The End of an Era

Pinkie giggled as she stepped back and placed the cap back on the marker, admiring her work on the passed out party goer. Jack had a completed tic tac toe board, (x's won of course), a monocle and a unibrow. Pinkie also took the liberty of writing "Pinkie rules" on his forehead. Rainbow Dash and Fluttershy looked at each other, then over to the two princesses, noting their extended wings, and grinned sheepishly as they walked backwards to hide behind Twilight and Rarity. Rarity was waving a hoof infront of her reddened face, trying to cool herself and regain her composure as Twilight kept staring her sleeping room mate. Luna was staring at the man as well while Celestia looked over to her sister, and then to her extended wings and smiled softly. She then looked back around at the remains of the party and the mostly gone bowl of punch in the corner. Piecing the night's events together she nodded and then spoke. "Twilight Sparkle..."

This caused the purple unicorn to snap out of her daze and rocket her eyes up to the Princesses. She quickly bowed and tried to stammer out a response. "P-p-princesses! I-I-I can explain!"

"There is no need for that my faithful student. We had simply come to see why we hadn't received a report from you yet and we were concerned for your safety." Celestia interrupted her, placing a hoof gently to Twilight's mouth. "I see another one of Pinkie's famous parties were had, and it looks like the guest of honor seemed to mend ties with you six." Celestia chuckled softly.

"Yes Princess... I can give you the report now if you wish." Twilight said as Celestia removed her hoof.

"The abridged version please, it is rather late and I must speak with my sister privately upon returning to Canterlot."

Twilight nodded. "Today after breakfast, Jack and I went over to Rarity's in order to get him new clothes, a set of which he is currently wearing." She said pointing a hoof to the sleeping man. "Then afterwards we went to the market to get his community service settled with the other ponies. He will be pulling delivery carts in town." Celestia nodded and remained silent, allowing Twilight to continue. "Upon returning home Jack said he was tired so I let him take a nap as I rounded up the girls per his request so that he could apologize to Fluttershy. Then Pinkie had a party and now the two of you are here."

Celestia smiled softly and nodded. "Very well, thank you Twilight. Have a good night girls. Come Luna we shall be leaving now." Luna hadn't taken her eyes off of Jack since he had whispered into her ear. Her face remained flat, however Celesita could see the emotions just behind her sister's eyes. The six girls bowed as Celestia and Luna then turned and walked out of the library. As the two princesses took to the sky, the door shut quietly.

"Should we leave him on the floor like that?" Applejack asked, breaking the silence.

"Oh heavens no, we must get him to bed lest he ruin his clothing!" Rarity quickly replied, covering Jack's body in a light blue glow, lifting him off of the ground.

"Heh heh, Rarity's trying to get your pet into bed Twilight." Rainbow chuckled, nudging her elbow into the purple unicorn pony. This caused Rarity to drop him on the stairs as she was carrying him up.

"I am not Rainbow! I am a Lady. And a lady does not take advantage of a sleeping stallion!" Rarity exclaimed causing Rainbow to fall over laughing. Rarity huffed and levitated Jack up again and went upstairs, Twilight following behind to open Jack's bedroom door.

"Just put him on the bed Rarity, I can take care of things from here." Twilight said softly to her ivory friend.

"Of course Twilight, I'll get the girls to help clean up and then we shall be off. It's late and I have work to do tomorrow. Do call for us if you need anything else dear." Rarity said, placing Jack on the bed and hugging Twilight. After receiving a hug in return, Rarity headed back downstairs to help the rest of the girls clean.

Twilight bit her lip as she looked over at the sleeping man. "He'll get quite hot in those clothes, I'm sure he wont mind." She whispered to herself as she approached the side of the bed. She used her magic to slide his socks off and unbutton his shirt, revealing his gently rising and falling chest. As she used her magic to slide his shirt off, the back of Jack's left hand brushed against Twilight's neck causing her to gasp and jump back slightly. Jack rolled over away from Twilight and she then quickly removed the rest of his shirt, folding it and placing it next to the bed. She decided not to remove his pants as she was already struggling to control her body from the last day of her cycle and the few spiked drinks she had during the party. Twilight turned and hurried out of the room, closing the door magically behind her, returning to help the girls finish cleaning.

The Royal Palace in Canterlot

Luna and Celestia landed with a soft clap on Luna's balcony outside of her bed chambers. "Good night Lulu." Celestia smiled and nuzzled the side of Luna's neck. Luna did not speak as she opened her balcony doors and walked into her room. Celestia frowned and followed her sister into her room and shut the doors behind her. "Sister tell me what is wrong. You haven't said a word since we left Twilight's home."

Luna sighed and flopped down on her bed, wrapping her forehooves around one of her larger body pillows. Celestia smiled and sat down next to her sister, running a hoof through her sisters mane. "This is about Jack isn't it."

Luna sighed and punched the pillow she was clinging to lightly. "We are conflicted Tia. On the one hoof, our body wishes for him to hold us. But on the other, we are frightened of what lurks inside him." She said closing her eyes tightly as she remembered the event that happened during her encounter with Jack in the dream realm.

"What are you talking about sister? What do you mean you are frightened of Jack? What happened?" Celestia did the best she could to console her sister. Luna took a deep breath and then recounted the events of what happened when she tried to enter Jack's dream while he was napping earlier in the afternoon.

