In a magical fantasy kingdom, a town was ruled over by a princess. This princess was the most beautiful in all the land. She was kind, benevolent, and loved by everyone. But she wasn’t just 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 someday, some brave knight or dashing prince could sweep her off her feet, but she would take it easy for now.

She invited her subjects to the castle to 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 yelled, “Presenting her royal majesty. The most awesome woman on the planet and your one true ruler. The amazing Princess Gracie!”

The crowd went crazy as she stepped 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 wished 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 the crowd was much larger than on 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.

She then lowered it giving the maids a glimpse of Grace at her most furious looking. She then turned the magazine to show them the picture of Gracie’s butt and asked them in a low growl, “Who is responsible for this?”

It was noon, Diego was still off from work so he slept in. As he did, he was dreaming about something very sweet.

“Oh…..Oh yes….Yes please…..Grace….Oh Grace….Yes…..Yes…..Yes I’d love some more ice cream……”

He then snored as he rolled over to his side. “……where do you want me to lick it off this time….”

That’s when his phone rang, arousing him from his arousing dream. “WHA…HUH…WH-!?”

He groggily checked who it was and it was Mrs. Grayson. This perked him right up. “Hello~!” he said, mustering up the sexiest voice he could do.

“Diego, please see me in my office. Immediately. I need to have a word with you.”

“I’ll be there as soon as possible Mrs. Grayson.”

He had a massive smile on his face as the possibilities went wild in his head. It hasn’t even been a month and it was like he was royalty. While he wasn’t being paid for his time off, he got to live in a big fancy mansion and got to spend time with the most beautiful woman he’s ever seen.

She even had the hots for him! It was like a dream come true. Nothing could go wrong!

He got dressed, put on some cologne and walked to her office. Mrs. Grayson was usually busy with her many business ventures. She owned real estate, insurance companies, several pharmaceutical corporations and many other things that she didn’t like to bring up in conversations. But whatever they were, they brought in the big bucks for sure.

She ran most of it from the comfort of her home. When you were that rich, you could apparently do stuff like that. But anyway, he walked to her office and knocked on the door. “You may enter.” was the response he got.

He sprayed a bit of breath spray in his mouth and walked in. “You wanted to see me, Grace?”

Diego paused as he saw her with a rather serious expression on her face. He tried to cheer her up. “To what do I owe the pleasure of you summoning me in your beautiful presence?” he said winking at her.

This did not move her, nor did he get a response out of that. “Uh…did I say something wrong?”

“The wink was too much, you idiot!” he thought to himself.

“Sit down, Diego.”

He did so. She then placed the Small Town Inquisitor in front of him. “Turn to page 50 and tell me what you see.”

He did so and saw Gracie’s ass, front in center on the page. He burst out laughing at this turn of events, but then he looked back at Grace, who looked like she was staring daggers into him. This made the laughter die in his throat rather quickly.

“AHEM….uh…I see, a butt?”

‘Whose butt?”

“Uh…Gracie’s?

“Correct. Care to explain why it’s there?”

He realized why he was really here. He gulped as he tried to lie his way out of it. “I have no idea ma’am. I mean, this is a really far away picture. Looks blurry as heck so I have no clue who could’ve taken it and sent it to these vultures.”

“Mhm…sure. Turn to the next page.”

He did so. “Look at the picture I’ve circled in red, do you notice anyone familiar?”

Whoever took this picture somehow did it from multiple angles as there was another smaller picture of her, running inside the mansion, hat already covering her backside. But just off to the side, was Diego, laughing his ass off, phone in hand.

Diego started to sweat as he tried to think of a plausible explanation for his presence there. Mrs. Grayson didn’t even give a second to think as she told him, “The other employees told me everything.”

She got closer to him as she then added, “Gracie told me everything.”

“Mrs. Grayson, I swear that I didn’t submit any pictures. I genuinely have no clue who sent them in!”

“I know you didn’t, that’s not what I’m mad about. I’m mad about what you did to Gracie.”

“With all due respect ma’am, she kinda deserved it for all that she did to me and the rest of the employees and-”

“DIEGO!”

He stopped. “Y-yes ma’am?”

She took a deep breath and said in a tone that sounded soft, but at the same time angry, “I’m well aware that Gracie is a handful, but we discussed a fitting punishment for her and we put it into action. She was already punished so there was no need to add onto it.”

She then stood up and looked down at Diego who was still sitting down. “Gracie is of course many things. I’ve heard them all. She’s a menace, a monster, a heartless “bitch”, a spoiled brat and so many other insults that frankly, as a mother I should feel personally offended by, but I understand. I used to be like that in my youth, but I outgrew that when she came along.

I’ve tried my hardest to mold her into the mature and responsible woman that I know she’s capable of being and I’m well aware that I might have failed.”

“Grace, you didn’t fail, she’s just very headstrong and-”

Grace held out a hand as if to say “stop” and then continued when Diego shut up. “That being said, there is one thing that Gracie is first and foremost. The one thing that I wish so many people who think she deserves retribution for the many things she does, would understand.”

She then leaned forward and then said, “Gracie…is…my…DAUGHTERRRRRRRRRR!!!

She slammed her hands onto the desk startling Diego as she screamed that last part out with a look on her face that looked like she was about to bite his head off. But that wasn’t the end of it.

“SHE IS MY DAUGHTER AND I WILL NOT TOLERATE ANYONE WHO MEANS HER HARM IN ANY WAY SHAPE OR FORM! I DON’T CARE IF SHE DESERVES IT OR ASKED FOR IT. NO! I WILL PERSONALLY SEE TO IT THAT ANYONE WHO HURTS HER WILL BE PUNISHED TO THE FULLEST EXTENT OF THE LAW!

IF YOU ATTEMPT ANYTHING LIKE THAT EVER AGAIN, YOU WILL BE TERMINATED. FIRED. UNEMPLOYED AND I CAN GUARANTEE THAT YOU ARE ILL EQUIPPED TO HANDLE WHAT I’M PREPARED TO DO WITH YOU. DO I MAKE MYSELF CLEAR!?”

“MRS. GRAYSON, PLEASE. THIS WASN’T NEARLY AS BAD AS WHAT SHE DID TO ME, WITH THE WHOLE NUDIST THING. I FEEL LIKE SHE LEARNED A REAL LESSON H-”

“AM. I. CLEAR. DIEGO!?” she said getting right up in his face.

“AS CRYSTAL MA’AM!” He said, saluting her as he was terrified of her anger.

“GOOD. NOW GO TO YOUR ROOM AND DO NOT COME OUT FOR THE REST OF THE DAY. I WILL DISCUSS THE TERMS OF YOUR PUNISHMENT WITH YOU FIRST THING IN THE MORNING.”

“YES M-Hold on a second. Are you grounding me? With all due respect ma’am I’m not a child, I’m your employee and-”

“NOW!!!”

“YESMA’AM!RIGHTAWAYMA’AM!”

Diego then ran out of the room almost tripping over himself as he sprinted back down the hall back to his room. He closed the door behind him and locked it. “Good job, idiot. Guess you can kiss your presumed title of Mr. Grayson goodbye.”

“Shut up…me.”

A few hours later he heard a knock on the door. He opened it and one of the maids brought him some food. Good to know that Mrs. Grayson was at least still kind enough to give him something to eat after that fiasco.

“So…is she still upset with me?”

“She’s upset with most everyone, I’m afraid. It’s best to keep out of her way when she gets like that.”

“I guess, I really blew it huh?”

“What do you mean?”

“That was kind of my fault. I should’ve left well enough alone.”

“Maybe, but if nothing else, it was a fitting revenge prank.”

“Heh, yeah. But I just hope Mrs. Grayson eventually sees the humor in it…”

The next morning, Diego woke up and walked to Mrs. Grayson’s office. He just hoped whatever punishment she had in mind for him wasn’t going to be as cruel as what he did to Gracie. There’s no way right? Thoughts of him going back through that nudist nonsense went through his mind.

He knocked on the door and was told to come in. Inside was Mrs. Grayson. But also with her was Gracie. She looked real smug as Grace beckoned him to sit next to her. That face filled him with unease.

“Ok, Diego, since you took it upon yourself to punish Gracie after we discussed her punishment, I thought it would be only fair for me and Gracie to decide what your punishment is.”

“Uh…really?”

“Yes, really. After much back and forth we have settled on a rather unorthodox punishment.”

