Jim's Girls Ch. 09: Ponies Compete

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The ponies compete, a boy loses his virginity, and Jim wins.
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Part 9 of the 10 part series

Updated 12/24/2023
Created 12/14/2023
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DirtBoss
DirtBoss
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Anne came over and handed Jim a pair of large binoculars.

"Your girls will enter next. They will be in the pairs, your original pair and then the pair you are purchasing. They will be pulling carts with wranglers on them dressed up as carting ladies. You will see. The teams will come out and do the basic carting course where they will maneuver through the course and back the cart to a wall, the grand finale is when they leave that wall, they will get the cart up to a run and then stop it completely before leaving the arena." Anne explained.

"The wranglers use the whip for direction and correction so you will see the whip touching shoulders, breasts, and making marks on asses as correction. Managing the whip is an artform to itself. I have two of the best with your girls." Anne explained the program.

Jim pulled the binoculars up and focused on the opening in the arena Anne had designated. He saw two small women with large breasts for their size enter the arena. They each had a pink plume woven into their hair coming out of the top of a leather hood.

The hood came down and had eye openings that were covered with padded blinders. A halter went over the top of the hood and came down to a one-inch-thick rubber bit with a hole in the center. Opening the hole was a 2" ring gag.

From the base of the bit a chain went under their chin. Each girl was in an armbinder that put her hands in a reverse prayer and attached the fingers to a very severe training collar holding their heads forward.

The reins the woman on the cart was using had four leather reins two went directly from the rings on the end of the bit back to her hands. The other two were fed through hard rings on the training collar's sides and over the shoulder to large one inch by 1/4" nipple rings.

Two small chains came down from the nipple rings to the same one-inch ring at the belly button, down through to a one-inch ring in the clitoris. He would later see that the hood was kept back by this ring as well.

The ring at the belly button level was built into a bone corset that tightened their waists to keep the figure desired. The two wore knee high boots with hooves for feet and no heels. The first two ponies' leather was all pink and black. The second two wore white and red. They had platinum hair and raven black hair with red plumes woven in. He kept his eyes on the first two.

He wondered how they could be blindfolded and still accomplish this task. Seeing their breasts bounce and heave in anticipation. Was very exciting. Kitty and Nibs had changed dramatically.

Their asses were slightly smaller and there was now no fat layer over the muscle. Both had breasts other women would envy. He noticed somehow the surgeon kept the cone areola and long nipple and they still looked right.

The woman riding in the front cart was dressed in a hunting outfit of greys and browns with a derby on her head. Her jodhpurs tucked into her knee-high boots up in the driving stirrups of the cart.

The second was dressed similarly in tans and browns. The front carter flicked the reins and the girls' high stepping in unison began the course. Jim noticed that the bit reins and the nipple reins were not used in unison. The whip would flick a breast when the nipple reins were moved. They did not move much but Jim assumed they could be if the pony girls did not respond to the input.

The two got out of step at one point and a quick movement of the whip and he saw an angry line on Kitty's left ass cheek and the two were back in unison. The part that amazed him was watching the cart back and stay straight.

The woman on the cart said nothing the entire time. It was all done with the reins and the whip. The carter flicked the reins hard and the two women started forward as hard as they could. Jim could see the muscles in their legs and lower abdomen go tight. Wow they really did not have an ounce of fat on them.

Even the thirty-six-year-old mother had that body builder V in the muscles around her pubis. The two got way out of time trying to get the cart to speed and the carter stripped both of their asses multiple times. Jim caught himself jumping up out of the chair and yelling for his girls.

The second pair were backing as the first finished and Jim anticipated their explosion out of the wall. These two stayed in perfect time getting up to and maintaining a run. They stayed together slowing the cart and had a beautiful sweaty sheen on them as they left the arena.

Anne came over and Jim handed her back the binoculars. "Very nice for their first futurity. I believe that "Night and Day" will be in the top three where Nib and Kitty should top ten. They need to work on timing. They finally have the trust in their carter, that was hard for them to do." Anne stated.

"Can I go down and visit them?" Jim asked.

"They are right now getting in their livery for wedding coach competition. That will have all four girls completing the course together. The carter in the second group will be guiding that coach as she has more experience managing the eight rein teams." Anne replied.

