Chapter 32

Serendipity Park – Georgia
As told by Master Jessie

Mike was working on his laptop and humming an old song. “Build me up, Buttercup,” he bobbed his head to the music coming from his imagination.

“Do you want me to go check on the girls and get them ready for the anal-bead tug of war?” I asked. The schedule of events was pretty flexible. This would be the last fun event before the final races and the winner. It looked like it was going to be Pony Barbara, who won the overall competition this year.

“Yeah, take Buttercup with you,” Mike said he would join us later. He told me that I could touch her, but nothing else. Buttercup was also not to participate in ANY pony contests or events. “You can spank her if she fucks up. I want you to tighten her pussy spreader anytime she back talks. If she gives you ANY lip – you squeeze some of her lips! She gets three strikes, if she keeps on doing it after that then don’t squeeze her pussy off. Just bring her on back to the motorhome. We are done. I’ve made it clear to her that I am still not sure I want to train her. If she can’t behave herself after her slit has been screwed down hard three times then I doubt there is anything I can do to fix the brat,” Mike said.

He smiled though. I think he was genuinely concerned about her and he liked my cousin. It was hard thinking of her as “Buttercup” now. I don’t think I really believed she would continue with the training. I assumed she was doing this to get a rise out of Mike, or maybe her Mom.

I never really understand my Aunt or her, and the games they played with each other.

“Now that the ring is on tight, she’ll feel every time she walks. If the pussy stretcher isn’t a constant reminder of her place, then nothing will be,” he said. He told me no one else can touch her or give her orders.

“Should I put a collar on her?” I asked.

“No, she hasn’t earned one yet. If you need to lead her around, just grab her by those pointy nipples and twist. You can handcuff Buttercup if you like,” he tossed me some cuffs. I put them around her wrists and cuffed her hands behind her back.

Buttercup didn’t give me a hard time about it. She let me pull her out of the motorhome by her nipples and promised she would follow me.

I was so ready for her to start being a smartass. I was prepared for her to start testing me as soon as we left Mike’s presence, but she didn’t.

“So what wild hair got up your ass to make you decide to do this?” I asked her. I made her walk to the right and slightly in front of me so that I could watch her ass wiggle while she walked.

“My Mom and Aunt are changing for the better. They see it as a positive. The discipline addresses my particular shortcomings and might make me stronger and actually appreciate the things I take for granted. I asked my Mom if she thought it would help me, and she said she thought so, Sir” Buttercup’s answer was thorough and had zero snark.

I was instantly skeptical and started trying to work out what her real motivations probably were.

“Did you make some fucked up bet with your mother?” I asked. That was probably it. She probably bet Joy that she would serve in exchange for 100% of the money she earns over two years instead of just 50%.

“Yes Sir, I bet her that if I quit before she did that I would go back to Carolina and stay with Grandma. I’ll do what my grandma tells me, learn to be a proper lady and crochet, knit, and do whatever she tells me,” Buttercup replied.

I didn’t expect that bet exactly. I knew she and her mother took their bets pretty seriously though. Even if her mom wasn’t there – I knew she’d do exactly what she promised her mother if she did quit this training.

I asked her what her mother had to do if she quit.

“Mom has to go back to Grandma’s and do the same thing, because whatever my Grandma wants her to be, while I get to come and go as I please, Sir,” she explained.

“Yeah, I thought there was a hidden agenda,” I replied jokingly.

“I told Master Mike about the bet. It is just a commitment I made that I won’t quit before my mother does,” Buttercup explained that she definitely didn’t want to go back to Grandma and that was a consequence of quitting.

“Yeah, well, I’ll verify with him that you told him, and if you are lying, that is one extra tightened screw!” I threatened her. Buttercup assured me she had and said that would be fine.

“So, you would rather be spanked and poked like a slave than go live with Grandma?” I asked.

“Pretty much, Sir,” Buttercup said. She didn’t speak with the same formal style of speech like her mother did. She was still talking to me in her usual tone of voice, except now calling me Sir and not being quite as sarcastic. “I might actually learn to stop being a cunt this way. I don’t think I’ll ever be a proper little lady, but if I lose the bet, I’ll do my best to try,” she said.

I found it hard to believe that the cousin who has been kicking me in the back, pulling my underwear up to give me wedgies, and putting signs on my back calling me a loser since we were little was really willing to change that quickly.

“Mike is going to be really hard on you,” I warned her.

“Are you going to be hard on me, Sir?” she asked politely.

“I might put my hard-on ON you,” I joked with Buttercup. She usually couldn’t resist saying something snarky back to make me feel like a chump for joking with her. If she did, I would get to tighten the clamp on her pussy one time.

“Yes, you might, Sir” Buttercup looked down at the ground and bit her lip. I was impressed at her ability to control herself – but that was her first test. She asked me if I was trying to scare her into quitting.

“No, I just want you to be realistic about entering training. I don’t want you go into this thinking it will be easy or a joke,” I said. I felt like her older, wiser sibling for a change instead of the young kid she made fun of all the time.

“Well, thank you for worrying about me, Sir,” Buttercup seemed contrite and considerate. It was a refreshing change. I did want her to submit for obvious reasons but I had my doubts she’d last more than a few hours once it really started for her.

