Jack’s Training Day


The sound of the Fleshlight hitting the floor is what woke him.

As Jack rolled out of bed, he was relieved at the silence from the room, next door, occupied by his brother, Sam and, at the moment, some unknown woman, who would likely be replaced with another woman before the sunset. For about two hours, in the early hours of the morning, Sam and his latest paramour kept Jack awake with what sounded like a sexual religious revival set to the rhythm of a loose headboard.

“Oh, God, Yes!”

“Jesus Christ, That’s good!”

“You’re a God, Sam!”

“Take me to Heaven!”

Jack finally relented and masturbated in time with his brother’s sexual pace and about the same time that Sam was spent, so was he.

This was the last time that he would be allowed to touch himself. He wasn’t ashamed of the practice, but he was starting a new job and one of the restrictions of this new position was that he wouldn’t be allowed to masturbate without explicit permission from his new employer. He was thinking about this when he took a hot shower, “Just one more for the road?,” he asked himself, but decided against it.

Wrapped in a towel, he searched his closet for his new tailored black suit and coat and white dress shirt. As he moved across the room, to retrieve his tie from the bureau, he stopped to check out his profile in the full-length mirror. “Not bad.,” he thought, “for a 160-pound weakling.” He snickered at this and continued to get dressed.

As he was preparing to leave the apartment, he checked that he had a pocket watch fob and a handkerchief in his left breast pocket. He was not permitted to wear a wristwatch on his new job. A small handbook, with the rules for his conduct, was tucked away in his right pants pocket. He also checked to make sure that he had the mobile phone and the little black box that his new employer had sent to him. There was something peculiar inside, but he had no idea what it was or what its purpose or use was. He checked himself in the mirror, one last time. Clean shaven: check. Manicured hands: check. Hair well-coiffed: check. Business attire: check. Jack growled at himself, “Looking good my friend.”

The mobile phone rang as he jetted out of the door. He was running late and he knew that his new boss would not be happy if he didn’t hurry.

“Yes, Mistress. How may I serve you?,” Jack answered. That was the only appropriate way to answer his new phone, as only his new employer or somebody on her behalf would ever contact him on it.

“I need you do something, have you left your apartment, yet?,” asked the voice on the other end of the line.

“I’m just leaving now. How may I serve you?,” Jack responded.

“Stop by the market and get me a dozen white roses for my office.”

“Is that all ma’am?”

“Don’t be late.”

The line went dead. As Jack got into his car, he fished out the small handbook to see if there were any explicit directions for how to handle his first task. “Josie’s Flower Market. White roses. No thorns. No baby’s breath. Crystal vase,” it read. Jack knew this was a test and he didn’t want to fail at it.

When he pulled up to the market, it was abuzz with customers, yet there was only one cashier. Jack found the roses and the crystal vase and waited impatiently for the customers ahead of him to finish their transactions. He checked the pocket watch and noted that he was already 15 minutes late. When it was finally his turn at the register, he threw cash on the counter and instructed the cashier to keep the change as he bolted out of the door.

His attempt to speed out of the parking lot almost ended in disaster as he barely avoided hitting an elderly man who was crossing the lot directly behind his car. Jack stopped. He looked in the rear-view mirror, adjusted his tie, took a deep breath, and when the old man had finally passed, he pulled out of the drive with less passion than he actually felt. “I really can’t screw this up,” he mumbled to himself.

He pulled into the long driveway of the expansive ranch-style home owned by his employer. With some effort, he managed to grab the vase of white roses and the little black box as he got out of his car. As he approached the front door of the house, his phone rang and it caused his heart to jump. His hands were full and he knew that he had to answer it, but while he was trying to figure out what to do, he was startled by the sudden opening of the front door. He tripped.

Before Jack knew it, there were a hundred shards of crystal at his feet and a dozen white roses strewn haphazardly on the doorstep. The black box had fallen open and its contents were laid out and gleaming on the “Welcome” mat, at the high-heeled feet of his new employer. He was afraid to look up as he was told to never look her directly in the eye. As he heard her speak, he focused on her red patent-leather stilettos, instead.

