Diego's Hot New Job

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 a 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 just be a strictly professional relationship. But if you want it to be more, then just 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, 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...."

...."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. You misunderstand me, Diego. Yes its quite small but here's the thing..."

She leaned in close to Diego's ear and whispered, "...I adore itty, bitty, dicks."

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 small?"

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 girl friends over so they all can get a good look at that twitching little 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..."

"WAIT, YOU'VE NEVER HAD SEX BEFORE TODAY!?"

...."No."

He looked defeated as he said that. Not because it was humiliating, but because he knew that she 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 dick, 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..."

He bit his lip and desperately tried to hold back his orgasm. "I can feel your heartbeat in between my breasts. You must be soooooo 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 were the sounds of sloshing water, flesh slapping against flesh and Diego moaning while trying not to immediately blow his load.

"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 COMING!"

"Come for me, Diego! COME FOR ME, MR.GRAYSON! JUST IMAGINE THIS, EVERYDAY. FOR A JOB WELL DONE, IT'S WORTH MORE THAN MONEY, RIGHT!?"

His response was just a long guttural moan and to raise his hips up in time with her breasts. With that, she felt her cleavage get coated in a sticky white substance.

He fell backwards as he spilled the last of his seed, panting and trying to catch his breath. Laid out onto 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 said 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 tried 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 in to 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 then it was worth."

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

As the girls walked out, Mrs Grayson turned her attention back to him, knelt down 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 Mrs?"

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 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, 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 just 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 to even 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. Grayso- I mean, Grace! Did you need something?"

"I just needed to give you something." She then walked inside the room, closed the door and give 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 but 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 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 to himself, "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.

He 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 he 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 shushed 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 kinda 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 small dicks are just adorable." and then gave him a kiss 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 own ears.

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

With a smile she then wiggled her pinky slightly, gave it a kiss on the tip and then left the room.

He collapsed into bed, unsure what to feel. This sexy rich woman absolutely lusts 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, why would he want to be taken advantage of by a hot MILF and her daughter? To have his tiny dick teased and made to cum for their amusement?

As he pondered this question, he decided to go 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 he and his libido would survive that long.