LINK TO MASTER TIMELINE
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DAY 2
 
>You outwardly groan as you come in from you patrolling the city. Last night's... sleeping arrangement left you severely under rested for the work being asked of you.
>But now you're off work and ready for some fun.
>Two out of six ponies broken, but you still haven't figured out which one should be next.
>No matter, you'll think of something.
>As you reach the door, you hear quiet, hurried voices coming from the other side.
"Please, please hurry."
>Upon entering, you see Applejack and Rainbow Dash free from their collars and chains and trying to get the others loose.
>Without even hesitating they both make a beeline for you. Your brain goes dumb for a moment as you take the full force of both of them smashing into you, Rainbow from above and Applejack from below.
>If you hadn't been wearing your new guard armor, you would be seriously injured right now.
>You recollect your thoughts and try to asses the situation.
>Twilight and Pinkie Pie are still tied up. The chains are worn a little, but they don't look like they can break free.
>You are standing directly between Applejack and the door and Rainbow Dash is floating overhead.
>Rainbow can easily escape if you don't do something. Armor and magic immunity be damned if you can't fly to catch her.
>Nightmare Moon's voice echoes in your head
"Their troubles are your troubles."
>With the courage only a cornered animal could muster, you tackle AppleJack to the ground.
>You rise and pull your sword from your side and aim it at her neck. If she moves, she's dead.
"Go without me Rainbow Dash," she says defeatedly.
"Come done here now or I will kill her. And then the other two. And finally the two I've already taken."
"Augh!" Rainbow screams in defeat.
>She may be fast. She may be nubile. But her friends aren't. And she wouldn't dare leave without them.
>You nod your head to the far wall.
"Go there."
>She obeys. Thank... (Is Nightmare Moon your God now?) whomever, she obeys.
>You are not quick witted. The other two still have their collars on. If you had activated them, you wouldn't have even needed to engage Applejack
>Still the thought that you can take the Earth Pony does sit happily in your gut.
>You sheathe your sword and step back causing Applejack to eye you suspiciously.
"You two seem to forget yourselves. I have the power here. You do not. Let me demonstrate"
>You speak your word and the collars constrict on the young mares.
>Applejack and Rainbow Dash exchange horrified looks, but the looks quickly turn to anger as they look like they are about to charge.
"Don't even think about it. Besides if you kill me before I reverse it. It will never end and they will most likely die before you can save them
>Moments pass, but you leave the threat hanging in the air.
>You've never left the collars active this long. The two mares are shaking on the floor not even registering the world any more.
>Shit, you might actually, truly kill them if these two don't break fast.
>You really do not want to do that. If worse comes to worse, you'll call your bluff off. But just a little bit longer...
"Alright! Stop. You're in charge here. Right Applejack?"
"R...Right Please, wontcha just stop? We'll do whatever you want."
>You stop the collars and allow yourself a moment of relief. You've won.
>The two mares wearing collars burst into a fit of retching and frenzied breathing. It doesn't sound pleasant.
"Good girls. Because I've had a rough day and you just made it a whole lot rougher. I'm not even going to put new collars on you right now."
"If you try to attack me or if you disobey the smallest order I will reactivate the collars and leave the room. You will be locked in here with your dying friends and there will be nothing you can do to help them."
>Fuck, you've gotten dark. But you tell yourself it's only a bluff. A dead pone is good to nobody.
>Applejack and Rainbow Dash nod in unison.
"Alright then, Applejack, join Rainbow Dash."
>Applejack hesitates only the barest second before complying.
>You are skating on really thin ice. You've made a threat and if they force you into a situation where you'll have to make good, you'll either lose credibility or actually end up killing somepony.
>You shake the thought from your mind. These two are too loyal for that. They'll follow you. They have too.
>Right now though... Right now it's your time.
>You grin. Fluttershy was alright, but she was inexperienced. That will change over time. But you want something right now.
"Tell me you two, are you a virgins?"
>The shocked look was answer enough.
"I... I... I... am.
"Same..."
>Their eyes are dilating. You're scaring them.
"Good. Good."
>You reach down and scratch behind their ears.
>They don't flinch away, standing strong in the face of... well they have to know what's about come.
>But they really have no idea.
"Put your front hooves down, hindquarters up Applejack."
>She obeys instantly, her shaky legs betraying her earlier resolve.
"Move your tail."
>She flicks it out of the way.
"Rainbow dash. Be a good girl and lick your friend."
>Rainbow's head whips back and forth between you and her friend's winking hole.
