The Training Facility, Wednesday July 1st, 2037, 6:27 AM

Adam stretched in the dog cage before rubbing his eyes and adjusting to the light that had filled his bedroom with a warm glow. He had slept very well and felt relaxed and refreshed, ready for another day of training. He crawled out of the cage and stretched properly again. He began drinking from the dog bowl that was on the floor but was interrupted when the alarm clock started blaring its siren. The volume startled Adam as he drank, but he crawled over to the alarm clock and silenced it with the press of a button. Adam took a moment to compose himself before standing up and stretching again. He remembered that he had to prepare breakfast by 8:00 am. He made his way into his bathroom and removed his panties and butt plug and used the toilet. He then washed the butt plug, lathering it in soap and giving it a thorough clean. He then took the bottle of lube out of the mirror cabinet before bending over the sink and slowly reinserting the plug into his ass. He then washed his hands thoroughly before brushing his teeth.

Adam then clambered into the shower unit and turned the water onto the hottest temperature. Ten minutes later Adam stepped out of the shower, drying off before he did so. He reached down for the cum stained panties from yesterday's adventures and quickly put them back on. The panties were harder now, having become crusty from all of the precum he had wiped with them yesterday. He was glad that he would be buying new clothes later in the day. He made his way downstairs, embracing the silence of the house. As he reached the reception area, he noticed the clock which read 7:10. The receptionist Emma was sat in her chair, brushing the shoulders of her business shirt down.

"Good morning Adam!" she called.

"Good morning." Adam replied with a smile.

He moved past the reception desk and down the corridor towards the dining room. He entered the dining room and turned on the lights before moving towards the kitchen door. As he entered he flicked the lights on. He saw a piece of paper next to the kitchen sink and moved to read it. It read:

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

As he finished reading the note, he checked the clock and saw that he had around 45 minutes to prepare breakfast. He started rifling through the cupboards until he found a packet of 6 oranges. He then scanned for a blender but realised there wasn't one. He found a peeler and began peeling the oranges before he found a boxed juice squeezer. He used the minimal strength he had to squeeze the juices out of the oranges. This took a while as he wanted to ensure that all three glasses were filled. After finishing this, he found more fruit in the fridge and began chopping up strawberries, mangoes, raspberries and apples. He placed these into three separate bowls. He had left himself 20 minutes to complete the avocado on toast and make himself his own breakfast. He quickly began on the eggs and when he saw that it was ten to eight, he began toasting the bread. At 8:57 his cooking was complete. He waited a moment, checking each of the dishes to ensure that they were prepared properly. He then grabbed two plates and made his way into the dining room. His mistresses were sat there waiting for him. They sat opposite each other and Adam moved to mistress Grace first, placing his plate in front of her before moving around the table to place mistress Alice's plate in front of her as well. He scuttled back to the kitchen and brought out their drinks before fetching the receptionists food. He stood in silence, waiting for Emma to enter the dining room.

"Don't just stand there worm, go and give it to Emma at her desk!" mistress Grace exclaimed.

Adam not realising that this was required of him hastily made for the door.

He heard mistress Grace mutter under her breath as he left "Fucking useless idiot, we'll have to punish him hard."

Fearing his punishment he quickly made his way to the reception area carrying the plate of food, with the bowl on it and juice in his other hand. He saw Emma sitting at the desk and approached from behind her. Hearing him approaching she turned around, while brushing some papers away from her desk.

"Thank you, just pop it down here" she said, giving him a warm smile as Adam placed the plate and glass of juice down.

He returned to the dining room in silence, before quickly entering the kitchen and grabbing his dog bowl of food off the counter, before returning to the dining room. Adam placed his bowl of food on the floor, between his two mistresses and began eating, on his knees. He quickly ate the food, knowing that the day was going to be very long and busy. He quickly finished his food before sitting up and awaiting further instruction. Mistress Grace spoke first.

"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 asked.

"Yes mistress." Adam replied.

