It was a beautiful afternoon in Ponyville. Birds were chirping, the wind was rustling, and a happy din of clopping hooves on flagstones and friendly greetings of the townsfolk filled the warm spring air.

A lone unicorn trotted past the mostly empty town tree-library. There had been rumors circulating that it would be filled by appointment from the royals in Canterlot - but that had been a rumor which persisted for years now, and still, the dim windows were unlit and untended.

The twintail-maned unicorn glanced over at the tree with a capricious sigh. She had actually tried to get a part-time job there as the librarian herself - the pay mentioned in the job posting was absolutely ludicrous, enough to make a young teenager like her drool at the thought of how many bits she’d earn.

Trixie’s application had gone horribly. At least she’d gotten back a reply letter from whatever royal authority managed libraries, laughing at her lack of experience, education, and the audacity that she would even consider herself a potential assistant.

So it was back to the more typical grind for teenage fillies: babysitting.

It was a fairly easy gig, even if most of the town’s foals were pretty young. Trixie made sure to require a hefty surcharge if her babysitting session ended up requiring any diaper changes, and one of the first spells she’d made sure to learn involved completely contactless nappy-replacement.

Otherwise, it usually involved an evening of kicking back on her employer’s couch, opening up a comfortable book, or even tapping away on her magic touchpad and zoning out until the parents came home and rewarded her with a decently-sized sack of bits.

There were lots of new parents in the Ponyville town, and business was good. She’d already saved up about ten percent of the bits she needed to buy that luxurious blue cape and hat that she was convinced would take her burgeoning magic act to the next level.

The cape and hat she really wanted was on the cover of a rare-artifacts periodical that she’d pinned to her bedroom ceiling so she could see it every night before she went to sleep. It was spun with the finest of enchanted purple Saddle Arabian threads emblazoned with stars. The set had recently been designed by one of the archmages of the Royal Canterlot Society, and after a brief period of being on auction for charity, it would either find a buyer at a ridiculously high price, or would go into the archives as yet another high-powered artifact.

Trixie sighed to herself and shook her head, trying to clear it of the impossible dream of owning such a wonderful outfit.

But this was a new household. A new set of parents. And nopony at school had sat for them yet, except for Fertile Flower. And Ferty had only sat for them once, before suddenly leaving town mysteriously. Her family wouldn’t talk about it at all, only saying that Ferty had gone to live with her aunt in Manehattan, and wouldn’t be back for 11 months. None of the ponies she’d spoken to seemed to have any idea why this had happened so suddenly.

The Flower family had also mysteriously become quite wealthy after the event as well, adding on all sorts of new additions to their home. They’d claimed that they’d gotten a small inheritance from a recently deceased family member in Trottingham, which was perplexing because the Flower family had never mentioned having rich relatives before.

In any case, it had opened up a slot to babysit for a new family, and the process had been extremely competitive.

Trixie wasn’t the only teenaged filly looking to fill her saddlebags with bits, and the availability of a new client, particularly one as wealthy as Filthy Rich was suspected to be, caused a lot of mares to jump at the opportunity.

Unlike most other parents, the Riches had actually gone with an interview process, instead of simply taking the first filly who had applied. Stories quickly abounded of the tough grilling that applicants had received when they went in to be questioned. Apparently Mr. Rich was as pleasant as one could possibly be, but his wife was a ferocious interrogator.

Trixie had done her pre-work though, asking her friends what had been asked and what had seemed to disqualify them or upset Mrs. Rich. So she’d gone through the grilling knowing ahead of time how she should answer.

After a smiling introduction and a quick tour of their household by the affable Filthy, he’d excused himself to let his wife step in and begin the intense assault of questions.

Trixie grimaced to herself as she thought back to the barrage, even with her preparation she was still surprised at the first volley, as if she couldn’t believe the stories that her friends had told her were actually true.

...

“How much experience have you had?”

“Oh I’ve babysat for almost two ye-”

“No no no, how much sexual experience have you had?”

“Excuse me?”

