Book 2 of the Million Dollar Chronicles


by Sir Thomas

- provided for use on SirJeff's Ponygirls by the author.
- do not use without the author's permission.

Chapter 8 - Reward and Punishment



Gerry was a great guy but he just didn’t understand. If a girl was going to be a submissive she had to be broken properly. Letting her get away with this type of thing was far more serious then he could imagine. This practice would give the girls an opening to make excuses if they didn’t like their situation. This couldn’t happen. It was a can of worms that simply could not be allowed to open.

I let Gerry have his little talk with the girls before I paged him and had him bring them to my office. The trainers had put them in fresh outfits with standard walking boots. The marching boots needed to air out after the hour of marching. The outfits smelled of sweat and needed to be washed and air dried anyway. Special gear in each room would allow hot air to be pumped through them. From what I remember putting on a warm suit felt really good. I almost missed those days.

The girls were brought in wearing full pony-girl regalia, sans bit and bridle. Their hands were free except for the elaborate gloves that we insisted they wear. The black boots were the standard walking boots with six inch heels. They seemed to be adapting well to them.

“Sit in the funny chairs,” I said, pointing to the chairs with the split seats. They arranged their tails to fall into the split. “Comfortable?”

Elaine and Katherine said nothing. They simply stood next to their charges. Their silver outfits with matching epaulettes tightly clung to their bodies. I was impressed with their poise and patience.

“I understand that you don’t want to do each other. Is that correct?” I asked.

Linda seemed to speak for both of them. She sheepishly replied to the affirmative.

“I understand,” I said. “You don’t want to hurt each other; right?”

They both nodded.

“Well, Linda, since you seem to be the most vocal, let me ask you a question. Do you think lifestyle means anything to us? In other words, do you really think I care if you’re gay or straight?”

“I don’t know.”

“When I gave my speech didn’t you hear me say that sex was used as a tool to subjugate you? Did you understand what I meant?”

“Not really.”

“Sex is a tool. Our pleasure is gained from putting you in situations that you hate. It’s a power thing. We take pride in putting our girls into situations where they can impress our onlookers and admirers.”

“Like teaching a dog tricks?” Jennifer asked.

“Exactly. Humans are more complex of course. That’s why we have to make strange rules to break them. Having the ability to reason makes the training process much more complex. It also requires far more intense and unusual tactics.”

“But why do you need us to sleep with each other?” Jennifer asked.

“You’re not going to sleep with each other. You’re just going to lick each other’s pussies. You’re going to get your friend off when commanded to do so. It will prove that your pony-girl training exceeds your moral values.”

“But I can’t have sex with Linda. I don’t want to hurt her!”

“What makes you think that having sex with her will hurt her? When someone orders you to stick your tongue between her legs, what exactly do you intend to do that will hurt her? How about you, Linda? Do you have some sort of plan to hurt Jennifer if I force you to have sex?”

“Of course not!”

“Jennifer, if Linda does as I tell her and sticks her tongue in you, do you think you’ll go insane?”


“Have a heart attack?”


“Dislocate your pussy?”


“Just checking,” I quipped. She almost laughed.

“Will anything really bad happen to you if you let her do this?”

“No. I just won’t like it.”

“But you’ve done things you didn’t like before, right?”

She nodded.

“Good. Do what we demand. Look, you’re both extremely intelligent girls. You’re not bimbos. You’re aware of your surroundings and you both have character. That’s part of the challenge, ours and yours. You’re both of high moral fiber. That makes the conversion to ponygirl that much more interesting and challenging. But nearly every girl we bring here is in the same boat. We look for that in our girls. We want girls of high moral fiber because they make the best reluctant submissives. All the girls have that trait so don’t think for a second you’re alone. The situation is not nearly as unique as you might think.”

Linda looked at Jennifer and stared into her eyes. Jennifer nodded. “We’ll do it,” Linda said.

