Sissy Stories: Chastity’s Unforeseen Path02

August 4, 2023

In the second chapter, Adam finds himself plunged into an intense training program under the strict guidance of Mistress Grace and her fellow trainers. As a complete beta male, he is subjected to various forms of humiliation and submission, including chastity training and learning to serve his future mistress in every way possible. With the pressure to please and obey, Adam faces challenges that test his limits and desires. The journey of self-discovery continues as he navigates the complexities of his new life and learns the consequences of disobedience.

Step into Chastity

Adam stood outside the three-story building, contemplating his unexpected future. The test results had opened doors he never imagined, allowing him to explore his inner desires. While surprised by the outcome, he saw the opportunity for financial security and a chance to embrace his submissive nature, retiring at 45 with a house and car.

Approaching the imposing wooden door, Adam took a deep breath and pushed it open, revealing a modern reception area dominated by pristine white decor. A young lady engrossed in a telephone call manned the desk. Adam patiently waited for her to finish.

The room’s ambiance felt both intriguing and nerve-wracking, and he wondered about the path that lay ahead as he stepped into the realm of chastity.

Embracing Mistress Grace's Guidance

“Hello, I’m here to see Trainer Grace. I’ve been sent by Lindsey,” Adam announced, handing the receptionist the piece of paper Lindsey had given him at the test center.

“Okay, I will let her know you are here. Please take a seat,” the receptionist replied, accepting the paper and pointing to the seats behind Adam. He nervously sat down, waiting for further instructions.

A few minutes later, the thumping of boots echoed down the stairs. Adam turned his head and was taken aback by the sight of Trainer Grace descending the staircase. She was a striking woman, 5″4 with an air of authority. Her black army boots, leather leggings, and minimal makeup exuded dominance.

“You must be Adam,” she said, her piercing blue eyes fixated on him as she approached. “Yes,” he replied, “Lindsey from the testing center sent me. She said I should report to you for client 12?”

Ignoring his question, Trainer Grace went straight to the receptionist, who handed her a notepad with some papers. She then turned back to Adam. “Follow me,” she instructed, leading him to an unknown destiny under Mistress Grace’s guidance.

Embracing Desires as a Submissive Servant

Up the stairs they climbed, Adam following closely behind Grace, enjoying the view of her enticing figure. At the top, they faced a choice of directions. Grace opened a door to the right and motioned for Adam to enter. The room was small, with only a wooden desk and three chairs squeezed in. Grace took a seat, and Adam chose the chair nearest to the door.

“Right, Adam. Lindsey sent you to me because you’re a complete beta male, is that correct?” Grace asked, her voice firm.

Adam, feeling more emboldened now, responded, “Yes, and I assume you’re Grace.”

She continued to ignore his acknowledgment and got straight to the point, “You’ve accepted your place in society, which is good. Now, we need you to sign these forms before we proceed with your training.”

She handed him a notepad and a pen. Adam scanned the documents, feeling a mixture of excitement and nervousness.

The first document stated that he must obey every instruction given by the training facility’s staff and that any breach of rules would result in punishment, with reasons for the punishment provided beforehand. Adam hesitantly signed it.

The second document specified that after completing the two-week training, he would become the servant of client 12, fulfilling her every request under the threat of punishment for non-compliance. He signed it, accepting his role.

The final document promised that on his 45th birthday, his contract with client 12 would end, and he would receive a two-bedroom apartment worth up to $750,000 and a car valued up to $75,000. The prospect excited him, and he eagerly signed it.

With the documents signed, Adam knew he had embarked on a life-altering journey, embracing his desires as a submissive servant to a powerful mistress named Client 12.

The Chastity Training Begins

He handed all three signed papers back to Grace, who had maintained a frosty demeanor. Grace checked the signatures before setting the documents aside. She then consulted a document on her notepad, keeping it out of Adam’s sight.

“Now that you’ve signed all three documents, you are bound to submit to every command from me or any other trainer here, or face punishment. Do you understand?” Grace’s tone was stern.

