Sissy Stories: Chastity’s Unforeseen Path04

August 16, 2023

Adam continues to embrace his feminization training and delves into exploring deeper levels of submission and obedience. In a specialized boutique, he tries on various custom-made women’s lingerie and outfits, experiencing the sensuality and comfort they bring. Under the guidance of the attendant, Susan, he ventures into trying out various role-play costumes, including a maid outfit. However, his exploration doesn’t stop there. When Susan returns with a massive dildo, Adam’s boundaries are pushed to new heights once again. He’s instructed to kneel on a platform and learn to swallow the enormous dildo, marking his gradual acceptance of more rigorous training and obedience. This chapter will showcase Adam’s journey in exploring his gender and sexuality while gradually delving into deeper levels of servitude and submission.

Morning Chastity Encounter

to the new day. Emerging from the dog cage, he felt a sense of renewal and readiness for the challenges ahead. The blaring alarm clock startled him while he was sipping water from a dog bowl, but he managed to silence it swiftly. Collecting his thoughts, he stood up, performing a full stretch to invigorate his body.

With the day’s agenda in mind, Adam proceeded to his bathroom. He removed the panties and butt plug, pausing to glance at himself in the mirror. His body bore the marks of his training, both physical and psychological. The moment of reflection was fleeting as he got down to business. The butt plug was cleaned meticulously before being reinserted, and he completed his ablutions.

Stepping into the shower, he relished the hot water cascading over him, washing away any lingering traces of the night. As he emerged from the shower, he felt revitalized and ready to tackle the day. Drying off and wrapping a towel around his waist, he looked at himself in the mirror once more. The image reflected back was one of submission, a stark reminder of the path he had chosen.

Back in his bedroom, he reached for the cum-stained panties from the previous day. With a mixture of reluctance and anticipation, he put them on again. They had become a peculiar emblem of his journey, carrying both discomfort and strange arousal. He knew that he would soon replace them with new clothes, another step in his transformation.

The house was quiet as he descended the stairs, the weight of the upcoming tasks hanging in the air. The clock in the reception area showed it was 7:10 AM. Emma, the receptionist, was already present, her professional demeanor apparent as she meticulously prepared for the day’s activities. Adam’s heart raced slightly; the combination of the familiar routine and the unknown possibilities of the day created an intriguing tension.

Breakfast Duties and Unforeseen Requests

“Good morning, Adam!” Emma’s cheerful voice greeted him as he entered the reception area.

“Good morning,” he responded with a friendly smile before continuing down the corridor toward the dining room. Inside, he switched on the lights and headed to the kitchen. A note caught his attention, and he took a moment to read its contents:

“Good morning, slave,

Today you will prepare us a light breakfast of avocado on toast, some freshly squeezed orange juice, and a fruit bowl each. Please keep the table ready for 8 am for myself, mistress Grace, and make sure you make food for Emma as well. And make yourself some scrambled eggs and toast.

Mistress Alice”

Checking the time, he noted he had about 45 minutes to complete the task. He swiftly began his preparations by peeling oranges and squeezing fresh juice, his hands straining as he operated the manual juicer. Once done, he moved on to chopping strawberries, mangoes, raspberries, and apples for the fruit bowls. With 20 minutes left, he tackled the avocado on toast and his own scrambled eggs and toast.

As the clock neared 8:00, Adam felt a mixture of accomplishment and tension. He arranged the dishes on plates, ensuring their presentation was impeccable. With plates in hand, he entered the dining room to find his mistresses waiting. They sat facing each other, their presence commanding his attention. Adam approached mistress Grace first, placing her plate before moving to do the same for mistress Alice.

Back in the kitchen, he retrieved their drinks and then Emma’s food, anticipating her arrival. Adam stood, ready to serve the receptionist as he had been instructed. The familiar routine of these tasks was juxtaposed with the underlying sense of the unexpected that seemed to permeate his every action.

Unexpected Demands and Obedient Compliance

“Don’t just stand there, worm. Go and give it to Emma at her desk!” mistress Grace’s voice sliced through the air, urging Adam into action.

Caught off guard, Adam rushed to the door, his anxiety intensifying. Unbeknownst to him, mistress Grace muttered under her breath as he left, “Fucking useless idiot, we’ll have to punish him hard.”

Filled with a sense of dread, he entered the reception area clutching the plate of food and a glass of juice. Emma’s welcoming smile contrasted with his apprehension.