“Good. Just don’t go back on your word. You might think I’m a sadist but I’m not. I absolutely hate dealing out punishment. Don’t give me an excuse to use this remote control on you. I will use it if I need to but I really don’t want to.”

“Yes, Tina,” they said in unison.


I wondered how bad it would be to do Linda. The idea of using my tongue between any woman’s legs was disgusting. Doing that sort of thing to my best friend was beyond imagination. Then again, I had to ask myself if it would be any worse than having some guy fill my mouth with semen. Well, it certainly couldn’t be worse.

The novelty of the latex was beginning to fade on me. Originally I had thought it fun to stretch the outfit over my body. Now I realized that no matter how much they powdered the inside, eventually it itched. Katherine had told me that they’d make me swap outfits after every exercise. I found that encouraging but still, it was latex!

We left Tina’s office together and ended up back in our rooms. It was time for another oral sex lesson. It was something I was not looking forward to. I was put in my armbinder and collar. Katherine called and a short time later another Hispanic man arrived.

This was my second encounter and I wasn’t any more ready for it than the first. If anything I dreaded the act even more because I now knew exactly what it would be like. I absolutely hated it!

“My name is Armando. You will submit, please,” he said in broken English.

I dropped to my knees as I had been taught and opened my mouth. Katherine had trained me well in this regard. I dreaded his company as he began to open his fly. And then I saw it. He was huge. The sight stunned me so much I forgot to get my tongue out.

“Extend,” Katherine ordered.

I was shaken from my trance and prepared myself for penetration. I stretched my tongue as far out as I could and watched in horror as his huge cock entered my mouth and proceeded to impale me. I thought he would begin pumping me with it but instead he pushed my head backwards and drove downward with it. When his cock entered my throat there was still three inches to go. He continued to push. I gagged. I was suffocating! But he continued to press on until his balls touched my lips. Then he stayed there!

“Breathe through your nose, Honey. You have to learn to do this. A lot of men use the deep throat technique. Hang in there. You won’t choke,” Katherine said.

I was helpless. Katherine was beside me, comforting me. I kept my eyes on Armando. I kept my tongue moving. I just couldn’t breathe!

He pulled back to let me have air but refused to pull out completely. He was slackening. He had released his load inside my throat! At least I didn’t have to taste it!

I did my duty until he withdrew. He complimented me, saying that I performed like a professional. I almost felt proud. I actually thanked him. It was a knee-jerk reaction I thought. I swear it was!


Another rape of my mouth and I was still sane. This guy wasn’t nice. He just said, “Open wide,” and then he did me. There was no sympathy, no calming words. There was only a demand that I do what he wanted. Elaine didn’t utter a single word. She just let him do his thing. I guess I had to get used to all types.

Once the idiot had left, Elaine dressed me in the marching boots, the bridle, and the bit. I was already wearing the armbinder and collar. I figured I was going to be marching again. Well, it wasn’t going to be quite the same.

At the foot of the bed was a large trunk that I had originally thought was a simple bench. She opened it and pulled out a saddle! She was going to ride me. I couldn’t believe it!

The saddle was comprised of two parts, a back plate and a seat. The plate was made of a shiny black fiberglass with leather panels attached to the sides. At the top there were thick leather straps obviously designed for my shoulders.

I stood passively by as she slipped the unit under my armbinder. She told me to hold it in place while she aligned the shoulder straps. After positioning the straps on my shoulders she abandoned them to work on the leather panels. These came together under my breasts to form a corset of sorts. Several small buckles were pulled tight to join the halves. Two buckles that were mounted on the panels awaited the shoulder straps. Elaine pulled both as tight as she could, at one point putting her full weight on them. I grunted as the straps bit into my shoulders.

When she was done my back arched severely. I looked like I was wearing a bustle. My ass stuck out provocatively and my tail stood high. I felt the corset support my abdomen and my back felt well supported too. It was well designed to allow me to carry the weight of a rider.