“That is going to be my job from now on once you start training. My responsibility will be looking out for you,” I assured her.

“I would like that, Sir” Buttercup sounded sincere. Sincerity wasn’t something that sounded natural when it came out of her. I felt apprehensive because I still thought she had some ulterior motive or plan up her sleeve.

It wasn’t dark yet, but it was close to dinner time. I could tell they were setting up for the contest near the main house because I could smell the yummy smoked pork in the barbecue. It smelled delicious. I’ve never eaten as well as I have at this campground. Even my Grandma can’t make ribs like Pit Master Jason.

We walked past some porta-potties they had at the camp. People were starting to walk up to the main event area. We weren’t in a private area or anything – so people could see that my cousin was wearing handcuffs. No one seemed shocked because it was a BDSM event.

Barbara was strutting her stuff near the main hall. I could see her even though she was more than 60 yards away. There was no missing those big fake tits and her bleach blonde hair. She had been squiring around Stefan all day long. She was showing him the ‘ropes’ of pony training. He wasn’t with her at that time, though.

“May I please use the bathroom, Sir? I didn’t get a chance to pee all day,” My cousin asked shyly.

“You are going to piss on the ground from now on,” I reminded her with a big grin. I couldn’t wait to see the look on her face the first time she did.

“Master Mike didn’t say I had to do that yet. I am not in training, Sir. Please?” Buttercup reminded me.

“Well, you can ask him when you see him. Until then, you can piss on the ground while we walk,” I said.

“I can’t even stop to squat, Sir?” Buttercup scrunched her nose.

I asked her how she thinks Ponies piss and shit all day. I had seen Pony Doris spray what seemed like a half-gallon of piss while at a full trot without missing a step. She just let it drop while she was walking.

“I guess you’ll be seeing me doing this soon enough,” she took a deep breath as if summoning her courage. Buttercup blushed, and she started pissing while she walked. She couldn’t help spraying her thighs with her warm stream of acrid piss.

“Yeah, well, you had no problem farting on my pillows before. I don’t see why you are making a big deal about pissing in front of me,” I joked.

“I have actually farted on your head while you were sleeping, Sir,” Buttercup admitted. She didn’t apologize, but she would soon enough. I knew she was struggling with behaving submissively. She was at least TRYING to be friendly, and I liked that a lot.

We saw a pregnant pony girl. I am not sure what her name is. She had huge rings in her pussy and nipples. She waved at me and smiled. I smiled back. I’ve found myself being hit on a lot by horny, more mature women at these events, and it’s made me feel really good about myself.

I don’t know why I was always down on myself before. Actually, I guess I do. I wouldn’t lay the blame only on my aunt and cousin. I think they have consistently ridiculed me for a variety of reasons all of my life. If you asked Amanda, she would say it was toughening me up.

The thing is there were other people who bullied and teased me too. My uncle Randy never considered me a man until we showed up right before we left North Carolina. He found out I was the boss of Chastity and Joy. Even my Grandmother has always treated me like an incapable toddler who doesn’t know his ass from a hole in the ground.

It felt so much more different now as people nodded at me in recognition and smiled.

Pony Doris pulled up next to us. She was nearly naked except for the two-wheeled wagon she pulls around. “Take me for a ride after the contest?” she asked. She licked her lips and blew me a kiss.

“Maybe. I am breaking in my cousin,” I said.

“Oh, I see how it is. You have a new toy to play with. Well, come see me before you guys pack up and leave tomorrow. I’d love to give you a little parting gift to remember me by,” she said. Her hands were cuffed to the wagon behind her, but I could tell she wanted to grab my dick. She jingled when she trotted off because she had little bells attached to her clit and nipples.

“Did you fuck Pony Doris, Sir?” Buttercup asked incredulously after she left.

“You know I can turn your screw for sassing me,” I warned her.

“Yes, Sir, I am just asking a question. It might be worth getting one twist of the screw to find out if you laid pipe in that old lady? She is Grandma’s age!” Buttercup reminded me.

Pony Doris was hot. I shuddered when I realized she looked a LOT like my grandmother. “Keep asking, and I’ll bend you over and spank you right here and then tighten your screw. You only have three strikes, and then you are done. Are you looking for ways to back out because you got cold feet?” I asked her.

“No, sir, sorry, sir,” Buttercup apologized to me. It was a rare moment.

“Someone call Ripley’s Believe it or Not. The great Buttercup has finally apologized to me after years of being a total dick to me,” I sighed.

“I’ve apologized before, haven’t I, sir?” Buttercup pouted. Her thighs were still wet, and her pussy was dripping because she had freshly pissed while trying to keep up with me. I wondered if she really understood how shitty she has been to me over the years.

“Whoa, a new snow bunny?” Daphne interrupted before I could decide whether I wanted to really get into how many times she made me feel like a fool. I’d have plenty of time for that later.

Daphne is blonde and has big titties. She is hot, but she only likes black guys. She has a massive ace of spades tattoo on her ass. Today, she had barbed wires wrapped around her tits, and a spiked ball hanging from her cunt lips. Even though she is supposed to be a slave she is a real bitch to me. She always look like she just smelled dog shit.