“Yes,” Adam replied simply, feeling a hint of fear at her reminder.

“Take off all of your clothes now, please,” she commanded.

Adam hesitated at the idea of stripping in front of someone else, but the intensity in Grace’s eyes left him with no choice. He quickly removed his jacket, t-shirt, shoes, socks, trousers, and finally his boxer briefs, placing them on the vacant chair. He stood there, vulnerable and exposed, waiting for her next instruction.

A grin stretched across Grace’s face, and her words pierced Adam like a dagger. “Lindsey mentioned your small penis, but my god, that thing is tiny. I wouldn’t even call it a cock,” she mocked him, sending a mix of embarrassment and arousal coursing through him. Thankfully, he managed to keep himself from getting erect.

From her desk drawer, Grace produced a strange metal object – a cock cage. Adam had seen these in some of the porn he had watched, and he realized that this was going to be a crucial part of his training.

The Advent of the Cock Cage

“This is a cock cage. It will prevent your penis from getting erect and stop you from masturbating. Lindsey mentioned that you jerk off 5 times a week, which is completely unacceptable. Put on the cage, and then we’ll proceed,” Grace instructed.

Adam spent around five minutes trying to figure out how to properly wear the device. After some trial and error, he settled on a ring that fit snugly around his penis. Placing the small cage over his manhood, he felt the pressure building inside. Once the cage was in place, he could no longer see his penis, only the constraining metal device

“Great!” exclaimed Grace as she rounded the table in one swift motion. She held the padlock but didn’t close it. “You could have been a bin cleaner or street sweeper, yet you chose to come here. You are about to begin your journey into servitude, and I want you to fully embrace it. When you are ready, close the lock,” she said.

Adam sensed a touch of sympathy in her words, but he knew he couldn’t back out now. He had signed the contract, and the consequences of refusing this unique opportunity were too dire. With a deep breath, he made his decision and clicked the lock shut, sealing his fate and surrendering to the start of his submissive journey.

Mistress Grace's Command

“Fantastic!” chimed Grace. “Now I’m going to go over some ground rules for your time here. Our client has requested a servant to be trained in 2 weeks, which means the program here will be very intense. Any resistance will result in severe punishment as we cannot afford to waste any time. Clear so far?” she checked with Adam.

“Yes, Mistress Grace,” he replied.

“Good. While I may be one of the trainers here, you do not get to call me that. You are a complete beta male, bottom of the pile. From now on, you will address me as ‘Mistress Grace’ or simply ‘Mistress’. Do you understand?” she clarified.

“Yes, Mistress,” Adam stammered. He had never had to call anyone “Mistress” before.

“Good. As for your name, I know that you are called Adam, but in all honesty, your future mistress isn’t going to call you by your name, so neither will we here. You’ll be called whatever we like. It could be ‘beta bitch,’ ‘slave,’ ‘piggy,’ ‘sub,’ or anything else that we want to call you. You will only respond to us if we ask you a question; otherwise, you will stay silent. Got it, bitch boy?” she asked.

“Yes, Mistress,” Adam replied.

“Good. Now I’m going to go over the training plan that will cover all aspects of servitude that need to be addressed before you go and live with your new mistress,” she said, glancing at Adam.

Adam remained silent, his mind spinning with the reality of what he had gotten himself into.

Mistress Grace's Training

Mistress Grace reached across the desk and grabbed the notepad. She looked down at the notepad before speaking. “You are going to be trained in housekeeping, chauffeuring, and cooking to start with. How do you get along with animals, bitch?” she asked.

“Good, Mistress Grace. My family used to have a dog,” he replied.

“Even better. Our client has a dog, so you will also be placed on dog walking duties when you are placed into her home. That’s the basics out of the way. Now I’m going to tell you about the sexual desires and training that your mistress would like you to undertake,” she said, a mischievous smile on her face as she scanned the lower part of the page.

Adam gulped, wondering what sadistic things he would be required to do.

