Derek's shameful downfall

[yoboyobo]

Chapter 1.

Derek stepped out of his Mercedes, his heart beating fast with excitement.

Tonight was the night he thought. After years of dressing up in diapers and sissy-dresses at home, masturbating to captions and stories of his fantasies, he was finally gonna take it to the next level.

He had long had fantasies of being dominated and blackmailed into obediance by a woman, preferably one younger than him.

He had parked two blocks away from her apartment so she wouldn't get his plate number.
His chastity deviced felt a bit uncomfortable when he walked. He had one set of keys to the lock with him, as instructed.
He kept a third key at home, just in case.

He had finally met a girl on a fetish site that seemed to geniunly be into dominating sissies, not just effortlessly doing it for money. She said her name was Emma, 18 years old.

It was perfect Derek thought, he wanted the power dynamics an age difference like that could create, not only being diapered and totally sissified in front of a stranger, but the humiliation of doing it in front of someone younger than him made it more shameful and exciting.

He was feeling guilty though, not because what he was about to do per se; more because he hadn't been completely honest. He hadn't given her his real last name, he had created a fake facebook account and given her the number to his "backup phone", aswell as withholding a third key to his chastity. 

He didn't want to be compromised for real, just the illusion of it.
During the day Derek was the owner and CEO of his own smartphone app business, "CareApp inc". A small operation with three employees. They've created and released two apps in total, both marketed towards municipal and government institutions;

'Daycarefree' - A program that keeps track of all available day-care employees in the town/city that can be called in whenever someone is sick or need to be filled in for whatever reason.

'SmartJournal' is the latest app which basically let's all nurses, nurses assistants and personal assistants write and read journal entries of patients in their care.

Derek had come up with both ideas when he was still living at home and had recieved very generous funding from his wealthy mother to start his business. He had hired two programmers who had brilliantly made it into reality for him, and later after realizing that he's not particularly good at sales, a salesman.

A couple of deals with various districts within Los Angeles made his small operation a very lucrative one.

In fact, it was so good that he literally wasn't needed at all, and would usually just lounge around, mostly to the annoyance of his staff, occationally fulfilling his duties as CEO by signing some papers that needed his signature.

This left him with a lot of spare time. Spare time that was often spent in diapers, expensive custom-made sissy dresses,
often frilly and lacy and to any outsider, obsurd looking.

Derek was getting nervous as he knew he was only minutes away from possibly a lifechaning experience. He wondered if his life
wouldn't be a lot better if he didn't have this fetish, if he was heading to a regular girlfriend instead.
He had always been a total failure with girls, always too shy or embarrassed to ask anyone out during his teens and for some reason always ended up getting friendzoned in his adult life.

On a few occations he had been on real dates but had never summoned up the courage to "make a move" and the dates had all ended up with a nervous hug goodbye, never to hear from them again.
He would never admit it, but he was still a virgin despite his 26-years of age.

"Elmwood Road 26E" This was it. "What if she was just a troll and she just gave me a random address?" he thought, slightly apprehended by the thought. "fuc-k it, I can't back out now!" he encouraged himself, despite feeling anything but encouraged at the moment.

He entered the apartment building and looked at the list of residents, under 4E - Emma Von. "That's her".

Derek pushed the elevator button, carrying his bag, containing very questionable items. Two fresh disposable diapers,
his favourite dress - a short yellow one with white frills and lace, a matching yellow bonnet and a pair of patent black Mary Janes.

His ruffled socks and chastity he was already wearing, both hiding under his expensive Dolce & Gabanna pants and Greggo leather shoes.

An obsurd contrast, only to be enhanced by a resident entering the elevator with him. It was a man, he looked about 30, a bit rugged around the edges, unshaven. Derek catched him glance at his shoes and bag, clearly out of place in this lower middle-class area. Derek felt like a little boy in the taller man's presence and kept looking down at his shoes.

"What floor you goin' to, bro?" the man asked assertively.
Derek almost jumped, not expecting a question from the far more masculine man next to him, and awkwardly stumpled out
"Eh, f-four!"
He felt like an idiot, and a sissy, more aware of his frilly socks and chastity device than ever, not to mention what was in his bag.

The elevator first stopped at floor five, the other man had pressed his floor first, clearly not concerned about any consequenses for skipping a floor. Derek awkardly waited for him to exit before he pressed floor 'four', relieved when the doors closed and was left alone.

Derek felt like a vulnerable lamb after that elevator 'incident' as he approached door 4E. He heard music inside, inhaled deeply and pressed the doorbell. He was surprised by the courage he'd summoned up by ringing the door, and tried to steady himself as he heard someone approach the door. "Look cool you idiot!" he internally yelled at himself. "You're a millionaire, goddamnit!"

The door opened. A young blonde woman looked at him with her big icy blue eyes, her manicured eyebrows frowning a little.
She was pretty, tall, slightly taller than Derek and had generous hips, seemed very fit.

"Yes..?" she asked, sounding annoyed, folding her arms.

"Oh, eh, I'm Derek.." he awkwardly responded, feeling pretty dumb about the whole situation.

"Ok, what do you want, Derek?" she asked, annoyed still.

By now Derek was in panic mode, this was clearly not the one he had spoken with online and his was blank and mouth went dry from nervousness.

"Oh, I'm just fuc-king with you, sissy!" she suddenly laughed out.

"Come in.."

Derek was shocked at the level of dominance and superiority she had displayed in their 10 second interaction with each other so far, but nontheless relieved to be let in.

The first thing he noticed as he walked into the hallway was the smell of smoke, clearly she smoked inside.

Derek felt silly taking his fancy shoes off, revealing his childish white frilly socks. It had been his own initiative.

Emma giggled. "That's cute"

"Do you want anything to drink?" she asked as she was walking to the kitchen, with her back to him.

"W-water would be nice" Derek croaked out, feeling his dry throat.

Derek gratefully accepted a glass of water and started sipping on it immediately.

"Go put your clothes on, Derek" she said, straight to the point.

"Small-talk is bullshit" she assertively stated as a matter of fact.

Derek went into the bathroom with his bag and double diapered himself, put on his dress, bonnet and shoes. He looked in the mirror, and staring back was essentially an overgrown toddler. He looked so innocent and childish, blushing slightly giving his chubby cheeks that childishly pink tone.
He wondered how that man in the elevator would look with all of this on. Even if he had shrunk down to Dereks size, he doubted his arms would fit through the holes. His bearded rugged face certainly wouldn't as childish like Derek's did.
Nor would his legs be smooth and hairless.

Derek nervously opened the door, slightly trembling with a feeling of butterflies in his stomach.

