Earning Freedom

by Daxisle


Demons and Double Dates

Demons and Double Dates

Smiling with a new sense of Pride, Sin trotted happily through the streets of Canterlot back to the palace to rendezvous with Macintosh. Feeling rather pleased with Fancy Pants' acceptance of his proposal, after a few rounds of testing, of course. However, the Everfree Black Wood did interest him and would interest the masses. Sin hadn't done too much research into the market for prices and what not, but that would only have improved his already considerable demonstration. Good thin Fancy wasn't one of those business types who demanded every nook and cranny be explained.

"Hey Sin." Mac greeted nervously. His eyes were wondering about as if looking for someone about to pounce on him. Guess that meant he got the permit.

"Ready to go?" Sin asked, he had to get back to his house as soon as possible and write up an actual business plan ASAP. Celestial's chairman said he'd be by in a week and between the lumber mill and City Council, he'd have no time to get his work done during said week.

Mac was of a different mind, though. "Weren't ya gonna go git Uppity?" Sin tiled his head before the previous night's conversation came back to him.

"Oh, wait you wanted to do that today?" Mac nodded. "Then why isn't Anna here with you?" The Federalist smirked. How was there supposed to be a "double date" if one party's date wasn't present? His smirk faded when Mac gave a rather believable explanation for the blond earth pony's absence.

"Since Soarin was arrested a few days ago, Annabelle's been trin'a comfort her pa this mornin'. Poor guy's been a wreck." Ah, okay then.

Figuring the date was going to take place in Ponyville, and he'd agreed to it in a guilt by association kind of way, Sin trotted back into the palace. It did astound him just how lax security was when it came to him. His hatred of government wasn't a secret, yet the guards just let him waltz on by. Did they honestly consider him to not be a threat?

'Oh but of course, I mean with your track record of terrorism, they should be swarming you at every turn, shouldn't they?'

Sin pressed his lips. Hey, he may not be a terrorist, but he had broken multiple laws.
'Yep, and like a good dog you continually come back to lick Celestia's horse shoes for forgiveness and take any punishment she dishes out.'

Ouch.

Making way to the castle proper, the duo asked the day time receptionist about the mare in question and about her current whereabouts. To Mac's disappointment, and Sin's delight, Uppity was under a "Do not disturb" order and refused to give her where abouts.

"I am sorry." The mare said dryly, almost bored. "But those are the rules."

"Well darn. Guess I'll have to take a raincheck on that double date thing, Mac." Sin complained half heartedly. To this, the receptionist's eyes widened with new found interest.

"Wait, date? As in... romantic involvement?" It was at that moment of heart stopping terror that the Federalist knew he'd fucked up. The unicorn mare's eyes were alight with joy now. "Well why didn't you say so?! She's on level four in the east wing! Oh boy, I've gotta tell the girls about this!"

Sin pressed his lips together as the giddy mare practically squeeled with foalish delight.

'You fucked up.'

I'm aware.

Thanking her for her help, Mac lead a much more begrudging Sin to the mentioned place and smiled smuggly. He'd seen the discomfort Sin was going through, and took a sick kind of relishing in it. "C'mon, don't look so glum. This'll be good fer you." He said, trying to offer comfort.

The oaken stallion merely grumbled in reply, deeply regretting his decisions to this whole venture. It wasn't just the social graces of dating at this point either, but the realization of what he was now responsible for. Sin's time and attention was already streached thin, what with his job at the lumber mill, his dealings with the City Council, and his dealings with the black market. On top of that, now, he was also responsible for putting together a full business plan that would lead to the promised research facility/lumbermill, all for the sake of covering his own ass over the consequential loss of jobs his tax slashing would bring.

Uncomfortable, tired, and thoroughly distracted, his mind was on overdrive to dig up all that he knew about small business building. Permits, pay, materials, govt inquiry; there was so much to take into consideration and he had no excess capital to delegate the process to another company.

His mind thoroughly occupied by the realization he may have bitten off more than he could chew, Sin didn't even notice when Mac told some guard outside of a huge wooden door whom they were here to see.


