Princess Pleasures and Pains

by CosmicWrinkles

First published

Celestia and Luna deal with a human about his sexual escapades in PonyVille each in their own way

When the local human realizes he'd been tricked and basically Pimped Out by Twilight Sparkle through his job at the local Spa he goes to confront her, only to discover Celestia and Luna beat him to it. It seems the sister's aren't there for the same reason though, and while one uses him to indulge her kinks for pleasure, the other uses her fetishes to punish him.

Chapter 1

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Bursting through the front door of Twilight's place Anon is ready to unleash verbal hell on the purple pimping pony inside. As he enters though three sets of eyes turned to greet him, and he is surprised to see just who is there.

“Princess Celestia? Princess Luna? What are you doing here?”

“Hello Anon.” Celestia smiled warmly and turned to face him.

“Greetings Anonymous.” Luna chimed in right after.

The third pony was Twilight herself, and as much as he wanted to start yelling at her for what she had done, you don’t just chew out the favorite pony of the resident god ruler in front of them. Not without losing a limb or possibly having one randomly attached magically to you somewhere. He needed to wait till she was alone to make her answer for what she’d done. Turns out though Celestia was here for the same reason as he was.

“It’s good you’re here Anon. It seems my student has been up to a great deal of mischief lately.” Celestia glanced over at Twilight who promptly looked down in shame. Celestia then floated a small flyer toward him.

‘What’s this?” He took the pamphlet and read.

“Best Wing Jobs in all of Equestria.

A Horn strokers Paradise.

Come get your rump rubbed and

Feel the Magic of Fingers.

Now at the one and only Ponyville Spa.”
Included was a picture of Anon on the flyer and a list of price quotes from Twilight.

“Son of a Bi…”

“Yes Anon I know.” Celestia cut him off before he could finish. “These flyers have been passing around all of Canterlot.”

“I swear Celestia, I didn’t know what I was really doing.”

“I am also aware of your ignorance in this matter. Rest easy Anon. I was In the middle of discussing the issue with Twilight when you arrived. If you would please give us some privacy for the moment so I might finish my dealings with her.” Celestia turned toward her sister. “Luna, please escort Anon into the other room while I finish here.”

“As you wish sister. Come Anonymous.”

As angry as he was at Twilight, and humiliated at finding out about the flyers that had been going around behind his back he still felt a twinge of sympathy for the purple pony. She was now facing the same mare after all who sent her own sister to the moon for a thousand years. He silently followed Luna till they were out of ear shot at the back of Twilights house.

Once alone Luna turned to face Anon. “This matter is most troubling Anonymous.”

“Yeah, tell me about it.”

“We did not think our sister would find out about the flyers so quickly. We are most disappointed”

“Well what can you do? After all we’re all just.., wait what?”

Luna kicked the door to the room they were in shut with a hind hoof and moved in close. “We had hoped to get in one or two sessions with thee before our sister had become aware of what was going on. Still, tis a small matter I guess as we now have this time to act.”

“This is a joke right? You’re joking? Please tell me you’re joking.”

“Tis no joke. Indeed tales of your talents at pleasuring a mare have spread quickly among the nobles. I had planned to sample those pleasures at great length myself but a quick rendezvous shall have to suffice for now.” Luna turned to point her blue duel moon butt directly in Anon’s face. “Come now Subject. Pleasure thine Princess.”

“Are you out of your tiny pony mind? Your sister is in the next fucking room!”

“Yes,” Luna gave her ass a wiggle. “Tis a naughty thrill is it not. Quickly now, pleasure us. We are tired of waiting!”

This was unbelievable. All the confusion and mixed feelings at finding out he was being treated pretty much like some kind of fingered bimbo by the pony inhabitants just exploded in him.

(SLAP!) The sound echoed out in the small room like a gun shot.

A completely stunned and shocked Luna ever so slowly turned her head to gaze back at Anon. Her eyes were as big as saucers and her mouth gaped open in disbelief. She just stared at him for what seemed like forever without uttering a sound.

For his part Anon quickly began to panic. “Oh my God! I’m so sorry Luna! I, I don’t know what came over me. It was just.., I mean with everything that’s happened and now you. I.. I… I just reacted. I didn’t mean to..”

Anon looked down at the giant red hand print now showing up right across the left white crescent of her moon cutie mark.

After what felt like forever Luna finally spoke, “Do it again!”

“What?”

Luna pushed her flank back at Anon and demanded, “Do it again!”

“Wait, are you serious?”