"Don't you look adorable.." Emma cooed at him, sitting in the middle of the couch with a glass of wine and a cigarette.
She motioned him over to her and he awkwardly waddled over, legs pushed apart by his thick diapers, not knowing what to say or do. Despite being very nervous he was getting more and more excited, what a thrill!

The music played semi-loudly. "You look just like a little child!" she said with a mocking tone.

"Lay down over my lap" she demanded as she patted her own thick, womanly thighs.

Derek obeyed quickly, intimidated by her feminine scent mixed in with the smell of smoke and alcohol.

Emma pulled up the hem of his dress and giggled as she lightly spanked his diapered bottom. It didn't need to hurt to cement the power-dynamics between them. Emma was clearly the top as Derek was bent over her knee, diapered and chastised. His legs probably smoother than hers.

His bonnet successfully limited his periferal vision and could only look at the floor as he was being spanked and toyed with. His balls and pen-is slightly aching due to the restriction the chastity device caused.

Derek was overwhelmed with shameful excitement.

"Did you bring the keys to your chastity device as I told you?" Emma asked.

"Y-Yes Emma!" Derek excitedly moaned.

Emma slapped him hard on his exposed thigh.

"It's Mistress Emma for nancy boys like you!"

"Y-yes Mistress Emma!" Derek yelled out.

"Go get them"
Derek was helped up to his feet and blushed a little, seeing Emma's superior smile.

"Hold your hem and mince as you walk like a proper sissy!"

Derek did as he was told, feeling silly as he picked up two keys to his padlock. Knowing he had the third one at home.

He turned around, still holding the hem and walking with small steps as he spotted her holding her phone up.

Derek froze up for a second. He hadn't expected any photos or recordings of this "session" and felt uneasy. "A-Are you filming?"

Emma responded, "Yes sissy, I'm recording your pansy ass."
"And that is one hell of a spanking you've earned for failing to address me properly".

"Now come and hand me the keys to your chastity, like a good little girl!" she teased, letting a giggle slip out.

Derek figured that she was clearly into this herself and decided to trust her for the time being, feeling horny as ever and didn't fully care of all the potential harm this could cause his reputation.

He continued to mince forward, acutely aware of the clacking sounds of his shiny mary janes and the bottom part of his diapers exposed under the short hem.

One curtsey for the camera and then we're done, I promise honey..." she cooed. She seemed to switch back and forth between her assertive side and her sweet feminine one. Derek didn't know what to think and simply obeyed her command, humiliated.

She put down her phone in her pocket and took the keys out of his hands and yanked down his diapers. Derek was taken aback and was shocked!

He was very self conscious about his rather small pen-is and even more so now that it was locked up in his pink chastity.

"Lay down".

Derek thought he'd "arrive" right then and there, thinking he was about to lose his virginity, albeit in the most unusual circ-umstances.

He looked up at the ceiling in near extacy as Emma confidentely removed the padlock as she was stroking his smooth childish thighs. Suddenly he heard another "click" and as he looked up he realized that his padlock had been replaced with one of hers.

"It's grade 5 titanium, apperantly" she stated.

"I don't trust little babies like you to be honest when it comes to your naughty bits!" she teased.

Emma knew she had him wrapped around her finger. He was so horny that he could barely see straight and now she was in full control of his sexuality. She smiled, feeling a little proud of how easy it was to manipulate him.

She helped the surprised sissy stand up yet again and pulled up his diapers and straighed out his dress, playing with the ruffles and lace, genuinly admiring the craftmanship of the dress.

Her phone buzzed and she pulled it up, ignoring the re-chastised sissy in front of her before she said, still looking at her phone,
"Would you be a darling and take care of the dishes? my fuc-kbuddy is texting me".

fuc-kbuddy? Derek felt like he'd been shot! He hadn't really expected to get layed but the realisation that she prefered texting
with her "fuc-kbuddy" instead of giving attention to Derek made him feel really small and insignificant.

Derek had been in the friendzone many times before and had often felt like an emasculated loser but this was a whole new level.
He had exposed his most intimate sexual desires only to be fooled into losing control over his own chastity device and ordered to do her dishes like a housekeeper while she casually texted with someone she clearly felt was way more suitable for sex all while ignoring poor Derek.

He was just finishing up in the kitchen as Emma appeared in the doorway "My friend is coming over tonight and we're planning to fuc-k and smoke some weed".

"I'll see you another day, little baby.." she patronizingly said.

Derek felt so silly thinking this whole experience was something "special" for her as it was for him, only to find out that he'd been discarded  so quickly just because a "real" man decided to text her.

"By the way, sissy. There are some new rules from now on, if you ever want to masturbate again."
"I'll be texting you every now and then, and when I do I expect you to send me a selfie showing you in a diaper within 5 minutes, no exeptions!"

Derek was stunned, why was she set on humiliating him and making his life harder even when he was not there in person?"

"W-What?.. eh.. Mistress Emma" He caught himself almost slipping up.

"You are gonna have to wear diapers 24/7 from now on, hehe... won't that be hilarious?" she mocked.

"Starting now by the way, and I don't care that you're double diapered.."

Derek realized he was gonna have to walk several blocks in public to his car thickly diapered under his pants, which would be quite bulky.

He barely fit his pants over the diapers. Even in his regular clothes he simply looked like a child, obviously diapered under his clothes.

He was somewhat relieved that it had just turned dark outside, but he knew that the streets wouldn't be empty, it being only 9pm. Derek stood in the hallway, facing Emma who were leaning against one of the walls, a second glass of wine in the big wineglass. She looked so mature, so womanly.

He felt a sudden rush of jealousy of her obviously very vibrant sex-life when he himself stood in front of her, no longer in control of his sexuality at all and still a virgin.

"S-So when do I get to see you again, Mistress Emma?" he meekly asked.

"I dunno.." She casually responded, like she could take it or leave it.

"B-But my chastity, Mistress Emma.."

"Yeah, whatever, we'll see.. As I said, I'll text you every now and then to keep you in check" she said, sounding bored.

Derek exited the apartment, very much aware of his obvious bulge. He decided against the elevator, in fear of someone entering with him and went for the stairs instead.

It automatically lit up completely as he nervously walked down, hearing the crinkly noise from his diapers echo in the otherwise empty and silent stairway. He increased his speed, paranoid of someone walking through either of the many doors down to the ground floor. He was lucky and made it down unseen and headed towards the front doors, as he walked, or waddled rather, an apartment door behind him unlocked, sending him into panic.

He quickly scurried out into the dark but somewhat lit up streets as a car immediately drove by. "Oh my god people are gonna see me!"

He headed right, into the direction he had come from, he was glad not to see anyone close by. He saw a group of guys walking the same direction in front of him. He prayed that they wouldn't suddenly stop and "hang about" as teenage groups does every now and then.