Mac quirked a brow to the very odd pair of ponies sitting across from him as they quietly sat upon the train bound for Ponyville.

The orange pegasus with a shoulder length mane of well kept lavender sat humming to herself, her purple eyes full of happiness and giddiness like a foal on Hearth's Warming morn. Besides her, a typically stoic and irritable stallion sat with a notepad and pen, a note pad that was now being devastated by the stallion's vicious scribbling, reading and tearing away each failed attempt with a frustrated grunt.

It was odd, seeing the contrast between the two. One being so happy and excited with herself while the other was irritated and immersed in anywhere but the individual besides them. Which was made even more strange by the incredibly intimidating persona Uppity had when they'd arrived to see her.

She was in the middle of a conversation with some green stallion over a matter of public defamation and how to deal with the mare’s responsible. Her attitude reminded Mac alot of Sin's, actually. Cold, logical and ruthless. Much more confident and direct than she was during Sin's trial.
Mac couldn't help but smile, knowing exactly where she picked up the habit.

"So, what are we doing? Movie? Dinner?" Uppity asked excitedly.

A growlingly awkward silence passed as Mac looked to Sin to answer her question, though none came. He cleared his throat to gain the pony's attention, and again louder when the first failed.
"Don't look at me." Sin replied, making another literary attempted. "This was your idea... no, that wont work either." He ripped out another piece of paper and added it to a growing pile on the chair beside him.

Furrowing his bro, Macintosh explained that they'd be meeting up with Annabelle and going out to eat. Uppity's excitement compounded ten fold as her suspicions were affirmed. This both warmed Mac and made him feel a little bit of pity, if he didn't know any better, he'd think the DA had never had a night out with friends before. By the way she was acting, one would think so. Heck, she didn't even mind that Sin was paying no attention to her, and it was his invitation, begrudged though it may be, that melted her hard exterior and sent her into the excited filly state.

So, he was actually not only doing something good for Sin but for her as well.
'You're way to nice of a guy. So underappreciated sometimes.'

The train finally went into the station and the ponies all departed, Sin finally settling on something he could work with in terms of his writing. Mac was curious as to what he was working on, but decided to ask at a later time. He lead the distracted duo out of the station and back to the farm. As expected, Annabelle was back at the house, speaking with Granny and his sister about some such.

"Annabelle!" Uppity decried with a little too much enthusiasm.

"Oh, hi Uppity!" The earth pony greeted, the two shared an awkward hug and began talking about their days.

Mac took the opportunity to see gauge Sin's reaction to the ordeal, but the Federalist was much to immersed in his note pad to pay attention to what was going on around him. Having enough of his obliviousness, the red stallion yanked the small stack of white paper out of Sin's hooves. "Hey, I was reading that."

Mac sighed. "Look, we went all the way to Canterlot ta git Uppity fer a date. It's rude to ignore her." He felt Sin's eyes narrow beneath his goggles, but stood his ground on the matter. There was an agreement made here, and Macintosh planned to hold his friend to it.

Taking note of the present company, Sin leaned in and tried to explain that there was some very important matters that required his attention, but Mac wasn't having it. Whatever the Federalist had planned could wait, today his attention was needed for his friends and Mac would do his damndest to ensure Sin paid every ounce he was due.


"... and so I backed him into a corner. He either exposed his lie or came clean about it!" Uppity recounted with smug satisfaction as she finally concluded on of her most crowning achievements. The four of them had chosen the cafe Sin and Uppity had patronized a few days ago. Mac wasn't much of a coffee drinker, but Annabelle loved the stuff, so did the others, so he'd tolerate it for the sake of spending time together.

Currently it was story time, a topic started off with a tale of her foal hood in which she'd first met the circus dragon, and that she was so terrified she wet herself. Mac, thinking it would all be embarrassing stories, had recounted the "Mr. Smarty Pants" episode that had taken place a little while ago, and was still a little embarrassed of. But he had the last laugh though, the doll still sat on his shelf after all.
Uppity, for her part, settled for a high profile court case she'd taken when she was a little younger. Some city scum who thought he was going to sell some Ganja to minors and make a few quick bits doing it. Idiot landed himself three years for his crimes, plus restitution to the families to help rehabilitate the foals he's sold to.