“Yes! YES! We are a naughty Princess of the Night and must be punished. DO IT AGAIN!” Luna kept shoving her plot back toward him till she had back him up against the wall.

“Tis been many many years since a stallion has been so bold as to take charge of us in such a manner.” She began rubbing herself up and down against the trapped human. Grinding herself back against his crotch and legs.

“Hey knock it off!” He started pushing against her flank trying to shove her away, but it didn’t do any good. If anything all the grabbing and rough handling only spurred her on. She was basically using his body to rub herself off with. He couldn’t get out from behind her the way she had him pinned either. Finally he just snapped. “Fine! You want to be spanked? I’ll give you a spanking you’ll never forget!”

(Slap, slap slap)

“Yes! OH YES! More MORE! She was looking back at him with dreamy eyes and basically twerking her butt up and down his entire lower half franticly.

(slap slap slap slap)

“oh OH YES! I am close Sir Anonymous. Thine princess is close!”

“Come on you crazy blue bitch get off me!” He’d thought after the first few dozen or so smacks she’d move, but no. “GET OFF ME I SAID!” He brought both hands down to smack each of her cutie marks simultaneously, and with enough force to cause ripples in the smooth now totally hand print marked expanse of her ass.

(SLAP!)

Luna threw back her head and shuddered in delight as she jammed her plot hard up against Anon’s crotch and rode out the waves of her orgasm. Her mouth was open in a silent scream of pleasure and tears of joy filled her eyes. She held him there for a good minute just trembling. Then without a word she just collapse face first with her ass still in the air.

With her weight off him he was able to shift to the side and get out from behind her. The princess had her eyes closed and had a pleased sleepy look now plastered to her face. He looked down to see the entire front of his pants from his knees to the waist were drenched in Luna’s juices.

“Oh man that’s just so wrong on so many levels.” He wasn’t sure if he was bothered more by being covered in the Princess’s secretions, or that he was sporting a semi hard on from the whole experience. He glared over at Luna only to discover she had indeed just fallen asleep. “That’s just great. Going to gets your jollies and leave me a sticky mess then doze off hu?” Suddenly he knew how a lot of his ex-girlfriends must have felt over the years. He sighed and shifted uncomfortably in his wet pants. Maybe if it hadn’t soaked all the way through to his underwear yet he might be able to strip off the pants and just wear those. Popping the button open and pulling down his zipper he just started to pull them off when the door opened.

Standing there was Princess Celestia. She looked at him with his pants half way down to his knees, then over to the unconscious form of her little sister with her visibly abused ass sticking high in the air. She didn’t look pleased.

“Wait wait! It’s not what it looks like, I swear!” Anon stood there in a panic.

Celestia stomped into the room. She was easily the tallest pony Anon had ever encountered since coming to Equestria. At her full height her eye level was just above his own. Add in a very long, and very pointy horn spiraling upwards at least a foot and she made an imposing figure indeed. She walked up to him, then glanced down at his still semi-erect cock tenting out his underwear. She raised and eye brow at him.

“Ok, well yes there is that, so maybe it might be a little of what it looks like, but I can explain.”

“I think,” She said slowly with a cluck of her tongue. “I may have been hasty in blaming Twilight entirely for the events here in Ponyville. Perhaps you were not as unaware of what you were doing as I had thought.”

“No no! You have it wrong. I’m the victim here!”

She glanced back at her sister and one of the many large and plainly visible red hand prints adorning Luna’s ass. Then back at Anon who was hastily pulling his pants back up. Then at the large wet stain covering most of those pants. “You know, there is a special punishment for ponies who commit crimes such as this?” Her tone was low and rather unsettling. “A punishment that fits such crimes very well.”

Anon was pretty much frozen in terror at this point. He was fucked and he knew it. It wasn’t as if there was anyone else in the room when she got here, and no one in all of Equestria that could leave a hand prints like the ones now adorning Luna’s ass. He closed his eyes as she got so close, he could feel her breath on his face. The heavy sent of vanilla and light cedar seemed to fill the air. He peeked open an eye and saw that she was now towering above him. Her horn glowing brightly and Anon feared the worst. Then something completely unexpected happened. Something even worse than his worst fears. Looking down he saw one of Celestia’s hoofs rubbing up and down his crotch.

‘What.., what are you going to do?”

She lowered her head and in a matter of fact voice said,” I’m going to punish you of course. If you are lucky you very well may survive. Though none have so far.”

