Diego’s Hot New Job 1

By username55.

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. Most places wouldn’t even let you in the front door without ten years of experience in your chosen field and three 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 job offers that sounded decent and not entirely sketchy. Most of them were things that were either blatant pyramid schemes or just things that he 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 everyone 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, and 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 his 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 utmost 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 weren’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 a few bracelets on only one of her wrists.

Her hair was mostly 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 room to call their own. They’re free to use any of the utilities here and live to their heart’s 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 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?”


“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 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 what’s 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 of 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 everywhere, 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. 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 into 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 had never been used. ‘It’s like they were put here just yesterday,’ he thought.

He wondered what he’d use to cut the grass 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 the job.

Hey, it was worth a shot.

As he was working, however, he noticed them staring at him strangely and occasionally giggling and whispering among themselves. They didn’t realize he was going commando. 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 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 afterward.”

“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 6 pm!”

“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 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. Diego 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 from 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 than I thought. Well, time to get ready.”

He got out of 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 gathered 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 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 wash them herself personally. Unfortunately, he also noticed that among the filthy uniform were 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 a 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 the party outfit that they promised me.”

“Hehe, well, I was going to give it to you, but I think you look good enough for a 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 take that to be cleaned as well.”

He stepped away from her as she approached. “NO-NO, 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 all night.”

She then giggled and dangled the towel just barely out of arm’s 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, Diego moved his hands, giving her a full view of his Grounds keepers willy. He tried to look away from her face as her eyes immediately zeroed in on his package. With an ever-increasing blush, Diego waited for her response to it. Against better judgment, 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! A little babydick man.”

He stood there with his hands at his side and fidgeted around, trying not to let the comments get to him. Gracie 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?”


“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.


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 were 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 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.

“Who is it?” replied Gracie as Diego tried in vain to open the door.

“You know damn well who it is, LET ME BACK IN, RIGHT NOW!”

“Hehe, sorry. I don’t know anyone by that name.”


“Well, that’s rude. I think I’ll stay here until you ask me again, nicely.”


“Yeah, that’s a good idea. Walk your little butt-naked self all the way to my mom and tell her that her precious angel of a daughter somehow stripped a big, strong groundskeeper naked and locked him out of his room.

I’m sure not only would she believe you, but you walking right to her while a big party is raging, full of all her wealthy socialite friends and her employees, with that little wiggling thing on display will definitely put you in her good graces and not at all make her so angry that she’d kick you out of here. Leaving you to walk back to your house with nothing but a blush.”

This made Diego slowly stop pounding on the door and realize that the party would probably be full of the most elite and powerful people in town. Maybe there is a chance that Mrs. Grayson would believe him, but what would everyone else say? He’d probably embarrass her with his mere presence and be fired on the spot!

“That was sarcasm, by the way. I’m not sure you under—”

“Yes, I got that, thank you,” said Diego, clutching his temple.

He tried a much more friendly tone as he knocked again.

“Eheh, Gracie dear. Darling. Love. We had fun, right? This was a funny prank, but maybe you could let me in now? I promise not to tell your mom, and maybe we could forget all this ever happened.”

“You sure it was funny? I don’t hear you laughing.”

“HAHAHAHA,” he laughed forcefully, “See, I laughed. It was funny. We laughed about it, now, please. Pretty please with sugar on top, let me in. Or at least toss out my clothes.”

“To be honest, I feel like I’m doing you a favor. I mean, these look terrible. Where did you shop for these, Walmart? Your stuff is terrible, too. I mean, do you have an Android phone? What, were you too poor to spring for an iPhone, or were they out of cans-on-a-string?”

He took a deep breath and then, in a pleasant tone of voice that barely hid the extreme anger he felt at this point, said, “First of all, I am not poor. I’m lower middle class.

There’s a bit of overlap nowadays, but I can do pretty well for myself and just chose that phone for its ease of use and ability to repair it without costing an arm and a leg…and second, OPEN THIS DOOR RIGHT NOW!!”