“Oh god, I’m gonna have to get naked again aren’t I?”

“No. In fact nudity will not be involved here in any way shape or form…for now.”

“Oh…good.” He said, feeling uneasy about the “for now” in that statement.

“Your punishment is…”

Grace then paused and sighed, turning to Gracie and asking her, “Are you really sure about this? I…don’t see this as a punishment.”

“Oh trust me, he’ll hate this…” she said, looking at Diego with a smug grin.

“Very well. Your punishment is to….take her out on a date.”

Diego’s eyes went wide. “I…must’ve heard that wrong…there’s no way that my punishment is to take her out on a date, right?”

Gracie giggled, “Yup. You’re gonna go out and show me a good time. Or else…”

“I…uh….Mrs. Grayson, you can’t be serious.”

“I am. You both will have a great time. I’m sure of it.”

Diego chuckled in disbelief. “Isn’t there anything else I could do instead?”

Gracie got offended at that and stormed out of the room, slamming the door behind her. Diego thought he was about to get another tongue lashing and braced his ears and his heart for this. But instead, Grace simply sighed and said, “Look, I’m aware that you’re not exactly on the best of terms with Gracie, but could you at least meet her halfway on this?”

“Halfway!? Mrs. Grayson, she blackmailed me, stripped me naked, forced me into nudity and indirectly humiliated me in front of hundreds of women! The fact that I didn’t sue is something she should be thankful for!”

“True. That fact alone is the only reason why I have not thrown you out for what you did to her. But a punishment is a punishment. Once she’s done with her shift, you are to take her wherever she wants, do whatever she wants and I want you both back no later than 10 pm. Got it?”

“But Grace-!”

“No buts! I personally wanted you to go bottomless while me and the rest of the employees took embarrassing pictures of you. Just so you knew what it felt like.”

“I already knew what that felt like…” he said, trying his best not to get angry as he couldn’t believe the levels of double standard he was experiencing.

“Ok, in all seriousness, I just want you both to get along if nothing else. You…are aware of how she feels about you, right?”

“I’ve heard rumors of her having a crush on me.”

“Diego…after you cooled off from the hot tub, Gracie couldn’t stop talking about you. She practically drooled over you as the nurse tried to get you off the floor.”

“Ok so she thinks I’m sexy…she doesn’t know me in the slightest. Plus, she’s annoying, only cares about herself and even before the nudist incident, constantly teased me about my…shortcomings as I was lifted out of the tub.”

“Not the best first impression, I’ll give you that, but I’ve told her to be on her best behavior. Besides, it’s this, or you’re fired. Got it?”

“Yes ma’am.”

“Good, now go ask her out.”

“WHAT!? But she already knows-”

“Yes, but I want you to ask her herself.”

“This is ridiculous, but…if I must.”

Diego then went to Gracie’s room. “This is for Grace and nothing else. All I have to do is just suffer a bit more of Gracie’s BS and then I can just avoid her for the rest of my time here.”, he thought to himself as he did so.

He got to her room and knocked on the door. “Gracie? I need to ask you something.”

“Go away.”

“It’s important. I need to talk to you.”

“Fine. Just wait a bit…”

“You need to get to work just come out and let me ask you this.”

“Give me a bit!”

“Fine, I’m coming in there.”

“NO DIEGO! I’M SERIOUS DON’T I-!”

He opened the door and walked in. “Gracie, look I was told to ask you out on a d-”

He stopped as he realized why Gracie told him not to come in. Gracie’s hair required a lot of maintenance. As such he confirmed that her spiked up ponytail thing was indeed fake. But that’s not what stunned him. It was the fact that in order to put on her groundskeeper shirt, she had to remove it. She was currently in the process of doing so, thus she did not have the shirt on.

…or anything else for that matter.

She had her hands behind her head and thus Diego saw EVERYTHING. She had c-cups, possibly going on d-cups like her mom and her skin was flawless. He briefly wondered if she tanned in the nude, considering she had no tan lines to speak of.

And right between her legs was her vertical smile. Clean shaven except for a small dollar sign made of brunette hair right above it.. Guess she really was a natural brunette. Though he still questioned why it was shaped like dollar sign. Not that it wasn’t cute to him…in a absolutely hilarious way and not any other way. Or at least that’s, once again, what he told himself.

Those bluish teal eyes of hers were wide as they could be as both of them processed what they were both seeing. With a massive blush on both of their faces, Diego slowly backed out of the room without another word and gently shut the door behind him. He turned around trying to process what just happened.

Still in front of Gracie’s door, he thought to himself, “Alright. I’ll pretend that didn’t happen. Heh, I’m kind of surprised. She took that a lot better than I thought she wou-”

His thoughts were interrupted by Gracie, now fully dressed, putting him into a chokehold and dragging him back into her room. “OH BOY.”

With her slamming the door behind her, you could hear Diego screaming from behind the door as she proved to him that despite being the spoiled daughter of a rich woman, she could absolutely hold her own in a fight. “NO PLEASE! GRACIE, I SWEAR IT WAS AN ACCIDENT! PLEASE STOP! NO! OW! I’M SORRY!”

With an ice-pack on his head and a few scratches on his person, he sat back in the office along side a pissed off Gracie. “In fairness, maybe I could have waited a few seconds there.”

“You think!?” said Gracie.

“Gracie, just head off to work. I’ll deal with Diego here.”

She stuck her tongue out at him and left for work. Leaving him and Mrs. Grayson alone in her room.

“I’m fired, aren’t I?”

“Not yet…If only because I can see you’re remorseful…and bleeding. You have one more chance to do this. If there is a single nudity incident from this point forward…that’s it. Do you understand?”

“Yes ma’am.”

“Now, once she’s done with her shift ask her again.”

“I’m not sure she’ll even want to after this point…I think I really made her mad here.”

“You’d better hope she does, cause if you don’t take her out on that date, you’re out of this house. You got it?”

“Got it…”

He then left to go disinfect a few of those scratches and waited for Gracie to finish her duties.

As Gracie was busy mowing a lawn with a fancy riding mower, she thought to herself how humiliating this entire thing has been. “First he sees my vag, then my ass gets published in a magazine and now that idiot sees my breasts!? WHY IS THIS HAPPENING!?”

No other guy has ever done this to her. She usually humiliates other people, but for the past week, he’s been constantly screwing her over. And yet…she couldn’t stop thinking about him. That face of his going wide-eyed as he saw every inch of her. Her heart palpitated as she replayed that moment in her head.

She wanted to be upset. She wanted to beat the ever loving snot out of him for that and she did. But once the anger left her and she kicked him out of the room, she felt something inside her. She couldn’t describe the feeling but it was like she wanted that to happen again…

She then shook her head and tried to get that thought out of it. She wasn’t an exhibitionist like that little dickhead. She’d never want to flaunt herself in front of anyone, let alone this stupid, tiny dicked, idiotic, poor, roguishly handsome, jackass with a body that she’d never want to hold or touch or kiss or…

“GRACIE!”

“Wha?”

One of the employees tending to the garden dove out of the way as Gracie realized that she was mowing through a flower garden that several gardeners had been tending to all day. She stopped in the middle of it as she turned off the engine. A few of them looked at her with a look of pure wtf, as Gracie looked behind her seeing the destruction her distracted mowing had caused.

“Hehe…whoops.”

She had a long day of replanting ahead of her…

A few hours later, now that his wounds were bandaged up. He went back to her room and tried once more. He had on a light blue tuxedo that he originally was going to wear to his senior prom, but due to a lack of date, he never wore it. Thankfully it still fit. He hoped she’d still want to date him after that accidental breach of privacy. It was 5pm, so Diego only had 5 hours to convince her or else he was fired.

He even had a few flowers on hand to try and entice her to him. Those flowers were originally for Grace but, he knew she wouldn’t be in the mood to accept them now. He knocked on the door. After a bit of silence she opened the door, still dressed in her groundskeeper uniform.

“Hi, Gracie! So about earlier I-”

She slammed the door in his face. He stood there stunned. He knocked again.

“GO AWAY!”

“Gracie, did you forget your little punishment idea? Well…I’m here for it.”

“Get lost!”

“Gracie, look I’m here, I’m ready to take you out against my will, what more do you want from me?”

“Nothing! Go back to my mom, since you love her so much!”