A bright golden flash and the sudden uneasy feeling of falling, then darkness. Slowly lights began to appear as one by one candles began to flicker and shine revealing a large room. As more and more of them lit up on Anon realized he was in a very large bedroom. The Royal bedchambers to be exact. Princess Celestia stood in front of him, her horn glowed a golden hue as she continued to add candles till all corners of the room were visible. The place was large. Easily twice the size of Twilights entire library, and very lush. Rich wall tapestries and extremely comfortable looking throw pillows adorned the room. Several large wardrobes and dressers were against various walls along with a massive canopy top bed.

This couldn’t be good. If being teleported straight into her bedroom wasn’t clue enough the hungry stare she was giving him told him all he needed to know about what she wanted, or so he’d thought. Once all the candles had been lit she trotted up close to him. He stood his ground, determine not to let another pony take advantage of him. She brought her face a mere inch from his and the same sweet scent filled his nose as her hot breath blew across his lips. Her large purple eyes stared deeply into his, and in a breathy eager voice said something he never thought he’d hear from her.

“Put the costume on.”

“Huh?”

Celestia motioned towards the bed with a toss of her head and repeated her order. There was no mistake from the tone of her voice, that it wasn’t a request. “Put it on, now.”

Anon looked over toward the bed noticing some kind of outfit laid out on it. He slowly walked over to the foot of the bed while keeping a watchful eye on the princess. She didn’t move, just stood there grinning like a cat who’d cornered itself a mouse. Once over at the bed he shifted his gaze quickly down and glanced at what she was talking about. He didn’t want to take his eyes off her for too long. It took a moment for his brain to fully process what it had just seen, but once it had it demanded he take a second look to verify what it thought it saw. “No. No it can’t be. There’s no way it could be.” He looked back down and his eyes grew wide as he realized exactly what she wanted him to put on.

“Oh screw that lady. There is no way in hell I’m putting that thing….”

His words were cut short as Celestia levitated one of the large seven foot candle stands over next to him, then effortlessly twisted the long metal length of it into a neat little bow with her magic. She let it drop to the floor with a loud metal clang. Still not moving, still not saying a word, but her grin had grown into a very wicked looking smile.

Message received loud and clear. He began scrambling out of his still Luna soaked pants and pulled his shirt off. As he struggled to get the costume on Celestia had moved over to one of the large cushions and sat down giggling like a schoolgirl and clapping her front hooves together in excitement. He grabbed the last piece and with a sigh of resignation pulled it down over his head, then adjusted it so the horn on top stuck out at the proper angle. The purple outfit was snug and the two small wings attached at the back bobbed awkwardly as he moved. The large star shaped pattern sewn into the seat of the pants lined up perfectly with where a cutie mark should be. Yup, you guessed it. It was a Twilight costume.

Celestia gave a sqwee of pleasure at seeing how well it looked on him then stood up and cleared her throat. “Why Twilight, what a pleasant surprise.”

Anon sighed and braced himself for what he was about to do. A quick glance at the metal pretzel of a candle stand pushed any further reservations from his mind as he bid his dignity a fond farewell. “Princess Celestia!” He squealed in his best attempt at a high pitched Twilight impersonation. “I’ve come to deliver my report on Friendship.”

Celestia sashayed up to him slowly. Her wide white flank swinging back and forth behind her as she approached. “Oh Twilight my faithful, and oh so slutty student. You don’t have to play coy with me.” She brought a hoof up to his chin and raised his head so they were once again looking eye to eye. “I know what you’re really here for. It’s what you always come here hoping for.” She moved her hoof from his chin down to start tracing little circle patterns over his chest. “Isn’t that right my little purple pony slut?” She leaned in and began placing hot wet kisses around his lips before finally landing one dead center and going in for a deep tongue laden mouth-fuck of a soul kiss.

Anon gulped nervously as he was French kissed by the large white horse. Dam, this was just so wrong. So nasty. So degrading. SO… wait was he getting hard? What the fuck dick?! What the FUCK! She pulled away with a wet slurp leaving him panting and opened mouthed. She giggled slightly.

“Do you want what you came her for Twilight? Do you want me to give you what we both know you’ve always wanted?” Celestia took a few steps back and eyed the purple costumed human with an intense lust.

For his part Anon nodded numbly. His dick had taken over master control from his brain during the kiss. Still some very small part was trying to scream to him “She’s a fucking horse man!” To which his dick promptly replied “what’s your point?”

Celestia turned around and raised her tail high into the air. “Time for your Oral Exam Twilight.” She waved her large white plot back and forth in front of him. Remember ‘Twilight’ your being graded on this, so be sure and do your best to earn an A and make your teacher proud!”