“Thank you, just pop it down here,” she said, her kind demeanor momentarily setting Adam at ease as he placed the items on her desk.

Returning to the dining room, his mistresses’ expectations hung heavily over him. He retrieved his dog bowl filled with food from the kitchen and settled between his mistresses to consume his own meal, all while kneeling on the floor. With a sense of urgency, he devoured the food, aware that the day ahead would be demanding.

Having finished, Adam sat up, awaiting further instructions. Mistress Grace broke the silence, reminding him of the schedule.

“It’s just gone half past eight. You’re going to quickly wash up the dishes first. Don’t worry about Emma’s. Then you’re going to go upstairs and put on the outfit we have left there for you and then come down and sit in the reception area and wait. Understood?” she questioned.

“Yes, mistress,” Adam replied.

“You will be there by 9 o’clock or you will be in trouble,” she warned.

“Good,” Mistress Alice added, her voice reinforcing the directive. “Go and wash these up now,” she instructed, piling the used plates.

In the kitchen, Adam efficiently cleaned and dried the dishes, leaving them spotless and ready for use. He returned through the dining room toward the reception area, each step a reminder of his submission to their commands. The next phase of his training was about to begin.

Transformations in Chastity Crossdressing

“That was a really nice breakfast, Adam, thanks!” Emma’s cheerful voice greeted him as he passed her.

“I’m glad you enjoyed it!” he replied with a genuine smile.

Ascending the three flights of stairs to his room, Adam’s eyes fell upon the neatly arranged outfit awaiting him on his mattress. A charcoal grey suit, white shirt, and a red tie were accompanied by polished shoes. He quickly changed into the attire, each piece fitting him as if tailored. Tying the tie took a bit of effort, but after a few tries, he managed to get it right. Adam’s reflection in the bathroom mirror was unfamiliar yet surprisingly appealing. He descended the stairs and arrived at the reception area, early by a few minutes.

Seated and waiting, Adam watched the clock tick past 9 without any sign of his mistresses. Just as doubt began to creep in, the rhythmic sound of heels on the stairs announced Mistress Alice’s arrival. Her appearance was stunning, adorned in a scarlet red wrap dress, red high heels, a black summer hat, and sunglasses. A handbag dangled gracefully from her arm, and her presence exuded elegance. As she approached, Adam stood up, unable to hide his admiration.

Mistress Alice addressed him, revealing a new aspect of his role.

“A part of your future responsibilities might not be sexual. Today, we’re going shopping for some clothes for you, but you’ll also be our chauffeur as we drive there,” she informed him while adjusting his suit jacket.

Mistress Alice moved toward the reception desk, where Emma sat.

“Emma dear, do you have the items I left here?” she inquired.

“Yes, Alice, here you go,” Emma replied warmly, handing over three items that were out of Adam’s sight.

A Drive of Transformation

“Thank you,” Mistress Alice smiled graciously at Emma, who returned the smile warmly.

She then turned her attention back to Adam, holding a hat in her hand. It was a chauffeur’s hat, and Adam realized its purpose immediately. With a simple gesture, she handed it to him, completing his ensemble. Next, she offered him a set of car keys.

“Let’s go,” she instructed succinctly, urging him toward the exit.

Adam opened the door, allowing Mistress Alice to pass through before he closed it behind them. Stepping onto the pavement, he paused for a moment to savor the sensation of fresh air. It was his first time outside the training facility since he had arrived. He took a deep breath, relishing the freedom it symbolized. Following Mistress Alice’s lead, he walked toward a parked car, noticing she was standing beside it. A quick press of the button on the key fob unlocked the brand-new Mercedes E-class. The car exuded luxury and prestige, and Adam was thrilled to have the opportunity to drive it. He eagerly made his way to the driver’s door and opened it.

However, his excitement got ahead of him, and he didn’t open the other doors for his mistresses.

“This door won’t open itself, Adam,” Mistress Alice sighed in mild disappointment, waiting patiently at the curb.

Adam’s face reddened with embarrassment as he quickly circled the car, opening the door for Mistress Grace. He realized his mistake and promptly corrected it.

“I’m sorry, Mistress Alice. I won’t let it happen again,” Adam apologized sincerely, opening the rear door for her.

“That’s right, it definitely won’t happen again,” Mistress Alice warned him with a hint of authority as she settled into the back seat of the car.

