Timmy's New Job Ch. 01

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Desperate, Timmy takes job as painslut & boytoy.
1.7k words
3.98
62.2k
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Part 1 of the 4 part series

Updated 11/01/2022
Created 09/24/2011
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Timmy reread the ad, as the bus roared up the hill and diesel fumes wafted through the open window to upset his already nervous stomach. Wanted, a personal servant to attend to my every need. Must be a male with boyish looks, at least 18, but no older. Must be no more than five-foot five inches tall or shorter. Must be thin and small. Generally, the smaller the better. Applicants must respond by email for further instructions on how to apply. No experience needed.

Timmy desperately needed this job. He was out of work, out of his rented room, and out of luck. He seemed to fit the requirements, but he stank at interviews and knew he didn't have a chance. But, what else could he do? He had only the clothes on his back, a couple of dollars he had panhandled, and an empty stomach. He wanted to eat, but he had to save the two dollars for the bus. He couldn't walk to the interview, for it was too far.

The only other possibility was to prostitute himself to any who wanted to use him. The idea scared him. He was still a virgin with no idea how to please anyone sexually. Besides, he was painfully shy.

At the library, Timmy used a computer, and a free email account to answer the ad. What he got in return were a set of bizarre instructions that he thought were a joke. He was to give the following personal information: Height and weight. Bald or not? Must have little or no body hair. Specify penis length and thickness. Any emotional attachments such as: family, girlfriends, friends, or ex-coworkers? Willingness to submit to strict rules and punishment for disobedience? If he past the written requirements, he would then report to a Doctor Morbt for a blood test and complete physical at no cost to him.

His face grew red with shame as he furtively typed in the extremely personal information. Finishing the form he clicked the send button, then waited for a response. To his surprise he received a reply an hour later informing him to report to the office of Dr. Morbt at the inclosed address between the hours of eight a.m. to five p.m. Monday through Friday. He glanced at the clock on the wall and knew he could just make it if he hurried.

At the doctor's office, he soon learned the doctor and her nurse were a couple of older women that loved to humiliate young boys. She checked out every inch of his body including the size of his penis. He remembered the doctor fondling herself, while he stood naked in front of her. Then her nurse lubricated his penis, and expertly stroked the shaft stopping, to his frustration, just before he could cum and measured its overall size.

With the examination completed the doctor said, "If you want me to send your employer a good report, you're going to be required to suck our pussies."

"I don't know how?" Timmy confessed.

The doctor laughed at him and told her nurse, "Get him ready for his first lesson."

The nurse cruelly strapped the naked boy onto the exam table while the doctor stripped off all her clothes. Doctor Morbt straddled the confused boy's face and pulled her pussy lips open wide.

Then she sat down, smothering the frightened boy under her gigantic ass cheeks and ordered, "Lick me good whore or the nurse well make you hurt!"

Timmy did not obey, so the doctor nodded to the nurse who began to squeeze Timmy's balls.

Muffled screams emerged from beneath the Doctor's ass, as the doctor again ordered, "Suck my pussy, NOW!"

This time Timmy obeyed, spurred on by the nurse who began to suck and bite down on Timmy's sore balls. After two hours of play, Timmy was finally allowed to leave.

He sat nervously on the seat as the bus bounced over the hill, past the outskirts of town, and to an area he had never seen before. These didn't look like houses, but small universities. He thought this can't be right. Now, he was on the last leg of his ordeal, and he wondered if this was a cruel joke. Why would someone in a mansion hire a bum like me?

In front of what seemed to be the largest of these homes, the bus stopped and the driver hollered back to him, "Hey, kid. This is your stop. Are you actually going in there?" he asked.

"I guess so. Why not?" Timmy nervously asked.

"It's none of my business what you do. Come on. Get off. I don't have all day!" the driver complained.

With no choice, Timmy obeyed and got off the bus. He stood starving, dejected, and wondering what he had gotten himself into! As the bus sped off down the lonely, rural road Timmy asked himself, Now what? As if in response, he heard a horn toot behind him. Jumping just in time he avoided being hit by a golf cart as it pulled up. The driver was a large buxom girl whose figure was poured into the skin tight dress that bulged in all the right places. "Are you Timmy Smith?" she asked with a smirk.

"Yes, I am," he answered wondering why she wore the sarcastic grin.

"Smith. Is that really your name or an alias?" she asked as she laughed.

"It's my name! What of it?" he growled.

"Come over here." she ordered.

When Timmy obeyed the girl slapped him hard across the face!