With that, he started banging on the door as hard as he could, at least until he heard something that made him jump. Another door in the hall opened and closed. It was one of the maids. Just as she turned around to see what all the banging was about, he covered himself and ran off. He heard her gasp as she glimpsed his rear end, bouncing down the hall as he ran away, with no idea where even to go.

This mansion was like a labyrinth. Diego had no clue where anything was. All the hallways and doors looked mostly the same, and he was running in sheer panic, turning down several hallways and corridors. Diego looked behind him and saw that the maid wasn’t even chasing him or anything. But now he had no clue where he was. He had no idea where to go to get back to his room, and even if he did, Gracie sure as heck wouldn’t let him in. He hid behind a potted plant and took stock of his situation.

“OK, so a crazy girl just took all my clothes and locked me out of my room in a mansion filled with nothing but women. Not only that, but they’re also in direct contact with your employer, who happens to be one of the richest and most powerful women in town and could fire me before I even got the job or my pay, leaving me with not only nothing to show for this but also if Gracie is right, would send me home with nothing as well.”

He started hyperventilating. “I wonder if the previous groundskeeper went through this as well.”

Before he could ponder further about this, he heard voices coming down the hall. A LOT OF VOICES.

He panicked and tried to lift the plant, but it was too heavy for him to lift. He was in a position where they’d immediately see him if he just stayed put. His only hope was to hide in one of the rooms, but these doors could lead anywhere. It could even lead to the party itself. Thoughts of him running right into the middle of the party with nothing but his hands went through his increasingly panicked mind.

As the voices got closer, he went for it. He tried every door he could, all of them locked. Just as he got to the end of the hall, he prayed that this door would lead somewhere, ANYWHERE, that would keep them from seeing him. It opened! Before he could look inside to check if it was a good hiding spot, he looked back at the source of the voices and saw a few women in sparkly party dresses turn the corner towards him! Lucky for him, they were too engrossed in their conversation to notice the naked man at the end of the hall.

He ran inside and held the door open a crack. He saw them pass by and breathed a sigh of relief at them not noticing him in the hallway. Still, just as he was about to wait for them to walk past so he could run back into the hallway, one of the ladies stopped and looked right at the door he was peeking through. He quickly closed and locked it behind him. As he heard her try the knob repeatedly, he breathed another sigh of relief as he heard her walk away. This is when he noticed what room he was in. It was a beautiful room with a massive swimming pool in it. It looked like something out of the fanciest hotel you’d ever seen. Complete with a hot tub next to it and a steam room off to the side.

He marveled at this beautiful room, regretting not bringing his trunks along for a later swim. However, he probably wouldn’t even be in this mess if he had any clothes at the moment. Wait a minute, there’s a steam room. Where there’s a steam room, there have to be towels! With his hands still shielding himself, he walked towards the door to the steam room, and sure enough, next to it was a towel rack, with some clean ones still on it! Wow, that’s actually pretty lucky. But as he reached for it, he heard voices in the steam room. It was in use, and he could see into the steam-covered window and see five vague shapes coming TOWARD THE DOOR!

He had very little time to react. If only he didn’t get in that stupid hot tub, he’d have seen Gracie coming. Wait, that’s it, THE HOT TUB!

He ran right to the hot tub, and just as the door opened, he jumped in and turned on the bubbles. With the steam from the room obscuring their vision for a bit, they didn’t see him enter the tub. He saw five women in towels exit the steam room. He ducked down to hide his nudity, just barely peaking his head over the surface of the water when one of the women turned to look right at him. He submerged himself under the bubbles, hoping that none of them would see him or get closer.

For a good 30 seconds, he stayed there but was forced back to the surface to get some air. He gasped as he broke the surface. As he regained his breath, he had his eyes shut, praying that none of the women stuck around. He opened his eyes to find no one in front of him. He sighed in relief. But just as he was about to get out to get the towel, he heard something that almost made his heart stop.


