Sleepless in the Saddle
Twilight Sparkle was tired.
It was late at night and she couldn't get to sleep for the life of her. Even though her eyelids were heavy and her body was exhausted from a day of frolicking and playing with friends, she couldn't sleep. The summer night was making her bedroom just a little too hot for comfort, Spike was snoring just a little too loudly, and Owlicious was just staring at her through it all.
Creeper.
Twilight groaned to herself. She had trouble sleeping more often recently. In fact, it had become a regular occurrence, ever since she had let Rarity talk her into stopping her habit of late night study sessions. Twilight had let her friend convince her that she needed to have more energy during the day to have fun and she couldn’t do that if she spent hours in bed before sleep with her nose buried in a book. She had decided that having fun with her friends was one of her chief duties now that she was a Princess. The way she saw it, having fun with her friends was probably the most important duty of the newly minted Princess of Friendship.
Even so, old habits die hard and she was still getting used to going to sleep at a reasonable time. For several hours Twilight's mind wandered about, thinking about how she would spend the coming day with her friends and what she could do with them. She thought about what she would eat for breakfast at Sugar Cube Corner when she woke up, her afternoon flying lessons with Rainbow Dash, getting a new dress made from Rarity, and anything else she that might strike her fancy during the day. Twilight had made a promise to herself to try out as many new things as possible now that she was a Princess. Honestly it had all begun to excite her about tomorrow making it still harder to get to sleep.
After spending a fair amount of time rolling about in her bed making plans, Twilight wound up realizing that her thoughts were only serving to keep her awake.
Ugh, Twilight grunted in her head, which is a rather ridiculous thing to do, I just want to go to sleep already.
Throwing her comforter off of the bed, Twilight hoped that would alleviate the heat that had been keeping her up. Now only under the thin sheets Twilight realized that without the weight of the comforter she would have an even harder time sleeping. She had grown so accustomed to the weight of a comforter on top of her as she slept, that it felt entirely unnatural to try and sleep on a bed without one.
One day, I'll study what kind of magic they make those things with, Twilight thought. There's no way that this is some sort of natural phenomenon!
But sleep continued to elude the purple alicorn and after many minutes of futile tossing and turning she gave up. Twilight slowly made her way out of her bed, deciding that there was no way she was going to rest now, not with thoughts and ideas on how to master the complexities of the magic in her comforter running through her head. She would just get a glass of water and try and cool herself off that way.
It was either that or masturbate.
Since Owlicious was always watching, it meant a trip to the kitchen.
Walking down her steps, Twilight was careful not to make a sound and ensure that she didn't wake up Spike. The baby dragon needed his sleep after all. Creeping into the small kitchen, Twilight poured herself a glass of water from her sink and put a few ice cubes into the glass to chill the drink further.
But Twilight's boredom soon got the better of her and she decided that she might as well just masturbate. Placing her drink untouched on the counter, she began to make her way to the lab in the basement and the locked drawer where she kept her "special toys".
Opening the drawer, Twilight began to look through what she had to work with tonight. Her eyes danced across all of the various tools she had to pleasure herself with, from the "Pokey Pierce", to the "Thunderlane," there were so many choices. As she glanced around her eyes eventually found her favorite toy, which was just what she just felt in the mood for tonight. Licking her lips, Twilight used her magic to lift the piece high into the air.
It was the "Little Macintosh,” though hardly little at all. It was about ten inches long and had good three inches of girth. She had long since magically obtained the proportions for the farmer that was its namesake and it had rapidly become her favorite toy of all.
Twilight knew it wasn't creepy if the two were meant for each other. Big Mac just hadn't realized it yet! Surely he'd leave that floozy school teacher once he figured out who really loved him. Also, Twilight was sure Cheerilee wouldn't mind that the librarian kept a replica of her coltfriend's love-muscle in her home. As long as Cheerilee didn't know about the dildo she couldn't get upset about it. Right? Right.
Licking her lips in anticipation, Twilight placed her forehooves onto a nearby bookshelf and prepared herself for the festivities that night.
But wait! Twilight stopped herself as she levitated the scarlet silicone sexing piece behind her. Maybe I can get the real thing.