“Are you alright, Jack?,” she asked.

“Yes, Mistress Diana,” he replied.

“You’re late,” she scolded, “clean up this mess and come to my office, chop-chop!”

“Yes, Mistress Diana.”

Then, Jack heard a small bell chime and a man appeared in the foyer. “Yes, Mistress!,” the man said, as he bowed to Mistress Diana.

“Chuck, this is Jack. He is coming to work for me and we will train him while our Nina is away. Help him get this mess cleaned up and then send him to my office.” As she turned to leave the doorway, she stopped and kissed Chuck on the forehead.

“Right away, Mistress!,” Chuck responded, excitedly, as Diana walked towards the living-room. She seemed like she was all business in her button-down white silk blouse and red suede pencil skirt. But, her walk had an air of mischievousness in it. She winked at Jack as she turned the corner and disappeared.

Jack suddenly felt his inseam tighten and thought about the possibility of using his Fleshlight, just one more time, when his thoughts were interrupted by Chuck shoving the black box into hands. “You’d better go clean this up,” Chuck suggested.

“What is this thing, anyway?,” Jack asked, sincerely.

“It’s a chastity device.”

“A chasti-what?”

Exasperated, Chuck replied, “It’s a cock-cage to keep your junk locked up to prevent you from masturbating or having sexual intercourse unless or until Mistress Diana permits it!”

“Um. Wow! Is she serious? I mean, come on! I mean, if I say I’m not going to do anything with my penis, I mean it. I shouldn’t have to lock little Jack up!,” big Jack whined.

The men continued to clean up the mess on the doorstep, all the while Jack contemplated having his penis locked up for what would probably feel like eternity. He hadn’t really taken a good look at the thing. It just looked like a toy gun that consisted of a number of rings, but no grip; something he had never seen before. There was a tiny lock on it, but he hadn’t thought much of it. Chuck showed him how to clean it to be sure that there was no glass or other debris stuck to it.

Eventually, Chuck led Jack, black box and white roses in a new crystal vase in hand, to a red door in the back of the house. The red door had a brass knocker and sign that read, “Mistress Diana”. Chuck hammered the brass knocker three times and then exited the vicinity, but not before whispering, “Good luck!” to Jack as he rushed away.

“Come in,” Mistress Diana said, breathlessly, as she opened the door to let him in.

Jack almost tripped, again, when he saw that Mistress Diana was wearing a red leather corset, that barely held in her generous cleavage, and she was wielding a red leather crop in her hands. She stepped aside so that he could fully enter the room and grabbed the vase before he could drop it a second time. She placed the vase on her desk and then leaned over the front, making sure that Jack got a nice view of the apple of her back-side, as she reached for something from the drawer on the opposite side.

Jack swallowed hard. His voice cracked as he asked her, “How may I serve you, Mistress?”

With her back still turned to him, Mistress Diana pointed to a small door to the side of her desk, “Go in there, take care of yourself, and then I will show you what’s in the black box and how to use it. Do not take too long!”

“Take care of myself, Mistress?,” Jack asked, nervously.

Mistress Diana turned around. She walked up to Jack and grabbed his crotch. “I see that you are hard right now and trust me, you don’t want to wear that thing if you’re fully erect. This is your last chance to jack off before I lock up your pathetic little cock. For our purposes, consider it your first and last ‘smoke’ break, for awhile. Capisce?”

Jack was so turned on that he almost came in her hands. He escaped into the small bathroom, as Mistress Diana had directed and began to stroke his penis, slowly, at first. Then he thought about Nina and how badly he wanted her and he thought about Mistress Diana and how turned on he was by her. His strokes were getting almost incessant when there was a knock at the door. His penis went limp when he heard Chuck’s voice on the other side. “Lunch time, kid!”

“Um…just a minute,” Jack mumbled as he tried to get one last stroke in. It was too late. His orgasm was ruined.

Jack cleaned himself up and returned to the office, where Mistress Diana was sitting on the edge of the desk with the chastity device in one hand and the lock in the other. “Put this on yourself!,” she commanded, as she reached out and handed the small metal cage to him. He pulled down his pants and He fumbled nervously with the device. He was obviously uncomfortable exposing himself to her.

