Diego's Romantic New Job

In a magical fantasy kingdom there was a town ruled over by a princess. This princess was the most beautiful princess in all the land. She was kind, benevolent and loved by everyone. But she wasn't just totally beautiful and incredibly perfect in every way, she was also ruthless against her enemies. Many an army fell before her strategic might and even if they reached the castle, she could've taken them out with one hand tied behind her back.

Men came from all around to try to become her prince charming and though she briefly entertained their advances, she sent them on their way. No one could be enough to win her love. Maybe some day some brave knight or some dashing prince could sweep her off her feet, but for now, she was just going to take it easy.

She invited her subjects to the castle so they can enjoy her favorite pastime with her. A woman with one of those medieval trumpet things walked out as her guests looked on. Playing a short fanfare she then yelled out, "Presenting her royal majesty. The most awesomest woman on the planet and your one true ruler. The amazing and wonderful, Princess Gracie!"

The crowd went crazy as she stepped out onto the balcony overlooking an arena, in a beautiful purple gown. She wore a dress covered in purple jewelry. She had so much on her that if she stepped into the light, she'd sparkle so brightly that it could render you blind for a short time.

"Welcome to my castle, plebians. It's time for my favorite part of the day and I'm sure it's all of yours too."

The crowd cheered. Many of them wishing that Gracie would even glance in their direction. "Ok, ok. Settle down, everyone. Guards, bring out the fool!"

The doors leading into the arena opened and a guy in a blue and yellow jester outfit was thrown inside. He landed face first in a mud puddle. Already, the crowd was giggling at this fool. He slowly got to his feet, almost slipping on the mud and falling again before eventually standing upright.

His knees were shaking and his heart was pounding as he noticed that crowd was much larger than previous days. He knew that there was only one way he could get a laugh out of Gracie, but he really hated doing it.

"So, Diego, ready to perform your little routine?" she said, with the crowd snickering at the double meaning behind that.

"Your majesty, m-maybe I could do something else for once? I thought that routine would get stale after the 3rd...month."

"Nonsense, fool. You know how much that little scepter of yours makes me laugh. Now drop your pants and wiggle it around for all of us."

With the mostly female crowd already giggling at this red faced jester who was shivering like a leaf at the mere thought of showing off his tiny manhood again, he knew that any attempt to deviate from his routine would mean he'd be forced into a worse punishment. But still, he had to try.

"Please, Princess Gracie, I've been researching new material. I promise you it's hilarious, even more so than my...uh, you know..."

"Your what, fool?"

He sighed and said. "My royally tiny manhood."

Much of the audience laughed at that. She then said, "Fine, but be warned, if I don't get even a chuckle out of this, you know what the punishment is."

She then pointed to a woman in a black hooded robe who was wheeling out a large wooden device. It looked like the gallows, complete with a noose and a trapdoor so the rope is tight around what it was hanging, but Diego knew that he wasn't going to be hung by his neck. No, that would be too merciful for what she had in store for him.

Instead, the rope would be tied around his torso, so his hands were bound to his side, then the trap door would open, sending him downwards where he would be hanging in front of the townsfolk. His clothes would be then ripped off by the hangwoman, until he was completely bare and finally, he'd be left there for a whole day for ANYONE to do ANYTHING with.

Most of the time it was just to laugh at him and humiliate him. Some would pelt him with rotten fruit or vegetables, but the less tactful townsfolk, mostly the women whose husbands or boyfriends have either long since left them or never existed in the first place would toy around with him. He didn't know whether that or the rotten fruit thing was worse.

"I-I...I assure you, I've been researching some new jokes, I hope you like them."

"You'd better hope that as well, fool."

He took out a few flash cards from his pocket with some jokes hastily scribbled on them. He did look up some jokes he had in a book in his house. Unfortunately, they were from a children's joke book that was much older than he was. Due to his meager earnings, he didn't really have many options.

He looked at a few of them and started to read one of them off.

He cleared his throat and began.

"W-what did one wall say to the other wall?"

...

"Meet you at the corner!"

Nary a peep from either Princess Gracie or the crowd.

"Heh....uh...ok then. Umm..."

"Two fish were in a tank. One turns to the other and then asks, "Do you know how to drive this thing?""

...

