The Tail of Tails

by BillRT

Rating: mature
Tags: Comedy, Adventure, Pinkie Pie, Crossover, Sex, Twilight Sparkle, My Little Pony: Friendship is Magic, Alternate Universe, Human, Other, Romance
Length: 9494

Tails (from the Sonic game series) ends up in Ponyville and has emotional and important relationships with the Ponies we all Know and Love. What does it all mean? Why do we dream? This question and more are answered. MLP-centric many-fandom crossover

Tails the Fox, after an emotionally draining breakup with Tifa Lockheart, finds comfort in the bosom of a humanized Twilight Sparkle. But why is Twilight in this world with everyone else? What happened in Ponyville that caused all this? Why does Pinkie Pie feel some kind of connection with Tails? These and many more questions are raised, then answered, in this story. Very smutty clop with some involved plots story-wise.

Comments and criticism are welcome. I am learning and

Published 2013-05-05 01:20:02 UTC
Last updated 2013-05-05 01:20:02 UTC

Chapter One: Twilight Sparkle

WHOOOOOOOOOOOOOOOSH... Whump!

Tails had the wind knocked out of him as he landed on what felt like grass. The din of the rushing air faded, and the bright purple glow ebbed away as the portal above him closed. Tails kept his eyes shut, as the dizziness from the trip hadn't quite subsided. After a moment to collect his thoughts, he stood up. He tried to, anyway. But this attempt was met with him falling forward face first back into the grass, getting a considerable amount of dirt in his mouth. "Ugh, gross!" He said, spitting, before attempting to wipe off his tongue with his hands. Something hard clocked him in the head, angering him further. He looked at the fairly rigid object, and noticed it was a long, cylindrical hoof. Shocked, he looked at his other hand. The same. And his feet. His body! His head! His-- "Phew," he sighed. "At least my tails are still intact."

Collecting himself once again, he attempted to stand normally. Wobbling his 2 hind legs, he barely managed to become upright, before quickly becoming horizontal and sighing. "Good," he said to himself. He strained once again, this time using all 4 legs in an attempt to not fall over. "...can't even stand up, doubt I'll be flying any time soon. ...Idiot." He tried to spin his tails, but they just wiggled around a little. "God," he thought, "what a horrible horse I make." He turned his head in surprise in response to a crunching sound in the nearby bushes. "Hello?" He asked, unsure if he should be scared. "Is somebody there?"

He creeped closer and closer, now tweaking his ears in the direction of the punctual crunching. Curiously, he could make out a distinct metallic springing noise right after each crunch. Before he had time to process and try to understand the source, it became readily apparent. After a final sproing, a bright pink pony leaped into the clearing, screamed in shock and knocked Tails head over hooves back into the middle of the grass patch. Tails opened his eyes and found himself staring into the bright blue eyes of someone who was obviously very happy to see him.

"Uh..." Tails started, unsure of where to start. The pink pony inhaled deeply, before shouting her reply. "Hiiii!!!" She said, jumping off him. She landed and blew a shitload of confetti in his face. "What-- come on," Tails said, wiping the pieces of paper off his snout. "Who are you?" he asked this pink horse.

"IIIIIIIIIIII'M YOUR NEW BEST FRIEND, PINKIE PIE!!" she shouted, smiling a smile wider than any Tails had seen before. "And I'm gonna be your new best friend!" Tails appreciated the sentiment, but knew that wouldn't happen. "Nobody can take Sonic's place, but I appreciate the sentiment. Where am I?" he asked.

"Sonic? Hm... Oh!" she exclaimed, walking a circle around Tails.

"...what are you doing?" he asked, as she circled around him to apparently look at his butt.

"...Oh! Sorry, I was just noticing that you had two tails! That's neat!" Her face suddenly went from gleeful to furious. "Now WAIT just a minute, you rudey rude guy! I told you my name, so you BETTER tell me yours!" Pinkie reared up in an attempt to appear threatening, but quickly burst into laughter. "Pahahah! Sorry! It's fun to scare people sometimes, especially when they're a new friend. I haven't seen you around before! Well, at least I don't think I have! Where are you from? What's your name?" She beamed a stunning smile in his direction while asking these questions, and Tails found himself at a loss for words. It'd be hard to quickly sum up who he was, or how he got here.

RIIIIIIIING!

The bell ringed.
"Great, the class bell ringing. Just what I always wanted for Monday morning." The two-tailed fox sat up in his seat. He looked around at his friends. Well, they weren't all his friends. His friends in the room were Mario, Peach, Sonic, Knuckles, Rouge, Amy, Tifa, Yuna, Haruhi Suzimiya, Twilight Sparkle (humanized,) and Alyx Vance. His enemies in the room were Liquid Snake, Dr. Eggman, Yuki Nagato, Tomo Takino, Twilight Sparkle's evil twin, and that bastard Cream the Rabbit.

He, being the fox he is, always wanted to be more than just friends with Tifa, though, so like a fox he would try to be cunning and play tricks on her to make her like him more than she did before.

One trick was to break into her house while her family was outside after he set a small fire in the attic and they ran outside. He got on Tifa's computer and made it so whenever she typed "love" or "boyfriend" it would always change to "Tails," cementing the mental connection between the word and the name of the fox that longed for her so deep-wise.

Another trick was to figure out what she is allergic to and give her a tiny bit of it in her 2% milk at lunch so she would have to go to the nurse and go to sleep so he could look at her in the nurse's office, often by faking his own sickness and such, or by falling down on purpose so he would bleed a little for concern by the nurse.

The nurse would often joke "Okay, Tails, you've been to see me almost every day this week! We are going to have to make your own room down here if you keep it up! Get better kiddo!" Tails enjoyed the inside jokes, but what he enjoyed the most was Tifa's luscious freshly pubescent curves.