“First and foremost, you will not have an orgasm while you are here. Your mistress does not believe that you need to cum. She thinks her slave will perform better when he is constantly horny,” Mistress Grace revealed, shaking Adam’s understanding of his own desires. He didn’t realize that the premature load he had spurted out earlier would be his last for at least two weeks.

“Next, we are going to focus on worshipping a woman. From foot worship and face-sitting all the way to bringing a woman to climax in the most sensual way possible. Your mistress is also quite cruel, and she takes pleasure in the humiliation of beta males. Your training will also include tease and denial, small penis humiliation, and elements of alpha/beta dynamics. Now your future mistress hasn’t requested it, but we may also introduce you to cuckolding and sissy lifestyles if we have the time. This will really impress your mistress in the future,” Mistress Grace finished.

Adam was shocked. He had not expected such extreme fetishes, and yet as he heard Mistress Grace reciting this, he couldn’t help but become aroused in his little cage. The journey of submission had truly begun.

Male Humiliation Trainin

“I am in charge of the beta male humiliation training here, and we will get underway with some light training shortly. You will also meet Mistress Alice later, who is our in-house female worship specialist. She will train you in how to please a woman. We also have Mistress Veronica, who is a punishment specialist. All three of us women, however, can administer punishment where necessary. Now, let me show you to your room,” Mistress Grace said, standing up and beckoning for Adam to follow.

Adam stood up and made to pick up his clothes that were sitting on the third chair. His action was immediately interrupted.

“Did I tell you to fucking touch those clothes, you idiot?” Shouted Mistress Grace.

“No, Mistress. Sorry, Mistress,” mumbled Adam. He stood there frozen, not knowing what to do.

“Kneel, you maggot,” she instructed.

Adam got down onto his knees immediately, not wanting to enrage his new mistress further. Out of nowhere, she slapped him across the face, hard.

“Thank me for that, you bitch!” she demanded.

“Thank you for slapping me, Mistress Grace,” he replied, defeated.

She slapped him nine more times, each time harder than the previous. She waited each time for him to thank her before she struck him again. After the tenth strike, she told him to stand up. She got as close to him as she could, and he could smell her perfume from where he was.

“You are a beta male. You are nothing. The next time you disobey my orders, it will be fifty slaps. Got it, prick?” she asked.

“Yes, Mistress,” he responded, completely defeated, his eyes fixed on the ground.

“I’m glad you understand that. Now, follow me,” she instructed.

Baptized as a Chastity Slave

Adam left his clothes this time, terrified of another 50 slaps to his already red face. He followed Mistress Grace out of the room. They headed down the corridor and up the flight of stairs at the end of the corridor, to the highest floor of the building. On the top floor, there was a door to the right and a door at the end of a corridor to the left. Grace walked down the corridor to the door on the left, and Adam followed suit. She opened the door to reveal what would be his bedroom for the next two weeks.

The room wasn’t too big, roughly 4×4 meters, and it had a very simple layout. On the opposite wall to the door was a fairly large window that overlooked a small garden area. In the left corner, under the window, was a simple mattress that looked slightly stained. Next to that was a cage that looked like it would be better suited for a dog. There was a single light bulb that floated above the center of the room, a round clock on the otherwise blank left wall, and one small cabinet on the right-hand side of the room near the entrance, with a small table next to it. The only other thing in the room was a dog bowl, next to the cage, filled with water. The name on the dog bowl simply read ‘bitch’. There was a door on the right-hand side of the room, leading to a small ensuite bathroom that both of them could barely fit into.

“It’s half past 12 now. I’ll give you some time to get settled in before lunch,” said Mistress Grace. “You will drink water on your hands and knees. You will lap it up like the bitch dog you are if you ever want some. Now, spend half an hour shaving what little body hair you have. There is also a pair of underwear for you in the wardrobe if you want to wear them, it’s completely optional. At 1 o’clock, I expect you to be downstairs at reception, and we will have lunch. Today it will be prepared for you, but from tomorrow you will be cooking all of the meals, not just for yourself but all three trainers and the receptionist. Understood?”