"You will be there by 9 o'clock or you will be in trouble." Mistress Grace threatened.

"Good" Mistress Alice chimed in, "go and wash these up now" she said, piling her and mistress Grace's plates onto each other.

As he scuttled into the kitchen, his mistresses left the dining room, heading back towards the reception area. He washed the dishes fairly quickly, taking only ten minutes to do so. He then dried the dishes and put them back in the cupboards where they came from. He left the kitchen, turning off the light as he did. He moved through the dining room and back towards reception.

"That was a really nice breakfast Adam, thanks!" Emma chimed as he walked past her.

"I'm glad you enjoyed it!" he smiled back.

Adam climbed the three flights of stairs quickly and entered his room. As soon as he entered he saw a suit on his mattress. It was a charcoal grey suit, which was sitting in it's suit bag on his mattress. Next to the suit was a white shirt and red tie. On the floor were a pair of shoes with a sock stuffed into each shoe. Adam had nothing to strip off luckily, so started with the white shirt. He unfolded it and put it on. He found that it fit his body fairly well. He then put on the suit trousers which were a perfect fit again. He realised that they must have taken his clothing size from the clothes that he initially came to the training facility in. Adam had never been good at tying ties, and he fumbled about with the red tie in front of his bathroom mirror for a few minutes before he had got the length and knot looking good. He put the socks and shoes on before donning the jacket. He felt comfortable in this and thought that he looked good as he gave himself the once over in the bathroom mirror. He then left the room and descended the stairs to the reception.

The shoes were quite firm, and he guessed that all of the clothes were new, hence why the shoes felt a little firm. As he reached the reception area, he checked the clock and saw that he was early by five minutes. Adam took a seat in the reception area and waited. The clock struck 9 and went past and Adam wondered if he had misheard the instructions that were given to him. As if on cue, Adam heard the click clack of heels walking down the stairs. Mistress Alice appeared from the turning in the stairs and Adam was taken aback with how stunning she looked. She was wearing a scarlet red wrap around dress with open toe red high heels. She also wore a large black summer hat and she had covered her eyes with a pair of sunglasses. She also had a handbag over her right arm and she wore her whole outfit effortlessly in breathtaking fashion. Adam's expression was easily readable and mistress Alice giggled a little as she ascended the final steps. She walked up to Adam who stood up as she approached him.

"A part of your role in the future might not be sexual. Yesterday you experienced what it was like to perform cleaning duties all afternoon. Today, as you know, we're going shopping for some clothes for you! But you are also going to be the chauffeur as we drive there today." She informed him, as she smoothed out a tiny crease in his suit jacket.

Mistress Alice moved towards the reception desk where Emma sat.

"Emma dear, do you have the items I left here?" she asked kindly.

"Yes Alice, here you go." Emma replied warmly, handing mistress Alice three different items which Adam couldn't see from his position.

"Thank you" mistress Alice smiled back at Emma.

She turned back to face Adam, and he noticed a hat in her hand. Adam quickly realised that it was a chauffeur's hat. She handed it to him, and he instinctively put it on, completing his outfit. Next she handed him a set of car keys.

"Let's go." she instructed simply, ushering him out of the door.

Adam opened the door and allowed mistress Alice through before closing the door behind him. He climbed down the few steps and onto the pavement. It suddenly struck Adam that this was the first time that he had stepped out of the training facility since he had first arrived. He took a deep breath, welcoming the crisp morning air into his lungs. He turned to the left and followed mistress Alice to a parked car that she was standing near. He looked at the car keys and clicked the button on the fob, unlocking the car. The car was brand new, a Mercedes E-class. It signalled wealth and importance and Adam was excited to be given permission to drive the car. He rounded the car to the driver's door excitedly and opened it.

"This door won't open itself Adam." Mistress Alice sighed in disappointment, waiting at the kerbside.

Adam flushed red as he quickly rounded the car, opening the door for mistress Grace.

"I'm sorry mistress Alice, that won't happen again." Adam apologised as he opened the rear door of the car.

