Original Story
After hours of long work, almost no pay, and little to no appreciation, a vacation is exactly what you need. Life in Equestria was far from easy, but at least along the way you were able to make some friends that make life a little more bearable. Your bros handed off to you this application to a stallion retreat being hosted by Iron Will. To be honest, it sounded pretty awesome. All of them had gone before and told you everything about it. Alcohol, mares, awesome food. A true bachelor's paradise.
Of course, after all of you went once, you were hooked. The stripping mares was a little bit awkward, but the resort was focused on stallions. Plus, it's not like they are going to pull a female human out of thin air. Plus, over time, you've learned to appreciate their... finer tastes. Since then, all of you have made it a point to go three times every year, that is, when you can.
With your bits in hand and bags packed, you double check the application for this season's stay at the resort. After a quick examination, it looks like you forgot to fill in one of the fields.
“What is your fetish?"
Well... This is certainly new. In experiences past, they always had some special nightly entertainment for the stallions, however, this time the resort seems to be going all out. If you put down what you like, maybe it will be a better time when they invite guests for the evening. You never did it before though... What could be different about this time?
Your eyes read over the question as you sit at your kitchen table.
What the heck! Why not? It's not like it's going to hurt the experience. Let's see....
"Surprise me."
Just imagine it. Heading back to the cabin after some great food and a brew. Hop in the shower. Suddenly, a mare enters the shower with you with half lidded eyes and a wide smile.
A smile curls on your lips. Yeah, that would be nice. You stuff the form in your backpack and jog off to your destination. Camp Diamond Pond.
When you get there, all your bros are already waiting outside. Snowflake, Braeburn and Big Macintosh all talk and joke heartily with wide smiles. You wave at the three and call out to them as you approach.
"Braeburn! Good to see you could make it out buddy! It's been a while since I've been to Appleloosa,” you say out to the southerner.
"Well it's been awhile since Ah've been to Ponyville partner. Ah'm happy ya'll came too," Braeburn replies with a friendly air.Big Mac simply nods with a smile.
"Well, what are we doing out here?! Let's get in there and start this shit!" you say to your friends.
"YEAH," exclaims the buff white stallion.
The four of you race inside the camp toward the leader's cabin. Outside, Iron Will waited patiently while reviewing some notes on his clipboard. The four of you line up side by side and at attention. You would almost think this was a bootcamp at first glance.
"Good Morning Stallions," Iron Will addresses the four of you.
"GOOD MORNING, SIR!" the four of you bellow.
"Welcome to the retreat. We have some simple rules for you all to follow for you four to enjoy your stay," the camp counselor states. He begins to pace in front of the four of you. "First of all, nobody gets hurt. There will be no grave injuries on my watch. Second, it is encouraged for all retreat members to utilize the free bar and drink throughout the entire retreat. However! Know your limit!" Iron Will stands in front of Braeburn, who stares into the ground. "We don't a repeat of last year."
"N-No sir," Braeburn chokes out.
"Good. Then, now I am afraid to share that our nightly entertainment is unavailable this evening. As a result, we are trying to arrange a replacement entertainer or create arrangements with the Princess of the Night." Big Mac's eyes go wide for about half-second and then he regains his composure. "With that gentlemen, there is fishing supplies out on the dock, cards in the bar, gym is open and cabins have your names on them. When you get hungry, just head to the bar and tell 'em what you want. Enjoy your stay. Meet up at the bar at sundown for an update of our nightly entertainment. Understood?"
“SIR, YES SIR!” the four of you reply.
“Then get at it!” he bellows.
You trot joyfully down the path to the camp, humming gleefully and reveling in the pride of a plan coming together smoothly. Iron Will called you out after you volunteered to work at a retreat for stallions that Anon was going to. After dealing with Berry Punch, who was ahead of you in line, you were now Anon's nightly entertainment.
Of course you have to deal with his friends as well, but at least you can save the best for last. The idea of finally being able to touch his silky smooth skin and chisled muscles sends shivers all up and down your yellow body.
“Alright, Fluttershy,” you say to yourself. “You can do this. Just stay calm.” You do your best to contain the entirety of your excitement. Today was finally the day that he will be all yours.