The saddle was next. It was made of patent leather and polished ebony. It sported three chrome supports on each side which allowed it to be mounted behind me at mid-shoulder level. The lower braces clipped to the part of the plate that covered my ass. The remaining supports were connected just under and over my shoulder blades. Once all was in place and secure I had a saddle mounted just above the small of my back.

“OK, Honey. We’re going for a little ride now. We’re going outside and it’s a little warm yet. You should be able to handle it though.”

I nodded my head.

“Honey, we’ve got to work on communication. When you are gagged or bitted, you must whinny! From this point on I’m going to use a level one jolt if you fail to communicate properly. Also, when you whinny, shake your head fully left and right for no or up and down for yes. Use the full movement allowed by your gear. Understand?”

I stared at her for a moment and was rewarded with a tiny jolt between my legs. Elaine told me they had a special button for a level one jolt since they used it so often. “Great!” I thought as I whinnied and nodded like an idiot.

Elaine took me outside using the reins to guide me. We stood under and awning for a moment to get accustomed to the sun and heat. It was probably in the mid-80’s, even with the sun obviously setting. Everything was tinted orange by the sunset. It was beautiful.

In front of us lay a long cobblestone avenue with an ornate median running down the center. A series of islands containing statues and water fountains decorated the path. Several hundred yards down the path I could barely see a single house. Even from here I noticed it was quite large. That was obviously our destination.

Without the heels the saddle would have been a little over four feet off the ground. But with the eight inch heels that height was now almost five feet. In order for Elaine to climb into the seat she’d have to lift her butt two feet. Well, that’s not exactly how it worked. I was told to crouch until my back was nearly horizontal. Elaine prevented me from going too low in order to give me sufficient leverage to lift her. When she was seated she leaned backwards which caused me to straighten. Then I simply straightened my knees and all was well.

I found her weight to be uncomfortable but manageable. The weight was centered on my jutting hips. I seemed to be able to stand almost normally with such an arrangement. Still, it wasn’t standing that I was concerned over. It was walking down the path in front of me that worried me.

After Elaine had retrieved the reins and settled her booted feet into the stirrups she told me to take it slow. She had me stand up straighter; telling me it would be easier on my back if I kept the weight on my hips. She was correct.

She began using the reins and her boots to guide me out into the sun and down the path. I found walking in the heels to be difficult. As if reading my mind she told me to stay on my toes and not use the heels any more than necessary. The toes were better designed to take the stride. “Half knee lift,” she ordered. Now I not only had to walk with a rider but also pay attention to form. I began lifting my knees but forgot the hesitation at the top of the lift. A light jolt and a warning by Elaine corrected that quickly. After that it was all teamwork. She would direct me with the reins and I would follow her orders.

She taught me much in the quarter mile trot down the boulevard. I learned not to anticipate her desires, instead waiting for the command to come. I could feel Elaine assisting me as she shifted her weight to allow me to trot faster, when the order came of course. Finally she had me perform the most difficult walk, the high knee step. The funny thing was that with her sitting on my back I found it easier to perform than when I wasn’t mounted by a rider. Strange!

We circled one or two islands before heading to the hacienda at the end of the street. As we approached I noticed the beautiful adobe walls and the clay tile roof which seemed to glow in the setting sun. The façade featured a porch protected from the sun by an arched wall, the center of which allowed entry into the building. In front of the wall large clay pots decorated a walkway as well as small cactus and statues.

I was made to march through the center archway. From the shadows, Gerry appeared, smiling. As Elaine dismounted Gerry examined me carefully. “How did she do?” he asked.

“Quite well. She had hardly any breaks in form. I’d almost say she enjoys the saddle,” she said. That made me frown behind my bit. I wasn’t necessarily in agreement.

“Great. Take her inside and water her. Dinner is at seven sharp. I’ll expect her to be ready.”


