Diego's Breezy New Job

Her response was a simple pinky wiggle while still filming. As he dropped his pants and stepped out of them he turned to Grace and tried to plead her not to do this. "Ma'am maybe you could start me out small, like maybe no clothes in my room only or maybe just walk around in my boxers or something?"

"Diego, unless you have something to admit to me, you're going to be naked in front of all these people. I know they don't mind nudity so you'll be ok, you won't be in trouble. But the question remains, do you have anything to say?"

He wanted to tell her it was Gracie's idea, but what could he say? Gracie would immediately show her the recording! Would she realize it was fake? He had to power through this, if only to prove to Gracie that she would not beat him down!

"No ma'am."

"Then, proceed."

With that he closed his eyes and with one fell swoop, he yanked down his boxers and stood with his arms outstretched in front of everyone. A silence fell over the room. He heard a few snickers but strangely no laughter. He opened his eyes and saw the other employees stunned, but not willing to say anything. Perhaps cause they knew if they made fun of him, Mrs. Grayson would be upset.

That's when Gracie mockingly wolf-whistled and screamed out "Nice dicklette, Diego!"

Many other employees broke down in laughter at that. Seems they were also thinking the same thing as the instant she said that, they too burst out laughing. Some of them turned to each other and wiggled their pinkies while trying to hide their smiles.

Mrs. Grayson however, immediately shouted out, "ENOUGH!" and the whole room stopped. Even Gracie quieted down. "He is not here to be laughed at, he's here to be praised. He was brave enough to bare himself for us and I will not have you make him feel small and insignificant!"

He could hear most of them choke back their laughter at the phrase "small and insignificant". Not being allowed to cover himself, he instead covered his face, which looked like it was sunburnt at this point.

"Come on, Diego. Keep that chin up. You look great, you know that?"

"Uh....T-thank you?" he said, shaking and trying his hardest not to run away.

"I mean that. Look at that body of yours. So lean, so strong. You'd make any girl swoon."

"Uh, Mrs. Grayson? Are you just trying to make me feel better about being naked or do you mean that?"

She then brought the microphone away from her mouth as she whispered in Diego's ear, "Both."

His heart started to pound as he stood there trying his hardest not to get to his hardest. All signs point to the fact that she thinks he's sexy! But that still did not make him feel any less humiliated about the current situation he's in.

"Ahem, anyway! He will be working like this for the next 24 hours. So don't be alarmed about his appearance. If you see him doing anything unsavory, report it to me immediately, but I don't think he'd do anything untoward to any of you."

She then turned to Diego, with a somewhat menacing glare, she added "At least, he'd better not..."

It was rather strange how she could flip between calm and sweet to threatening and angry in an instant. But he assumed that's why she immediately fired those other workers that Gracie framed for those crimes. Even if he knew he made her swoon, he needed to tread lightly. She was still his boss after all.

"That will be all ladies and gentleman. Does anyone have any questions?"

One maid way in the back raised her hand. "Yes?"

"Are you sure that's a gentlemen? I can't see anything between their legs from here!"

As she and a few others burst out laughing at that, Grace responded with "You! You're on garbage duty for a week!"

After some level of decorum was brought back to the room, Mrs. Grayson allowed them to leave to their rooms. Diego immediately tried to go, but just before he walked away he realized he might have a way to have some level of cover.

He went back to Mrs. Grayson and asked, "Umm, I'm not expected to work like this right? As in to actually perform my groundskeeping duties in the buff? I might get sunburned or get cuts on my foot or something."

"Don't worry about that, someone will be covering for you tomorrow. I have a very special job for you. I'll brief you on it when you wake up. Now get some rest, you're gonna need it. Hehe..."

He walked back to his room, feeling eyes on every inch of his body. Once he got back to his room, he locked the door and went to bed. Tomorrow was gonna suck...

Diego yawned as he woke up. He looked around and saw Miss Grayson and a few others standing there, with angry looks on their faces. "Uh, good morning, Grace."

"That's Mrs. Grayson to you, you horrible pervert."

"Wha-?"

"I know what you did to my poor, innocent daughter! YOU SHOULD BE ASHAMED OF YOURSELF!"

"WAIT, MRS. GRAYSON, YOU GOT IT ALL WRONG! I CAN EXPLA-"

"SECURITY, HE'S AWAKE, TAKE HIM TO THE FRONT OF THE MANSION, NOW!"

