How to Handle Grown-Ups Too

I had been babysitting my princess for over three months now, every weekend. Everytime I told Filthy Rich that it was a pleasure to look after his daughter, he was delighted to hear it and was allowing me to come over more and more often, just for a few hours. So that he wouldn’t have to leave her home alone at all. My princess put on show of childish disapproval of this in front of her father, but only enough to hide the fact that any time she got to spend with me, she really enjoyed. Or at least I think she did, she enjoyed all the extra pocket money she got out of me at least.

After the very lewd events that happened on that night that I will never forget. When I finally got to put my tongue inside my princess’s tight little fillyhood. She seemed to have been embarrassed with herself to have let it got that far and that we nearly got caught in the act. Since then she had not let me do anything quite so sexual with her. Only getting to lick her hooves and soap her down in the bath if I was lucky.

But I knew my place. I was her toy, her little piggy bank. So I had no right to complain. My princess made me feel happy just by being with her, no matter how badly she treated me, no matter how badly she insulted me and blackmailed me. It was all worth it, just to be able to look at her every weekend.

However, tonight as I walked nervously up to my princess’s house. I had a feeling something was going to be different this time. My heart was still beating faster than it ever had, other then when I was inside her. As Filthy Rich had left me a letter, that both scared and excited me at the prospect of what he might be offering.

I opened the letter again to read it one more time, in case there was a clue as to what I was to expect.

‘Dear Anon, I was wondering if you might be interested in coming over for dinner tonight as I have a proposal, I wish to discuss with you and I think you will be very interested $$$$$$$$’

The dollar signs had been stamped on with green ink. He clearly wanted to emphasise my pay. But of course it wouldn’t be my money it would be hers. But maybe with enough, my princess will let me fuck her again. At that thought my erection tented in my shorts and I had to stop in my tracks right in front of the door.

I couldn’t let Filthy Rich see how horny I was… I quickly adjusted my throbbing and excited erection to try to be less obvious, but I had made the stupid decision to only wear pretty loose fitting shorts. I considered sitting on one of the benches decorating the extravagant garden surrounding the Rich family’s home but, figured it would be a long wait for my boner to settle, if at all.

I knocked on the door to just get it over with and my heart felt like it was going to blast out of my chest. My hands were clammy and I felt so hot that I could feel sweat dripping from my eyebrow.

Rich opened the door nearly instantly. It seemed almost as if he had heard me coming and was already about to open it. This caught me by surprise and had intended to take a deep breath beforehand and realized I hadn’t breathed for nearly a full minute.

“Welcome sir, I am glad you decided to join us!” He exclaimed gleefully as he motioned for me to follow him inside.

“You… you are...“ I started, realizing I was having trouble speaking, while I had no air in my lungs. So before answering any further, I finally took a big gulp of air.

Filthy Rich, simply brushed off how little I responded and probably assumed I was just nervous about the money he offered. He turned around and began walking down the needlessly long lobby toward the dining room. The lobby looked like the kind of front room a hotel would have, rather than just the entrance to a home of one business pony and his daughter.

“You are welcome” I finished awkwardly later after catching my breath.

Upon entering the dining room a full spread of a variety of fancy food was on display, as if he was planning to have a whole dinner party. But I knew better, I knew that this was what he prepared every night, just so that he and my spoiled and demanding princess could be satisfied, no matter what they are in the mood for. He was a very philanthropic pony though and assured me that he doesn’t waste food, he instead just donates whatever is left to ponies in need. Which made be wonder why his daughter turned out so selfish, herself. Speaking of which...

I could she my beautiful princess sitting at the head of the table, looking intently at me while pretending to be a polite, composed filly. It wasn’t long before as soon as Filthy Rich had sat down and turned to look toward me, that my princess gave me that threatening scowl, that I loved so much, that reminded me of my place as her disgusting, perverted, little piggy bank, and that I was lucky she put up with me.