"During our rest in the afternoon, we saw a new dream cloud appear that did not seem to be from one of our subjects. I entered it to find Jack... No it wasn't Jack, it was something else. Something dark." Luna looked up to her sister as she released the pillow and moved to wrap her hooves around her. "We found that we had no power in his dream as it... It touched me Tia." The sudden drop of her sister's royal speech caused Celestia to gasp and move closer to her. "I couldn't move as it touched me. My body was burning with desire as my mind fought to be free. It told me to stay out or else worse things were to come. I was so scared Tia. I had never felt anything like that before, nor do I wish to again."

Celestia couldn't believe what she was hearing. Her sister was powerless in her own realm to this... thing... inside of Jack. She held her sister and rocked her gently as Luna continued. "Then, while we were at Twilight's library, when Jack touched me and whispered to me, my body betrayed me again. I have never been so confused Celestia." Celestia could feel her sister trembling against her, resting her chin against the top of her head.

"Luna, I must ask you to send me into this dream of Jack's. This event can not go unexplained, let alone unpunished. I do not ask you to come with me, only to watch over me. Should anything happen I want you to pull me out." Celestia pulled back just far enough to look into her sisters eyes. "Dearest Sister, do not fret. We will figure this out together."

Luna nodded and shuffled away from her sister, releasing her hold on her. "Very well sister, get comfortable. I shall watch over you while you do this. Do not attempt to anger him, for I do not know what he would do."

Celestia nodded and climbed onto the bed and laid down next to her sister, sliding the covers over them. "I am ready Luna..."

Twilight's Library

Twilight sighed as she slumped down against the wall in the main room of the library, the remnants of the party finally picked up. She couldn't remember the last time she had stayed up this late for anything other then studying.

"Alright Twilight, we'll be goin' now. Yer sure you don't need help watching over Jack?" Applejack said as she sat down next to Twilight.

"Mmhmm. I'm just going to be going to bed after you girls leave, I'm sure he'll be out for a while with all the dancing he did during the party." Twilight said waving a hoof dismissively.

"Alright, G'night sugar cube. We'll see ya tomorrow." Applejack said standing up and walking out of the library with the rest of the girls, the door shutting quietly behind them.

Twilight sighed and stood up, rubbing the side of her head with a hoof as she ascended the staircase slowly. She pushed the door open and stepped quietly over to the bed and started to climb into it until she felt something in her bed. Twilight gasped as she saw Jack sleeping in the bed and she took a few steps back, looking around the room. In her daze she had walked into his room and almost climbed into bed with him. Her body shook slightly as she smelled his sweat hanging in the room, lighting her loins ablaze with desire. She quickly looked around the room again and picked up his dress shirt he got from Rarity earlier and ran out of the room to hers.

(Sex related content is coming. Ctrl+F "Sex over" to skip)

Twilight shut the door to her room quickly as she held Jack's shirt to her muzzle with her magic, her eyes sliding closed. Twilight climbed into her bed and placed Jack's shirt on top of her pillow. Twilight's body shuddered as she forced her face into her pillow, breathing in Jack's scent. She spread her legs apart as she lifted her rump as high as she could into the air, flipping her tail onto her back. She slid a hoof from her chest down her stomach and in between her teats as she moaned gently, losing herself to her fantasies.

Jack opened the door quietly hearing some commotion coming from Twilight's room. He stood in the doorway as he watched his room mate and care taker pleasuring herself with her face covered by his shirt. He approached slowly as he watched Twilight's hoof rub against her clit, her juices pouring from her inflamed and winking marehood. "Jack... oh Jack.." she moaned gently, her face wiggling around in his shirt, her hoof straining to ease her burning desire.

Jack moved behind her and placed his hands on her flanks, gripping tightly and leaning his face down to her aching pussy. "You called?" He said with a smirk, causing Twilight's head to shoot up and look over her shoulder at him.

"J-j-jack! What are yoooooou...." Was all she could muster as he kneaded her flanks, slipping his tongue from her mouth and trailing the tip around her lips. Twilight moaned again and tried to push her hips back onto his face but he pulled back so he was just out of reach. Jack slapped her flank gently and ran his fingers around her cutie mark.

"Ah ah ah, I'm the one in charge now." Jack said, reaching one of his hands around her and groping a teat and squeezing it gently as he wrapped his lips around her clit, sucking gently. Twilight writhed under his touch as she pushed her face back down into her shirt covered pillow, trying to stifle her moans. Jack gently pinched and twisted Twilight's hardening nipples as he slipped his tongue into her moist love tunnel, slurping down her juices loudly.

Twilight's legs started to shake as she neared her climax from the feel of Jack's tongue and fingers working at her teats. She involuntarily started grinding her hips harder and harder against his face, wishing his tongue to plunge deeper into her. Jack brought his hand that was on her flank up to her tail and tugged firmly, pushing her over the edge, causing her to scream into the pillow as her juices flooded into Jack's mouth.

"Mmm... You taste just as sweet as you smell. "Jack said, as Twilight's knees gave out, her flank landing down on the bed with her legs spread open. The after shocks of her climax slowly subsiding as she pulled the pillow covered with Jack's shirt closer.

Twilight sighed as she brought her soaked hoof from between her legs, whimpering slightly. She rolled over to find a dry spot on her bed and curled up with her face still buried in Jack's shirt. Hopefully these thoughts would pass with the end of her heat cycle.

(Sex over)

Jack's Throne in Canterlot

Celestia appeared in a darkened version of the Canterlot throne room. It's usual marble floor and columns having been replaced with what seemed to be made of basalt. The main carpet was still red as it ascended the stairs to the throne with Jack sitting in it, holding a rather large plush version of a certain blue alicorn. The plush alicorn was about half the size of Jack as he held it in his lap, petting its cloth mane. Celestia slowly followed the carpet up to the bottom of the stairs and looked up to Jack. "It's a very comfortable seat isn't it?"

