Chapter 33

Serendipity Park – Georgia
As told by Master Jessie

Mike joined us for Dinner shortly after the maiden compulsories were finished. Maiden compulsories are pony-girl exclusive events that all the pony girls in competition MUST compete in to win the competition. I think Uncle Evil thinks up the most humiliating compulsories just to fuck with Pony Barbara, but that is just me.

They are basically naughty games and contests, and I have loved every minute of my time at Serendipity Park. I am hoping to visit here again one day.

The part that I enjoyed the most was the evaluations. The girls were measured from head to foot, and then they were whipped as they marched in time to Uncle Evil’s drill cadence. The girls that couldn’t get the rhythm had the sorest butts.

The girls with the most points so far in the event were put into a top tier category. Heavy metal rods were inserted into their assholes. The girls had to hold them up with nothing but their sphincter muscles for as long as they could. They were graded on that.

Naturally, Pony Barbara won the contest. Uncle Evil called her a royal Tight Ass, and we all had a laugh at that. My Aunt scored pretty well in that category as well. I was shocked she could stand up and hold a two foot metal rod out of her asshole without dropping it. The training we’ve been doing has really paid off.

They did a similar but not quite as excruciating evaluation for the other pony girls and the pony boys.

Mike brought his tablet with him because he was working out new rules for my Cousin. He was shocked to discover none of her screws had been tightened and quizzed me on her behavior. I told him I only had to spank her once.

“How did that make you feel, Buttercup?” he asked.

“Powerless, silly, and I guess I felt like I deserved it, Sir.”

“You need to stop guessing. This a commitment. You are either doing this, or you are not. Your ass will develop two sets of callous before you finally learn anything worth teaching somebody else, but it is a lesson worth learning,” he assured her. He held up his tablet and told her that he had been working out her new rules. “You have until morning to change my mind about training you. If you really want this you are going to beg me to re-educate you just like your mother and Aunt have done,” he said.

Buttercup did not like begging. I could tell from the scowl on her face she’d rather have this training inflicted on her. She could whine and complain about it but ultimately do what was expected of her. The prospect of having to beg to be treated like a little slut wasn’t appealing to her.

I had prepared Chastity and Joy for the final events of the weekend. There were three more races and a freestyle competition for dressage. Pony-girl carts would be the first one. The girls would have to pull heavy carts in two teams of six girls each. It was extraordinarily grueling and challenging because even though it is a race, they have to do it with their ankles hobbled together. It would require extreme teamwork for the ladies to pull and even complete the course, all shuffling in unison.

The girls would be in full pony girl regalia, including full horse-bridle head-halter with the hard rubber mouthpiece connected to the reins. The special blinders they have on prevent them from seeing at all. They will have to trust the driver to guide them with the whip.

I helped prepare them and brushed them down. Tight corsets are fitted to push their tits up and out, make running even more difficult. The ones with big jugs get bridles attached to their nipples, and the ones that have little boobs have an attachment applied to their clits.

The ponygirls had bells on their nipples so they would jingle in time together as a paired set. Most had big asses and tits but the girls came in all shapes and sizes. Almost all of them were completely shaved but each pussy had a different shape and was designed to be the perfect wrapper for my dick.

I imagined the women living this way permanently. They looked pained at times, exhausted, and most of them appeared humiliated. There were some of course who were preened like show-offs, but there was something deeply satisfying about seeing these women paraded around naked, bound, and exposed.

They reminded me of “Sex-Donkeys” for lack of a better term, trotting and jiggling around, asses and tits bouncing. It was almost like the things that men desired the most were being used as weights that they had to carry around and show everyone.

I was certain it would have been deeply humiliating to be one of them. I was glad I wasn’t, and while I still felt some deep satisfaction and amusement over my Aunt and Cousin’s decision to be trained, I also respected them for actually doing it and not just talking about it.

My mom was an entirely different topic. She’s got big flabby knockers, a huge ass, and she almost seemed like a cartoon parody of a woman – big tits jingling and her nose and tits clipped, her hands bound as she struggled to pull a cart or a heavy weight.

I know on some level this was all embarrassing to her, and at the same time with my mom it was hard to really know if it truly was. I think she got off on it – thrived on being made to do these things.

She wouldn’t have woken up on her own and started pulling stuff around our yard in the nude when we lived with Jerry. The thought would never have occurred to her but even if she knew about this kind of kinky-stuff, I doubt she would have.

I think she LIKED being told what to do. I think that really is the difference between her and my Aunt. My Aunt wants to submit but she is still defiant. There is a smoldering anger in her pretty blue eyes even when she is behaving politely that makes me picture a caged tiger. She wants to submit, but a part of her is still my hard-ass Aunt Amanda.

I don’t know if that makes sense or not, if not – just forget I brought it up. I think about weird shit like that all the time. I don’t tell anyone – not even Mike or my Mom. My mom would listen, but I don’t think she’d understand what I am saying and I just think Mike has a lot of other stuff on his mind right now.

All I know, is that between the sisters – my mom and Aunt Amanda, there is a huge difference even though they’ve both been busting their asses to be good slaves to Mike and me. I’ve begun thinking of myself as their owner or Master on some level. Is it wrong for a son to own his mom?

