Kinky Boss Pt. 01: A Finger In...

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A fat envelope from his quirky boss keeps him going.
2.2k words
4.01
33.6k
15

Part 1 of the 2 part series

Updated 10/30/2022
Created 08/08/2014
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freeman64
freeman64
58 Followers

An insurance firm had advertised for a man to take care of 20 odd computers, running anti-virus stuff and programming them and taking care of individual needs of staff and what not. And there he was, thinking while waiting to meet the boss' secretary.

He remembered his previous slim pay and how he struggled to pay the rent. Right now he needed a laptop, new dresses and... he needed to lead a good life too. Well, he hoped he could afford a girlfriend.

After 15 minutes, a 35 year-old woman dressed in a black skirt and a white top walked up to him and sat near him, sizing him up. She had nice round breasts and was good looking. After introductions, she asked him about his experience and briefed him on the computers at the office. He told her about the previous firm he worked for, where the computers were older than the boss. After his repeated requests to replace them were turned down, he got tired and quit.

"I am about to have lunch, care to join me?" she offered.

Yes why not, he was hungry and he needed the job, too, so why not? The secretary left to get lunch. In the meantime he looked around. There were lots of cubicles all around where the staff sat and the boss' room was opaque glass. The secretary sat in a glass cabin outside the boss's room. She came back with her lunch box and they sat on a table side by side and she handed him a sandwich and took one for herself. Why should she share lunch with him, he wondered. Maybe she wanted to be nice to him and really wanted him to take up this job and hence wanted him to feel at home. It was not the first time a woman was being nice to him. In his previous job, all the women treated him well.

"So, how old are you and, if you don't mind my asking, how bad do you need this job?" she asked flashing an artificial smile. What was behind her fake smile, he asked himself and reminded himself that he should stop asking too many questions as he needed to focus and get the job.

"I am 24 and I need this job pretty bad," he shrugged his shoulders, not wanting to tell her how desperate he was.

Her left hand fell on his thigh and stayed there.

"You can feel comfortable with me. You see, there are around 20 staff and some are out, talking to clients and the rest have gone for lunch. They update their record and keep track of payments, dues etc.," she finished. But her hand was still on his thigh, as if she had forgotten it!

They finished the sandwiches and she told him that she would talk to the boss and let him know.

"Why don't you come tomorrow, same time?" she asked.

He nodded and thanked her for the sandwiches and left.

Once out of the building, he called up his friend, who was still with his previous employer, and told him what happened.

"Man, I tell you that broad wants to screw your young cock. 35, you say, she is hungry for young meat, I am sure, man," he sounded like an expert. Most people think they were experts once you sought opinion.

Well, in this case even he was sure she wanted some hot action. Whatever it was, he needed a job. So come what may, he decided to return.

--

The next day, he was at the office and met the secretary in her room. Lunch time and most employees were out, as usual, he thought.

"Let's go to the couch," she said and led him to it.

They both sat and he almost expected her hand to caress his thigh. But she had both her hands on her thighs and his eyes fell on her thick thighs. She crossed her legs and leaned towards him,

"Do you like legs," she caught him by surprise. "I mean chicken, ha ha. Do you want some." she laughed.

He said no and asked whether she had spoken to her boss..

"Yes. I will soon talk to him. Do you like legs? I mean mine," she popped another question.

He nodded dumbly. What type of game was she playing, he wondered.

Spreading her thighs, she said, "slide your hands up, come on, there is no one around."

He did slowly and his hand traveled up and reached the trimmed bush uncovered by panties.

She sighed, "play it gently, my boy," she murmured, eyes closed.

He slid two fingers smoothly into her wet slot and felt her swollen lips which were big and open like the petals of a big flower and felt a stirring between his thighs.

"So you love this. If you get this job, you have to feel me often. Is that fine?" she asked.

He nodded, as it was becoming a newly acquired habit.

"You get a regular diet of a mouthful of pussy and pocketful of money. If you are interested, you can join tomorrow," she said and got up, removing his hand from inside her skirt.

He thanked her and scooted.

In the toilet, he smelled his fingers which had explored her moist pussy and they smelled sweet.Well, at least he would get to finger a sweet smelling twat. He had had two previous encounters with women. One was with a girl his age with whom he went out. He got to feel her small bush and squeeze it while watching a movie. Since he had no money, she lasted two dates and then found another loaded guy. The other woman was working with him in his previous job, a married woman, maybe 35. He slept with her for a week, the routine being this: he would empty himself in her cunt and she would begin talking about how her husband was a no-good guy. Soon he got tired of her and stopped entertaining her. He felt no qualms about that, feeling it was revenge for the girl ditching him for another guy.

-

The next day he arrived and met the secretary. She took him in to see the boss; a bald and short man. The secretary gave a brief introduction about him and the boss nodded. She indicated that he go to the left side of the boss and turn around and stand with his hands on the table. Coming behind him she unbuttoned his pants and pulled down his underwear. He stood paralyzed not being able to believe this was happening. She stood on the other side of the boss. He felt a lubricated finger in his asshole and realized it was the boss' finger. He saw the bald boss' hand go up the secretary's skirt. The boss was having his finger in both their assholes! Kinky scumbag! Should he run away?