He screamed and covered himself, turning around to see who made that sound. It was Mrs Grayson herself, seemingly clad in only a towel. She must have been one of the women in the steam room.

“And just what do you think you’re doing?”

He was so petrified with fear and embarrassment that he couldn’t even speak for a few seconds.

“Well, Diego. I’m waiting. Why are you in my private swimming area?”

This was it. Diego was so fired. He was getting thrown out and humiliated. Maybe she’d be merciful and at least give him his car so he could at least drive home. No. For $500 a day, he had to say something, ANYTHING at least. Maybe he could bluff his way out.

“Oh, uh, hi, Mrs. Grayson. Fancy meeting you here, in your private swimming area. I was just…”

‘Think, Diego, what could you be doing in a hot tub with your hands near your crotch other than that, obviously!’

“I was just testing to see if the temperature was OK for use on humans. You can’t see it due to the bubbles. Still, I actually have a special thermometer that, when held next to the jets, will measure the temperature with such accuracy that it’s the one all professionals use to measure temperature with.”

He sheepishly smiled, hoping that she’d buy that nonsense. She just stared back at him with an unamused expression.

“Uh, but it only works if I sit here with the bubbles turned to max and with both hands on it, so I’ll gladly leave as soon as I’m done, and you can get to doing whatever it is you were going to do.”

As she stared at him a bit more, he grew more panicked.

‘PLEASE LEAVE, PLEASE LEAVE, PLEASE LEAVE, FOR THE LOVE OF GOD, PLEASE LEAVE.’ Maybe if he thought that enough times, he could plant it in her head somehow. No dice.

She then sat down and dipped her feet in the water, and with a bit of a smirk on her face, she asked, “So, can I see this thermometer of yours?”

“NO!” This startled Mrs Grayson and made her look upset.

“UH, I MEAN… No, you can’t, ma’am. See, this thing is top secret and only handed out to be tested by groundskeepers. Because…I’m part of the Groundskeepers Union of America, which is a totally real thing, so there is no need to look it up.

If I showed anyone this thing before it went to market, I could lose my groundskeeper license.”

“You have a license to be a groundskeeper?”

“Sure do, ma’am.”

“Can I see that?”

“Sorry, ma’am, I don’t have it on me at the moment.”

“Why not?”

“Because I’m nake…I MEAN, I left it in my room. I had to disrobe to do this, and I forgot to take it with me. So I forgot to put it in my trunk pocket, which I’m wearing at the moment, of course.”

As he was explaining this, he quickly turned the knob for the bubbles again so that they didn’t dissipate.

“Well, to me, the water seems perfect. Maybe I could join you and your…thermometer in the tub.”

“No, that’s OK, ma’am. In fact, this will take a long time, so if you could leave the room for a bit, I can get this done a lot faster.”

“Oh, I don’t mind waiting. In fact, let me just…”

With that, she stood up slowly, undid her towel, and let it fall to the floor. Diego was in shock. His eyes traced from where the towel was all the way up her body. She was completely and totally…covered in a skimpy two-piece bikini. He was relieved that she wasn’t going to be naked in front of him and, at the same time, a bit disappointed.

“Heh, did you think I was naked under this? Well, truth be told, if you didn’t interrupt me, I’d be skinny dipping in that pool over there. I mean, I would do so anyway, but I’d be too embarrassed to show off in front of the opposite sex.

I couldn’t even imagine the humiliation of showing off my most intimate parts to someone I found extremely attractive. Could you?”

“No, absolutely not. Never crossed my mind in the slightest,” said Diego, leaving out the part where he didn’t need to imagine that humiliation at this point.

Mrs. Grayson then gently lowered herself into the tub with Diego, and upon sitting down, Diego turned the knob for the bubbles once more. “You know, Diego, I kind of want the bubbles off right now.”

“Please keep them on, ma’am. The thermometer needs them to work fully.”

“Show me that thermometer.”