A Shopping Expedition

Adam closed the door behind Mistress Alice and settled into the driver’s seat. Adjusting the seat to his comfort, he fastened his seatbelt and waited for further instructions. Mistress Alice leaned forward from the back seat and handed him a small piece of paper.

“Take me to the first address, please,” she instructed him.

“Yes, Mistress,” Adam replied obediently.

The piece of paper contained three addresses, with the top one leading to a location in Chelsea, Manhattan. Adam entered the address into the car’s built-in navigation system and began following the route. The journey was quiet, punctuated by occasional glances at Mistress Alice through the rearview mirror. She seemed engrossed in her phone and occasionally emitted a playful giggle. As they approached the destination, Adam noticed a converted house that now functioned as a clothing store. Luck was on their side, as a parking spot awaited right in front of the store. Adam skillfully maneuvered the car into the space, turned off the engine, and stepped out.

He quickly circled the car and opened the rear passenger door for Mistress Alice to exit. With a graceful demeanor, she placed her phone back in her handbag and stepped out of the car. Adam closed the door with precision and locked the vehicle. He then walked toward the store and held the door open for Mistress Alice to enter. Following her inside, he took in the modern ambiance of the store. To the left were stairs leading upwards, while to the right lay an open-plan space with racks of trendy clothing. Brands like Calvin Klein, Ralph Lauren, and Lacoste caught his eye. Mistress Alice made her way to the payment counter, and Adam dutifully trailed behind her.

Becoming Susan's Obedient Slave

“Good morning! I’ve got an appointment for Adam here with Susan,” Mistress Alice informed the friendly cashier.

“Oh, of course! I’ll go and get her for you,” the cashier replied with a smile, disappearing through the staff door.

Shortly after, a lady named Susan emerged from the door, and Adam assumed she was the one he was here to see. Susan was a shorter, stouter woman, appearing to be in her mid-40s to early 50s. She sported a blonde bob haircut and a simple white t-shirt paired with denim jeans. She greeted Mistress Alice with warmth, shaking her outstretched hand.

“Alice, my dear, it’s wonderful to see you again!” Susan exclaimed.

“Likewise, Sue! It has been a while,” Mistress Alice responded.

Susan turned her attention to Adam, extending a cordial smile. “Tell me, what can I do for you, Alice?”

“I’ve written it all down here for you. I’ve got to go and run a few errands, but I trust you’ll sort Adam out for me?” Mistress Alice handed Susan a folded piece of paper.

“Of course, you leave him with me. I’ll sort him out,” Susan affirmed with a warm smile.

“Thank you!” Mistress Alice chimed. She turned to leave but pulled Adam aside for a brief moment. “You will do everything that Susan asks of you. If you do not, she will tell me, and you will be punished. As she isn’t technically your mistress, you can call her ‘Madam.'”

With those instructions, Mistress Alice made her way towards the store’s entrance and exited, leaving Adam standing with Susan and the cashier.

“Follow me, please, Adam was it?” Susan asked, already starting to move towards the stairs.

“Yes, Madam,” he responded respectfully, falling in step behind her.

As they ascended the stairs, Adam wondered what tasks awaited him under Susan’s guidance.

Sissy Transformation in Susan's Domain

As they ascended the staircase, they arrived at a door. Susan took a key from her jeans pocket and unlocked it. Adam followed Susan into the room, and she locked the door behind them. The room was filled with an array of clothes racks showcasing erotic garments, role play outfits, bondage gear, and various implements that were unfamiliar to Adam. In the center of the room stood a small platform.

“Please undress and stand on the platform in the middle. We’ll begin with your body measurements,” instructed Susan.

Adam walked to the platform and, while covering his caged penis with his hands, started removing his suit jacket and trousers. Near the platform were a couple of chairs, and he placed his clothes on one of them. After swiftly removing the rest of his clothes, he stood on the platform, his caged genitals discreetly concealed by his hands. Susan returned with a tape measure and a notepad.

Susan measured his upper body, jotting down measurements for his chest and stomach. She continued downward, taking measurements for his legs. Once his legs were measured, she moved in front of him.

“You’ll need to move those hands for me… don’t worry, it’s not like it’s something I’ve never seen!” she laughed. Adam reluctantly moved his hands to his sides.