Jack smiled, his eyes moving down to Celestia. His hand rubbing the head of the plushie Luna. "It sure is. And It's nice to finally meet the beloved Princess of the Dawn."

"You seem to have a thing for my little sister Jack." Celestia said smiling at the Luna doll.

"Isn't she just the cutest thing ever?" He said holding the plushie up facing Celestia. "What art thou doing here sister?" He said making the plushy lean from side to side with his words, trying to mimic Luna's voice, causing Celestia to chuckle lightly.

"Yes, she is very dear. However I came here to ask a few questions. Luna told me what happened earlier when she came by." Celestia's smile faded as she looked up to Jack. He sighed and placed the plushie on the armrest of the throne as he faded, appearing on Celestia's shoulders and leaning his chest against the back of her neck.

"Well did she say she was sorry for staining my carpet at least?" He chuckled, running a hand through Celestia's ephemeral mane. She turned her head and her horn lit up, causing Jack to float up and off of her back, landing in front of her. "What? She did, it's still there don't you see? It's so hard to get stains out of this thing." Jack pointed to a rather large dark spot in between Celestia and himself.

Celestia stomped a hoof as she glared at Jack. "That's enough Jack! I am here for answers as to why you tormented Luna!"

Jack smirked as he took a step forward, his eyes locking with hers. "Why, Tia, I don't think I tormented her. I simply teased her a bit and told her to not come back."

(Grey times ahead. "Grey times over" to skip)

As Celestia looked into Jack's eyes, she didn't see the same gentle determination she had during the trial. She didn't see fear, kindness or love. What she saw was much more intimidating. She saw the look of someone who's killed, and enjoyed doing it. She could feel the heat of his anger radiating from his body with every step he took closer to her. "Celestia, I know what you see, it's written all over your face." She tried to take a step back but her leg wouldn't move.

"What have you done?" She said, her body writhing a bit trying to force her legs to move. "Luna get me out of here!" She called out.

Jack laughed and snapped his fingers, causing Celestia's eyes to snap to his hand. She had only seen one other being snap it's fingers. Then she heard a loud whine coming from the throne. There she saw Luna chained down on her haunches with a black collar around her neck. "I don't think Luna will be doing much of anything. Now I'm going to make this either extremely easy, or extremely difficult for you Celestia." Jack turned and walked up the stairs to the throne and stood next to Luna, running his fingers slowly down from the tip of her horn, causing her wings to slowly open, tears forming at the sides of her eyes.

"Get your hands off of her Jack!" Celestia commanded, watching her little sister writhe under his touch. Jack leaned down and whispered into Luna's ear, causing her eyes to snap open, tears quickly falling down her cheeks as she shook her head.

"No? Oh dear sweet Luna why not? You're so beautiful though..." Jack smiled darkly as he turned his head over to Celestia. "I thought you were the smart one Celestia. Surely you don't think I'm anything like that worthless sack of flesh. Your sister knows better, don't you Luna?" He said, running his fingers down from her horn to wipe her tears away. Luna nodded slowly as her eyes never left Celestia's.

"Celestia I'm surprised at you, you know. Who knew the Princess of the Sun had such a dark sense of humor." Jack said, trailing his fingers down Luna's neck, around, and then back up through her mane. "You probably don't know this, but what you did to Jack made me laugh so hard I cried." Celestia watched him, her eyes narrowing.

"What are you talking about?"

"How do you think Jack got that scar on his neck Celestia?" Jack pulled the collar of his shirt down and pointed at the large white scar around his throat. "In our world, there was an ancient philosopher who attempted to describe the punishments for certain undesirable actions in society. One such description was what happened to those who committed suicide."

Celestia's eyes went wide as she realized what he was talking about. "No..."

"Yes, and in this description, the souls of those who committed suicide were trapped inside of trees, their souls doomed for eternity to feel only thirst and pain. Instead of being made of wood and bark, the trees would be made of the bones and tendons they had in life, so with every gust of wind, their bodies would be wracked with pain. In this Wood of Suicide, the trees would grow so close together that their roots competed for what little dry soil was under them, splintering and fracturing the roots. And any who would attempt to trek through, would break the weak and thin branches of the trees. So in a way, you condemned him to his own personalized hell."

Celestia shook her head quickly. Was that how Jack thought of her? She couldn't have known this. Surely he didn't think that's what she meant when she sent him to live with Twilight, but the horror still plagued her mind.

"Now, unless I'm mistaken, Luna here is the only one who can enter dreams on command, and you needed her help to get in here. So I'll give you a break since you're so brave." Jack grabbed the side of Luna's collar and shook it gently as he spoke to Celestia. "You can get a glimpse into Jack's dreams, or you can leave. Just know that the knowledge comes at a cost."

Celestia paused as she looked from Luna to Jack. "What cost?"

"If you want a peek, I want your sister's maidenhood." He said, running his fingers through Luna's mane. "I'm sure Jack would be quite upset to find that his favorite Princess was deflowered, but I take my charge very, very, seriously..."

Celestia recoiled slightly as tears streamed down Luna's cheeks, her head shaking slowly. "Very well, we shall leave and never return. Just let my sister go. Please." Celestia whispered, tears forming at the side of her eyes.