“THAT’S THE THING. IF I DON’T TAKE YOU OUT, I’M GOING TO LOSE MY JOB! PLEASE GRACIE, YOU WERE THE ONE WHO WANTED THIS IN THE FIRST PLACE!”

“GET BENT!”

“Gracie, please! Look, I even brought you flowers!”

“I’VE SEEN ENOUGH FLOWERS FOR A LIFETIME, DIEGO! GO! AWAY!”

Not that Diego wasn’t used to girls rejecting him, but he knew if this one did, he was going to be a lot worse off for it. “Gracie, I need this job and not just for the money. I’m happy here. I finally had someone who loved me and she happened to be the most beautiful woman in town, but I blew it all over a stupid prank.

I have a ton of money saved up thanks to the days I worked and I could survive off that for a few months, but I’d be back home. Alone…with no one. Even if this works and me and Grace never get romantically entangled, I’d still have more friends here then I ever had back home. Please…just humor me here.

I’ll do whatever you want as long as I can keep this job…”

He then paused as he remembered that Gracie’s main goal in that earlier blackmail attempt was to have him quit. Being fired was essentially the same thing, so by telling this to her, he just gave her what she wanted. Except now, he wouldn’t even get to speak with her again.

While he was glad about that part, the thought that all his ties to Grayson manor were about to be severed caused him to fall into despair. “Fine…it’s not like I’m not used to this. I’ll go tell Grace you said no and I’ll pack my things. For what its worth Gracie…I hope you do find someone who can tolerate you.”

He dropped the flowers to the floor and walked off. But just as he walked away, the door opened and Gracie walked out. “You really are desperate, aren’t you?”

“If this is the only way I get to keep my job and make it up to Grace, then I’ll do it.”

Gracie sighed and then said, “Give me a minute to think about it…”

She then went back into her room and closed the door. After a bit, she started to squeal. “YEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEE! IT’S HAPPENING!!!! IT WORKED, HE’S MINE!!!!”

Gracie started to do a happy dance as she couldn’t believe it worked. Despite everything that’s gone wrong, she finally got him! Diego was hers! She couldn’t believe it. After a bit of dancing in joy of her finally forcing this peon to fall in love with him, she composed herself.

With a stone faced expression she opened the door once more to talk to him. “So, I do have an opening in my schedule tonight. I might be able to squeeze in that date with you, if you give me an hour to get ready.”

Diego with an unamused expression replied, “You do know I heard that entire thing from out here right?”

Gracie stammered a bit as she tried to move past that. “Uhhh…Well, go get ready, I’ll meet you in at the front of the manor when I’m dressed.”

“But I am ready.”

“What?”

Gracie looked him over. “Ew, you look like that blonde guy from Dumb and Dumber. We have tailors. Go get a suit from them, they’ll make you look presentable.”

“Gracie, I think I look good.”

“Well, if you’re going to be with me, you need to look great. Go get something better or the date is off.”

Diego groaned. “Fine…I’ll go change.”

Gracie went to go get ready while Diego went to go tell Mrs. Grayson that they were gonna go.

“Grace, she said yes. So what do I do now?”

“Good, now you two better behave your…selves…” she trailed off as she saw him standing there.

“Why are you dressed like the blonde guy from Dumb & Dumber?”

With a exasperated sigh he then asked for directions to the tailors.

Now clad in a full black tuxedo and black shoes (with a blue bowtie as he was insistent on at least having something blue on his person), he waited for Gracie by the front. “Ok, relax, all you have to do is take this brat of a woman out on a date and you can go back to trying to regain her mom’s respect. Simple. Just endure her BS for a bit longer and you’re good.”

He psyched himself up for this thinking that nothing would complicate matters. That is until he saw her come down the stairs. He couldn’t believe his eyes. She had a different, much shorter purple dress on. The dress had a purple bow in the back and was strapless.

As she got close to him, he could smell her fancy perfume. It was the same scent that Mrs. Grayson usually wore. She had purple eye shadow, mascara and lipstick on. She really liked purple. Can you tell?

Diego was stunned as she looked vastly different. “W-wow….”

“Hehe…like it? I thought you would.”

“Uh…yes. It’s a good look and now it’s time for our….our….d-da….”

It fully hit Diego what he was about to do. He was about to take one of the most well known and influential people in town on a date. It didn’t matter that this was Gracie, it didn’t matter that he hated her, she was still an outright celebrity in this town. She was way out of his league.

He froze up. He had no idea what to say or do. His heart was going a mile a minute as she stared at him. She snapped her fingers in front of him in order to bring him back down to earth. “Hey, peon! Let’s get going!”

“RIGHT, OF COURSE!” and they walked out of the mansion to the front garden.

They waited by the valet, who was instructed to bring a limo around so that Diego and Gracie could go someplace fancy. Grace gave him 500 dollars to play around with and he ordered him to spend it only on dating activates and nothing else. This wasn’t necessarily because she didn’t trust him with the money. It was more like she didn’t trust Gracie with the money.

While this was a punishment for Diego, she reminded Gracie that she was still punished, so no expensive gifts or things other than dinner and perhaps a movie or some other type of activity. As the limo drove them around, Diego sat there, completely catatonic. Gracie started to get annoyed by his silent panic as he wondered what he could do. If he did anything to humiliate Gracie even unintentionally, it was over for him.

“You gonna say anything or are you gonna just shiver like a chihuahua?”

“Uhh….heh….uhhh….so, what do you want to do?”

“Impress me. Take me out to someplace that will thrill me, Diego.”

“Like where?”

“Well, where do you usually go out for dates?”

His eyes went wide as he wondered how to answer that, but his hesitation clued her in on what he would’ve responded with. “Oh my god….you’ve never been on a date before have you?”

“No….”

“Awww…I take it that you never got far enough to show anyone that wittle weewee either huh?”

He got annoyed and looked away from her as the limo drove them around.

“Your silence speaks volumes, my little peon. Hehehehehe~”

“Fine, where do your dates usually take you?”

Gracie immediately stopped giggling. “Uhhh….lots of places of course. I’ve had a lot of dates. Several guys. Tons of them. I had to cancel 3 dates just to squeeze you in.”

“Gracie, I-”

“I’ve had lots of sex too, twice as much as you!”

Diego chuckled and mumbled under his breath, “Two times zero is still zero…”

“SCREW YOU, I’M NOT A VIRGIN!”

He was taken aback as Gracie looked like she was gonna smack him for that. “Gracie, all I asked was where you wanted to go. There has to be some place that you want to go. Your mom did say I had to do whatever you wanted.”

“Oh….well…how about something to eat?”

“I mean, yes…but what?”

She thought about it for a second and saw a fancy Italian restaurant as the limo drove them around. “There! Driver, drop us off here!”

The driver found a place to drop them off. This restaurant was close by a boardwalk. A fancy seaside Italian place simply known as Posto italiano elegante sul mare. It definitely sounded fancy, but most things said in a Italian did.

The driver told them both that she’d be back at around 9:50, but if they needed to be picked up sooner, either of them could call and she’d be there. As she drove off they stood in front of the restaurant. It was now 7:00pm.

“Uh…well, let’s get going Gracie…”

He got her hand and walked her to the door.

“Uh…Diego, what are you doing?”

…”Uhh…walking you inside?”

“I can walk inside on my own thank you!”

And with that she slapped his hand out of her hand. He shook his head and walked inside.

….”DIEGO!”

He heard her scream from outside the restaurant. He walked outside once more. “What now?”

“You didn’t hold the door open for me! A proper gentlemen holds the door open for a lady.”

With a grunt of frustration he held the door open for her as she walked in side. “THIS IS FOR GRACE. THIS IS FOR GRACE. THIS IS FOR GRACE…” he repeated that to himself as he was sure that she was not going to make this easy for him.

As he walked in he saw that numerous people were waiting by the maître d’, there was a big line and many people were waiting around, seems like it was packed. He approached and asked for a table for two.

“Certainly, do you both have a reservation?”

“We don’t, sorry. How long will we have to wait?”

“About two hours. My apologies.”

Gracie heard this and was very unhappy. “TWO HOURS!?”

“I’m sorry miss, but you should’ve booked a reservation.”

“Let’s just go somewhere else, Gracie…”

“NO, I WANTED THIS PLACE AND WE ARE GOING TO EAT HERE NOW!”

“I mean, if we wait we still have about 50 or so minutes to eat.”

