, I think I need to find out what you can do and what you need to work on. First, sucking cock.” I smiled nervously as I moved around his desk. I looked up as I knelt in front of him, my breasts jiggling as my knees hit the floor. He noticed.

I reached for his belt, then the zipper. Opening his slacks, he raised his hips as I tugged them down. He wore blue boxer shorts. I placed my hand on the front of his shorts and flinched. I wouldn’t have pretended to be an expert or overly experienced in cocks, but his was large and it wasn’t hard yet. I replaced my hand over the front and squeezed his cock through the material. I looked up at him.

“Sir …” He only smiled.

I took the waist of his shorts and tugged them, too. Again, he raised his hips so his shorts were with his slacks at his feet. I grasped one shoe and looked up, he nodded. After removing his shoes and socks, I pulled his slacks and shorts down and off. I moved between his knees and examined the cock in my fingers. Compared to any other cock I had experience with, this one was huge. I stroked the soft cock, bent my head forward and licked the length of it. I noticed his pubic hair was missing. I took the head between my lips, then into my mouth. I sucked and licked, twisting my head and mouth as I did. Soon, his cock was hard and I pulled back to examine it, again. I held it with one hand at the base and placed the other above it. The head was still showing and I bent down to suck on it more, dropping one hand down to massage his balls.

When he came in my mouth, the spurts nearly filled my mouth each time, requiring me to gulp with each spurt. I licked his cock clean, knelt back onto my heels to gazed up at his face.

“You are very large, Sir. I suppose you already know that”, as I blushed at the silly comment. Unconsciously, I licked my lips.

“Open your knees wider.” I did as he required. “When in that position, I want to be able to enjoy the view of your pussy.” I blushed but smiled. “Do you deep-throat?”

“No, Sir.” Then I thought about the response. “Sir, maybe I should say, not yet, Sir.”

He smiled and stood up in front of me. His cock was right in front of me and it had softened very little. I leaned forward and kissed it. He put his hands down to me and assisted me to my feet.

“Your mouth is very nice. You will get much better, however.” Anticipating a lot of practice for me, I am sure. “Now, let’s see about your pussy. Bend over the desk with your feet spread wide.”

I was thinking how slutty this was to be bent over a desk in an office to be fucked by a man I hardly knew. Slutty. Yes. That is exactly what I decided to become, his slut.

I felt his cock head slide over the length of my pussy. “Do you always get this wet without being touched, slut?” Ooooooo … now I am slut.

“Not normally, Sir. I found I was changing panties regularly over the weekend until I decided to just leave them off and wear simple dresses or long t-shirts.” His cock was still moving over my slit. It stopped at my entrance. I felt it just at the opening, not quite pressing into me.

“That’s good, then. You are responding to the idea of being my slut. Now, to see how we fit.”

He pressed a little at my opening and I gasped. He was large and he was not going to enter me as easily as other men I have been with. He pressed harder and several more inches entered after expanding my pussy.

“My god, you are tight.” He chuckled, “We will have to work at loosening you up. Who knows, there may be clients with larger cocks than mine.” I groaned and neither of us was sure if it was his cock stretching me as he entered or the idea of an even larger cock.

My hands were braced on the top of the desk as he grasped my hips and pulled me back as he pressed forward. I didn’t know how far he was inside me, but when he pulled back to press back in, I was shocked that he went further in, then again and again. When his hips bumped my ass, I felt stuffed with cock. The intense feeling of being stretched to the painful point had slowly eased as he was fully in me. He pulled back and pressed back in, each time with a little more speed and a little more force until my juicing, wet pussy took his length and width with more comfort. Then, he stopped.

I looked over my shoulder at him. If I hadn’t known better, I might have thought I was being fucked by a fully dressed man. All I could see was the man in a pressed white shirt and tie still secured firmly at his neck.

He smiled and smacked my ass. “It occurs to me that you not only work for me but you are the slut in this relationship. So, why am I the doing the work?”