One of Tails' favorite things to do in sex ed class was imagining sex with Tifa, while sitting right behind her he always got to look at the back of her head and imagine shooting sperm loads all over her hair. He once heard a rumer that sperms have moisturizing qualities and some other powers, but he never checked personally. Maybe someday he and his love could try this handy trick out. (AUTHOR'S NOTE: I have never tried this, so stop asking, okay.)

The kids all piled into the room and onto their desks, but Tails wondered where the teacher was. "Hunh," Tails mentioned aloud, "Where is Mrs. Frizzle?" Tails remembered the day Ms. Frizzle became Mrs. Frizzle, and nobody from class was invited to the wedding except him because he was her favorite student for the grades he got and his helpful nature.

Haruhi noticed a note on the desk, and told Tails about it. "Hey, fox boy, pick up that note and read it. Or don't, it's not like I care or anything. If I get bored of this world, I'll just make a new one!" the beautiful high school girl said, turning around and flipping her hair sideways.

Tomo Takino was tired of Haruhi's attitude. She jumped in a flip and started getting hyper! "C'mon, Har! Get yourself out of the dumps and get happy! It's a beautiful day! Full of opportunity! That's what my Uncle Markus says, anyway!" She landed her flip perfectly and sat back down, giving a high five to Sonic as she sat back down.

"Sweet flip, Tomo! That was way past cool! It was practically Super Sonic!" he said, laughing his signature laughing style. Everyone laughed except the bad kids. Tails stood up to check the letter on the desk. He picks it up with his paws and started to read it out loud for the others to hear.

"Tails thank you for finding the letter. I will be out today for 2 reasons, one personal and one medical. Please take over class for the day, as I don't want to tell the principle about my absence and get in trouble. I, Mrs. Frizzle, think you are a very gifted fox and I trust you can deal with today's lesson to teach it." Tails thought to himself, "Great..."

As Tails turned tail to sit at his desk again, he walked towards his desk. On the way there, he remembered the note from Mrs. Frizzle and sighed again. "*sigh,* I guess it's up to me to teach class today--" WHAM! Evil Twilight Sparkle smacked him in his snout and it hurt the fox a lot. "What's the note say, fox boy!?" Evil Twilight shouted at him. Tails was shocked beyond comprehension. "What-- What the heck!? Why are you always trolling me and bullying, EvilTwi!? ...so tired of getting trolled..." Good Twilight smacked her hands on a desk and stood up. "That's ENOUGH, me!" EvilTwi (Evil Twilight) laughed at this display of unchecked arrogance. "Tch," she said, letting the fox's shirt go so he could fall down and get hurt a little more. "This isn't over, orange fox." Tails sniffled a tear away and wipe the dust off his shirt and second tail. He made his way to the front of the classroom again.

"Guys!" he said, before noticing an angry glare from Haruhi Suzumiya and Cream the Rabbit. "...and Girls!" The girls smiled. "Today Mrs. Frizzle is out for being sick, so and such I have been selected to teach our class instead of her after all I am her favorite, she said as much in a letter I read earlier." The class groaned, because as we all know high school can be a real drag. They didn't want to have class. Tails knew this because he is also a student, so he said "But... I have a plan to make class much more interesting..." Tails looked at Tifa's wet mouth and realized this might be the big day, finally! He jumped back down onto the floor, using his tails to slow his descent so he wouldn't hurt his ankle and started to think.

"Should I do it? I could finally make it sweet with my #1 girl... I've wanted this for so long it almost hurts. Then he talked." "Tifa!" he shouted. The girl perked up. "It's pronounced Tifa," she said, annoyed and then rolled her eyes. "I knew that," said Tails. "Now, please come up here, because we are going to teach the class a very important lesson, so please be my volunteer." *Tifa sighs* "Okay, Tails." As Tifa stood up she thought things to herself. Here are some of them: "Tails is finally talking to me...! I can't believe it after all these years on crushing on him he wants to talk to me! This is a dream come true, but I can't ever let him know how much I like him because things might get super akward for him and I wouldn't want that for him..." She got up to the front of the classroom and looked at her classmates and bowed. "I'm Tifa," she said, proud of herself for not being very nervous. "That'll change soon enough," Tails thought. Soon she might be very nervous...

WHA-KRAAAAANG!!! Tails whipped a table across the room and it smacked into the door so hard it locked shut. Tifa was scared just now, but also slightly allured by this display of raw power Tails did. "Today's lesson is a follow up to the last lesson we learned yesterday. We are going to skip the chapter on something about the woman's blood type causing it to view the fetus as a foreign object and attack a fetus and move right on to how sex works." Tifa's heart and vagina began to flutter. Tails continued talking."Sex happens when a man and a woman love each other very much or are bored and find each other to be hot and such." Tails said, reciting the rules of sex his older brother Sonic taught him many moons ago. "For example, if I..." The blue-eyed fox looked at the brown-eyed girl and stummered. "L-liked T-T-Tifa here, and wanted to... Um..." Tifa smiled then averted her gaze to hide her blushing. Tails smirked. "Heh. If I liked Tifa here and wanted to have sex with her, what would I do, class?"

Mario and Peach held hands and replied together. "You would have sex with her!" The good kids in the class laughed, but the bad kids were texting on their I-Phone 5 and being rude and ignoring Tails. Tails smirked but continued. "Very funny, but how would I go about doing that?" He asked. Mario cleared his throat. "Ahem." Then he (Mario) replied. "You would start by making her feel welcome." "Very good, Mario!" Tails said, as he looked into Tifa's brown orbs.