Jack smacked his lips and frowned, leaning down to Luna and kissing her cheek lightly. "Aw your sister is such a stick in the mud. Just think about all the fun we could have had Luna."

(Grey times over)

Jack snapped his fingers, the collar around Luna clicking open as Luna vanished from the throne room. "Well I can't say I'm not disappointed Tia. I was looking forward to a sweet treat tonight. But since you said please, I should play nice. You also played along in the beginning with me, so I'll give you this before you go." Jack faded and then appeared next to Celestia, wrapping an arm around her neck, holding his other hand up in front of both of them, a screen appearing before them. "Here's the last images of Jack's dream before he wakes up. Speaking of which, I think it's time for you to raise the sun is it not?"

On the screen in front of Celestia, she see's the Jack she saw at the party held in the air by a dark blue three clawed hand, his body consumed in green flames. He was screaming and writhing in agony as if his very soul was being burnt out from within him. She could smell his flesh and hair burning, but she saw no signs of damage. With that she faded out of the dream, waking up quickly to a crying Luna holding her close.

Jack's Dreamworld

Jack opened his eyes and found himself in the large room with the lit empty pedestal. His eyes scanned the darkness beyond the pedestal and behind him. As he turned his head back to the pedestal, he saw them. The smoldering green orbs floating just beyond the reach of the light. "Your darkness will consume you and those around you," The deep voice said. As the voice spoke he could see the eyes flashing with its words.

Jack stood silently, trying to get a read on whatever it was he was seeing. If the orbs were indeed eyes, then this creature was at least eight feet tall. "What do you want with me?" Jack asked. The being stepped forward, the pedestal dropping into the floor as it stepped into the light. Jack was right, they were eyes, but this creature was slouching over slightly. It's dark blue skin covered its body, with a large purple cloth that reached from just under its eyes to just above the floor. Behind it's head it had what looked like black dreadlocks bound together with a golden ring. It had  golden pauldrons on that were set with deep green smoothed emeralds. Further down its arm was a large golden bracer with emeralds studded down its side. A purple cloak surrounded the rest of its body, but he could see that it had only three fingers ending in long black claws.

"You will not survive your test without this gift. This will allow you to use your mind, body, and spirit to overcome any obstacles that should arise during your trial. You will need this if you wish to defeat the darkness within you."

Jack stood silently, looking up into this being's eyes. He took a deep breath and then nodded. "Alright. I'll take it."

The being suddenly grabbed Jack by the throat and squeezed, lifting him up off of the ground. Jack struggled against it's grip as his body started to feel warmer and warmer. It felt like his blood was boiling as he gasped. His eyes started to burn so he closed is eyelids tightly trying to rid himself of the pain. Jack's eyelids suddenly opened as his eyes glowed with the same green flames as the creature before him while the rest of his body erupted in dark green flames. He writhed and struggled against the vice like grip that held him aloft, it felt like an eternity every moment as he was immolated.

Jack's room

Jack sat up quickly, screaming at the top of his lungs, his fists clenched and his muscles flexing.Twilight quickly leaped back away from him in terror as she watched steam rise off of his body as he shook. As he regained his senses he placed his hands over his face and started taking deep breaths. "Jack... Are you alright?" Twilight asked quietly.

"Y-yeah.. Just one hell of a bad dream..." Jack said slowly, trying to get his breathing under control. It all felt so real, the heat of the flames against his skin, the burning inside of his body and his mind. He ran his hand across his chest and then he realized where he was. "Uhm.. Twilight... how did I get in my room and what did I do with my shirt?"

Twilight blushed and looked away. "Well after your performance last night, you passed out downstairs. So we brought you up here so you can sleep in your bed." She then remembered that his shirt was still in her room draped across her pillow. Scrambling for an answer in her mind she blurted out "And your shirt was dirty so I took it to get it cleaned!"

Jack then turned to look at her and smiled. "Thanks Twilight, and sorry if I did anything too crazy last night. I think there was some alcohol in that punch... I haven't drank that much in years."

Twilight let out a breath she didn't know she was holding and looked back up to him, smiling. "Well, today is your first day of work, so I'll head down and make some breakfast while you get cleaned up. Don't want to be late for your first day." Twilight then giggled, looking at the doodles on his face. "You might also want to wash your face really well. Pinkie went a bit overboard last night."

Jack thought back and his eyes widened. He passed out in the middle of a party, there was no telling what was all over his face so he quickly got up and ran to the bathroom. He smirked as he looked into the mirror and chuckled. "Well g'day to you my good sir." Jack said to himself, tipping an imaginary top hat before he started to wash his face. After a few minutes of scrubbing he left the bathroom to collect a change of clothing and a towel. "I'm getting a shower now Twilight, I'll be down in a few!" He called down to her. He didn't get a response so he shrugged and walked back into the bathroom, closing the door behind him.

As Jack adjusts the knobs to the shower he starts humming a song to himself. He then thought back to the previous night, trying to string the memories together. There was the punch, then dancing, then something about a spell from Vinyl. Why didn't he have a hang over? Was that dream actually real? Jack ran his fingers through his hair as he knelt under the shower head that was too short to be effective while standing. Jack reached over and picked up a purple bottle of shampoo and squeezed some into his hands. As soon as the smell hit him he awoke from his daze and realized he had grabbed the wrong bottle, but by then it was too late, he was already scrubbing the top of his head with it.

Oh you smell wonderful now.

Can it, it was a mistake.

Mmhmm, and I'm sure that rubbing all over the ponies last night was a "mistake" as well. Or maybe it was just because you were drunk?