He turned another corner and to his dismay there was a bunch of girls sitting on a bench, smoking. Being the only one beside them on the street he was obviously gonna draw attention to himself as he shamefully walked past them, shaking with embarrassment.

"Is that fag wearing diapers? Oh my gosh!" one of the girls said as they all burst into laughter. Derek went beet red and just kept on walking the painfully long way to his car. He encountered a few more people along the way, none of them said anything to him but he saw them looking funny at him for sure.

"I'm gonna have to get a saw of some sort to get this chastity device off" he thought as he shamefully drove home to safety,
ready to abandon this whole thing.

Living in a house with a yard and a drive-in garage felt pretty good for Derek as he pulled in the driveway and once inside he tore his clothes off. He kept his diapers around his ankles, for fear that Emma would text him demanding a picture as he examined the new titanium padlock. He remembered that he had a key to his old one and in naive hope he tried to see if it by some chance was the same key to all of them. It wasn't.

He went to his computer to look up how he would get this thing off, it would have to be the padlock as the steelframe of his chastity device was all basically touching the skin of his very delicate parts, it would be too much of a risk to break the whole thing.

He felt a cold shiver down his spine as he saw the google hits of how to cut titanium. "Jet cutting", "Plasma cutting".

There's no way he realized. He felt a little sick and a little horny at the same time. Knowing the tremendous power Emma had over him now was a thrill.
But at the same time he knew how inpractical and frustrating this was going to be, especially since he now had to obey her commands to be diapered 24/7.

He logged onto his facebook account, glancing at the updates of his old school friends. "Living life to the fullest" as a couple of former friends of his posed for a photo on a luxury boat with loads of hot women in mini skirts.

That's the kind of life most if not all his old friends are living, and so would he have if it hadn't been for the fact that he had such a childish  typical "beta" face that gets you instantly friendzoned or laughed at by women, or the fact that he gets nervous talking to them.

He turned to his kinky secret fetish instead and now he is paying for it with his enforced chastity and basically enforced diapering as well. The contrast could not get any greater as he turned his computer off, just wishing he could get some release!

[yoboyobo]

Chapter 2.

Derek was on a cruise ship. "Marymount Class of 2008". It was his highschool reunion.
"Time for your speech, Derek!"

Speech? he thought, why do I have to speak in front of all of these people? I have nothing prepared!
Nontheless he walked up on stage in front of everyone, thinking of something to say, he was nervous and stumbled over his words, people were laughing. "He's so stupid!"

Suddenly he felt an intense urge to pee, so strong that he automatically widened his legs a little bit and just started pushing, like a small child would.

"Oh my god baby Derek is wetting himself, what a poof!" His old crush, Melissa shouted.

Derek looked down at his feet. "Why am I wearing my Mary Janes?" he thought. Then it dawned on him, he was standing in front of his entire highschool reunion, thickly diapered under his frilly bedtime onsie with a pair of frilly socks
and black Mary Jane shoes. He was filling his diapers as everyone were laughing at him.

In panic he tried to leave but he was stuck on that boat. No where to hide, no rescue in sight. That's when Melissa walked up to him and said "Your mother is waiting by the shore, she is very disappointed in you, we're all disappointed in you".
Derek panicked, "Not mother! she can't know!" he begged.

His head was buzzing and there were strange noises coming from everywhere, he felt stressed out.

Derek opened his eyes. His heart was beating fast, for a moment he forgot where he was. Then he realized, it was just a dream! It buzzed again. "My phone!" he thought as he looked at it - nothing.
He looked confused for a second before realizing it was his secondary phone that buzzed, the one Emma had the number to.

Derek jumped out of bed and walked over to his desk, a text from Emma 1 minute ago : "You know the rules honey.. Selfie or you're toast :)"
"Oh fuc-k!" He'd forgotten about that and felt a little humilated at the prospect of having to snap a very embarrassing picture of himself and send it to her.

That's when he felt the wet heavyness of his diapers, he was still double diapered from yesterday and had flooded his diapers during the night. That had never happened to him before.

He knew he didn't have time to change into a fresh one before his 5 minute deadline would run out and would have to do it in his current state. He snapped a picture of himself, laying in bed, showing off his very wet diapers and sent it to her, embarrassed and still shaken up over his dream.

Last night had been hell for Derek, he was not used to wearing his chastity cage for more than a few hours at most, before his balls felt like they were on fire and being squeezed at the same time.
It had been even worse than usual, due to the increase in sexual excitement after his real live encounter with Emma. He had paniced and tried to get it off anyway possible, only to make it hurt even more.

Finally he had fired up a podcast on his phone and had layed down in his bed, fighting the naughty thoughts that made everything painful. Eventually he fell asleep.

His diapers hit the floor with a wet thud as he started a shower, instantly reminded of his chastised state. It wasn't hurting anymore, at least not at the moment. The very thought of him being in forced chastity made his small member expand to the edges of the restrictive tube, causing a slight discomfort. He decided to shower cold.

Derek thought of staying home for the day, after all, he wasn't really needed at the office, but he decided to go anyway, business as usual he thought.

He was about to put on his pants when he realised he needed to be diapered in case she texted him again. "God damnit!"
he yelled out loud.

Eventually he arrived at his office, wearing relatively loose fitting jeans and a single diaper underneath. It wasn't obviously visible unless you really looked for it he figured, still nervous to be walking into his office in his diapered state.

"Good morning Bro!" 

Derek didn't expect his lone salesman, Jake, to be at the office already.

"Oh, h-hello Jake" Derek responded, startled. He hated when Jake called him "bro" it was always said with an ironic tone but he was never completely sure.

"Yeah, I decided to come in early and sort out some paperwork, I have an early sales-call with a private nursing facility". 
"By the way, I'm leaving early today, I have a dinner date that I just won't miss!" he cheerfully revealed. 

That's the thing with Jake, he never asks for anything, he simply tells you what he is going to do. Derek had thought about talking with him about that and was going to demand a little more respect. He was CEO and payed his salary after all.
Somehow he always found an excuse to push that conversation to another day, and he was certainly not going to argue with him today, chastised and diapered.

Jake was the typical Highschool Jock. Big build, tall and a masculine face. Everything Derek wasn't. It didn't matter that they were the same age, he felt small in his presence. The staff knew it too, since Jake handled pretty much all of the client interaction he was the one getting feedback on the software that needed tuning, and would often directly talk with the two programmers to get it resolved, usually looping Derek in last.

Derek hadn't called him on it the first few times and it felt like it was too late to do it now. He justified it by thinking
"That's what I pay them for".
He knew it wasn't really the case, the programmers did too. Derek felt like a fraud sitting in his office, looking at the plack that said "Derek Slate - CEO".