She was awesome! The red outfit had the slightest orange tint from the setting sun. The reflection off the latex was unbelievably captivating and the contrast from the black leather accoutrements was exquisite. When she arrived Elaine had her high step onto our porch where they stopped and posed. Linda crouched to allow Elaine to dismount then stood at attention. She was a sight to behold.

After dismissing them I made my way to the kitchen. Several cooks were preparing an exquisite meal. The smell of Thai aromas permeated the air. Peppers, curry, and fruits were waiting for the meats of choice. There were appetizers such as Kanom Jeep, Chicken Satay with peanut sauce, and Tom Yum Goong. Most were nearly ready to cook. The soup was simmering. The sauces were kept warm. Dinner would be exceptional!

Linda’s saddle, bit, bridle and collar had been removed. Her boots were replaced with walkers. The only thing that remained was the actual red outfit which had been buffed with a towel to clean off the small amount of dust which had blown on it during the trot over here. Elaine had freshened up her makeup and combed her hair, pulling it into a ponytail that extended down to her shoulder blades.

Elaine looked exquisite as well. Her silver uniform had been cleaned and her makeup was exceptional. It was suddenly obvious that the five grand paid for her cosmetology training was worth it.

“You both look lovely,” I said as I took their hands.

The women smiled and thanked me.

“Dinner is waiting. Please, come this way.”

As we sat the stewards went into their routine. First drinks were served. Only the finest wines were kept in my cellar. I had trained Elaine in the finer arts of the grape. I was surprised at Linda’s exceptional knowledge of winery. She immediately recognized each selection that was placed before her. She commented me on my tastes in wine.

“May I?” she asked reaching for the bottle.

“Chateau Lafleur Palmerol. There aren’t but a few dozen cases left in the world if I remember what my ex told me. 1950? My God! What is this worth?”

“You tell me?”

“It’s got to be at least $10,000 a bottle.”

“It’s eighty years old. Try $10,000 a glass.”

She looked at me with a look that simply defied description. “You can’t be serious. I can’t drink wine this expensive.”

“Are you allergic? Go ahead. Just sip it. Savor the aroma, the body. It’s amazing.”


First he treats me like an animal; then he treats me like a queen. I don’t know what to make of him. At times Gerry seemed so sweet and at other times he was something that made me think him a monster. But something captivated me about him from the moment I first met him. He had a hidden quality. He always seemed to care, even when he was demanding perfection. And he was unbelievably handsome!

I was beginning to enjoy the outfit’s look. Every time I looked in the mirror I admired the shine of the suit. The black boots and gloves just seemed to go with the outfit. It didn’t look kinky to me. The outfit simply looked gorgeous!

I enjoyed the heels too. I hardly ever wore big shoes but the boots made me feel important because I was so much taller now. The heels seemed to force me to walk with poise and grace. On top of that I was nearly at eye level with Gerry, who I knew was nearly six-ten. God! I hoped he was as hooked on me as I was on him!

I was grateful to get out of the saddle gear. In order to support a rider’s weight the straps were buckled pretty tight. That was a bit uncomfortable at first. But when Elaine climbed into the saddle I discovered that I didn’t have to bear the weight completely on my shoulders. I carried her using all parts of my body, it seemed.

We all gathered in the dining room. Gerry, ever the gracious host, seated us with the manners of a true gentleman. Elaine and I both smiled and giggled. We simply weren’t used to such treatment.

“Did you enjoy your walk?” he asked me, acting as if this activity was as common as driving a car.

“Enjoy?” I asked.

“Yes, did you enjoy it?”

“I didn’t find anything enjoyable in being ridden like a horse. Then again, I didn’t find it particularly annoying either. I guess I was OK with it,” I replied.

“Well, that’s better than some girls take it I suppose. Did you find the weight excessive?”

“No. I was fine.”


“That smell; I know it from somewhere. A couple years ago a friend took me to a Thai restaurant in Houston. What are we having?”