Tifa smiled as Tails held her hand. She wondered why he always wore gloves, but remembered that it didn't really matter. "Tifa, my dear..." Tails started. "I've liked you for a long time now, y'know?" Tifa smiled even more and replied. "I know the feeling." "Ever since we had that first class together in the fur-st grade," he started, petting his fur and smiling about the inside joke. "I knew you were the one, because we always get along." Tifa started talking back. "I know that feeling too. I've loved you ever since I realized you liked me and that you weren't just after my body like every other boy back then. Now that I'm a fully developed woman, I feel that I know what is best, and..." She looked at him... "That's you, Tails." Tails' heart melted and he knew this was right.

"So... What should I do next, class?" The class was busy staring and biting their nails at the show unfolding like a sudoku in front of them. But then GoodTwi piped up. "...You should both undress." Tifa was shocked. "In front of everyone!?" Tails reassured her. "It'll be okay." Tifa felt better. "Okay then."

Tails began by tearing off Tifa's shirt and the other things on her upper torso. This shocked her, but she was okay after a second. She returned the favor by casting "Firaga" (costing her 52 MP) on Tails' shirt. It burned up but he was fine, but definitely scared, and "hot" in more way than one! Tails felt his penis begin to poke out of his pouch. It felt good. Tails liked the sight of Tifa's curvy tit inside the bra, and languished knowing it would be an eternity until he could see the contents of said bra in their uninterrupted glory. Tifa meanwhile looked at Tails' pecs and abs, and felt herself begin to get adrenaline and hormones make her dizzy. She took over and pulled Tails' pants off, and now he was standing in only his underwear, his shaft delicately hidden from view.

While Tails reeled from the shock of her suddenly taking charge, Tifa slipped off her belt-covered pants and her other stuff, and was now standing in front of a boy in only her underwear asking him to love her. They were both in their underwears. Tifa was blushing, but didn't care that Tails could see it, as he was also blushing. The bulb in his pants became a little more pronounced, but he felt nervous as the entire class was still staring intently. He cleared his throat. "Ahem." Then he stumbled his way through a sentance. "So, uh... Wh- what do you think we should do next, class?"

Haruhi Suzumiya spoke up. Normally she was sarcastic and annoying, but something about this was intriguing her to her core. She was polite and demure as she answered. "Now... you do it, fox boy." Tails smiled, surprised, before nooding his head. Haruhi nooded back. He returned his gaze to Tifa, who was holding him down. "You ready?" He asked his soon-to-be lover. "You know it. Make me yours." This was the happiest Tails would ever be.

Tifa pulled Tails up into a deep, passionate kiss. This being their first kiss, respectively, they were a little sloppy. Some spit got around parts of their faces and it would have grossed them out, but they were too interested in each other to notice it on themselves, so instead they noticed it on each other. Their tongues swirled and danced an ancient dance, and their hearts beat faster as a result of this newfound sensation. Tails had never felt anything like this before. Tifa had. After what seemed like an eternity (in a good way,) they parted lips, gasping for air. "Wow," Tails said, sucking in much-needed oxygen. "I'm definitely not getting Trolled now..." "Yeah... wow," replied Tifa, already feeling at one with her fox soul mate.

Tails's penis started to make an erection in it's pants. He was so worried that Tifa would notice that he got embarrassed, but he got over it because they were going to have sex soon. Tifa stuck her right hand inside his trousers and cupped his shaft with four of her delicate fingers and her delicate thumb. Tails groaned in lust as this happened. Tifa smirked and looked Tails in the eye, but his eyes were closed and she felt satisfied she was making him feel good, so she looked down back at his groin and began to move her right hand up and down on his penis.

Tails felt better than he did before, as the heat from her hand was dissipating into his cock-hard member. His boy part was getting warmer by the touch every second and it felt soo good. The heat was starting to get to him as he was now becoming endrenched in passion sweat. "Ugh, it's so hot, let me just... take this off," he said, taking his underwear off. Now he was standing straight up in front of Tifa in his completely nude glory. "And I wouldn't have it any other way," said the young eco-terrorist. Then she started to lick it.

Tifa licked the penis so much and made swirly motions with her tongue over his tiny hole. This drove him wild beyond infinity, and he couldn't handle it. "You keep that up and I'm going to erupt," Tails said, aroused. "Please stop."

Tifa stopped and complained. She said this: "But Tails, I want to make you feel good, I don't mind if I chafe my uvula on your sexual fuckbeef!" She returned to her ministrations she was doing with her hands. She jerked him off up and down, up and down, up and down. He liked it. Then she went to the left a little and Tails shot white-hot cum everywhere on her hand. "Oh, Mobius!" Tails said, as his penis spilled seed on the shabby hand of his lover and the young friend of his (I am talking about Tifa.)

Tifa scoffed, and threw him across the room. WHAM! Tails hit the back of his head on the metal chalk holder thing at the bottom of the chalkboard, which is the kind with the 3 grooves so you can hold chalk, or even a marker (however markers are too wide to fit in each individual groove, but you can keep 2 in one vertical section if you put them on the first and third groove, the middle groove can still hold a piece of chalk if you are pressed for space.). He felt his vision get blurry and asked what the point was of this attack. "Who's Mobius!?" Tifa asked, furious. "I'm curious!"

"Mobius is just the name of my Home World," Tails said, massaging the tender part of his head, as well as the tender tip of his penis, both at one same time. "For example, your Homeworld is called Midgar, which is part of the Omniworld that we all live in. For another example, Mario and his friends like Peach, Luigi and such, live in the Mushroomverse, which is also part of the Omniworld. We travel between our worlds with portals that we travel through at times of crisis. For the last example, that bastard Cream the Rabbit lives in a world whose darkness you cannot picture, whose horrors cannot be adequately described with words, and where the tiniest shred of hesitant innocence spells certain doom for any inhabitant unlucky enough to be cursed with the burden of goodness. It is a vile place," he said, before speaking up to address the rest of the class, "which I hope none of you ever have to experience." Cream looked sad. "I'm sorry, Cream, for everything you've been put through. You deserve so much better. You really do."

