Office of private affairs

by Huntersquad6

Rating: mature
Tags: My Little Pony: Friendship is Magic, Romance, Sex, Alternate Universe, Original Character
Length: 2722

He's a flirty criminal, Shes a classy tease. Can things work out?

Life in the criminal world is dangerous and lonely, Franky is a stallion who is cocky, smartmouthed mercinary and very flirtatious to the opposite gender. Lisa is a professional mobster with looks, brains, and most of all class. But when she comes to him for help with something personal will he be up to the task?

Artwork was done by https://www.deviantart.com/ravenfox19 take a gander and give some support!

Published 2019-03-20 04:50:01 UTC
Last updated 2019-04-26 05:06:02 UTC

A Request

Manehatten, a city that is busy and full of glamor under Celestias sun. Ponies and other races busily walking though the streets going about their day with ease and bliss. Once when the sun sets and Lunas moon rises though, the cities other lifestyle can be more clearly seen. Crime is sadly a thing that is part of the cities history, many mob and gangster organizations helped fund and build the city in its early years of development and as such they have deep roots into the cities very being. Over time there have been many of backstabbings and uncorruptable officers anf guards who have slowly unraveled the many families that once ran the city and now only one mobster family and small time criminals remain.

Franky Moon happens to be neither of the two. Franky was a earth stallion born from no where important, he stood about a inch or two taller than a average mare, the grey furred stallion had red streaks in his dark mane and tail, he lacked a cutie mark after a bad job some months ago and his two colored eyes, one being purple and the other a lime green. Scars decorated around his legs and body show just the kind of life he has had as a mercinary though many were faded from time, the stallion took refuge in the dockyards of the city after being hospitalized from a job that went wrong by his own doing. After some time to recover the gray stallion began a new life of crime by setting up a smuggling operation in the dockyard..... well more like he offed the head of the opperation and took over but details are a fickle thing.

Said stallion was in his small office reading through cargo manifests, he really had no interest in what the ships and cargo containers were carrying but it was part of his cover as a dockyard manager.

"Excuse me"

A voice inturrupted his thoughts and thankfully his absolute bordem. Looking up from the detestible work papers to with a annoyed grunt only to stare at the mare who had entered his office.

"Lisa what a pleasure" Franky said with a smile.

Lisa was a mare, by heavens she was a mare! Her body was slim yet kept all the right curves in all the right places, her fur was a crimson red as were her eyes and parts of her mane and tail which also had streaks of black and white. She wore a cute business tie almost everywhere she went which defined how much of a perfessional mare she is when on a job for her family, her family being the last major mob family in the city. She had a bit of fluff on her chest but by the lords that only made the white winged mare more attractable to any who looked at her as well as the "Tights" she claimed she wears but to franky they just look like thin leg warmers on her hind legs that go up to her Tea cup cutie mark.

"See something you like lover boy?" she says snapping Franky from his ogling.

Franky cleared his throat and adjusted the fedora he wore, for a stallion who is quite known for his flirting he could never really handle a mare who was as good as him in the art of flirtatious teasing. Franky knew after his first meeting with her, he would court her to the end of time if he had to, a mare who has the looks, brains, deadly skill and teasing ability to match his or more was well worth the risks involved.

"S-Sorry boss, what can your humble servant do to you?" he says regaining his composure

"Dont you mean for me?" She asks with a raised eye brow.

"You know what i said gorgeous" Franky winked and smirked.

Lisa rolled her eyes and shook her head with a small smile.

"Do you have those reports I asked for?" She asked walking up to his desk

"Um.... I think so? Which ones are you refering to?" Franky asked frowning as he tried to think of what she was speaking about.

"The ones for the shipping manifests for the Acheron"

"I..... don't have them" he says slowly.

"You don't?" She asked giving him a nuteral expression.

Franky was now very nervous, Lisa wasnt one to dissapoint by his standards or you might as well jump into the ocean with a lead block tied to your hooves and shark bait on your midsection. She was a mare with expectations and despite of his feelings for her Franky was still cautous and ready with his blade he carried.

"No.. I dont know what you are talking about but i have no such paperwork." He says calmly.

"I see" Lisa hummed and walked around his desk slowly.

Franky watched her with every step she took, he knew he might not be able to beat her but even if he could he probably wouldnt.