Not satisfied with that answer, Gracie turned to the maître d’ and said the phrase that most people who have to work in a field involving any sort of contact with people on a daily basis dread the most. Not because they fear it, but because they know that they were in for one hell of an annoying time.

“I’d like to speak to your manager.”

Diego had his felt his heart sink as he felt the shame of her invoking those horrid words, for no good reason. He covered his face in shame as the manager was dragged out to this discussion.

“What seems to be the problem, young lady?”

“TELL THAT GUY TO LET US IN RIGHT NOW!”

Gracie then pointed at Diego, to signify that he was with her. All Diego could do was sheepishly wave and mouth “I’m sorry.” at the manager. The manager was not having any of it. “Ma’am, you should’ve booked a reservation. I apologize but there is a wait and we’re not going to let you cut in line.”

Pissed, Gracie grabbed him by the shirt collar and brought him close to her face as she asked him, “Do you know, who I am?”

Diego had enough. He grabbed Gracie by the arm and tried to pull her from him. “Gracie, enough! Look, we can’t just expect special treatment because you’re rich. Now let’s go somewhere else.”

That’s when both the maître d’ and the manager had their eyes open in shock. “Sir! Wait! What was her name again?”

She answered for him. “Gracie Grayson.”

“Oh my god….” the manager looked like he was about to faint. He then whispered something into the maître d’s ear and he ran off. After a bit he returned. “My mistake you two, a table just opened up. So sorry for the inconvenience.”

“Hmph, well, thank you. Come Diego, let’s go eat.”

Diego was stunned as he followed her. Sure enough they were lead to that a few waiters were quickly clearing out. It seemed to have a few unfinished plates of food and a few of some couple’s personal belongings that were left behind. Almost like they were quickly ushered out to make room for Gracie and Diego.

Once the table was set, they sat down and were handed some menus. Gracie looked smug as she saw Diego’s bafflement at how they were seated so quickly. “How did you do that?”

“Do what?”

“You got them to comply so fast. We were nowhere near next. I think a few of the people who were waiting gave us some dirty looks.”

“The perks of being the daughter of the richest person in town. One compliant and mom buys out the restaurant. Hehe.”

He was stunned. “That’s just…I…does she do that often?”

“No….but she could and I make sure they know that.”

“But that wasn’t fair.”

“What are you complaining about? We got in, you should be happy. When you’re with me, you can do anything.”, she said with a grin on her face.

“I suppose….”

The waiter then came by to ask for their drink order. Diego ordered a Diet Soda and a water with lemon. Gracie meanwhile asked for the wine menu.

“Wait, you drink?”

“Well…yes. Someone as sophisticated as myself drinks quite often.”

“Gracie that’s not exactly sophisticated.”

“Well, mom drinks a lot so why can’t I?”

“Wait she does?”

Before she could answer, Gracie was brought the menu. “I’ll have a bottle of your most fanciest wine, please.”

The waiter complied and picked the fanciest (read: most expensive) wine they had. He then took their orders.

Gracie looked over the menu but seemed to be confused. “Wait, this place doesn’t have pizza? I thought this was Italian.”

“I guess they don’t.” Diego said, before ordering some 5-cheese pasta.

“Fine. Waiter, your finest mac and cheese please.”

The waiter looked confused and Diego sighed as he whispered to the waiter. “Another order of 5-cheese pasta for her too.” he went off with the orders in hand.

Diego rubbed his temples as he couldn’t believe that, SOMEHOW, Gracie was even more annoying outside the mansion. Gracie looked at him and asked, “So how’re you enjoying the date thus far?”

…”Do you want my honest answer or a lie?”

“Whichever one is the answer where you say that you’ll be mine forever. Hehe~”

He sighed and didn’t answer. “Hey, my mom told you to be on your best behavior right?”

“Yeah?”

“So love me already!”

“That’s not how this works, Gracie!”

“Loving me would be great behavior.” She said with a smirk on her face.

“Gracie, it’s not going to happen. We haven’t even gotten our food and you’ve made a scene, been rude to the staff and I’m already wondering when this is going to be done.”

“Come on! What must I do to make you fall for me?”

“Be nice to people other than yourself, for one!”

“I’ve been nice to you, you idiot.”

“Nice people don’t call each other idiots. Although, I feel like one for letting this happen.”

“Well, tell me! What do you like? I can get you into any place you want. I’m loaded. When my punishment’s over we can go somewhere better and you can spend as much as you want….on me of course. Hehe~”

“For one, I like not being forced onto dates by women who blackmail someone with a fake recording of them getting abused and who don’t force them to walk naked through a mansion like it was a perfectly normal thing to do. I also like girls who aren’t full of themselves, who don’t think that they’re better than everyone and who DON’T MAKE LIFE FOR EMPLOYEES AT SAID MANSION A LIVING NIGHTMARE AND-”

Diego looked around, everyone was giving him a concerned look. He tried to compose himself and pretended that that outburst didn’t happen. He then looked at Gracie who had an angry look on her face.

“I’ll be right back, Diego.” she said, getting up and walking to what appeared to be the restroom.

“Hoo boy….this isn’t gonna end well, is it?” he thought to himself.

The waiter came back with his soda and water. As Diego took a sip of his soda, he wondered if Gracie was going to get him for that outburst. But he remembered that Grace told her not to do anything to him. So, it’s not like she could do anything, right?

“Oooooh, I’m going to get him for that outburst!”

Gracie was pissed. That little peasant wouldn’t know sophistication if it bit him in his giant ass. She decided that if he couldn’t get him to love him, she could at least get him fired. All she needed was another nudity incident. But, she wasn’t too sure about exposing herself.

But then it dawned on her. Her mom said a nudity incident, she didn’t say that it had to be Gracie’s nudity and she said Gracie couldn’t strip or prank him, but what if someone else did? She got her phone and called a friend of hers.

“Hey…it’s Gracie. I need you to do your thing…..you know, the stripping. I know someone in dire need of a pantsing. Think you can do that for me?”

The voice on the other end, agreed. “So where is this target?”

Gracie looked at her phone. “He’ll be at the boardwalk at around 9:45. I’ll distract him, you pants him. He has tan skin, black hair, is wearing a black tuxedo with a stupid little blue bow tie and, get this….hehe….he has the smallest little hairless dick you’ll ever see.”

“No kidding?”

“Yup.”

“Oooh, sounds fun. I’ll be waiting.”

“Bring some friends, trust me, it’s hilariously tiny.”

She hung up, confident in her plan. But that was just step one. Step two was a lot tougher. She called another number. On the other end was a rather sleazy individual. “Small Town Inquisitor, this is the gossip department, what have you got?”

She pinched her nose to disguise her voice. “Hello, I heard a rumor of a guy around the pier who likes to pull down his pants and flash people his tiny cock.”

“Really? Hmm…is he there frequently?”

“Yup. He usually makes his move at around 9:45 or so.”

“Hmm…that’s a bit specific.”

“Oh…uh….he works with clockwork regularity. Obviously he has no life, what with the tiny cock and all.”

“Fair enough. Who might I ask is giving us this info?”

“Uh….just put me down as G.G.”

“You got it. We here at S.T.I. appreciate your input.”

“Thank you.”

She giggled evilly, that’ll teach him to spurn her. But now she just had to keep him occupied until that time. She went back to the table.

Diego was playing with his phone, wondering when Gracie would return. She didn’t walk out on him, did she? It would probably look bad if he arrived back at the mansion without her, so he was just about to text her when he saw her walk out of the bathroom.

“Oh thank goodness. I thought you left. What took you so long?”

“Girl stuff.” she curtly replied.

“Look, I’m sorry about that whole thing earlier.”

“No it’s fine….I know I’m not gonna win you over, let’s just eat and get out of here.”

“I mean….I don’t think you’d win me over, but that doesn’t mean you give up.”

She looked at him in confusion. “What do you mean by that?”

“You have me here. You got me out on a date. This is your chance to win me over. Just be a bit nicer to be around and who knows….maybe it could work.”

He smiled, knowing full well that was BS. His opinion of her was pretty low, but maybe if he makes her think there is a chance, she won’t be a nuisance for the rest of the night.

“Why should I win you over!? I’m perfect. You’re the problem.”

“If I’m the problem, why do you even want me? You’ve done nothing but insult me and be a nuisance for the past week. I can’t tell if you actually like me or want to see me suffer. Currently, you’re doing a great job at convincing me that it’s the latter.”