"Oh," said Tifa, before she was unable to talk any longer as she started to suck on Tails's rock-hard member. "Ung!" said Tails, who felt nice being stimulated in this manner. Tifa then positioned herself above Tails' stark dickrod. "Are you ready for this?" asked Tails, worried about Tifa feeling pain from her hymen being corrupted. "I think so," she replied, smiling into his eyes. "It's gonna hurt if you haven't already ruptured it to pieces while masturbating and such."

"Believe me this has been taken care of, and now it's my turn to take care of you," said Tifa, as she let gravity take her, and Tails' stupendous wiener slipped right into Tifa's femslit unabated and unchallenged. "Ammmm!!" said Tifa, unable to form a coherent ululation, much less an actual English sentence. "Fuuuuuuuck! My vagina feels excellent!"

Tails felt the wet wall in Tifa's respective self push against each side of his boyhood - or "fox boy" hood, as Haruhi would say. Tails chuckled as he looked at Haruhi and winked. Haruhi waved hello and winked back before returning to a nail-biting pose. She was as tittilated as could be. She was also confused as to why Tails just winked at her. She wondered if Tails harbored feelings, but decided to wait to bring it up until he was done having sex with a different girl right now.

Tifa began to slide herself up and down the stiff fleshpole she was currently a-straddlin'. "Ungh! Huunngh! Hyeah!" were some of the vocalizations she was emitting each time she impaled herself on Tails' love-salve-coated bulb. "Goddamn it! Fuck me so much! Ayyyyyy!" Tails couldn't believe the feeling of her squeezing on his balls, which is what she started doing just now. He liked it so much but he asked her to stop.

"Please stop, I don't want you to squeeze make the rest of my cum squirt out!" Tails said, flicking his kegel muscle and thinking about medical procedures to stave off his stiff staff. "Ow!" Tifa got worried and spun around to get on her hands and feet like a horse or dog, and then said to fuck her dog style. Tails obliged and decided to treat her and call her dog names like a dog.

"What's that, bitch? (female dog) You want me to fuck you raw?" Tails said, lining himself up with her entrance. "Y-yes, please! Fill me up!" Tifa replied, needily waving her rump around as her pap juice dripped out with anticipation. She was eager to have her needs met, and was soo happy that it was Tails about to do the deed. "I'm in heaven right now," she thought, wet. Tails held his breath in anticipation for the penetrate, and then leaned his gravity forward.

The lack of friction was pretty great. Tails thought it felt a lot like a sexier version of what it was like to hold a soap bar and then it falls out of your hand and goes down one end of the tub and goes up the other and does a jump like a skater on a half-pipe. Way sexier, in fact. The heat and pressure of Tifa's runny cunny threatened to burst Tails' dam, which would make his vulpine seed flood her womb parts. She coughed while he pumped in and out, and the sudden addition of pressure felt like she was trying to crush a diamond with that thing! Tails felt pressure build inside his testis and he realized he wasn't going to be able to take it any longer. He pulled his slab out so he wouldn't cummed on top of her vagina. The pressure was released as he shouted her name. "Tifa Lockhart!! I love you!!!!"

A thick rope of cum zapped out of his winking hole at a constant angular velocity (for those of you who don't know, this is the way a NERF disc spins.) It smacked Tifa in the face and made her really hornier than she'd already been, and she was already incredibly horny. She wiped the spern cells off her face as fast as colony collapse disorder wipes out a stable population of bees and licked it up, lapped it up like a doggie laps up its water bowl - she couldn't get enough - little sex puppy. She liked this cum and wanted to return the favor. She tackled Tails to the ground and placed her pussy on top of his mouth. He couldn't talk, but she could, so she said this: "Your turn, make me cum like nobody has before!" Nobody had before. This confused everyone.

Tails stuck his tongue muscle onto her clitoral door. He opened the folds gently and he began engaging in a dance as old as destiny. He licked the nub like a lollipop and her face made such a cute orgasm-cusp face that I maybe couldnt believe it. Tifa was flipping out over here. It felt so good she was scared she was going to cum too fast before he got to feel satisfied with himself. His oral angling got her twitter-pated a lot and!

Tails got tired as a fox and withdrew his tounge from her clut. She groaned in frustration. Tails looked up and made a face of similar frustration. Then he told her to lay back because he was going to make her feel so good. "I'm going to pound you like a veal, honey. Get ready." Tifa squealed in fangirlish excitement.

Tails lined his penis up with the vagina of Tifa, and she was so sopping wet it wasn't even funny. Tails slid inside and Tifa's warm walls were squishing on him. Her tightness was incomparable as Tails didn't have a very good sample size for comparison. As he pumped in and out Tifa made squeaking noises of happiness as she couldn't believe this was finally happening. "Finally- ah! We're finally- oh!! Finally together as close as can-- fuck! Close as we can be!" Anything more she would try to say would be punctuated with involuntary utterances of sexuality so she stopped trying but Tails said, "I know what you mean baby, I'm on fire right now." He pointed to where they were entwined and smiled and so did Tifa.

Tails felt himself begin to want to cum, because of the sex. Tifa felt similarly, except about herself, but she was pretty sure Tails was also close because of the Sexy Expression on His Face. "I'm gonna pop, girl, where do you want it, homie?" Tails asked. Tifa said in a moment of immature thoughtlessness, "Inside, baby, spray my walls like you're trying to PAINT the place a lighter hue!" Tails didn't need to hear anything else. With a final push he erupted, coating Tifa's innards with his foxy seed. He had never felt something feel so right before this. Tifa squirted. Spent, the two young lovers collapsed onto the tile floor and looked into each other's eyes.