...

Hah, thought so...

...

Oh, the silent treatment huh? Well I can take a hint, I'll be around. You know, someone has to keep this dirty mind of yours clean.

Jack sighed and continued washing himself silently. Meanwhile, downstairs as Twilight is preparing breakfast some strange sounds are heard coming from the main area of the library. "Twilight what is that?" Spike asks, leaning out and looking around the room. Twilight turns her head and then walks out of the kitchen. The phonograph from last night was still enchanted and the sounds coming from it was the song that Jack was humming to himself in the shower. Her curious nature got the better of her as she stood right infront of it, getting a sudden blast of sound right into her face. Twilight took a step back and used her magic to tone down the volume a bit on the enchanted phonograph as she listened intently to the song that was playing. She sat stunned as she could feel the music reverberating in her chest.This song was so different to the one she had heard last night at the end of the party. Is this how Jack felt deep down? How could he keep this all inside of him? Why did he feel this way?"I'm scared to get close, and I hate being alone, I long for that feeling to not feel at all. The higher I get, the lower I sink, I can't drown my demons, they know how to swim."

Twilight suddenly remembered that she had left breakfast cooking on the stove as the song came to a conclusion, so she ran into the kitchen to make sure nothing had burned. She quickly turned off the oven, the shredded potatoes she made were browned a little too dark for her liking, but hopefully Jack wouldn't notice. As she levitated plates out to the table Jack rounded the corner.

"Mmm.. Smell's good Twilight." Jack said, taking his place at the table across from Spike. "Mornin' Spike."

Spike nodded to him and yawned, rubbing the sleep out of his eyes. Twilight hovered the pans of breakfast over the table and started scooping portions onto the three plates. She had made a rather quick and simple breakfast of hashbrown style shredded potatoes with scrambled eggs along with a pair of slices of wheat toast for each. "Dig in everypony." She said proudly as she floated the pans to the sink.

Jack rubbed his palms together and then picked up his fork, digging in quickly and closing his eyes as he tasted the food. "Oh man, this is probably the first home cooked breakfast I've had in years."

Twilight smiled softly to him as she ate silently, remembering the song she had heard earlier. What sort of life had Jack lived prior to being found by Fluttershy? Twilight's smile faded, questions bombarding her mind as she watched him happily eat. How could he smile if he felt that way?

"You going to be alright without me today Twilight?" Jack smirked as he finished his food and leaned back in the chair.

"Of course she is! She's the most talented pony in Ponyville, and she's got me to be her number one assistant!" Spike said, puffing his chest out proudly. Twilight realized that she was staring at Jack and then shook her head quickly as she resumed eating.

"Good, wouldn't want anything to happen to the warden while I'm away." Jack chuckled and stood up from the table. "Well I'm going to get going, don't want to be late for work and I'm sure you two have stuff to do besides baby sit me." He carried his plate over to the sink and rinsed it off before setting it down and walking out to the front of the library.

"Should you be letting him go alone like that? What if he gets into trouble?" Spike asked, looking over to Twilight watch Jack leave the kitchen.

"I'm taking a chance and hoping that I'm right about him. He shouldn't be a problem unless provoked, and we can't hover around him all day or we wouldn't know if he learned his lesson."

"Yeah well, I still don't like it." Spike said, crossing his arms.

"Well that's why the Princess left me in charge." Twilight chuckled and rubbed a hoof on top of Spikes head.

Jack pulled the door closed behind him and headed for the market place. After a few minutes of walking he found a large open garage type workshop. Inside he saw a much larger then average dark grey earth pony with a white mane looking at some scrolls on a desk. He had light brown eyes and a pair of broad rimmed glasses perched upon his muzzle. Twilight had introduced them yesterday, this stallion was one by the name of "Mr. Move-it Quick." The mark on his flank was a wooden wagon wheel behind a large scroll, perhaps signifying a shipping master or some such job title. Mr. Move-it, as he wanted to be called, ran a large delivery dispatch in Ponyville that assisted the post office in delivering packages.

"Mr. Move-it, it's Jack. I'm here for work." Jack said as he approached the stallion. Move-it looked up and nodded. "Git ova dere and git hooked up to yer cart. You're late!" Move-it shouted. Jack wasn't actually late but he didn't argue. He was the only one left in the garage and there was only one cart left. He had to have special straps made for it so it fit around him. Jack looked in the back of the cart where several pony sized packages waited in the back of it. Shaking his head he strapped up and picked up the delivery list. "Derpy get your flank out here!" Move it yelled into the back room, causing a light grey pegasus with a blonde mane and golden eyes to rocket out and stand next to him saluting.

"Derpy you're going to show this... Jack... where to make deliveries to. He can't read because he's too stupid so you're going to read for him. Don't buck anything up!" Move-it sternly said, motioning over to Jack who was watching the event play out. As Derpy dropped her salute she trotted over to Jack and the two of them made their way out of the garage and onto the main street of Ponyville.

"Sorry about Mr. Move-it," Derpy said as soon as they were out of ear shot of the garage, "he's just putting up a show to make sure you know he's in charge. He's not usually like that."

Jack smiled and nodded, grunting a bit from the weight of the overloaded cart. "It's alright... he called you Derpy? Is that your name?"

"It's actually Ditzy, but everyone calls me Derpy because of my eyes." She said somberly. "It's also because I'm a bit of a klutz and I'm always messing things up."

"Hey Ditzy, it's alright, I mess things up all the time. Don't let it get you down. At least you can read!" Jack chuckled softly, doing his best to cheer her up. "Besides, you're the first pony to not attack me outright, so you're okay in my book."