Today he felt more like a fraud than ever and just wanted to hide, he figured he would leave early as well.

A few hours into the day and with Jake already out of the office, it being friday and all, he decided to tell his two programmers, Mike and Elliot, that they could leave whenever they wanted as long as there wasn't any pressing work that needed to be done. There wasn't.

Derek decided to go to the bathroom before he headed out to his car, he wanted everyone to leave before he did so he wouldn't risk them hearing the slightly crinkly sound his diaper made when he walked.
Pulling down his diaper to pee felt a little stupid but there was no way he was going to wet himself, certainly not after wetting in his sleep, he was a grown adult after all!

He did have to sit down to pee however, since his chastity tube was bent slightly inwards making it very difficult doing it standing up.

While sitting on the toilet Derek was re-living the erotic moment of being spanked over Emma's lap. He cringed at the thought of being filmed and pitied himself at the thought of how much his freedom had been limited by Emma's random diaper checks, through selfies. Derek caught himself feeling jealous over Emma's mysterious "friend" who so easily appeared to steal her attention. 

He couldn't stand having his weenie locked up any longer and was desperate to get out of it. He decided to text her.

"Hello Mistress Emma! Can I see you again?" He stared at his phone, waiting for a reply.

"We'll see Derek.. maybe later.." She replied.

"I already have plans". It must be that damn guy, he thought, frustrated.

Derek felt gutted, and embarrassed. He was embarrassed that an 18-year-old had such little interest in him, even after agreeing to indulge him in his fantasies and after locking his cage with her own lock.
That must have been planned he figured, surely she can't cast me aside after this? he fearfully thought.

"By the way, time for another pic" Emma texted back.

Derek did as he was told, he knew he didn't really have a choice. He smiled awkwardly as he angled the camera downwards from above his head, revealing his entire body, including his diapered bottom.

He went home frustrated, he had rarely went a day without pleasuring himself and now he had gone two and it felt. He started getting more and more naughty thoughts as he always did when his libido was high. That night he dressed up at home, alone.

He was in the living room flouncing around feeling the cool air on his pale hairless legs. He curtsied to himself in the mirror, stopping for a moment to judge himself. It wasn't that he was bad looking, or overly feminine either. It was the distinct lack of masculine features that made him look the part.
No apperant jaw line, puffy cheeks and big worrying eyes made out his 'baby-face'. His legs and arms lacked the musclemass that usually came with manhood, either naturally or self-made.

Gym's were anxiety-filled places for Derek and had thus never set foot in one, and it showed as he observed his rather thin, yet slightly chubby legs sticking out of the holes of his diapers. His thin and hairless arms, or 'nerd arms' as he had always defensivly joked, fit in proportion with the rest of his childishly emasculated body as his shoulders disappeared under the
puffy sleeves of his frilly pink dress.

With his regular 'grown-up' clothes he looked like the typical young nerdy guy with an unfortunate lack of testosterone, he realized that he almost looked more natural dressed like a big baby.
As the masochist he is, that is equally erotic as it is humiliating. Standing there, dressed as the over the top sissy his fantasies had allowed him to be, it somehow felt right.

He got to momentarily forget about his anxieties and just pretend to be something else. "Yes mistress Emma, right away!" he said out loud, still looking in the mirror as he curtsied deeply.
It wasn't the same as when he had done it with Emma, as brief and awkward it had been, the thrill of it had been the most intense of his life.

He knew Emma had him wrapped around her finger, not just because of the very unfortunate chastity incident. He couldn't stop thinking about her, all he wanted in that moment was to serve his goddess.

The goddess heeded his call it would seem. "Hey sissy! u busy tonight or what?"

What a silly question he thought as his heart pounded with excitement. With a social life that revolves around being talked down to by his eccentric domineering mother and the occational family gathering where he had become quite a connoisseur of dodging embarrassing relationship questions from his cousins, where instead of admitting his failure as a man would give the impression
that he is single out of choice, and that not being 'tied down' to anyone particular had its 'advantages'.

He always felt silly lying like this, but what else could he do? Tell his family that he is an unkissed virgin at 26?

"No, not at all Mistress Emma! Want me to come over? :)" He decided for and against the silly smileyface and figured since she had used a smiley in a previous text he should too. Probably over-thinking the whole thing.

"I'm coming over to you, give me your address, biaaatch.. :P" Emma couldn't bring herself to ask a sissy for permission.

Derek felt uncertain. Before he had even tried so seek out someone willing to indulge in his fantasies he had set up a number of rules for himself. One of those rules was to not reveal his real identity, or bring someone home which would pretty much be the same thing.

"Can't we meet at your place again? Mine is a total mess atm.." Derek lied, hoping she'd give in.

"It's your place or nothing, silly little baby.. unless you want to be locked up forever.." Emma responded quickly.

"fuc-k" he thought. Was he really going to give up his rules? his identity? Derek knew it would be really stupid. At this point he could pretty much end it by going to the hospital and explain his embarrassing chastity 'situation'. A few pictures and a video with no identity to tie it to would be unlikely to ever find its way to someone who knew him.

This is unfortunately not how Derek thinks when he is sexually inebriated. When he otherwise fears the unexpected and unknown it is another thing when he is horny.

"Can I really hand goddess Emma this power over me? Do I trust this girl?" he thought, already knowing the conclusion of his thought process. Derek felt a thrill surge through his body, his pen-is pressed hard on the unyielding metal tube surrounding it.

"Ambassador Avenue 22, Beverly Hills, last house in the street.." He replied, feeling the butterflies wrestling each other in his tummy.

"Ooh.. Fancy boy <3" Emma replied. Derek's fears were replaced by a sense of pride, maybe he was a bit interesting after all?

Derek ran upstairs into his home made nursery. It wasn't really a nursery, more of a 'secret room' where he hid all of his fetish stuff. The door to this room was always locked whenever someone was visiting, usually his mother or a contractor working on something in the house.

Inside to the right he had a coat-rack where most of his dresses and onesies were hanging, underneath were his shoes, ranging from the standard black Mary Jane to bright pink serving shoes with heel.
To the left stood his inflatable plastic crib, the perfect solution he thought, as it would be really easy to deflate and hide it if needed. In front of it was his bureau containing all of the smaller stuff like socks, bonnets, pacifiers, cloth diapers, diaper covers etc. His closets were well stocked with disposable diapers.

Scattered across the floor was a collection of various toys, dolls and teddybears. He decided to pick it all up and put it the pram which he kept all of his toys in. It certainly looked like a nursery.
He wondered if he was going to keep the door locked and not reveal just how much effort and money he'd spent on his fetish, he was in fact a bit embarrassed at the thought.