"I love you, Tails the fox," said Tifa, starting her speech. She held her stomach. "I am now honoured to be carrying your baby. For years I have been wanting you and now it has happened and I couldn't be happier. I want to be with you forever, Tails, and as such I am prepared to move in with you house-wise. If you're up for it, she joked, motioning to her semen stained vagina. I know it's early because we are so young but we get along so good that it has to be a fate older than destiny." Tails smiled into her eyes and couldn't believe his luck. Maybe he should try playing Poker later, and get a Royal Flush in the most Lucky Way and win a Real Jackpot on top of this jackpot of love.

Tails began to reply. He choked a tear and then went, "Tifa, I know that I just shot a wad of spern deep within your mossy tunnel, but we should take it slow at first. But I definitely love you and yes you should move in, because that would make it easy to fall asleep with you in my arms and then wake up for morning sex. Then we could--"

"AAAAHHHHHH!" Tifa shrieked! "WHAT TIME IS IT?!" Tails looked up at the clock and tried to answer but she read it faster. "I'M LATE! GOD DAMMIT, TAILS!" Tifa stood up and wiped herself off, front to back and then put her clothes on in an angry huff. "Dammit, tails, you made me late for practice with your long fucking speech. I knew this would happen, I should have listened to my mother, but NO, I'M TIFA, I'm SO MATURE and I know EXACTLY HOW TO LIVE LIFE. Jesus Christ."

Tails tried to get a word in edge-wise, but failed. He just held his arm out attempting to reach out to his lover, but she recoiled at his touch. "Don't," she said, sternly. "I have to go."

"Will I see you later?" Tails asked, with sorrow in both of his eyes. "After all, I love you."

Tifa opened the door and stepped through it, but looked back before leaving. "I doubt it, Tails the Fox. I really do." She turned with angry and shut the door behind her, leaving Tails alone to wonder where it all went wrong.

"Welp," Haruhi started, "This is awkward." The class agreed and filed out of the room one by one. The evil kids didn't even talk shit on Tails until they were outside his ear shot. It was THAT BAD. Good Twilight Sparkle stopped before leaving as she was last.

"If... if you need to talk to someone," she said, looking at Tails who was looking at the stains on the ground, "I'm around." Tails looked back at her and smiled. She smiled back and quietly closed the door behind her. Tails started to put his clothes back on in silence.

After a few minutes, Tails emerged the classroom to a thousand judgmental gazes from his classmates of this year. They were looking at him like some kind of pig, but he was a fox. Haruhi piped up. "So, what's up, fox boy? I mean, are you okay was what I meant to say!" Tails just looked downwards down.

"I'm sad," came his pregnant reply. He turned tail and walked away from his friends and enemies but not his problems, because your problems follow you no matter where you go they never get further away like the dots I see when I get mad. Sometimes the floaties in my eyes get angry and change shape into scarier shapes as well. The doctor says I am making this up but I am not making it up. Just because I make some stuff up does not make me some kind of liar. Anyway, Tails was halfway home because he just passed the park with the swing set.

Tails realized his life was over and decided he had to ask someone for help before it was too late to do that. He remembered what Good Twilight said earlier and decided to make a detour to her house. "Well, it won't really be a detour because I have to turn around since it's the other way, but I guess it's a stop on the trip from school to home, so it's sort of a detour if you think about it that way." Tails turned around and turned on his phone and typed in the address for directions.

Twilight was in her house working on a computer. She was doing something really super complex like coding a app. Than as soon as she was in The Zone, the doorbell knocked and Tails started talking. "Who could that be at the door?" Asked Twilight, getting off her ergonomic chair.

She got downstairs and opened the door to catch the end of Tails' rant. "-acting like some damn kind of troll or something, I mean REALLY!" Tails inhaled and stared at Twilight.

"Hi, Tails," came her reply. "I guess you're still mad, huh?"

"Yeah, today was one of the worst days. Like, one of the top three worst, jockeying for first place against Seinor Prom and the day Sonic told me the Rules of Sex and made me so scared of doing the wrong thing like showing off my baseball card collection. That was such a bad day."

Twilight sighed and said, "Well you're having a bad day due to stress, I can try to help as I have a history of helping my friends through their problems. " She motioned Tails into the house, then laughed to herself and closed the door.

As they made their way up the stairs, Tails admired the many pictures of horses adorning the walls. "Great drawings, Twi. You do these?"

Twilight looked back in confusion. "Drawings? What drawings?" Tails pointed at one, of a yellow horse that looked particularly shy. The horse also had pink hair and what looked like wings.

Twilight chuckled. "Those aren't drawings."

"What? What do you mean?"

"Don't worry about it. We're almost there." They continued upstairs and entered her room. Tails took in the sights.

"Whoa," he said, "Nice room."

"Thanks. I worked hard to get it," she replied. "The walls are painted in my favourite color, purple, and it has a swirly pattern which I like so much. I also have a lot of books as you can see in my bookcase and I read a lot as well." Tails agreed silently and sat down for a makeshift therapy session.

"So what seems to be the problem, Tail?" Twilight said, putting on her cuter glasses, which unfortunately weren't the right prescription any more, but it helped complete the "Therapist" look. Tails appreciated this extra work. His ear twitched as he thought something.

"Tail?" He asked, quizzically.

"It's a shortening of 'Tails.' Because often people will shorten their friends' names as a sign of disrespect to the parent. For example, you call me Twi. That's the first syllable of 'Twilight Sparkle.'"

"Oh yeah," Tails said, leaning back on the chair trying to look cool instead of nervous, as he noticed Twilight's beautiful rack through her shirt because in this very sensual light of her bedroom it made her clothes transmit a great deal of light and you could see what was behind the fabric and in this case it was a dainty purple bra and perfect boobs under it. "Wow," he muttered to himself.

"Wow indeed," Twilight said, smirking. She saw a little bump erecting on his pant and thought it very good indeed. She felt herself waver and began to have the impure thoughts but stopped them in order to help Tails with what ailed him so. She cleared her throat. "Ahem. So what's making you hard?" she asked.