Ditzy smiled up at Jack and then nuzzled against his leg. Jack placed his hand on top of her head and scratched behind her ears. "Oh that's nice..." She said softly as they walked along. Reluctantly she withdrew herself from his reach and looked down at the paper. "Let's see... First place is... Just down the road here. Carrousel Boutique."

"Huh, Rarity's place. I know the way." Jack shifted the straps that were starting to dig into his body as he pulled the cart along down the road. Thankfully due to either the crafts-pony-ship or the constant travel from ponies, the roads were smooth enough for the cart to coast along quickly and without much effort.

As Ditzy and Jack arrived to the Boutique, he could see Rarity wandering around on the shop floor, even though the sign out front said she wasn't open for business. Jack pulled the cart up as close as he could to the porch and then unhooked. He then went over to the door and knocked firmly, causing the white unicorn pony inside to jump. "I'm sorry but we aren't open yet dear!"

"Special Monster Delivery service for one Ms. Rarity." Jack called through the door.

Rarity looked up and turned and looked at the door, seeing Jack standing on the other side. "Jack, darling, why didn't you say so in the first place?" She quickly approached the door and opened it, looking over to see Ditzy standing next to the overloaded cart. "Oh dear, is this what you'll be doing for work?"

"Yeah, it's not as heavy as it looks, but I don't really have time to chat. If you could just sign this I'll get your package." Jack nodded and held out a clipboard and quill. Rarity looked at the paper and then scribbled her signature after taking the quill in her magic. Jack took the clipboard and quill back and set it in the cart. "Alright Ditzy, show me which ones are Rarity's and then we'll be off."

Rarity paused as Ditzy started flying around over the back of the cart and pointed out several of the larger packages. Jack sighed as he climbed into the cart and slid some packages around, freeing up the first of the pony sized packages. He grunted as he hefted the package up and carried it into the shop. "Where do you want this?"

Rarity waved a hoof off to the side of a counter with a very old looking cash register. "Just place it down there darling. And forgive me if this is rude, but why did you need Ditzy to point out which packages were mine?"

Jack placed the large parcel down at the instructed spot and let out a relieved sigh. "Well I can't read pony language, so Ditzy there is helping me on my deliveries until I can learn how to read. I think Twilight was going to start teaching me tonight, unless something else comes up."

Rarity gasped as she stared at the man walking back to the cart. "You can't read? That's simply dreadful, dear I'm so sorry!"

"Hold up now, I said I couldn't read pony language, not I couldn't read at all. I'm actually quite well read for where I come from." Jack said hefting another package up and slowly making his way into the shop again.

"Oh right, of course, silly me." Rarity chuckled and then went back to work, prepping her store for opening. "Oh, whilst I have you here, Jack I want to let you know that I'll be dropping some more clothing off for you this afternoon on my lunch break."

Jack sat down the third and final large package with the other two and wiped the sweat off of his forhead, already starting to become short of breath. "Great, I have a feeling I'll be needing them much sooner then I thought if I'm already sweating like this. Well I'll let you get back to work, I'm sure you don't want me messing up the place. Have a good day Rarity."

"Of course, you too darling." Rarity said as she waved to Jack walking out of the shop.

"Well Ditzy, that went better than expected." Jack said as he strapped himself back to the front of the cart.

"Yep, Ms. Rarity is such a nice pony, even if she does seem a bit dramatic."

"Heh, Yeah. Well she didn't stab me or anything, so that's a plus. Anyway what's next?"

After a few hours of work with a quick break for lunch, the last of the packages had been unloaded from the cart, but exhaustion was beating Jack down with every passing minute. He was covered in sweat and breathing heavily, fidgeting with the straps in order to relieve some pressure, but only succeeding in tiring himself out more.

"Holy shit, this is some tiring work." Jack said, wiping his forehead with his already sweat soaked sleeve.

"You did pretty well today Jack! We got through all the orders before quitting time, that means you get to go home early!" Ditzy said happily, flapping her wings and floating next to him.

"Thank the gods, I'm going to need a nap after this if I'm going to make it the rest of the day."

"I'm sure Mr. Move-it will be happy, most ponies don't finish early on their first day!"

"Well I couldn't do it without you Ditzy, both literally and figuratively. You were a great help."

Ditzy smiled and then landed next to him as they approached the delivery garage. "No problem, I hope I get to help you again tomorrow. You're really nice and I didn't mess anything up today."

Jack laughed and patted her head gently. "Don't jinx yourself, we're on the home stretch now."

As Jack and Ditzy entered the garage, they approached Mr. Move-it as he was shuffling papers on his desk. "Hey boss, we're done with the orders."

Move-it looked up to see Jack and Ditzy standing in front of his desk. He looked over at the clock and then back to the duo, noticing how wet Jack was. "Well this is a first. Derpy, did he just throw the packages off the bridge and follow them into the river?"

"No Mr. Move-it. He delivered every one of them. I offered to help but he did all of the work. I just showed him where to go like you told me to." She said just loud enough for him to hear it, her eyes looking down to the front side of the desk. Jack looked down and over to her, and rubbed her back gently, trying to give her some comfort.

"Hmm... Well I'll hear about it if you are lying to me. Since you finished early and we don't have any other orders ready, you can put your cart back and get out. I'll see both of you tomorrow morning."

Ditzy quickly picked her head up and smiled. "Oh thank you Mr. Move-it. I promise you won't have any complaints come in about us!"