"As soon as that coach is out, we will wait for a half hour for unharnessing and washing. Then you can go visit the four. I will take care of the three as you do that. I see Q has donated a young male for you to train." Anne stated.

"You know well my propensity to gamble. I won this time, but my girl broke one of my rules doing it so Q is doing me the favor of punishing her for it." Jim offered.

"She broke a rule of yours to enable her to win for you and you are having her punished for it? That doesn't quite seem fair, does it?" Anne inquired.

"Fair is where a pig wins a ribbon. She did not request of Mistress Q relief from the rule that she is not allowed to force a male to orgasm if he does not have permission. She has as much responsibility for his orgasm as he does, so it is her punishment to take." Jim explained.

"You are right, I was not thinking about it that way. Q can be quite cruel you know." Anne informed.

"I hope so, Sub Slut needs a couple of orgasms from having her tits and cunt whipped." Jim said. He sat and lifted his rye to Anne and said, "Thank you for the show." Anne moved on about her duties as hostess.

Jim whispered in Cece's ear. "Slowly without touching him anywhere else. Softly massage P.P.'s balls. If he moves squeeze hard until I say release."

Cece mouthed, "Yes, Sir." Without sounding back to Jim. Cece shifted and with her right hand started up between the boy's parted legs. She braced herself with her left palm on the ground and had to shift her knees.

Using the tips of her index, middle and ring fingers she touched the back side of his scrotum feeling the soft fur of young pubic hair on his scrotum. Using her thumb, she began to rub the two nuggets against her dancing fingers.

The boy began to moan. Jim could see his cock strain against its prison. P.P. got his knees further apart and moved his hands from the back of his head and Cece began to cruelly squeeze the testicles just seconds before she had been caressing. He tried to close his knees when Jim's feet suddenly appeared on either side of Cece and forced the knees back apart.

"Get your hands back in position. No one released you. I don't care how much pleasure is given or how painful it becomes. You will not break position without permission." Jim demanded.

Once the hands were back Jim said, "Stop squeezing and go back to caressing."

Cece complied with the order. Now the boy was moaning and sweating instead of squealing like a little girl.

"Now hold position and enjoy her fingers if I allow her to caress your pathetic little sack. Don't you dare orgasm on my slave's hand and wrist." Jim told his newest charge.

Cece continued to caress the little nuggets. She felt them begin to try to pull from her fingers tightening against the restraining ring between them and the perinium.

"He is about to cum Sir." Cece said. Jim could see the string of precum flowing from the tip of the cage.

"Stop, collect up his mess and feed it to him." Jim told her.

Cece quickly complied and the boy continued to moan for a minute. Q had walked up just at the beginning of that.

"What I like to see. A young man receiving direction from a strong man, to make sure he is trained properly for a woman's use. I see Petites Cochins being properly trained right from the beginning." Mistress Q stated.

Jim turned at her word and said, "We will be calling him P.P., short for Piggy Pete. I see you marked up Sub Slut nicely."

"Does she always make such a mess when she is whipped? I could not get her to stop orgasming as I punished her for orgasming without permission. So, I figured the best punishment was to concentrate on her ass which seemed to draw less orgasms."

"Inspection Sub Slut." Jim said in response. Sub Slut stood, put her feet a foot past shoulder width on each side. Her legs shook horribly. Put her head back, mouth open bent at the waist to 45 degrees and held her arms 90 degrees from her shoulders. Jim walked over and a server was walking by. "Bring me some aloe lotion for my slave please."

"Yes, Sir." Said the server scurrying to accomplish this task.

Jim did not touch Sub Slut's ample ass. It was crisscrossed with welts bruises and oozing cuts He bent down to inspect the back side of her bared pussy, it was flaming red and a couple of cuts on the Labia Majora seeped blood.

There was bruising already showing inside and outside the Labia. Around her clit cover was purple with bruise. He stepped in front of her. Her mons was crisscrossed with welts bruises and cuts. It continued up her entire front side and over the breasts to the collarbone. Both had bruises on the points. He lifted each breast with the thick nipple ring and inspected the underside. It was hamburger as well.

"How many orgasms did Mistress give you Sub Slut?" Jim asked.