"Get it? Cause you think it would be a fish tank, but it's...an army...tank."

A few murmurs went through the crowd, but no laughs were had.

"What's a tank?"

"Yeah, we're in medieval times, we don't know what a tank is!"

The townsfolk started to boo.

"Wait! Wait! Ok...umm."

Now panicking, Diego went through several of the flash cards before settling on one.

"A man walks into a bar."

...

"He says, "ow.""

He smiled hoping that somehow that would produce a laugh. That's when he heard some one start giggling. He and the rest of the audience looked around wondering who it was. It was Gracie! She was giggling.

"LOOK! I DID IT! I MADE HER LAUGH!"

Diego was ecstatic, he managed to make her laugh without his nudity. But Gracie then said, "Sorry. I wasn't laughing at your awful joke, I was laughing at the fact that "ow" is probably one of the many things that you're gonna say once you're punished. GUARDS!"

That's when the guards descended upon him. "Wait, you haven't heard the one about the chicken crossing the playground!"

The crowd then screamed in unison. "TO GET TO THE OTHER SLIDE!"

"Have you all heard these before!? WAIT, NO! PLEASE!"

He was grabbed by the shoulders and escorted to the gallows. But just before he was brought up, he screamed out, "OK, PRINCESS, YOU WANT A REAL JOKE? FINE! HERE'S ONE!

WHAT'S FAKE, INCOMPETENT AND NOT FIT TO BE WHERE THEY ARE RIGHT NOW?"

She held up a hand to signal to the guards to stop. "Alright, I'll bite. What?"

"YOU!"

Everyone gasped.

"HOW DARE YOU! YOU'RE NOTHING BUT A LOWLY PEON. A FOOL. A PEASANT. YET YOU BARK AT ME IN THAT TONE? TO HELL WITH THE GALLOWS, YOU JUST EARNED THE GUILLOTINE!"

"You're not the true ruler of this kingdom, you're just a replacement since the queen disappeared. Ever since she did, we've have done nothing but suffer! We are all living in squalor and poverty while you have this lavish castle and opulent jewelry and clothing!"

"GUARDS, EXECUTE HIM! I'VE GROWN TIRED OF THIS FOOL."

"I might be a fool, but at least I'm dressed for the job I have! Meanwhile, you...heh...seemed to have forgotten something."

"WHAT ARE YOU TALKING ABO-"

At that moment, Princess Gracie felt a breeze. She noticed that she felt a lot freer than before. She looked down her gown was nowhere to be seen. Her jewelry, her shoes and her undergarments. ALL GONE. The only thing she had was her crown.

She was standing before all of her subjects, completely naked. She screamed and wrapped her hands around her trying to cover up. All of her subjects, her guards and especially Diego, were laughing at the naked princess.

"Nice outfit, Princess. Must be the latest from the Emperor's new clothes line."

This made the audience laugh uproariously as they pointed and laughed at Gracie's frantic attempts to keep covered.

"NO, STOP! DON'T LOOK AT ME! I AM YOUR RULER! I DEMAND RESPECT! I DEMAND YOUR LOYALTY! I DEMAND-"

"-TO KNOW WHAT'S GOING ON HERE!"

Everyone went quiet as they looked at the figure who walked out behind Gracie.

Everyone gasped in awe and then said in unison, "THE QUEEN!"

It was Queen Grace. Clad in a much fancier Elizabethan style gown and much more modest but shiner crown she looked down at Gracie wearing nothing but a crown, a blush and her hands.

"M-m-mom. You're home early...heh."

"I come home from visiting a neighboring kingdom and I find you strutting around in front of everyone, in your birthday suit like this was a brothel!?"

"NO I SWEAR, THIS ISN'T WHAT IT LOOKS LIKE I-"

"AND WHY IS THE KING DRESSED LIKE THIS?"

Everyone gasped again and turned to Diego. Even he was stunned at this plot twist. "I'm the king?"

"Yes, why are you dressed like a common fool?"

The guards who were holding Diego in place to take him to the guillotine gently took their hands off, brushed off his jester outfit and stepped aside. He then ran to the door that led into the castle.

"Gracie, explain yourself."

Gracie just stood there, shivering from the utter humiliation she was feeling as some of her formally loyal subjects were cat-calling and jeering at her as she tried to stammer out a response.

