Who's The Boss

by Omega

Caution: This Sex Story contains strong sexual content, including BDSM, DomSub, FemaleDom, Humiliation, .

Desc: Sex Story: Sexy new secretary takes over



Old Mrs. Cartwright was retiring. She had been my secretary for the past 5 years and my dad's for many years before that. We had a short Friday afternoon retirement party for her and Monday morning I started interviews for her replacement.

My name is Bill and I am the owner of HI-TECH COMPUTER SOFTWARE, a company started by my dad as an accounting, income tax business. I am very clever when it comes to computers and I rapidly expanded the business taking it in a new direction.

I understand computers very well but what I don't understand is women. I am 31 years old and not married. I don't even have a girlfriend, but that's not because of lack of trying. I admit I'm no jock. I am 5 feet six inches tall and weigh about one hundred and forty pounds, but I am a nice guy, I can't understand why girls don't like me. It started in college and with the exception of one fat girl, I couldn't get a date. I got used to rejection but the comment that hurt the most was when I asked this girl out she said, "What makes you think I am that desperate?"

After graduating, near the top of the class I might add, I tried a dating service. She sounded good over the phone but when I met her, what can I say, she was just plain ugly. I have my standards too you know. After that I poured my time and energy into the business and now it was about 3 times the size it was when my dad ran it.

Monday morning I was thinking about this when the first job applicant arrived. I was very impressed. She had graduated college with a degree in computer science and she was young and eager to learn. That was good because I was looking more for an assistant than just a secretary. I almost hired her on the spot, but I had scheduled four more interviews so I thought I might as well see them.

When the receptionist brought the second applicant into my office I just about dropped her resume. She was gorgeous. She didn't walk, she just kind of flowed. She had sparkling green eyes and a mischief smile. This was a dream come true. She had long honey blond hair that swirled about her like a halo. Her body looked like some of the Playboy models I jerked off to. She was wearing a black sweater and a black mini skirt with no stockings.

"You, you are Miss, Miss Andrews?" I asked as I motioned to the chair in front of my desk. Why was I stuttering and blushing like a school boy?

"Do you mind if I sit on the corner of your desk instead? I'll feel more comfortable than sitting on that hard old chair and you will be able to assess my qualifications better," she said in a voice that can only be described as sultry. Without waiting for an answer she sat on my desk allowing her skirt to slide up her thighs. As I stared at her beautiful legs she slowly rubbed her hand up and down on her bare leg.

While she did this she had a wicked smile on her face. "You are kind of cute for a little fellow; I think we will get along fine. I don't do filing, type letters, photocopy or run errands and you will have to make your own appointments. Now I know you want to see my pussy and lick it for me so call your receptionist, tell her the job has been filled, to cancel your remaining interviews and that you do not want to be disturbed.

Like a robot I did what she asked. I had never been so sexually excited in my life. It was like all my fantasies had come true and she was sitting on my desk Then she stood up, unzipped her miniskirt, let it fall on the carpet and sat back down completely nude below the waist. I tried not to look at her pussy, to try and maintain some measure of control.

"Look at my pussy," she demanded as she slowly caressed it with her long fingers. "I know you want to kiss it don't you?" she said this time with a smirk on her face. I didn't say anything but I could feel my head nodding up and down. "Get out of your chair so I can sit down on it; then you can show me how happy you are that I took the job by getting down on your knees and kissing and licking my pussy. I want you to try your best to get me off."

It was like I was in a dream, not wanting to be humiliated this way, yet wanting to please her if I could. My mind might be saying don't do this but my body was saying yes because I had an aching hard-on. I did as she demanded.

"You have not done this before have you because you are lousy at it. I see I am going to have to teach you everything. First stop kissing me. A few kisses on my pussy are enough to show your love for me. Now give me long slow licks starting at the bottom of my pussy and lick slowly up to the top. At first make sure your tongue is very wet with your saliva when you lick me. Later my juices will keep your tongue wet. Don't try and stick it in yet, keep your tongue as wide and flat as you can and keep repeating those long slow licks.

"When I start to hump your face that is the signal for you to start fucking me with your tongue. Now is the time for you to thrust your tongue in me as deep as you can. Match your speed to mine. Every time I fuck your face you thrust. If I speed up, you speed up and when I slow down you slow down. Later I'll give you a tongue stretcher and strengthener to wear at night so you can better satisfy me.

