Twilight, Princess of Shadows

by Estrus Season

Chapter 3 - Pain and Pleasure

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Twilight was getting a massage by one of the handful of servants that weren’t pressed into service and sent off to war, and she was thoroughly enjoying it. Now this is the life. Sooo much better then living in a cave. Then Sombra strolled in. “So how’d it go?”

“We won of course. Celestia and her army fled and we now have a foothold to the south. Now I’m going to go see if I can loosen our guest’s tongue.”


Shining sat in his cell in the dungeon. He knew what was going to happen and spent his time trying to prepare himself for whatever Sombra threw at him. He heard hoofsteps approaching, and then Sombra and two guards appeared. They opened his cell, grabbed him, and dragged him out to an interrogation room. Although he struggled it was a futile effort. When they arrived Sombra opened the door and they went in. Shining noticed a table off to the side against the wall with what looked like various instruments of torture laid out on it and a crystal chair in the center of the room attached to the floor. Shining was tied to the chair with his forelegs behind his back and his hind legs to the chair legs. After the guards left Sombra walked up to Shining.

“Well how about we save ourselves a lot of time and trouble and you just tell me what I want to know.”

“Fuck you.”

Sombra gave Shining the back of his hoof right were the armor was and Shining spit some blood on the floor. “I can see you’re going to be difficult.”

Sombra went over to the table, grabbed a syringe and a vile with some kind of liquid in it, and extracted some of it. “What’s that?”

“Just a poison, but don’t worry it’s not lethal in small doses. Although by the time this is over you’ll wish it was. It’ll just make your insides feel like they’re on fire for a little while. I can of course administer the antidote at any time but that’s entirely up to you.”

Sombra walked over to him and Shining tried to struggle but was too tightly bound. Sombra stuck the needle in his neck and after a moment it felt like his blood was beginning to boil inside of him getting worse as it spread through his body and to his major organs.

“AHHH…AHHHHH…AHHHHHHHHHHHHHHHH!”


(The next day)

After her defeat Celestia went back to Canterlot and left most of her remaining forces behind to try and fortify a position to keep the empires forces from advancing any further. She was currently talking to some of her officers in the guard.

“What’s are current situation regarding recruitment?”

“Recruiters have been sent across Equestria and we’ve started the drafting process. But it will still be some time before the new recruits are in battle ready condition.”

“Time we may not have. Lieutenant Strong Hoof you’ll be filling in for Shining Armor until further notice.”

“Yes your highness but it just doesn’t feel right not trying to rescue him.”

“We’re still licking our wounds from the last fight. We are in no position to mount an offensive or attempt a rescue. But the captain is a stallion of impeccable character and I’m confident he won’t give up any useful information even under the most extreme conditions.”


Twilight was brushing her mane in her room when Sombra entered looking none too pleased. “The captain’s fortitude is most impressive. Hours of torture and he hasn’t given up anything.”

Twilight put down her brush and got up. “Perhaps we need a different approach. You catch more flies with honey as the saying goes. Allow me to take a crack at him.”

“Be my guest.”

Twilight made her way to the interrogation room Shining was being held in. Once she got there she opened the door and got a good look at her father’s handiwork. Shining had some bruises and cuts in various places along with some blood staining his coat, and was taking slow steady breathes. She also noticed some urine on the floor but that wasn’t too surprising, it’s not like he could get up to use the bathroom or anything. Overall he wasn’t in too bad a shape. Luckily Sombra hadn’t tried to disfigure him or anything. He looked up to see her as she walked in and closed the door behind her.

“What do you want?”

“I’d like to discuss some things with you.”

“I’ve got nothing to say to you.”

“Honestly Shining your stubbornness is only making things worse for you. You know it’s not too late to change your mind and join us. Come on do it for your little sis.”

He gave her an angry look. “You’re not my sister.”

She smiled a little. “I’m glad you think so.” She went over and took a seat on his lap facing him. She gave him that sultry look again. “Tell me Shining when was the last time you’ve been with a mare?”

Shining’s look quickly turned to a puzzled one. “What?! T-That’s none of your business.”

“Hmmm have you ever been with a mare?”

“I-I-I have.”

“You know you’re a terrible liar. I find this surprising actually.”

“I’ve just been more focused on my career.”

“Still, with your good looks,” she said while caressing his face. “Strong physique,” she said while rubbing his chest. “And magical ability I thought the mares would be swooning over you.” Shining was getting more and more uncomfortable by the second. To make matters worse she was sitting right on his groin and could feel the heat building in her loins. “Something the matter, you look tense.”

Dammit Shining she’s your sister. Think of something, think of something.

“Perhaps I can help relieve that.” By now Shining’s heart was racing and his breathing had picked up. Then it happened, in an involuntary action his cock began to emerge from his sheath and poked her. “Somepony getting a little aroused are they.” Shining just bit his lip and then Twilight kissed him on the lips. She could taste blood but didn’t care. She broke the kiss and slid back a little to get a look at his growing erection. She stroked it a little to help it reach full mast. “Now I know the mares would’ve been lining up if they knew you’ve been hiding this between your legs.”

“Twilight stop.”

“Don’t pretend you don’t want to. This is my first time too but that doesn’t mean I haven’t studied the subject.” Twilight backed up off him, she leaned down to his cock and took a long lick from base to tip. Shining was fidgeting in his seat. “Getting a little impatient are we.” Shining just gritted his teeth and tried to block out what was happening. Twilight could smell his musk and gave it a couple more licks before wrapping her mouth around the tip and started blowing him. It was taking all of Shining’s willpower to keep from moaning or anything else that would indicate he was enjoying it. Twilight went lower and lower as time went on. After about a minute she stopped and pulled back. She went up and positioned herself right above his member. He looked over and saw a few droplets on the floor where she had been standing. “Time for the main event.”

She began lowering herself on to him and with a little pressure it slid into her pussy and she continued down. Twilight let a moan and after she made it half way down Shining couldn’t hold it in any longer and let out a loud moan. Twilight had cast a contraception spell on herself beforehand not wanting to take any chances. Finally she bottomed out and stayed there for a second before she rose back up and went down. She started riding him slow at first picking up speed every so often. Both of them were making various pleasurable sounds that kept increasing in volume. Shining was beginning lose himself. He had masturbated before but this was something else entirely. Any lingering pain from earlier had melted away.

“Ah fuck!”

“Enjoying yourself are you.” Twilight kept at it and started going faster, harder, and rougher. Shining could feel the pressure building in his balls and knew it was only a matter of time. Then he let out a primal cry of pleasure and started unloading inside her. Twilight kept going but the added sensation of him cumming helped push her over the edge and she let out a loud moan during her own orgasm. They both started to calm down a few moments later and were panting heavily. Twilight leaned in and kissed Shining passionately, her tongue invading his mouth. She pulled back leaving a trail of saliva between them. “I’ll leave you be for now and comeback later.”

Twilight lifted herself off his softening dick and turned around making sure to brush her tail under his chin. Her first couple of steps were wobbly but she managed to recover and walked out normally. Having not slept in who knows how long fatigue finally caught up with him and he passed out soon after.

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