"That's right, it definitely won't happen again." Mistress Alice warned him as she lowered herself into the back seat of the car.

Adam closed the door gently behind her and made his way to the drivers seat. He closed his door and began adjusting the seat , moving it forward to bring him closer to the steering wheel. Once he was comfortable, he fastened his seatbelt and awaited further instructions. Mistress Alice leaned over from the opposite seat behind him and handed Adam a small piece of paper.

"Take me to the first address please." She instructed him.

"Yes mistress" Adam replied.

He saw that there were three different addresses on the piece of paper. He looked at the top address and saw that it was an address in Chelsea, Manhattan. He punched the address into the cars built in sat nav and began following the route. He drove in silence, occasionally glancing at mistress Alice in the rear view mirror. She was on her phone and occasionally giggled. As they approached the address, Adam saw that it was a house that had been converted into a clothes store. Fortunately, there was parking right outside the front of the store and Adam navigated the car into the space. He turned off the engine and got out of the car. He rounded the vehicle and opened the rear passenger door for mistress Alice to step out. She tucked her phone back into her handbag before climbing gracefully out of the car. Adam closed the door firmly behind her before locking the car. He then walked towards the store and opened the door for mistress Alice to enter. He followed her in and was met by a modern looking store, with stairs leading upwards on his left and an open plan store to his right, filled with racks of clothing. Most of the clothes were quite trendy and some of the brands he noticed included Calvin Klein, Ralph Lauren and Lacoste. Mistress Alice walked to the payment counter and Adam followed her.

"Good morning! I've got an appointment for Adam here with Susan." Mistress Alice informed the young cashier.

"Oh of course, I'll go and get her for you!" The cashier smiled and turned to the door marked staff behind her.

She soon emerged with a lady that Adam presumed was Susan. Susan was a short stumpy lady and Adam guessed that she was around 45 to 50 years old. She had a blonde mum bob and was wearing a simple plain white t-shirt and some denim jeans. She smiled at Alice before she spoke.

"Alice my dear it's wonderful to see you again!" Susan said as she grasped mistress Alice's outstretched hand.

"Likewise Sue, it has been a while!" she exclaimed.

"Tell me, what can I do for you Alice?" Susan asked.

"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?" she asked as she handed Susan a folded piece of paper.

"Of course, you leave him with me, I'll sort him out." Susan smiled warmly at Alice.

"Thank you!" Mistress Alice chimed. She turned to leave but pulled Adam away from Susan for a 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 that, mistress Alice made for the entrance and left Adam standing in the store with Susan and the young cashier.

"Follow me please, Adam was it?" asked Susan as she began walking towards the stairs.

"Yes madam" he told her, following her up the stairs.

As they reached the top of the stairs they were met with a door. Susan extracted a key from her jeans pocket and unlocked the door. Adam followed Susan who closed and locked the door behind him. The room was filled with a vast array of clothes racks containing erotic clothing, role play outfits, bondage restriction gear and various other implements, many of which Adam hadn't seen before. In the middle of the room was a small square platform.

"Take off your clothes and stand on the platform in the middle please, we'll start with your body measurements." Susan instructed Adam.

He walked to the middle of the room and began taking off his suit jacket and trousers. There were a couple of chairs near the platform and he placed his clothes on one of the chairs. He had quickly removed the rest of his clothes and as he was removing his panties Susan returned with a tape measure and a notepad. Adam moved and stood on the platform covering his caged penis with his hands. Susan began measuring his upper body, reaching around his chest and stomach and noting measurements as she went along. She continued downwards and was measuring Adam's leg length. Once she had measured his legs she moved in front of Adam.

"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 as Adam reluctantly moved his hands to his side.

"Ok well that is one hell of a small cage!" she laughed harder at this and Adam began to grow in his cage. "Oh my word it's trying to grow! That's hilarious!" she laughed even more as Adam's cock began to strain the confines of the cage. Susan grabbed at the cage, shaking it gently, fascinated by how small it was.

