Femdom Boss Pt. 03 - Training

The tall redhead, whom he came to know as Miss Stacey, woke him up very early. She led him out of the room, and up to the kitchens where she had him kneel in a corner, then brought a small bowl over to him with a brown mush, and sat it down in front of him.

He looked up at her, and she just shook her head and leaned down, grabbing the back of his neck and pushing him down towards the bowl, "This is your breakfast, toy. Eat up, you will need your strength, and we need to get you cleaned up. Lots to do today."

The began eating, it didn't taste awful, though not particularly good either. Kind of like oatmeal, but Miss Stacey informed him that it was nutritious and would give him the strength he would need to perform his duties.

Miss Stacey then ate her breakfast, and once finished, she gave him some water, then led him back up where he was bathed again, but this time, instead of the gray frock, he was left naked.

Leading him outside, he noticed it was still dark, and chilly this morning, and he realized that he must not have gotten much sleep at all. They arrived at a barn, and as they entered he heard Stacey call out, "Hey! Where you at barn rat?" As she finished the question an older gray haired man walked out. He was wearing a collar much like the one the boy now wore, had a stooped gate, and was quite naked.

"I'm comin', Miss, I'm comin, hold your horses," The old man's voice was raspy and as he drew closer he realized the man appeared ancient.

Stacey pulled him closer and whispered to him, "Barn rat here has been in the Boss's service for Her entire life, he was Her Mother's pet before becoming Her's after the old Matriarch passed. He takes care of most of the equipment, and is very good with metal working, woodworking, pretty much anything that is required."

John blinked, not really understanding any of that as he watched the old man check him out from top to bottom, "Well, well, Boss lady found Herself a new toy I see? This one is kind of small isn't he?"

"Perhaps, but he's cute in his way, and honestly, rat, who really cares what you think anyway? The old man grinned and chuckled. "Let's just do what we need to do, rat, k?" Her tone was more amused than upset, and it seemed the two of them seemed to have a weird rapport between them. Miss Stacey then reached down and grasped between the old man's legs and leaned close, "Besides, not like you're every going to be using your's again anyway, right?"

The old man's face turned red, and you could hear his raspy, gasp, but the boy noticed that what Miss Stacy had grabbed, wasn't a cock, well, it was, but, it was encased in a metal shell. He wasn't quite sure how it stayed in place, and didn't just slide off, but he thought he saw a lock dangling down near the base. "Anyway, the Boss doesn't want his cock for anything, too small for Her, you of ALL people should know that!"

The old man turned even redder then and mumbled something, John thought he heard, "size queens" and something about "stretched out..." Til a firm slapping sound shut off the old man's mumblings and he rubbed his butt and grinned at Miss Stacey, "Seems to be taking more to get you to give me a good smack on the bottom lately, bout time."

Miss Stacey just laughed and said, "come on, get the boy fitted, the Boss wants to lock it on him when She is at breakfast."

Soon, he was standing before a workbench and the old man was fondling him, measuring, trying various metal tubes on his cock, his balls. Normally having his balls fondled would have made him hard as a rock, but this something, just had no effect on hi, and soon he was led out by Stacey, who carried the new Chasity device in one hand, and his leash in the other.

Soon they arrived at the veranda where his Boss was finishing her breakfast. She looked up when he approached, and Miss Stacey whispered under her breath so only he could hear, and following her instruction, he knelt before his Boss and whispered, "Good morning, Ma'am, toy trusts you slept well? How may it please You today?"

Those words were strange and as he listened to himself speak what Miss Stacey had told him sounded odd in his ears. Then his Boss smiled down at him, and her hand reached down and stroked his unruly hair softly before whispering, "Very good, toy, very good. Now, what have you brought for me?"

Miss Stacey handed her the device and she inspected it closely, "Yes, the rat still does very good work, stand up toy, up now."

He stood, and She wasted no time, soon his cock was in Her hand and now, he did get hard.

A harsh smack to the head of his cock jerked him out of his own head and back to Her as he nearly collapsed from the pain. His cock shrinking quickly as his knees trembled. Her quick, "Don't you dare collapse, toy, stay right as you are," kept him trembling, but standing.

Soon, the device was in place. As he looked down at it, his eyes widened. It was solid steel, completely encasing his cock, fitted perfectly. He could feel the smooth inside of it nestled right against his flesh. A hole in the top would allow him to pee, a ring circled the base of his ball sac, and as his Boss tightened it up, she spoke, "Now, toy, this is to keep you under control. We truly do not have a use for a cock, and you don't really have one anyway, so it will stay here. From time to time, I will have Miss Stacey drain you so that your balls don't build up too much, but that will be rare. He flinched as he heard the lock click and then saw her toss the key to Miss Stacey with a curt, "Have that melted down, dear." He didn't see the wink she gave to Miss Stacey and he was certain that he just lost complete control of his cock.

After the device was in place, his Boss stood up and looked into his eyes, then grabbed him, pulled him close, pressing him tight to her silk robe. He felt her large breasts against his chest, could feel her warm breath as her lips touched his, and then she pressed him tighter, her tongue flicking across his lips then parting them and pushing in to poke his tongue, dancing with it. He moaned softly, then his eyes widened. She was looking at him as she kissed him. He started to tremble in her firm grasp, the pain he felt from his cock attempting to swell inside the tight confines of the metal shell he now wore radiated through him in waves of agony.

His Boss broke the kiss and he felt her hand grasp the cage and she smiled at him, "Excellent, toy, hard ons and messy male orgasms are not something we will have to worry about now."

With a nod, she went turned and addressed Miss Stacey, "Take the toy on a run, two miles I think. Stretch him really good. We need him in tip top shape."

