Diego's Hot New Job

As the sun rose in the wee hours of the morning, a young man by the name of Diego was busy driving to his brand new job. Having not gone to college, he didn't have many skills that employers were looking for, so his choices in jobs were rather limited.

Not that the degree would've helped, as he didn't have much job experience and most places wouldn't even let you in the front door without 10 years experience in your chosen field and 3 other jobs to have as a reference.

But he needed some money fast as a new game was coming out and he blew all his money on things like rent and utilities like an actually fiscally responsible person. So while he had enough to scrape by, it left him little time for the finer things and he just wanted a little more.

So he scoured the internet for any and all job offers that sounded decent and/or not entirely sketchy. Most of them were things that were either blatant pyramid schemes or just things that he either would find hellish, didn't pay well or all of the above.

He was just about to give up until he found what could only be described as the holy grail of job opportunities. A job as a groundskeeper at a mansion owned by one of the richest people in town, a beautiful woman that every one only knew as Mrs. Grayson. No one knew what she did to get all that money, or who she was even married to. But the one thing everyone knew about her was that she threw money around like it was confetti!

Practically everyone asked her for cash but she wouldn't just give it out to anyone. She had to be in a good mood or at the very least be there at the right time. But that job listing asked for a very specific type of person, a male (check), in his early 20s (check), of slightly tanned complexion (he wasn't tanned but his skin was just dark enough to look like it, so check) and who wasn't afraid to get dirty.

That last one he wasn't too big of a fan of, nor the fact he had to wake up so early for the job, but for 500 dollars A DAY, he'd crawl through sewage. And all he had to do for this one was cut some grass, tend to some flowers, pull the weeds. Simple stuff, right?

He wasn't sure why his skin tone and age mattered, but whatever. He'd ask questions once he was rolling in the cash he brought home. There was only one stipulation, the first day he had to come in for a sort of interview/test type thing, to make sure he was right for the job.

He replied to the ad and was told to be there the next day. As he drove to her estate, he marveled at the other houses on the way. He swore it was one beautiful mansion after another, each one bigger than the last.

"Must be the rich part of town." he thought to himself.

But then he arrived at a massive gate with a huge letter G on it. He looked at the address on the ad again on his phone, this was the place.

He showed the ad to the guard at the gate as well as his driver's license and other forms of ID and she buzzed him in. He drove further in and saw an opulent mansion with tons of topiary and gardens, one area of which was very unkempt as if no one tended to that in years. That must be the test area, he thought to himself.

After parking car near the front of the house a woman in a suit approached him. "May I park your car sir?"

"Uh, are you a valet?"

"But of course, Mrs Grayson wants all guests that have been approved to be treated with the upmost courtesy and respect."

"Thank you but, I'm actually going to be working here as well, hopefully."

The valet looked surprised, "Really?"

She looked him over carefully and said, "You're the first male worker we've seen in ages. Nevertheless, a guest is a guest, so may I park your car?"

He gave her the keys and sent her on her way. If he wasn't here for the interview, he'd have waited to tip her as she returned.

But as he approached the front door he was greeted by Mrs. Grayson herself. She looked like a celebrity and was dressed like she was about to walk down the red carpet. She wore a sparkly purple backless dress and few bracelets on only one of her wrists.

Her hair was mostly going gray, but she only dyed the top half of her hair a darker black that was obviously fading as the bottom half was almost snow white. This didn't stop her from being one of the most stunning women Diego had ever seen, despite her advanced age.

"Well, are you my new groundskeeper? I must say, you certainly look like you'd be a perfect fit for me."

Diego failed to respond as he was too busy being stunned by the fact that someone in her late-40s looked like she could've been in her mid-20s, aside from her hair color. "Ahem, young man!"

"Oh! Sorry ma'am. Yes I am your new groundskeeper. Or at least, I plan on being yours."

"Excellent, let me show you to your room."

She started leading him through the door. As they entered the foyer, he noticed that there were a lot of maids walking around and cleaning things. Not a single inch of the house had a speck of dirt or dust on it. Even the ceiling was nice and shiny. He then realized what she said earlier.

"Wait, my room?"