As I sat down I gave her a smile, as innocently as I could, trying to just go through the motions of being a polite dinner guest. She responded a feigned look of interest, also just acting the part of being at dinner. I couldn’t help but stare at the sexy earth filly, a little longer than was probably acceptable, she was so beautiful and difficult to look away from. Her coat was such a pretty shade of pink and her mane was like a mix of lilac and white cotton candy, styled immaculately under the sparkly tiara she always wore as a statement of her entitlement and status above all other ponies and of course a dirty filthy human like myself.

It wasn’t until Filthy Rich started speaking that I snapped out of my trance and turned to look at him.

“You are probably wondering why I have asked you to come here tonight.” He stated and gave me a wink, letting me know, he would not consider it rude for me to get right to business.

“Yeah, uh… some kind of job?” I responded hoping that it would involve my princess in some way, it’s not like Rich, knows me for being good at handling anything else.
“That’s right.” he responded. “You see, as you know, I believe you are the best babysitter I have ever had and it just so happens, that I need to go on quite a long business trip.”

My mouth opened in surprise as thoughts of what this could be, already flooded through my mind. Overnight with my princess? A whole weekend?... Longer?

“And so…” Filthy Rich continued with an almost pleading grin as if he was worried I might be reluctant. “I would like you to live here and look after Diamond Tiara full time… for…” He hesitated a little hoping to read my reaction to the proposal so far.

“H-h-how long?” I stammered.

“Two months.” Filthy eventually managed to blurt out, and as my jaw dropped in astonishment he quickly followed up with what he thought I might find to be the good news. “I will pay you double the normal rate, plus since you are going to be here 24/7, that means you will be getting paid for 24 hours a day” He grinned.

I stared blankly at him for a moment and then turned to my princess and she had an evil looking smirk on her face ready for me. Which she quickly covered with a bored expression, before her dad could see. I absolutely loved every minute I spend with her, but, I would normally get to go home and rest from her cruelty before too long. Now I was going to be under her hoof, for what felt like it would be an eternity. But of course, she owned me, so it had to be up to her.

“Uh… um… Diamond…” I asked her. “Would you be able to tolerate my company for that long?”

She tried her best to look bored and uninterested at the idea, but she snuck me a little bit of that evil little smirk, that showed she was clearly laughing at my expense in her own head.

“I suppose…” She huffed. “If I really have to have a foalsitter, I guess he will do.”

I had her permission, so I turned back to Filthy Rich and nodded my approval for the job.

“Yes sir, I will look after her well sir.” I offered trying to sound monotone and business like. As if the money was the only reason, I was agreeing.

Filthy Rich smiled at me with appreciation. “Thank you very much, but there is one more thing, you need to know, however...”

I cocked my head to the side curious, waiting for what this catch, would be.

“I’m afraid, this opportunity came up very suddenly and I actually need to leave... tonight.” He said frankly.

My eyes opened wide in surprise and I saw my princess barely containing a chuckle.
“In just a few hours I will need you to start.” He clarified. “Is there anything you will need to go and get from home tonight, if you do still want to go ahead with it?”

My mind was racing it was hard to think about anything at all. I noticed that i’d probably need some tighter shorts and more clothes and some of my books and my favourite blanket and pillow. But it was going to be too awkward to stand up right now with how rock hard I was at the moment.

“Ahem!” Diamond made a fake show of clearing her throat and glared at me in the domineering way that she so loves to do, before giving an order, and that was all I needed to know. My orders had been stated, I was sure that, not just am I not allowed to go home to collect anything, I would probably not get to go home at all, until my job was over.

I looked back toward Filthy Rich and shook my head to assure him that I would not need to get anything.

“Well then, that is good news, I’ve got the best foalsitter in all of Equestria taking the job” Filthy celebrated. “Allow me to treat you to some dessert and champagne to celebrate.”

With that Filthy Rich left the table and headed into the kitchen. He clearly felt very happy as he began to whistle while he was in there and this was what finally gave my princess the opportunity to say what she had been dying to, for the whole dinner.

“Ha ha ha” She giggled. “I’m going to have you all to myself for that long.”

She gave me a particularly sinister smile and started to fondle her pretty mane teasingly. “Don’t you think it’s going to be easy for you, you stupid perverted sicko. I am going to be watching you all the time, to make sure you behave.”

“Y-yes princess… I will be good, I promise” I replied under a hushed tone, just to make certain that her dad wouldn’t hear.

