Fluttershy, P.I.

That’s what was printed on the frosted window door to Fluttershy’s office, though it was only a step away from not entirely fitting the word.

There was a desk, three chairs with one behind, filing cabinets along one wall and a corkboard along another. The board held a collection of newspaper clippings, notes, and grainy photographs, connected by pins and strings of several colours.

From behind her desk, Fluttershy sat and read the morning newspaper. It was part of her routine, something that helped ground herself in the reality she found herself in. There wasn’t much interesting to read most days, but occasionally Fluttershy would spot something that would pique her interest and point her toward a job. Sometimes the cartoons were funny. Either way, until she opened that door fully for business, the time passed between taking care of personal business and when her actual job started.

She’d stepped into the role she played some time ago. A month and a half, by her counting, but she’d gotten used to it all within the first two weeks. Despite her timid nature, being a private investigator wasn’t too tricky while having its share of ups and downs. She mostly had to talk to people and ask questions, occasionally take photos or sneak into offices and homes to steal a letter. While she despised stealing morally, stealing to make someone else’s life a little better was exhilarating.

Smoke and perfume were permanent scents in the office and streets. Not quite what she expected, but it wasn’t an unwelcome set of smells. The pegasus found it romantic, and she was sure she wasn’t the only one to think that.

With her trench coat folded over the back of her chair and her hat on her desk, she retained a pair of tight pants and an even tighter shirt that left her bra outlined in the fabric. Finding clothes that fit over her head-sized breasts wasn’t too difficult in that version of Fillydelphia, but she discovered that her current wardrobe was growing increasingly tight. She ought to do something about it soon.

A dark brown shape sauntered to the frosted glass and rapped in a quick little pattern. Tap, ta-tap.

“The door’s unlocked,” Fluttershy called out. The confidence in her voice came easy, knowing who it was on the other side of that door, turning the knob, creaking it open.

A light brown mare clad in an ill-fitting, dark brown coat stepped in, a broad, floppy hat hiding most of her face save for her soft, red-brown lips. Once the door shut behind her, Tawny Broad tilted her head back and revealed deep hazel eyes with a smile.

“Good morning.” The depth and richness of Tawny’s voice flowed into Fluttershy’s ears like honey.

Fluttershy folded the newspaper and leaned forward, her breasts sliding onto the desk before her. Even with the support of her bra, it was nice having a little extra help from the tabletop.

“It’s good to see you, Tawny.” Fluttershy’s voice remained soft as butter and sweet as sugar, and she tilted her head with a grin aimed at Tawny.

The two had a decent working relationship. Tawny had her fingers in many pies, an ear to the ground. Whatever saying one would prefer. It meant that she was one of the first people Fluttershy would ask when she needed information. Tawny was almost always able to deliver, even if it was just pointing her in the vaguely correct direction.

She was also about as stacked as Fluttershy was, though the coat partially hid it. Though her hip and bust line was the same, Tawny’s waist was narrower, yet they were close enough in size and shape that they shared a tailor.

She sat in one of the chairs across from Fluttershy and crossed her legs while she reached beneath one of the lapels of her coat. Unlike Fluttershy, who tried buttoning her shirt to her throat to mixed success, Tawny was quite happy to leave a little more skin and fur on show, a rich, brown valley of cleavage that Fluttershy could easily get lost in. The fantasy was broken when Tawny produced a brown envelope and tossed it across the desk at Fluttershy.

Not a social call, then.

Wordlessly, Fluttershy opened the envelope and emptied the contents onto her desk. A small pile of polaroids spilled out, photographs of the marina southwest of Fillydelphia, and a few with hard-to-make-out individuals.

At least one wore a stark, stretched-out white blouse and a wide-brimmed floppy hat on top of her purple mane, her bottom half obscured by a car.

“Thought you would like to know what she was up to,” said Tawny. She reached into the other side of her coat and pulled out a small pack of cigarettes and a lighter. “You don’t mind...?”

Fluttershy did mind, at least on principle, but for some reason, the smoke there smelled nice, nor did it didn’t bring her to cough. So, Fluttershy shook her head and waved a hand forward as permission.

A police transcript had slid out beneath the photos, evidenced by a star and circle, the latter decorated with Fillydelphia Police Department around its edges. Most of it had been blacked out, likely indicating that whatever strings Tawny had pulled still had their limits. Among what could be read, three words repeated. ‘Product.’ ‘Marina.’ ‘Rarity.’

“I suppose I don’t get paid for pointing out she’s up to something.” Fluttershy giggled as she looked back up at Tawny.

“No, but you do get paid for the job.” That time Tawny reached into a pocket and tossed a wad of bills onto the desk between them. “Usual rate, plus a little extra.” She glanced up and down Fluttershy’s front and smirked. “Something tells me you need it.”

The blush crept across Fluttershy’s cheeks, and she reached for the money. Most likely, Tawny hadn’t shorted her, but it was still sensible to flick through and count the bills to ensure the correct amount was there.

