A Nightmares Deal

by bakersong

Rating: mature
Tags: Nightmare Moon, Princess Luna, Original Character, Porn, Profanity, Non-consensual, Princess Celestia, Sex, Twilight Sparkle, Anthro, My Little Pony: Friendship is Magic, Second Person, Dark, Alternate Universe
Length: 4108

You help take down a terrorize/rebellion all to try to save your sister who had joined. Once deemed a hero by the queen she offers you a special deal.

After Nightmare Moon banished Celestia and named herself Queen several rebellion groups formed for the one and only purpose of stopping her. Your sister, Dawn Dew, was recruited into one of these groups which Nightmare had deemed as a terrorist. You turn them in after you were also invited to join as well in order to try to save Dawn.

Published 2021-07-27 15:10:01 UTC
Last updated 2021-07-27 15:10:01 UTC

The Rebellion

"Dawn you know you'll just get yourself killed right?" You yelled out at your sister, the only family you have left since Nightmare took over.

"I rather die a free mare than be a servant of that monster!" Dawn argued back.

You were furious at this point as you both knew that life has actually improved since Nightmare was crowned the one and only Queen of Equestria. Though Nightmare was far stricter and crueler in her punishments than what Celestia would have even thought of. That and the change of power started a rebellion, though as of recent times there are only a few rebellious groups left.

Your sister Dawn, had been approached by none other than Twilight Sparkle herself even though by approached you knew she meant she literally ran into the mare by complete accident. Both of you had been talking about if either of you could join the rebellion then you would, but you didn't think either one of you would actually do it. Though you agree with what the rebellion stands for, after the death of your mom you didn't want to take the chance of losing the only family you had left.

"Don't give me that look! You know I miss them too, but they would want us to live in peace and not in fear!" Dawn yelled but there was less anger in her voice. She stopped herself for a second to take some deep breaths as tears streamed down her cheeks. "I know we are the only family that we have left, but I want to do this for even the tiniest chance of winning. N-not to mention you never minded me giving them supplies..."

"Supplies is one thing but joining them is a whole other danger!" You yell clenching your eyes shut as you start feeling the tears start to form. Though you relax as you feel Dawn gently place a hand on your cheek making you open your eyes to meet her big loving and warm red eyes.

"The offer is still open for you too," Dawn suggested making you look away for a moment before giving a sigh.

"It is true, you can come with us and it might even be safer that way," Twilight who had remained silent throughout their argument, which you did appreciate, finally spoke up. You give her an angry look but you knew at this point you couldn't win.

"Fine, we'll go together," You said before storming off to your room to get ready, and Dawn gave a sigh of relief.

"You two are very close, reminds me of my relationship with my own brother," Twilight said with a sad twinge. Everypony knew Shining Armor was one of the first rebellion leaders to be caught and the first one that no pony knew what happened to. There were rumors that Nightmare kept some prisoners inside her own castle but no pony knows for sure though.

"We are, our father died when we were both young and our mom passed from cancer a week before Nightmares return," Dawn replied. "Their deaths are what made us all the more closer to each other. Also, don't worry about his anger he's just..."

"Overprotective? It only makes sense and I don't blame him. This is a very risky time for us," Twilight said. "Don't worry though, I'll talk to him when we get out of town and reassure him that we'll do everything we can to keep as many of our members safe."

"That's one thing I don't think you could guarantee," You say as you walk out of your room with a suitcase in tow.

"Is that all you're taking?" Dawn asked with a raised eyebrow.

"Yeah, just clothes, toothbrush, and a few books." You answer.

"That sounds like plenty to me, you two want a moment alone to say goodbye to your home?" Twilight asked making you take a breath.

"I think I'm good, thanks," You give the purple unicorn a weak smile making her nod to you.

"I think I'm good too," Dawn said after taking a moment to slowly spin around.

"Then let's get going, can't stay here for too long or else... well you know," Twilight said as she turned to take the lead.

As the three of you leave your childhood home you couldn't help but look Twilight over, and you couldn't help but find her very attractive. You could tell from the time you've spent with her already that she was smart, confident, talented with magic, not to mention she had a sexy librarian feel to her. That was even with the tight pants she was wearing, and a blue long sleeve shirt that also hugged her tightly leaving little to the imagination.

"Keep it in your pants, she has enough to deal with without you ogling her," Dawn said a bit louder than she intended making Twilight bust out laughing.

"I don't mind really, I mean your brother isn't bad-looking himself," Twilight said giving you a wink though there was something you noticed in her eyes you couldn't quite pin down, and from what you could tell it might have been a plan. But you could tell that no matter what it was you saw in her eyes it wasn't going to be fun.