Gracie didn’t know how to answer that. “But I’m pretty. I’m rich. Isn’t that enough?”

Diego sighed and said, “No…no it’s not. That’s nice, but it’s not what I really want.”

The wine was then brought to the table. As the waiter poured a glass of wine for them both, Gracie told him to leave the bottle.

Diego tasted the wine. He recoiled. “I’m not that much of drinker.” he said, drinking the water to get rid of the taste

“Fine more for me. Clearly you don’t have as refined a palette as I do.”

“Says the grown woman who ordered mac and cheese at an Italian restaurant.” Diego thought to himself.

She then took a sip and almost spit it back in the glass. It was rather bitter as she wasn’t used to the taste of alcohol more potent than beer. As Diego looked at her with a bit of a smirk, she forced herself to swallow.

“Mmm….its good….you can really taste the…grapes and….stuff. Heh….”

“Right….”

The food was then brought to them. As they both dug in to their plates, he wondered what he could do to salvage this date. He then had an idea.

“How about we play a game? It’s called the compliment game. It’s simple. All we do is take turns complimenting each other on things we like about the other person. I’ll go first.”

He then thought about what to say. “I think your makeup is beautiful. You definitely have a great sense of style and your eyes are very lovely.”

“Awww…thank you…” she said with a grin and a blush on her face.

She then continued eating. Diego sat there for a bit. He then gestured like he was waiting for something. “….Well?”

“Well what?”

“Your turn!”

“Oh, right! Umm…..”

Gracie took a bit to think. “You’re hot.”

Diego was taken aback by that rather blunt compliment, but still he asked her, “…and what else?”

“What do you mean, what else?”

“I mean…anything more specific or…less superficial?”

“Ugh….alright, ummmmm….”

Diego waited a bit but Gracie took a bit too long for his liking.

“Really….nothing?”

Gracie blushed and was unsure what to say. She drank a bit more wine and went silent.

“Look, it’s not hard. For example you’re…uh…”

Diego felt a bit sheepish he couldn’t think of anything else either. He chuckled as Gracie looked at him with an unamused look on her face.

“Heh….uh…well, I guess it’s a much harder game then I thought.”

They both just went back to eating. He looked at his phone, it was only 8:15. Time sure did crawl when you were on a disaster of a date that you never wanted in the first place. He then noticed Gracie pouring herself a glass of wine. She finished her first one.

She looked like she was choking it down. “You know, you don’t have to drink that right? I can see you don’t like it.”

“Ss-shut up! I can do what I want…you’re not my *ugh*…mother…”

As she drank more of it, she put the glass down and remarked, “If I was my mom, maybe then I’d have better luck. Why d-do you love her anyway…she’s old and…not…young. Do you like MILFs or something?”

“NO! I just….think she’s beautiful and…sweet and…uhhh…she has a commanding presence?”

Gracie chuckled…”Most guys think she’s bossy.”

“I mean, that’s the mean way to put that, I suppose. She’s just rather commanding and yet so gentle, when she isn’t mad. It’s almost like I want to do everything she says, no matter what.”

Diego started to get a bit of a blush as he thought of the things that she’d command him to do…Let’s just say none of those involved groundskeeping related activities.

“So, you just like women who dominate you?”

“WHAT NO! T-THAT’S NOT IT AT ALL!”

Gracie giggled. “Well then why my mom? I’m sure there are many younger women who could do things like that with you…Hehe~”

Diego was a bit put off by this. Even more so when he noticed Gracie finished her second glass of wine. She had a bit of a blush on her face and a smile on her face.

“Uhh…you feeling alright Gracie?”

“Just….peachy….”

She then put her elbows on the table and held her arms in her hands just staring at him. Her elbows were right in her food. Diego asked one of the waiters for a glass of water for Gracie.

“I think you’ve had enough to drink, Gracie.”

She let out a small burp. “Oops…heh, excuse me.”

At that, Diego tried to ask for the check, but before he could, Gracie got his attention.

“Hey…let’s play that compliment game again. I thought of a few…”

“Really? Alright, let’s hear them.”

“I…think you’re sexy. I think every part of you is something special, even that tiny cock of yours.”

Diego’s eyes went hide as he heard that. “Haha…thanks Gracie…”

“No, I mean it. That thing looks like an adorable little mushroom. I just wanna take it and do all kinds of things with it. I bet it would feel so good in my-”

“Gracie! Thank you but, could you not say that stuff here!” he said, noticing some of the other restaurant patrons were looking at them both. A few of the female ones even chuckled as they saw him look around.

“What? That’s a compliment. I swear. I love your eyes, I love your toned body. I love that blush you get when someone mentions your itty, bitty, teenie, wittle mini baby dick! I want it so bad!”

Diego had his hands covering his face as he blushed red enough to look a like a tomato.

“Gracie…please stop…”

“Why? Does it make you embarrassed? Flaunt it.”

She then got up on top of the table. “EVERYONE. DIEGO IS MY BOYFRIEND NOW! YOU CAN ALL STOP TRYING FOR ME. HE AND HIS ADORABLE LITTLE MICRO COCK ARE MINE AND NONE OF YOU CAN HAVE HIM! AND THERE’S NOTHING ANY OF YOU CAN DO ABOUT IT!”

She then got down off of the table and sat down like nothing happened, giggling at Diego’s humiliated expression. “Hehe…your turn, cutie.”

He was stunned and utterly mortified. He motioned to one of the waiters. “Check, please.”

After leaving a rather generous tip for the scene she caused, Diego took Gracie by the arm and lead her out of the restaurant. She had a bit of trouble walking a straight line and kept leaning on Diego for support.

Once they were far enough from the restaurant, Diego got mad at her. “WHAT IS WRONG WITH YOU!?”

“What? They were all jealous of me…you saw them. A few of those ladies looked sad cause they couldn’t have you.”

“No, they looked sorry for me! I can’t believe you would say those things in front of everyone.”

He rubbed his face in frustration. He looked at his phone. “9 o clock. I’m calling the limo back, this is good enough I feel.”

That’s when Gracie remembered her plan. She had to keep Diego here for a bit longer. “Wait…we could do something else until 9:45!”

“Well, we need the limo here by 9:50 so…I guess we can do something else, IF YOU BEHAVE!”

“I’m…not a child, sir. I’m just….something.” she said stumbling a bit.

“Ok, hold on there. Maybe we should wait a bit.” he said to her as he kept her on her feet.

“Grace is probably going to kill me if I bring you home drunk as a skunk…” he then thought to himself.

“Yay.” she said in happiness as he took her hand once more.

They walked around the boardwalk. Everything there was closed so there wasn’t much to do other than walk around. As they got to a bench that overlooked the ocean they sat down. All you could hear was the sound of the ocean waves.

Diego kind of liked the peaceful sound of the ocean. Gracie leaned on him as they took in the beautiful night sky. The moment was ruined by Gracie putting her hand on his face.

“Can I help you?”

“I just wanted to get a good look into your eyes. I can’t do that if you keep looking at the water.”

He then took her hand and gently took it off his face. “Gracie, just…could you just be quiet for a bit. Sometimes, it’s just good to listen. Somethings don’t need to be said when it comes to romance.”

“You just want me to shut up, don’t you?”

“I mean….well…”

“No it’s ok…I’ve had people say that before.”

“Heh, really? You? Who wouldn’t want to listen to you for hours on end?” he said sarcastically.

“I know right? It’s almost like no one likes me. But that’s not possible….right?”

Diego stammered a bit trying to think of an answer. But that’s when Gracie buried her head into his shoulder and whimpered a bit. Was she…crying?

Unsure where this sudden mood swing came from, Diego patted her head and tried to calm her down. “Are you ok?”

“Why does no one love me?”

“I’ve given you several reasons for that. You’re rude to people. You treat everyone around you like they live to serve you. You humiliated so many people, including myself and you think you can get away with it all because your mom is the richest person in town.

You have very few redeeming qualities and honestly I-”

Diego stopped, he saw Gracie’s face. Her makeup was running, due to the tears. He internally debated over his next action, but he eventually got one of her hands and gently rubbed it. “Look, all me and your mom ask is this. Just try to be more considerate. Your mom wants you to be a mature woman. So, no more pranks on me or anyone else. No more trying to get anyone you don’t like fired, got it?”