The door was kept unlocked, still.

Derek heard a motorcycle outside, that couldn't be Emma, could it? Really? A motorcycle?

He carefully peaked out the nursery window which overlooked his driveway. The street lamp luminated the driveway so that he could see, even after dark. There she was, she was wearing a black motorcycle helmet but it was definately Emma.
She was looking at the trashbins, hoping to spot the address-label just to make sure she was at the right house.
She wore leather pants that tightly hugged her generous legs and ass, an equally stylish leather jacket.

Derek looked in awe as she confidently walked towards the entrance and took off her helmet and let her blonde shoulder length hair hang free. Her lips were bright red, a color few people really pull off, but she certainly did.

The bell rang. Derek was somehow taken by surprise. He hurried downstairs and was just about to fling the door open, stopping momentarily realizing he ridiculus outfit he was wearing.
He tried to think of something cool or funny to say, she had after all played him a prank at the door over at her place.

He unfortunately drew a blank, as he had always done in the presence of girls and just timidly opened the door for her instead, awkwardly stumbling out a greeting in almost a whisper.
"Eh.. H-Hello Em- I mean, Mistress Emma". Derek felt like a loser.

"Am I being greeted by a little housemouse?" Emma was clearly not impressed by his useless attempt at welcoming her at the door.

"I'm s-sorry! P-Please come in Mistress Emma!" Derek nervously said, redfaced and shaken, loud enough thankfully.

Emma wasted no time as she strode in, pushing Derek gently to the side, holding him there as she towered over him in her stiletto boots. Derek broke eye contact almost immedately and looked down at their feet instead. The power dynamic was embarrassing for Derek, and equally exhilarating for both.

He felt weak, like a baby in her presence, or more like someone standing before a judge, awaiting sentencing in a murder trial. What would his fate be?

[yoboyobo]

Chapter 3.

Emma laughed, breaking the electric silence and handed him her leather jacket, revealing a white tank top underneath and started looking around the house. Derek was confused for a second.
"Why did she give me her Jacket?" he thought as he pondered her strange gift just to realize what a fool he was.
He had been trusted to hang it on the coat hanger.   "Jesus, I'm an idiot" he thought.
Emma did the signature whistle of someone who's impressed.

"Nice place, how did you pay for it?" She went straight for the point.
Derek wasn't sure how to answer it, or if he wanted to rather.

"Daddy?" Emma said as she looked at him, seeing no visible reaction. "Mommy then?" Derek shifted uncomfortably.
Emma didn't wait for a response. "She must really love her widdle baby to buy you something like this". She teasingly cooed.

"Ah, eh, well.. I mean she only gave me it as a loan, I'm paying it off myself.."
Derek felt like he was defending himself.

Seeing how unfomfortable Derek looked, Emma changed the subject. "You look adorable, almost like a proper little girl!"
Derek felt a thrill, he did like the attention.

"Are you not going to curtsy to your superior?" she playfully asked without really asking.

"Of course Mistress Emma.." Derek responded as he curtsied, feeling a bit silly and blushed slightly.
Emma was just smiling, silently observing the childish sissy in front of her. Derek desperately tried to find something witty or relevant to say, yet again drawing a blank.

Suddenly Emma turned a little to the side, slowly moving her hand over her butt. "Do you like my ass, little boy?" she asked. "I've seen you sneaking naughty little glances".

Derek's eyes opened wide in surprise of the bold advances she made. "You wanna touch?"

Derek felt a spurt of pee entering his diaper in excitement, no one had ever made overt sexual advances towards him in his life and he literally didn't know what to do.
Finally he nodded 'yes' and Emma motioned him to come closer with her finger.

"A little butt-boy like you should get a treat". Emma giggled. It was clear she was dealing with a hopeless virgin.

Derek gave out a silly moan as he meekly caressed the warm slippery leather. Emma laughed again and took his hand and pressed it down harder on her ass. Derek almost came in his diaper, despite his chastity.

"Poor little virginboy.." she teased. "A real man would've fuc-ked me by now, wouldn't he?"

Derek froze in embarrassement. He knew she was right, he realized it was quite obvious that he had never dealt with girls before.  "Yes Mistress Emma" he submissivly agreed.

"You can call me Ma'am from now on, butt-boy" "Mistress kinda implies sex, doesn't it?"

It was a humiliating moment for Derek, he felt completely de-sexualised by the teenager in front of him. Derek wondered if she had wanted sex to begin with, and then somehow realizing that he is simply too much of a sissy to get the job done. Or was this just the way she had intended on teasing him? He really didn't know.

"Yes Ma'am". Somehow it felt more stupid saying that, 'Mistress' at least sounded cool. Spending time with a 'mistress' was something seen as kinky and cool.

Now he had been reduced to calling her "Ma'am", something an obedient child would have to do in the presence of an adult.

Emma walked into his kitchen in search of wine with a superior smirk, she was gleaming with happiness, for several reasons.
She and her fuc-kbuddy were now a couple. She had landed a great man, with a dong of a horse. She had of course felt obligated to tell him about Derek, and their 'little game' that had just begun.

He had looked shocked when she showed him the video of Derek, prancing around thickly diapered wearing a silly little dress. Emma told him that she had a thing for dominating and humiliating weak men.
"T-That's my boss" He said in disbelief.
"What did you say, Jake?" Emma had responded, her too in disbelief.

"That's Derek Slate, he owns the company I work for."
"He's THE loser boss I told you about". Jake started laughing.

"Small fuc-king world.." Emma slyly said before herself erupting in laughter.

"You know, he texted me earlier asking to see me". Emma revealed, geniunly curious of how Jake wanted to play this out. She hadn't known Jake for long, but long enough to know that he would take advantage of this situation, one way or another.

"You should go to his place, get as much dirt on him as possible on camera, I'll stay here in the mean time, I have a plan." Emma was excited. She felt a bit sorry for Derek but hey, her loyality had always been to herself, foremost. Now that Jake had seen an opportunity to make a rapid career she knew she was in for one hell of a ride. Not just in bed.

Emma had had a terrible childhood. Her parents were drug addicts and unfit to take care of her. She took to the streets when she was thirteen, earning a living by stealing, lying and selling drugs.
She had spent 6-months in juvi after getting caught hotwiring a car, by crashing into a policecar.

She figured it was her childhood that caused her sadistic and dominant tendencies that gave her pleasure in humiliating and manipulating people, especially spoiled, priviledged pansies like Derek.

Emma sipped on the wine she'd found, 'Château Léoville Las Cases' "Sounds fancy" She said out to no one in particular, smutting on it to see if she'd notice a difference from her usual $9 wine.