Releasing her magical grip on the toy, Twilight began to consider the logistics of her possible penis-quest, the rubberized schlong bouncing unnoticed and unloved off the hardwood floor. In theory Twilight knew that she could seduce Big Macintosh if she could sneak into his room over at Sweet Apple Acres, but that was quite frankly a very big if. Applejack and her family wouldn't take well to Twilight sneaking onto their property to have a lay in the hay with Big Macintosh.
Twilight would need to be as sneaky as possible to avoid any Apples that happened to be up late tonight. She needed some sort of transportation, some sort of way to get from one place to another with minimum hassle, avoiding the prying eyes of Ponyville. Sitting on the floor in contemplation, Twilight felt an involuntary twitch of her wings, and decided to use her newest form of transportation.
Stepping off of her Segway and into the Apple family's house, Twilight noted the fact that the Segway was very convenient, and that stepping off of the Segway and going into the Apple family’s home was in no way a jarring transition.
Plus it had a pleasing hum as it moved her along.
Like for real, she had totally just skipped over everything that she had been worried about before because of the easy handling and quiet maneuverability of the Segway. Buy a Segway today!
Twilight's breath caught in her throat as she approached Big Macintosh's door. How would she go about seducing him? What if he was saving himself for marriage? Could Twilight get Big Macintosh to marry her on such short notice? What if he didn't return her affections? Maybe sneaking into your true love's home to seduce him away from his current marefriend wasn't the best thing to do when you couldn't sleep?
No Twi, you can’t think like that when you’re so close to your goal! Twilight steeled herself as she as she pushed away her doubts. She took a deep breath as she prepared to push open the door. She would have to move hard and fast if she wanted to win Big Macintosh's heart tonight. There wasn't any room for doubts or worries, no time to second guess, and no forgiveness for half-attempts. Twilight had only one attempt to get this right! She stood up a little bit straighter and stronger than she had in quite some time. This was the day that she would take what she wanted.
Twilight was not prepared for what she found and was taken aback when she entered the room.
Big Macintosh was laying back in his bed with one of Applejack’s lassos hanging off the back of his bed and pulled tight under his jaw, a hoof on his thrill drill, and a piece of straw sticking out of his mouth.
Twilight stared for a moment before commenting.
“What are you doing Mac?”
Mac merely looked the Princess of Friendship in the eyes and moved the straw to the other side of his mouth. “Autoerotic asphyxiation.”
“That thing where you choke yourself?”
“Eeyup.”
“Didn't Caramel die doing that last week?”
“Eeyup, but he came buckets.”
“Oh.”
Big Macintosh raised an eyebrow. “Now is there anything I can help you with, or can I get back to what I was doing?”
Twilight would’ve responded quicker had she not been entranced by Big Macintosh’s third leg. It would appear that her measurements for Little Mac were off but a rather hefty amount. Twi could not take her eyes off the thick and meaty pony-flesh as it bounced delicately, almost majestically in Mac’s hoof.
Twilight shook her head quickly to clear her head of such thoughts. She had come here on a mission! She should be tall, proud, even sexy! A Princess of Equestria does not get thrown off course by a mere choking fetish! That’s what Celestia would say!
“Ahem!” It was sort of awkward that Twilight said ‘ahem’ instead of just clearing her throat, but that’s whatever. “I am here to seduce you Big Macintosh! I will not be stopped!” Big Macintosh just continued to stare before moving the straw again.
"Do you mind if I keep the lasso on while we do this?"
Twi deflated a little bit at this. She had thought herself more enticing than a mere piece of rope.
"Is a Princess not enough for you?" she inquired seductively, laying her ears down and trying to do that thing fillies do where they make their eyes go all big and doe-eyed.
Big Macintosh glanced down at his slowly drooping pony piston. "Apparently not."
Twilight’s head fell at this realization. She had always had doubts about her looks, and this just seemed to confirm them all. Even as a Princess she couldn’t win her true love’s affection. Despondent, Twilight walked over to the window and put her fore hooves onto the windowsill. “Oh, isn’t there somepony out there for me?”
As Twilight gazed out of Big Macintosh’s window, she saw the moon begin to light up with magical energy. A voice spoke to her in her head as the silhouette of a face appeared on the moon’s surface.
“Twilight our loyal subject, what seems to be bothering you?”
It was Princess Luna! Here to help Twilight in her hour of need!