“What’s the address?” Fluttershy asked as she prodded one of the photographs of the marina. “I know I could just wander on by, but I’d appreciate it if you could tell me.”

“1024 Magnus Avenue. One of the newer warehouses that’s got an interior dock, I think.”

That made sense for Rarity. She liked her privacy when she wasn’t showing off. Hiding what she was up to meant the two previous grand displays were magnificent and breathtakingly astounding.

But using the docks wasn’t her thing. Very little of value moved in or out there. Trawlers brought fish from downriver, closer to the sea, though most would end up canned and sent back out. Rarity also didn’t have much interest in things like steel refining either. Fillydelphia--any version of Fillydelphia--didn’t have anything worth taking at the marina except perhaps the purses of the few bar owners that way.

“I know what you’re thinking.” Tawny stood and wandered around the desk before sitting on the edge with her legs crossed. “Couldn’t find out much about the traffic. Harbourmaster is locked up tighter than my coat on the edge of town. Don’t know what sailed in or out.”

Fluttershy couldn’t help herself from drinking in Tawny’s figure up close. It was breathtaking, even when concealed by her coat.

Dragging her eyes from Tawny’s chest, Fluttershy cleared her throat and asked, “Is my job to find out what she’s doing at just the marina or what she has planned overall?”

With a shrug, Tawny leaned in, a finger running down the front of Fluttershy’s shirt. It dented the fabric, gently straining the buttons. “We’ll take it step by step. Forgive me for taking advantage of your curiosity and charity, but I know you’ll chase the lead a little further than I can pay right now.” The finger flicked up, catching Fluttershy’s chin. “In cash, at least. Surely you’d be more comfortable out of that thing, no?”

The heat in Fluttershy’s face bridged her nose, and she looked away, back at the photographs. “I need to stay professional,” she said. It was a true enough statement. Fluttershy could probably get away with worse and maintain her reputation easily, but a little less skin went even further.

The offer was mighty tempting, though.

“Hun, you’ve done more than enough professional work for me to get a little TLC in return. We won’t go further than you’re comfortable, and I’m not the sort of girl to go the whole four bases with you, but come on...”

Tawny fingered a button open like she’d practised the motion over and over again, training for the moment. For all Fluttershy knew, she had.

“Let them breathe a little.”

Fluttershy breathed in deeply, her chest heaving up. The one button was enough to let her heavy breasts bulge up, even if just by a tiny bit. It was also paradoxically enough to strain the remaining buttons of her shirt a little more.

Tawny reached down and plucked another button open with a finger, spilling out a little more yellow cleavage before Fluttershy gently pushed the hand away. Yet she lingered rather than throwing her hand back over herself to cover her chest. Even though her breasts ached a little more from the incredibly mild attention they received, it was still a relief to have a little less over them.

Tawny clucked her tongue and leaned back before she took a long drag of her cigarette. “Alright, hun, I get the message.” She retained her smile, but to Fluttershy, it seemed a little less than it was before. Should I assume the job is taken?”

Fluttershy looked straight ahead, Tawny’s body in her peripheral vision, and nodded.

She received a nod in return, followed by Tawny standing and strolling to the front door of Fluttershy’s office. Aside from the hungry look in her eyes, she looked just the same as when she stepped into that room; she looked just the same as when she stepped into Fluttershy’s life.

“I’ll be waiting for news. You know where to find me.”

With that, Tawny left, shutting the door behind her. Though she could only watch Tawny through thick, frosted glass, Fluttershy enjoyed the sway of the earth pony’s hips until they became too blurry to make out.

The breath in Fluttershy’s chest squeaked out in a vocalised sigh as Fluttershy sank into her seat. There she sat, her bosom resting on her belly in her curled-up pose for a minute before she shoved herself out of her chair and stood by the windows.

Fluttershy kept them down and partially open, obscuring wandering eyes but letting her peer out at the traffic below, pedestrian and otherwise. Round-roofed cars and soft-topped convertibles rumbled in the cobbled streets, and foot traffic filled the sidewalks. Though no sound rattled off the windows, there was a drizzle, a light sprinkle that kept the cars and roads shiny and wet.

A minute after Fluttershy stood, she caught a glimpse of Tawny walking through the streets. Her hat obscured her well enough from above, and if Fluttershy weren’t looking out for it specifically, she’d never be able to pick her out of the crowd.

The crowd, though, she could easily pick out individual details.

Dozens of ponies walked the streets. Mid-morning meant a lot of lingering foot traffic, though Fluttershy couldn’t tell what any individual’s job was. They all wore much the same, various soft-brimmed hats and coats that obscured but didn’t hide figures.

When first arriving, Fluttershy thought it was strange how many mares walked the streets at all times of the day. Even back home, there were still many stallions despite the disparity. It didn’t take long for Fluttershy to realise that stallions likely weren’t present in that Fillydelphia. The police force was all mares. So were many of the labourers, the blue-collar workers, the criminals. Every politician, every teacher. Every doctor.

