My Four Cougars Ch. 01

Authors note: All Fictional Charters are adults over 18.

My four Cougars -- Chapter one.

The courtroom was very somber and quiet. My soon to be Ex-Wife was on one side with her Attorney, and me on the other, alone. It was an old building, the floors creaked and the only sounds were distant echoes. I shuffled in my wooden chair, bracing myself for the inevitable.

Six months ago, I was fired from my job so they could hire someone younger and cheaper. They said it was due to lack of performance, but I knew better. I was pretty bummed out about it because I had no job skills and my job future wasn't that bright. I put my tail between my legs and went home.

When I arrived at my house, I saw a strange car in my driveway, it was mid-afternoon and I had no idea who it could be. And even more puzzling was that my wife's car was in the driveway as well. It was strange for her to be home that time of the day as well. When I opened the front door I heard my wife and at least two strange male voices. They were coming from the bedroom.

There was my wife, she was giving head to one guy while being fucked in the ass by another. As it turns out my wife had been having multiple affairs with several different men. I now even suspect that she is fucking her Lawyer.

She wasn't such a whore when I married her, she was slightly overweight and somewhat homely. The downfall of our marriage started when I got her a gym membership. I thought it would help her self-esteem.

I was right, she really took to it, started eating right, and lost a lot of weight. She became fit and gorgeous, I was the envy of all my friends. But with her now killer body came temptation and she gave in to it.

She'd tell me she was going out with friends, but I never dreamed she was talking about male friends. I took it very hard because our sex-life was great, evidentially she no longer wanted to be tied down to only one guy.

My life wasn't always this pathetic, I was a jock, succeeding in any sport I decided to take up. I was the High school quarterback, pitcher on the baseball team, and track star. I was athletic and good looking.

As far as scholastics, not so much, I'd always do the bare minimum, I was a C-average student at best. I had offers to go to college on athletic scholarships but I turned them all down, school just wasn't my thing.

So here we were, getting our divorce finalized. She became the bread winner of the family and I was jobless. I had no money for a lawyer so we just used the same one. She got the house, cars, and all other assets. I was forced to buy a broken down old car and live on a meager weekly unemployment check in a fleabag motel that rented rooms by the month.

The hearing was quick and the Judge finalized the proceeding; just like that, we were divorced. My now ex-wife immediately got on her cell phone to tell all her family and friends that she was finally free.

I was walking out to my car when I received a text on my phone. It was from a number I didn't recognize. But the message intrigued me, someone wanted me to join them for lunch and discuss a job they had just created.

The meeting was in an hour and the location was a very exclusive Country Club. If I left right away I should make it in an hour, if my car held up that is.

I arrived just in time and I checked my car with the valet. The kid laughed at my pile of junk and grudgingly took my keys. I was met at the door by the maître d' who didn't approve of me entering the way I was dressed. I didn't blame him, I was dressed in an old tattered suit I got from a second hand store.

He was kind enough though to lend me a suitable jacket and tie. I told the Hostess why I was there and she led me to that back dining room where she had seated four women just minutes earlier, she had been instructed to watch for me.

When I approached the table I was astonished to see my now Ex Mother-in-Law Kathy and three other women that I vaguely remembered were her sisters.

Kathy pointed to an empty chair and asked me to join them. I pulled out the chair and greeted each women individually. On my right was Kathy, followed by Carol, on my left was Mindy the youngest, and lastly was June who sat directly across from me. All four women seemed only a year or so apart from each other in age, and clearly big breasts ran in the family.

Kathy asked me what I wanted to drink and I said just a soda. She gave me a stern look so I changed my drink choice to a whiskey old fashion.

"That's better," said Kathy.

"Lunch will be here in a minute, we took the liberty and ordered for you already," said June.

"By the way, sorry to hear about your divorce today."

All the other women offered the same condolences, I nodded in acceptance.

The drinks came and we started small talk about the weather and current events. As I sat there I started looking over my lunch companions. Kathy was the oldest and wore a navy blue pants suit adorned with a pearl necklace. Carol was in blue jeans with a sheer white top. June had on a slinky black backless dress. Kim was dressed in a white tennis outfit. All their outfits were clearly designed to show off their ample cleavage. I had trouble keeping my eyes off their chests.

We were finishing our third round when lunch finally arrived.

