Teenaged Boss From Hell

I sat in the spacious office with the gigantic walnut desk separating me from Darla Worthington, President of Armstrong Industries. I was sweating bullets, being 53 years old and out of work for the past six months. I had to have a job fast, or I would soon be on food stamps.

I nervously watched Ms. Worthington slip through the pages of the rather large folder containing my application, aptitude test, resume, and medical exam results.

"I see, Mr. Jenkins...May I call you Walter?"

"Oh yes Ma'am. By all means. Of course," I nervously blurted out.

"Thank you Walter. I see by your resume and application that you are very bright, and have advanced through the ranks over the years. I also see from your medical exam that you could use a bit of exercise. 5'5", 200 pounds? Have a little tummy on you Walter?"

I stammered as I tried to suck in my gut and explained, "I'm afraid since my divorce and loss of my job, I have put on about 40 pounds, but once I get back into the work flow, I'm sure I will lose it quickly.

Ms. Worthington gave a wry smile and waved her hand. "No matter Walter. You don't need to be in prime physical condition to be an Executive Assistant now do you?"

"No ma'am. Certainly not."

"I must be honest with you Walter. This is a woman owned company, and we have but just a handful of male employees."

I watched her flip several pages before continuing.

"I instruct Dr. Rachel Baumgartner, who gives the medical exams to pay careful attention to a man's penis size, and do you know why that is Walter."

"Uh, no ma'am Ms Worthington."

"Well Walter. I find any male with a normal penis or one who is endowed, cannot resist trying to bed all of his coworkers and clients. I see from Dr Bumbartner's report that you are quite small, so there is nothing to worry about with your physical characteristics."

"Um... Thank you ma'am.... I think."

I didn't know if I should feel very insulted, or relieved.

"Before you can be hired Walter, I must double check on the accuracy of Dr. Baumgartner's findings. Do you have a problem with that?"

Thinking that she would call down to the lab to double check to see if any typographical errors were made, I said "No ma'am. Not at all."

"Very good Walter. Please stand and remove all of your clothes. You can place them over on the couch?"

"Ma'am?" I was shocked!

"Walter, Please. I am a very busy woman. Don't make me have to repeat myself too often. Now if you want the job, please remove all of your clothes and place them on the couch."

I hesitated, then thought of being down to my last $350 in the bank, and slowly rose, knowing that I had to find a job. It was torture undressing, with Ms.Worthington's eyes taking in every movement, and drilling holes into me.

"The underwear too Walter."

"Yes ma'am."

I took a deep breath and pushed them down to the floor, then stood up and covered my tiny penis.

"Please come here Walter."

My whole body shook under her gaze, but I gingerly moved behind her desk and stopped about two feet from her.

"Please clasp both hands behind your neck and spread your feet about shoulder width apart Walter."

"Please Ma'am, what does this have to do with the job?"

Crack!!! Like lightening, Ms. Worthington's hand viciously slapped my thigh, causing excruciating pain and leaving a huge red hand print.

I immediately laced my fingers in back of my neck spread my legs, and stared straight ahead at the bookcases in front of me.

I felt her fingers go to my waist and squeeze the excess flesh at my waist, then move to my front to wiggle my slight pot belly.

"I can see where that 200 pounds rests Mr. Jenkins. If we decide to hire you at Armstrong, you will have to work on that."

"Yes ma'am."

I closed my eyes when I felt her hands roam lower and took in a deep breath as I felt her grasp my tiny penis.

"It appears that Dr. Baumgartner was correct. About one half inch?"

"Actually ma'am, I think it's about three quarters of an inch."

"Well Mr. Jenkins, I think you need to remeasure, but that's beside the point."

I felt her twisting and turning me in every direction, still not understanding what kind of interview I was being subjected to. As if reading my mind, Ms. Worthington said,

"Males are known to think with the penis Mr. Jenkins. We have a strict policy of not dating among employees. It seems apparent from the extra wrinkled flesh around the sides of your penis that you perhaps masturbate quite often. Am I correct Mr. Jenkins?"

"Ms Worthington, what does my private life have to do with me doing a good job for Armstrong?"

"Good question Mr. Jenkins. I have found that males with merely a fantasy life, will be more punctual since they are not out all night, and will also create fewer problems in pursuing female coworkers. How much do you masturbate Mr. Jenkins?"

I could feel the blood rush to my face as I admitted, "Two to four times a day ma'am."

"My my. I can see why the little fellow is a bit wrinkled. You give him quite a Workout don't you Mr Jenkins?"

