Taming of the Shrew

My name is William Smith. I am a single twenty-nine year old man. I was unemployed for almost a year when my previous job was eliminated in a mass layoff due to the recession.

I recently started a new job, at a significantly lower salary and status. I took the job as an administrative assistant because I needed to get back to work, and get off of unemployment compensation. I am over qualified for the job, and I had to dumb down my resume to get it.

Instead of stating that I was in charge of a department of 40 people, I just said I was in that department. I think this is far less dishonest than overstating your experience and qualifications. Judge me if you will, but I needed a job.

My new boss turned out to be a woman, who everyone in the company calls "The Dragon Lady". Not because she is ugly, far from it. She is very attractive, slender, blonde, and always well dressed. I am guessing she is a few years older than I am, in her thirties.

Her name is Barbara Olsen. Her Scandinavian genes must have given her the natural Blonde hair. Her reputation comes from her abrasive and arrogant treatment of anyone beneath her in the company. Since I work directly for her as her assistant, I have learned that I am her favorite whipping boy.

On our first meeting, she looked me over and called me "Nerd Boy". I just smiled and said nothing. I always addressed her as "Miss Olsen." I think she is overcompensating for being a woman in a position of authority. She must think she has to be rough and tough to show she is up to the job.

On a casual Friday, she came in wearing fashionable but very tight jeans. As I walked into her office, she was reaching up on a bookshelf to get a binder of sales reports. She caught me checking out her nice butt, and she just turned and stared at me. That caused another problem, because now I could plainly see her cunt-crack, and I could not take my eyes off of it.

She didn't say a word, but I was apprehensive about what she might be thinking. I don't know what I would do if I lost this job.

After several weeks of handling one crisis after another for her, she called me into her office late one afternoon. She told me to close and lock her door, because she did not want us to be disturbed. I thought that was unusual, but I did as she asked.

She was not behind her desk; she was sitting on the couch in the arrangement of furniture you see in an executive's office, for more informal meetings. She motioned to me to sit across from her.

She said she wanted to evaluate my performance and my commitment to her as her assistant. I thought it was a little too soon for an evaluation, but I had learned not to question what she said.

She was wearing a skirt that was shorter than usual, just above the knee. She did not have her legs crossed, and the chair she had me sitting in was right where I could see up her skirt.

She maintained eye contact with me, and she saw my gaze lower to the view of her legs. She shifted her position slightly, and I could see farther up her skirt.

Barbara said, "Can you see anything interesting?" I thought she was testing me to see if I would say anything unprofessional about her very nice legs. She could use that to fire me if she wanted to. I replied "No, not really."

She sighed, and her expression turned pensive. She said, "All of my previous assistants were women. They were very loyal to me, and very obedient. Are you loyal and obedient, William?"

She really shocked me then, she moved her legs apart, and she did not have any panties on! I had a perfectly clear view of her pussy! I tried to not react, but I failed.

She said "Are you sure you can't see anything interesting? Even a naive nerd like you should be able to see something!"

OK, now I had enough. I answered "Yes, I can see something interesting. Your vagina is in plain view."

She came back with "The women who worked for me were always wiling to give me some stress relief. Do you know how to orally please a woman, William?"

She stood up, and stripped off her skirt and shoes. She was naked from the waist down, and she sat back on the couch and slouched backward, so her hips were right at the edge. She began to stroke her clit, and slide her fingers in and out of her vagina. She was very wet, and the fragrant aroma of her hot pussy reached me.

She said, "Nerd Boy, I have had enough stress today with this business. I need to unwind. I need you to lick my pussy and give me an orgasm." I continued to play the innocent, naive young man, and with a facial expression of distaste I said, "I can smell it from here!"

She barked back "It is supposed to smell that way, you idiot! Now come over here and eat my pussy like it is your favorite dessert!"

Actually, I love to make a woman lose control and have an orgasm by eating her pussy. So I dropped my innocent act, and knelt down in front of her, and dived in. She closed her eyes and leaned her head back on the couch cushion.

I kissed and licked every part of her pussy, and tried to get my tongue way up in her. When I sensed that she was getting close, I started to flick her clit with the tip of my tongue, and I pushed my finger up her asshole. Even though I pushed hard, my finger only went in up to the first knuckle.