"Uh, um, I-I'll um, k-keep looking then..." That only got more of a laugh from her, and as you walked she seemed to put an extra sway in her hips. Though as they got closer to town Twilight's horn lit up casting an illusion spell to change how she looked.

"Will that be enough to trick their defenses?" Dawn asked.

"Yups, how I get around so much despite the bounty. Also, I want to make a supply run in town and I want you Dawn to go get some fabrics, you are with me," Twilight said turning to you making you nod. "Also, call me Misty for the moment."

"Got it misty, try not to break him!" Dawn said as she started to walk ahead.

"Don't forget to meet us at the train station!" You call out making Dawn roll her eyes, though you couldn't see her do it you knew her well enough. After a moment and Dawn was out of earshot, Twilight stopped you in your tracks.

"Listen, I know your reputation and if you don't mind I have a plan in mind. One that could get us all killed, but I would like you to be the key to taking down Nightmare once and for all," Twilight said looking you right in the eye to see your response.

"You just convinced me to join, if just for my sister, and that's the first thing you say to me alone?" You ask anger seeping into your voice.

"I know, but I'm not afraid to say we are losing this war. This really may be the only way left to fix everything," Twilight replied, and as you both stared each other down you could tell she was serious.

"Fine, tell me this plan and I'll let you know," You say making the mare smile as she started to explain her plan.

Once she was done explaining she let you agree to think about it and the two of you went to pick up the supplies she wanted to get. After hearing her plan you knew part of you wanted to do it if it meant a chance of saving Dawn, but you pushed it to the back of your mind. You did have to help her carry some of the supplies, and of course, there was some teasing from the townspeople who knew you and saw you hanging with such a pretty mare.

"I think that's all we need!" Twilight said as she paid for a bag of nails. "Can't wait to build that new swing set for my niece!"

"Yeah, you say for the twelfth time," You said getting the cashier to chuckle.

"Oh come on, I said I would thank you! for helping me," Twilight said getting closer to you with a seductive look as she stood a bit on her tiptoes as she surprised you by locking lips with you. After a second she broke the kiss giving you a big smile and wink.

"Uh, y-yeah..." You couldn't really get anything else out, though you still had enough blood flowing to the right head to register Twilight started to walk away.

"You've got quite the catch there!" The cashier called out as you left the store.

"Um, that was nice," You say making Twilight giggle.

"What can I say? As far as anypony will tell is I'm your marefriend, kissing you only reinforces that idea. Not to mention, I meant what I said about you not being bad-looking yourself. Play your cards right and I'll kiss more than just your lips," Twilight said with a flirtatious smile, this made you shift to hide your very stiff member.

As the two of you walked to the train station you managed to calm your boner as you thought about the plan she told you. Though you didn't quite know exactly how it all would work it was highly dangerous no matter what. But if it succeeded Equestria would be completely free of the never-ending night. You break out of your own thoughts when you see Dawn waiting for you two at the station.

"There you two are! I've been waiting for like two whole minutes!" Dawn said with her normal bright smile.

"Sorry, we got just had to talk on our way over," Twilight joked as they approached. "Did you already get our tickets?"

"No, I was waiting for you two," Dawn said picking up her bags, and they all went to the ticket booth.

"Well, if it isn't the stunning Dawn!" The booth keeper said as they approached. "I see your brother came, and who might you be young miss?"

"I'm Misty Spray, nice to meet you!" Twilight said in a much more energetic voice.

"Good to meet ya, the name's Rusty, Rusty Spike," The stallion replied with a nod. "So, where are you three heading?"

"We're going to Midnight Valley, I told them about the statue of our Queen and how it has a special glow to it," Twilight said putting some Bits and slid it into the window hole. Rusty gave a smile nodded, and gave them their tickets.

"Have a lovely trip," Rusty said in a tone that might not have sounded weird unless you really knew him, and the realization of what it meant made you shiver a bit.

"Come on, let's go wait!" Dawn said excitedly and went to sit down at a bench far away from most of the public.

"So, you know Rusty huh?" You ask, making Dawn elbow you.

"I know lots of ponies," Was all Twilight said about it, and as you waited for her to speak again your thoughts turned back to that kiss, but you didn't linger on that for long as Twilight's plan came back to mind.

"What are you thinking about that's making you get that face?" Dawn asked making Twilight raise an eyebrow at you, though you could tell she couldn't read your expression like how Dawn did.

"Oh, you sure you want to know?" You ask making Dawn narrow her eyes. "Fine, before we came this way Misty here decided to kiss me."

"What?" Dawn asked with a smirk.

"It was something to do, and don't forget I did say if you played things right then I may kiss something else," Twilight winked at you making you go completely red as Dawn laughed like crazy.