"Ahh, good times." Uppity said with a stupid smile as she reminisced. "Anyways, you're turn, Sin."

All three pairs of eyes fell upon the distracted brown pegasus as the looked down in contemplation, he was mumbling something under his breath but Mac couldn't make out what he was saying.
"Sin?"

"Huh?"

"It's yer turn fer a story."

"Story?" The Federalist quirked a brow. He looked at the others and realized that they wanted something from him and cursed his lack of attentiveness to the situation. "Umm, what kinda story are we talking about here?"

"Any will do, this is just about us getting to know eachother." Annabelle replied gently, taking a sip of her cup.

Sin pressed his lips and looked around the table as he racked his brain for anything suitable for the situation. Odd thing about him was that he never much cared to remember irrelevant details about his life. Comical moments and anything appropriate for this kind of setting would fall directly under the 'no point in remembering that' category. It wasn't that he forgot those kinds of things intentionally, but if it didn't serve his interests in remembering them, than there was no point in remembering them.

"Umm... I got nothin'." He stated, much to the entire table's annoyance. Hey, it wasn't his fault he'd rather forget stupid moments of his life rather than remember them for social events he never thought he'd be mentally ill enough to take part in.

"Where's your cloak?" Uppity asked, finally speaking out about the missing item. Mac breathed a sigh of relief, hoping to get an answer to the question he'd been meaning to ask for a while now. His relief was quickly joined by interest as Sin's turned his head away, muttering how he didn't wanna talk about it.
Sin, one of the most blunt and ruthless ponies Mac knew of not wanting talk about something?

Now he had to know.

"C'mon Sin!" Uppity said, placing an encouraging hoof on his shoulder.
"Everypony else is telling stories about themselves. Don't worry, we'll still think your the cool and anti social stallion you always are, even if you don't have a past completely made up of revolution and gay hate."

"I told you, I don't hate gays. I'm just indifferent to them." The Federalist shot back.

That caught both Mac and Anna's interest. "What's there to hate about gays?"

Sin deadpanned. There were two choices to make here, well more than that but if he wanted to remain polite, than there were two, even if walking out of this entire situation appealed to his common sense. First he could explain the debate with Uppity, resulting in all three of them most likely ganging up on him. Not fun. Or Second, he could explain about Rainbow Dash ripping apart his cloak in a bid to detract.

Neither decision he cared for, but the latter could at least be explained unimpeded.

"You can thank Rainbow Dash for the missing cloak." He grumbled, taking a sip of his coffee. This piqued curiosity, the gay comment all but forgotten and the other coaxing Sin for details, which he reluctantly gave. "She wanted me to learn to fly, er something. I said no, she said yes... I felt violated."

A few seconds passed in silence and the others burst out in laughter. The Federalist felt his cheeks take a crimson hue, but also chucked under his breath at the joke.

It took a few moments for the others to finally settle down, but eventually they calmed down. "Oh boy, that was perfect!" Annabelle wipped a tear from her eye between gasps. Mac had to agree, dark and dead pan humor wasn't something he typically cared for but the blunt delivery from Sin, of all ponies, was just too much for him not to appreciate. And considering his experience with the matter, him finding comedy with it was saying something.

Uppity who had to bite her lips together to stop the giggle fit also seemed to relax and the group enjoyed the less tense atmosphere. Sin still seemed somewhat preoccupied with his thoughts, but he was engaged in the conversation a little less begrudgingly now. The four friends continued to chat and talk about past experiences as the day went on. Slowly, Mac and Annabelle moved closer and closer together until they were finally side by side, leaning on eachother, stealing gentle muzzles and softer affections when they felt they could get away with it.