“I can’t ma’am. I’d get in so much trouble. Hell, I’m already in massive trouble just for telling you about it. Could you maybe keep it a secret?”

She giggled slightly, “Don’t worry, Diego, your secret is safe with me. In fact, you can tell me anything. Anything at all.”

She then started to scoot closer to him. “Uh, Mrs Grayson? What are you doing?”

“I just wanted a closer look at my brand new groundskeeper. My brand new, big, strong, and handsome groundskeeper.”

Diego looked uneasy. Was she coming on to him? As she got closer and closer, he turned the bubbles to maximum once more.

She was sitting right next to him now and staring right at him! “Mrs. Grayson, you’re kind of in my personal space bubble.”

“Oh, I haven’t begun to get personal with you yet.”

Diego’s eyes went wide. “Scuse me?”

“Like I said, you can tell me anything. You’re also free to do anything you want. Even me.”

He gulped audibly. Mrs Grayson really was coming on to him! Now most people, Diego included, would absolutely be jumping for joy that a sexy rich woman, who was a textbook example of a MILF, was absolutely horny for him! What kept this from being a dream come true and not the nightmare that it was that she didn’t know he was naked, or at least he assumed that.

Suppose he went for it, or he was found out. In that case, Mrs. Grayson would start asking questions like: “Where is your swimsuit?” or “Did you really just walk through my mansion naked?” or worse, “Is that all you have to offer me?” Due to his self-awareness of his lack of size, he’d be fired for sure. This was his boss, after all! But if he rejected her, well, she had a lot of money behind her. He didn’t know what she’d do, but it would probably be ten times worse than just being kicked out.

He was snapped out of his thoughts by her hand gently caressing his cheek. “You feeling OK, Diego? You’re very hot. In both meanings of the word.” She winked at him with that line. “But seriously, you’re burning up, and your face is as red as a beet. Are you OK?”

Diego managed to squeak out, “Never better.”

She chuckled and said, “Well, that’s good. Now, maybe I can have a little hands-on experience with that thermometer of yours.”

“But I can’t show it to you.”

“I know, but maybe I can just feel it. Run my fingers up and down it a little. What do you say? Can I do it? I want to feel how warm it really is.”

Diego’s mouth was agape. He was breathing heavily as he tried desperately not to say yes. What really didn’t help was that his ‘thermometer’ was getting very excited from this whole thing. With all this teasing, he felt like it was about to pop right here in the tub. But before he could say no, she forced one of his hands off his groin and took a hold of it. He tried not to react as she gently ran her fingers up and down it, even tracing its short length with her nails.

“It feels so stiff and so warm, yet so soft and flesh-like.” She looked at him with a somewhat smug expression on her face as she asked, “Be honest with me, Diego. Is this really a thermometer?”

Despite the faces he was making due to pleasure, as well the fact that there was no way in hell she didn’t already guess that she was feeling up Diego, he doubled down on the lie. It’s really hard to think when you happen to be as hard as a rock and the hard place you’re stuck in.

Trying not to react to her touch, he said, “Y-yes it is. It’s a very sensitive one. I’d…ooh…appreciate it if yoOoOu…don’t mess with it.”

As he was trying and failing to suppress his moans, Mrs. Grayson got closer, and she started stroking his ‘thermometer.’

“Are you sure? Cause it feels like it’s throbbing. Perhaps the tub is getting too hot for this thermometer. Feels like the heat is going to make it burst. Right. In. My. Hand.”

At this point, Diego couldn’t even say anything coherent. He tried to hold back his inevitable orgasm as she just kept going faster and faster. He was gritting his teeth so hard he thought he was going to shatter them.

She then got so close to him that his face practically went into her chest, and she whispered into his ear, “Diego, tell me the truth. Is what I’m feeling your penis?”


“I see…Hehe, You naughty boy.”

