Diego's Romantic New Job

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?"