"Yes ma'am. I do."

She released my penis, and said "You do keep your bottom clean don't you?"

Exasperated at her outlandish questions, I exclaimed, "Yes ma'am!"

"Just checking Mr. Jenkins. I want you to take a seat again, and will not tolerate any stains on my furniture."

Feeling totally degraded, I took my seat again.

"Well Mr. Jenkins, I am prepared to offer you the position, but I do not have the final decision in the matter. The job will pay $57,500 per year with health benefits and use of the company gym."

"That sounds very generous Ms. Worthington. I accept your offer."

"Not so fast Walter. As I said, I don't have the final decision. That rests with my 18 year old daughter, whom you will be working for. She just graduated from high school, and I am grooming her to eventually take over the company. She is now Vice President of Marketing, and is in need of an Executive Assistant."

I could taste the check coming in, so I was willing to agree to anything.

"I'm sure we will get along, and I will do a good job for her."

"Okay Mr. Jenkins. But she can be a handful. Darlene, will you tell my daughter we are ready for her?"

I had completely forgotten I was naked, and stood out of courtesy as her daughter came in the door. I couldn't believe her. She stood only about 5 feet tall, and had her blond hair in pigtails, and had all of her mother's beautiful features. Her body was taut and tight, blessed with smooth muscles from genetics and gymnastics.

She two steps into the office and stopped short with her mouth handing open.

"Mother, you have GOT to be kidding me!"

She closed the door and advanced towards me, looking me from head to toe. "You want me to hire this overweight, ancient, under endowed poor excuse for maleness?"

I saw red and exclaimed, "I don't need to take this abuse from this little bitch."

I turned to the couch to retrieve my clothes and two fingers were roughly shoved up my rectum.

"Ahhhhhhhh." I screamed, standing on my toes and frozen in place. "Please stop! You're hurting me!"

"If you intend to work for me old man, you will learn that you will not leave until I give you permission to leave. Understood?" I didn't answer fast enough and she rammed her two fingers deeper. "I said....Understood?"

"Yes...Yes. Please stop."

She removed her fingers, but spun me around and before I could think, she sent a hard right hand into my stomach knocking the wind out of me and causing me to double over.

"And that is for calling me a bitch."

"Please... I apologize."

Ms. Worthington sat back in her executive chair with her hands laced behind her head and a big smile on her face.

She stood my naked body up by grabbing me by the hair, and sent one of her tiny fists full force into my left eye, closing it almost immediately. The impact sent me stumbling back, but the teen tormentor pursued me and sent her other fist to my other eye. I was looking at her advance and use my aching body as a punching bag through two slits as she turned my face into hamburger, making blood pour from my lips.

I was out on my feet, providing no resistance with I heard Darla say, "That's very good Honey. Now you must know your employees limits, so now is the time you make the final demands and negotiations."

The young muscular powerhouse backed me up against the wall and took me by the throat in one hand, and grabbed my tiny penis and balls in her other little hand. She squeezed and kneaded my sore meat roughly, applying pressure when she wanted to emphasize a point.

"You're a pitiful excuse for a man, but I am going to offer you the job. If you let me down in any manner, we will have another closed door session like this one in my mother's office. Do I make myself clear?"

She squeezed my tiny balls and cock incredibly hard, looking for an answer, and I screamed, "Pleeeese. Yes! I understand. I will not let you down. Please stop hurting me."

"You will address me as Miss Worthington at all times, and you will do my bidding, no matter what is asked of you; from bringing my coffee, to wiping my butt. Understood?"

"Yes! Yes! I'll do anything. Please let go of my penis!"

"That tiny thing isn't even worthy of being called a penis. I don't know why I am taking a chance on a washed up tiny peckered old man like you, but you are to report to work at seven sharp tomorrow."

She gave my cock and balls one last painful squeeze, released me, then sent a knee to my aching balls, causing to me to roar and crumble to the floor in pain. She then left the office and Darla just let me lie on her carpet for fifteen minutes until I recovered.

When I was able to rise, she handed me my clothes, explaining that she had a meeting in 10 minutes and I would have to dress in the men's room down the hall.

Slowly I made my way out of her office and down the hall, but was in too much pain to care about exhibiting my small member and naked beaten body to all of my future female coworkers. It was going to be a different world working as a minority male in a firm of tough hardnosed women, and as I pushed the door open to the restroom, I prayed that somehow I could get on the good side of Miss Worthington.

The End