“Yeah, I guess,” I said. I try to avoid Daphne anytime I see her. I like her husband a lot more. He is really a nice guy. His slave name is Piglet. He is an accountant and pays all her bills. Piglet wears a cock cage 24/7 and is her cuckold. She never has sex with him. He loves her very much, and I think she cares for him. He seems happy that she serves Master Lamont.

“Lamont was checking this one out. She has a cute little ass. You want to try a little dark meat for dinner, honey?” she asked Buttercup.

“She is with me,” I said abruptly. Buttercup smiled when I spoke up for her and agreed.

“You keeping it in the family? You are her brother or something, aren’t you?” Daphne was chewing gum loudly and spoke with a New Jersey accent.

“Something like that,” I said as we walked away. I checked to see if my cousin flipped her the bird and was shocked she didn’t.

“You fuck your mother and that other broad, too, don’t ya?” Daphne challenged me as I walked away. I said nothing.

“Hey, you red headed motherfucker! I am talking to you! Do you suck on your momma’s titties or what? Look at me when I am talking to you!” Daphne called out angrily behind me. She needed the kind of taming that my Aunt was getting. Even if Daphne was dressed up like a submissive she certainly wasn’t one.

Buttercup caught up with me and started walking in front of me again so I could watch her butt while she walked. She’d need a lot of practice to learn to swing it like Chastity. “You claimed me back there. That was wild. I didn’t have to say anything, Sir” Buttercup seemed happy.

“You never had to say anything. You could just ignore people when they are rude,” I advised her.

Buttercup didn’t disagree. She seemed to process what I just told her.

I saw Courtney and Stefan heading back from the main event area. They looked disappointed. Stefan was wearing a pony outfit and trotting behind his sister.

“Where are you going? They are about to serve dinner and start a new contest,” I asked.

“Mom says we can’t watch,” Courtney spoke for the two of them usually. Courtney noticed Buttercup’s hands were cuffed behind her back and the pussy-clamp around her pussy lips. “What’s going on with all this?” she asked Buttercup.

“I asked my Mom’s master if he would put me in discipline. He is thinking about it. I have to prove I won’t be mouthy, Ma’am,” Buttercup said.

Courtney smiled. “That won’t be easy for you,” she said.

“No, it will not. If I fuck up three times, Master Mike says he won’t even consider my application for service. I’ll have to pick only two moments. It would be so worth it to crack a joke, Ma’am,” Buttercup smiled.

“Or you could try not being a smart ass at all,” I suggested.

“I have two left before it is all over, so I may as well just pick my moments, Sir,” Buttercup said impishly. She had a twinkle in her eye, but I knew she was not joking. She intended to use up her two burns even if it meant I crushed her pussy lips a little in the process.

“Does that thing hurt?” Courtney pointed at the pussy clamps biting into Buttercup’s twat. Her hood was sticking out like someone sticking their tongue out, and her pussy lips were bunched up.

“Oh yes, Ma’am,” Buttercup smiled.

“Do you like it?” Courtney asked.

“No, Ma’am.” Buttercup said quite bluntly. “I am going to wear it, though. After talking to my mom, I realized I was a super-cunt, just like her. I’ve been shitty to almost everyone I’ve ever known. You two actually helped me see what a brat I am,” Buttercup admitted.

“How is that?” Courtney asked.

“Well, you are so sweet and nice. You have never met a stranger. You are friendly to everyone. You seem like nothing ever bothers you, and you are above all the petty shit. I can’t be like that – I probably will never be like that. I need some restraint to keep my attitude in check,” Buttercup admitted.

I’d heard her mother say things like that all the time. It was apparent Buttercup really was listening when she pretended to yawn and not pay attention.

“If you only knew the real me, you wouldn’t say that,” Courtney smirked politely. The cute blonde looked like a little angel.

Buttercup told Stefan that he was also a big inspiration. “You wanted to be a pony, and you knew your parents were against it, but you had to do what was right for you, Pony Stefan,” she said. Technically, she didn’t have to call him Sir since they were peers.

“Wow, I didn’t really think about it like that,” Stefan said. He shrugged like it was not a big deal to him.

“Kneel,” Courtney pointed to the ground harshly. She knotted her eyebrows at her brother for daring to speak.

“Yes, Mistress,” Stefan said.

“Since we are all being honest,” Courtney frowned and pouted a little. “I may as well be straight with you. I have been dominating my little brother for three years. The other day when he told you he wanted to be a pony, I thought you would think I was a freak if I told you I was his mistress. I mean, he is my little brother after all. I don’t fuck him or anything, but I let him sniff my cunt when he has been a good boy. Don’t I Pony Stefan?” she rubbed his head.

He panted and whinnied while he looked up at his older sister with adoration.

“I didn’t want you guys to think we were perverts. That’s why I made him call me Caporal and pretended to be reluctant. My parents still don’t know that I’ve been training him. I have always wanted my very own pony,” she said. She looked so incredibly innocent, but now there was a devious edge to her that I had never noticed before.