His point escaped me for a moment as the feeling of his large cock in my stretched pussy seemed overwhelming. Then, it sunk in. “Yes, Sir.” I pulled my body away from him until I felt the head at my opening, then I pressed back hard and quick until my ass impacted his hips. He groaned in response and my gasp was as if the air pressed into the top of my pussy was somehow being released through my throat.

One hand was on the small of my back as if grounding himself. The other hand snaked underneath me and took hold of my breast. He squeezed and fondled it, then squeezed firmly, then hard. The hand gave way to fingers taking the nipple, gently at first, then hard, twisting and pulling it. The torture was exquisite. My body started shaking and shivering as an orgasm built strongly inside me. I stopped moving, aching to avoid the orgasm from being realized.

“Cum for me, slut.”

“Sir … you … you need …”

“I said, cum for me, slut.”

The pressure on my nipple increased, again. My body shook violently. My arms became wobbly and my vision went blank. My eyes were open, but my eyes rolled back as the orgasm crashed over me with an intensity far beyond anything I had ever experienced. I heard a scream somewhere, but it was later that it even occurred to me that it came from me.

As my mind began clearing, I realized I had fallen forward and was flat on the desktop. He was still inside me and was slowly stroking as I slowly recovered. With that recognition, I pushed my body up and resumed moving my body on his cock. I had just sucked his cock and swallowed his seed before fucking, no wonder he was lasting longer. I continued to increase my fucking and it wasn’t lost on me how odd this felt. I am usually the one being fucked. Now, I am the one fucking him with my movements. I pressed back hard and discovered muscles in my pussy as I intentionally attempted to increase his pleasure. He moaned and pressed back at me as I pushed back at him. I felt his cock become harder than it had been. I moved a hand underneath and stroked my clit. I wanted to join him this time. I felt him jerk and spasm inside, then I felt the first spurt of his seed filling my pussy and at that moment my pussy spasmed around his cock and my orgasm joined his.

After he slowly pulled out of me, I turned around and took him in my arms, kissing him fiercely. “A magnificent fuck, Tina.” He stroked my cheek with the backs of his fingers, kissed me, then with his lips brushing mine, “After we fuck, I want you to clean my cock of our juices.” I blushed but smiled as I slid down to my knees with his now softening cock in front of my face. Yes, so much to experience.

I was again seated in the open visitor’s chair and we had been discussing a number of things including my ideas about handling the executive accounts. I remained naked and acutely aware of the cum in my pussy, which was undoubtedly leaking onto the chair seat. Mr. Woodburn redressed and was behind his desk.

He said he had thought about the arrangement over the weekend, also. He concluded on a number of things he wanted to institute as rules: As nice as he found my pussy, he liked bald pussy better; my clothing needed revamping, which meant that I would only wear dresses and skirts with hems at mid-thigh; he also liked my breasts, not too small and not too big and preferred them without a bra unless my blouse was too sheer, then a skimpy, lace one or covered by a jacket; he didn’t want me in panties ever; my stocking would never be pantyhose; and, he really like the view as we talked, which meant that any time I entered his office I was to strip down to stockings and heels. Oh, yes, and my heels should increase to 4-½ inches.

I had an obscene salary increase, but even so, it was going to cost a lot of money to completely change out my wardrobe. I saw him press a button on his office phone, then the door opened. I froze. His office was secure and nobody got into it unless Trudy allowed it, but it still caused my heart to stop. I turned my head to find Trudy striding into the office toward his desk with a folder in her hand. She looked down at me and smiled.

She placed the folder down in front of him and opened it for him to peruse. He asked me to pull the chair up to the desk and slid the first stapled sheets in front of me. Trudy handed me a pen. Suddenly, I was back in business mode. I was naked, but I was in business mode. The first document was defining my responsibilities for the department budget. It listed two employees reporting to me. The second was a capital request for construction of my office on the 10th floor and two cubicles outside it with furnishing, computers, phones, etc. The third was for a corporate credit card to be used for expenses in the name of the firm. The fourth was a lease agreement. I looked up.