"Oh, yes it was a gift from mother, I believe it's a $150 bottle, Ma'am". Derek responded, slightly annoyed that such a nice and expensive bottle of wine had been opened without permission.

"Hmpfh", she scoffed. "Can't taste a difference anyway".
"How about we play a little game, Lacypoof". Emma liked being creative with the names she called him, never settling for one in particular.

"A game?" Derek wondered.

"I totally forgot about your spanking.. you were supposed to get another one over at my apartment, can't remember the reason though".
"So how about I give you the spanking you deserve, and for each spank you will tell me a secret about yourself".

By now Derek was so excited he was about to melt. He had longed for her strong feminine legs, her firm hand, her smell. To be truly dominated and punished. At this very moment Derek figured everything would be alright, this is what he had always wanted. He had been right to see her at his house.

He layed down over her lap. She smelled of leather, smoke and a sweet perfume. He felt like such a baby in her presence as all he smelled of was a hint of pee and baby powder.

He hadn't expected his diapers to be yanked down, she had only spanked him playfully the last time. She meant business this time.

Emma couldn't help but laugh a little bit as she saw Derek's tiny caged pen-is, looking even smaller than it was since he was smooth shaven down there, it honestly wouldn't look too much out of place in a daycare center.
She saw Derek squirm a little as she was laughing. "Naaw, is widdle baby embarrassed?" she cooed in clear mockery.
Derek took it for the rhetorical question it was and remained silent.

Emma continued "You know, my boyfriend has like a 7 or 8 inch coc-k.. that's why he gets to fuc-k me".

"You look like a real baby in comparison!" "I think it's good that it is locked up and hidden underneath thick layers of thirsty diapers, don't you?"

Derek was blushing hard at the intense humiliation, yet his pen-is betraying him by trying to expand outside its confines, causing additional discomfort. "Y-Yes Ma'am".

*SMACK* Derek was shocked at how much it hurt, throwing him into a panic. "There's no way I can withstand this!" he thought, just before getting smacked again, even harder, making him squeal in pain.

"LAY STILL!" "Stop squirming around or you'll be over my lap all day" Emma sounded furious, genuinly scaring the helpless sissy in her lap.

"This still counts as one slap, now, tell me an embarrassing secret about yourself, or else!"

Derek's mind was spinning as he desperately thought of what to say. "I-I don't like coffee" he blurted out.

*SMACK* Derek flinched and sobbed in shock over the pain.

"You don't like coffee? who gives a shit?!" "This still counts as one and we have 19 more to go, or an infinite if you continue like this".

"Try again." This time she sounded cool and collected, like she really wanted the information.

"I-I have a nursery upstairs!" Derek revealed in panic, desperately hoping it would be enough to please her.

"Nursery? like with toys and a crib and all that?"

"Y-yes Ma'am!"

"Interesting". *SMACK*

"Ooow" Derek moaned pathetically as tears welled up in his eyes. He wasn't used to any form of physical pain and this experience had turned out to be a very unpleasant one.

"That's 2, new secret - GO" she robotically demanded while thinking that he wasn't going to last 18 more smackings, he was clearly more of a delicate sissy than she had earlier figured.

Derek was still in panic mode, he knew he had to say something that really embarrassed him, he didn't care what at this point.

"I-I'm a virgin!"

"Hardly a secret, eh?" Emma teased.

"N-no no! I mean, I wet myself for real in my sleep last night".

Emma laughed at the desperate revelation, she would've settled for the virgin 'reveal' but appreciated his effort.

"Fitting for a baby like you, is it not?"

"Y-Yes Ma'am it is very fitting for a baby like me". Derek pandered to her sadistic side and he knew it, it was clear she wanted him in a state of pain and humiliation.

Emma pondered if she shouldn't change strategies, her plan had been to get him to reveal something really juicy as she, albeit, sloppily filmed him getting a spanking over her lap.
His tolerance for pain was laughable and she was concerned that he might just shut off completely.

Derek flinched and squealed in anticipation for the next blow as he felt Emmas body shift, tears rolling down his cheeks.

"There there.." Emma soothed as she gently stroked her hand over his bottom. "You want me to stop, don't you?" She asked patronizingly.

Derek wasn't sure if it was a lie or a genuine question but he did his best to gain her sympathy, desperate to escape the unbearable pain. "Pretty pretty please Ma'am! I'll do anything!"

He was relieved when he was helped to his feet, he saw her put her phone to her side as she pulled up his diaper. Emma saw the question on his face. "Yes honeybunny, I'm filming you..."

"So that I can watch this over and over again and re-live every moment". Derek bought the explanation, even feeling honored, still a bit nervous at the prospect of so much damaging material of him being on record.

"Kiss my boots" Emma ordered, still filming. She wanted him kneeling on the floor at her feet, she needed to keep the power dynamic going.

"Instead of spanking you, which you clearly can't handle, you are going to truthfully answer my questions."
"If I even suspect that you are lying or withholding information you are going over my lap for the remaining 18 spanks."

Derek cowered at her feet, gently kissing her boots in submission, he'd pretty much do anything to avoid the continuation of the spanking. "Why do you like to dress like a little baby girl?" Something obvious, simple to begin with Emma figured.

"I-I dunno... I just do I guess.. I mean, how could I know?" Derek knew that answer would not be accepted, but at the same time he wasn't really good at describing his feelings in detail, certainly not in his current state. Emma looked annoyed as she realized she was gonna have to lead the conversation.

"Do you think it's because you don't really feel like a man?" she asked.

"I guess so, Ma'am"

"Do you think it's because you secretly want to lose control? to BE controlled?" Emma knew all too well how people like Derek worked, she had met countless of people like him online, many of them telling
her their intimate secrets and desires to her, none of them except Derek had been brave enough to find a way to make it a reality. She also knew that it ironically made Derek the weakest of them all.

"Y-Yes Emma, I mean, Ma'am, that is also true".

"Tell me, little boy, tell me your darkest most wicked desires".

Derek steadied himself, it felt safe sitting at her feet, Emma was such a goddess in his eyes that he simply couldn't refuse her.

"I want to be treated like a baby.. or something like it.. I want you to keep me locked in chastity, control my sexuality, unforgiving, merciless.." He blushed as he continued, more and more aware of the camera lense staring him in the face.

"I want to be laughed at, humiliated, exposed.. for who I am".  He regretted saying that last part, it was too much, too dark, he knew it was true only in fantasy, not reality.

"I-I don't know what else!" Derek felt his eyes tearing up again, not out of sadness, he just felt so exposed, vulnerable. He had never felt anything like it.

"Where do you work?" Emma enquired, already knowing the answer.