…

But she’d quickly shook her head clear, remembering the answers from her friends that had disqualified them, and responding with the opposite answers, even if they were untrue. One of the things she knew was that any refusal to answer a question would instantly end the interview, and dash any hope of landing the lucrative contract from the Rich family.

It wasn’t completely transparent, however. Spoiled Rich was clever enough to sprinkle in plenty of more ‘standard’ questions. Even so, the ‘weird’ questions were easy to pick out, as Mrs. Rich’s ears would prick forward with attention every time she asked one of these special inquiries.

No, she’d never had a coltfriend. True, Trixie had little time for the drooling blockheads her age.

Yes, she had seen ‘naughty’ magazines. True, Trixie was no prude.

No, she’d never done any sexual acts with others. True, though she’d tried often enough to get laid, with spectacularly bad results.

Yes, sometimes she’d imagined what it might be like to kiss a mare. False, Trixie wasn’t a filly-fooler… but this had apparently disqualified a few of her friends.

No, she hadn’t gone through her first heat yet. Also false, Trixie had gone through the agonizing pain of the previous Spring and the annoying insatiable desire that it brought with it.

Yes, she was free from any blood or magic diseases. True, as far as Trixie knew. She had no idea where she could have picked them up.

Yes, she’d tried drugs before, and had an open mind. False, she hated the smell of whinny-weed. She found it kind of strange that Filthy wanted a babysitter likely to indulge around her foal, but that seemed to be what they were seeking from her discussion with friends.

At this, Spoiled had harrumphed and sat back.

Trixie wasn’t sure if she was happy or upset that she’d answered the questions correctly up until this point. The look on her face certainly suggested that she was at least conflicted about how well Trixie had done so far on her interrogation.

At this, Filthy smiled for the first time and leaned forward.

This was totally new ground for Trixie, none of her tipsters had made any note of Filthy actually asking any questions. This was virgin territory.

“So Ms. Lulamoon… can I call you Trixie?” He smiled, his voice warm and supportive, especially when contrasted with that of his wife’s.

Trixie smiled back and nodded. You can call me whatever you like, Mr. Rich. She hadn’t had much opportunity to get to know the stallion, but whenever she had he was always polite, friendly, and amiable. Stories flitted around town of just how much Filthy had done for the community and the local economy…

And he certainly wasn’t hard on a mare’s eyes either.

She had often overheard mares tittering to one another when Filthy would walk through town, never quite catching the full story but knowing that the giggling blushes that always accompanied him meant that he was considered quite the catch by the townsmares.

And now, up close, she could see why.

He had a lovely, chiseled jaw, a beautiful mane, and a rugged, stallion-ly physique.

He was a hunk.

“S-sure!”

“Great, well… Trixie... I just have a couple of questions…. Have you ever… played with yourself?”

Trixie felt the blood rush into her cheeks with a fury. If it were one of those old cartoons, she was sure that Filthy would be able to see steam blasting out of her ears as if her head was a kettle on the boil.

She nodded, resisting the impulse to pull her hoodie up over her head and cover her shame.

“Ah, and when you played with yourself… did you uh…” even Filth seemed to be getting infected by the embarrassment at this point, as he watched her squirming with total shame. A sharp elbow from his frowning wife was the only thing that got him to continue. “...did you ever put anything inside yourself?”

Those steam geysers would now be whistling.

Trixie’s ears flattened back against her head and her hooves actually went up her sides to grip the drawstrings of her hoodie, just barely resisting the impulse to grab her hood and bury herself in it. It was so much more embarrassing to have these kind of personal questions asked by a gorgeous stallion than the grouchy mare sitting across from her.

She didn’t know why she couldn’t just shout, take offense and leave. Something about the way that Spoiled had rattled off the questions with such venom and perfunctory demand offset the kind, bashful, gentle hearted question by Mr. Rich.

That and she didn’t want to lose this opportunity either.

She summed up all of her courage and mumbled the answer.

The true answer.

“Y-yes.”

Author's Note

Oh boy, Trixie is so cute when she's mumbling and bumbling.

She seems like she's really got the hots for Mr. Rich, too... a handsome young new father...

I wonder what the answer is going to be.