Pipsqueak the Guard
It had been nearly 20 years since the Caribou established a new order across Equestria. New generations came in and the culture continued with minimal resistance aside from the occasional rebel that had yet to be caught. No need to convert the newer generations as they're raised to be good sluts from the beginning while the males make fine warriors or craftsmen. Some males enjoyed laying down the law on a rebellious cunt, but there were thousands of black collars left.
Some were even thought to be immortal, such as Princess Luna. It made her popular with the guards of the King. However lately she had been showing signs that perhaps she would finally break. Maybe a purple collar would be put on her soon. But for now she was chained to the wall outside the guard's chamber complex like she was every summer, awaiting her next male.
Pipsqueak inside the chamber took off his helmet after a long day's work. As head of the guards he had many duties such as making sure slaves kept attending the plants or that other guards weren't TOO busy fucking females. He was always shocked that he was made head of the guard merely a yesterday. The king did stress something about the "enthusiasm of the younger generations" being a good example for "preservation of their livelihood" or some political squabble like that.
It is true that Pipsqueak was very loyal to the king. The king had improved life in ponyville for him ever since he arrived. Not only did his small size as a child no longer matter, certain bitches like Diamond Tiara were a lot less demeaning. Then in high school he was able to make sure Diamond Tiara knew her place as a female and was able to make her a purple collar by college. Ever since then he had a reputation as the "Great Converter" as he was able to make at least 5 red collars and 1 more purple collar from previous black collared mares. Indeed things have been at peace far better since the King took control as opposed to the alicorn princesses' rule.
He took off his armor and was sitting naked in front of a mirror. He certainly wasn't a pipsqueak by high school and was now perhaps the most athletically fit male in the castle with the muscles and strength to prove it. He was taller than most as well. While his height came naturally, his muscular body and strength came through determination. He was going to show he wasn't the male to be pushed around like in the past. It had proven successful and so he was always proud at his accomplishments, as vain as they are. He'll walk around the castle on summer evenings completely naked at times when off-duty because he could. Not to mention the red collars were extra excited when he was like that. Perhaps it was due to that his cock could be seen straight away as opposed to inside clothing and armor. He certainly wasn't a pipsqueak where it counted either. Not that the females should care.
He walked outside the chambers naked and saw Princess Luna. For the longest time he avoided fucking her. Maybe there was a tiny hint of respect for her? She did used to be his favorite princess. But loyalty was surely gone and she was very beautiful. The temptation to finally fuck her grew. If she were a red collar it would be amazing. If a purple collar, even better. The hottest palace cunt eager to please him and knowing no other thoughts; the perfect toy for him.
"Hello Luna." he said to the ex-princess whose face was full of confusion, signs of being very tired, sadness, bitterness, and the occasional dry spot of cum. Luna didn't respond except by barely moving her eyes to his direction. Still stubborn like any other black collar.
"You will respond to a male like good cunts should." he said to her. The command fell on deaf ears. He shrugged and sat down next to her. He was ready for a challenge with this one. He won over four black-collars and made them red by his smooth talking and charisma. The fifth was more...forced, but still a success. "Perhaps you will serve better with a minor rest?"
The princess' eyes widened a tiny bit. No one had offered her anything remotely decent in 20 years and it seemed like a trap. It was in a way. She tried to say something but couldn't. Not only was she tired but her throat was dry from lack of water in the day so far. Once-a-day rations were harsh. But she wouldn't give in just for a bit more food and drink so far. But 20 years of deprivation took a toll on her psyche. She barely nodded her head then flinched expecting to get beaten. Pipsqueak didn't touch her.
"Don't worry, I won't hurt you." he said as he stood up, "I want my cunts to be good cunts but also effective. Red collars get extra food, water, and rest because they are willing to please their males." Luna looked down in sadness. She had many thoughts go through her head. There was no rebellion or outside help like she had hoped. Perhaps resistance really was futile. In a way, seeing a pony care for her for the first time in decades made her want to help him in a way. But she felt too conflicted to rebel or surrender.