Mr. Woodburn was smiling, “I take care of my most important employees, don’t I Trudy?”

“You do indeed, Sir.”

“Where you are living is just not suitable for your position and is too far away. Your hours will be variable and I don’t want you traveling that far late at night. This lease is for a condo on the 14th floor. I understand it is very nice.” Trudy was nodding her head. “Did I mention Trudy lives on the 12th floor. There is no 13th floor by the way. The lease will be covered through my discretionary funds, as Trudy’s has been. I want you both safe in this city.”

The next document was also a credit card. “This is for clothing and accessories, shoes, etc. Also, use it for travel to and from work by cab. It might only be two miles, but do that for me.” I smiled, not knowing how to respond to all this. “Trudy will take you out to some nice shop around here where you can start assembling a new wardrobe that will satisfy my criteria. Don’t duplicate what Trudy wears, I have given you stricter guidelines.” He certainly had and my concerns about the expense of new clothes just vanished. “What have I forgotten?”

Trudy reminded him of the transition period. He wanted it as short as possible, but he recognized that it might take two weeks for the new offices and furnishings to be expedited. In the meantime, I was to clean up my current assignments. My old managers were being informed of my promotion as we were meeting. I should begin the selection of the employee I wanted. I already had a good idea from the pool of people I had been working with. He understood but suggested that I make it look like I went through the interviewing process. The salaries included in the budget would attract anyone I wanted. He suggested I spend mornings on the 2nd floor doing those things and the afternoons in his office at the conference table reviewing the ‘executive accounts’ and potential clients list.

“In your office, Sir?”

He smiled, as did Trudy. “Yes. Trudy will pull the files as you work your way through them for familiarity. I figure that might fill the two weeks with some diversion along the way.” There was a distinct twinkle in his eyes. “By the way, Trudy, did you hear anything outside this office earlier?” I blushed profusely remembering my orgasms.

“Yes, Sir. It was muffled, but it sounded like a slut was being used in here.” I gasped.

* * * *

The time slipped by quickly. I initially focused on my projects, then on interviewing and assembling the team. Additionally, I used mornings to overseeing the construction and layout of my office and the two cubicles. I was shocked at what Mr. Woodburn had specified for me. My former manager and her manager would be green with envy. Trudy and I also used mornings for shopping. She showed me the shops with lines Mr. Woodburn seemed to enjoy. As instructed, I had my outfits tailored to be shorter. They were a length and exposure that seemed to push proper business standards, but proper business was only a part of my job now.

I spent each afternoon available in Mr. Woodburn’s office at his little conference table. Each time, I walked up to his desk and undressed in front of him. I learned he liked to scrutinize the process of my undressing. He liked to savor each piece coming off. Of course, with his dress code for me, there sometimes wasn’t much to take off if I was wearing a dress. As a result, I augmented my wardrobe with more business outfits that included a jacket, blouse, and skirt. At least, then, there were three items to remove. I found a new object in the office to the side of his desk, a coat tree. Besides his own jacket, that was now where I was to hang my clothes.

* * * * *

Of course, he was also doing a good job of familiarizing himself with my mouth and pussy. Every day, he availed himself of me in one way or another. Not that I minded at all. His cock was the largest and most amazing cock I had ever experienced. I was always wet in anticipation as I removed my clothes upon entering his office. The ease with which I took to the comfort of being sexily naked with him and Trudy and the eagerness with which my body responded to being available for this man’s use, whether I was in the middle of a review or not, startled me when I reflected on it but also reinforced to me what this man had somehow always known: I was indeed a slut that needed to be released.