Tails sat up in shock. "What?!" He looked down and noticed a penis making a little too much of it's presence known! He pushed it back down and it was okay though. He looked back up from the penis to Twilight and said, "What do you mean, making me hard!?"

"I meant making your life hard," she said, covering for the slap-up.

"Oh. It's Tifa."

"What's wrong?"

"We're going through a rough patch after I had an orgasm inside her sex."

"I can feel that in your aura."

"Thank you. Well basically I just feel like she doesn't appreciate me. It's already been, like, a hour since I deflowered her hidey hole, and she won't return my calls or anything. How do I know when the spark is gone, Twi?"

Twilight leaned forward to answer, but then didn't. This is because she realized she wasn't actually paying attention to the fox's woes as she was letting herself get twitter-patted thinking about this vulnerable boy in front of her. Oh, the things she could do with him. You know, being a single and lonely woman who can do magic isn't all bad, as you can use the magic for stimulation and such. But nothing compares to the touch of a Real Lover, unless you knew the right spells, which Twilight doesn't. "The spark may not be gone, it may have just moved to another indivisual," she said, snapping her fingers and making a spark happen.

Tails smirked realizing what the Twilight was hinting on. "Oh," he said aloud, "I see what this is." He pushed the candle off her desk and was now looking for the right opening. "This is some kind of sex thing, right?"

She hesitated for a moment. She had only had sex with a fox once before. She inhaled and answered, "You know it!" She pulled off her bra and shirt and started to straddle Tails, who was very surprised but not angry about this. Tails stood up and bumped into Twilight because she was straddling him! It was awkward, but pretty funny a moment of a moment for the two. Tails took off his glasses and toss them aside. Twilight knew what this meant. She followed suit by kicking off her socks and making a nice love nest on the bed, because the floor just wasn't as romantic.

Once Twilight finished fluffing the pillows, the job fell to her to begin fluffing Tails' softening board. She grabbed it and made him grump. The list got to his head and he pulled her hair some. "Ow! What the hell," she asked, wincing. "That's my hair."

Tails smirked. "I know, now here's mine." He used one of his tails to smack her asshole and it made her driven wild. She was ready to try anything with this adventurous fox. Wow! Twilight took off her pieces of clothing one by one to twittilate the fox. It worked.

Tails also did something similar, but seeing as he really only ever wears shoes, there is not a lot of sexual tension that can be built and SHATTERED like a Jenga Tower! He unlaced his shoes and stared Twilight deep in the eye, making sure to smirk as he did a fell swoop and the laces draped across the nose of his other shoe. Twilight was impressed by this show of dexterity, as she was mostly focused on his fingers, which would soon be plunged into the wet portal she considered so dear to herself.

Tails then put his fingers on Twilight's face and made out with it. Their savliva mixed and swirled along with their tongues, which also swirled. What was going on here was a meeting of the minds, and of the bodies. Twilight felt Tails breathe into her mouth and it tickled her fancy, this idea of sharing air together. She tried to sync up her breathing with Tails' but it never worked, she got the phasing exactly backwards and so they ended up breathing into each other at the same time and making a funny blowfish-face during the kiss. Eventually the kissing stopped and the fingerblasting begun.

Twilight grabbed Tails and stuck her gloved hand into his anal passage. She felt around for awhile until she found the prostate gland, and she started massaging it. Tails noticed this and was shocked, and returned the favor. Tails ran his finger up and down and all around Twilight's prostate gland, making her squeal with the delight. She was about to cum when he removed his hand and cleaned it so the next part would be sanitary. She pulled her hands out of Tails and grabbed onto the bed to prepare for the onslaught of pleasure Tails was about to engorge her with.

Tails licked her pussy spot and made circles with his muscle on her sensual folds. He made the journey to the nub at the top of her labial zone and then attacked it with fervor and lust. Twilight was contorting her pelvis and felt the orgasmic feelings start to pool in the lower part of her core. Tails felt cool for doing such a good job, so he kept doing it. Twilight released a guttural howl and a grunt and an orgasm made her lose all control. She ejaculated a little on Tails, who backed off in surprise and made a troll face. This made Twilight laugh, which hurt her a little because she was still mid-orgasm and that's a bad time to laugh because of the muscle contractions going on. Tails wiped his face on Twilight's bedspread, which he noticed curiously had pictures of the same 6 horses from the stairwell on it. Twilight fell back down on the bed, spent, and sighed sweetly.

Tails decided to pop the question. "What's the deal with all these horse pictures?" he asked, unaware. Twilight finished her cum and sighed, wondering how she'd explain all this.

"Well, it's a long story," she started, while circling her fingers around her core. She eyed Tails with her sultry gaze and continued, as he stood up with his dick out. "I'm not actually from this world. I'm from a magical land called Equestria."

"Equestria?" Tails replied. "When's that?"

"It's not a question of when, so much as where."

Tails was confused as he penetrated Twilight, her warm walls squeezing his member. "What do you mean, where?" He asked, pumping in and out.

"Equestria is on an island that humans now believe to be deserted and uninhabitable."

"Why did you come here? Was something wrong with Equestria?"

Twilight grunted as Tails poked her cervix. "No, not exactly."

"Then what?"

"There's something wrong with... me."

Tails stopped pumping in and out, in and out, he was buried to the hilt and grabbed her face with both hands. This was an awkward position, but the pressure felt good on the vagina. "What do you mean? Tell me everything."

Twilight inhaled, exhaled, inhaled again, then started talking. "I'm... rather, I was... a horse. I lived in Equestria with all of my friends, in a lovely town called Ponyville. We had adventures, and helped each other grow, and things were just... Celestia, they were just perfect."

"What went wrong?"