Just off in the distance, you can see Anon in a boat out on the lake laughing with his friends. The sun glistening off his delicate skin and showing every inch of his heartwarming smile. Your heart fluttered on the inside and a warmth spread through your chest. Your Anon is so handsome.
As confident as you can be, you stride into Iron Will's office. It wasn't particularly large. Just a small trailer near the entrance of the park where he filed paper work and had a small bed for himself if all the cabins were taken.
"You wanted to see me Mr. Iron Will, sir?” you say to him.
Iron Will looks up from his desk of paperwork and refocused his attention to you. "Oh yes, Fluttershy, thanks for coming. It looks like Berry won't be able to entertain the boys tonight. I was hoping you could fill in for her,” he asked.
"Oh! Why, of course! I would be honored. What do they like? Maybe I can do something special for them,” you ask in fake surprise. Iron Will hands you a small stack of papers.
"This should cover everything they like. Go ahead and use anything in the camp. You can use the fifth empty cabin if you want,” he says.
You smile to him. "Don't you mean 'If I need it?'" You say in a suggestive tone. There's no sense beating around the bush. You know what you are here to do.
“There's that assertive pony I know! Go get 'em tiger. I'll be at the bar at sundown to introduce you. Meet me there?" he asks.
"Sure! Lemme just read these over and get some supplies. Thank you, mister Iron Will, sir. I won't let you down."
"No Fluttershy, Thank you,” he says.
You leave his office and head to the empty cabin with a wide smile. Jackpot. After years of attempting to discover Anon's fetish, working up the courage to win his heart, and taking assertive lessons to attempt to court him, his fetish rests in the paperwork right in front of you.
The anticipation eats at you as you walk to your cabin. It's too much. There's no sense in waiting. Let's see what these boy's fetishes are.
Flipping through the papers, you notice Anon's paper is on the bottom. You've snuck away enough of his grocery lists and handwritten notes to recognize his handwriting from anywhere. Might as well save the best for last.
“Let's see...” you say a loud. “First is, Big Mac. And his fetish is... 'his sister?'” you say in surprise. You stop in your tracks and vomit a little in your mouth. Hopefully he means Applejack and not Applebloom. Maybe you can find a cowmare hat somewhere.
Next... Braeburn? Oh yes! Applejack's cousin from Appleloosa. You remember meeting him once. Let's see what his is.
“Pegging?” you say quietly. You stop in your tracks and look at the stallion sitting in Macintosh's boat. “Apples sure have weird stallions...” you say quietly.
Good thing you were prepared for anything with Anon. Slipping into your cabin, which you decided to begin to fill yesterday, your gaze is cast to several stacked boxes where your vast array of sex objects are hosted. Inside them have every possible object you could need, from gags, whips, and even a restraining suit which was tailored to Anon's exact measurements.
Rarity is such a good friend.
Next is... Snowflake. You think to yourself who that stallion was. Oh. The really strong pegasus with little wings. That poor stallion was picked on all the time in flight school. Maybe you should be nice to him tonight. Reading the paper, your eyes move down to the fetish field. His fetish is... obese ponies?
You stare at the paper blank faced. “Huh.” At this point, you shouldn't even be surprised. Stallions are so weird.
Next is Anon.
You close your eyes to finally relish in figuring out his fetish straight from the source. You lay on the bed and hold the paper close to your chest.
“Anon... After all this time, I finally get to know.” You open your eyes. "He... Likes surprises?"
You stare up at the ceiling and begin to think of how to execute this for your love. It IS almost Nightmare Night. Maybe he means scary surprises. You smile widely at your genius idea. If there is an expert on what is scary, it has to be you. You know what all of the most terrifying things are. Then you simply smile.
Fluttershy had an awful idea. She had a wonderful idea. Fluttershy had a wonderful, awful idea.
The sun was beginning to come down over Camp Diamond Pond when you and the rest of the stallions decided to grab some grub up at the bar.
"I wonder who they managed to get for tonight?" you ask the guys.
“Well we sure know it won't be Rarity again, huh Braeburn?" chuckles out Snowflake.
"Ah told her ah was sorry... She wouldn't look at me fer a month... “Braeburn sighs as everyone laughs. “At least it wasn't like the time it was Applejack. Big Mac looked like he was gonna have a stoke."