“Yes, Mistress Grace,” Adam replied. Having lived with his parents for most of his life, he had never really learned how to cook until he moved across the country to New York, and even then, he mostly ordered takeaways. He was nervous at the thought of having to cook for five people.

“Good, there is a camera in here that will monitor you, so don’t try and do anything you shouldn’t be doing. See you downstairs at 1 o’clock sharp, beta bitch,” she stated before swiftly leaving the bathroom and then the bedroom, closing the door behind her.

Preparation and Humiliation

Adam stood naked in the bathroom apart from the new chastity device that locked his penis away from sight. He decided that there was no point wasting any time and moved closer to the sink. He saw three disposable razors as well as a small can of shaving gel. He opened the can and squirted a small amount of gel into his right hand. He applied it to his underarms and crotch region as well as some on his upper legs. He took one of the razors and began slowly scraping away the hairs from his skin. Adam was fortunate that he wasn’t very hairy, and within 15 minutes, he was complete. He stepped into the shower and spent 5 minutes rinsing his body in lukewarm water. He dried off with a towel that was hanging over the shower door.

Figuring he needed to be downstairs in 10 minutes, Adam decided to check out the room. He stepped out of the bathroom and nearly tripped over the water bowl. Luckily, it didn’t fall, but as he saw it, he was reminded of how thirsty he was; he hadn’t drunk all day. Remembering what Mistress Grace had told him about the bowl, he quickly knelt down and then placed his hands on the ground as well. The carpet was slightly rough and a little uncomfortable but not completely unbearable. Adam stooped his head low, and his lips met the cool water in the bowl. It was very hard to slurp up the water like this, and Adam was glad that no one was around to watch him drinking.

He sat up on his knees and glanced at the clock. It read 12:54. He stood up and was about to leave his room before he remembered that there was some underwear in the wardrobe for him. He was glad about this and opened the door to the wardrobe. Inside, he was met with an empty cupboard, except for a pair of bright frilly pink panties at the bottom of the drawer. He was shocked at this and he didn’t know if he wanted to wear these humiliating panties; he had expected some boxer briefs or at least some male underwear. He decided against wearing these panties, closed the cupboard door, and left his room.

Adam descended the stairs quickly and arrived at the reception area, only this time he was completely naked, bar the cock cage that had since been put on. He felt extremely vulnerable standing in front of the reception desk completely naked. He was able to see behind the desk, however, and could see a small corridor which split left and right. He was also able to scrutinize the receptionist, whose nametag made out to be “Emma”. Before he could gawk at her any further, however, he was interrupted by Mistress Grace coming out of the right turn in the small corridor behind the receptionist’s desk. She looked slightly disappointed.

Lunchtime Humiliation

“I see you chose not to wear any underwear for lunch,” Mistress Grace said.

“No mistress. I thought they would be more… masculine?” Adam questioned nervously.

“Did I fucking tell you to speak worm? I didn’t ask you anything, so you keep that mouth shut,” she replied aggressively.

“The underwear were a test, to see if you would voluntarily submit. You failed the test. In the future, your mistress might not say anything but will expect you to understand her needs. You will be punished in some way, but you’ll find out about that later. Now follow me, it’s time for lunch.”

They entered a medium-sized room with a picnic table set for two. Mistress Grace sat down in front of her covered plate. Adam stood, awaiting further instructions.

“Come here and remove the covering for me then, bitch,” Mistress Grace demanded impatiently.

After revealing her plate filled with delicious Indian curry, she commanded, “Now remove the covering on your plate, please.”

Adam uncovered his plate to find a simple cheese and ham sandwich, feeling disappointed and hungry.

“Now, I told you that you failed the underwear test, and I did say that you would face a small punishment, didn’t I, slave?” Mistress Grace asked.

“Yes, mistress,” Adam replied meekly.

“Bring your plate around and place it on the floor here, next to me,” she instructed.

Adam complied, setting his plain meal on the floor next to his mistress.

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