“Is that what it would take, for you to love me?”

“Not really…but it’d be a start. Maybe that would be enough for me not to dislike you.”

Gracie looked like she was about to cry, but this time, it was tears of joy. “So…there’s a chance!?”

“Well…umm….y-yes?” he said, not sure of his answer.

Gracie squealed and wrapped her arms around him. He returned the hug, awkwardly. As he hugged her, he smelled a bit of her perfume, which she borrowed from her mom. The smell brought back a mental image of Mrs. Grayson and Diego hugged her tight. He had a big smile on his face as he imagined her face.

That’s when he remembered he was hugging Gracie. He released her and waited a bit, but she didn’t let him go. “Uhh, Gracie. You can let go of me now.”

She simply whispered in his ear, “I felt your heartbeat. I knew you liked me.”

“Wait, I-”

“Shhhh…just listen to the waves.”

As she said this, she ran her hands through his hair. Diego didn’t know how to react as he’s never seen this side of her before. She then brought her face closer and closer to his. He tried not to react but despite the heavy smell of alcohol on her breath, he let it happen.

His mind just kept repeating to himself, “This is for Grace. This is for Grace. This is for Grace…”

But, despite the insistence that this was only so Grace could love him again. He felt his tongue start moving along side hers as they locked lips. All of a sudden, she broke the kiss and looked at him, seductively. She then got up and ran.

Diego was surprised and chased her down. “Gracie, where are you going!?”

She was pretty fast, despite her drunken run and the fact she wore heels. But Diego chased her down until they were both underneath the board walk itself. “Gracie, what the hell is going on? First you’re all wacky and lovestruck, then you’re depressed and now you just forced your tongue down my throat and ran off!

Is there a point to this?”

She sauntered up to him once more and simply said, “Nope.”

“Figures, let’s get going.”

“Wait!”

“What now?” he said, getting real tired of all these drunken mood swings.

“Let’s go swimming.”

“Gracie. I didn’t think to pack my swimsuit on my date to the Italian restaurant.”

She leaned real close to him and said, “Neither did I.”

She then started to strip down. Once she got to her undies, Diego realized what she meant and tried to stop her. “Gracie, wait! I don’t thi-”

Her underwear hit the sand and she stood there naked. “Last one in, has a cute wittle tiny cock! Hehehehehe!”

He stood there, unamused. “Fine, go skinny dipping. Whatever, I’m not joining in.”

As he stood there, looking at Gracie’s clothes on the sand, he remembered what Mrs. Grayson told him.

“If there is a single nudity incident from this point forward…that’s it.”

Gracie was naked, in public! He had to cover her up quick! “Gracie! Gracie get back here!”

She shouted from far away, “Come on Diego, the water’s fine.”

“Gracie! Please, just get back, before something happens!”

Shockingly, her response was just a sigh and her shouting back, “Fine. I’m coming back.”

As he saw her doggy paddle back, he was relived that nothing bad happened. That’s when it seemed Gracie was getting further away rather than closer. She started to panic. “Diego! I can’t get to shore! HELP!”

Gracie was caught in a riptide. “GRACIE! SWIM TO THE SIDE! NOT AGAINST THE CURRENT!”

She was flailing about, too scared to listen. Diego then stripped off most of his clothes, (he kept his boxers.) and swam as fast as he could towards her. Gracie was nearly underwater and Diego was closing in on her. But Diego wasn’t fast enough. He got there as Gracie was sinking. All she saw as she blacked out was him, mere inches from her trying to reach out his hand.

A bright spotlight was cast on a lone woman. She looked around. She was trapped in a damp dungeon. It was Princess Gracie…or at least the former princess. For all her crimes and poor decisions made while being royalty she was now nothing more than a fool, banished from her own kingdom. All she had on were a pair of shackles and a jester hat.

Now chained to the wall in a moist and unpleasant holding cell, she realized just how badly she screwed up. Her voice was gone at this point as she yelled and screamed for any amount of help or mercy and no one answered or even listened. No one was around. She shivered. Was she just destined to die here?

That’s when she heard something. Clanking metal. The door to her cell opened and a man in a suit of armor came towards her. He had an axe in his hand. This was it, she supposed. He raised his axe in hand and she closed her eyes, just waiting for the end. He brought it down….on her chains.

It cut through them, she was free. He picked her up like a fireman and ran out of the dungeon. Despite the metal armor he was fast. As they were running, a rush of water started to chase them down. Just as it started to reach them. they got out of the dungeon.

Once out, Gracie could see a beautiful night sky and could hear the ocean. He laid her down onto the sand. He tossed away the Jester hat and looked her in the eyes. He removed his helmet to reveal…Diego?

Before she could process this he gave her a deep kiss. She felt her heart start beating again as warmth went through her entire body. He then started to…beat down on her chest for a bit.

It actually hurt a little. As he continued this she eventually started to cough up water. “BREATHE! DAMN YOU, BREATHE!” the knight said, starting to sound like he was in tears.

After a bit, her eyes adjusted, this wasn’t a knight, it was just Diego. He was wearing most of his Tuxedo, minus the jacket which was wrapped around Gracie. He gave her mouth-to-mouth once more. “Gracie…please…say something. Anything….”

After a bit more coughing she sat up, wondering what just happened. Eventually, she could fully breathe again. She felt Diego wrap his arms around her. “Oh thank god you’re ok…I thought I lost you…”

She blushed a bit as she couldn’t believe he’d ever say that to her. Eventually, though, he recoiled. “I MEAN…I’m glad that you’re ok! Your mom would have my head on a silver platter if I let you drown in the ocean.”

He then got her clothes and gave them to her. “Please, put them back on.”

She then looked down at herself and realized her nudity. “AHH! DIEGO! WHAT THE HELL HAPPENED!?”

“I’d like to know that too! You just ran off, stripped down and ran into the ocean. What were you thinking!? You almost drowned!”

She was about to chew him out when she realized something. “Y-you saved me?”

“Yes! Now put your clothes back on before I get in trouble.”

He turned away to give her privacy and she put on her clothes. Now dressed once more she tapped Diego on the shoulder to signal to him that she was clothed. “Good, now let’s get back home.”

He grabbed her hand and walked her back to the boardwalk so he could call the limo back. As he walked her back, he didn’t look at her once. Just as they got back to the boardwalk, she asked him, “Why did you save me?”

That stopped him in tracks. “I wasn’t going to let you drown!”

“But you hate me….”

“So? I can hate someone and not want them dead.”

Gracie pondered on that before she realized something. Her cheeks flushed as she did. “…You kissed me…”

“What!?”

“You kissed me! On the beach!”

“THAT WAS CPR!”

“Was it only CPR? I heard you crying for me…”

“I….well…I….”

She smiled a bit smugly as he stammered. After a bit of denial, Diego sighed. “Alright, look. Here’s the truth. I do think you’re beautiful and your little drunken escapade has convinced me that there’s something deep down in you that proves that you’re serious about this whole thing…and that you do have some good in you.

Plus, again, it would be rather morbid of me to willingly let you drown. I honestly think if you were a lot nicer and a lot sweeter, then perhaps….we…uh…”

“Could be a couple?” Gracie, said with a starry eyed look.

“NO. GOD NO. ABSOLUTELY NOT. NOT AFTER THE BLACKMAIL THING.”

She was disappointed, until he added, “But what we could be…is friends. If you stop pranking me and everyone else, if you were to behave like a civilized human being like your mom wants you to be and if you stop telling random people about my…you know.” he blushed as he said that last bit.

Gracie thought about it really hard. Maybe this was her chance to make up for everything. Her chance to take that first step to being loved again. Or even loved for the first time. She took Diego’s hands into hers and said, “I’d like that.”

After looking at her holding his hands, he starts to laugh. “What’s so funny?” she said, wondering what was so amusing about her answer.

“Sorry, it’s just that I’m laughing in disbelief at myself even thinking these things.”

“What things?” she asked, with that smug look on her face again.

Diego realized that her hands felt warm, despite being in the ocean a few minutes ago and some how that realization her her hands on his hands, made him feel warm as well. “Nothing…nothing you need to know…”

As Gracie caught him blushing, he changed the subject. “Anyway, let me call the limo now, it’s 9:45 so we should probably get going soon.”

“Yeah, this was kinda fun, maybe we ca-”

Gracie stopped mid-sentence as she remembered something important. “Oh no…”

“What’s wrong, Gracie?”