“The chef has a special Thai curry dish. He also has a number of side dishes and appetizers for us to try. He’ll be out in a moment to put on his little show. I think you’ll like it.”

“I wasn’t expecting to be treated so well,” I noted.

“You’re being rewarded,” he replied.

“For what?”

“You had the best score in our afternoon march. Your accuracy during the trot was better than anyone else. So, instead of the common fare of the cafeteria, you get a special treat. You get to be Cinderella tonight. And I’m the prince!”

“You should be glad that you didn’t have one of the two lowest scores,” Elaine mumbled.

I looked at her with concern. “What would have happened?” I asked.

“The two girls with the lowest score have to dust all the rooms,” I replied.

“Well, that doesn’t sound too bad.”

“They use a duster that’s attached to a penis gag. With the short hobble, it takes many hours for them to complete the task.”



I hated this! Tina came in and declared that I was low girl. I just stared at her, confused. “You were the least coordinated of all the girls so you’re going to be put through some unpleasantness,” she said.

“What kind of unpleasantness?” I asked fearfully.

“I wouldn’t want to spoil the surprise,” she said as she turned her back and started to leave. “Oh, Kate, you’ll have to monitor both girls. Pat is working on something special for me.”

“No problem,” Katherine said.

Kat left for a while after removing my suit. I hated having to remove the tiny screws on the breast plates each time I wanted to remove the outfit. It was annoying and, in my opinion, nonsense. But I didn’t make those decisions so I endured. “Take a shower and use the bathroom. You won’t get the opportunity for some time.” she told me as she left.

It took a half hour before Kat returned with a short girl in a red outfit just like mine. The thing was that I couldn’t see her face because it was hooded. And in her mouth she held a feather duster. “Now that’s weird,” I said.

“You’re next,” she said suddenly. “Put your outfit back on.”

After Kate checked my outfit and made sure it was sitting properly on my body, she slipped into the big closet and returned with an armful of leather. The first thing to go on was the armbinder. I just let her work but I hated that damn thing. Next she put the corset on me. I guess she didn’t want me to wear the boots until she had finished pulling on the stays. She put a knee into my back as she pulled the black leather tube tight around my belly. She was pretty tall and obviously pretty strong. I’m sure she had done this many times before. My waist had shrunk by at least three inches and I could hardly breathe. On top of that my breasts were cradled in little cups. Well this was punishment I suppose.

I was disappointed to see the marching boots being put on my legs. I was hoping for something a little lower. But I guess that extreme measures were in store and this was as extreme as they could come up with. The nine inch heels and the huge hollow platforms were bothersome. Kat didn’t appreciate them either because she couldn’t reach my head once I stood. I had to kneel for her to finish my preparation.

The only thing left to tend to was my head. Kate took the hood and simply slipped it over my head. My hair was threaded through the top hole and the back was laced tight. A wide plastic collar was placed on my neck and bolted in place with four thumb screws. Finally the head harness was placed on me. The dildo that went into my mouth was about an inch and a half wide and three inches long. That was the worst part of the deal.

Katherine explained the situation as we dusted my room. “I thought you did better. If I would have known your score had been so low I would have told you what was in store,” she said as we continued to move our feather wands across the shelves, books, and tabletops. “I guess I should introduce you to each other. Jennifer, this is Kara. Kara, this is Jennifer.” We stopped for a moment and nodded. Then we went back to work.

The dust was exceptionally thick, especially behind the computer monitor and between the books. Katherine explained, “Just to let you know there’s a special rule. If your marching score is 200 points or better you’re exempt from punishment. If you keep your score down you won’t have to worry about being punished, even if you’re last. Usually all our girls come in with good scores by the sixth week. That’s why your room is so dusty. It hasn’t been touched in two months because nobody had a bad score for so long.”