I was starting to wonder why they asked me there, I doubted it was just to get me drunk,

"Not that I'm not enjoying the company of you wonderful attractive ladies, but I'm starting to wonder why you asked me here, the text said something about a job."

"You're right Kathy, he is a polite young man," said June who then gave me a proposition,

"Well, we'll give it to you straight, we asked you here because we want you to be our boy toy."

I almost choked on my drink,

"Excuse me, did you say boy toy?"

Kathy explained,

"You see, at our age, women like us are just hitting our peak sex drive but our husbands are more interested in hanging around with the guys and watching sports than having sex with us."

"You are obviously a good looking guy, Kathy has been boasting about you since our niece took you home to meet her. You take good care of yourself and we heard you were a very good lover."

"We want to set you up with your own condo, get you a nice car, and give you a healthy expense account."

"In return, you'll be at our beck and call twenty four hours a day, your job will be servicing us."

I started to think this all was just a practical joke, but the look on their faces told me they were dead serious.

I took a long gulp of my drink,

"That all sounds too good to be true, there must be a catch!"

The four women looked at each other and smiled, Carol explained,

"Yes, you're right, the way we see it, when you have a nice condo, nice car, and a huge expense account, a good looking guy like you will become quite a chick magnet. But we want every erection, every ejaculation and all your time saved for ourselves."

"So, our offer is on one condition, when you're not in use we will keep you in chastity."

I took my drink and gulped it down, Kathy motioned to the waitress for another round.

I paused, these four beautiful women were offering to make me their full time gigolo, and pay me to do so.

June reached under the table and grabbed me by the crotch,

"Oooo, I think he's interested, he's got a raging hard-on!"

She was right, I found their offer erotic and stimulating. I heard myself ask,

"If I do this, when will I start?"

Kathy was the first to answer,

"Right now!"

"Say yes and we'll get things started."

June got out of her chair and walked over to me and said,

"I've got the device with me, come on and I'll get you locked up."

I paused, the large bulge in my pants was going to make it nearly impossible to stand and walk. I started taking deep breaths trying to ease my hard-on.

June said,

"Stop, don't do that, don't waste a good erection like that, I want it!"

With that June and Kathy helped me out of my chair and June led me, slumped over, to a family restroom a short distance away. She didn't even wait for my answer.

June locked the door behind us and told me to strip naked. At that point I had on a pretty good alcohol buzz, so I did as asked without thinking. Soon I stood there naked, with an immense erection sticking straight out perpendicular from my body, wondering what would happen next.

June handed me a ruler and had me hold it along my shaft, she took her phone and started snapping pictures. She was sure to get me from all angles.

"The girls are waiting to see what we just purchased, your ex was right, you really are a nice thick eight inches."

She texted the pictures to her sisters.

Then to my surprise, June started to strip herself,

"Like I said, I'm not wasting a good hard-on."

June put a condom on my engorged cock and instructed me to take her anally.

"My husband would never fuck me in the ass, that's one of the main reasons why I chipped in with my sisters for you."

June squirted a generous supply of lube on her fingers and worked them into her anal opening, she bent down and presented herself to me.

I was no stranger to anal sex, my ex-wife requested it many times.

I moved up behind June and carefully slid my erection into her waiting ass, then I reached under and started fingering her pussy. June started moaning and whimpering loudly, I was sure that all the customers in the restaurant would hear us. June didn't seem worried so I just kept hammering in and out of her ass-pussy, giving her my whole eight inches of my manhood.

We came in unison and June dismounted me. She breathlessly said,

"Yes, I'm sure going to enjoy you!"

She watched as my erection started to deflate then she removed the condom.

She reached into her purse and pulled out a cloth bag, I heard some clanking as she removed the contents. She removed the chastity device from the bag, and expertly started fitting it onto my now limp and dripping penis.

She wrapped a ring around the base of my scrotum and fitted me into the cage, she took out a hollow rod about four inches long and gently fed it into my urethra, screwing it down into the cage. Then she locked everything in place with a small brass paddle lock.

She moved back and admired her handiwork, taking more pictures.

She wiped me down and helped me get dressed. She admired the nice bulge the cage made in my crotch.

"This will sure impress our friends when you accompany us to film previews, art museums, cocktail parties and such, you'll look so handsome in your new clothes."

