Challenging

Kaitlyn pulled the nipple reins, and they began to run. Her ponyboy ran under her, and she guided him over the obstacles that had been placed on the racetrack.

"Go right," she ordered, pulling his right nipple rein.

They went right, and he jumped over the obstacle.

"Left," she commanded, pulling his left nipple rein.

They circled around the left side of the racetrack.

"Over there," Kaitlyn instructed him.

His legs carried him over to the side, and he jumped over the obstacle.

"Good job," she commended him, massaging his cock with her stockinged feet to reward him. Mary was evidently impressed as well, as Kaitlyn noticed the wedding ring on George's cock started glowing blue and vibrating more loudly.

Kaitlyn looked back at Katrina, and she had tears in her eyes. She had never seen Kaitlyn ride a ponyboy before, and she was clearly moved by it. Her ponyboy ran faster than George, but she was having difficulty guiding him effectively. Kaitlyn couldn't blame her. It was hard riding a ponyboy, and she was still learning.

Kaitlyn looked back at George, and he seemed tired. He was panting heavily. She decided to give him a short break, to allow him to catch his breath. After a few seconds, she released her grasp on his nipple reins, and she slowed him down. He came to a stop below her.

"Are you okay, George?" she asked.

He took a moment to rest.

"Yes, Mistress Kaitlyn," he replied. "I am fine."

"Great," she said, taking out her riding crop and giving him a few strokes to the thighs. "Get going again then. It's a race after all." she used the compressors on his balls gently for emphasis.

He resumed running, and this time he passed Katrina.

"Yeah!" someone yelled.

Kaitlyn glanced back, and Katrina was crying in frustration. Her ponyboy was struggling.

Kaitlyn hoped that this would be a good race for everyone. They were near the end of the first half of the first lap. The second half was almost free of obstacles. But George hadn't cum yet and he needed to cum before the end of the lap. Viola's mount had already cum twice. Her team was a ways behind them, but Kaitlyn expected that they would be a **** to reckon with later on in the race.

"Keep moving," Kaitlyn instructed George. "Don't stop."

Kaitlyn glanced back and saw that Katrina was looking at her. She realized that Katrina must be worried about losing.

"What's wrong, Mistress?" George asked her.

Katrina was crying and shaking. "I don't know if I can do this," she confessed.

"Yes you can," Kaitlyn assured her. "Just keep riding your ponyboy, and you will win the race."

Her ponyboy mumbled something to her, and it seemed to reassure her.

"Now let's get going again," Kaitlyn urged George.

They continued to run. Kaitlyn used the compressors ever so slightly to tease his balls while he ran, and he was beginning to respond.

Kaitlyn looked back and saw that Viola's ponyboy had come again. She admired his cock and imagined putting him leashed on the treadmill. A warm glow spread through her crotch.

"Why don't you take a break for just a minute," she suggested to George.

"Yes, Mistress Kaitlyn," he said.

She needed to bring him to climax soon.

"Let's see if we can pass those other ponies again," she added. They had both passed them while they rested.

They picked up the pace and passed the other ponies. Kaitlyn could feel George's balls tightening and his erection growing harder. She slapped Katrina's ponyboy on the cock with her riding crop as they passed them, and noticed him getting harder. He hadn't cum yet either.

"I think your pony needs you to be rougher with him," Kaitlyn advised Katrina.

She laughed nervously. "Um...okay."

Kaitlyn could feel that George's balls were starting to tingle, and she knew that he was close to an orgasm. She stopped the compressors and started using her feet aggressively on his cock.

"Take this," she commanded. "Cum for me now!"

George moaned and shook. Then he groaned and shot his load into the air, some of it splashing onto her legs.

"That was great, George," Kaitlyn complimented him. But he was slowing down now from the **** of the orgasm. She yanked on his nipple reins. Now that he had come, they needed to get going.

"Go faster," she told him.

He increased his speed.

Kaitlyn glanced back at Katrina, and she was watching them run. Her ponyboy was also looking back at them. Kaitlyn wondered if she was planning anything. She was. She pulled out a lassoo from a large pouch on her saddle.

"Stop!" Kaitlyn commanded.

George obeyed immediately.

Katrina whipped the rope at them. She managed to touch George's right arm, but missed Kaitlyn entirely.

"Oh no!" she cried.

Katrina whirled around to face me, holding the lasso in her hand.

"Well, this is interesting," she observed.

"What did you do that for?" Kaitlyn demanded.

Katrina didn't reply. Instead, she threw the lasso at Kaitlyn.

Kaitlyn dodged it easily, but Katrina didn't miss George. She wrapped the rope tightly around his cock and balls.

"Gotcha!" she exclaimed.

Kaitlyn grabbed the lasso and tried to jerk it off of him, but her ponyboy was too strong.

"Stop!" she commanded. "You can't do this!"

"Yes, I can!" Katrina insisted.

"No, you can't!" Kaitlyn pleaded with her. "This is against the rules!"

"No," she insisted. "Only **** is forbidden. This is fair play."

Kaitlyn looked back at George, who was struggling to pull himself loose from the rope. The lasso was hurting him. His cock was turning purple, and she was afraid that he wouldn't be able to cum anymore.

"I want to make sure you understand," Katrina said, pointing the lasso at me. "If you continue this game, I will be **** to remove that ring."

Kaitlyn's mouth dropped open. It seems as if Mary had heard that, because the ring activated again. This time, it exuded a clear gel that spread over his cock and balls. The slippery gel cause the rope to slip off him.

"Go," Kaitlyn shouted, pulling on his reins.

He started running, and Kaitlyn's team made good distance from Katrina and her pony. Viola's team had passed them while they were struggling.