The secretary reached over for his cock and stroked it with her left hand. He started to get an erection and she asked him to feel her. His right hand went up her skirt and found her wet cunt and he squeezed her mound and fingered her clitoris. Her hand was working his 6 inch tool slowly as the boss was pumping his finger, now he had pushed in two fingers. He was ashamed and humiliated, being used like this. Shit, he thought. Her hand moved faster and he was on the verge of coming and he shot his load over the table. She held his throbbing manhood as he emptied himself. The boss' finger exited him and the secretary indicated that he could leave the room.

He pulled up his pants, tucked his shirt and left. It had happened too quickly and he had no time to react. Sweating profusely he sat on a chair and felt very embarrassed and ashamed that he had had an erection and had ejaculated too.

What a pathetic bugger the boss was!. He would give the secretary vixen bitch a piece of his mind, leading him on about feeding him her pussy and setting him up to be fingered by an old impotent lecherous shithead. Oh! then why the hell didn't he run away? Why did he show his ass like a whore, a male whore? Why did he get an erection and cum? Why did he finger the secretary? He was as sick as the boss and the secretary. But erection was not under his control, he was young and prone to be erect and when fondling a cunt... how could he not get an erection? His head was cluttered with so many arguments and justifications.

The door opened and he saw the secretary emerge as if she had just finished a very important meeting of great consequence and sit in her chair.

''Well, the boss likes you," she looked at his eyes.

"I feel totally let down, taken for a ride, screwed... " he hissed.

"Shhhh. People are coming back from lunch. Keep it down. Don't feel bad. He had a finger up my ass too. It lasts one minute but the pay is good. I got used to it, so will you. Be practical."

''What the fuck practical, a perv fingers my rear and I act as if I have been honored with a medal for great deeds!"

"What happens above the table may be bad, but what happens below is good," she said and he felt something against his leg.

He reached down and felt a cover. Keeping it under the table he opened it and saw money.

"He likes you and that is but the tip," she smiled.

He never expected the money.

"But, the humiliation..?" his voice trailed as she stopped him with her raised hand.

"You know how I felt when he first fingered my rear hole. The second day of my joining here a year ago, I showed him a file and I found his hand up my skirt. He parted my panties and inserted a well-lubricated finger up my asshole. He added more fingers inside and added more bills in my cover too. Tell me, where do you get that kind of money? You are talking of humiliation! you know what I did after you left the room? While he had four fingers up my ass he asked me to lick your semen off the table. Do you know that? You need the job, go to your cubicle. I can find boys who will be glad to take this job, if you don't. Thank your lucky stars he lubricates his fingers."

"I need to go out and think," he said and left the building. Sipping a coke, he wondered whether he should call his friend and ask his opinion. That gossip would end up spreading the story of his being fingered and all his friends would laugh behind his back. He tapped the cover the boss had given. If that was just a tip ... he needed to cool down and think. He sighed and once more touched the cover and patted it. He went in and sat before the secretary.

"How often would he do this?" he showed his middle finger.

"I see you have decided to take the job. You can try for a week, then decide. Mostly, we will do it once a day. Sometimes he goes away and then I am the boss, you can take half a day off if the computers are working well. You will never be overworked but will be overpaid. If I am aroused or you are horny you can come here and use your fingers in my holes. When my husband is away you can stay the night with me. Think of all the incentives," she said.

"I will try the job for a week," he said and walked toward his cubicle, thinking she was having him on as to his screwing her. Maybe she would call him home and her husband would finger him, just like the boss!.

--

It was Sunday night, he was drinking whiskey and reviewing the week that had gone by. The boss had done his lecherous deed thrice in four days and had been away for a day. The secretary kept her word and allowed him to finger her and talked dirty with him. They had exchanged sex messages and jokes regularly. She was not that bad, he thought. Since the boss was away he left before lunch, took in a movie, drank and ate. Life was good, very good, compared to the hell he went through in his previous job.

On Monday, he went to his cubicle and sat at his workstation and got ready for work. After 10 minutes, he went and met the secretary. She seldom smiled at him so that the other staff would not suspect anything. But her words were in sharp contrast to her expression.

"What did you do with your prick during the weekend?"

"I was looking for a hot hole like yours to put it in."

"Not a hot mouth?" she quizzed.

"Yeah that too," he said.

"What have you decided about the job?"

"Well, my humiliation is well-covered. I need the job," he said tersely and left for his cubicle.

You did not get to decide many things in life, situations and people make the decisions for you. And most important, always work for a boss who liked you and not for one whom you like, even if the boss was a kinky depraved one. Experience had taught him that.

-

freeman64
freeman64
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Tw0Cr0wsTw0Cr0wsover 9 years ago
well, he said.........

He did say that he needed new dresses, and he didn't have a girlfriend.

So why would he need womens clothing unless he went that way?

freeman64freeman64over 9 years agoAuthor
Honey, it will be different

Honey, the second part will deal with another kinky boss. I have planned a series on such bosses, men and women. It would not be a continuation of this. I hope that would be fun :)

HoneyAdoredHoneyAdoredover 9 years ago
Money talks

Really looking forward to seeing how this unfolds, good story line

I will be reading the next part for sure

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