“Aww, you two are such a cute couple.” Uppity swooned, “don't you think, Sin?”
The mentioned gave the unicorn a side long glance before taking in the couple before him. “I… guess.”
Again, romance wasn’t really one of his strong suites. No politics, no economics, no real long term consequences that added up to the greater whole of the world. Frankly, romance want any of his business to have an opinion on.

Sighing to herself, Uppity forced the dejection away and asked how the two earth ponies met…


Twilight sparkle sat panting beside an increasingly irate Celestia. This was their seventeenth spell in attempt to exercise the Tantibus. And with another growl of frustration from Celestia after she used her magic to inspect her sister’s mind, it appeared to be another failure.

“DAMMIT!” The solar goddess spat. Twilight's eyes widdened as her back went stiff, she'd never heard her mentor curse before.

“Princess, maybe we should take a break.” The unicorn suggested, just as much for the Alicorn’s sake as much as her own. The two of them had been at this for hours and still no sign of improvement. “give me some time to round up the elements and I will-“

"No, Twilight.” Celestia called her off, calmly but in a way that left no room for argument. “I have stood by twice and relied on you and your friends to fix my mistakes. I will not do so again.”

Luna groaned from her place on the couch. It was the only thing she'd done since the attempted exorcism began. It was a pathetic and helpless whimper that barely registered to normal pony ears. But the pained look on Celestial’s face said that it might as well have been a blood curdling scream. The elder sister had yet to tell her student the circumstances that lead to Luna’s current state, not for lack of the latter's inquiry, though.

“Sister.” Luna called. Perking up, Celestia shuffled and kneeled down to her sister, gently stroking her dull mane with a hoof, “please, forgive my foolishness.”

“Hush, little sister.” The alabaster goddess gently tutted, “we'll find a way to help you. How are you feeling?”

The younger sibling merely wimpered in reply. Celestial’s gaze wonders back to Twilight. Here eyes full of helpless pleading. The librarian shook with frustration, she had no answers to her mentors plight. Luna was the only authority on dream magic, and only she would know how to help the situation.

Many of the lunar servants had been consulted prior to her confession to Celestia. Dreamscape mages, sleep doctors, dreamhealers, none of them had any luck.

Celestia was the last bastion of help to be had barring the Elements of Harmony, and she was slowly growing discouraged with each passing failure.

“Celestia…” she said blankly. “tell me something, sister.”

“Shhh, it's okay Luna.” The white pony replied, lifting her hoof to stroke again, though her affection was intercepted be a dark blue hoof. “Luna?” Twilight felt a jolt of pure ice shoot threw her spine, that voice, she'd heard it before, but it wasn't Luna.

“Tell me, how does it feel?” Luna asked, her head slowly moving up to mere inches from her kin.

That's when it hit her in a rushing brick wall of realization. “Celestia, get away from her!” The Alicorn tried to pull back, but a pair of turquoise eyes mere inches from her face stopped here with a gasp. Eyes much lighter than they should have been and, more importantly, pupils not round like a normal pony but serpentine, like a drake.

“Tell me, how does it feel? Knowing your own sister couldn't trust you enough to seek your aid upon my return?”


Sitting across from one another, Sin and Uppity caught the last train back to Canterlot. The date had gone well enough. After coffee, the troop simply wondered around town for a bit until they spent some time at the park.

Mac and Anna were happy enough with themselves, and Uppity was dropping hints like crazy for him to embrace the affectionate atmosphere. And as he sat in his chair, thinking over the events, small thoughts of intimacy played through the young pony’s mind. He didn't want to say it, but he'd observed the earth ponies’ affection with a small sense of longing.

Knowing that the orange and purple unicorn with the wanted the same of him only served to compound the new feelings. He tried to push the thoughts out of his mind, going over his excuses again and again, but unlike the other times, his desires to… feel didn't subside fid his sense of duty.

No, his feelings were rebelling against his logical mind once again, asserting themselves at the most inconvenient of times.

I won't have time for her, it's not fair to strong her along like that.
‘than you should make time!’ his inner critic chided. ‘it's obvious you care about her, and if you don't act soon, you might miss your chance.’