Two burly looking women burst into the room, pulled Diego up by his shoulders and yanked him out of bed. Dragging him out the door and taking him to the entrance. He was still naked of course as he was lead by all the staff members, who took the time to jeer at him and call him horrible names. Some of those names weren't even related to his tiny dick.

As they dragged him through the door, they lead him to the front gate, where he saw all his stuff that he brought with him, his game systems, his clothes, his belongings and even his car, being pushed through what looked like an industrial sized shredder.

"WHA- WHAT YOU DOING!?"

"THOSE WHO COMMIT CRIMES OF ANY CALIBER HERE, ARE STRIPPED OF ALL THEIR POSSESSIONS. YOU NO LONGER HAVE ANYTHING. YOUR HOUSE NOW BELONGS TO ME. YOU NO LONGER HAVE ANY RIGHTS. YOU DON'T EVEN HAVE A NAME. YOU'RE NOTHING!"

"MRS. GRAYSON, PLEASE! YOU CAN'T DO THIS!"

"Can't I, boy? I OWN THIS TOWN...and everyone in it. If I want you gone, THEN YOU'RE GONE! TAKE HIM OUT WITH THE REST OF THE TRASH!"

Diego, or rather the person formally known as Diego was thrown into the back of an empty garbage truck. With all the scrapped remains of his stuff soon following him. He was being crushed by all of it. He struggled to breathe as he felt the truck being driven from the mansion. But just as quickly as it drove off, it stopped and dumped its load right in front of the big gate leading into the Grayson Estate.

As he dug himself out of the shrapnel that was once all his stuff, he saw the truck do a U-turn and then start driving toward him. He dodged out of the way as he saw the truck come to a stop as soon as it was on top of all his stuff. The window rolled down and the driver of the truck was revealed to be Gracie!

"What a shame, you could've been someone. You could've been mine. But instead you just had to be a stubborn, poor little boy. Well, farewell, my former little peon!" and she drove back through the gate, with it shutting behind her as he heard her cackling.

"NO! PLEASE, LET ME BACK IN!" he tried to open the gate, but the second he touched it, several alarms started to ring and the police showed up. With their guns drawn, he put his hands up and begged for mercy.

"NO! PLEASE, I SWEAR ITS A LIE, I DIDN'T DO ANYTHING PLEASE! YOU GOTTA BELIEVE ME!!!!!"

A single gunshot rang out. And that's when he woke up with a start. He looked around, he was still in his room. He breathed a sigh of relief. Perhaps all of last night was a dream. He then turned to his side and saw Gracie right next to him, in bed. "Morning, little peon. Hehe."

With a blood-curdling scream, Diego fell off the bed and hid behind his blankets before angrily asking, "WHAT ARE YOU DOING IN MY ROOM!?"

"What? Can't I just check how my favorite little peon is doing today?"

..."Gracie, how long have you been here in my bed with me?"

"That's not important." she said, getting out of bed, revealing that she wore her full dress and heels while she was in bed with him.

"What is important though is that you're gonna miss breakfast if you sleep the day away."

"I don't have to do my job today, THANKS TO YOU, so let me sleep."

He got back into bed and attempted to go back to sleep. Gracie then pulled the covers off of him and then yanked him off the bed by his foot. As he laid sprawled out on the floor of his room, Gracie giggled while looking right between his legs.

He was so humiliated and done with everything yesterday that he forgot to put on his pjs! "Nice morning wood, Diego. Or more accurately, morning twig. Hehe~"

He slammed his hands over his sunrise stiffy. "How did you even get in my room!? I made sure to lock the door."

"I have a master key. Mom gave me a copy of it."

"Why would she give you a key!?"

"Well, to be fair, I might have borrowed it without her knowledge. Now get to breakfast...or else."

"Fine, I'll be there. Just get out please."

"Hehe, see you there. Hope to see your head held high, like you promised. Maybe both heads as you proudly walk down the halls with your tiny little-"

"I GET IT, JUST GO!"

She walked out of his room, giggling. After he took a very brief cold shower to make things a bit softer, he dried off and walked towards the door.

He took a deep breath and gave himself a bit of a pep talk. "Ok, you can do this. Everyone here has seen it already, so the initial shock should've worn off. Besides, Grace thinks you're sexy, so there's that...right?"

Shaking and reaching for the doorknob, Diego turned it and walked out the door, naked as the day he was born. He felt the blood rush to his face as he walked through the halls. Even though no one was around as he made his way to the dining hall, he still felt like his heart was about to pop out of his chest.