They reached the finish line, completing the first lap. Kaitlyn let George slow down a little, but not stop, since they needed to keep well away from Katrina.

"Are you okay?" she asked George.

He nodded.

"Good," she told him. "Let's go again."

Kaitlyn pulled on the nipple reins, and they started running again. Viola's pony was ahead of them, but it wasn't by much. His tail swished behind him as he ran.

The second lap was much easier. They quickly overtook Viola's team, and Kaitlyn once again let George slow down just a bit, since she wanted to conserve energy for the third lap.

When they finished the second lap, Kaitlyn was pleased that they had improved their lead over Viola's team.

"Let's try to increase our lead even more," she said. "We need to win this race."

"Yes, Mistress Kaitlyn," George agreed.

And so they continued. Kaitlyn glanced back at Katrina, who was watching them run. She seemed to be having fun. She seemed to have taken Kaitlyn's advice, and she was using her boots roughly on her ponyboy's cock. He had finally climaxed once at the end of the first lap.

As Kaitlyn started the third lap, she could tell that George was reaching his limit. He was panting heavily and sweating profusely.

"How are you doing, George?" she asked him.

"I'm sorry," he gasped. "I don't think I can do this anymore."

"But we still have a long way to go," she reminded him. "We need to finish this race."

She pulled out a potion from one of the pouches in the saddle and poured it over his cock. The potion was designed both to increase arousal and to prevent a man from ejaculating.

"I think this will help," she promised him.

"Thank you, Mistress Kaitlyn," he replied.

She gave him another slap on the cock with her riding crop.

"Get moving," she told him, slapping him again. "We need to win before the other two teams catch up."

He picked up his pace, and they moved ahead. Kaitlyn glanced back and saw that Katrina was trying to lassoo Viola and pull her off her pony. She would have to work harder if she wanted to succeed.

The fourth lap was difficult for George. He was panting badly and had slowed down considerably. Still, they were making good progress.

"Keep going, George," Kaitlyn encouraged him. "We're almost there."

"Yes, Mistress Kaitlyn," he replied.

And then they passed the finish line. They had won! They had won the ponyboy racing contest. Kaitlyn was so excited that she pulled the reins so hard that they came off of his nipples, and he stumbled forward, gasping at the pain. But she didn't care. She had won! And George had given her an excellent performance.

"Great job, George," she congratulated him. "I'm very proud of you."

"Thank you, Mistress Kaitlyn," he replied. "This has been the best day ever."

"Me too," Kaitlyn agreed. "I'm so happy that I have you as my ponyboy."

"Thank you, Mistress Kaitlyn," he responded. "I love serving you."

"I know," she replied. "Now take off your harness so that I can give you a reward."

"Yes, Mistress Kaitlyn," George agreed.

She removed the armbinder and compressors, and then the leather saddle. He stood naked in front of Kaitlyn, wearing only his wedding ring on his cock. He was eager to please her, and he knew exactly what she liked.

"Turn around and bend over," she ordered.

George did as she asked. She knelt behind him and took his cock in her hand.

"Put your hands on the ground," Kaitlyn instructed.

He did.

She started stroking his cock, and she loved how he felt in her hand.

"Mistress," he whispered.

Kaitlyn was startled by the Queen's voice. "I promised to meet him after the race. I shall be the one to give him his reward."

Hurriedly, she took her hand off of his cock and prostrated herself on the ground. "Yes, your Majesty."

The Queen smiled. "Don't worry. You have earned an extra treat today. After all, you have won this race."

"Thank you, Mistress," George gasped.

Kaitlyn glanced back and saw that Viola had arrived. She walked over to her and kneeled beside her.

"Congratulations on winning," she remarked.

"Thank you," Kaitlyn replied.

"You're lucky to have such a good ponyboy," she added.

"Yes, I am," she agreed. "He's a gift from the Goddess."

"Well, I hope that you enjoy your prize," she said. She stood up and stepped aside.

A group of people approached George. There were seven of them: four other ponies, two exchange students, and three women.

"Here is a special treat just for you, George," the woman told him.

"Wow!" George exclaimed. "Who are these beautiful ladies?"

The woman laughed. "They are members of the Sisterhood."

George's eyes widened. "Really? Who are they?"

"They're from the city of New Femina," she explained. "These are your new friends."

"Friends?" George repeated. "I thought this was all for you, Mistress Kaitlyn."

"It is," she assured him. "But you've done well, and you deserve your reward. These women will take care of you tonight."

"Tonight?" he replied. "You mean we'll be staying here until tomorrow?"

"Yes, George," Kaitlyn told him. "They will help to look after you."

George just nodded. He understood that she needed to talk to the Queen about him.

The Queen addressed me. "Now that you have won this race, you may go to sleep."

"I would like to stay awake and watch you with George," Kaitlyn requested. "Is that allowed, your Majesty?"

The Queen shook her head. "This is only between George and I."

"Of course, your Majesty," Kaitlyn agreed.

George looked worried. "I don't want to be alone with her, Mistress Kaitlyn."

"You won't be," she assured him. "Not for long anyway."

"Thank you, Mistress Kaitlyn," he sighed.

There was no way Kaitlyn could know how long the Queen would need, but she didn't correct me. Instead, she looked at Kaitlyn and said, "I will see you tomorrow morning."

Kaitlyn nodded.

Then she turned to George. "We will begin after dinner."

With that, she left. The three women surrounded George, including the ones Kaitlyn had met earlier. They led him away from the others.

"So, now what?" Kaitlyn asked Viola.

"We wait," she replied. "And we wonder whether you've been a good girl today."