"Yes, Ma'am," Miss Stacey took the leash and led him off, still trembling. She grabbed a bag, and then led him outside. They walked down a short path to a building that stood next to the pool for changing, it also had a gym, and showers.

Inside, she checked his feet then got him a pair of socks and tennis shoes. As he put them on, she changed into a pair of shorts and a sports bra. The radiating pain from his caged cock continued as he watched his beautiful caretaker.

Stars flooded his vision then, and his cheek stung. He had paused watching Miss Stacy, still pulling on his socks. His vision cleared and he saw Miss Stacey glaring at him, "Why the fuck aren't your shoes on yet, bitch? Stop ogling me and get ready, we have lots to do!"

His cheek burned and he reached up, and just before he got to his cheek, she smacked his hand down, and hissed, "NOW!"

Tears had filled his eyes, but he quickly finished the socks and got the shoes on, and no sooner had he finished tying the second shoe, the leash jerked and Miss Stacey pulled him back outside after grabbing a backpack, and a couple water bottles.

She put the pack on him, and it felt a little heavy, but nothing he couldn't handle. She put the bottles down in the bag, then ran him through a few stretches. All too soon, they were jogging down a trail.

Within about 100 feet, he was struggling to breath, not used to running, and Miss Stacey had increased the pace. She relented some a bit later. The cage bounced with his cock uncomfortably, and he tried his best to put it out of his mind. This wasn't hard as his thighs and calves were burning after about 20 minutes.

A while later, they came to a small clearing, and Miss Stacey stopped and as he stood there panting, she took out a water bottle and took a long drink, then another. He stood and looked longingly at the water hoping she wouldn't forget him.

She didn't. Taking a long swig of the water, Miss Stacey grabbed the back of his head, pressed her lips to his and let the water trickle into his mouth from hers. It was oddly erotic and his cock tried once again to get hard and as he gulped the water down, nearly choking, he was realizing he was starting to handle the pain.

Soon Stacey stepped back and told him to stretch. She took the pack from him and sat down while he started stretching. She rummaged around and pulled a couple things out and motioned him over and told him to turn around and bend over.

Soon, he felt her applying a cool gel to his ass, then a finger inserted into him. He flinched, trembling as she steadied him with her other hand and worked his tight little hole,

He moaned, and started to pull away, but she had switched her grip to his balls and tightened her grip, "Don't move toy, Mistress told me to stretch you, and for the last half of our run, that is exactly what is going to happen. It will also help you to learn control."

He then felt a pressure and then a terrible throbbing pain as Miss Stacey pushed the plug deep into his hole, twisting it as she worked the thick part of the plug into his ass. "Now for the rest of the run, toy, you will not let that plug slip AT all. It should hold, you are tight, but, if you feel it start to slip, tighten your hole up, just clench it. If it should fall, I promise you will regret it, am I clear?"

He nodded, he believed everything this stunning redhead told him, and very much feared that he would be beaten if he failed. Nodding she took up the leash again and put the pack back on him, then they were running. For the last half of the run, Miss Stacey set a grueling pace, that not only had his muscles burning, his lungs gasping, but his ass was clenching so much every time he felt that plug moving and feared it was slipping out.

Then he saw the gym house, just a few more feet. Gasping he put his mind to just making it upright as Miss Stacey put on a burst of speed, forcing him to go faster. He was so close, he was going to make it, just as she began slowing down, and they were almost about to come to a stop he felt it, the plug moved, his ass loosened and he gasped and tripped falling down as the plug popped out and bounced on the ground as he fell and the leash jerked choking him as Miss Stacey turned around and stepped back towards him, her face a mask of fury as she saw the plug in the dirt.

Then, as he gazed up at her in terror, he saw something that he would soon learn was a very bad sign from any of the Ladies he would be serving, she smiled. Her next words she said almost gleefully, "Looks like NOW, I get to punish you!"

She made him pick up the plug and himself, then led him into the gym room, and unhooked the leash. Pushing him toward the showers, she turned the water on in one, and then undressed, motioning for him to kick his shoes and socks off. Once they were under the hot water, it felt so refreshing. The fear of the promised punishment seemed to counter act his seeing her naked again.

After washing off, they dried and she led him into the gym and bent him over a bench. "Stay," the command was simple. Picking up a thin rod, she just said, "Punishment time."

She just gave him ten strokes. The stinging strikes of the rod set his rear on fire. Tears filled his eyes and he cried out in pain. He could only hear his own screams for several moments even after the punishment had ended. Though shortly, he heard clapping. Blinking back tears he looked up and there was his Boss in workout leotards.

"Excellent, Stacey, dear. I assume he couldn't keep the plug in?"

"Actually, Ma'am, he did quite well right up until the last few feet, then he stumbled and it popped out as he fell. That's why I just gave him ten."

Nodding, his Boss walked closer to him and grasped his chin, tilting it up to look into his tear-filled eyes, "This is a very important lesson to learn, toy. Very important. Any disobedience will be met with the appropriate punishment. You will learn from your mistakes, toy. But each one will be punished."

He gulped, and nodded. She smiled and then kissed his forehead, giving him a pat on the head. Another woman walked in and she and his Boss went off to workout as Miss Stacey led him out and back toward the house for further lessons.

His mind whirled with everything. The feel of his Bosses lips on his forehead was wonderful, and he found he liked that small bit of phrase, and learned that he indeed wanted to please her, wanted to not make mistakes, and was actually looking forward to learning from those mistakes, even if it meant pain.

His ordeal was just beginning, but he found himself growing more used to the idea that his life was not going to be how he had imagined. He even began thinking, it may just turn out much better.