"On... on her face?"
>You narrow your eyes and stare at her.
"No... of course not. You mean her... her..."
"Cunt."
>She hesitant but with a quick look to her recovering friends, she steels her resolve and plunges herself down."
>She's slow at first, but quickly picks up speed. She's definitely never done this before, but Applejack doesn't seem to mind.
>To your delight, Applejack lets out a mew of pleasure
>You position yourself behind Rainbow Dash and while the pone knows you're doing something her mind doesn't register exactly what until you plunge yourself inside her.
"AUGH!"
"Did I say you could stop Rainbow," you growl.
>She shakes her head back and forth wildly and continues with her work.
>Your cock is lightly smeared with blood but none leaks out as you thrust yourself back and forth.
>Rainbow Dash passionately throws herself into your earlier command trying to block out the thought of you behind her.
>The more she tries to forget you, the more she pleasures her friend. She's actively working in your interests.
>But you are not a person to be forgotten so easily as you push yourself to the hilt.
>Rainbow gasps and whimpers.
"Does it hurt?"
"N... No. Yes. I... I Don't know."
>She's babbling. There's a cure for that.
>You pull out to the tip and thrust back in. Again. Again. Again.
>She's lets out a mix between a groan and a moan. She's certainly not turned on quite yet, but she very well could be in the near future.
>You go back to a steady pace and remind her of original job.
>With a meep, she returns to her work.
>You peer over her plump ass to see how she's doing and to your surprise, Applejack is literally dripping with juices.
>The sight turns you on further and you increase your rhythm.
"Ah. Hah. Ah. Rain... Rainbow. I feel very hot. It's... It's too much. Something. I... I don't know..."
>Surely she isn't about too...
"AAAAAAAH!"
>She did. Rainbow just made her friend cum. The very thought drives you to the edge.
>You push yourself all the way back in and unleash your seed inside in sync with Applejack's scream.
>You pull out and a minute amount of cum drips out.
>Rainbow lets out a small sob and looks at you with a dripping face.
"Are you satisfied"
>Your member is soft, but messy. Small amounts of blood has made it's way onto various parts of you and you were still dripping semen.
"Clean it," you command.
>She sniffs and begins licking your nether regions, cleaning off the remains of her virginity.
>When you're clean, she blinks and stares intently at the ground.
>Your gaze shifts to Applejack.
>Her face is red with embarrassment and she's panting slightly.
>Dear... whomever, you think you might be getting hard again.
>Rainbow Dash is quiet now. It seems like she suddenly finds the floor very interesting.
>In reality it's just more preferable than meeting your gaze or watching her helpless friends, knowing that she failed to rescue them and that this too will be their fate someday.
>Her hair isn't quite long enough to obscure her face, but she's trying to hide behind it nonetheless.
>It doesn't matter, you see what she's trying to conceal.
>She contorts and scrunches her face, using all of her concentration to control her tears.
>For a moment, it seems like she might win.
>You definitely can not let her win.
>You bend down and whisper in her ear.
"Such pretty wings you have Rainbow. You should beg me to let you keep them."
>Her eyes snap open and with the tension gone, her tears start leaking openly.
"Please. Don't. They're all I have. Take everything else. Take me. But please leave my wings alone. Please. Please. Please."
>Her voice is small and frightened.
>You touch her neck gently, slowly stoking downward to her wings.
"Please. Please. Please."
>She's shaking so much. You can't resist.
>You pluck a feather from the tip. It isn't much. Surely she's lost more while just being reckless.
>It's enough to send her over the edge though.
"All I have. Please. Anything. Please."
>She's openly sobbing, openly begging.
>You're cruel, but you aren't completely callous. If she's willing to accept you, you see no reason to further break her body.
>But it's better to err on the safe side.
"I won't even ask you to choose between your friends and your wings Rainbow. You can have both. But your wings will stay bound at all times unless you are with me. And you are not to fly without my expressed consent. Do you understand?
>She nods dumbly.
"I can be benevolent Rainbow. All I really require is that you know your place. And where is that place for you Rainbow?"
"As your... slave. Master."
>In your elation of breaking another pone, you seem to have forgotten about the strong and still partially defiant Earth Pone.
>But she hasn't forgotten you. You meet her gaze as she watches Rainbow Dash bow down to you.
>The earlier euphoria gone, her eyes are narrow and cold.
"Do you disapprove?"
"You're disgusting."
>You disagree. Disgusting doesn't begin to describe this moment. But... If she wants disgusting. You can certainly oblige.