"I don't know Sir, I lost count near twenty Sir." She said quaking.

"Did you thank her at the time for your orgasms?" Jim asked.

"No Sir, I was consumed by subspace and could not speak Sir." Moaning as Jim touched her bruised and battered clit cover.

"How do you think you could repay mistress for so much pleasure. I am sure her arm is tired from lifting the whip so many times on your behalf. You did not thank her properly, what could you do to make amends? What could such a worthless fuck hole system as yourself give to someone like Mistress Q?" Jim required.

"The only thing I can give is me and I really can't give that, only you can Sir. I can give her whatever you will allow this worthless fuck hole to give." Now crying slightly in frustration at not knowing the answer.

"I will have you give Mistress Q, this boy, fully trained to serve women in a week. You will not damage him; He will be trained in how to give women pleasure with both action and conversation. As your holes will not be worth using in that short of time you may ask for some of the other holes I own. I will decide who gets the three cherries the boy must give and in what manner they will be given. "Converse." Do you understand your task?" Jim asked.

She dropped from inspection to conversation pose smoothly showing lots of practice. The pain from her ass sitting on her heels was extreme and causing her pussy to make a mess on the floor below it.

"I believe I do Sir. May I ask for direction at the times that I am confused at what is asked of me for the boy?" She begged.

"Yes, and I will give you the direction I wish my first lover had for me when learning the art of women's pleasure. As your body is not the best to be seen by a young mind first. Tonight, he will spend time with me and Cece. I will task your care to Fetch. You will assume training on the second day. Now ask Mistress Q if you can lick and suck the sweat, she obviously created in her crotch giving 20+ orgasms with her whip."

"Mistress Q, may this worthless slave lick and suck the sweat created by giving her 20+ orgasms from your nectar region as a gift from my master?" Sub Slut requested.

Q stepped forward and pulled her dress back and enveloped the kneeling slave. She turned and bent at the waist.

"Use your hands slave, get that asshole open, lick and suck the contents out." She pointed to the older man that had been following her.

"Get down there and help her. It was your son that created this mess."

The man dropped to hands and knees crawled under the dress and his head could be seen moving at the front of her crotch while Sub Slut's moved the back. Quickly Mistress Q grabbed the man's head and held it stationary as her hips bucked and she enjoyed an afternoon orgasm.

Q touched the head in the back and spoke. "You can stop now. Thank you."

Sub Slut waited where she was, and the dress flowed over and off her as Mistress Q departed.

Jim walked to her and spoke. "Thank you for atoning for your mistake. You will do a great job with this boy. If you don't feel like he is ready in seven days, I will negotiate more time. I want him perfect when he returns to his mistress."

"Thank you, Sir." Sub Slut said with tears streaming down her face in relief.

He looked at Cece. "Take the boy and Sub Slut down to the van. Lay out soft blankets for her, I will send lots of water, she is going to be dehydrated. Use the boy to rub the aloe into his new teacher's body. Do not allow him to remove his blind fold but have him caress it into her marks. Jim instructed.

He will get to feel tits, an ass, and pussy before he sees them tonight. If he gets close to coming stop until he can continue without orgasm. A bucket of ice will arrive if you need it. Now go." Jim unclipped Cece's leash and handed it to her. She picked up Sub Sluts.

"Do you want to crawl or walk?" She asked the thrashed slave.

"I want to walk." Said Sub Slut. Using a chair and Cece's hand Sub Slut made it to the toes of her ballet boots and timidly led the way. Cece grabbed the boy's shoulder and said, "Follow my direction and you will be fine. Jim saw a fine string of precum from the boy's cage. He remembered being a teenager and a virgin. The smell of your first woman that has orgasmed never goes away. Sub Slut stunk of it. His girls were up again soon.

A rye was delivered, and Jim told the server, "I need to speak with Mistress Anne when she comes available."

She departed into the crowd. Nikko sat in the chair next to him. "I see you can inflict pain, when necessary, but always followed by compassion. That is hard to get to. I know after lunch you said you had something to offer, I may want to trade for. Can we discuss it here?"

"We can, I just don't want to offend you in anyway by not knowing the way." Jim stated.

