Chapter 5:
Derek had cried his eyes out. It had been devastating on so many levels. Emma had dressed him up in his favourite dress, pretending like everything was normal when Jake had surprised the unexpecting sissy. Derek fell over in shock as Jake towered over him, laughing sadisticly as he revealed himself as Emma's well hung boyfriend.
"I've spent some 'quality time' with your mother, Helen." Jake explained. "She's very disappointed in your babyish behaviour".
"This house? It's mine and Emma's." "So is CareApp". "Your mother have the power to make it so, and she's happily agreed to do so." Jake kept his eyes fixated on Derek, in a display of dominance.
Derek had felt a feeling of utter doom in the pit of his stomach. He felt so utterly silly and stupid, not just because the way he was dressed, but because of the mess he'd gotten himself into.
Sitting on the floor in a childish dress with his legs forcefully splayed apart by his diaper in the presence of this strong, hairy masculine man was a horrid experience.
No one in the world would believe that they are the same age when the contrasts of these two males were total. One was tall and confident, another cowering on the floor, looking like a tearful child, who's clothes would suggest an age of two or three, while face and body would suggest an underdeveloped 14-15 year old.
"Your mother was kind enough to demand that you get to stay in the house", "I suppose you can keep your little nursery I've heard so much about" Jake added.
"She also insisted on giving you a new role within the company", "Also reasonable considering how.. 'unemployable' you really are, since any future employer calling for a reference would get the full and honest truth about you".
"Don't worry, I'm sure we'll find a more suitable work-role for you, baby.." Emma cooed in mock conselation, ending the conversation.
**TWO DAYS LATER**
"You got what you wanted, Derek.." Helen had said.
"No mother! I regret everything!" He pleaded, to no avail.
"You begged to be treated like a child, chastised, emasculated. You wanted to lose control, well, now you got it." She said in a manner of disbelief.
"You've certainly made a spectacle out of yourself, and as you make your bed you shall lay, as they say" Helen cheerfully said, clearly enjoying teasing her disappointment of a son.
"Aren't they generous? to let you stay in the house, in your cute little nursery, with all your toys and dresses and.. what not.." Helen looked around the room, finding it difficult to find many positives.
They were alone in his nursery, his walls had been painted pink, the inflatable crib had been surprisingly silly, Helen had thought. A rocking horse was in the corner. No computer, no cellphone, no newspapers. No whiskey... Helen dreaded the thought.
Emma was waiting outside, giving them space for their 'family time'.
"But Mother! Please take pity on me! They tricked me!"
"Oh, I do pity you, Derek little.. but you fooled yourself more than anyone, and you have only yourself to blame".
Helen was a bit ashamed that she got a sense of satisfaction as tears welled up in the eyes of her emasculated son standing in front of her, dressed in nothing but a thick diaper, a ruffled onesie, ruffled socks and his Mary janes, making his fists into a little balls of anger.
She knew he was too much of a coward to resist.
"Don't worry honey, your new boss Jake is even letting you stay at the company, just not in a leadership position obviously". "Tea boy I think he said".
"I encountered one when I was in business in Qatar a few years ago if I remember correctly" Helen mused.
"It wasn't particularly dignified, even for a pre-teen child as it just so happened to have been. "Pouring tea and coffee, changing toilet rolls, sweeping floors and shaking rugs.
"What self-respecting person would work a job like that?" She shrugged.
Helen wished she could witness his first day back, as she invisioned him submissivly and shamefully submitting to all kinds of embarrassing tasks, cursing her business-schedule which meant she would be out of town.
"They even kept all the staff, I guess the programmers you hired almost quit in embarrassent for you, but when offered equity and a chance to make career and a fortune they of course stayed, people always do".
Helen heard the faxing machine downstairs. "That must be it!"
They hadn't been able to formally transfer ownership or change the work-titles yet, with a weekend in between and all.
"Here we go.. Helen said as she was reading the papers handed to her by Emma. The first was just the clause to give Helen ownership, she would sort out the equity-swaps later.
The second paper was the more interesting to her.
"The only way they'll let you stay here is if you agree to your new role in the company.." Helen didn't know if it was true, she just wanted Derek to believe it, and he did.
"Ah, 'Junior Tea Boy' isn't that an appropriate role for you, Derek?".
"P-please mother, please don't do this! I promise I'll do anthing!". Derek desperately pleaded, he couldn't bear the thought of having to go back to his old company, knowing it was no longer his, knowing that the staff knows about his diapered, chaste sissy life at home.
He couldn't bear the thought of being ordered around by Jake, being laughed at by the staff. He felt a surge of pee enter his thick, thirsty diapers from just thinking of such a horrid reality.
"I know, I know Honey.. It's just that I really can't trust you with anything, anymore, how could I?"