"Yes, all staff here have their own room to call their own. They're free to use any of the utilities here and live to their hearts content, within reason of course, as long as they do their job and aren't a nuisance. You'll be no different once you pass the test."

She really did have cash to throw around if she was that generous to give each individual staff member a place to live. As they walked though, he noticed something odd about the staff. They all seemed to be female! From the cleaning staff, to the cooks, to the security guards, to that valet out there, all girls! That's strange, why was he the only male here? Something about this was odd.

"Something troubling you....I'm sorry what was your name again?"

"Diego."

"Right, Diego. Is there something wrong?"

"Uh, I just noticed that you have a lot of maids here....not a single butler or...any other guy."

"Oh that, well I only hire males for groundskeeping work. Though, our last one sadly quit on me."

"Really, why? This place seems great so far."

"Perhaps I was a bit too demanding of him. Hopefully you'll be able to keep up with me. I mean, my demands."

As they continued down a hallway, Diego asked more questions about her.

"So is it just you and your staff who live here?"

"No, my daughter also has a place of residence here, along with Mr. Grayson who is...out at the moment."

Before Diego could ask what she meant by "out" she stopped in front of one of the doors.

"And here we are. I have your uniform in there. You are to change into it and leave those rags you're wearing in the room. Once changed, you are to meet me in the garden. I believe you could see it as you drove up."

"Was it that overgrown patch of land with all the weeds and stuff in it?"

"You catch on pretty quick. You must be very clever."

She smiled and patted his cheek as she was praising him. "Now get ready, I'll be waiting..."

She walked away as he opened the door to his room. It looked like a fancy hotel room. A king sized bed, a massive tv, his own bathroom with a shower and a hot tub right next to it! Goodness, this room alone was nicer than his own house.

He took off his clothes and put on his uniform. It was a set of green overalls, a white shirt, a white hat and a pair of yellow boots. There was a note on them that said "You are to wear only whats provided here, nothing else."

Nothing else? Not even underwear? Cause there were no pants provided here. This made him very uneasy, but for 500 dollars A DAY, he'd probably work naked.

....Ok, maybe not, but he'd try to negotiate for 1k, no, 2k a day if pressed.

As he wore his brand new outfit, he saw that on the back of the note there was a map to the garden. Thank goodness for that, cause this place was so big that he'd probably get lost. He put his normal clothes in one of the drawers in the room and promptly set off for the garden.

After a few turns down several similar looking hallways, he found the doors leading to the garden. As soon as he stepped out, he could see that while the garden looked overgrown from the drive leading to the entrance to the mansion, it was a lot worse up close.

The grass was so long that it actually almost went past Diego's head. Most of the bushes had branches sticking out every where and the flower beds had wilted to the point where the flowers looked like they'd disintegrate if you looked at them wrong.

Mrs, Grayson and a couple of maids were right by the door as he looked over what he had to do. "Oh good, you made it. So I want the grass cut, the bushes pruned, the dead flowers removed and some fresh ones watered and planted."

Diego realized that he may be in over his head here. He barely liked doing any yard work at all and assumed that there would at least be a team to help or that the test would be easier.

"If this is her starting me off small, then what's the full time job going to be like!?" he thought to himself.

"Mrs, Grayson? Do I have to do this all by hand?"

She chuckled and then said, "No of course not, I have a shed full of tools for you to use. It's right over there."

She then pointed to a large wooden shed that looked like it was falling apart. "You may use whatever you need to get the job done. And it must be done by tonight. I'm having a party tonight and I need everything to look neat and tidy. Got it, Diego?"

"Uh, yes ma'am."

"Good, then get to it. I'll come back and check on your progress in a few hours. Good luck."

She then turned to the two maids and whispered to them, "Keep an eye on him and if you see anything interesting about him, tell me immediately."

The two maids nodded their heads and watched their boss walk back in the mansion.

As Diego went to the shed and opened the door he noticed that despite the exterior of the shed looking old and dusty, the inside was not only clean, but filled with tools that looked to have been brand new and never been used. "It's like they were put here just yesterday." he thought to himself.