"I... I did something bad. Something that had been frowned upon for thousands of years by Equestrians. Something... pervy and such."

Tails was intently listening as he softened.

"Thousands of years ago, long before I was ever born, as I am the tender legal age of 19 in Human Time, Equestria wasn't just filled with ponies and other magical creatures. Humans were also part of our civilization. Humans and ponies got along famously. They worked together, ate together, made jokes together... everything."

Tails sighed and began to fuck her again as he was getting bored.

"But over time, Humans grew overzealous with their ideas of how ponies and humans should work together. It started innocently enough, with ponies giving humans rides, helping pull carts, stuff like that. But humans weren't satisfied with that. Soon our world was fraught with classism and shit. Humans rode ponies, made them live in barns, wouldn't address them by name or speak to them in normal English."

Tails was sweating profusely as Twilight used her magic to form a magic dildo that went in his butt and added a much-needed stimulus to the Prostate. He felt awesome and thought about the doctor so he wouldn't cum so prematurely there.

"It all came to a head, when the current ruler of Equestria, Princess Celestia, was entered into a pony show."

"A pony show?"

"Yeah, it's kind of... it's like a contest, where humans paraded their horses around like some kind of sick toy. Like we were their pets. But even that was begrudgingly accepted, until Celestia, with her powerful magic and revolutionary ideals, was figged."

"Figged?"

"Figging is the practice of inserting a piece of ginger root into the anus, vagina, or male urethra. The ginger, skinned and often carved into the shape of a butt plug, causes an intense burning sensation and discomfort to the subject. Ginger is an irritant, and when administered to a horse, the horse will carry its tail high and generally act somewhat restless and more lively. The purpose was often to make an older horse behave like one that was younger, or to temporarily liven up a sick or weakened animal."

"Why would you even fig a young horse," Tails asked, as he shut his eyes in ecstasy and his seed lurched forward out of his dick, filling Twilight's every want and desire, as well as literally filling her pussy with a cumstorm of passion.

"That was the problem. Almost everypony was used to the mistreatment of ponies, but Celestia wasn't going to stand there and take a piece of ginger root in her fundament. She violently kicked the man who was about to place the ginger root inside her anal passage, and shouted to the others to do the same. Unfortunately for the humans, they listened. What followed was a full-on class war, ponies versus humans. If Celestia had had an angried color to her aura, she might have just killed every human in Equestria."

"So what did she do instead?"

"She banished them. Every single human was teleported out of Equestria, and dumped out in what you now call Scotland. Human became a bad word, something you couldn't mention under penalty of death. Celestia figured humans did nothing but bring ponykind down, and wanted nobody who hadn't experienced them firsthand to ever learn about the atrocities that went down."

Tails wiped his cum off the small of Twilight's back with his left tail. "I don't understand, what does that have to do with you?" he asked, preparing to fuck her so sexually once more.

"Well... I figged."

"What?"

"I... figged. For the pleasure."

"What do you mean?"

"...it's my greatest shame. When I was a filly, I got into sexual activities of the experimental nature. But the worst it got was when I found a centuries-old underground book called 'The Depraved Things Desperate Housemares Get Up To," which detailed figging in detail. I couldn't believe it, reading the stories inside tittilated me and everything. But when I finally gathered the courage to try it..."

"What happened?"

"My old best friend, a baby dragon called Spike... he walked in on me. He betrayed me. Or maybe I betrayed him. He sent a letter telling Princess Celestia, and within seconds she landed at my front door, glowering with hatred and disappointment."

"Did she hurt you?" he asked, while experimenting a little with her anus.

"No. Not physically. She stormed inside and slammed the door shut, smacked the ginger root out of my plothole, grabbed the book and burned it in front of my eyes. She explained everything about humans and ponies, and by the end I was crying, I was so scared... I'd never been scared of Celestia before. I didn't know what to do, I was just... cowering. Just... blubbering like a fool. I thought she was going to kill me. I certainly think she wanted to."

"Why do you think she didn't kill you?" he asked, concerned and fucking her dainty tits.

"I made a deal with her. I promised to leave, to banish myself. I couldn't make things right if I stayed there, because the... *sob.* The hurt in her eyes was so... real. I'd never felt worse about anything, because I was her most faithful student, her... most trusted student. And she was the mother and sister I never had. When I was young, we did everything together. And now I had hurt her in the worst way possible, short of murdering her, which wouldn't work because she's an alicorn, and has extreme levels of magic."

"I see," Tails said, having a frankly wonderful time with her pretty little clitty.

"I told her I'd leave, I'd just... leave. She didn't respond. She wouldn't look at me, she didn't even say goodbye. She just walked back outside, slammed the door one last time, and flew back to Canterlot. I couldn't believe it. I looked at a picture of my friends and wondered if I had time to at least say goodbye to them. Spike held my hoof with his claw and... Celestia, he looked so sorry. I knew he didn't mean for all this to happen. I forgave him, because he was the closest thing to a son I've ever had. He didn't deserve to blame himself. Choking back tears, he promised me he'd tell my friends... my very best friends, why I had disappeared. I thanked him, gave him a kiss on the nose and opened a portal and went in."

She pointed at a barren patch of dirt in the middle of a small field outside her window. "When I came to, I was in the field right out there. I turned myself into a human and made this house here."

"Oh," Tails said, masturbating furiously as Twilight wasn't really into it any more, but he still had some gas in the tank. "That sucks. But that doesn't explain why you have pictures of these horses. I'm assuming they're your friends you mentioned?"

Twilight grabbed his cock and helped him jerk off. "Oh! Yes. I took those, they're actually pictures. I go back once a week to hang out with them. That's why I'm never available on Saturdays."

"I thought you had swim team," Tails said, surprised.

"I made it up. We don't have a pool at school!" Twilight chuckled the sentence out.