"What an interesting choice of words."
>The thought can wait though as you feel Rainbow's loyalty begin to waiver.
>Rainbow Dash looks uncertainly between Applejack and you. She feels she has to choose a side. Shit. Testing her this early is not a good idea.
>You stare hard at Rainbow and to your delight she breaks.
"Please. Applejack. Just... It's not so bad really."
>Oh, good choice Rainbow! Pride shows on your face as you gently stroke the mare's wings.
"I just don't want to hurt. And I don't want you to hurt Applejack."
>Simply fantastic. Applejack's face softens and she looks as if she isn't sure anymore.
"Rainbow. I've think you have enough for today. Your friend is fine in my hands. I have a room prepared for you to sleep in."
>She nods and follows you as you lead her to her new quarters.
>You call for guards to move Applejack to your room, where your toys are and you can easily take control of the situation should it spiral.
>She called you disgusting.
>You'll show her just how disgusting you can be.
>You wrack your mind with ideas as you fit Rainbow Dash with her new wing harness.
>You honestly expected Rainbow Dash to be the hardest one to break. But as you finish locking her wings in place, you realize just how much control she has relinquished over to you.
>You do a twirl with your hands and she trots around for you, showing off her new attire before coming back and nuzzling your feet.
>You smile. She definitely deserves a reward later. But right now you have a new plaything waiting for you.
>You make to leave and Rainbow's ears fold flat against her head
"I said I'd take care of her, remember? You're doing good, so nobody has to get hurt. I promise"
>She perks up a bit and nods.
>Nobody has to get hurt, but that doesn't mean nobody will avoid being hurt. She has to make amends for what she said after all.
>Upon entering your room, you see the guards got creative when tying down Applejack. They actually brought in a stockade and immobilized her head and front hooves.
>Her two back hooves have a spreader bar and her tail has been tied up in her hair.
>Although to your annoyance, they seem to have bolted that damn thing to the floor right smack in the center of your room.
>This place is getting cozier all the time.
>You had such malice in mind, but all that seems to disappear as you see the immobilized mare.
"Ah Applejack, I think it suits you."
>She doesn't answer. They've taken the liberty of gagging her as well.
"You know you seemed to enjoy yourself an awful lot with Rainbow Dash."
>A blush creeps up on her face.
"If you'd like I can give you that feeling again."
>The bit keeps her from replying, but you can tell the idea is rather unpleasant to her. All the better for you though.
>You position yourself behind her. If earlier is any indication, you won't even need a cock for this.
>You begin by slowly massaging her thighs.
>Muscle and tension knots greet you, but you you grind inward and do your best to soothe her.
>You switch between slow sensual rubbing to a deep massage and back again.
>10 minutes pass and you're beginning to wonder if you've made any difference at all.
>20 minutes and still silence..
>At 30 minutes, Applejack forgets herself and lets out a high pitched, shaky sigh through her gag.
>Ha! You are getting through to her.
>Her head bobs upward as she realizes her mistake.
>But the realization comes too late. She's already shown her hand, and you take the opportunity to slowly move your massage inward till you're just a hair away from her hole.
>You don't so much as even brush against it though. You stay just shy and continue massaging the outer areas until...
>The tiniest bit of fluid starts to accumulate.
>You smile. She's getting wet.
Your work moves to her lips now and her legs nearly buckle as you touch her the first time, but she quickly gets used it.
>Until you slip a finger inside.
>Her cunt is hotter than you would have thought. It's definitely radiating more heat that Rainbow Dash's. But it isn't unpleasant. It's sultry in a different way, beckoning you forth.
>She lets out a throaty squeal as you push inward.
>And she let's out a groan as you pull out.
>You begin to work her insides with a bit more fervency.
>Shit, she's really starting to drip now. You saw it happen earlier, but experiencing it first hand is much different.
>For one you're the cause this time.
>You finger slips in out with ease now. One finger pulls out and two go in.
>She's caught between halfway groaning and fully moaning now.
>You find a spot that she seems to enjoy more than the rest and concentrate your efforts there.
>Her legs begin shaking and her cries become shorter. She's close. You know it. It's the same noises she made earlier.
>You concentrate your efforts just a little bit more and...
>Stop.
>You pull out and her ass shakes instinctively searching for the source of it's previous pleasure.
>Applejack lets a out a yearning cry.
>You plunge your fingers back inside her sopping hole.
>She clenches around you as you begin your thrusts anew.