After that, you three made some small talk, some ponies came and say hi, or the occasional one who wanted to flirt. The girls had a little fun with this one who was a real dick of a stallion, and it ended with the dude crying because they spilled one drop of juice on his shirt. It wasn't long before their train pulled up after that, picking up the bags they boarded the train.

The train wasn't crowded as it pulled off from the station and they went on their way. They knew the trip would be a three-hour trip and each of them pulled out their own things to do. Dawn pulled out a Word search, Twilight had a Crossords, and you brought out a normal book to read. Along with that you all once again make some small talk and shared another laugh at that stallion.

"We're almost there!" Dawn exclaimed, leaning out of the window making both you and Twilight look at her ass. Which Twilight quickly pinched making Dawn give a little ek. "Gee Misty, first kissing my brother now you're coming onto me. Might get a couple of ideas!"

"Hey, if you two are open for that kind of night," At that the girls laughed as you rolled your eyes. "Well, let's get ready to get off then and I'll show you the way!"

At that, they got their bags and felt the train start coming to a stop, and not too long after they were on their way. With Twilight leading the way it wasn't long before they left the small town behind without drawing attention to themselves. They made their way towards a statue of Nightmare Moon before varying off and instead they went towards the woods.

"Now, before we go on I need to make sure that both of you are a hundred percent certain this is what you want. After this moment you two may as well be dead as far as any old friends are concerned about," Twilight said once again meeting both of their eyes.

"Yeah, we're sure," You answer for the both of you, and Dawn nodded in agreement.

"Alright then, follow me," Twilight said only taking two steps before disappearing in between two trees, making you raise an eyebrow but neither you nor Dawn questioned it before stepping through.

"Wow!" Dawn said as the other end of the portal revealed a massive building.

"It's a lot bigger than it looks, it has six stories five of which are underground. Hence why it has yet to be discovered, and as for the portal only a few know about and how to activate it," Twilight said as she finally dropped her disguise.

"Welcome back Twilight," A small dragon said as he walked by in a rush.

"Nice to see you too Spike!" Twilight called out as the dragon disappeared. "He's very busy nowadays, now let me give you a basic tour."

Twilight then lead them all around the base, except for two of the lower floors. Though she did not miss a single opportunity to introduce them to everypony they ran into. She showed them their gym, and pool along with the cafeteria. After that, Twilight showed Dawn to her own room before taking you to your room.

"And don't worry about the supplies, I'll have somepony get them later," Twilight said as you put the supplies she had you carry down in a corner. "So, have you thought of my offer?"

"It's only been a few hours, so don't rush me okay?" You say making Twilight nod. "To answer you, I have been thinking about it."

"And?" Twilight asked.

"I am leaning towards agreeing for now," You answer before you start to unpack, though you quickly stopped when you felt someone tap your shoulder making you turn around.

"Just really consider it okay?" Twilight said as you turn to look at her.

"I am, now c-could you go so I won't be distracted?" You ask making Twilight raise an eyebrow.

"Oh, so how am I a distraction for you?" Twilight asked giving a little wink before something seemed to slip out of her pocket. "Ops!"

Twilight turned around to bend over and pick it up letting her tight pair of pants show off her nice round ass. You could feel your already stiffing dick only grow harder faster. She had done this kind of teasing since the day Dawn introduced you two when Twilight first started to talk them into joining.

"Why do you always tease me like that?" You ask out loud.

"Tease you?" Twilight replied giving you an innocent look as she stood up.

"You know exactly what I mean," You say crossing your arms making Twilight bite her lower lip in thought, but to you it was still sexy.

"What can I say except that I like you, I mean your very good-looking, and you put your family first which is very important for me," Twilight answered and you felt like she was telling the truth.

"You know I can't help but find you... hmm, let's go with sexy as hell," You say and at this point, you weren't even attempting to hide your now pitched tent. Which you could see Twilight glance at it from time to time.

"I-I think I'm gonna...EEP!" Before Twilight could say or do anything you reach out taking her by her hand and pulling her towards you and lock lips with her.

"That was for earlier, and this is for the teasing," You said as you break the kiss and grabbing her ass with your free hand.

"P-please, I-I may do a lot of t-teasing b-but if we g-go further..." Twilight started now looking away shyly. "T-this will b-be my f-first time..."

It took a few seconds to let that sink in and as it did you couldn't help but feel your dick throb at the thought of deflowering such a beautiful mare. Not to mention one of the most wanted ponies in all of Equestria was also a bit of a turn-on for you. You let go of her ass and place a hand on her cheek.

"Before this goes further, are you sure you want me to be your first?" You ask as you locked eyes with her, which she replied with a light kiss and you let out a moan as she rubbed her hand over your dick through your pants.

"I am very sure," Twilight whispered into your ear, though as soon as she said that you quickly turned her around pushing her down onto your bed.