"Franky" He tensed as she spoke.

"I... I need your help" She doesnt look at him as one of her wings put a bottle in front of him.

Franky doesnt take his eyes off of her for a minute before he takes the bottle in his hooves and looks at it.

"A birth control potion?" He asks looking at her\ "I dont get it, why would you give me a empty potion for mares?"

If Lisa wasnt naturally red one could see the blush that she now had, she still didnt dare look at the stallion looking at her.

"Do.... you really mean what you say when you flirt with me?" She asked calm but a slight nervousness was in her voice.

Franky was now very confused but from the look in her eye when she glanced at him he could tell she wasnt being playful.

"I... I do" Franky says with a nod.

"Then.... could you help me with something?" She asks now looking at him, she bit on her lower lip as she faced him.

"Anything for you Lisa"

"I... want to give this a try Franky.... you and me" Lisa spoke softly, her eyes looking into his.

"S-so what we gonna set up a date?" Franky asks never losing sight with her fiery eyes.

"No" she responds.

"No? But I though-"

"Most ponies would" She interrupts "And honestly I'm not one to do this.... but you dot seem like the type to just run after getting a mare in bed" she gently kicks a hoof on the ground "And... I trust you.... despite what most say not to"

Franky was silent, he looked this beautiful mare up and down to see if this was a game or a joke, but knowing her it really wasn't. In front of him was the mare of his dreams offering herself to him, no dates, no talking and getting to know one another. Lisa was more deserving than a stallion like him yet here she was.

"Also I've been heat all week and I cannot stand this any more" she mentions hiding her face behind her wings, her cheeks turning pink out of embarrassment.

At this Franky had a little light click in his head and a smirk grew on his muzzle.

"So you want a lay and thought might as well ask me out while you were at it?~" he snickered.

"I can just walk out if you want to be a teasing ass?" She comments and glares at him.

"No!" he shouts and stands up causing her to step back from his unexpected outburst."I-I mean... I accept your offer.... because lords above I would never have the courage to ask you" He spoke softly, closing the gap between them both, his face only inches from her own.

"F-Frank-" before she could utter another word his lips pressed to hers.

Sealing the deal

Frankys face was burning as he had closed the distance between Lisa and himself, his eyes closed tight as his lips held firm against the stunned pegasus mare, her wings pomfed out from the act and her eyes wide with surprise. Soon though she relaxed and pushed herself into the kiss as she let out a content sigh, her eyes closed as they stood there letting months of teasing and flattery out of their systems with each passing second. Franky being the forward stallion as he was took the inititave again by gently wrapping his hooves around Lisas head, giving her mane gentle strokes only to be one upped the equally dominate mare via her ending their kiss by pushing him away and against his desk.

"Gah! The hell Lisa?!"

Franky grunted as he looked at her confused, only for her to slap his right cheek with her hoof with a loud smack.

"That is for just kissing me without propper warning and approval"

She stated with a hard angry glare, only for it to be replaced by her giving him a sultry smirk and wink, her wings ruffling on her sides as she swayed her hips while approaching him. Franky watched her carefully now as he didnt want to be lurerd into another slap but, the mare soon gently ran a hoof over his tie and chest fur.

"Now how about you be a good little worker and hop on that desk hm?~"

Franky gulped as his tail swiftly swiped the cluttered desk behind him clear not blinking once from the shatter of a cup or files flutting to the ground. Lisa let out a giggle as she slowly undid his clip on neck wear, leaning forward and giving his ear a quick nip as she whispered to him.

"Now get on it and lean back stud~"

Fast was no where near close to be called the speed the earth stallion used as he swiftly jumped onto his now cleared workspace his fedora flying off his head as he landed. Lisa quickly followed after him, pouncing onto him if not a bit painfully as she pressed her lips to his own soon to be followed by her tongue invading his ill prepared mouth as she asserted her role as top mare. Franky for his part wasnt having any issues with their roles, he quickly gripped Lisas head as he pressed a counter assault with his tongue which soon tackled against hers and locked in single combat for dominance. They each let out muffled moans as they simply battled it out like this but, as the saying goes "War, War never changes" and it was Franky to begin a new frontier of battle. He moved his hooves down, stroking her neck and mane as they made their way down her back. Lisa still focused on the battle of the tongues would soon let out a gasp as he gave the bse of her wings a light rub and causing her to pull away with a moan as he ran his hooves slowly up the sensative apendages.