"You put my reputation on the line, my money on the line because you are too much of a god damn sissy to control yourself, got it?" Helen was aggressive in her tone.
That was all it took to reduce Derek to a blubbery mess in front of her.
"At least you'll get to look like a boy at the office! isn't that good news?"
"I mean, Emma showed me your work outfit, I must say it exceeded my expectations by quite a bit.." Helen laughed at the sight of Derek's nervous reaction.
Derek, the former CEO, walking around, in a short romper style sailor suit, of course thickly diapered under.
"There were even some ruffles at the bottom" Helen looked at her son, who meekly looked down at his shiny black shoes, eyes and cheeks red and swollen from crying.
"It will go perfect with the shoes you are wearing right now!" Helen smiled.
"Imagine how comfortable the clients will be knowing that a baby-faced boy like you are there to politely greet them with an obedient curtsy, hang their coats and make them tea. It will feel so exclusive to have a well-mannered little Tea boy at full attention, ready to serve!". Helen laughed at the ridiculus sight as she imagined it, she figured it would certainly be a unique and interesting experience for clients there for meetings or business.
"Say it isn't so, Mother! Say there is a way out of this for me!" Derek had once again summoned up the courage to look at his mother to plead.
"Oh, but it is so.. Derek.. I hear a lot of secrets, I heard a lot of secrets last night when Jake shoved all his 8 inches inside me."
Derek froze in humiliation. He absolutely hated the thought of his worst enemy having sex with his mother.
"Emma doesn't mind that Jake gets a little action on the side, I don't either" Helen laughed, aroused at the thought of Jakes young brutish virility.
"Did you hear of Emma's success?" Helen had set up a couple of meetings with potentional clients, pleased to find out she had landed several of them, on her first day in sales.
"Aren't you proud that a strong woman like her is doing more in her first day than you ever did?". Derek knew he was being teased but Emma was the one person in all of this he didn't mind being successful, being in a dominant
position over him, even though she had clearly betrayed him. It was mixed feeling all around concerning Emma but Derek knew deep within that he was hopelessly in love with her.
"Last chance, sissy".
"Signing this paper will mean that you have officially accepted your demotion from CEO to Junior Tea Boy, and that you agree to your work-terms and dresscode."
"Or you can resist... Tell us all to go fuc-k ourself, start over from scratch in the streets but with your dignity intact, somewhat at least." "What's it gonna be, Tea Boy?"
Derek so desperately wanted to resist. He would occationally imagine himself standing up for himself and taking back control of his life. None of those imaginations included him crying and wetting himself. None of those included him shaking with fear at the mere thought of being outside in L.A after midnight.
Helen and Derek both knew he would take the path of least resistance, a path further down the rabbithole of endless shame. He gave in. "There we go, all signed and official."
"As far as the state of California are concerned, as well as us, you are no longer owner and CEO of 'CareApp inc', you are instead demoted to the newly intruduced role of 'junior Tea Boy'!" Helen laughed at his defeat, her sadism trumping any motherly love she'd have for him if he wasn't a total failure.
"Anyway, babyboy. I'll leave you here with Jake and Emma, I'm far too busy to stand around in your nursery all day".
Helen scoffed, as if disapproving of the ridiculusly childish room, for she had never once set foot in a nursery this femininine and childish.
--
Derek stood next to his crib, knowing it would soon be time for bed, it had been 6:30pm when his mother had come over to the house and he figured it must be nearing his bedtime of 7pm.
He had to pee. He wanted to fight that too. He wasn't getting incontinent, at least he didn't think so, but after spending over a week, constantly diapered, his bladder had gotten used to almost instant relief. Whereas most people could hold it for hours if needed, Dereks bladder, even half filled, caused him almost unbearable discomfort after only a few minutes.
He wasn't sure if his chastity played a part, deciding not to ponder the question since he had no way of getting it off.
He heard Emma and Helen talking downstairs, unable to make out what they were saying, but figured they were happy since he heard them laugh. "Are they laughing at me?" he thought so.
Derek peaked out the window to see Helen exit the driveway in her Bentley.
The door sofly squeked as Emma slowly opened it, as if trying not to startle whoever is inside, in this case, Derek.
He felt a little guilty standing over by the window, as if he'd been caught spying on someone. He wasn't in trouble, Emma didn't think anything of it but Derek was getting paranoid of accidentally 'earning' himself a hard spanking.
"Hi there, honey.." Emma almost whispered. She was carrying a neatly folded clothing garment. "Hi, Ma'am." Derek answered back, remembering the rules in addressing people. 'Ma'am' for female and 'Sir' for man, except for Jake, he was to be addressed 'Master Jake'. He cringed at the thought of having to address his former employee in such a superior manner.