She went off like an explosion, with a convulsive, grunting orgasm. I held still, with my lips just touching her. After a minute, she indicated that she wanted me to get up. I made it seem accidental, and when I pulled my finger out of her asshole I grabbed a few of her pussy hairs, and pulled them out. She said "Ouch! Idiot!" I slipped the hairs into my pocket.

As I stood in front of her, she noticed the bulge in my pants. She said, "Oh look, Nerd Boy has a hard on!" She reached out and felt the length of my cock, and squeezed it. She said, "Take your pants off. I want to see that!"

I pulled my pants down and off, and then my briefs. My cock stood straight out, and swayed back and forth. Barbara said, "I didn't expect that! My God, that must be eight inches!"

She took my cock in her hand, and squeezed it again. She said, "I suppose you think you are going to fuck me with this thing?" I answered, "I would like that, but apparently all you like is to have your pussy licked." She said, "And what's wrong with that?"

"Well, there are a lot of interesting things you can do with a stiff cock. And I think you need to be fucked for a change!""

It was my turn to shock her, and I said, "Do you think it is hard enough to go up your ass?" She was furious, and said, "I don't do that! And I don't appreciate your attitude. Don't forget that I am your Boss!"

"Barbara", I said, deliberately using her first name, "I think things have just changed. You are clearly guilty of sexual harassment of an employee. You could be fired, and I could sue the company and retire on the settlement."

"William", she said, sarcastically using my first name, "It is your word against mine. I am a senior executive, and you are a new hire. Who do you think will win?"

"Well, ordinarily it would be you, but I have some interesting evidence. I have a handful of your pubic hair. DNA testing will prove it is yours. How will you explain that?

She scowled, and said, "You bastard! What do you want from me?"

"Well, like I said, do you think it is hard enough to go up your ass?"

She had a look of disbelief on her face, and said, "You mean, if I let you sodomize me, you won't pursue this?"

"Sodomize is such an un-sexy word. I would prefer it if you said fuck me in the ass. Or, I could just go down to the personnel office and file my complaint."

We were both silent while she thought over her options. She said, "OK, but with a couple of requirements. First, no one must ever find out about this. Second, will it hurt? I don't enjoy pain! And how do I know you won't go ahead with your report anyway?"

"I will give you back the pubic hair I have. You will just have to trust me. And no, it won't hurt."

I told her I wanted her in a bent-over position over the armrest of the couch, but she didn't move. I said, "Stand up, bitch! I am giving the orders now, and it is your turn to obey them!" I grabbed her by the arms and lifted her to her feet.

She resisted me, but I was relentless. She said, "I can't believe you want me to bend over, with my naked ass in plain view. How humiliating! Are you really going to try to shove that big thing up my ass?"

I guided her around to the end of the couch, and told her I wanted her face down, jack-knifed over the armrest, with her butt up in the air. She reluctantly did it. Her feet just barely reached the floor, and I moved her legs apart. Her toes were just touching the floor, and I held her there with my hands on her hips. She was helpless.

I stood there for a minute admiring the view. Her long, slender legs splayed apart, her soft, smooth butt cheeks, her wet and open pussy, and peeking out of the crack of her ass was her tiny, pink anus. It looked to be about the size of a buttonhole in my shirt.

Her asshole and her wet pussy were at the right height for me, and I fingered her pussy to get some of the natural lubrication. I put my fingers up her ass one at a time, to lube it as much as possible. I started with my little finger, and worked up to the middle one. She was obviously new to this, and she squirmed and said, "Don't put it in so far!"

I stood close to her, and put the tip of my cock up against her asshole. I started to push it in, and she said, "Stop! Don't!" I pushed the head in, and she let out a yelp. She said, "I thought you said it wouldn't hurt!"

"I thought you were asking me if it would hurt me. I have no idea how it feels to you." Once again, she called me a bastard.

Slowly but steadily I pushed it up her ass, while she made muttering and whimpering sounds. With her jack-knifed over the couch armrest, her butt was lined up perfectly for me, and she couldn't escape.

Several times she said, "Stop! Don't!" But I kept going. I have had anal sex with several women, even a few first timers, but I had never felt an asshole this tight. Usually I just feel the tight ring at the entrance, but with her there was a firm tight feeling way up inside her.