That's when Diego walked out onto the balcony, dressed in a blue colored royal garb. With a sapphire covered scepter and crown. "May I, my Queen?"

"But of course, my King."

Diego then walked up to Gracie and took her crown leaving her with nothing on her person. With her completely bare, she started to hyperventilate at the sight of Diego staring her up and down. He seemed like he was much taller than before as he looked down on her like he was a giant.

He then chuckled and brought out the jester hat he was wearing before and placed it on her head. "There we go, I think this look suits you much better, fool."

"B-b-but, I'm the princess. I'm supposed to be...royal and loved."

"Maybe once you earn the love of your subjects, you'll be considered royalty once more. But for now...GUARDS! It's time to put the fool in her place."

The guards took Gracie by the arms, holding her up in front of the arena. As she got a good look at everyone pointing and laughing, she thought things couldn't get much worse until they tossed her down into the arena below.

She landed in the same mud puddle Diego was tossed in. With her face in the puddle and her ass up in the air, everyone was losing their minds pointing at laughing at the former princess.

She curled up into a fetal position, with her legs trying to cover her chest as she looked up at the balcony she was once on and saw the King and Queen passionately making out with each other as everyone laughed at her.

Tears started to form as she was subjected to the utter mockery that Diego would normally be subjected to. The King then broke off the kiss that he and Queen were sharing. As Grace fanned herself, clearly turned on from his royal majesty's loving, he spoke out to his new jester.

"Now dance for us, Gracie. Show everyone your funny dance moves."

Gracie forced herself to stand up and uncover herself and she did a little dance. Wearing nothing but a jester hat, a blush and some mud, she danced for all her subjects.

Everyone was laughing at her, including both Diego and her mom, who was taking an uncharacteristic amount of joy in her misery. That's when she heard a shrill beeping sound.

It was her alarm.

As she shot upright in bed, she realized she was back in her room in her pjs. It was now 8 am. She looked at a chair in her room. Draped over it was a new pair of green overalls. On it was a note from Diego that read:

Here's a brand new set of overalls, just for the richest groundskeeper I know.

Oh and now you can actually wear underwear with them.

Now you hopefully won't be showing off your a$$ets if you lose them again. >:3

She sighed and got out of bed and dressed in her groundkeeper uniform. It's been three days since her utter humiliation at the hands of Diego. Being stripped of her overalls and forced to run back to her room bottomless. What was worse is that her mom had sex with the guy she was after!

Gracie always considered herself the sexiest and most amazing woman ever, practically because she was told that most of her life. Many a guy wanted her, but she just toyed with them. Either they were dirt poor (though to Gracie anyone worth less than 10 million dollars would be considered dirt poor) or they were some stuffy rich snob who thought they were better than her.

But this guy, this guy who probably wouldn't even know how many zeros was in a billion, not only got one over on her, but looked good doing it too. Given his less than enthusiastic responses to her trying to get to know him, (which mostly involved asking how much he made per month and what he thought about her and nothing about him) she thought the best way to win him over would be to tease and humiliate him.

When that failed, blackmail. Force him to be hers or else he'd be fired. When that failed, she rolled with the fact that he'd rather show off that tiny dick of his than date her.

This backfired to the point of him falling for her mom instead. Not that she didn't know that he already had a thing for her. Why he did, she had no clue. She had everything her mom did. Style, sex appeal, money, charm, money, access to almost anything anyone could ever want, money, power, money and of course money.

Everything that mattered to her. The one thing she didn't have was her mom's age. She was in her 20s, much like Diego, so she figured all her mom's stuff, minus her age, would make her irresistible to him. Yet there he was, being sucked off by her own mother!

When she didn't get her way, she usually bugged her mom or one of the many servants (didn't matter what their actual job was, they were all her servants) to do something that would either go behind the other's back to get it or do it for her, or failing that would prank one of the servants to blow off some steam.

But with her mom adamant that screwed up here and most of the servants instructed not to do anything for her until her punishment was over, she truly felt humbled. Most of them teased and made light of her situation the first two days of her punishment, but now, a few of them felt bad.

They've never seen her this sad before. While most of them thought it was due to being punished, a few of them in the know realized it was due to her feelings for Diego. None of them really knew what she saw in him, but they were told never to pry too much into the lives of the Grayson family.

