With the basics

Kaitlyn chuckled. "So, what do you think?" she asked.

George didn't know what to say. He was nervous. His heart was pounding in his chest.

"Let's start slow," she suggested. "Take off your clothes."

George blushed, but he undressed. He was naked, and his cock was erect in front of her.

"Spread your legs," she ordered. "Show me your cock."

He did.

"How does that feel?" she asked.

"Odd," he replied.

"I bet you feel odd," she said. "Stand straight."

He did.

"Now, lie down on your stomach," she commanded.

His eyes opened wide.

"Lie down," she repeated. "On your stomach."

He obeyed.

"Put your hands behind your head," she instructed.

He did that.

"Yes, Mistress Kaitlyn," he said obediently.

"Good boy," she complimented him. "Now, reach down and grab your ankles."

He did that, too.

"Do you feel odd?" she asked.

"Yes, Mistress Kaitlyn," he answered.

"Good boy," she said. "That's what I want to hear."

"Are you going to hit me?" he asked.

"Not today," she replied.

"Please don't whip me," he begged. "I beg you, Mistress Kaitlyn."

"I'm not whipping you," Kaitlyn said. "I'm training you."

"I beg you..." he started to say again.

"Just listen," she scolded him. "I'm in charge here. You will obey me."

"I'm sorry," he whispered.

"You have nothing to be sorry for," she reassured him. "It's perfectly natural to be afraid. But this is something you must learn to control."

"I'm scared, Mistress Kaitlyn," he said.

"I understand," she said. "But you've come a long way already, haven't you? Just remember that."

"Yes, Mistress Kaitlyn," he replied. "I will."

"Good boy," she said. "Now, stand up."

He stood up and looked at me.

"Turn around," she said. "I want to see you."

He turned around, and she saw his ass. It was nice and firm.

"Nice," she commented. "You have a great ass."

"Thank you, Mistress Kaitlyn," he said.

"I'm going to work on your racing skills," she explained. "We don't have time to go very fast, but I'd like to be able to teach you to run faster."

"Yes, Mistress Kaitlyn," he replied.

"First things first, though," she said. "Let's get you saddled."

He smiled. "Yes, Mistress Kaitlyn," he said.

"Come here," she told him.

He walked over to her, and she led him by the hand to a mounting block. She took his cock leash and attached it to him, then took the other end and attached it to a ring on the wall. Then she fitted the saddle gear onto him, with nipple reins, ball compressors, and handlebar, as well as several pouches containing various accessories that hung down from the saddle. Then they got his ponyboots on.

"Do you know what this is?" she asked.

"It's a mounting block," he replied.

"Right," she said. "And I'm going to use it to ride you now."

"Yes, Mistress Kaitlyn," he said.

"Lean forward," she ordered.

He leaned over in front of the block and presented himself to me.

"That's a good boy," she praised him. "Now, sit back."

He sat back, and she mounted him from behind. She made sure that he felt comfortable before she began to move.

"Start walking," she ordered. "Like the good ponyboy you are."

He walked, and she rode him.

"Now trot," she instructed.

He trotted, and she rode along.

She activated the compressors harshly, squeezing his balls. She knew he wasn't used to it.

"Ow!" he cried out. "Mistress Kaitlyn! Please!"

"That means you're supposed to run faster. I will use them when other kinds of motivation aren't working or you get distracted."

"Yes, Mistress Kaitlyn," George replied.

She squeezed his balls again, and he jogged faster.

"Keep going," she ordered.

He went faster.

"That's better," she said. "Now canter."

He cantered.

"And gallop."

He galloped.

"Excellent," she said. "When you're ready, let's try two laps around the track."

***

The next day, a crowd had gathered for the Queen's Race. They were curious to see George and whether Kaitlyn had been able to turn him into a proper ponyboy in the two weeks she had been given.

There were no spectators in the stands yet, but the royal palace was packed. Kaitlyn was standing on the starting line, while Mary was in the audience, near the front. As promised, she was wearing a skimpy bikini. It was pale pink with black trim. The top was cut low, showing off her breasts, and the bottom was so small that it barely covered her pussy. She wore knee-high boots with heels. Her hair was tied up in a ponytail.