It was nice being surrounded by so much beauty, at least. Fluttershy enjoyed the view of the wet city street, her eyes catching onto a few more... well-endowed figures. Most of the city’s population wasn’t quite as endowed and heavy as Fluttershy, but there was still plenty of mass to go around. In some cases, that mass lay between their legs, too, as bulges significant and small indicated a few of the mares with something else to flaunt.

Fluttershy opened her shirt more, button by button, as she raised her gaze to see the rest of the city. Red and grey bricks dominated much of the skyline, broken by round-topped windows, neon lights, and cables that crisscrossed every street like lace on a bodice.

A big city, seedy on every corner, full of life and adventure that Fluttershy was a little too afraid to leap into.

Now all that kept her from jumping into action was a little more self-care and a plan of action.

Fluttershy discarded her shirt on top of her coat, leaving her bosom bare to bulge over the top of her bra. The cups pinched it just enough to create a delicious divot where black fabric met tit, though it didn’t remain there for long. As Fluttershy approached her office’s door, she unfastened her bra and let it drop where it may, freeing up her hands to turn the lock on the door and bring its blinds down too.

Once Fluttershy got out on the street, she figured she had three critical tasks to accomplish before she moved onto the Doozy. Every job had a Doozy, the part of the job that made her heart race, and her chest ache.

Firstly, she’d need to contact the harbourmaster’s office. Tawny’s description was apt, as the mare in charge of Fillydelphia’s waterways didn’t like to blab too much about day-to-day operations. Someone beneath her, however, would likely have some indication of who and what was going where.

Fluttershy hurried over to the tiny bathroom tucked into the corner of her office. It was small enough that she almost tripped over the toilet, sink, or shower every time she stepped in.

At least it had a mirror that she happily used to examine herself. Right then, it was to check out her breasts, her eyes following the indentation in her breasts left by the bra. She heaved both hands up, relieving some of the sag and weight from one spot in her back to another. Fingers brushed over saucer-sized areola, and with a little squeeze, she produced half a dozen tiny white droplets.

After getting the water-way traffic records, the next step seemed to be worth visiting the marina and talking to employees at some of the surrounding businesses. They likely won’t be able to provide much more information, but there was always something small she could glean from the locals. Sometimes it was what she needed in the moment, plus she could also conduct a distant survey of the warehouse proper just to get an idea of what security might be like.

Leaning over the sink, Fluttershy rested her head on the mirror and squeezed along, running fingers from midway along her rack to the areola. She travelled a little further every few squeezes, making the pink circles bulge a little, and some of the tiny rivulets squirted in response, spraying the white porcelain with milk.

She bit her lip and stifled a moan, burying it in her throat with a gulp.

The bigger of the three tasks, and the last step before the Doozy, was for Fluttershy to speak to a mutual acquaintance of Rarity and hers potentially. It came with the risk of tipping her hand, but at the same time, the acquaintance also came with potential leads. It took some coaxing, but Fluttershy knew how to, ahem, milk the information out of her.

Each jet of milk felt like a tingling pinprick in Fluttershy’s chest, simultaneously uncomfortable and relieving. Draining herself of milk always had a feeling of shame and joy, something she dared only do in private. Tawny knew, though. She must have, or else she wouldn’t have commented on Fluttershy’s inevitable need for an updated wardrobe.

As the milk glistened in the light, hinting at where it ran down and into the drain, Fluttershy pictured the river that ran through Fillydelphia and the canals around the marina.

Once she had all the information she felt she could get there was only one more thing for Fluttershy to do. There was the Doozy.

She had to sneak into the warehouse and look for clues.

The poor pegasus’ breasts wouldn’t drain any time soon. The process was a form of maintenance. Periodic, frustrating, and she even had to repeat it a little more often to ensure she could go for longer periods before milking herself again.

She only needed to empty her udders a little, though. Just a few minutes while she thought about what she needed to do, despite how it twisted her gut and heated her chest and upper thighs. Then she would be small enough the bra wouldn’t pinch, and so long as she kept her flowing, pink mane tied up and tucked under her hat, she could go about the city unnoticed. Just another curvy face in the crowd to be ignored.

Fluttershy slowly straightened herself as she panted, meeting her gaze above her red-hot cheeks. Embarrassment and timidity made her, but she lowered her brow enough to draw out a shiver, putting on a fierce stare. The months alone in the city mean Fluttershy had to rely on herself for support, to push herself along.

A brief splash of water cleaned off the remaining milk collecting on the bottom curve of Fluttershy’s breasts, and another splash helped cool off her cheeks. Fortunately, the little wet patch between her legs was small, and once she was out in the rain it would be painted away by water.

All she had to do after a few moments more of breathing, of waiting, was to redress herself, coat and hat included, and set off into the streets of Fillydelphia.

Author's Note

Thank you for reading so far!

As a reminder, this is a commissioned work. If you would like me to write something for you, please go here!