She got down from her stool and the tiny filly walked to where I was sitting and inspected me like some livestock that she owned. She pointed her hoof at my extremely obvious boner that was hidden only from being under the table.

“Already thinking your disgusting thoughts, you worthless little piggy bank” She teased in a whisper. “Thinking just because we are going to be alone for a while, I’m going to let you rut me, like a stupid animal in heat, Is that it?”

I looked down at her, even though I was sitting at the table and she was standing next to me, she was only half my height. It looked so adorable that my cock went from being rock hard and swollen to actually hurting and I felt a little jolt of pleasure in it as it reacted to her now being so close, her lavender perfume and her mean glare, showing she was so ready to punish me.

“I’m sorry princess, I am a sick foalophile, I can’t help it.” I admitted.
“You are so lucky I don’t tell my daddy who you really are, that you want to fuck his little daughter as soon as he leaves, you are pathetic!” She emphasised the last word a little louder, showing that she had nothing to lose from us being caught. That I was completely and utterly her control and that the only alternative would be a Canterlot dungeon.

“Please princess, I know, I am all yours and I am so lucky that you keep my secret.” I said in a bit of a whimper. I was pretty sure she was just playing around, to torment me, but there was always at any moment the possibility that she would get bored of me and throw me under the cart.

“Hphm!” She scoffed. “And don’t you forget it!” Then immediately she punched her hoof into my testicles. Causing a searing jolt of pain to shoot through my whole body. But I managed to grit my teeth and not make any more than a quiet little grunt and shed some tears from my eyes. She had hit me there many times before but I had gotten used to containing my complaints, because she would always promise it would be worse if I screamed.

With that she walked back to her stool, while deliberately swaying her tail from side to side to give me a glimpse of her wonderfully pink and tiny little marehood, and it was betraying her true excitement about what was to come, as I noticed some drips of arousal hit the carpet behind her.

Then just as she got back to her seat. Filthy Rich came back with the bottle of champagne. Then somehow, despite it seeming impossible with earth pony hooves, he easily pulled the cork and it popped out, hitting the roof and bouncing around the dining room. He then poured me some in a glass and passed it to me.

Diamond gave her dad a hopeful look and asked sweetly, in a voice that she never ever uses, when we are alone. “Daaaddy, can I please try some?”

Filthy Rich shook his head. “I’m sorry darling, but I still need you to wait until you are older, it’s a drink for adult ponies remember.”

“Awww I know daddy.” She complained as she winked to me. “How much older do I need to be Daddy?”

I knew from that wink, that she was intending to have me help her break a lot of rules during my stay… my service… my captivity.

“Much older still, sweetie.” He laughed and gave me a toast with his glass.

“Here’s to a profitable month for both of us.” He toasted as I rose my glass back to clink with his.

My princess rubbed her hooves together greedily, knowing just how not profitable it was going to be for me.

The rest of the dinner was uneventful and just involved Filthy Rich talking about his business and how he was going to be launching his franchise into regions as far away as The Crystal Empire and that, that was why he was going to be gone for a long time.

But it was now finally time for him to get going and having got a bit carried away talking about himself, he remembered at the last moment, to show me a couple of lists in the kitchen. The first was of Diamond Tiara’s rules, most of which I already knew, but there was more detail and extra ones added that took into account more long term things he had to consider. The second was a schedule of what time Diamond Tiara would need to go to bed, when to eat and as it turned out, she still had a month of holidays from school. It wasn’t starting up again until next month. It really was going to be just me and her, for so long, with no breaks. Then finally he have me a fairly large bag of bits, but assured me, that this was only a tiny fraction of my pay in advance and that, he was going to send the rest of my pay a day at a time to my Ponyville bank account.

I gulped as Filthy Rich, headed out the door with his loaded suitcase, waving goodbye. I just waved half hidden behind the door frame to the kitchen, as my shorts were still pitching a very embarrassing tent and my princess was grinning at it as she waved goodbye to her dad too.

The door shut and this was it. My heart was pounding as I had no idea what would be in store for me next and from the sadistic look in my princess’s eyes, I knew she was eager to get started.