"I-I don't really work.." Derek lied. He didn't really know why he lied, maybe it was those rules he had set up for himself before all of this started who popped into his head.

"Alright, over my lap you go.." Emma stated, looking pissed.

"No- wait!, I'll tell you!" he fearfully cried. Derek felt a surge of shame traveling through his body as he realized how terrified he was of getting spanked by a teenage girl.

"I own a company called 'CareApp', I'm also the CEO" Emma knew he was telling the thruth, that's the trick with 'interrogations', to already know the answer of the questions you're asking.

"Is there anyone in the staff that scares you? Make you feel like a child?" Emma knew it was a strange question, she just couldn't help herself.

Derek paused for a second at the odd question, but dared not defy her a second time. "Y-yes.. my salesman is kind of a bully and doesn't respect me..".

Emma couldn't help but laughing, knowing the 'bully' was her boyfriend, unbeknownst to Derek.

"Does he make you feel like a little sissy?" She giggled.

"Y-yes.. He makes me feel small and silly compared to him".

"What do you think he would say if he knew about your little secrets?" Emma knew she was going over the line, asking so many question about this 'salesman', but she wanted to build suspense for their future encounter.
"I think he would laugh at me, and make me cry!" Derek revealed, feeling uneasy about the rather specific questions, hoping it was just an attempt to play with his feelings.

"Alright.. hm.. Do you own the entire company yourself?"

"Eh, well, kinda.. it's complicated." Derek answered, not really wanting to get into the details of how it worked.

"Do I look dumb enough not to understand just because it's complicated?" Emma asked, giving a warning nod towards her lap.

Derek explained how his mother had funded the business by giving him a loan, in turn she had the right to seize all of his shares should she deem him unable to re-pay the loan.
"The same as was done with this house". He added.

"Smart mom you've got, Sprinklebum" Emma laughed at that one.

"Does she not trust you?" Emma asked, hoping it wouldn't be too personal, somehow.

"She's really tight with money, despite having loads of it, she doesn't trust anyone, I think."

Emma stopped the recording, the filesize was getting big as it was. She was greatful for Derek's excellent wi-fi as she was sending the file to Jake.

"Let's see your nursery!" Emma cheered.

[yoboyobo]

Chapter 4.

Jake looked at the video of Derek's confession. "Holy shit what a prat". "No wonder the company is stuck in a stand-still".
He was annoyed at the fact that Derek's mother technically owned the company, he had researched her when he joined the company.

Her name is Helen Slate. Founder of Slate Funds, a medium sized mutual-funds company that was absorbed by Vanguard a few years back. He figured she was worth at least a billion at this point, he also knew that she's a stone cold bitch, basically a high functioning sociopath. "Isn't that how they all of the financial elites are?" the thought.

There was no way to blackmail her, she would be happy to throw her own son under the bus just to not let some asshole win. He figured 'CareApp' was probably irrelevant to her, she probably didn't pay any attention to it. Maybe he could convince her that the only way she's getting her money back is if he takes charge instead of Derek.
He knew he had more than enough embarrassing dirt on him, maybe that could be enough to send Helen herself into a sadistic fit, intent on humiliating and punishing her son herself.

He could present himself as the tool to make that happen. Sweep the rug under Derek, humiliate him, crush him. Put him in his place.

He looked at his watch. 9:35PM "fuc-k it, It'll happen tonight" he said to himself and he grabbed his coat. He was going to Helens house.
---
Helen was in a bad mood. 

"I told you to go get the Pappy Van Winkle bottle.. USELESS!" Loretta, her housekeeper apologized profusely even though she knew Helen hadn't mentioned any particular brand of whiskey when she asked for a glass. Helen's outbursts was nothing out of the ordinary, as was often the case when she was feeling moody and started drinking on top of it.

"You know what, LORETTA.. silly name..I'm just gonna go get the bottle myself, you are RELIEEEVED for the day" Helen liked to emphasize certain words to diminish her enemies. This time it wasn't an enemy but it just as well could've been.

Loretta had learned to deal with it and knew she would get an apology and probably a cash bonus the next day, from a more sober and regretfull boss. Loretta was Helen's housekeeper/assistant.
She quite liked Helen, and Helen liked her and they both knew it. Which is why neither of them would lose any sleep over silly incidents like this when she had mixed wine with whiskey.

Helen was just about to pour herself some whiskey from her 23-year-old $2000 bottle when she decided against it. She felt guilty wasting such a fine bottle of whiskey alone, drunk and pissed off.
Instead, she sat down on her victorian fainting couch, half laying and pulled out a cigarr. She always enjoyed a cigarr.
Power. That's why she like them. They exude power. And status, she had never seen a poor person smoke a cigarr.

Suddenly she heard a buzz. It was from her gate. "Who on earth could it be at his hour?" The only regular visitor at this time had been her tax-lawyer, cheating on his wife with her. He was good in bed so she didn't mind, but she knew it wasn't him. He was going to 'try working' on his marriage. Sillyness Helen had thought, but it had not been up to her.

"Who is it?" she enquired through the buzzer, trying not to sound too drunk.

"Hi! My name is Jake Summer, I work for your son."

"You can pull up to the door".

She figured Derek hadn't been killed or been seriously injured, in such an event she would expect the police to contact her. Is he gay and this "Jake" is his boyfriend? could be. Then again, probably not.
Maybe a hitman, 'wouldn't that be clever' she thought, but then again she has no enemies, not that she's aware of anyhow.

"Handsome at least" she muttered quitly to herself as Jake approached the door, where she waited.

"I'm Jake" he said, extending his hand confidentely. Helen shook it, impressed with the grip, not a dead fish, like some, not hard enough to feel like over-compensation either. Controlled.

Jake was a bit taken aback, she was an astonishing looking woman, classy. He figured she must be nearing her 50's but she certainly didn't look it.

"I'm here to blackmail you". Jake appeared confident but he felt enormous pressure, too bold he thought, "I'm toast".

"Well that's a way to get me sober I guess.. didn't expect that." Helen said as she calmly turned around, walking into the house, leaving the door wide open for him. An invitation.

"Whiskey?" she offered. As good of a time as ever to enjoy that $2000 bottle she figured. She started pouring before he had time to answer, clearly not taking no for an answer.

"So.. how fuc-ked am I?" She was smiling as she said it, laughing even. Jake felt awkard, like he was in a lion's nest, being toyed with.

"Well, not you, per se.." The 'I'm blackmailing you' card was only meant to get him inside, it had worked, time to dial back.

"So my son then?" Helen quickly and accurately deduced, already angry at Derek, not yet knowing what for.