"Jake is working late at the office, it's pretty hectic right now since the rapid growth in business" Emma said, she continued "We're even hiring more staff to keep up!".
Derek had dreamed of such a scenario not long ago when he had been the owner but unable to make it happen, now he desperately wanted the business to fail miserably since he had it taken away from him, only to see it flourish.
"Speaking of which, tomorrow is your first day as Tea boy!" Emma couldn't help but giggle as she said it, he would look so silly!
Derek got so incredibly nervous at the mere thought, he dreaded the moment. He remembered the feeling of going to school for the first time. All he wanted was to stay, safely in his nursery, hidden from the world.
Emma spotted the tell tale signs of his anxiety, as his lower lip trembled in unison with is shaky weak knees.
She moved closer to him and firmly took hold of his hips, patting his bottom playfully as she went in for a big, wet kiss on his cheek.
Derek thought he'd collapse in love-crazed extacy. He was melting like pudding in her arms and wished the hug would never end. He lost sensation in his cheek, where he'd been kissed, as if having a romantic allergic reaction.
Emma, realizing how distraught he must've been after the last few days life-changing events decided to show treat him with love, making him feel safe. And hopefully obedient and submissive in hope for more. It would be the carrot he'd never quite reach, but a carrot nontheless.
"I thought we'd try on your cute little uniform" she softly suggested.
She reached back and undid the crotch buttons on Derek's onesie and pulled it over his head. Emma noticed that Derek had wet himself and would need a change before bed. "We'll try your uniform before we change you".
"Slip off your little shoes" She instructed as she held the Sailor suit romper in front of him, ready for him to step into.
He put his feet through the leg-holes and Emma pulled it up, zipping it in the back.
She smiled and giggled as she adjusted the outfit, delighted at how it looked. "Put your shoes back on, then you can look in the mirror."
Derek felt a little sick as he positioned himself in front of the full-length mirror.
It was a navy blue sailor suit with white stripes across, much like a typical toddler version. The shorts ended far above the knees, covering only a bit more than the outline of his thick diapers, his smooth hairless legs sticking out of the leg-holes, all the way down to his black Mary janes and white ruffled socks, from the the stomach and upwards it would almost look like something an adult could wear, at least on halloween, if it wasn't for the fact that the white sailor's cap that covered half of his back was embroided with the words, "Tea Boy" in bright pink.
He was a bit relieved that the frills on his padded bottom were almost the same color as the shorts, making them harder to detect, atleast at a distance.
"You look like such an obedient and polite little boy". Emma complimented the cringing sissy.
"You can choose what shoes and socks you wear with it, wouldn't it be fun to show off all your pretty shoes and socks at the office?" Emma teased, enjoying Derek's humiliating predicament.
Emma undressed him again, ordering him to brush his teeth and use the bathroom. Just before bed was the only time Derek was allowed to use the bathroom, giving him a chance to avoid going 'number 2' in his diaper. Derek tried his best to squeeze out the last drops from his bladder as well, committed to atleast keeping his diapers dry during the night.
Jake had just come home as Derek had been changed and put back in his onesie and night-time bonnet in the bathroom.
Derek waddled besides Emma, submissivly holding her hand, cringing in the presence of Jake. He hadn't gotten used to being exposed to any onlookers beside Emma, and certainly not Jake.
He received a stern look from both Jake and Emma as he had forgotten to greet him home properly. "W-Welcome home Master Jake" Derek said, blushing heavily as he bowed his head and performed a curtsy to him, still holding Emma's comforting hand.
Jake barely looked at Derek's humiliating routine as he stared at Emma's big busom instead, mentally undressing her. Emma let go of Derek's hand as Jake moved in for a long kiss on her lips as he caressed his big hands all over her body. Emma moaned in pleasure, she had missed him all day as she had stayed home to keep an eye on Derek.
"Alright, let's put the baby to bed" Jake said, sounding hurried. "It's 7:01pm, you should be asleep by now, you have a big day tommorow, Tea boy". Jake asserted.
Emma once again took Derek's hand, leading him to his nursery. "Do I also get a bedtime curtsy?" Emma playfully asked.
Derek submissivly did as he was told, looking forward his early bedtime now that Jake was home, he was too intimidated to enjoy himself in his current state.
Emma helped him climb over the railing as he plopped down in his crib. "See you in the morning, sweet dreams baby boy..." Emma cooed at him, relieved that he was finally in his crib, she couldn't wait to throw herself over Jake. The more time she spent with Derek the more she craved a real man.
--
Derek stood alone in a field next to a tree, surrounding him was a thick, wide row of bright red roses, one meter wide and one meter long. Or was it the other way around? he thought, though he supposed it didn't matter, as he was almost certain that it was the same in the end.