“Oh Princess Luna, its awful!” Twilight cried through the window as Big Macintosh continued to stare at her backside. “I’ve never felt more uncomfortable with my body!”
The silhouette on the moon gave a hearty laugh. “Dear Princess Twilight, you mustn’t be so serious about the world. The world, the world is just a game that is behind us dear Princess Twilight,” The Princess of the Night cleared her throat. “And once a princess gets an understanding on the game, and what the levels and the rules of the game are, then the world is not a trick anymore. The world becomes a game to be played.”
Twilight tilted her head at the moon. “That sounded a lot like a Tupac song. Did you just paraphrase Tupac at me? Can you really do that?"
The silhouette glared down at this. “Real princesses do what they wanna do, bitch princesses do only what they can.”
And with that, the silhouette faded away as the sky began to turn brighter. Morning was approaching and Twilight had managed to get neither sleep nor serviced. She reflected that this would go down as her greatest failure to date.
Big Macintosh turned in his bed to face Twilight. “So are we bucking or what?”
Twilight jumped at the reminder of who’s room she was in. Her heart leapt in her chest. Maybe tonight wouldn’t be a complete failure after all. She turned and gave Big Mac what she hoped was a seductive grin, not one tinged by sleep-deprived desperation.
“I reckon we have a few minutes o’ darkness left, enough for a quick one if we hurry,” the purple Princess purred as she leaned further against the windowsill lifting her tail and presenting her Cave of Harmony™ to the large earth pony.
Twilight could barely contain her excitement as Big Macintosh slowly made his way over to her. Every moment she could feel her lower floodgates of Canterlot loosening up in anticipation of their being stormed by the stupendous red war machine swinging between Mac’s legs. So entranced was she by Big Machintosh finally assuming the position, she barely even noticed the rising sun coming over the horizon.
With a little bit of maneuvering with her magic, Twilight got Not-So-Little Macintosh primed and into position. Like, if that price piece of ladies’ delight was a scientist getting ready to do some sort of seriously important experiment, he'd be in the zone. By that I mean lab coat, goggles, and gloves all on. Maybe some Beats by Dre too, like in that commercial with LeBron where he's getting ready for the NBA finals or whatever. For science!
Twilight shook the thoughts from her head. Now wasn't the time for mental foreplay! Now was the time to realize her dreams and ride the baloney pony!
Suddenly, the door slammed open, and a loud country voice startled the two near-lovers.
“Goooooooood morning Big Ma-” Applejack stopped mid shout, unable to believe what was going on before her. Her dear friend Twilight had seemingly snuck into her house late at night to have an affair with her very much spoken-for brother. “Twilight! You have ten seconds to give me a reason not to knock your horses off!”
Twilight stammered incoherently, unable to form words as she watched Applejack effortlessly toss her brother off of Twilight’s terrified form. Behind her, she could feel the floodgates drying up and the Cave of Harmony™ closing swiftly at this new and very much unwelcome onslaught. Twilight prayed to Celestia, she needed to escape quickly, and for that she would need a distraction!
Thankfully Twilight’s thoughts were answered!
How convenient right?
The sun had risen up and now blasted through the window, temporarily blinding Applejack and giving Twilight a chance to escape! As Twilight turned to the window with glee, throwing it open to leap through, her mentor’s face appeared in the sun.
“Twilight, what the hell, girl?” the Princess of the Sun deadpanned. “Can’t you just masturbate like any other pony? Shit, this is the third time I’ve had to do this since you hit puberty. It wasn’t funny the second time either.” Twilight’s face fell at this. Celestia turned her disappointed gaze away and looked back towards Applejack. “Applejack, just let the poor girl go. It’s not like she’ll learn her lesson now if she couldn’t get it the first two times.”
Applejack tipped her hat to the sun. “Ah reckon your right Princess Celestia.” Applejack managed to use the wrong form of ‘your’ in speech. “Ah might as well let her go, but if she thinks she can come over here and see mah brother again sometime soon then she’s got another thing coming to her.”
Twilight nodded sadly. For the third time in as many years she had been caught trying to sneak into another pony’s house for sex. Still, it was less embarrassing than the time she wound up in Rumble’s bed thinking it belonged to Thunderlane. This was probably part of some sort of condition.
So Twilight left and got back onto her Segway, taking the long way home.
At least it had a pleasing hum.