"How are you able to go back and forth so easily? Doesn't Celestio get angry?"

"It's CelestiA, and no, she realized she really overreacted, and forgave me. Things are a little awkward when they bring out the traditional ginger carvings of her at the Royal Dinner, but other than that, you know. Back to normal."

"Well that all makes sense now. Thank you," he said, shooting a load right down her slut throat.

She coughed some of the seed up, but swalled it back down like a good, bad girl. She got on her computer and said, "Sorry for boring you with that, based on my Nike+ FuelBand readings, my pulse really dropped towards the middle there, so I guess you lost interest for a little."

"Yea, but it's okay, you were getting emotional and I don't want to interrupt your feels."

They sat in silence together for a while, admiring the way their juices were mixing. When the stream of Twilight's essence hit a drop of Tails', they smiled and kissed one another. While Tails was looking at Twilight's eyes, he realized something, and jumped out of bed, getting some cum all over the place, making Twilight mad, but she did magic and cleaned it up. "What is it!?" She asked, in her full voluptuous nude glory.

"I've got it!" He shouted, smiling so wide it's rediculous. He grabbed Twilight by the shoulders and yelled right at her face, "A portal!"

"A portal?" she asked, concerned for Tails' mental well-being.

"I hate my life here, and Tifa will never talk to me again... Why should I bother staying!? Twilight, can you send something ELSE through The Portal? Besides yourself?"

"Well, yeah, that's how I got my camera through to print the pictures of my friends."

"Brilliant! Put me through!"

"Are you sure? I won't be able to bring you back. Well, not until I visit next, which will be on Saturday, a full 5 days from now. Equestria can be a dangerous place if you try to go it alone. I suggest you try to make friends if you're serious about this."

"I am serious, let's do it."

"Oh Tails," Twilight said, winking. She pulled her magic horn out of her purse. "We just did!" She twirled around and cast the magic spell. "Facere parum pudici porta!"

A bright purple spark shot out of her wand and flew to the center of the field outside. There, it stopped, and a swirling vortex opened up in the air, also bright purple in color. "What the fuck, Twilight?" Tails asked. "Why is it all the way out there?"

"I don't want the gusts of temporal wind to mess up my room, so I put it out there, where I first arrived here. It's where I always put it, please chill out!" she replied, huffing and puffing. "Let's go." Twilight set off down the stairs, and Tails followed after lacing his shoes back up.

On the staircase, he eyed the pictures more carefully, now aware of where they came from origin-wise. His eyes lingered on a picture of a pink horse. "There's something about her," he thought to himself. Twilight snapped her fingers, snap snapping Tails out of his thoughtful stupor. "Oh! Sorry," he said, hurrying down the remainder of the staircase.

They emerged outside to the sun-drenched field and everything was beautiful. Tails asked, "Was there something about that pink horse familiar to you?"

"Well, yes," Twilight responded. "She's one of my best friends. Why?"

"Oh, I meant to me. Something about her felt familiar to me, I think."

"Oh. Okay," she said, before setting up the ladder. "Stand on this, and once you're ready, I'll hoist you up."

"I have Tails, you know. I can just fly."

"It'll be safer this way. You don't want to lose a tail, which is a very real danger, doubly twice because you've got the two tails." Tails felt his tails and cringed at the idea of one being cut off. Holding Twilight's hand, He ascended the ladder, before looking back down, very nervous.

"What if I don't make it?"

"You will, I do it every week. It isn't that big of a deal."

"Oh." With that, Tails gave her the signal, and Twilight pushed him up into the portal. As the winds surrounded him and the light enveloped him, he faintly heard Twilight shout something.

"By the way! The portal's going to change you a little bit! Don't be alarmed! I'll see you soon, Tails the Fox!" She disappeared from view as did the sounds of her heart-sweet voice. Tails tried to right himself in the dimensionless wormhole, but to no avail. Up was down and right was wrong in this confusing realm. But soon he saw a light at the other end, and tried to make his way towards it. Swimming closer and closer in the waves of the infinite, he started to feel his arms and his legs become numb. He tried to look at them, but the light began rocketing towards him and by the time he knew what was happening, he suddenly felt gravity pulling on him once again.

The pink horse shot a beautiful smile at the former fox, and he stummered as he gathered his thoughts to reply.

"I'm... Miles. Miles Prower. My friends call me Tails." He waved his 2 tail tails a little. "You can guess why." He looked to the sky and closed his eyes to focus on the chain of events. "I had to leave my world, because things got soo awkward with the love of my life, Tifa." Pinkie's expression saddened the smallest, subtlest bit. She was hoping this sexy fox would be single. His cheekbones were sharp enough to cut a razor on! "I was sent here by the Twilight after she took me into herself and gave me advice about this stuff." Pinkie laughed.

"Twilight! That old mare? I haven't heard from her in so long! How is she?"

"She's fine, but sad she had to leave after... you know what," said Tails.

"Ohh... we don't talk about That out loud very often, but when we do, we call it The Storm" said Pinkie, quietly. She moved in much closer to Tails and whispered, "It's forbiiiiiddeeeeeeen." Tails nodded his head, then looked around himself trying to ascertaint his whereabout.

"Where am I?" He asked, puzzled as he was. Pinkie's loud response was not what he was prepared for.

"You're in the Everfree Forest! But you should come with me back to town, this place gets spoooooky at night!" She punctuated the word "spooky" by waving her hooves in a manner approximating the movement of a ghost. Tails looked around and realized he didn't have much choice. He decided to follow her. Maybe this girl could be useful. She had a radiant beauty and carefree smile that, as bad as today had been, brightened Tails' outlook. She noticed him staring at her eyes and giggled. Tails looked away in embarrassment having been noticed. Why was he feeling nervous? Was it this new body? This unknown world? Or is there just something special about this girl? Maybe she would become more than just useful.