“Do you think your penis is special, Jack?,” Mistress Diana asked, condescendingly, as she grabbed her red leather crop. “You’re penis is not special. If you wish to please me and thus to please my Nina, you will stop acting like a shy school boy and just put the damned thing on!,” she yelled.

His hands were sweating. He couldn’t do it. Mistress Diana walked behind him and whispered maliciously in his ear, as she swatted his bare ass-cheeks with the cold leather stick. “You will do what I say, when I say, or else you will feel my wrath!,” she had uttered.

The chastity device was barely in place, but he knew what she meant when she had earlier told him that it would be painful to wear if he were erect. She took the lock and attached it to the top of the chastity device. That’s when he noticed that she was now wearing something around her neck, the thing that she had taken out of her desk drawer. “Is that the key?,” he asked.

“Yes, Jack. This is the key. The key to your training. The key to your future. The key to the rest of your life.” Mistress Diana took the key’s chain between your fingers and began to swing it across her breasts. She continued, “You belong to me, now, and you will do whatever I say, and be at my beck and call, whenever I say. Is that understood?”

Jack began to feel the pressure from the cock cage, again, but he did his best to suppress his anxiety and anticipation, “Yes, Mistress Diana.”

“Pull up your pants and go enjoy your lunch, I need some time alone!,” Mistress Diana instructed.

Jack did as he was told and moved swiftly as he left the room. As he closed the door, he could have sworn he heard the sound of a vibrator turning on. He winced as his cock cage got smaller and then hurried off to lunch.

Training The Young Matriarch


“But, Mother, I don’t want to go!”

Diana braced for the expected whining. Nina had never been too far away from home. When she attended college, she was only forty-five minutes away, and Diana preferred that; having her offspring close. But now it was time for Nina to be properly trained to run her own household and that meant sending her away.

Diana had raised her daughters to be able to fit in with their peers. Nina and Sharon, despite being females in a female-led household, were responsible for cleaning up after themselves. Diana forbid their father, Chuck, to ever pick up behind them. The girls were taught by their father to launder their own clothes and do many other household chores, tasks that they were expected to perform on days when Chuck was away or when they wanted to earn the privilege of having friends over.

They were allowed to date “regular” boys. Diana wanted the girls to be able to tell for themselves which ones were worth their time and which ones were a waste. Despite the fact that Chuck treated Diana like a queen, she knew that it was possible that the girls would rebel against finding a man like their father if she only allowed them to date “proper” young men.

Nina proved to be the apple of her mother’s eye. She desired to spend her time with a man much like her father: tender, thoughtful, attentive, and deferent, Diana was ALWAYS right (even if she were in error, he never talked back). Nina had gotten tired of “regular” boys fairly early on. She grew tired of their insistence that she behave a certain way or look a certain way to please them. Diana had raised her girls to express themselves freely and let no man, not even their own father, dictate how they should behave. If either girl were ever deemed inappropriate, it was Diana’s job to inform and instruct them on what was more appropriate. Generally, Diana let the girls be as individualistic as possible, but within reason.

It was time now for Nina to have a different kind of training. She needed to learn to groom any man, whether “regular” or “proper”, to suit her own personal needs.

“Calm down, Nina,” cooed Diana, as Nina slumped down onto the sofa. “The Haversham Institute is the finest training academy for what you want to accomplish.” Diana patted the cushion next to her, directing her daughter to sit there. Nina did as she was instructed. Diana continued, “I know that you are anxious to approach Jack and make him your lover, but patience is required.” She stroked Nina’s back, tenderly. “Do you trust me?,” Nina nodded. “Then it’s done. You will go as soon as a new semester starts.”

“Thank you, Mother. I will try and keep an open mind.” Nina kissed Diana on the cheek and left the room.

Diana could have sworn she noticed a skip in her daughter’s step, but there was no mistaking the feeling of pride that she felt in her own heart. Nina was following in Diana’s footsteps. But, there was a secret that Diana was keeping. A particular young man was already being groomed for Nina.

Diva’s Loving Leadership © 2015