"O-oooh~ you aaaaah~ C-cheating ass!~"

She gasped and moaned as Franky chuckled

"Sorry boss but i aim to win and please~"

"W-well then Ah!~ Guess its my turn!"

Lisa said with a bite to Frankys nose, the stallion removing his hooves from her wings as he held them to his now bitten nose.

"Ow you damn Aaaaah!~"

Whatever insult Franky had for her was lost entirely as while he was busy rubbing his nose, Lisa had taken the moment to slide down his body so she may begin her own attack on his body. With her hind legs on the ground Lisa had a excellent vantage point on Frankys midsection and lower region. Franky let out another low groan as the mare flexed her wing across his now hardened and stiff dagger, the seductive smirk she was giving him as she hummed and eyed his weapon and his reactions.

"Hmmm not bad mister Moon~"

"W-well boss, why dont you h-hell yes!"

Franky groaned out as the pegasus mare swiftly popped his other head into her warm hungry mouth, her eyes looking up at him with firery passion as her hooves stroked what didnt already fit. Her tongue licked every part of his member as she pumped her hooves painfully slow causing him to bite his lip and kick his hind legs out whenever she decided to give him a tight suck. Lisa found herself in a comfortable position, she had this stallion in her hooves now and she planned to take advantage of it for all its worth. With a slow push down his member she tormented him as she took ore of him in, only to quickly pull off of it completely with a soft 'pop' sound.

"Hmm not very thick but i think it will do just fine~"

"H-hey its jus-" Franky was silenced by a stern glare and a hoof to his lips.

"If I wasnt in my heat right now id love to play around for longer but-" Her hooves tighten around his member in a vice. "I want this inside me before my steralization potion wears off got that grunt?"

"Y-yes boss..."

He didnt want to admit it but he found this dominate and dangerous part of her to turn him even more on than when she was blowing him. Lisa nodded and climbed up onto him once again, placing her hooves on his shoulders she looked down their bodies as she lined herself up. Once she was satisfied she focused her gaze with his own only for her heart to flutter as he leaned in and kissed her tenderly once again.

"Before we begin.... just know you owe me a dinner date later."

Lisa just stared at him for a few seconds before letting out a giggle.

"Very well that seems like a fair deal."

Despite the need that was burning in her nethers Lisa found this next part to be much harder than she wanted it to be. Franky waited but soon knew hed have to take control for this next part, with a gentle grip of her hips with his hooves he pulled her down carefully until his cocks head pressed just so slightly against her wet and quivering marehood entrance. Lisa gasped as she felt her stallions member gently and oh so annoyingly push inside her tight tunnel, her mind going haywire as the need to just rut with the want to enjoy herself fought one another.

"F-franky... p-please just make this quick~"

Franky being the gentle stallion he was obliged her request by pulling out to his tip only to pull her down impailing her completely to his cocks base, his tips head pressing against her burning cervix as she moaned out in a pleasured shriek. Not wanting to let the stallion do all the work, Lisa took the moment to go wild, her wings extended out as she lifted up and pressed down onto her mates cock. Her mane became disheveled and tangled as she panted and moaned as she for her hopes rocked his world. Franky fought the urge to finish first, he had been on a dry spell for months and this mare was anything but a easy lay, her walls were tight, her body beautiful and by the gods above she was climbing up his list of best sex ever.

"L-Liz gonaaah~"

"A-almost aahhn YES!~"

Both ponies held onto one another as they cried out into one anothers mouths, his hips joined as they reached their climaxes. Frankys mind was blank as a slate as he felt his member flare and fire his seed into the stunning mare on top of him. Their fur was drenched in sweat as they laid back on Frankys desk, their bodies tired and their eyes deadlocked on one anothers.

"S-so...."

"Talk when we wake up Liz."

Franky spoke with a long yawn. Lisa only smiled and nuzzled her face into his neck, soon enough her tired body claimed her mind and they both drifted to sleep.

Author's Note

Sorry for the wait, life can be busy right? Also the fact I lost any inspiration and details for this chapter, my apologies on that if it isn't detailed as id hoped. But I do hope any who reads it will enjoy!