“Well, that’s one incredibly small cage you’ve got!” Susan laughed, observing the compact cock caeg. Adam’s penis began to strain against the cage as it attempted to expand. “Oh my word, it’s attempting to grow! That’s quite amusing!” she laughed even harder while shaking the cage gently, intrigued by its small size.

She measured the length of the cock cage and noted it down on her notepad. Then, she measured his waist and completed a few final measurements, meticulously double-checking some of them.

“Perfect, follow me!” she commanded.

Adam followed Susan to the back of the room, opposite the door, where a spacious changing room awaited. Susan gestured for him to wait inside and left momentarily. She returned with a handful of brightly colored women’s clothing.

“These clothes are specially tailored for sissies, so let’s try a few on,” Susan informed Adam, handing him a lacy red bra.

Adam's Transformation and Seductive Attire

Adam found himself struggling for a minute as he attempted to figure out how to put on the lacy red bra. After some effort, he finally managed to interlock the straps. Susan then handed him a garter belt and stockings, which he adeptly put on. The sensation of the stockings against his skin made him feel surprisingly sexy, and he marveled at how comfortable they were. Lastly, Susan gave him a matching lacy red thong, which he slid into comfortably, noting that there was a bit more room in the front for his cock cage.

“Marvelous!” Susan exclaimed with satisfaction, pleased that the outfit suited Adam so well. “How does it feel? What do you think?” she inquired.

“It fits really well, actually. Quite comfortable. It makes me feel sexy, like a sissy boy,” Adam admitted.

“Perfect! That’s exactly the look we’re aiming for. I’m glad the clothes fit nicely.” Susan responded. “Oh, and let me offer you a bit of advice. As a sissy boy, it’s best to put on your panties after your stockings and garter.”

Adam looked puzzled, furrowing his brow in response.

Susan noticed his confusion and explained, “This way, anyone – man or woman – can easily remove your panties. If someone wants quick access to your rear, there’s no need to deal with the hassle of removing garter and stockings. The panties just slide off effortlessly.”

Adam nodded, comprehending the logic behind her suggestion. To illustrate, she tugged at his thong, and it glided to the ground seamlessly. She instructed Adam to remove the rest of the clothes. She returned with more items, and Adam found himself trying on various combinations and sets of tailor-made sissy lingerie. Surprisingly, he was growing to enjoy this experience. He had never realized how comfortable women’s clothing could be, and he relished in the soft materials that made him feel both comfortable and alluring. They progressed to skirts and dresses, and Adam was smitten with every piece he tried on. Most of them fit well, and Susan was pleased with their progress. They then delved into trying out roleplay outfits, and Adam found himself in a maid’s outfit. It fit him snugly, and he couldn’t help but fantasize about playing the role of a sissy maid.

As they moved to footwear, Adam faced a new challenge. Although he had never worn high heels, Susan handed him a pair of open-toe high heels. They were sleek and black, with a height he estimated at around 6 inches. Slipping into them, he felt their material against the mesh stockings he was wearing. As he stood up, he initially wobbled, adjusting to the new angle of his feet. After a few moments, he regained his balance and stood straight. Stepping into the main area of the room, he looked at himself in the mirror. From head to toe, he could have easily passed as a woman. The maid outfit had a frilly design that draped loosely around his figure. The stockings he wore underneath matched perfectly with the high heels, completing the ensemble. He examined himself and couldn’t help but feel aroused by how appealing his body looked in this outfit.

A Sissy's Journey Into Submission

“Isn’t it exciting?” Susan asked from the changing room.

“Yes, madam, the outfit is absolutely stunning!” Adam replied enthusiastically.

“I’m glad you like it,” she responded. “But there’s one more thing Alice has requested. She wants me to find you a sizable dildo to practice sucking on. Wait here a moment.”

Susan walked over to a shelf filled with an array of bondage gear, butt plugs, and dildos. She carefully selected one and returned to Adam, who looked both intrigued and surprised by its considerable size.

“This is a 13-inch dildo, Adam, with a girth of about 5 inches. It’s for your practice,” Susan explained.

She gestured for him to step onto the platform in the center of the room, and he complied without hesitation.

“Kneel,” she instructed.

Adam knelt down, and Susan placed the dildo on the platform in front of him, securing it with its suction cup. Using her measuring tape, she marked a spot that Adam couldn’t see, then took a pen from her pocket and made another mark about 8 or 9 inches down the dildo.

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