Big Mac looks away.
"We don't talk about that Braeburn. It was bad enough the first time,” you reprimand him.
"Eeyup," says the quiet stallion.
As you get to the bar, you grab the door for your buddies.
"Alright, guys time for some poker. I call deale-"
You are cut off when your eyes focus on the room in front of you. In the middle of the bar was Iron Will, bound up and gagged.
“What... the fuck...” you say in shock.
The four of you race over to him and roll him over. He's out cold and lays in a pool of his own semen.
"What happened? Do you think he was attacked?" you ask the guys.
"Oh shit..." gasps Snowflake.
"Nope. Nope. Nope," says Big Mac, who is quickly losing his cool.
Braeburn backs up. "I... guess it is Nightmare Night tomorrow... is this what they do at this time of year?" he asks.
You give Iron Will a few good slaps on the face. He doesn't even react.
“He ain't gettin up anytime soon,” you say in observation. Standing up, you look among the three other stallions. That's when a terrifying thought strikes you. With every passing day, it seemed that Fluttershy was getting more and more persistent with her human fetish. She wouldn't... cross that line, would she?
"You guys don't think that.... he was raped do you?" you ask.
The four of you all look at each other in silence. Tension fills the room and the atmosphere grows cold.
Now wait a minute. This is Fluttershy we are talking about. Shaking your head, you begin to laugh and the rest join you. "That's a good one Anon... Iron Will... getting raped..." chuckles out Braeburn. “There's no way that sort of thing would happen here, this is a reputable establish-”
The lights go out in the bar. A girlish scream rings out in the darkness.
"Everyone shut the fuck up and get down,” you scream, dropping to an army crawl.
All of Fluttershy's crazy ass fetish attempts have honed your survival senses. Light hoofsteps can be heard walking across the room. They stop nearly inches from you. Just stay quiet, Anon. Maybe the attacker doesn't know where you are. A soft feminine whisper fills your ear.
"Such handsome stallions shouldn't be out this late..."
A giggle. The lights turn on. No pony is there.
Big Mac is in Braeburn's arms, shaking like crazy. Quickly, he jumps out and acts like nothing happened.
"Alright. Well, no joke anymore. I think Iron Will was raped,” you announce. They all nod.
"What are we going to do? I mean... I wanted some... but not like this," asks Snowflake.
"Let's stick together and make sure nopony is out of each other's sight. We are gunna be fine." you say.
"Eeyup,” answers Big Macintosh.
The nervous tension fills the air. This ain't good.
"Alright guys, let's just make this simple. How about we get some brews, play some cards and wait for this whole thing to blow over?" you ask. “We can watch Iron Will until he wakes up and he can find us a way to get some help. Sound fair?”
"YEAAAH!" Snowflake answers overenthusiasticly
"Eeyup,” Big Mac nods.
“Sure thing,” Brawburn agrees.
"Two pair!" Braeburn calls out confidently. “Beat that , Anon.”
With a smile, you lean back in your chair and smile."Flush,” you say proudly, tossing out your hand.
Braeburn sits back in his chair and counts his left over chips.
"OH YEAH! SUCK MY COCK!” you exclaim loudly, pumping your fist. “Throw out your trash, Big Mac. I got a pile of chips to take.”
Macintosh looks at you over his cards. He drops them calmly on the table revealing a full house.
"GOD DAMN IT!" you exclaim. Macintosh chuckles and takes the pot.
"Well, I'm out. How about I get us some more brews from the kitchen,” Braeburn calls to the guys.
"Sure Brae. I need one. God damn it, Mac. You gotta teach me that poker face,” you answer.
“Ee-nope,” he answers proudly.
“Alright. I'm dealer. Let's DO THIS!" Snowflake borderline screams, although you are two feet in front of him.
The door to the kitchen closes behind the Appleusian as you look at your hand. Ace, ten off suit. Good hand. You dig your eyes directly into Big Mac. He doesn't even know what's coming.
You dig your eyes directly into Braeburn. He doesn't even know what's coming. Your strap-on is primed and ready. Lubed of course. You aren't a monster.
That is... unless Anon would want you to be.
You just hope this is whole act is surprising enough for them. They all came out for this... right? Does that count as consent?