This mostly meant Grace's life, but this extended to Gracie as well. As Gracie made her own breakfast and then went to work on the section of land that usually belonged to Diego. she wondered if anything would ever be the same for her again.

Speaking of Diego, how did he take this whole thing? Well, he was having the time of his life. After the run back to her room, Diego took great pride in a few snapshots of Gracie's backside that he happened to capture before she covered herself with her hat.

He knew he probably should delete them, as he really had no use for pictures of Gracie's ass. A less savory person would send it to the tabloids, post it online or even keep it for private use. But honestly, he just kept them just in case she started something again.

It's hard to be an annoying spoiled something or other when you can just tell them, "Hey...I got a picture of your ass!"

Or at least that's what he said to himself to justify himself keeping them and trying hard not to stare at the pics too long. Of course, he still teased Gracie about the punishment and about his and Grace's encounter in her bedroom. In fact yesterday he did something pretty petty. He texted Gracie what looked like an apology at first.

It said:

"Gracie, I just wanted to say how sorry I am that I exposed you. To make up for it, I decided to send you a song that will show you how I truly feel about you and the situation you found me and your mom in the other day."

Enclosed was a link to said song, but when she clicked it, it lead to the classic Ray William Johnson song, Doin Your Mom. He was listening from outside her room as he heard the first few "Doin Your Mom's" from her phone.

He then lost his mind laughing when he heard a faint scream of anger coming from her room and she texted back nothing but a few middle finger emojis.

Since then, he kept humming a few bars of that song whenever he was in ear shot of her if he saw her walking around the mansion. Mrs. Grayson pretty much told her outright to not do anything to Diego again or else she'd increase the amount of time she was punished.

He was untouchable...or so he thought. You see, when the mail came that day something interesting came along with it. Many of the staff had their mail rerouted here (aside from their bills which Mrs. Grayson took care of) and some of them subscribed to a local tabloid called the Small Town Inquisitor. It reported mostly on the happenings of the town and was a weekly roundup of events.

No one really cared about that though, they just read it for the gossip section. Every so often something embarrassing would happen and people would submit various pictures. Most of the time, there would be some naked person streaking back home claiming that some mystery woman stole their clothes or something, but sometimes other non-nudity based things would be there.

As a few of them read all the juicy goings on that happened this week, they saw something that made most of the staff burst out laughing.

"HAHAHAHAHA! HOLY HELL! WHICH ONE OF YOU DID THSI!?"

"IT WASN'T ME, BUT ITS PERFECT."

They were laughing at what appeared to be a picture of Gracie running back into the house wearing only a white shirt. Her hands were in between her legs as she ran back into the mansion.

The caption used for the picture:

Gracie runs through courtyard with her A$$ETS exposed! Quite the cheeky young woman, isn't she?

As most of the staff was laughing at the fact that Gracie's booty was caught on film by some rogue paparazzo that slipped through the cracks of security, it slowly dawned on some of them that there was one person who would be furious about this whole thing. Well, ok two if you counted Gracie herself.

Mrs. Grayson. They had to hide this from her or else there would be hell to pay. They all gathered their copies of the Small Town Inquisitor and either hid or destroyed them. All was fine and dandy until they realized that she herself subscribed to the same tabloid.

"We gotta get that away from her!"

A trio of maids ran to her bedroom. The door was open and whoever brought in the mail today left it on her dresser. They took it and was just about to rip it to shreds when Mrs. Grayson, who was in the room the whole time, cleared her throat.

"Ladies, what are you doing?"

"Uhhh....hi ma'am..."

"We were just..."

"Getting rid of this copy of the Small Town Inquisitor."

The other two looked at her like an idiot.

"Because it's last weeks edition! They sent it by mistake."

She then looked at the other two and whispered, "See, I knew what I was doing..."

"Oh...alright then. Carry on." said Grace going back to something she had by her desk.

The 3 maids walked out, triumphant in their ruse. But as they walked out into the hall to shred that magazine, they realized that what they had really was last weeks edition!

They panicked and wondered if they could find a way to intercept this week's edition before she got her hands on it, only to turn back and see Mrs. Grayson, holding it. She had just found the offending page and was gripping it like she was about to rip it in two.