“We gotta go, now!”

“Well they said they’d be here in a few minutes so I guess we can just walk back to the restaurant an- WHA!”

Before Diego or Gracie could react, he was tackled to the ground by a few people in ski masks. They held him to the ground.

“WAIT, WHAT’RE YOU DOING!? LET ME GO!” he pleaded to them.

“This is him girls. Let’s see how small it really is!”

He tried to break free of their grip but ultimately his pants were removed along side his boxers. As he was on the floor with four unidentified individuals looking right at his penis, they started to laugh.

All he knew is that they were female. That much was clear due to their giggling laughter as they took pictures of him. One of them holding a pinky up right next to it and almost bursting out laughing at the size difference.

“HAHAHAHAHA! OH WOW, YOU WEREN’T KIDDING!” said the leader of the group to Gracie.

“THAT’S SO SMALL.”

“WHY IS IT SO SMOOTH!? DID HE NOT GO THROUGH PURBERTY!?”

“SUCH A CUTE WITTLE WEEWEE!”

Diego was too flustered to even speak as he tried to wiggle out of their grasp. Eventually, they got what they came for and left. They ran with his pants and boxers in their hands.

“That was incredible!” said one of the four girls as they ran off.

“I know right? These will be an excellent addition to my collection.” said the one holding the clothes.

“This is so much better than your skinny dipping scam.” said a third one.

The fourth one was too busy giggling over the pictures she took. She’d never seen one so tiny in her life.

All of them were laughing their asses off as Diego got to his feet and was about to chase them down, until he remembered that he was bottomless. He couldn’t believe what just happened. He covered himself as he wondered who they were.

Gracie meanwhile was aghast at that. She forgot that she set that up. Diego then realized that one of them talked to Gracie.

Still covering his front, he turned to her. She had a grin that tried and failed to portray innocence.

“You…wouldn’t have had anything to do with that, would you?”

“What? Nooooo…of course not. That was a completely random group of thugs who wanted to see your cock….honest.”

He didn’t buy that for a second. He sighed in annoyance and anger. “Why am I not surprised? I knew even you couldn’t resist pranking me when your mom SPECIFICALLY SAID NO PRANKS FROM EITHER OF US!!”

He was pissed, he went into a rant that made Gracie regret everything, even if he was so mad that he didn’t even cover himself.

“NOT ONLY AM I HUMILIATED ONCE AGAIN, BUT THOSE PANTS WEREN’T MINE! NOW I GOTTA REPLACE THEM AND I GOTTA EXPLAIN WHY I’M GOING BACK TO THE MANSION WITH NO PANTS! I’M GOING TO GET IN TROUBLE NOW AND YOU’RE TO BLAME FOR IT!”

“Diego wait, I can explain I-”

Gracie had her heart sink as she saw someone peek out from behind a trash can with one of those cameras with a massive flash bulb on it. You know, the kinds typically used by…paparazzi.

“Nonononono!” Gracie panicked as this guy was about to take a picture of Diego’s butt.

It was like everything went into slow motion as she ran behind him to shield him from the camera. Just as the flash went off, she blocked his nudity from view. This gave Diego the chance to take off his tux jacket once more and cover his waist with it.

“Hey, you’re blocking the shot of that tiny dicked flasher!”

“Get out of here! Leave him alone!”

The paparazzo had his eyes go wide as he realized who he was talking too. “Oh wow…It’s that rich chick. I gotta say, you look great. Show me your ass again! Heh…”

“Wait, THAT WAS YOU!?” she screamed at him.

“Yup, best 50 bucks I ever made in my life. I’ll make much more. I can see it now, “Gracie’s new exhibitionist boyfriend. Despite being rich, she truly appreciates the little things in life…” he burst out laughing at that.

Diego walked out from behind Gracie. “I GOT IN SERIOUS TROUBLE BECAUSE OF YOU!”

“Yeah, so? I’m not the one flashing his tiny junk at some rich girl. Gonna have to break out my zoom lens for this one!”

As he gripped his stomach in laughter, Gracie and Diego looked at each other. They both seemed to have the same thought on their minds. He then started to notice then approaching him with malicious intent.

He started to take pictures. They couldn’t hurt him with their faces documented, right?

Well, the first photo showed them both approaching with angry faces.

The second photo showed Gracie lunging straight for the camera,.

The third photo showed Diego about the punch the camera as Gracie held him onto the floor.

And the fourth showed Gracie holding up a pair of pants and underwear as Diego held the camera taking a picture of the paparazzo’s ass from a distance as he ran off with his hands between his legs.

Luckily said paparazzo was just Diego’s size when it came to his pants. So he put on his pants (the undies went in the trash because, ew.) and taunted him as he ran. “And tell the rest of the scum that works with you to never bother the Grayson family ever again!”

Both of them laughed at this. They then threw the camera into the water. “That was incredible!” said Gracie, joyously.

“Yeah, it was.”

Diego then got a serious look on his face and added, “I’m still very upset at you.”

“What!? Why?”

“YOU KNOW DAMN WELL THAT HE JUST DIDN’T SHOW UP OUT OF NOWHERE!”

Gracie was taken aback. “But…I blocked the shot. Doesn’t that count for anything?”

As Diego glared at Gracie, his phone went off. It was the limo driver. They were waiting for them. “Let’s get going.”

“But Dieg-”

“Let’s. Go.”

Without another word, Gracie followed him back to the limo. They both got in and sat in silence as they rode back to the mansion. Once they drove through the gates and the limo parked out in front. The valet opened the door and Diego walked out.

Mrs. Grayson was waiting for them both as they walked into the foyer. “So, how did it go?”

Neither Gracie or Diego responded. They both looked despondent. She sighed and said, “Come with me. Both of you.”

They reached her office and sat down once more. “Ok, what happened out there?”

Diego went first, telling her how rude Gracie was to the waitstaff, to himself and how she made a nuisance of herself until the limo got there.

Gracie noticed however that he left out a few details. Namely, her drunken behavior and the pranks that she played on him and of course, the fact he saved her from drowning.

“I see. Well, do you have anything to say?”

Diego sighed and said, “I just couldn’t do it, there was no connection there, Mrs. Grayson. I gave her a chance to give me something to latch on to and she ruined it…” she said that last part while looking at Gracie.

“…I couldn’t fall in love with your daughter and I’m sorry…”

Grace looked confused. “Why are you apologizing to me?”

“What…do I apologize to Gracie?”

“No…why are you apologizing at all?”

Both Diego and Gracie were stunned. “I…I mean…wasn’t my job here to fall in love with her?”

She chuckled. “No. I just told you to go on a date with her. What happens afterwards was up to the both of you.”

Gracie cried out, “What!? But, I assumed that he had to…”

“I can’t force him to love you! But I can force you both to get along. NO MORE PRANKS. GOT IT, DIEGO?”

“Got it, ma’am.”

“And that goes double for you, Gracie. Now get to bed, you still have two days of groundskeeping duty. I want that flower bed you destroyed replanted by Sunday or else you’re doing this for much longer!”

As much as Gracie wanted to argue and whine about this, she just responded with a simple, “Yes, ma’am.” and walked out. No crying, no tantrum throwing. Just a simple acknowledgement of defeat.

Grace was rather surprised by this. “Diego…what really happened?”

“What do you mean?”

“You know what I mean.”

“I’m not sure what you’re getting at.”

She sighed and said, “Your pants are different.”

Diego was stunned as she caught that somehow. “Well, ok. So Gracie kind of pranked me but it wasn’t a major one. Then one thing lead to another and well, she got me some new pants due to the old ones getting lost.”

“Was that before or after she almost drowned?”

Diego had his eyes go wide. “H-how did you-?”

“Do you really think I’d have left you both out there, unsupervised?”

Before he could ask who it was, he saw the driver of the Limo walk into the room. “This is one of my security guards. She keeps a eye on Gracie whenever she leaves the mansion grounds. She blends in rather nicely doesn’t she?”

Diego was stunned, he didn’t notice her at all. He was stunned further when a few other women walked in. One was dressed as a waitress. Another was a woman in a fancy dress. And the last one was dressed as a lifeguard?

“Ok, I can guess where the waitress and maybe the fancy dressed woman were in all this, but what about the lifeguard there?”

“I was preparing to rescue Gracie from the ocean, but you got to her first.” she said.