He talked to me in quiet moments after a fuck or while I sucked his cock. The talks often were centered on some technique he desired me to develop or refine. He spoke a lot about deep-throating and how completely erotic and sensual the feeling of his cock tightly encased by the throat and how the muscles in the throat could more dramatically massage the cock. He admitted to enjoying it himself very much. His quiet telling of the sensation was the motivation for me to regularly try to take more and more of him. It was difficult, however. The gagging reflex was strong. There had to be a trick.

Into the second week, I was well past the mental thoughts of ‘okay, I’ll probably be fucked or asked to suck, again’ and it was now, ‘it’s almost afternoon, I can’t wait to find out how he wants me to suck or fuck him today’. I sat at the conference table facing him. That way, though I worked hard on the files, when he moved dramatically from his monitor or away from what he was reviewing on his desk, I would look up in expectation.

Wednesday afternoon of that second week, he took Trudy and me to visit my new condo. It had been going through a refurbishment with new paint, cleaning carpets and rugs, and switching out certain furniture. The condo came to me furnished and I was amazed at how stylish the furnishing was. It would be ready for me to oversee movers box and deliver my belongs from the small efficiency to this large condo on Friday. The condo was larger, most rooms were as large as my efficiency. A large balcony was off the living room with floor to ceiling windows, which I found very nice, but then found that the same windows were in all outside rooms including the dining room and bedroom. Heavy curtains on motorized mechanisms for opening and closing were in the bedroom. The living room and dining room had light curtains that opened and closed and designer blinds that rose from the floor. I learned that Trudy, with other unspecified help, had a big hand in decisions. She and I had become conspiratorial compatriots.

The bedroom was finished and I fell in love with it immediately. The curtains were pulled open to a view of the skyline. Besides the obvious items like bed, dressers, makeup table and bedside tables, a corner in the windows (it was a corner apartment) was a lounging/reading space with a Carlisle chaise lounge. I could see myself lounging there with a glass of wine, a book, and the nighttime view of the city below.

I turned around to find Mr. Woodburn and Trudy watching me expectantly. Trudy moved to the bed and pulled the covers down to the foot of the bed. I watched with understanding but in disbelief. I would certainly have expected it with Mr. Woodburn, but Trudy was not expected to be involved in my activities.

“Trudy?”

She smiled and hugged his arm as they both put an arm out in my direction. “This isn’t about Mr. Woodburn’s control. This is something I have wanted to do since almost the first time we met. There was something about you, Tina. I don’t think I can begin to explain it, but something very sexual and erotic. I mentioned it to Mr. Woodburn and he confirmed that he had felt the same thing from you.”

I stepped into a three-some hug with kisses and hands stroking. Then, I was eased back a step. She looked at me with lust in her eyes, “Strip, slut. Then you will undress us. You will enhance our sex today.”

Mr. Woodburn added, “You will not concern yourself with your own release or satisfaction. You will only be concerned with heightening our pleasure as we enjoy each other.” I nodded my understanding as I stripped off my dress leaving me essentially naked. I then began undressing them in turns, an article on Trudy, then an article on Mr. Woodburn. He added, “Tina, my slut, use this as an important lesson about being a slut.” Then he gave me the words that would become a mantra to assist me in becoming an ever-improving slut: “A true slut never assumes anything, but only seeks to improve her devotion and skills constantly, never expecting to completely attain her master’s full pleasure.”

I assisted them in their love-making, which is what it was. They shared themselves with each other in tenderness and softness as if they were lovers lost in themselves. This was not a fucking that I received or gave. It was totally different than how he used me. I found I wasn’t feeling anything about the difference. Her relationship had been different. I was his slut. A slut gets used.

The unusual feeling, though, was my unselfish assistance in their lovemaking while on my new bed in my new home. They were christening my new bedroom and I had a sense that it would be a part of the essence of the room for me, something I would always recall. That was something that would always remind me of my new role.

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This story continues in Chapter 3: Mrs. Deborah Woodburn.

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