He walked there almost like his brain was on auto-pilot, trying not to look at anyone in the eye or panic as everyone got a perfect view of his one-incher and his chubby butt. No matter what he did, no matter how much exercise he did, he always had that accursed ass.

He got his food from the chef, who he swore made a joke about small sausages and big buns under her breath as he walked away and went to sit down. His breakfast of choice? A cheese omelette with pork sausages on the side with an ice cold diet cherry soda to drink.

At least the food was delicious. But he made the mistake of looking around the hall as he ate. He saw a couple of maids giggling. They too had sausages on their plates. One of them clearly looked under the table and wiggled the sausage while giggling. That's when the other one shook her head, took the sausage, broke it so only a little bit was in her hand and then pointed at him and giggled.

It didn't take a genius to figure out what that tiny sausage was being compared to as Diego looked back down at his breakfast and turned bright red. It felt like high school all over again as some of these mean girls made him feel as small as his dick.

Just then, he saw those two maids suddenly get very quiet and go back to eating their food. "Ahem, Diego?"

He looked behind him and saw Mrs. Grayson. "Oh, heh. Good morning ma'am. How're you?" he asked, crossing his legs and trying not to faint from embarrassment.

"Good to see you up so bright and early. I must admit, I didn't think you'd be awake yet."

"Well...I did skip dinner last night. So I got up to eat breakfast, ma'am."

"So about that job, Diego. All you need to do is come to the library at around 3pm."

"What exactly do I need to do?"

"I'll tell you then. Just shower, put on some cologne and look your best. It's say dress well, but, you're already in your nicest outfit." She giggled and winked with that line.

As she walked away, he started to scarf down the rest of his meal and ran back to his room. At least he could wear clothes in his room, he thought to himself. But just as he got there he saw a few of the maids haul away several baskets full of clothes. Baskets full of very familiar clothes.

He went inside his room and sure enough, all his clothes were gone. All his shirts, pants, shorts, underwear, everything. They even took his shoes, the blankets from the bed and the bath towels!

On his bed was a note that read:

Hey, little peon!

I had the maid$ ¢onfi$¢ate all your ¢lothe$. Why? Well, ju$t ¢ause I thought it'd be funny. x3

You won't be needing them anyway. But don't fret, I left $omething to ¢over up what little you have in the top drawer. Not that you're allowed to wear them out$ide but at lea$t it'$ $omething.

Gra¢ie <3

P.$: $ay ¢hee$e!

"Cheese?"

At that moment he heard a click, saw a bright flash of light and Gracie emerged from the bathroom with a polaroid camera. As the picture developed, Gracie was giggling at his stunned expression in said picture. She then showed it to him.

"That teenie weenie is so photogenic, isn't it?"

After shouting a few things way too colorful to repeat here and kicking her out of the room he looked at what she left him. It was a collection of wash cloths and tea towels, as well as a post-it note that read, "Put thi$ on your weewee and I bet it would ¢over it".

Out of curiosity, he held it over his dick and looked in the mirror. He didn't know which was worse, the fact that Gracie thought his dick was so small that post it note would fully cover it, or the fact it turned out she was right.

"She's not gonna beat me! SHE'S NOT GONNA BEAT ME!", he thought angrily to himself as he took in the situation. At this point it wasn't about the money, it wasn't about the blackmail, it wasn't even about impressing Mrs. Grayson. No, at this point, what was keeping Diego from giving up was pure, unadulterated spite.

He crumpled it up and went to take his shower. At the very least, the wash cloths helped him dry off after the shower due to the lack of towels. As he got ready for whatever Mrs. Grayson had planned for him, he wondered what it was. Why did he have to freshen up for it? Was it a date or something?

No...that'd be silly. A date where he was naked and she was clothed. That wouldn't be the case right? His heart quickened imagining her going on a date with him. It wasn't even the thought of him being naked that made him blush there. Well, ok, it was a factor but still. Why would she like him?

Was it just the fact that she's seen him naked twice or was it something else? Maybe she was messing with him like Gracie is. Whatever the case, with his hair combed, him smelling like cheap cologne, a forced smile and a blush on his face, he walked to the library.

It was 3pm on the dot as he got there. Mrs. Grayson was talking to someone inside the room as he approached. She turned to walk out and saw him. "Well, hello there. You're just in time."