Quietly, you flutter behind him with a gag in hoof. Slowly... Carefully. He stops and opens the cooler. NOW!
You tackle him and gag him as quickly as you can. The gag is a perfect fit and silences him completely.
"Ssshhhh....." you whisper to him as he turns and looks up to you in terror. You prod his rear entrance with your new phallus. "Just enjoy this."
His eyes go wide in terror and then shuts them tight. You push yourself hard inside him. It slips in with nearly no resistance. That's weird.
That isn't what the 'Big Book of Putting Things in the Butt' described. Normally people just bought the book to... well. That's another time.
Right now, you needed to pleasure Braeburn. You didn't want to... but it was all for Anon. Sliding the massive member in and out of him sends waves of pleasure though his masculine form. Trying to speed up the process as fast as possible, you begin to stroke him off.
He begins to moan into the gag, and drool begins to pour out of his mouth. It must be more enjoyable than you would imagine. Maybe when Anon is your husband, you will have to suggest this.
Braeburn's body tenses up, and he shoots a massive load all over himself. Eww. Some got on your hoof. You wipe it off on his face. Now, for the finishing touch. A little chloroform to knock him out for the night...
He looks up into your eyes with the feintest hint of a smile.
“Was that good for you?” you whisper to him. He nods quickly. Perfect. “Good, then it's time for you to take a little nap...”
"GOD DAMN IT MAC! EVERY TIME!" you scream.
Snowflake and Big Mac laugh heartily as you now are only wearing boxers. At this rate, you would have to start doing humiliating things to get more chips.
"I need a brew. Braeburn! You alright in there?" you call to him.
“You didn't find a stallion you fancied in there did ya?" teases Snowflake.
"How long has he been in there?" questions the Apple brother.
"Dunno... lets check on em," you ask.
They at least give you the clothes back and you can throw them on before you check the kitchen for Braeburn. As you enter the door,
"SHIT!" you yell.
His body is laid out in the floor... covered in semen and gagged. Oh fuck. The rapist got to him. He wasn't even that far away from you guys. This is bad. Really bad.
"Alright... alright. Let's not panic... The bar isn't safe... let's just try to get to a cabin or something," you tell the guys.
The other two nod and you leave your friend to rest. As you exit the bar, you notice that most of the camp's outside lights are burnt out or flickering in the pitch black night.
"Stay together everyone. The cabins aren't that far,” you tell the boys.
Even though you are the biggest stallion in town, this was absolutely terrifying. Nope. You need to be confident. For AJ.
It was your duty as a big brother. Keeping to close to Anon, you scan around for any sign of the rapist. A swift movement in the darkness catches your attention. The outline was faint... but... you would swear you saw...
There it was again. It was. Your father's hat. Stopping, you scan the darkness. Anon and Snowflake stop and turn to you.
"Big Mac, you have to hurry up. We can't stay here," Anon says to you.
If Applejack were here, you couldn't risk her getting hurt. The idea of someone using your pure, innocent, honest sister boiled your blood.
"Nope,” you said.
"Come on man," whispers Snowflake. "We are at risk in the open."
You have to tell them. Explain to them what you would do to that pony if they ever touch your little AJ. The feelings you cherished as you helped her grow up into the beautiful young mare she was today. Until that one night last year, when everything changed... How much you loved her... Not just as a brother...
"Nope,” you said.
Nailed it.
"Fuck it. Let's get to the cabin dude. He's fucked,” Snowflake said.
"Alright..." mutters Anon.
Snowflake gallops off and Anon follows, looking back at you with worry. Looking through the darkness, you see the familiar stetson slowly move towards you slowly. The footsteps are seductive, and the way her strong haunches move towards you. She wouldn't do this if she knew it was you.
Who would have known that Iron Will would actually do this for you. You owe him one hell of a tip. Opening your mouth, you prepare to tell your long practiced proclamation of love, but her hoof simply places itself on your lips. It makes you stiff in seconds.
Her face is shrouded in darkness as her lips move to your neck. Her tongue slowly traces it's way down your body and you feel your legs weakening. Suddenly a strong push forces you down, and you feel her on top of you. She is pushing you deep inside of her.
Must. Not. Cum. Inside. Little sister.
She begins to ride you exactly as you would have dreamed. Cowmare style.