My chance to what? Tell her that I don't have time? That I'm busy, or that I'm not interested because I want my alone time? How's that fair to her, exactly?

'maybe she'll be understanding that you need your alone time?'

You don't seem to understand mare's-

‘What, and you do? Give me a break, dude.’ The voice sighed. ‘look, you know what you need to do and the choices you need to make. Decide and act, take a chance and live a little!’

“Sin?” he looked to find Uppity with her eyes closed and a content smile. “I just wanted to say thank you for bringing me with you today. I had a lot of fun.”

'cliché as all get out, but still sweet.’

Sweet? Tapio help me, my thoughts are turning fruity

“Yea, umm. Glad you could come.” He replied, sounding much more unsure of himself than he meant to. Still, Uppity’s smiling face didn't falter, her subtle beauty at the moment warming the stallion's chest.

Unable to stand the forces pushing him, Sin finally broke and planned out what he was going to say.

“Uppity…”

She opened her eyes again and tilted her head. “yes?”

“I want to umm…” he paused to clear the lump in his throat, the solid script he'd mentally written suddenly disappearing, courtesy of his reading emotions. “fuck.”

A gasp from the unicorn drew his attention, her orange cheeks turning bright red.

‘Pft hahahaha, oh wow, that was smooth dude, 10 points.’ It took a second, but the Federalist realized the weird that came out of his mouth and he took began to blush.

“No, wait. No, that’s not what I meant to say.” He stammered.
He took a breath and decided to let the truth come out, chips falling where the may.
“Look, I know there's been some… chemistry between us, and I'd like to think you feel the same.”

Nodding, Uppity looked with eager interest. “yes, I've had a little crush on you for a while now.”

“And I have…” he stopped again to clear his throat. “ahem, feeling for you as well.”

The reaction given was far less than what Sin was expecting. Instead of jumping for joy or talking him, Uppity took the confession with grace and dignity. “I'm very glad to hear you say that, too be honest, I was beginning to think you didn't find me attractive.”

“I find you attractive, in most every sense actually.” This emotional honesty thing was working out pretty well, maybe this wasn’t going to be as bad as he thought.

“Then why do you continue to shut me out, Sin?” she opened her eyes and peered into his.

“Fear.” He replied, surprising both Uppity and himself with the response. “Fear, being jaded, having to much on my plate and not enough time, liking my alone time and feeling it would be unfair for you to want more time and attention than I'm willing to give. Take your pick.”

The words came and flowed so naturally, each and every one of them as truthful as the last. It was all out in the open now. No more denial, no more games, the ball was in Uppity’s court now, and Sin would accept what ever she said next.

She didn't sassy anything for quite some time. Sin began to wonder if he made a mistake breaching the subject at all.

Finally, she let out a content sigh and smiled warmly. “thank you for finally being honest with me.” She did before standing from her place and marching forward. The oaken stallion barely had time to react before the happy pony pushed her head to his and laid a gentle kiss onto his nose.

Sin, too dumbstruck to speak, listened to what she said next. “you've got nothing to be afraid of with me.” She lifted a hoof and gingerly touched his cheek. “I've protected you once already, and I'm sure I'll be doing it again.”

“So relax, okay? I know you’re a pony who likes his space and I can respect that. I don't require much, just some affection and trust. Okay?”

His body trembling for some reason, Sin couldn't reply. He wanted to say something, anything, but he just couldn't. Is head was swimming, his stomach was in knots, his entire body was rapidly heating up from the close contact and cooling down from uncertainty.

This entire situation was utter madness, it was emotion and emotion based logic through and through. And he found that a small part of him liked it. The same part of him that liked gambling but another part as well.

He felt his head being slowly tipped forward before receiving yet another kiss on top of his fore head.

And suddenly, for the first time in a very long time, Sin felt as if every thing would be alright. It was inexplicable why, but the problems he knew he had to face just didn't see like that big of a deal anymore.

Comfort was a powerful thing, he was slowly coming to understand