When I am ready to cum I'll grab your ears and pull you tight to me. That is when you will cover your teeth with your lips and bite my clit. That sends delicious chills up and down my body while it may cause you some discomfort as your teeth will probably make the inside of your lips bleed. I also like to dig my nails into your neck because it increases my pleasure if you are in pain while you give me satisfaction. When I release you, kiss my pussy a couple times to show me how much you adore me"

What was happening to my life? It was spinning out of control. She was controlling and humiliating me yet I lusted after her. From the very first day she embarrassed me in front of my own office staff as she insisted that I bring her a coffee each morning. Wasn't it supposed to be the other way around? Everyone else called me Mr. Denison, she called me Billie, yet she insisted that I call her Miss Andrews. She took long lunches, came in late and left early and I let her get away with it. Yet when she would walk into my office and say, "Close the door," I would be on my knees in no time while she lounged in my chair nude from the waist down. She was so erotic I could not help myself.

One of my many jobs as owner was sales manager. Sales were becoming too big a job for just Fred, my salesman and myself; that was one of the reason I hired an assistant instead of a secretary. Right from the start Miss Andrews and Fred could not get along. It soon became apparent one had to go. Now Fred was an experienced salesman, but I was under the spell of Miss Andrews, so I had to let him go, thanking him for his fifteen years service.

That night she invited me to her apartment. I thought she was going to reward me by letting me make love to her. "Bring a bottle of the most expensive cognac you can find and bring it to me at exactly 8 pm. Do not be late or early."

I told myself I would not go; to do so would mean I was giving her complete control. I was the boss and she had to realize that. I did buy a bottle of cognac but I intended to drink it myself in a show of defiance. That night as eight o'clock approached my resistance melted and I rushed to get dressed in my most expensive slacks and a white cashmere sweater. I got to her place as fast as I could. As I rang her buzzer I glanced at my watch; it was 8:04 I rang the buzzer 4 times before she let me in.

As soon as she opened her door I apologized to her for being late. "You know I am going to punish you for that but right now prepare my cognac. Put two ice cubes in it and a slice of lime on the glass. Get yourself a glass of water and bring them to the living room."

When I re-entered the living room I noticed how sexy she looked. She was wearing a short robe and I could tell at a glance she was nude underneath. I sat beside her on the sofa but she said I should sit on the floor by her feet. She leaned over and kissed me on the forehead, then told me she liked to have her feet massaged while she sipped her drink. A little later she said, "That's good Billie, now I want you to suck my toes and lick the bottom of my feet." She kept me at it for at least 15 minutes. "You are such a good boy Billie. Your sucking and kissing has got me in the mood so start kissing your way up my legs and start sucking when you reach my pussy." I got her off twice. It's easy for me to tell when she has an orgasm because she digs her nails in my neck.

After about twenty minutes she sighed," You are getting so much better at that Billie; maybe I should let you stay the night and sleep with me. Would you like that Billie?"

"Oh yes please."

"Well, if you are nice to me I can be nice to you."

"What do you mean?"

"I want you to make me sales manager and let me hire my own salesman. I took marketing courses in college so I am very well qualified."

"But you have no experience."

"I have all the experience I need. I thought you and I were going to become friends and have a good time together. I thought we would be having sex and maybe even get married some day, but I can see by your attitude that you don't see it that way so I don't think I have any choice but to quit my job and move on."

"No, please don't do that. You can be the sales manager and I'll give you a raise in pay and you can hire whoever you want."

"That's what I wanted to hear but I still must punish you for being late. Take off your belt and hand it to me, then strip and get down on your hands and knees." I did as she asked and she stood behind me and hit me with my belt as hard as she could. I could handle the first 3 or 4 hits but after that she really began to hurt me. I tried very hard not to cry or scream to show her I was a man and could take it but she started hitting me at the same place on my ass and the pain was bringing tears to my eyes.

"Oh good, you are starting to cry; now beg me to stop hurting you. It turns me on to see your tears and hear your begging.

A little later she said, "I like you a lot but you have to learn to respect me. When I punish you it's mainly to teach you respect. If you respect me and go along with what I want; who knows we may get married someday because I like an obedient husband. However tonight you disappointed me so put on your clothes and go home. Remember the first thing you do in the morning after bringing my coffee is place my ad in the paper."

The next morning she moved into Fred's old office and threw out all his furniture and replaced it with new furniture. She said she would also need a secretary so I would no longer have to bring her morning coffee. She hired both people and I did not think much of either one. Her secretary was a sexy blond bimbo. She also called Kathy Miss Andrews and me Billie. She made appointments for Kathy at the beauty salon or the fitness club. She would also run errands like pick up her dry cleaning or get Kathy's lunch for her. She would massage Kathy's neck and shoulders when Kathy wanted it and sometimes she would go in her office and Kathy would close the door. Later she would come out looking embarrassed with her hair messed and clothes wrinkled. I bet I know what she was doing in there.