As his face was buried in her neck, he could smell her perfume. The smell was intoxicating, though why she wore perfume if she was going into a steam room was a question he’d probably ask once his brain started to register anything resembling logic as he was so focused on the handjob he was currently receiving. He debated internally with himself whether he should tell her to stop or not.

“So…want me to continue?”

“Mmmm… Yes. Oh god, yes.”

Well, that debate didn’t last long, and neither did Diego, as Mrs.Grayson immediately went as fast as she could, milking him right there in the hot tub. With his face still buried in her neck, he shuddered and moaned with his boss’s beautiful hand working him to completion.

“That’s it, let it all out….”

Once he was done, he looked into Mrs. Grayson’s eyes. As soon as he did, he felt her plant a great big kiss right on his lips. He felt like he was melting as she did so.

“Diego, why are you naked in my hot tub?”

At that point, his post-nut clarity kicked in, and Diego fully realized what had just transpired. With a blush returning to his cheeks and his hands returning to his crotch, he tried to explain what happened.

“I…uh….your daughter stole my clothes and locked me out of my room after I was bathing.”

“Are you really saying that she locked you out of your room, naked, and your first thought was to streak all the way here?”


She silenced him by putting a finger to his mouth as if she was shushing him. “It’s OK, Diego. You aren’t in trouble. In fact, I knew this would happen.”

He looked shocked, “How could you have known that I’d have been naked?”

“Well, for one, a thermometer that only works when held with both hands under the water? It’s like you were being a tease.”

“Heh, I guess that was a rather weak excuse…”

“Of course, the biggest giveaway that you were stark naked in that tub was the fact that I had personally asked Gracie to do that.”

He looked shocked at that. “You asked your daughter to strip me?”

“Yup, I wanted you naked and helpless.”

He stammered as she started tracing a finger around his chest.

“Let me ask you something. Did you wonder why the ad specified the age and skin tone of who I wanted to be my groundskeeper?”

“I…uh, well…it did seem weird that you were that specific.”

“Well, let’s just say that…I have a type. Specifically, younger men, who can do menial labor and who know how to please a woman.”

“B-but what about Mr. Grayson?”

“What about him?”

“Won’t he be upset at me for…you know? I don’t want to break up a marriage.”

She chuckled, “I think it’s time you learned something about me…”

She then whispered into his ear. “There is no Mr. Grayson.”

“What? Did he die or something?”

“Nope, he was never real. I legally changed my first name to Missus to stop people from trying to hook up with me.”

And Diego thought that Gracie Grayson was a silly name. “Why would you go through that much trouble?”

“Do you know how many suitors have vied for my attention on a daily basis? When you’re this rich, I’d have men breaking down my door for a chance to have all this.

Though none of them were my type, and even then, they only wanted the money, not me. Changing my first name to Missus really helped cut down on that.

That’s also why I have an exclusively female staff. So none of them fall for me, and even if they were into women, they’d have each other.”

‘There are probably a lot more easier and cheaper solutions than all that,’ Diego thought.

“Besides…that doesn’t mean that there will never be a Mr. Grayson,” she said as she lightly tickled his chin and traced her hand down his chest.

“Tell me, how does Diego Grayson sound to you?”

He started hyperventilating once more as her hand started to trace lower and lower. “Don’t be scared, Diego. Just move those hands and let me take good care of you.”

The jets had long since stopped, but he was still hesitant about showing off his dick, even if she knew what it felt like. With her other hand, she gently took hold of his chin and moved his head so he was staring right into her eyes.

“If you don’t want any of this, just say so. I won’t be mad. This can be a strictly professional relationship. But if you want it to be more, then move those hands.”

A flood of feelings went through his mind. This was an incredibly sexy and rich woman who wanted him. But he would’ve liked to take it slow, plus he wasn’t too sure about the age difference. As she lightly tickled the hands that were covering his dick, he decided that, at this point, he just hoped he could do the job. So he uncovered it, letting her see his dick in all its glory.

“Good boy! So cute and so stiff! Oooh, and you’re so smooth. I love men who shave,” she cooed as Diego felt confident in his body for once.