He wondered what he'd use to cut the grass as while there were electric and gas powered tools available to him, he had never used any of them in his life. He didn't want to accidentally break any of them or cut off a limb by accident so he settled on using a scythe, a pair of hedge clippers and a trowel, for cutting the grass, trimming bushes and planting the flowers respectively.

Before he started, he checked his phone. It was now 10 am. This was going to take a while.

Almost 5 hours later, he was finally almost done. It wasn't easy, but thankfully, those nice maids were there to offer him something to drink or a snack to eat to keep his strength up. That was rather sweet of them, though they drew the line when he asked them to help him. They said they were only there to keep an eye on him and make sure the job was finished and couldn't actually help him do said job.

Hey, it was worth a shot.

As he was working however he noticed them staring at him strangely and occasionally giggle and whisper among themselves. They didn't realize he was going commando, right? Whatever the case, once he was finished he brought it to their attention. They checked his work and concluded that he did an adequate job.

As Diego was about to go back inside to change into his regular clothes, the maids stopped him.

"Uh, so we were kinda wondering if you'd like to join us at the party. I'm sure Mrs. Grayson would love you to be there."

"Really? Does that mean I got the job?"

"We don't know yet, but I'm sure even if you don't, she'd still allow you to come."

"Yeah, she's very generous like that. It seems like she likes you quite a bit, she'd be thrilled to have you there."

Wow, not even a day and it was like he was already one of the elite. Getting invited to a rich person's party.

"Sure, I'll be there."

"Great, but...."

"But what?" asked Diego.

"You can't go dressed like that." said one maid "Or smelling like that." said the other.

He looked down at himself. He was covered in grass clippings, mud, and sweat. Mostly sweat. His white shirt was so soaked in the stuff that it was practically see through. "You go take a shower in your guest room and we'll have someone provide you with your party outfit, ok?"

"Yeah, we'll wash your uniform and even your normal clothes and give them back afterwards."

"That's sweet of you ladies but I'll keep my normal clothes till the party starts..."

He lifted one of his arms to smell himself. "Ugh....But I think I'll still take you up on that shower." The maids giggled and let him back in.

As he walked away they shouted "Remember, the party is at 6pm!"

"Don't be late!"

"I'll try not to be!" He walked back to his room and opened the door.

"God, I smell to high heaven.", He said to himself.

He opened the drawer with his normal clothes in it and placed them on the bed. He then took off his uniform and stood in his room, naked.

As he walked into the bathroom he closed the door and got in the shower. After scrubbing himself down and washing all that awful dirt and grass off of him, He realized that he would have some time to kill, so he decided to try out that hot tub. It looked fancy and had all kinds of dials built onto the side. As he filled it up with water, he got in.

It was the perfect balance of nice and hot but not scalding hot. As he sat in the tub, he felt all his muscle aches and the pain of bending over and doing all that yard-work just leave his body. He turned on the jets, feeling the bubbles all over him. He'd never been naked in a hot tub before and after this, he'd probably find a way to install one in his house.

He did the math, with 500 dollars per day, just for one week alone, he'd have enough to buy a moderately fancy one and a few games including the one he wanted. This was perfect. How could that other groundskeeper quit this job? People would kill for this.

Yup, this was easy money. He looked at the other knobs on the hot tub and found one that just said "massage". He turned it and all of a sudden the jets seemed to target his muscles directly, as if he was getting a full body massage by the water itself.

The relaxing massage coupled with the warmness of the water and the exhaustion he felt, soon made him drift off to sleep. "Just a little nap before the party. What's the harm?"

...

He heard a knocking sound which arose him from his slumber. "Wuh...what time is it?" The clock in the bathroom said 5:15.

"Dang, I must have conked out. I must've been more tired then I thought. Well, time to get ready." He got out from the tub and dried himself off with a towel.

As he was drying himself, he opened the door and was greeted by a woman who gathering up his clothes. He screamed in shock, thankful that he still had the towel covering up his lower area, before scrambling to wrap it around his waist. The woman looked him up and down and started to giggle.

"Well, hello there. You must be that new groundskeeper I've heard so much about."

She then walked towards him and extended her hand out for a handshake. "Uh...I kind of have my hands full at the moment, if you don't mind."