"Don't get smart with me or I'll have you punished!" she warned.

Timmy began to complain until he remembered that the ad did mention punishment for disobedience.

"I'm sorry. Please forgive me," he begged.

"I'll think about it. Now get in." she ordered.

The tall athletic girl drove through a large opened gate and took a short cut across an expansive front lawn that looked more like a golf course. The short boy looked into the rearview mirror. He watched the breast of the taller driver bounced like a couple of wild animals that fought inside her dress, as his cock throbbed with excitement from the violent movements. She drove him around to the back and pointed to the servants entrance.

"Go through that door and ask for Miss Tover. She's the one who will interview you." The girl grabbed him ruffly by the collar and warned, "I wouldn't get smart with her. Understand!"

"Yes Ma'am. Sorry Ma'am," he pleaded as he hoped she wouldn't slap him again.

The cart rushed off leaving him alone. He swallowed hard and went through the door. Inside he was ushered into the presence of a very stern Miss Tover. She sat at a desk, and did not offer him a seat. She seemed amused as he fidgeted nervously in her cool presence. She looked at the report Doctor Morbt had sent as she mumbled while she read.

Then she finally looked at him and ordered, "Take off all your clothes."

"W...What did you say," he stammered.

"Do you want the job or not?" she inquired.

"Are you giving me the job?"

"Yes, now strip!"

"Am I to be given a uniform?"

"No, you shall be given a bath. You stink!"

"But, I get a uniform after. Right?"

"There's no uniform."

"I wear street clothes."

"You're very slow, aren't you? You shall serve your employer naked. Do you want the job?"

"I don't have money enough to get back to the city, and I'm starving. What am I going to do?"

"I think that should be obvious even to you. Take the job or starve. At least with this job you don't have to worry about a dress code," she laughed as she pressed a buzzer.

A moment later a tall young woman wearing a bikini top and short skirt came in and asked, "Is this him?"

Miss Tover walked around and sat on the front of the desk and answered, "Yes Mary, this is the one."

Mary sat next to her as Miss Tover ordered Timmy, "Now strip bitch, and do it very slowly."

As he obeyed, the two women opened their legs and masturbated. Sitting, they towered over him as he shook with fear.

Once he was naked, Miss Tover ordered, "Lick the cum off my fingers whore. Now!"

Trembling, Timmy obeyed as Miss Tover smiled arrogantly down at him. Mary combed her cum soaked fingers through his hair. Then she painfully grabbed a handful of his long brown locks and forced him down a hall to a large, open area for mass showers.

Mary quickly stripped and hauled him into the shower after her. She adjusted the flow until it was warm. She took a large sponge and made it nice and soapy. Without warning she put him in a head lock and began to scrub his face with the soapy sponge. Mary was joined by three other tall and naked women. Two of the women held his legs wide, while the third attached a leather ball harness tight around the base of his balls and secured it with a small pad lock.

"No. Let me go!" Timmy begged.

"If we let you go, you will have to leave. Is that what you want?" Mary asked.

When the third woman finished her task, Mary jerked Timmy upright by the hair! A chain hanging from the shower nozzle was clipped to a metal ring attached to the ball harness which held him in place like a dog on a leash. His hands were cuffed behind his back and clipped to a chained that dangled from the ceiling behind him.

Timmy was tethered between the two chains, and the girls attached legs spreaders to his ankles leaving his balls and cock totally vulnerable. When Timmy started to cry they gathered around and pressed their naked bodies against him.

Smothered by Mary's large breast, he struggled to breathe as she mockingly asked him, "Is baby going to cry?"

The others laughed.

"Are you going to obey?" Mary asked Timmy.

"Don't make me leave," he pleaded. "I'll obey."

The three girls bent Timmy at the waist and head between Mary's legs. Mary squeezed her strong thighs together trapping Timmy's head like a walnut in a nutcracker. Timmy felt Mary erotically massage her clit against the back of his head, as soapy fingers slid between his ass cheeks, around his balls, and then up and down his ten-inch shaft. His teased cock was denied release, which nearly drove him insane!

Then Mary said, "Girls...we must get him ready to meet the boss."

end part 1

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  • COMMENTS
2 Comments
holycow614holycow614over 12 years agoAuthor
More to come.

There is a part 2 & 3 waiting for approval, but that may take some time.

rdoolittlerdoolittleover 12 years ago
A good start

Innocent about to get experienced. I'm liking it so far. I hope they feminize Timmy!

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