“Although?” said Diego, wondering what she was going to say.

“It’s a bit…small,” she said as she chuckled slightly.

With that, he slammed his hands back over his genitals and blushed harder than he thought possible. “Oh no, no, no. I feel misunderstood, Diego. Yes, it’s quite small, but here’s the thing…”

She leaned in close to Diego’s ear and whispered, “I adore itty, bitty, babydicks.”

With that, Diego felt something stirring in his loins. It seems that all her teasing caused him to burst once more. With a quiet moan, he let loose, right in his hands.

Mrs. Grayson gasped. “Did you just cum again from me calling it a babydick?”

She pulled his hands away to see his cum floating around under the water and his dick returning to his 1-inch flaccid self. “Oh my god! You did!”

As he blushed once more, he tried defending himself. “I-I swear it was just because all that teasing you did before the bubbles went away finally boiled over!”

“Oh, it’s OK. I’m sure that teeny little weewee needed a break. It looked like the most adorable Vienna Sausage I’ve ever seen. I hope you don’t mind if I give it a nibble next time.”

She then illustrated her point by wiggling her pinky at him before kissing said pinky and playfully putting it in her mouth to suck on. This, of course, had an immediate effect on Diego, which did not go unnoticed.

“Hehehehe, I knew it. My sexy little groundskeeper likes to have sexy women look at him and call him small. Let me call my girlfriends over so they all can get a good look at that twitching little toddler nubby. Maybe I’ll even have you come to the party as you are and entertain the guests. Would you like that?”

He got flustered as he thought of multiple women teasing and cooing over him like Mrs Grayson was doing right now. “I… WHAT… NO, I WOULDN’T… I-I—”

“HA, I’m kidding! Although, given how much it twitched just then, I think you like that idea more than you let on. Tell me, did Gracie see it? What did she think?”

Diego looked away and said, “She said it was the size of a roll of dimes.”

“Awwwww…she’s right. I bet you could fit that thing in a coin roll wrapper. Hahaha! What do the girls say when you whip it out in the bedroom?”

“I…uh…never actually…”

“Speak up, Diego, I didn’t quite catch that.”

“I never actually got that far with any girls…”



He looked defeated as he said that. Not because it was humiliating but because he knew that Mrs. Grayson was right when she said being made fun of turned him on. His roll of dimes was twitching with every giggle, every question, and every second she was staring right at it.

“Awwww…well, I made you squirt your little cummies twice already. But you haven’t seen what I can really do yet. Sit on the side of the tub for me.”

He did as she said, and his cock was at face level.

“I’m going to perform a magic trick for you. I’m going to make your little babydick disappear!”

As he wondered what she meant by that, his eyes went wide as she undid her bikini top right in front of him. She covered her breasts with one hand and threw her top away with the other.

She was quite pale, but her skin was practically flawless. Not a single stretch mark or wrinkle, despite her age. Her breasts were D-cups, which weren’t saggy in the slightest. She saw him staring at them and jiggled them a bit to tease him further. The sight alone almost made him burst once more, but he held it back.

“Ooooh, I can tell from the way you’re leaking that you like what you saw. Don’t burst just yet. I haven’t done my trick.”

She then laid her breasts right on his twitching member. Then she reached into her cleavage and pulled on his cock to make it stand up in between her boobs.

Her touch, combined with her soft, supple tracts of land, sent shivers through his entire body.

“Ta-da. Your dick has disappeared. It’s now lost between my bosoms. It’s so small that I don’t think it will ever find its way out. Poor wittle thing. Poor babydick.”

He bit his lip and desperately tried to hold back his orgasm. “I can feel your heartbeat in between my breasts. It would be best if you were so tense. Let momma Grayson give you a massage. OK, sweetie?”

He nodded his head, and she went to work. The only thing you could hear in that room right at this moment was the sounds of sloshing water, flesh slapping against flesh, and Diego moaning while trying not to blow his load immediately.