Derek did not know why he was standing in the middle of a field, surrounded by roses, in his finest little dress and shoes.
"But it must almost certainly mean that I'm suppose to stay put, otherwise the roses would not have grown all around me". He reasoned, proud of how bright he was.
That's when he heard a rustling sound from the bush behind the tree, Derek was startled by the noice as he did not know what what awaited behind it. It could be a big scary monster he thought, though he could not remember even once seeing one. "Would it have two legs or four legs?" Derek pondered, as if those was the only available options for a monster".
Suddenly a large rabbit jumped out, looking at Derek, as if it was surprised someone was there.
Derek wouldn't have thought this to be the slightest bit odd if it weren't for the fact that the rabbit wore two pairs of Greggo leather shoes, Derek knew they were very expensive and couldn't understand why a rabbit, which has four feet, would buy such expensive shoes as two pair would be needed.
"Oh my" the Rabbit said. "You are terribly late, you must hurry up!"
Derek was shocked at finding out that he was late. He did not know what he was late for, but felt guilty for standing still in his little square, wasting precious time.
One might have suspected the Rabbit for being a liar. But Derek had not once been lied to by a rabbit.
Derek carelessly tried to step over the roses, only to get entangled in them, falling over and extending his hands in apprehension of hitting the ground.
When little Derek had fallen for a good 10 seconds he began to suspect that something was up. He did not remember growing so tall that a fall would take such a long time, in fact, he knew he was quite small for his age.
He figured there had to be a more reasonable explanation as he opened his eyes to investigate the issue.
"It would appear that I've fallen into a hole, how silly!" He exclaimed as he was descending down, what seemed like an endless tunnel.
He was getting bored of the wait and started looking around, noticing that all of his dresses and bonnets were hanging on the wall.
His crib and diapers were in full view for whoever else would fall down the hole, marked with his name and address, making him blush in shame.
"Oh boy.. I hope no one has time to read on their way down, they would think I'm so silly!" he thought.
Finally he landed with a 'thud'. But he was unharmed and quickly rose to his feet, relieved that the ruffles on his socks were still there, and his ballet-shoes were as polished and shiny as ever.
Before him a boat had just embarked on a journey over the lake, he was too late!
Derek shouted "Please stop! I have to get on the boat!". The boat did not stop, despite being very close-by.
He was disappointed to find out that the captain of the boat was a Walrus. Derek had learned in school that Walrusses did
in fact not have any exterior ears, and would because of that, not hear very well.
Derek thought it was mighty silly to allow a walrus as a captain, as it would be nearly impossible to communicate with it.
"Oh well, no other choice than to swim across." Derek sighed, as he held the hem of his dress and jumped in.
But Derek had never learned how to swim, it had not crossed his mind that there would be a skill barrier for something that seemed so simple. He was flailing with his tired arms as he yet again cried out for the boat to stop.
"Use your diaper!" The rabbit shouted.
The rabbit had made it on the boat in time and had, himself, tried contacting the walrus, equally frustrated with the choice of captain.
"Use my diaper? how?" Derek replied.
"There's only one way to use a diaper, silly!" "You have to wet it so it keeps you afloat!"
Derek was very thankful for the advice as he concentrated on wetting his diaper, pushing slightly and letting the floodgates
open. Soon the diaper had expanded so much that he was floating on top of the surface going the same speed as the boat.
Soon he was ashore, safe and sound and proceded into the lone building on the shore bed, not knowing what to find.
He quickly realized that he was in the office of 'CareApp inc' and spotted Mike and Elliot, his two Programming-engineers.
"Would any of you two care to explain why our office has moved to this very remote location, far under ground?" Derek shouted in anger.
Mike and Elliot turned around and then looked at eachother, as Mike said "Say, Elliot, why is this angry baby yelling at us?"
Elliot responded "Well, Mike, It would seem like this baby think he's in charge, how curious!"
Mike and Elliot laughed merrily, in fact, so loud that the building shook as they each grabbed hold of Derek's hands.
They yelled out "Will someone take care of this baby? We are very busy and important people".
Derek was furious at this point, how dare they defy him? He shook with anger as they held him tight, parading him around in
the office.
"Oh dear oh dear.." A woman said behind them. Turning around, Derek saw the entire office being filled with people.
He recognized most of them, it was his cousins, his old friends and his entire Highschool-class!"
Everyone seemed to spot Derek at the same time as they all chanted, "Look at baby Derek!" as they all started laughing and
yeering. Pointing at him. "The shame!" someone yelled. Derek filled his diapers yet again in humiliation.
Melissa, his old highschool crush walked up to him and said, "Wake up!"
The big onlooking crowd followed suit and all started chanting. "Wake up!, Wake up little sissy!" "WAKE UP!".