The Assistant 63010

It became apparent that we, my wife and I, were in need of some extra income.

Our adult kids always seemed to have some kind of significant financial disaster that we would have to bail them out of and, as I had no ready stash of cash, I determined that a part-time job was the solution to my mounting credit card debt.

I was hoping for a physically easy part-time evening/weekend gig.

While perusing the Craigslist ads, I found this ad:

"Mature male seeks mature male for personal assistant, light gardening, light housework, occasional server duties. Contact for details. DISCRETION REQUIRED."

That caught my eye.

After my initial fears of mafia warlords subsided, I contacted the owner of the ad.

"Are you able to fulfill the duties outlined in the ad?" he asked.

"Yes, I believe so." I replied.

"Your age?"

"Sixty-one."

"Height and weight?"

"Six foot two, two hundred twenty-five pounds."

These questions were starting to get personal.

"Describe your hair from the neck up."

"Uh, I have a moustache and beard, graying, and I'm balding, and I keep it all short."

What difference did all that make for a job, I wondered?

"Describe your hair from the neck down."

Yeah, this was getting personal.

"May I ask what is the relevance of these personal questions?"

"They are required. Do you wish to terminate the interview?"

"Uh, no- I guess not."

"Then please answer the question."

"I am not very hairy. I shave my chest, cock, balls and ass. All other hair below my neck is kept to about a quarter inch."

"Interesting. Are you married?"

"Yes."

"What is your sexual orientation?"

Now I was beginning to suspect there was some sexual aspect to all of this.

"I am bisexual."

As far back as grade school I have been experimenting with other guys- playing with each other's little dicks and doing nude dares. Getting sucked by an old waiter I worked with as a teen...and returning the favor- My first real blow job.

Becoming a sex partner with a gay couple. Meeting other men for sex through apps. And no, my wife doesn't know...

"You will need to report for an in-person interview at my residence tomorrow at 5 pm."

I agreed and he provided the address.

I informed him that I would be coming straight from work and wouldn't have time to change into appropriate interview clothing.

"Appropriate interview clothing is irrelevant." was all he said before hanging up.

Five pm came, and I was knocking on his door.

The door opened and he looked at me, as in up and down.

"I am Peter. Come in." he said, walking away from the open door.

"I need someone who can help me with filing paperwork, who can do some light yard work, some light house work, and who can serve my guests when I entertain. Are you able and willing to do that?"

"Yes, yes of course."

"I will pay you thirty dollars an hour, with a guaranteed minimum of 8 hours per week."

"I accept!" I exclaimed.

"You must work nude."

Well, this is really the first nude dare I've had since I was 12. I could feel my cock starting to respond. There was no way I could do that.

And yet, my mouth said, "Okay."

"You will be my servant, and the servant of my guests. Our happiness and pleasure is your priority."

"So I'll really be a sex slave for you and your guests?"

"And a yard servant, and a house servant, and an office servant."

"What if I have limits?"

"It will affect your pay, but I may be able to accommodate you".

"I want the job"

"Undress. Completely. Quickly."

Fifteen seconds later I was naked.

He showed me to a closet where cleaning supplies were kept. He pulled out a broom and dustpan, then handed them to me.

"Sweep." was all he said, and then he walked from the room.

I stood there for a moment...naked... contemplating what I got myself into. I could just get dressed and leave, but the money was good and, honestly, the thought of being exposed like this, and potentially in front of a party full of people, and maybe even some sexual activities, well, it was titillating.

Lost in my thoughts as I was, I was brought back to reality quickly and painfully when his belt cracked across my ass.

"Oww!" I shouted in pain. "What the hell was that for?"

"Because I'm not paying you to stand around staring into space!"

"And I didn't say it was okay for you to hit me!"

He walked towards me, fishing his cock out of his slacks. He let it flop, and it caught me off guard.

It was impressive.

Still hanging limply, it was a good seven, maybe eight inches.

I could feel my pulse quicken and my mouth going dry.

"Kneel!" came his command.

I dropped the broom and went down to my knees. It was now at eye...no, mouth level. At that moment, I wanted nothing more than to have his soft warmness in my mouth.

"Suck!" was all he had to say, and I leaned forward, sucking his manhood into my mouth.

His cock started to respond to my ministrations, and I felt the heat start to fill my mouth. My only focus at that point was to receive my prize, brought about from his pleasure.

"If you are to serve me, then you must submit to me in all ways. When you are here, or in my presence, I own you. You will do what I say or face punishment. You now only have one choice: to accept you place, or leave. Your acceptance of my cum is acceptance of my terms. Your choice- are you leaving, or are you my slave? I'm ready to cum. Choose!"

My mouth stayed attached as I made my decision.

His milky warmness filled my mouth, as my desire made my decision for me.

I dutifully swallowed his seed as he began to soften in my mouth.

He finally pulled out, smearing my face with what cum there was left on his cock.

"Now that we've determined that 'no' is no longer allowed in your vocabulary, bend your worthless ass over the island!"

I complied, and was met with five swats with his thick belt.

I was actually crying when the last one fell. My father must have held back when he swatted me as a child.

I don't know if I'll be able to sit down when I get home. If fact, I don't know how I'm going to hide the marks from my wife.

He handed me back my broom.

"Sweep!"

"Fine, I'm going..." I said, rubbing my tender behind.

"The correct answer for me," he said with a hint of anger in his voice, "and for anyone under this roof, is 'Yes, Master...or Mistress, as the case may be."

"Yes, Master," I replied, then busied myself sweeping, not wanting to get the belt again.

Later I took out the trash, which meant going outside. I thought I heard snickering from the other side of the fence...

I had just finished putting everything away when he called for me.

"Come here slave!"

When I got to where he was, I saw it was a luxury office set up in his home.

He was on the phone talking to someone. His cock was hanging out of his pants and he was masturbating.

He held the phone away from head and whispered, "Knees!*

I dropped to my knees and moved in to suck his cock.

He slapped my face, wagging his finger at me, gesturing 'no'.

He moved closer to me and, without warning, unloaded on my face.

The cum covered my forehead, both eyes, my lips and beard.

He flung the rest of what was left onto my chest.

"Go pick up your clothes and stand by the door," then, pointing to my cum-covered face, "Leave it!"

I got up and walked to the front door, where my clothes still laid. I gathered them into my arms, trying not to let any of the cum drip on them.

I stood there, cold and naked until at last he came.

"The porch light is on a timer. Once I flip the switch you have thirty seconds before the light comes on. Be here at five o'clock the day after tomorrow."

He flipped the switch.

I stood frozen

"You're running out of time!" he said before forcing me naked out his front door.

Two days later I was once again standing naked in Peter's, er, Master's home.

He had given me a stack of papers to alphabetize and then file.

About twenty minutes into this I heard voices, and they were drawing closer.

I froze when I heard a female voice gasp.

"Oh!" she exclaimed. "Peter, you have a naked man in here!" she stated, despite the obviousness of the situation.

"Peter, what have you got here?" a male voice inquired.

"This, is my servant. He will do what you ask of him, and you may do what you wish with him"

"Well, I for one would like him to remember that I was here," the man said before landing a open handed swat on my butt.

"Ahhh!" I cried out as the pain spread across my ass cheek.

I picked up the next stack of papers which, unfortunately, went into the bottom drawer.

I tried to bend over and drop them in quickly, but the pointed toe of the lady's shoe found it's way between my legs, smashing my balls into my body.

All of this made master horny, and I looked up in time to see him unload several shots of cum on my face.

"You'll work just like that for the rest of the evening," he said.

They all laughed at that, and so I spent the rest of the evening with cum drying on my face.