"I negotiate with you blunt Gaijin all the time. You at least understand you don't know how to act and try not to offend. You have done well so far Jim san." Nikko answered.

"So would I be disrespectful if I called you, Nikko san as well?" Jim asked.

"That would be respectful, Jim san." Nikko replied.

"I have a woman that earned great debts to her husband, his friend, and her employees. She was evil to them for years, against their wills. I have mostly righted her wrongs. The man and his friend are now married to slaves of mine and have heirs to be born in 7 months." Jim explained.

"I have been using the woman as a decoration for two months. She has not seen the light of day since she offered herself to me at one of Anne's parties. I had her bound and eyes covered for the first week. Anne sent me to a surgeon, and I did not want her eyes removed. I wanted to give her the hope for vision again, but the surgeon sewed her eyes shut for me. Seeing how you have taken care of and trained well the woman in your care, I wondered what it would take for you to do a like thing for me with this woman?" Jim asked.

"I was raped as a young girl and became pregnant with a bastard. My father took care of the rapist in front of me and as I was his oldest child, he did not want me or my first child to be killed. He wants nothing to do with her. She is to be 18 in a month. I will take this woman off your hands if you take an 18-year-old and make her a productive member of society." Nikko asked.

"I don't necessarily want her to be a slave. I want her to become an educated professional that can contribute to my company when my father passes. She should also know how to please others and have some empathy for other situations. You seem to be a good man to teach that." Nikko explained.

Jim held up his glass of rye, Nikko a glass of Japanese whiskey. They formalized it with a click of glass, the western way.

"I will have her delivered tomorrow" Jim stated, "I just need an address."

"I will give you the address of a local shipper that I use. He will receive her and ship her safely to my estate. I will deliver my daughter to you. I will need a name you want her to use for the US papers she will need. I prefer a western name." Nikko said.

"I will research it a little bit and text you a name. You will have to do the rest; I am unsure how to do that." Jim said standing. Bowed to Nikko san as she departed with Anne arriving.

Handing Jim back the binoculars, "The wedding coach is next, and your ponies are the first out."

Jim trained the binoculars on the entrance. Night and Day were in the first two traces with Kitty and Nibs right behind them. The harnesses were all red as the Cinderella looking coach was gleaming white and gold.

Seeing the four in perfect step with the same sized frames and much closer in breast size with the enhancements made Jim happy. The woman directing the four worked magic with her hands and fingers giving just the right input with only the reins. There was one point in backing the larger coach between poles on the ground that the carter used the whip to give Kitty a stripe on her left cheek as she stumbled and lost time.

The girls got up to a fast run in the length of the arena and slowed to a walk to exit the narrow runway. Anne returned to Jim.

"That will be one of the better runs of the day. Your girls have acquitted themselves very well. I will put their winning to the $100K you will owe for Night and Day." Anne proposed.

"That is acceptable and thank you for inviting me." Jim told her.

Jim went to visit his ponies when Anne allowed it. They were in a stall as pairs. He guessed because they were pairs, they did not spend time apart. Jim was allowed to enter the stall with Nib and Kitty. He thought they might need new names after this, but he would think on it. They both came directly to him and began to nuzzle his arms and chest.

Both were 5' tall but with their hoof boots it added four inches to their height. He cooed in their ears and kissed their cheeks. He slowly explored the changes made to their bodies. Both had erect firm 32D breasts on their small frames.

The cone areola and long pink nipples had not changed but the rings through them were much larger. He moved the rings around and both girls moaned and pranced slightly. The same when he moved his hand down their very flat stomachs to the one in their clits.

The hole for the vertical piercing had closed. Both women continued with his nose ring and his stones were still in place. He slowly ran a finger between the heavy rings that now held the Labia Minora and Majora together. Both moved and started to move away from his hand.

He stopped and let them get comfortable again. He said, I will be here in eleven months to get you. You will see me often as I will not miss a show you attend. You still belong to me and are more beautiful than ever.

He went into the other stall and was received the same way. He got to think that JP was going to have to buy a ranch because these girls were not going back once they had spent a year doing this. Jim returned to the van and Fetch was loaded in her cage. P.P., Cece, and Sub Slut were in the back on blankets, and he began the bouncy road out of the ranch.

DirtBoss
DirtBoss
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