"Hehe, I can see that~"

He had never seen this woman before and she wasn't dressed like a maid or any other staff member here. Yet she had all his clothes balled up in her arms, like she was going to personally wash them herself. Unfortunately, he also noticed that among the filthy uniform, was his street clothes and he didn't see any party outfit for him to wear!

"So, mister groundskeeper, do you have a name?"

"Uh, it's Diego."

"What a cute name for cute guy like yourself."

Diego blushed at this. "Uh...thanks, I guess."

She giggled once more as she very blatantly stared right at the towel he was covering himself with.

"So who are you and why do you have my clothes?"

"Oh, I'm sorry, where are my manners? I'm Gracie. I live here."

"You're Mrs. Grayson's daughter?"

"Yup." she said with a bright cheery smile on her face.

"Really though, Gracie Grayson?"

"That's my name, don't wear it out."

"Well, Gracie, I kind of need those clothes back until I get my party outfit that they promised me."

"Hehe, well I was going to give it to you, but I think you look good enough for the party like that."

Diego's eyes went wide. "Gracie, I'm not going out there in just a towel."

"That's just as well, cause that towel also looks pretty filthy. Let me just take that to be cleaned as well."

He stepped away from her as she approached. "NONO, THAT'S QUITE ALRIGHT. The towel is clean, VERY CLEAN, you don't need to wash it!"

She grabbed a hold of it. "Oh I insist. Besides, I think you'll look even better without it."

Diego held on to that towel like his life depended on it. "LET GO OF IT, PLEASE. CAN'T YOU SEE I'M NAKED!?"

"No you're not, you have a TOWEL!" with that she pulled the towel clean off him.

His hands immediately went to his crotch. "There. Now you're naked."

He crouched down behind the other side of the bed. "Give it back, now!"

She thought about it for a bit and said, "Maybe if you show me what you're hiding I'll let you have it."

He hasn't known Gracie for 10 minutes and he already hates her. "Please Gracie. I don't feel comfortable doing that."

She then sat on a chair facing him. "Well then get comfortable. I have allllll night."

She then giggled and dangled the towel just barely out of arms reach. He'd either have to give in to her demands, or lunge for it. Either way, he'd expose himself.

Taking a deep breath, he then asked. "I do this, I get the towel, yes?"

"You have my word." She said, crossing her fingers behind her back. With a sigh of weary resignation, he moved his hands, giving her a full view of his Groundskeeper's Willy.

He tried to look away from her face as her eyes immediately zeroed in on his package. With an ever increasing blush, he waited for her response to it. Against better judgement, he looked back at her face to find that she brought both her hands to her mouth in an attempt to stifle her laughter.

Her attempt did not last very long.

"Pfffffft, hehehehehehe! I didn't know that poor people had such tiny dicks. Perhaps I could spot you some change. All you seem to have is a roll of dimes on you." With that she wiggled her pinky at him.

"Ooh...and I see that our groundskeeper does some landscaping on the side. Or maybe he just never went through puberty! What an adorable little hairless peepee! Hahahahahaha!"

He stood there with his hands at his side and fidgeted around, trying not to let the comments get to him. She pointed right at it, almost doubling over in laughter as she taunted his little guy.

"It's soooooo tiny and cute. No wonder you were so scared of letting me see it. Hang on, I think I have some tweezers and a magnifying glass around here somewhere."

The humiliation started to get to him and he slammed his hands back down on his shame. "OK, you saw it! Now let me have the towel!"

She brought her hand to her chin as she pretended to be deep in thought. "You mean this towel?"

"Yes!"

"Fine, here you go...."

She brought the towel to him, only to pull it away from him at the last second.

"But you gotta catch me first!"

She then started running for the door.

"GET BACK HERE!"

He started running right for her with one hand on his little one. She then opened the door and was about the throw the towel out the door.

Blinded by the need to have some cover, any cover, Diego charged straight for the door to snatch the towel from her hand. At the very last second, she pulled the towel away, as if she was a matador, even mockingly yelling out "Ole!" as she did so.

This of course resulted in Diego running right out the door and slamming against into the wall in the hallway. Gracie then quickly closed the door behind him and locked it. Diego quickly realized his predicament and started knocking on the door.