“Does that feel good, little guy?”

In between breaths, he said, “It…feels…so…good.”

“Do you want to cum? Do you want to cum for momma?”

“Mmmmmmmm. Yes, please.”

With that, she increased the pace of her titjob, and Diego started screaming out in pleasure!

“OoOoaoH! Mrs. Grayson! I’M CUMMING!”


His response was just a long guttural moan, and to raised his hips in time with her breasts. With that, she felt her cleavage get coated in a sticky white substance. He fell backward as he spilled the last of his seed, panting and trying to catch his breath. Laid out on the pool room floor, he could swear he could see a bright light. Was this heaven? Was he already there that whole time? No, his eyes adjusted to the light, and he saw a woman in a nurse outfit shining a light in his eyes.

“He’s awake!”

He was on the floor of the bathroom where the first hot tub was. Around him was a nurse, Gracie, those two maids from earlier, and Mrs. Grayson. He looked down at himself. His skin was red from head to toe, on his head was a cool, damp washcloth, and his crotch was thankfully covered with a towel. One of the maids offered him an ice-cold bottled water. He downed that thing in an instant. He felt so thirsty.

“What happened?” asked Diego.

“You fell asleep in the hot tub,” said the lady in the nurse uniform.

“Don’t you know that’s not safe? You could’ve overheated and even suffered a heat stroke. Heck, you could’ve drowned if it weren’t for Gracie coming in to check on you.”

One of the maids giggled and said, “She panicked and tried to give him CPR, but when we got there, she was just smooching him.”

Gracie looked angry and said, “SHUT UP! He didn’t need to know that!”

“Hehe, it’s true.”

Diego chuckled slightly as she blushed.

“I just wanted to shut him up and try to get him to leave the hot tub. He kept whispering about my mom for some reason. Eww.”

It dawned on him what happened. He fell asleep in the hot tub, and the heat caused him to dream all that from the moment Gracie walked into Mrs. Grayson, giving him a titjob. It was all a dream. Why are all his dreams filled with him naked in public? That’s probably a question for his therapist.

He tried to get up but was stopped by Mrs. Grayson, “Don’t move. We have to make sure your temperature is back to normal.”

She then was handed a thermometer and put it to his head. It beeped with a reading of 99 degrees. “Oh, thank goodness it’s dropping. I knew I should’ve torn out these hot tubs. That massage setting causes more trouble than it was worth.”

Mrs. Grayson then addressed the other employees and Gracie. “Please leave us alone for a bit. I need to talk with Diego.”

As the girls walked out, Mrs Grayson turned her attention back to him, knelt, and told him, “You’re lucky you left the door unlocked, or else my daughter wouldn’t have been able to find you. You could’ve boiled alive! You’ve lost your hot tub privileges until I can trust you again.”

“I’m so sorry, Mrs. Grayson.”

“Please, call me Grace.”

“Grace? Wait, your legal name isn’t Missus?”

She giggled at that. “You’re adorable, you know that. I don’t know what you were dreaming about, but Gracie told me you kept calling out to me for some reason. What were you dreaming about?”

“Uhhhhhh… I was dreaming about how wonderful and understanding an employer you are?”

“Uh-huh, sure. Is that why I had to replace the towel a couple of times, due to you making a bit of a sticky mess?”

He stared blankly with his face turning slightly redder than the rest of his body as there was no way to answer that and not come off like he didn’t come off in the towel.

“Just try to keep that little thing under control when I’m around. I’m sure that was just an involuntary response. I’ll even give you the day off so you can fully cool off, OK?”

Diego gasped, “Wait, the day off? Does that mean?”

“Yup, welcome home, my new groundskeeper.”

With that, he excitedly stood up, “Oh my goodness, you won’t regret it, ma’am. I won’t let you down and…”

He then noticed that he felt a cool breeze and that Grace’s eyes were just at waist height. She smiled and coyly looked at it with her hand covering her mouth. “Like I said, your babydick is adorable. Hehe.”