“You’re dismissed, ladies.” said Grace, waving them off.

The guards walked out. “Care to explain why Gracie was in the ocean in the first place?”

“Well, she insisted on ordering wine at the restaurant and-”

“Oh dear! I should’ve warned you, she tends to get a bit…out there when she drinks.”

“I noticed…” he said, matter-of-factly.

“But anyway, she proceed to get all handsy with me and then she ran off and…took a swim in the ocean. I told her not to but she was all the way out there by the time I caught up with her. Had I known any of that would happen, I’d have stopped her from drinking in the first place.”

“It’s alright, I’m just glad she’s safe. You were very brave, dear. Thank you.”

He felt his heart start to beat a little faster as she praised him once more. “So, am I good? Is my punishment over?”

“It is. Enjoy your remaining two days of vacation.”

“Yes, ma’am!”

He did it! He got through that awful date. That’s when he tried something a bit risky.

“So…Mrs. Grayson, I should tell you. Me and Gracie found this lovely Italian place and well, I…uh…I thought the food was fantastic and….”

Diego started to get a bit sheepish as Grace stared at him quizzically. “Yes…I’m sure the place was nice. Would you like some next time I order out for everyone?”

“No! Well, yes actually, it was really great, but I meant more what if we went out to the restaurant.”

“As a group? There’s a lot of employees here. I don’t think everyone will be able to be seated even if I rent out the restaurant for a day.”

“What I mean is…maybe as a group of two….” he started to look down and blush. He was quickly losing his nerve.

That’s when Grace realized what he was trying to say. “OH…hehehehehehehe! Awww…Diego, that’s real sweet….”, she said, looking at him like he was a small puppy.

His eyes lit up, was that a yes!? He had a grin on his face as he was about to ask her what time she would love to go with him, but then she continued. “….but I don’t think I’d be stimulating conversation to you…”

“Nonsense, Grace. You’re very stimulating.” he said with a smile, until he realized the double meaning.

“I MEAN, YOU’D BE INTERESTING. I’d love nothing more then to hear everything about you as we sit together in a dimly lit fancy restaurant and spend time alone together and…stuff.”

“Diego, let me just say something to make myself clear. I don’t think you’d like me like that.”

“Why not? Considering what you and I did in the bedroom a few days back, I assumed that you’d be down to…I mean, it’s ok if you aren’t, I know I’m not worth much but-”

“Diego, we’ve been over this. I don’t see you romantically.”

He had his heart sink. “Oh….”

“But I do think you’re very sexy and would love to do so many things with you.”

“WHAT!? REALLY!?” His heart rose up again.

“You think I’m sexy? I….I….” he started to hyperventilate. But in joy rather than fear.

“Yes…and considering that you did rescue my daughter, I have another…job…that I could offer you.”

“What do I have to do?”

“All you have to do is, whenever I feel that I’m in need of some…stress relief, shall we say, you’d be summoned to my bedroom and we could play around a little. Just you, me….”

She got close to his ear and whispered,”…and that cute little penis of yours.”

He turned red as he felt her warm breath on his neck and felt her trace one of her fingers on his earlobe. “W-what would we do?”

“Anything, I wanted. For example, considering that I gave your adorable little guy some kisses and licks…perhaps maybe you could return the favor.”

“Y-you mean, I’d be licking your…your…” he breathed heavily at the thought.

“Is that a problem?”

“NO! NOT AT ALL! TO EVEN SEE IT, LET ALONE LICK IT WOULD BE A DREAM COME TRUE!”

“I can tell, given how excited you are. You wanna make me scream don’t you?”

“Yes!”

“Make me scream out your name in ecstasy, don’t you?”

“YES!”

“TO GIVE ME EVERY BIT OF PASSION THAT YOU HAVE AND TO BE MY PERSONAL TOY FOREVER AND EVER, RIGHT!?”

“YES, OH GOD, YES!! I WANT IT. I WANT TO BE YOURS AND YOURS ALONE!! I WANT TO BE MR. GRAYSON!!”

Grace stopped for a bit as she almost burst out laughing as he said that. “You’re adorable. You’d never be Mr. Grayson. I’m not looking for another husband at the moment.”

“Wha…? But…I’d be…doesn’t what you’re describing imply that…”

“Diego, what I’m offering is what every man I’ve ever known as dreamed of. A chance to bed me and I’ll even pay you double what you’re being paid now. That’s $1000 per day! You’d be rich and loved until I pass on.”

“But…I…I’d just be your toy?”

“Yup, that’s all. You’d be nothing more than a toy to me. In addition to your groundskeeping duties of course.”

Diego should be jumping for joy right now. He should feel like he won the lottery. He should feel like a king!

…but he wasn’t. Something about this disappointed him. Grace could see the disappointment on his face. “I knew you’d react like that.”

“I- look…I swear it’s nothing against you….I just….”

“Wanted something more romantic out of all this?”

“Yeah…I guess I was hoping to be Mr. Grayson. Someone as beautiful as you was a dream come true. I mean…I’m not saying no…maybe if you want it from time to time I’d be happy to help. But…is that really all we’d be?”

“I’m twice your age dear…romance is out of my reach.”

“What!? No… I’m sure you’d find someone your age. Maybe someone like me…”

“That’s sweet Diego.” she said, smiling warmly at him.

“….but would I ever find someone like you…?”

“I know you will. But for now, maybe find someone your own age. I think you’d make her happy at some point…and she’d make you happy too.”

“Thanks ma’am…”

He was about to walk back to his room and head to bed, but she stopped him once more. “Wait a second, dear.”

She then got up and handed him a piece of paper. “What is it?”

“It’s an invitation to a party I’m holding on Saturday. A Masquerade party. Every single one of the most rich and elite that Small Town has to offer will be there. You’ll be sure to find someone your age there. A few of my friends have daughters, you know….”

“Oh…well, that sounds interesting, I guess.”

“It will be and I’ll make sure Gracie doesn’t bother you. She’s not invited due to her punishment so you shouldn’t be bothered by her.”

“Thanks Grace, I’m sorry about this whole thing with me and her in the first place.”

“It’s quite alright….don’t let it happen again.” she said that last part with a bit of emphasis.

“I won’t ma’am…so let me know if you need…”stress relief.” Heh…”, and with that, he walked off to his room.

As he walked out, she chuckled at his eagerness and then went back to looking over the guest list to said party. Hopefully, Diego will find someone to bond with. On it was a few names, she hoped a certain someone wouldn’t show up, but if he did, Diego would be sure to keep him occupied…and away from Gracie.

Now back in her room, Gracie dressed back into her pajamas. She then threw herself onto the bed. She thought about everything that has transpired. She still couldn’t believe he saved her and almost became friends with her. She then wondered if that whole blackmail thing never happened, would he be with her right now…willingly?

She thought back to all her previous crushes and dates, but none of them really liked her or even wanted to be with her. Diego was the closest thing to a boyfriend she had…and she ruined it.

She wondered, was it really their fault that they didn’t like her, or was Diego right? As she drifted off to sleep, she was back in her kingdom once more. No longer a jester, but still not royalty. That’s when she had an idea…what if she disguised herself to get back into the castle?

It would be a long shot, but she just had to wait for the chance…

Meanwhile, in Diego’s room. He felt somewhat heartbroken. Not just over Grace’s admission that he was eye candy and nothing else, but over Gracie. She was a spoiled rotten, vain, horrid, immature, rich bitch who only cared about herself. She gave him what was the worst night of his life.

…so why was his heart hurting if he felt nothing for her? That brief moment when she was drunk and baring her soul to him. That was the most human he ever saw her. Was there just a sad clown underneath all that makeup and spoiled brat-like nature?

He shook his head. That’s ridiculous. No way. She’d have to turn back time to get him to forgive her, or become a different person entirely. That would never happen. But as he slept, he thought back on him saving her.

Would that lifeguard…guard have made it? He could’ve drowned along with her. Why did he really do that?

Further more, why did he burst into tears when he thought he was too late? Obviously, it’s because he didn’t want to see her die, but…he chuckled. “I wonder if she’ll give me CPR next time? It’s only fair…”

He thought that to himself as he fell asleep, as that vision of her on the beach came back to him. He dreamt of them just laying on the beach, looking up at the stars, holding her hand. He smiled as he dreamed that dream.

A perfect date…

 

The End.

 

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