"H-hello, Ma'am. What am I here to do? Organize some books or something?"

"No, Diego. I just needed you here for something. Step inside, won't you?"

She opened the door and he walked into the library. Inside was a large room filled with books on various bookshelves. While it wasn't as big as the name implied there still where a lot of books. Along with a lit fire place and a big fancy couch. A big fancy couch that currently had 5 other women sitting on it!

Diego froze as he saw them. They were all women who looked close to Mrs. Grayson's age. Both parties were stunned for a few seconds before they started cheering and cat calling him.

"Woah! Look at him!"

"It's so tiny and adorable!"

"Hey there, cutie-pie!"

"Come here, little guy. We don't bite...hard."

"Speak for yourself." with this one licking her lips as Diego stood there shaking like a leaf, with a deer in the headlights look.

"W-w-wha....M-Mrs...? What is this?"

"Oh this? This is my book club. We get together every week to discuss the latest novels. Usually romance novels, or some trashy smut we find on the internet."

"Or both." said one of the women holding up a Chuck Tingle novel.

"I guess, Grace had a pervy side to her after all.", he thought to himself.

"So what book are we reading today, Ma'am?" he asked, trying to change the subject to anything other than his nudity

"Nothing actually, our book club is supposed to meet up tomorrow. But I thought I'd invite them over to get to know my favorite new employee."

"Personally, I love him already, but you can't judge a book by its cover." said one woman.

"Or rather his lack of cover...Hehe~", said another.

"Well, go on then, take a seat."

He looked around the room and the only unoccupied seat was on the couch, in the midst of the women looking at him like he was a piece of meat. "I...I'll just stand if that's ok with you."

Mrs. Grayson just turned to him with a stare that seemed to see into his very soul and with a smirk, said only two words. "Sit. Down."

"Y-yes ma'am." he said, trembling as he went to do so. His heart was beating a mile a minute as he sat in between two of them. Grace wasn't threatening him or angry with him or anything. As far as he knew Gracie didn't put her up to this either, so why was he even doing this?

He had no idea. All rational thought seemed to be clouded as he sat down, trying his hardest not to panic at the sight of these ladies. He felt one of them start gently tracing the small of his back with her fingers. Should he tell her to stop? What if Mrs Grayson got mad at him for doing so?

The sound of a cell phone ringing snapped him out of these thoughts. It was Mrs. Grayson's. She looked at it and sighed. "Sorry girls, I gotta step out to take care of something real quick."

"Oh thank goodness." Diego thought to himself as he swore he was about to be molested by these women.

"Diego, stay and entertain them while I'm gone. I won't be long."

"WAIT, GRACE DON'T LEAVE-"

Too late, she was gone and out the door. "... me alone."

He was trapped with 5 lascivious women with no one to protect him. He felt like his heart was gonna explode. He felt the women on both sides of him gently squeezing his cheeks with their other hands running down his thigh towards his currently stiffening and very confused penis.

He was absolutely terrified at what they could do to him. So why is he getting excited at the mere thought of that? Just before they reached his little one, he stood up, almost falling over with how fast he stepped away from the couch.

As the ladies chuckled and giggled at his blushing face and frantic breathing.

"Hehe, are we a little shy?"

"With a little thing like that between his legs, I don't blame him."

"Oh shush. I think he's just as adorable as his little cock."

As he stood there, trying to calm himself down, he debated covering himself. Grace didn't tell him not to, but despite her not being here, he didn't dare try.

That's when a few of them had their eyes go wide. They stared right between his legs as they saw that he was standing up, in more ways than one!

"Oooh...it's pointing at me."

"That means he likes us. The feeling is mutual...Hehe~"

"It's still really small."

"Yeah, but its sooooooo cuuuuuute!"

"Bring it here, boy! I want to pet it~"

He was too flustered to do anything but stand that as stiff as a board. In more ways than one. As he stood there, it suddenly got a bit quiet as the ladies stared right at him. Until one of them broke the silence.

"Well?"

"...W-w-well what?"

"Entertain us."

He audibly gulped and asked. "How?"

The ladies all looked at him with a smug smile as one of them answered his question by extending her pinky, taking her thumb and forefinger and rubbing it in an up and down fashion.

Diego immediately understood what she meant, but tried to feign ignorance. Maybe they'll back off if they think he doesn't know what they mean. "I-I mean...if that's what entertains you I guess..."