As much as I thought Linda her secretary was a poor choice; I disliked the salesman Frank even more. He was disrespectful to me and a braggart. I would have fired him if I could but I knew Kathy would not let me. Kathy liked him and that was all that mattered.

You would think they owned the company as they would tell me when a customer was coming in and at what time we would all meet in my office. They often visited our customers out of town staying overnight. I had to approve Kathy's expenses so I could not help but notice they always shared a room. It hurt me because I thought she liked me but I wondered if she had sex with her salesman while only allowing me to suck her. I started feeling jealous and neglected because she had not invited me to her apartment in two weeks. I would burn with jealously and heartache when I would see them come into the office laughing and talking or watch her give him a quick kiss on the lips at the end of the day. I couldn't take it any more; I had to talk to her. I went into her office and sat in her guest chair. "Kathy, I mean Miss Andrews I have to talk to you."

"Oh my, this sounds serious," she said with a smile on her face. She buzzed her secretary Linda into her office. "Bring us each a cup of coffee and then go and pick up two tickets for tonight's basketball game."

"Yes Miss Andrews."

"Isn't she cute Billie? I know a couple of our customers have already fucked her and a lot more would like to. Maybe I should start charging them $100 to do it. I would keep 75 and give her 25; after all she is the one having all the fun. So, unless you want to give me one hundred dollars what did you want to talk about? You are going to have to hurry because I am leaving the office early. Frank is taking me to dinner and then we are going to the basketball game."

"Frank is what I want to talk about. I think you sleep with him when you are out of town. I thought we were thinking about getting married, yet you have sex with him but only let me suck you."

I could see a flash of anger on her face. "First of all sucking me off is having sex with me, and yes Frank is fucking me. Now I see you getting all red in the face so just calm down and listen. The kind of sex Frank and I have is what you will get when and if we get married. I don't do it now so that you will have something to look forward to, besides good boys are supposed to wait until they are married for that kind of sex. What Frank and I do is nothing more than casual sex. It doesn't mean anything because it's you I intend to marry. What we do now is appropriate and proper until we get married."

I left her office feeling better, even though it didn't turn out the way I had hoped. A couple weeks later she called me into her office. "Would you like to come to my apartment tonight?"

"I would like that very much."

"OK, be there at eight and if you don't want another spanking be there on time. Oh. And bring another bottle of that cognac. Frank and I finished off the last bottle."

I was feeling jealous again to know she had been inviting Frank to her place instead of me. This time I got there promptly at eight. I made her drink the way she liked. Again she was wearing her short robe with nothing underneath "Here is something I always wanted to do. I am going to relax and watch this X rated DVD I rented while I sip my drink and you suck my pussy. Now get busy and try your best to get me off. I want to look at you while you do it so strip completely before you get between my legs."

On my hands and knees I tried to pleasure her just the way she taught me. I felt a little annoyed because she barely looked at me while I licked and sucked her pussy but I was supposed to be always looking at her. She watched her movie like I was not even there. Sucking her was getting me so turned on that I had to give myself some relief so I started to jerk myself off as I licked her.

Suddenly I felt a blistering pain on my ass. I looked up to see she had a short leather whip in her hand as she slashed it down again. "How dare you touch yourself? All your concentration should be on my enjoyment. Go and get my 18 inch wooden ruler from my desk and bring it to me." I did as she asked. "Now take two fingers and push your cock down so it's pointing at me." I had such a stiff hard-on that it was slightly painful to push it down toward her.

Then I had a searing pain as she whacked me with the ruler on my cock. I could not help but cry out. My cock lost its erection immediately. "What happened to your stiffy Billie?" I jumped up and down in agony as I protected my cock with my hand and gently tried to rub away the pain. "Are you dancing for me Billie?" she said with a smirk. "Don't you see how disrespectful that is to me when you could care less about my pleasure and only be interested in satisfying your own lust? You should not get a hard-on when you suck me because you should be concentrating on my enjoyment. You annoy me when you get a stiffy because it means you are thinking about yourself not me. When we get married, that is the time for you to get hard; right now I want you to stay soft when you lick my pussy. Now let's try again."

I knelt between her legs again and licked her just the way she liked it. She got off at least twice humping my face and then to my great disappointment she sent me home.

Even though I was intoxicated with her beauty the humiliation was getting too much. At the last meeting with Deverone Industries, our largest account, she sat behind my desk while the rest of us sat on the other side. When it was break time she said, "Billie, why don't you run down to the coffee shop and bring us each a coffee." Later when it was getting down to the final negotiation for the new contract Kathy said, "Billie, thank you for your input but you can leave now while we work out the final details."

I decided it was time for me to break off this sick relationship. I was still in love with her but I don't think she loved me, she just used me.

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Story tagged with:
BDSM / DomSub / FemaleDom / Humiliation /