When it was almost all the way in, she said, "Are you going to shove that whole thing in me?" I replied, "It's about halfway in now. I will wait a moment, and then push the second half in." She reached back in panic, and felt my cock. When she confirmed that there was only an inch or two remaining, she realized that I was just teasing her. She called me her favorite name again, "Bastard!"

When I finally had it in all the way, there was a subtle change in her. She used the same words, but reversed the order. This time she whispered "Don't stop!"

I began to slide it in and out of her, and she didn't object. The love juice was running out of her pussy, and making the couch armrest wet. I started using longer strokes, pulling my cock out until just the head was in her, and then pushing it all the way in. My pubic bone would come up hard against her tailbone, and she exhaled with a grunt each time.

She was too tight for me to go fast and furious, I just slowly pulled out, and slowly pushed in. She was whispering things that I could barely make out, like "So big!" and "Up in me!" and "Fuck me!"

I knew I wouldn't last long. I could see the expression on her face, and she had the far-off look of someone in a trance. Her eyes were glassy and out of focus, and she was breathing through her mouth.

I stopped with my cock all the way in for a while, because I wanted to talk to her before I finished. I asked her "Do you know what it is like when a man comes? Have you ever seen the cum squirt out of a cock?"

"That is what is going to happen soon, way up inside of you. I haven't fucked anyone in weeks. You can imagine how much cum you are going to receive."

"Can you feel the head of my cock, way up in your stomach? Think about the slit-hole in the tip, where the cum squirts out. If I get it in far enough, you will digest and absorb it. It is almost the same as if you swallowed it, it just gets there from the other direction."

"How do you like being the submissive one for a change, instead of the dominant one?"

She said, "Please stop talking and fuck me until you come!" Her inhibitions had completely disappeared.

It was interesting that this time she said "Please." I did as she asked, and started to give her long, deep strokes again. Every time I slapped up against her butt, it forced her to exhale with a grunt. She whimpered "Please come in me." She was actually becoming polite.

Soon I was pumping a large load of semen into her. She murmured "Yes. God, yes. Fill me up!" Everything was quiet for a while, with her impaled by my cock, which stayed very hard.

I pulled it out as slowly and carefully as I had pushed it in, and when the head popped out some cum trickled down over her pussy lips. She had to struggle to get up from her awkward position. She didn't want to sit on the couch with her wet pussy, and my cum oozing out of her asshole.

Her office includes a private restroom, and she went in and returned with a towel to put on the couch for her to sit on. I went in after her, and washed my cock. It was still partially erect when I came back.

Barbara could not take her eyes off of my cock, and she started to fondle and caress it. She said, "I never thought I would like this up my ass, but I did. I feel like such a whore. Your cum went all the way up in my stomach! I could feel every spurt!"

I said, "You don't have to feel like you are depraved. Most women have had it in the ass, and the majority of them discover that they like it. They just don't talk about it. Ask some of your women friends, and see if they will admit it."

I asked her about all of her previous female Administrative Assistants. I asked, "Did you make them lick your pussy as part of their jobs?"

"Yes, and two of them went completely lesbian after a while. I guess I taught them too well. They all left the company, except for Susan. She transferred to the Accounting Department. She still comes by once in a while for a meeting with me." Her face turned red as she realized what she had just admitted to me.

She was no longer an arrogant, demanding bitch, her demeanor was calm and pleasant. I had made her submit to something that she didn't think she wanted. But she discovered she really did want it and need it, and the change came over her as if someone had thrown a switch.

"I am going to try to make a change in my attitude, and improve my people skills. I know what people say about me. I will only call you William from now on, no more insulting names. And I will be more considerate with the other employees."

No one will realize that they should thank me, but they should. Of course, it was worth it to me just to make her realize that she does not rule the world.

I took control of the conversation, and said, "From now on, your closed door meetings are going to be different. I suggest we schedule two a week, maybe Tuesday and Friday at 4:30PM."

She agreed, and told me to write the meetings in on her calendar, starting with the next week. I was hoping that maybe we could include Susan from Accounting in some of them. I would like to watch the two of them, and then Susan could watch her former boss take it up the ass.

This job is not so bad after all.