>You have to play this very carefully. You aren't a mind reader and the slightest miscalculation could ruin the whole thing.
>But you concentrate hard at the task at hand. You can do this. Just listen intently to her breathing and when it becomes the slightest bit erratic...
> You pull out and stop again.
"Hrmmmpppph!" Applejack grunts in frustration.
>Another well timed denial.
>After a few minutes of gentle massaging, you slip yourself back inside.
>More moans and whimpering cries of frustration as you build her back up and stop just short of release.
>Again and again you bring your little mare to brink and again and again you deny her.
>You glance at the clock on the wall. Shit... It's nearly morning. You've been playing with your little mare all night. Nightmare Moon will expect you in just a few hours.
>You slip your fingers out of her one final time and walk around to see the look on her face.
>Her eyes are rolled back slightly and she's drooling through her gag.
>You carefully slide the bit out of her mouth.
"So hot. Please. Just finish. I can't... I don't know. It's... Please. Augh."
>Her legs shake softly as she her body twitches.
>You silence her ramblings with a kiss and to your delight, she returns it with enthusiasm.
>She laps at your mouth hungrily, hoping to find her release at the back of your throat.
>But you pull away and replace the bit.
>You've been up all night with this. It's time you get take your enjoyment.
>Unfortunately, if you put yourself inside her pussy, she'll definitely be able to cum before you.
>Good thing she has another hole.
>You rub your cock against her dripping pussy, smearing it with her juices.
>She's tenses up slightly, but doesn't try to shake you off. You think she's honestly ready for you to take her virginity.
>Too bad.
>You slide your tip inside her other hole.
>She definitely was not expecting this.
"Hrph? Hm. Ahrph?"
>She lets out a few confused grunts like she honestly thinks you just made a mistake.
>You show her you didn't as you slowly push yourself inside.
>Taking your fingers you work her pussy a little, wiping the excess moisture on the exposed parts of your cock for better lubrication.
"You're a farmer right? Surely you've seen your animals rut before, but I bet you've never experienced this have you?"
"Ngh ughn," she responds through her gag.
>The fact that she actually responded to your question screams that you are making tremendous headway with the young mare.
>Smiling you push yourself to the hilt and stop.
>But fuck, the angle that you have to do this is really uncomfortable.
>You endure though. It's not like the pleasure isn't outweighing the contortion you have to put your body through.
>As you being to pull back, you feel her squeezing you trying to suck you back in.
>You're more than happy to oblige.
>You push yourself back inside, picking up the slightest amount of speed.
>More groans of uncertainty from your pet. But she doesn't sound too displeased by the intrusion anymore.
>You've given her enough time to get used to you. It's time to really pick up your pace.
>And so you do, moving your hips passionately back and forth.
>She's really clenching down on you. It's not unpleasant, but the pressure is more than you're used too.
>You can't keep this pace for too long, she feels too good.
>As you begin to reach your finish, you start to hear her breathe becoming ragged again.
>Oh... This would be too perfect.
"You know you can fight me all you want Applejack, but your body knows the truth. You like this. You want this."
>She whines out what is probably a "No," but it's inaudible through the bit.
>You decide to roll with it though.
"No? Alright then."
>You suddenly halt all action and pull out with a small pop.
>You're so close it actually hurts a little, but it looks like she was even closer.
>She begins to thrash violently against her restraints.
>The spreader bar holds her firmly in place, but she stretches all the leeway it can muster by picking up her leg and tapping the ground.
"What's wrong? I thought you said no."
>She snivels a cry of yearning in response.
"Well which is it Applejack?"
>You remove the drool covered bit from her mouth.
"Yeeees. Alright. Yes. Please. Just. Augh!"
>She shakes again and taps her foot on the ground
"Tell me Applejack, what would you do if a pig roamed into your house, bringing their mud and filth in with them."
>She doesn't answer.
"You'd turn them out of course. Because animals are useful. Animals are cute. But they aren't civilized. They can't control themselves."
>Her ears perk up and then flatten to the side of her head. She's honestly confused at where you're going with this train of thought.
"My point dear Applejack, is that to me you're an animal. You're an intelligent one, but an animal nonetheless. You can't control yourself. And you don't really know what's in your best interest
"Look at Rainbow Dash. She immediately got what she should do. And she even tried to tell you. But you haven't listened, because you don't know what's best for yourself. You need guidance. You need an owner to lead you."
>Her body twitches again and she taps her foot again. Her eyes are so unsure of the new turn of events
>You sigh and head to your wall.