Jake had a whole speech planned out only to abandon it. He hadn't expected her reactions at all, she seemed more.. cold, like she only mildly cared, he wondered what would give him the advantage.
The contrast between Derek and Helen was insane. Was this woman really his mother?.

"Sort of, yeah.."

"Hear me out before you jump to conclusions." Jake appealed.

"Get to it, fast" Helen said as she sipped on the lean, smokey whiskey. She was annoyed and impatient. She hate people who wastes time.

"There's something you should see." He pulled up his phone, on it he had two videos of Derek prancing around like a toddler, dragging the family name in the mud.
Jake felt guilty as he started the first one and handed Helen the phone. He didn't want to see her cry.

Helen looked on with interest, at first not quite making out who, or what she was looking at, since Derek had his back turned to the camera, only to sigh deeply when she finally recognized her son.
Jake took a large sip of whiskey, preparing for tears, and figuring out what to say next.

The tears never came, and her sigh turned into laughter. "What has this fuc-king poof gotten himself into?" She started the next video, expecting more of the same.

She watched Derek's shameful breakdown as he was being spanked, his tearful confession of his most intimate secrets, only to pause for a moment. "Drink more whiskey, you made me open the nice bottle, you better drink, cheers!"

Jake was frozen in his seat, complying with her command. "Holy shit what have I gotten myself into?" he thought, losing confidance in his grand plan.

He had wanted to be a tool, a catalyst to direct Helen's shame and anger towards Derek, all while getting what he wanted in return. There seemed to be no shame and no anger.

"Okey, my son is a loser who prefers to wear diapers and little dresses in the presence of women instead of fuc-king them.

"That explains a lot actually, thank you Jake". Jake hadn't expected to get a 'thank you', that's for sure.

"So.. to your point, what exactly is it that you want?" "Money?"

Jake felt he didn't have the psychological advantage, but hoped if he revealed his hand she would realize she was stuck with the losing one. "I want CareApp Inc".

"And why would I ever give it to you?" Helen asked, annoyed and disappointed. She had expected something bigger, more severe.

"I feel that it is mine, I'm the one who got us all the clients, I handle pretty much everything Derek should."
"Besides.. the staff already sees me as the boss, not Derek." Jake said in the most convincing way possible.

"Are you done pitching your silly little case?" Helen asked.

"If you want to own 'CareApp', you're gonna have to impress me more than that." Helen said as she unbuttoned her shirt.

Jake couldn't believe it, she had seemed completely uninterested by his attempts to extort her and her son, and now she wants sex? Jake thought he was dreaming.

"If you want the company, then show me what a man you are!" Helen dared him.

"Show me why I should betray my son for you!"

At this point Helen had nearly unbuttoned the entire row of her shirt.
Jake was wild with lust, this was the most insane and sexy woman he had ever met. "I'm gonna fuc-k Derek's mom!" he thought to himself and he chugged down the remaining whiskey in his glass and pushed Helen down, he was gonna take her right then and there on the kitchen table.

"Take me hard!" Helen yelled, scratching his back.

Jake's all 8 inches were pulsating and rock hard as he pounded her on the table, feeling Helen's giant busom pressing against his ripped stomach. He couldn't help but let out primal grunts as he thrusted into her, his strong jawline tensing up as he growled with lust.

Jake was great in bed and he was not going to disappoint Helen now that he felt there was a chance after all, as he carried her, asking her where the bedroom was.

They both came in wild orgasms, only to recover and start over again, for hours on end.
--
Meanwhile Derek was laying in his inflatable crib, he had spent all evening showing Emma all of his toys and dresses. Finally begging her for a diaper change, blushing as he had asked.

He couldn't believe his luck when he was laying in his crib, exposed in his wet diapers, being teased by Emma as she changed him into fresh ones. He begged her to unlock his chastity. She just laughed.
"Little babies like you don't get to do nasty grown-up stuff, like I do". He nearly exploded in aching frustration.

Emma was a bit worried since she hadn't heard how things had gone for Jake and decided to call it a day. "I'm heading home, sweetie, I'll see you another day!" she cooed as she kissed him on the cheek.
Derek felt content and horny as he layed in his crib. His little weiner felt almost impossibly small in his thick diapers.
If only his chastity cage would magically fall off in his sleep he prayed, as he drifted off to wonderland.

--

Jake and Helen were exhausted. "I underestimated you, Jake." "You certainly know your stuff". Helen declared as a matter of fact. She was pleased and satisfied.
"So.. about what we discussed.." Jake prodded, hoping to hear good news.

"Fine, it's yours". "Who was the girl holding the camera?" Helen asked, changing the subject.

"Eh, just a friend."

"Your girlfriend?" Helen was teasing him, she didn't care.

"I don't care who she is, don't think this thing between you and me was more than just sex".

"Fine, she's my girlfriend." Jake admitted, feeling guilty over cheating on her, not knowing if Helen or Emma would approve of such behaviour.

"She's the one who, 'discovered Derek'?" Helen suspected as much, and had been impressed by the level of sadism and manipulation pulled off by this girl.

"Yeah, Derek apperantly found her on a forum, she has a thing for dominating, whatever Derek is..".  "Her name is Emma".
Helen knew Emma would do great in business, especially sales - given her 'talents'.

"I'll take control of the company, and sell it to you, for a generous sum of $1, but Emma gets 30% equity, I like her."

"Done". Jake couldn't believe it, sure he'd have to train Emma in the art of selling, not just to pervs, but he, much like Helen saw great potential in his slightly psychothic girlfriend.

Helen wasn't done with demands, she was willing to do the same with Derek's rather luxurious house, she'd give it to them. Helen only had one request.

"I want him to suffer". Here we go, thought Jake, 'the psycho is finally showing herself'. Still, he listened.

"I don't want my son to move in with me". Helen dreaded the thought of having to deal with her whimpering sissy of a son on a daily basis. "I'm certainly not going to give him anymore money when I can't even trust that he'll keep his diapers dry".

Jake laughed, it was a reasonable concern.

"I'll do all of this under the condition that he gets to stay in the house, as a tenant or something, I don't really care".

"Most of all I want him to be humiliated, everyday for the rest of his life". "I don't take kindly on pansies like him throwing away not only his own money and life, but my money aswell". Helen's eyes were tense and angry by now.

"I want him to have to look you in the eyes, Emma in the eyes, his staff in the eyes, feeling nothing but shame, helplessness."

"My son is a masochist, a stupid one at that, if you make all of his perverted fantasies into reality he will soon find that he got way more than he bargained for".

Jake looked at Helen, admiring her beauty, her strength, counting his blessings that she had no problem completely destroying her own son's dignity. Almost as if she kinda likes the idea. "That won't be a problem, Helen". Jake promised.

[yoboyobo]

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!".