Jack remained silent and nodded, looking down into Move-it's eyes.

"Come on Jack let's go before he changes his mind."

"Alright Ditzy." Jack looked down at his companion and patted the top of her head. He then turned and set the cart back where he found it, making sure that it was ready to be loaded tomorrow morning. Jack and Ditzy then left the garage just as quickly as they entered to see a few ponies pulling empty carts towards them just down the road.

"I'll see you tomorrow Jack, I have to pick up my daughter from school soon."

"Alright, tell her I said hello, and have a good rest of the day if I don't see you again." Jack waved as Ditzy flew off into town. Jack sighed, exhausted from his first day of work and headed towards the tree library for some much needed rest. Finding himself alone again he started humming another song quietly to himself as he undid the top two buttons to his shirt, trying to get let out as much heat as possible to cool down.

As Jack reached the library, he leaned over slowly and untied his dust covered boots. Pulling his boots off and setting them outside next to the door, his feet throbbed with dull pain at their new found freedom. He stood back up, placing his hands on his lower back, trying to stretch out the soreness from his first full day of work. He pushed the door open and tenderly stepped into the cool library. His presence didn't go unnoticed as he entered however.

"Jack we need to talk." Twilight said as she lifted her head from the book she was reading to look at him.

Uh oh.. what did I do this time..? Jack started to run through everything he did this morning before leaving the library. His face remained blank as he awaited to see if she would tell him what was wrong.

"Jack it's about the spell that Vinyl put on you last night. The spell was still working all day and playing music from your mind."

Jack let out a sigh and chuckled a bit. "Oh man you had me worried for a minute there Twi'."

"Jack, this is serious, those songs I heard. They were... so full of sadness and pain. I'm worried about you Jack." Twilight stood up and walked over to him, looking up into his eyes, concern showing on her face. Jack sighed and then patted her head gently, scratching just behind her ears. Twilight smiled and closed her eyes.

"Don't worry Twilight, I'm fine. It's just music to help the day pass. I'm sure there were some other nice songs that popped up right?"

Twilight reluctantly lifted her hoof up and pushed Jack's hand away from her head, frowning again. "There was maybe one Jack."

"There, see, one happy song. Now if you don't mind I'm all sweaty, dirty, tired and I need a shower." Jack smiled down at her and then turned and headed up the stairs to shower.

Twilight sighed and sat back down on the cushion next to her book, levitating out a scroll and quill, she began her letter to the Princess.

Dear Princess Celestia, Today Jack woke up from a rather powerful night terror. He seemed to be fine after calming down but once he left to do his duty for Ponyville, the phonograph that was enchanted last night for the party, started playing extremely powerful and sad music. When I questioned him he avoided answering me. I am worried about him and you told me to report any unusual behavior. He seems to usually be kind and friendly, but what I heard today, it seems he is very deeply troubled. I will be doing my best to help my new friend in whatever troubles him. Your faithful student, Twilight Sparkle.

"Spike, I need you to send a letter to the Princess please."

Spike walked out of the kitchen, munching on a rather large yellow gemstone. "Sure thing Twilight." Spike took the scroll and opened the window, slowly igniting the scroll as it flew off into the distance. On his way back to the kitchen, Spike burped and a scroll popped out of his mouth. "Wow, I think that's a new record Twilight!"

Twilight quickly pulled the scroll from the dragon's claws and read it quickly. "My Faithful Student, I ask that you use your best judgement when it comes to this situation. Please be cautious when interacting with Jack as we cannot be sure that he is entirely safe. I have faith that he will open up to you in his own time, so I ask that you be there for him when he decides to. My sister and I have matters that require our immediate attention so we shall be in touch soon. Please keep us updated with anything out of the ordinary. Princess Celestia." Twilight rolled the scroll up and placed it on the shelf next to her.

After a few minutes, Jack descended the stairs quietly, rubbing the towel through his wet hair. He looked over to Twilight completely engrossed in a very old looking tome. A very sly smile crossed his face as he lightly continued down the stairs, his steps slowly growing closer to the preoccupied purple pony, not making a sound. He was close now, just another step, and then... He quickly and firmly wrapped his arms around her neck and pinned her down. "Gotcha!"

Twilight squealed as she kicked the book away in fright and started to struggle against him. Jack rubbed her neck gently as he chuckled. "Easy Twilight I got ya, you're alright."

"Jack! That wasn't funny! You scared the tartarus out of me!" Twilight squeaked, quickly calming under his touch.

Jack laughed a little harder as he brought a hand up and lightly scratched behind Twilight's ears causing her eyes to close immediately and lean into his hand. "Ohhh someone like's 'skritches' hmm? Well how about 'chin skritches'?" Jack moved his other hand and lightly scratched under her chin. Twilight went limp as she leaned against him, smiling broadly.

"Oh my... this feels so good..." Twilight cooed softly. Just as soon as it began, it ended, Jack pulling his hands away and sitting next to her. Twilight's eyes opened quickly as she snapped her head to look at him. "Hey! I didn't say stop!"

Jack laughed again and shook his head. "Sorry, but if you want more then you're gonna have to teach me how to read your scribbles."