>A lot of toys, some that look like they'll really cause some damage. But they don't concern you right now. Right now you're interested in...
>There, a plug that just slightly bigger than your girth. This will do just fine
>You have work to do. This will be the only company she has while you're away.
>You feel the affects of no sleep as you slunk in from your day. You were already tired to begin with, but now your eyelids are heavy leaden bricks.
>But your work days haven't been in vain. You are becoming well known throughout the kingdom and whenever you show up at a situation, it quickly dissipates.
>The ponies of Equestria are growing used to you, growing used to obeying your commands.
>But that's a thought for a different time. Right now, you have to take care of yourself. And that means sleep. No training tonight. If you get another sleepless night, you're certain if anybody musters the courage to challenge you, they'll take you out with little effort.
>As you enter your room, but don't so much as glance at Applejack. She might as well be part of the decorum for all the shits you give right now.
>But nevertheless, you can feel her eyes watching you. And as you sit on your bed to strip, you can't help but let your eyes fall on her.
>Her face is pleading for something, but you refuse to acknowledge her.
>Sleep. Blissful sleep.
>Consciousness, angry wakefulness.
>You open your eyes to heavy neighing.
>As you struggle to adjust your eyes, you see that only about 6 hours have passed. You need more. Fucking Hell, that isn't nearly enough to catch you up.
>But the neighing doesn't stop.
>You groan outwardly as you force yourself up. It's only 1 am. You could sleep another 8 hours if somepony would just be quiet.
>Walking over to Applejack, you try to figure out what suddenly has her so energetic.
>She just looks at you with the same pleading face she had when you went to bed.
>Walking behind her to to examine her plug, you find the cause of distress.
>She's sopping wet, so much so that's its dribbling down her legs.
>Suddenly you are very aware of the fact that you didn't get to finish earlier.
>But if you give in and take her, you'll be giving her exactly what she wants.
>Release.
>You can't have that.
>You massage Applejack's thigh lovingly as consider your options.
>No. Not tonight. She hasn't had enough yet. She needs more before she's ready.
>And honestly you just want to sleep anyway. Fuck, you're tired to the point that your eyes hurt a little bit.
>You could probably just stay in one of the empty rooms reserved for the three yet broken ponies, but that sounds a little boring.
>Besides its been some time since you really interacted with Fluttershy.
>You've checked in on her of course, but extended activity was limited in favor of other things.
>You slap Applejack's behind lightly.
"If you won't be quiet, then stay here alone and I'll deal with you later."
>She softly whines as you leave the room.
>You make your way over to Fluttershy's room and upon entering find that she's still awake sitting on her bed and just staring at the floor.
>She meeps at the unexpected intrusion but immediately jumps down and runs down to sit at your feet.
>You've really left an impression on her.
>You're suddenly glad you broke her with fear and compassion rather than pain and humiliation.
"Fluttershy why are you up? It's late. You should be asleep."
>She quivers into your leg as she realizes she's messed up.
>You've chosen your words badly. Of course any critique will shake her.
"I... I'm worried. About. My friends," she says quietly.
"You're friends are fine, pet. You've been so good that no harm has needed to come to them. In fact, Rarity and Rainbow Dash are right across the way. The others will join them shortly and you can all be together. I promise"
>Her ears stick up and she her tail flicks around happily.
"Right now though, it's just you and me and I've had a rough couple of days. I'm using your bed to sleep as mine... has some issues that will be worked out later."
>She nods happily, her body still pooled around feet.
"This means I need the use of my legs, Fluttershy."
>She lets out another scared cry as she backs off.
>Normally you'd use this as an excuse to take charge and have a little fun, but the bed is calling to you.
>And while it obviously isn't as luxurious as yours, you don't care. You could probably sleep on rocks right now.
>Fluttershy follows shortly after and maneuvers into a sitting position on the floor at your side. She rests her gaze on your chest, not daring to look at your face.
>The bed is small, but she could probably squeeze in at the bottom if you wanted.
>You want.
>Once you situate yourself into a comfortable position, you pat the area around your legs.
>She understands and happily obeys, carefully climbing on and finding a spot that doesn't put her entire weight on your lower half.
>She does a pretty good job of not disturbing your comfort and you relish in the warmth she creates.
"I don't have my alarm in here. So you'll have to do Fluttershy. I want to wake up at 7 alright? Not 6.59 and not 7.01. Seven."
>She nods as you smile and close your eyes giving yourself over to sleep once again.