We both absorbed this while we continued to hobble around on our heels and dust the room. At some point Kat told us that we had done enough. We moved to the next room. The room was empty. We began dusting as before. “All the girls are out marching,” Kate said. I’ll take you out tomorrow night. You’re going to be busy for the next two hours.”

It took till ten that evening before we had finished dusting. We hobbled and dusted. We sweated and labored. We were shocked when we slowed our pace. We were like robots, totally at the command of our slave driver, Kat.

Just as we were finishing our twelfth room the girls began returning to their rooms. Each was in their standard marching outfit of skyscraper heels, latex outfit, bit, bridle, etc. Some wore strange saddles and others wore harnesses that were obviously designed to be hitched to carts. I didn’t see Linda. I assumed I missed her. Linda’s room was last and when we got there she was nowhere to be found. I wondered where she was.

I’m sure Kara thought, as I did, that we were finished with the cleaning detail when we reached the last room. Of course we weren’t. There were offices to clean. While girls walked through the halls, now devoid of the majority of their bondage we were taken to the offices. There were eight offices in all and it took another two hours to complete the task. Tina was still working and noted our predicament.

“You’re lucky. Some of our customers treat poor performers much worse. Some turn them into four legged ponies. Some even make their girls clean the floor with their tongue. We aren’t so abusive. If you want to avoid this, get your scores down. Who knows? Next week one of you may be chosen to be Gerry’s playmate. Now that’s an honor!”


The dinner was excellent. I had never eaten Thai cuisine before and I enjoyed every morsel. The first course was a light broth soup with button mushrooms and shrimp. It was very spicy but quite delicious. Gerry called it tam yum goon. I think that’s how he pronounced it. Then the chef brought out these little chicken pieces on bamboo skewers. That’s called chicken satay. The funny thing was that the sauce was made from peanut butter. It was weird but really good! They also had these little crab puffs which the chef called kanom jeep. I ate a half dozen of them by myself. Finally they served a seafood curry which was made from coconut milk, pineapple, Asian veggies, and at least five different types of seafood. Gerry told me it was the chef’s specialty. It was called Shue Shee Curry. I was in heaven.

“So what do you think?” Gerry asked.

“The food is superb,” I said as I sipped the Cabernet.

“I was referring to the bondage. You’ve endured one day and there’s a lot more of this to come. Do you think you can handle it?”

“If I’m treated like this I can,” she replied lightheartedly.

“Well, don’t get used to it. Things could turn around suddenly if you lose your focus and don’t march well.”

“I know. Question?”


“When I was browsing the web I saw a lot of sites that showed pony girls in stables. Will I have to deal with those sorts of living conditions?”

“That’s a good question,” Gerry replied. “When you go to the finishing facility you’ll be put in special stables. There will be common bathroom facilities such as toilets and showers. There will be beds rather than the straw mats that some have had their girls placed in. But you will not have carpeted floors or large private rooms. You’ll live in a stall like an animal.”

“What about when I’m done with training?” I asked.

“Your treatment would depend on where you go. I can tell you that my facilities are similar to those at the finishing camp.”

“Thanks,” I said. At least now I knew what kind of treatment I was in for.

“Is there anyone you’d like to contact? I have full internet here. You can IM someone if you’d like.”

“I don’t think so,” I said.

“Are you sure?”

“Well, there was a friend at my old business that I was pretty close to. She runs IT.”

“What’s her name?” Gerry asked.

“Now wait a minute!” I said. “You’re not looking for another girl?”

“Linda, I’m always looking for another girl.”


“Is she pony material?”

I thought for a moment. It was as if I was compelled to answer truthfully. “Yes, but that’s not the point. I can’t condemn her to this life! She’s my friend.”

“Do you consider being made a millionaire condemnation? Aren’t you forgetting the golden rule?”

“Do unto others?”

“No, Greed is Good!”

“Oh!” I said realizing that I was looking at the problem from my own narrow mind. This wasn’t my decision to make. It was hers.

“Her name is Megan,” I almost whispered in defeat.