Twilight's eyes lit up like she had just recieved what she always wanted for Hearth's Warming and dashed off upstairs to get some things. While she was up stairs doing whatever she was doing, Jack looked over to the book he had seen Twilight reading. It was a very old and heavy book with sturdy thin wooden flaps, covered in leather and embossed with some pony text. He opened it gently, feeling as if it was going to crumble into dust if he breathed wrong. The pages were made of a much thicker parchment than he had seen Twilight write on, and the writing seemed slightly faded. As he turned the pages slowly he could make out a few pictures of different unicorns and some shapes that looked like constellations of stars. Jack quickly closed the book as he heard Twilight coming down the stairs, she had her saddle bags draped over her hips and was levitating a few bottles of ink.

"I picked up some books from Cheerilee, the teacher at the school, so we should have everything we need for a while." Twilight said as she placed the inkwells and a bundle of quills infront of him. She then opened one of the flaps to her bag and pulled out a group of thin wooden plates bound together with twine. "First thing's first, you have to learn the letters."

Jack scooted back as the large wooden "book" landed in front of him with a loud clack.

"Now, we'll get as far as we can tonight so that I can gauge how quickly you learn and build a better schedule around that." Twilight said, floating some parchment over to Jack as she sat down next to him.

"Alright, well, daylight is burning so let's get this show on the road shall we?" Jack reached out and open the wooden tome to find a rather large scribble carved into the first "page". He looked it over and scratched his head, taking a quill and a piece of parchment as he attempted to transcribe what he saw, albeit on a smaller scale. He quickly found that writing with a quill and ink, as opposed to a normal human pen, was akin to attempting to draw a line in the sand with a broom. Dipping the end of the quill into the ink, he picked it up to write, causing drops of the excess ink to splatter over the rest of the page. "Oh shit... Well that's what I get for being to hasty heh heh..."

Twilight smiled at his enthusiasm and quickly cast a spell to levitate the spilled ink from the floor back into the inkwell. "Take it slowly, let the extra ink drain from the quill before attempting to write. Now try again."

Jack nodded and dipped his quill in the ink, lifting it slightly and tapping it gently against the rim before he started writing. As he scribbled on the parchment, Twilight spoke up. "This is the first letter of our alphabet, the letter A. We have twenty six letters, six vowels, and twenty consonents." As Jack finished copying down the large letter in the book the quill snapped as he listened to her.

"Hold the fuck up. You mean to tell me that you use the same alphabet that I do? Just with these weird fucking symbols?!"

Twilight looked up at him startled from both his raised voice and the profanity he used. "Well... I don't know what alphabet you use, but this is the one that is the basis of our language."

Jack dropped his quill and grabbed the sides of Twilight's face, pulling it close to his. "This is going to make things so much easier! I thought I had to learn a whole new language! I just have to learn the alphabet and I'll be able to decypher your blasted pony writing!" He shook her head very lightly, causing her eyes to roll around in her head comically. Jack released his hold from Twilight as he quickly dove back into the book, flipping a page and scribbling down what he saw, writing his alphabet next to it.

Twilight rubbed her face with a hoof gently as she watched Jack fervently flip through the pages. She had never seen another pony so eager to learn something she tried to teach them. Her face flushed as she watched the man accidentally break a few quills in his haste to copy down what he learned from the book. As he closed the book he took a blank piece of parchment and started scribbling something down onto it, glancing back and forth from his notes to the paper.

"Tell me what this says Twilight, I want to see if I'm right." Jack said, holding up the new piece of paper to her face, the ink slightly running from the sudden movement.

Twilight giggled as she picked it up with her magical grasp and ran her eyes over it. "HELLO TWILIGHT SPARKLE. MY NAME IS JACK AND THIS IS MY FIRST LETTER. I HOPE THIS IS CORRECT." As she recited to him, Jack wrapped his arms around her and squeezed tightly. "Can't... Breathe... too.... tight!" Twilight gasped out, causing Jack to release his hold on her.

"Heh, sorry. You don't know how much not being able to read was bothering me." Jack rubbed the top of Twilight's head gently. "Twilight, you have just given me one of the greatest, but most underrated gifts ever. The gift of literacy. Thank you." He reached out and hugged her again, much more gently this time. Twilight reached her hooves around his chest and returned the hug, smiling brightly.

Twilight pulled out another, much smaller book and set it in front of Jack. The rest of the night, she instructed Jack on the proper way to hold a quill and in how to write the lowercase letters. Jack had several pages filled with letters as he attempted to commit them to muscle memory, however for only one day of studying, he knew this would not be enough. The subtle nuances of the letters eluded him at this time, but he continued with a determination the likes of which Twilight had never seen. Only a quick break for dinner could distract him for any long amount of time before he resumed his studies. Twilight had wondered if this was how she looked when she was engrossed in a particular mystery that required a large amount of research.

The night drew to a close after Twilight had to magically lift Jack from the ground and throw him into the empty bathtub upstairs. "Get cleaned up and get to sleep. Make sure you wash your hands extra well to get the ink off of them. I don't want to replace my sheets because they have ink all over them."

"Yes mistress..." Jack said, rolling his eyes. Twilight glared at him sternly before chuckling. She turned and left to clean up downstairs as Jack got ready for bed. As soon as his hands were clean, Jack yawned rather loudly, the exhaustion from the work he did earlier that day, as well as the fact he skipped the nap he thought he would take, hit him as soon as his mind slowed down. He had just enough energy to make his way into his room before he collapsed on the bed, groaning silently into the pillow and feeling his body go slack. He pulled his shirt off and crawled under the covers, passing out quickly.

Twilight made her way up the stairs and saw that Jack's door was open and the light was on, so she went in to see him laying down face first into the mattress. She smiled as her horn lit up, glowing a soft purple as she pulled the she flicked the lights off and shut the door to Jack's room.