A golden aura surrounded Anon and he was magically pulled closer and closer to the waiting winking nethers of the princess’s juice dripping sex.

Countless hours later the doors to Celestia’s private chambers burst open and a radiant, smiling Celestia pranced forth. Her white coat gleamed with a shine it hadn’t had in years and she felt as young as a filly. Seeing her long time personal attendant slightly down the hallway arranging some flowers she walked over with a hop in her step and a tune on her lips. “Ah good morning Mint Lilly.” She chimed out in a happy voice.

The whitish green unicorn turned and curtsied to the princess. “Good afternoon your Highness.”

“Afternoon?” Celestia glanced out a nearby window and noticed it was still pitch dark.

“Yes your Highness. Late afternoon in fact.”

“Oopsie.” Celestia blushed and giggled a bit. “I guess I should go raise the sun before it’s time for sunset then.”

Mint Lilly smiled. “That would probably be best your highness.” She hadn’t seen the Princess in such a good mood in years. She certainly didn’t remember her ever missing to raise the sun on time. Not once in the twelve years she’d served as Celestia’s personal maid had she even been a few minutes off. To distract her enough to actually forgo raising the sun on time, whoever she had spent the night with must have been something truly amazing. A fact made doubly strong by the Princesses very loud screams of

“Oh ME, OH ME OH ME YES! For the love of ME don’t STOP!”

Those bellowing cries echoed throughout all the halls all night. The castle actually shook several times, and a few of the engineer ponies were worried about the castles foundation. She watched as Celestia began skipping down the hallways, off to go complete her Royal task, only to pause then come skipping back.

“Lilly?”

“Yes your Highness?”

A slight blush crossed Celestia’s cheeks. “If you would be so kind as to change my bed sheets.”

“Yes your highness.”

“Oh and tidy up a bit in there for me as well.”

“Yes your Highness, of course.”

“And Lilly…?”

“Yes Your Highness?”

Celestia leaned in closer to her and in a hushed voice added, “Fetch the Luna Costume from the “special” wardrobe and see that it’s laid out on my bed for this evening.”

Mint Lilly smiled and nodded. “Of course you’re Highness.” She watched the ruler of all Equestria go prancing off with a double step in her gate and humming once again.

Peeking into the darkened bedchambers Mint Lilly’s senses were overcome by the powerful smell. The room reeked of sex and sweat. She called out a tentative “Hello?” and got a week groan as a response. Well whoever he was at least he was still conscious. Which is a lot better than the very very other few who had had the honor of spending a night with the princess. Rest their poor pony souls.

She walked in trying to ignore the wet sticky spots she trotted over on the way to the windows. Flinging the curtains back and opening the windows to air out the room she noticed the sun now rising off in the distance. As the light from the late afternoon sunrise filled the room Mint Lilly’s eyes grew wide. Large wet sticky splotches dotted the room, and the walls, wardrobes, dressers, cushions. She looked up in wonder. “The ceiling? How did she get it up on the ceiling?” The bed had a small puddle in the center of it she’d swear at least an inch deep. Laying sprawled out nearly comatose and severely dehydrated was the instrument of Celestia’s pleasure.

To Mint’s surprise it wasn’t a stallion. She’d seen the Anon male a few times accompanied by Celestia’s student Twilight occasionally around the castle, so recognized the creature but never really met him before. He was a mess. Covered from head to toe in sweat and Celestia’s love. The tattered remains of some kind of purple clothing barely hanging off one leg and an arm. He groaned again weekly. His cheeks looked hollow and dark circles were under his eyes. He reached up a shaky hand toward her. Gasping and coughing. Clutching at the front of her maid’s uniform he managed to pull himself slightly up out of the sticky mess he was laying in. He seemed to want to say something.
She leaned down and listened and in a raspy voice he said,

“I had snu snu..”

Then passed out cold. She smiled down at him and wiped his sweaty brow. “Of course you did dear.” She should get him cleaned up she thought. She should get him to a Hospital she thought. She should… not miss this opportunity to experience something that was capable of making the ruling goddess giddy with afterglow she thought. Glancing around she began to strip off her maid’s outfit…
*****************************************

If you have enjoyed this mindless tale of debauchery and trickery, here are some books you may be interested in:
Twilight Sparkle’s five volume work on “Zen and the Art of Stallion Seduction.”
Applejack’s “Cooking your way into the Heart of a Special SomePony.”
And Fluttershy’s vastly popular “Does this Smell like Chloroform to You?”

Good Night, and have a pleasant tomorrow.