"All you have to do is give me one blowjob." he soothes as he gives himself a handjob, "Just one. That's all you have to do and then I promise that I'll get you a new red collar and make sure you get a day's rest." Luna sank to the floor further. Mixed messages flew in her mind. 20 years of propaganda, conditioning, torment, rape, and now Pipsqueak's kindness were winning in her mind. All she had to do was perform her duty, that was all. Then she'd be spoiled with rest and finally earn the generosity of a decent set of meals. She'd be treated like the other princesses and get the ability to adore the masses again through her submission, her example.
"C'mon." urged Pipsqueak as his hard cock was made erect over her head. "One blowjob from my favorite princess." He smiled and stroked her hair. Princess Luna teared up and finally got the urge to say something as her mind broke in just the right way.
"Th-thank y-you..." she let out and sat up, "M-ma...master..." she then licked his tip and braced herself only to find that Pipsqueak wasn't forcing her forward. She then sucked on his cock and slowly moved forward looking up at him. He merely smiled and stroked her hair.
"See? You can be a good slut." he complimented, "I knew you'd find your place like every other cunt." Luna cried, but not out of despair like before. She was happy that she wasn't being abused. She was grateful. Then she was eager and sped up tremendously. Pipsqueak gently held onto her head and moaned loudly.
"Th-that's right you cunt!" he moaned. "Suck my cock." Luna moaned herself as she had the urge to finger herself. It felt nice to her despite it being a bit soar. Twenty years of forced fellatio gave her the experience to know what to do and she merely did what she was forcibly taught. He came down her throat as she licked him clean and swallowed every last drop. Compared to her kibble it tasted like sweet honey. Pipsqueak panted and sat in front of her.
"A-as promised, you get a red collar and a day's rest." he whispered while recovering. That was an amazing blowjob. He stood up and went inside the barracks. After a minute he came out with a red collar and put it on her, ripping up the black collar. Luna smiled and looked up at him.
"Thank you for such an honor master." she beamed. Pipsqueak gave her some water and stood her up before unchaining her. Another guard walked by to see the commotion.
"Whoa! Luna's finally a red!" he shouted to other guards while motioning them to come. Other guards came in congratulating Pip. One guard grabbed her ass before Pip struck him away.
"I'm not done with this bitch yet." he laughed. The other guards high-fived him and then cheered. The noise soon brought the king. As the king arrived they all turned around and bowed, including Luna.
"Very impressive Pipsqueak." he said with a voice showing signs of aging, "You finally broke our most prominent resistant." he walked up to Luna and stroked her ass. Luna blushed at the sight and by practical instinct her pussy widened slightly as she stood next to the king.
"You deserve a reward for this." the king proclaimed. "As we find accommodations for Luna to live with the other red-collared cunts so she can serve males like she was always meant to, she needs a place to stay since we have more black collars for the walls. For converting her, she is your personal cunt for two days, basically until the third sundown from now." Pipsqueak grinned and bowed.
"Thank you, your majesty."
"Rise and continue to be an amazing example on how to serve your king and country." concluded the king before walking off. On the way he saw a random red collar and suddenly leaped on her to fuck her. She moaned and submitted instantly. Several guards masturbated at the sight but by this point it was so common that most just ignored it. The guards left as Pipsqueak walked Luna to his quarters. As the captain, he had a large room enough for him and three cunts if necessary. He had Luna stand over a rug.
"You may rest here for the night, undisturbed." Pipsqueak said with the pride of being a man of his word. Luna merely responded by turning around and bending over to display her flank. Her pussy was wet with excitement.
"Would my master like a good fuck before bed?" she asked eagerly. Pipsqueak smiled and simply began fucking her. Luna moaned and was wet within a minute. "Thank you master!~"
"I'm impressed slut." he grunts as he speeds up, "You've improved so much in an hour." He grabbed onto her flank and pushed her towards a wall that she put her hands on. After a few more minutes of pleasure he came inside her. Luna soon after squirted her own cum from the delightful experience.
"That's what I call gratitude cunt." Pipsqueak complimented while stroking her hair. "Now rest, for after breakfast tomorrow you and I will do some more."
"Thank you master." said Luna before laying down and closing her eyes. She had the best sleep in perhaps 3,000 years.