As he brought his hands down to cover himself, with a cheesy grin on his face, he asked, “Heh, so, when do I start?”


A few hours later, Diego was fully dressed in his street clothes. His skin had turned back into his usual shade of tan, and he just finished arranging for a few personal items from his house to be brought to the mansion. But after all that excitement, he was ready to call it an early night.

He sadly missed the party, but Grace said there would be many more. She had one every week or so. Since his pajamas weren’t among the items he thought to bring with him, he was just about to sleep in his boxers. But before he could fully disrobe, there was a knock on his door.

He answered it, and it was Grace! He stood there in just his shorts, without a shirt on. Normally, he’d be too shy even to be seen without a shirt, but considering she’s seen him naked at this point, this was nothing.

Though he still had a bit of a blush as she stood in front of him. “Mrs. Grayson, I mean, Grace! Did you need something?”

“I just needed to give you something.” She then walked inside the room, closed the door, and gave him an envelope. “Open it, Diego.”

He did just that and found a check worth 500 dollars. He got paid! This alone would get him the game he wanted. Still, he was so happy that she was kind enough to actually give him a paycheck before he even technically started the job.

But then he looked at the check, and it said: ‘Pay to the order of Diego Grayson.’ His eyes went wide, and he broke out in a cold sweat. As he looked back at Mrs. Grayson, he saw that she had that sexy smirk on her face.

“Something wrong, Diego?”

He started to breathe heavily as he wondered, ‘Was that REALLY a dream?’ “Um, Grace? So, while I was passed out, I had the craziest dream.”

“Was I in it?”

“Y-yes, you were actually, and please forgive me if this sounds too forward, but…you kind of….”

“Yes, Diego? What was I doing to you in this…dream?”

He started blushing and stammering as he tried hard to find a polite way to say that she basically had her way with him in a hot tub.

She chuckled and said, “Was I rubbing you the right way in a hot tub or something? Maybe with my hand or perhaps maybe, two big soft pillows?”

She giggled, making her chest slightly bounce up and down briefly. Diego tried to look away from her as he started hyperventilating once more.

“All I’ll say is this. You tend to talk in your sleep a lot and have quite the naughty imagination.”

He blushed red enough to look like he just got back out of that hot tub as Diego tried to stammer out a response to that, one that didn’t make him sound like he had a wet dream about her! But she then silenced him by putting a finger to his lips, much like she did in his dream, funnily enough.

“I won’t lie. I think you’re quite cute, but if I was just a bit younger. I’d probably have been the one to try and give you CPR rather than my daughter. Though, if you play your cards right, who knows? Maybe we can arrange something. There are other jobs here that only a man can do after all….hehe.”

She then winked at him and then added, “You did seem to get one thing right about me in that fantasy of yours. I do think tiny dicks are just adorable,” and then kissed him on the cheek.

At that moment, you could swear that you could hear a faint scream. That was the sound of Diego screaming internally, so loud that you probably could’ve heard it from his ears.

“Well, you have a good night. See you in the morning, Mr. Grayson.”

With a smile, she wiggled her pinky slightly, kissed it on the tip, and then left the room. Diego collapsed into bed, unsure of what to feel. This sexy, rich woman absolutely lusted over him, and he dreamt that she took advantage of him and made him feel helpless as she and her daughter teased him mercilessly. But on the other hand, somehow, the thought of her and her daughter doing all that to him and getting paid for it was so enticing to him that a small part of him would’ve wanted that for free.

He shook his head. ‘No, that couldn’t be right,’ he thought. ‘Why would I want to be taken advantage of by a hot MILF and her daughter? To have my dick teased for being small and made to cum for their amusement?’ As he pondered this question, he decided to take a brief ice-cold shower and go to bed. Maybe that will finally cool him off as he felt the heat return despite no longer being in that hot tub.

This was definitely going to be an interesting next few days if Diego and his libido would survive that long.


The End.


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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