She began measuring the chastity cage length and noted it down on her notepad. She then measured his waist before completing a few final measurements which she double checked and in some cases, triple checked.

"Great follow me!" she commanded.

Adam followed her towards the back of the room, opposite the door, and found that there was a large changing room. Susan ushered him in and told him to wait there. She left and soon returned with a handful of brightly coloured women's clothing.

"Ok, these clothes have been specifically tailored for sissies, so let's try some of them on" Susan informed Adam, as she handed him a lacy red bra.

Adam had no idea how to put this on and struggled for a minute before the straps finally interlocked. Susan then handed him a garter belt and stockings. Adam put the garter belt on and then slid the stockings up his legs. They made him feel very sexy and the thin mesh material felt very comfortable. Finally, Susan handed Adam a matching lacy red thong. He slid into it comfortably and found that there was slightly more room in the front of the thong for his cage to fit in.

"Wonderful!" exclaimed Susan, delighted that the outfit fit Adam well. "How does it feel? What do you think?" she asked Adam.

"It fits great actually, really comfortable. It makes me feel sexy, like a sissy boy." Adam told her.

"Perfect! That's what we're trying to achieve here so I'm glad that these clothes fit well." She told Adam. "Oh and let me give you a little bit of advice. As a sissy boy, I would always recommend you put your panties on after your stockings and garter."

Adam was puzzled at this and furrowed his brow at her remark.

She read the confusion from his face before speaking. "It's so that any man or woman can easily take off your panties. If they want to get to your ass quickly then there's no hassle of taking off the garter and stockings as well. The panties just slide effortlessly off!" she told him.

This made sense to Adam and to demonstrate, she pulled at his thong and it fell to the ground seamlessly. She told Adam to remove the rest of the clothes. She brought some more back and soon enough Adam was trying on various combinations and sets of tailor made sissy lingerie. He was growing to enjoy this. Adam had never realised how comfortable women's clothing felt and he was in love with the soft materials that were able to make him feel sexy. Soon they moved onto skirts and dresses and Adam was loving every piece of clothing that he put on. The majority of them fit well and Susan was pleased at how well this was going. They then began trying out some of the roleplay outfits and Adam was thrust into a maid's outfit. The outfit fit well, and Adam was turned on with the thoughts of cleaning a house like a sissy maid that he could be. Finally they moved onto footwear. Adam being a male had never worn high heels and yet he was thrust into the deep end, as Susan handed him a pair of open toe high heels. They were black and Adam guessed that they were 6" in height. He slipped into them, feeling their material through the mesh stockings that he was wearing. He stood up and wobbled as he adjusted to the new angle that his feet were at. He hobbled around for a few moments before he composed himself and stood up straight. He walked into the main area of the floor and gazed at himself in the mirror. From face down, he could easily have passed as a woman. His maid outfit was frilly and hung loosely around his figure. The stockings he was wearing underneath matched with the high heels that he had just worn, completing the outfit. He checked himself out and was turned on at how good his body looked in this outfit.

"Sexy right?" Susan asked from the changing room.

"Yes madam, the outfit is amazing!" Adam chimed.

"Good, I'm glad you like it." She replied. "There is one more thing though. Alice has asked me to find you a huge dildo to suck on, wait here." She said.

Susan moved to the shelf where there were an assortment of various bondage gear, butt plugs and dildo's. She picked one out and took it off the shelf. As she brought it back to Adam, his eyes widened at its sheer huge size.

"This is a 13 inch dildo Adam, and it's got a reasonable 5 inch girth! All for you to practice sucking on!" Susan informed him.

She motioned for him to move onto the platform in the middle of the room and he complied.

"Kneel." She commanded.

Adam knelt and she placed the dildo on the platform in front of him, the suction cup sticking the dildo in place. Susan used her measuring tape to measure a length that Adam couldn't see from behind her. She then took the pen that she had been using to note down Adam's measurements and made a mark on the dildo, about 8 or 9 inches down.

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