Kaitlyn waited on the starting lines for George. He was dressed identically to the previous day. He had his cock leash on, and he was wearing a harness with nipple reins, compressors, and a handlebar. He also wore his ponyboots. He was led onto the racetrack by the Lady Commander, who held his leash. She walked proudly in her uniform, which consisted of a light blue sash with a bright yellow stripe, a matching pair of shorts, and knee-high boots. Her breasts were completely exposed by her cupless bra, and they bounced wildly with each step.

The crowd cheered as George entered the racetrack. When he arrived on the starting line, Kaitlyn removed his cock leash, passing it to the Lady Commander for safekeeping, and mounted him. She noticed his wedding ring buzzing gently. That was one way for Mary to help him. Whenever she liked what she saw, she could operate her remote to control the ring, making the vibrations stronger.

Kaitlyn was wearing the skimpy purple silk outfit that had been provided for the event. It consisted of a thong that ties around the waist, a micro-mini skirt, and a halter top that buttons from the neck down. It showed a lot of cleavage. There were thin straps that hang down from the top of the halter, holding the breast cups in place. The skimpy outfit would have been embarrassing, but purple was the Queen's color, so she wore it with pride.

"Ready, George?" she asked.

"Yes, Mistress Kaitlyn," he replied.

"You look great," she told him. "I'm really happy that you're doing this."

"Thank you, Mistress Kaitlyn," he said. "This is all because of you."

"I'm glad you're enjoying yourself," Kaitlyn replied. "There are just a couple of minutes left before the race begins." They looked to the sides and saw one team on either side of us. Each team consisted of one male ponyboy and a female rider. Both teams had their own saddle with nipple reins, compression devices, and handlebar. The men were naked. They didn't have rings on their cocks, so they clearly weren't engaged or married. She recognized one of the other riders as Katrina, who grinned at me. She was wearing the same outfit as Kaitlyn, although hers was bright red and a little tighter.

"Get ready," she told George. "We'll start in a minute."

George nodded.

George recognized Katrina's muscular ponyboy as John, who he had met when he was awaiting the Queen's judgment. The two ponyboy's nodded at each other politely.

John remarked, "Wow, you've really turned him into a real ponyboy, haven't you?"

"Yes, John," Kaitlyn agreed. "He's getting quite good at it, I think."

George kept nodding.

Kaitlyn didn't recognize the other rider, but she was very attractive. She suspected that she was a commoner because her outfit wasn't nearly as revealing as her own. She wore a black leather body suit with white trim. It was tight, but not obscenely so. Her ponyboy was naked, but he had a long black tail extending from his ass. His enormous cock was hard and erect. She couldn't tell if he was aroused by the sight of her or not. Perhaps he was being vibed by the tail.

The Lady Commander, acting as announcer for the race, introduced Kaitlyn. "As you know, the races for today are a bit different than usual. Our contestants are being judged not only on speed, but on how closely they adhere to the traditions of ponyboy riding." Kaitlyn smiled at the crowd, knowing that they wanted to hear more about George.

"Our first contestant is Mistress Kaitlyn, who has been training George in the ways of ponyboy racing."

"Oh yeah!" someone shouted.

"Yes, ma'am," Kaitlyn agreed. "I'm glad you approve of my methods."

"Go for it," she encouraged me.

"Thank you," she said. "Our second contestant is Mistress Katrina, who is new to ponyboy riding, but her ponyboy is a seasoned veteran."

Katrina winked at Kaitlyn.

"And our third rider is Mistress Viola, who recently won the Queen's Race. She is here to show the citizens of the Queendom what a true ponyboy looks like."

Kaitlyn could feel herself blush.

"Now, the Queen has decreed that today's race will have four laps, instead of the usual three."

"Good luck!" Galena encouraged Kaitlyn from the audience. The Queen announced at the race was to begin.

"Thanks," Kaitlyn replied. "Let's go."