"Good, because I am very sure I want to fuck you so much," You say finally getting the chance to relieve your frustrations from all of her teasing. As you say that you move towards Twilight locking lips yet again giving her a passionate and loving kiss.

Twilight responded with just as much passion and as you two kiss you let your hands really explore her. As your hands explore you let one stop at one of her boobs fondling it making Twilight break the kiss to moan, which only increase as you kissed her neck and nibbled at her. Not to mention your other hand was now tracing her lower lips on the outside of her pants.

"N-now whose... Ah!... teasing?" Twilight asked making you stop your kissing to give her a little smile.

"I got to get payback somehow," You joke and as Twilight tried to speak again you give her boob a firm squeeze making her give a little moan. As you continued playing with her tit, you use your other hand to undo her pants and slip in giving you a bit more of a direct way to her pussy.

"Fffuuucckk!" Twilight moaned out as you started to give her more direct attention, and hearing the mare moan was driving you crazy. But this was her first time so you wanted to make it as memorable as possible even if it meant waiting a bit longer.

As you continued Twilight stopped you for a second to take off her shirt revealing her light blue bra that covered her perky A-cup breast. She also slid her pants off letting you see her also blue thong she was wearing. As you looked over her more exposed body you practically growled from the need to just take her.

"L-like what y-you see?" Twilight asked making you lock eyes with her which was enough to send a shiver down her. "Well, what are you waiting for?"

Although you knew she meant for you to take your clothes off you instead put your attention back onto her. Twilight gave a surprised moan as you place your finger back onto her slit and started to trace it again. Though you knew Twilight would grow tired of you just tracing her, so you quickly pull her thong to the side to gently and slowly insert the first finger into her.

"Yyeess..." Twilight moaned as you go into a rhythm, and even adding another finger making her go crazy. It wasn't long after you could feel her clamp down onto your fingers as she started getting closer to cumming.

"How does it feel?" You ask and the only reply you got was a loud moan as her dam finally broke.

"T-that w-was..." Twilight couldn't finish speaking for a moment as she was breathing heavily. "Y-you m-made me c-cum that hard j-just f-from your fingers?"

"I have some experience," You tell her as you give her a kiss, and as you break it you two lock eyes.

"I-I'm ready f-for you..." Twilight said as she placed both of her hands onto your face, grasping you lovingly before giving you a very loving kiss making you grind against her. "Y-you feel so big even through your jeans!"

"You ready to see it?" You ask making her look at you like you were crazy this got you to laugh. You quickly take your shirt off, and with your pants, you wanted to give her more of a show. Lowering them as slowly as you could making Twilight bite her lip in anticipation.

"By Celestia..." Twilight cooed out as you finally fully drop your pant revealing your hard member, her eyes wide. "I-I don't k-know how that's g-going to fit i-in me?"

"Only one way to find out," You say as you pull her now soaked thong from her before moving up to kiss her to get her to relax a bit.

"Aaahhh!" Twilight suddenly moaned out as the tip of your dick pressed against her pussy lips. With a bit of fear in her eyes, she spoke up again. "P-please, b-be really careful... FffffUUUUCCKK!"

She screamed out in mostly pain as you insert yourself into her, and though it was just past the tip you almost came just from the tightness. You didn't press further in letting you both grow accustomed to each other, Twilight had a few tears forming at the corner of her eyes. But after a minute or two, she nodded letting you know you could push forward a bit more.

"AAAAHHHH!" Twilight screamed out as you gave a big thrust causing her to dig her nails into your back. You once again nearly blew your load again, and as you were trying to keep yourself from cumming you wipe some tears from Twilight.

"S-sorry, but y-you know w-what they say a-about bandaids," You managed to get out making Twilight give a tiny chuckle and nod. You once again gently kiss her which of course turned passionate and before both of you knew it you started to go in a rhythmic and experienced in and out motion.

As you continued you noticed Twilight started to get more relaxed and her moans grew louder and more filled with pleasure rather than pain. You couldn't help but keep looking at her as you thrust into her as the sounds and faces really turned you on even more. Though you were slightly disappointed you hadn't taken off her bra before, so you managed to do just that letting her tits freely jiggle as you thrust.

"I'M CUMMING!" Twilight screamed out, though you weren't going to stop your rhythm even with how tightly she was clamping down on you. This not only made her orgasm seem to last longer but brought you to your edge to where you were ready to pull out.

"Hey, I was coming...." Suddenly Dawn was standing in the door her eyes going wide, though her entrance surprised you enough to make you thrust back into Twilight.

"FFFUUUCCKK!" You moaned out as you released into Twilight tight tunnel which sent the unicorn back over the edge.

"I-I..." Dawn started still in shock at the scene before her before she turned around and rushed out of the door, and luckily had enough sense of mind to close it on her way out.