You place your hooves on her haunches and slam yourself deep inside her. The heat begins to spread throughout your body as you feel your muscles tighten. She's so wet and tight.
Her soft moans and giggles fill your ears and you close your eyes to relish the moment. You are close. She pushes herself down on you harder and harder. Shit.
At this rate, you can't control yourself. You try to push her off, but she casts your hooves aside and holds them down as she pushes down harder. Every muscle in your body tightens up. You let out all of your pent up breath as your release your seed deep inside your little sister. What kind of big brother are you?
"Mmmmmm~" she says aloud.
Oh god, you could have came a second time from that. Tiredness begins to wash over you. Applejack places some sort of cloth over your muzzle and you breathe deeply. You hear one last thing before you lose consciousness.
“Good Night, Big Mac.”
The voice was familiar, but didn't belong to your sister. Your stomach drops. That wasn't Applejack.
Snowflake rips open the door to his cabin and you jump inside. The two of you push a bed in front of the cabin door and sit to catch your breath.
"What are we going to do Anon? We are the only two left," he says aloud. You look at him... then back at the floor.
"I... I don't know,” you say aloud.
You look throughout the room for an exit plan. Chimney? No. The front? Not an option. The window.
It's your best shot if the rapist gets in here. Snowflake wouldn't be as lucky though. It's too small for his massive muscles. A massive pound on the door makes the two of you panic. The two of you push on the bed to reinforce the door. Another booming hit on the door. Then another. And another.
The door sounds like it's beginning to split. Snowflake breathes fast and hard, trying to keep his composure. Suddenly, the rhythmic attack stops.
Snowflake looks to the door, and then to you, and then the door.
"YEEEEAAAAHHH!" he exclaims.
"Snowflake, shut up," you whisper to him.
"THAT'S RIGHT! YOU AIN'T GETTIN TO US! JUST TRY!" he shouts at your attacker.
"You really don't want to challenge them..." you say to him.
An eerie silence fills your ears. Then, it all clicks. The pieces all add up. You sprint to the window just in time to dodge Fluttershy zooming down the chimney.
Ripping open the window, you see Fluttershy gag and blindfold Snowflake.
"I will never forget your sacrifice friend..." you say to him.
You jump out the window and begin to sprint towards the dock. Fuck. You never expected her to have the balls to get violent. Maybe you could lose her in the woods.
No way, she probably knows them thanks to her animal friends. Which means swimming is probably also out. Just gotta hide somewhere... and fast.
The empty cabin! That's it! Iron Will it was used for storage or something earlier. She wouldn't expect to you hide there. Quickly, you sprint towards the fifth cabin, trying to dodge any light that could highlight your position.
Kicking open the door, you jump inside and slam the door shut. You reach for the lock on the door, but find it snapped off and lying on the ground.
The room is filled with various boxes. Quickly, you rearrange the boxes to hide you in a corner of the room. There. The perfect hiding spot. You are completely out of sight. All you can do is hold your breath and wait.
Soft hoofsteps can be heard walking along the cabins. "Oh Aaaannooonn..."
You take a hard gulp. Keep it together man.
"I finally knoooww itt..."
Fuck. She must have found the paper. Jokes on her. You weren't surprised.
You were terrified.
So this is a win for you... Right?
Right?
Her hoofsteps slowly approach the cabin as the door slowly creaks open.
"Just let me show you my love..."
You hold your breath. This bitch is crazy. She pushes aside a few boxes and then looks directly at you. No way! She can't possibly see you. Slowly and diligently she makes her way towards your box fort.
Your heart races and you close your eyes.
"Hmmm...." she whispers. You begin to shake.
"Are you... here!"
A stack of boxes a few feet to your left fall over.
You about shit yourself.
"Hmm... not here,” she says aloud.
The door creaks shut again and silence fills your ears once more. You let out a deep breath. The boxes are ripped away and she looms over you.
"GOTCHA!"
She's too fast and pulls you over to the bed. She braces you down and straps your arms into handcuffs. She smiles as she sits on top of your stomach triumphantly.
“I finally have you all to myself, Anon,” she whispers. Your eyes are wide eyed in terror and you try to fight your restraints. Her smile widens and her eyes become half lidded as she bites her lip.