June got dressed herself and hand in hand we walked back to the table. I realized that I hadn't even said yes yet, but June knew what my answer would be, I did enjoy how she took charge.

When we got to the table, all her sisters were looking at their phones smiling, I started to blush, they were all seeing me naked and in chastity.

Kathy said,

Have a seat, if you can!"

The four women chuckled.

"Get used to the jewelry," Kathy said, "You'll be in it from now on, except for when your cock is in use by one or all of us that is!"

Kathy and the girls were getting a big kick out of all of this and they were giddy with anticipation of the great things to come.

June held up the key to my lock,

"Who wants him next," she asked as Kathy yanked it from her hands and said,

"There is only one key and we'll be sharing it."

Mindy, who apparently was the shy one, handed me a smart phone,

"I have this set up with all our contact info and you'll be getting a laptop with a private email address. Carol has made the calls to get your condo ready and your car will be delivered in the morning."

"Give me your car keys and we'll send your car to a junkyard to put it out of its misery."

Carol interjected,

"We will also have a Tailor visit you tomorrow so you can stop wearing those dreadful clothes."

The device on my cock must have been painful but I was pretty drunk at that point, so I wasn't feeling a whole lot of pain. We were all pretty smashed, so Carol made arrangements for the club limousine to take us to my new condo.

Carols phone rang and she eagerly answered it,

"Good, we are in the back room, and be advised, we are all a little tipsy."

I could hear someone chuckling on the other end.

Carol hung up the phone,

"The condo's ready, Melissa will be here in a minute to take us for a tour and get stud boy here settled!"

So, that's how my pet name started, in public I'd still be Michael, in our five person circle, I was "stud boy!" Mindy even made that part of my new email address.

My eyes were a little blurry from the alcohol so I hadn't even noticed the young blond women who approached us,

"So this is him, I agree he's cute" The women said.

"And hung," June interjected.

The women laughed and my face reddened.

Kathy made the introduction,

"Michael, this is Melissa, she manages the condo's surrounding the golf courses."

"So, are we ready to show him his new digs?"

"As long as it has a fully stocked bar," Kathy said.

"Of course," said Melissa, "And we'll make sure it's restocked once a week."

We all got up and pushed our chairs back under the table. June took Melissa by the hand and walked her over to me,

"I want you to feel something!"

She put Melissa's hand on my crotch as my new acquaintance started lightly fondling the cage that encompassed the penis the four women recently acquired.

"Is he as hung as he feels," asked Melissa, seemingly unable to pull her hand away from my junk.

Kathy took out her cell phone and starting tapping on the screen. Seconds later Melissa was thumbing through a new text on her phone.

She gasped and I started to blush as I figured out that Kathy had just sent her the picture's June had taken earlier.

Melissa held up her phone, turning to Kathy,

"So this is your son-in law?"

"Ex-son-in law," Kathy responded, "The divorce was just finalized this morning. My daughter foolishly let him loose, now he's ours."

A chauffeur approached us and indicated that the Limo was up front and waiting.

It was just a short drive of about two blocks until we pulled into the driveway of a twin home situated along the fairway of the tenth tee. The house had just been built. The street had only the first course of asphalt on it and the lawn in front of the house was just dirt. The driveway was just rough crushed rock.

Melissa indicated that I had a twenty thousand dollar allowance so I could do the lawn and driveway anyway I wanted as long as I followed the guidelines set forth for the sub-division.

We staggered from the car and Melissa opened the front door. The place was the quintessential bachelors pad. It had a large round bed with a mirrored ceiling, huge well equipped workout room complete with a tanning bed. The left wall of the living room was decked out with a seventy two inch flat screen TV.

The kitchen had all stainless steel appliances and fully stocked with the usual accessories.

Large sliding glass doors off the living room led to a deck with a six person hot tub. My four now employers were helping themselves to the top shelf liquor in the abundantly stocked bar.

Melissa continued showing me around, helping me set passwords in the security system. She explained the garbage pickup dates and showed me how to use the entertainment system. As I was saying goodbye to Melissa I started hearing giggles coming from the deck. Apparently my hosts were well inebriated and feeling no pain.

I walked over to them and saw that were all in the hot tub with their clothes piled on the deck next to them. Mindy held up the key to my chastity device and curled her finger motioning for me to join them.

To be continued...