I guess more like an Assistant to Mike, something like that.

The second race of the night would be for Pony Boys. It was a pure speed race for athletic skill and precision. They were expected to carry a woman on their back as a rider. At least the riders had stirrups to hold them in place but the straps that held the stirrups looked like they were uncomfortable for the pony boys. Still, none of them seemed to mind.

The final race would be individual pony girls, and it counted for a lot of points. It was through an obstacle course and then around the entire camp – long distance.

They planned a celebration at the end of the event. There would be drinking and lots of pot smoking. Uncle Evil loved to smoke dope. There was also going to be an auction, but I heard that money doesn’t change hands.

It is entirely voluntary, but the only currency is points earned during the games. The pony girls and pony boys go up for auction, and if you win the bid, you get to ‘take them for a ride’- that’s pony camp code for ‘fuck’ them.

Chastity and Joy had won a lot of points. I’d put them up for auction and would use the points they’d won, to bid on Barbara or Daphne if I could. I wasn’t sure if Mike would let me do that or not.

He told me that he had developed a core outline of Buttercup’s rules already. “I reverse-engineered your rules. I grouped different training techniques and punishments into four categories. There is pain, humiliation, sexuality, and obedience training.”

Mike also told me that obedience training covered everything from cleaning to speech protocol to bondage.

“Then within each category I ranked everything in terms of how intense the lesson is. A one is simple, and a ten is the highest score I can give something. He provided some examples.

Sexuality

Open Mouth Kiss is a 3

Blowjob/Dick Kiss is a 4

Eating Pussy is a 4

Self-Masturbation is a 4

Licking/rimming asshole is a 5

Masturbating others is a 5

Obedience

Standing in a corner is a 1

Light housekeeping in the nude is a 1

Yard work in the nude is a 2

Handcuffs is a 2

Hogtied/Tied to a chair for up to an hour is a 3

Caged for up to an hour is a 3

Mike told me adding more time or suspending someone upside down or by their tits would increase the intensity on his ranking scale. Mike’s ranking system was supposed to help him to decide the different limits he might give my Cousin in each phase of her training. I assumed it would also be used to determine what I would be learning about as well.

I quite seriously doubted she’d finish the first phase without chickening out. I could already see the look of bewildered apprehension on my cousin’s face starting to emerge. She was used to being in charge. If she wasn’t in charge she was the aloof one who wasn’t paying attention. This was an entirely new experience for Buttercup to put herself out there in a submissive role.

Mike explained to me that he was still working out the details, but a cock in the ass is more intense than a cock in a pussy. He wanted to think through it all so that he didn’t overwhelm her. “I want to push and broaden her limits, but only once she has the basics. This is like soup. You can add pepper, but you can’t remove pepper. If I expose her to something, there is no taking it back,” he said.

“I think Buttercup has the Internet. She knows about all the freaky shit out there,” I laughed.

“There is a difference between knowing about it and experiencing it personally. I am also concerned about my own son. I don’t want him in a psychologist’s office telling him how Dad fisted his sex-slaves in front of him at breakfast. I had intended to keep things to a minimum around you and Buttercup, but I’d rather answer your questions and teach you things in a proper order,” he said.

“Cool,” I nodded. I found it best not to try to talk like I was an expert or make suggestions. I could easily put my foot in my mouth that way.

Mike explained once she had a range of experiences to draw from, he could decide where to start Buttercup on her journey. I left it up to Mike to figure all that stuff out. I would handle keeping an eye on the girls while he tapped out his rules system.

Mike said it was like learning to use hand tools before you use power tools. “I am going to teach you how to use a screwdriver so you can appreciate the power drill so much more when you finally get your hands on it,” he said.

That made sense, but it seemed like a lot of work. I was pretty confident I could handle anything the girls did. Mike still didn’t let me participate in the orgies, the main-house, and the barn. I knew at night it was basically anything goes in there.

Any girl chained up in the barn could be fucked by anyone that wanted them. I was told it is basically a gang bang situation with bondage. Chastity and Joy were very popular, and I assumed almost all the campers at this event have had both of them multiple times.

The orgies in the main house were a little more organized. You also HAD to bring at least one female with you to get in. Every now and then, Mike asked me to drop the girls off at the main house, but only to fir them to serve and clean up cum. They were expected to walk around with trays and bring people drinks or to lap up any jizz that landed on the floor.

“Do we even know if Buttercup can handle a finger in her ass?” That was the one thing I was most curious about. I am definitely an ass man. I love butts! My cousin’s butt fascinated me. It was so small, perky, and I felt like she probably had never even had a finger put up that virgin turd cutter of hers.

“Buttercup, come here!” Mike called over to my cousin. She was talking to her mother and Chastity before the race. She turned, nodded and walked over quickly. She was still handcuffed.

Mike told her to turn around and bend over. “Spread your legs,” he said. Buttercup didn’t hesitate to obey. She did as she was told. Her butthole looked like bubblegum to me – pink and pure as Hubba Bubba.

Mike licked his finger and jammed it into her asshole and twisted it. No one around seemed to care. The pony girls had huge butt plugs with shaggy approximation of pony tails up their own asses.

“Oooooooooooooooooooooh,” Buttercup’s mouth formed into a perfect circle, and she let out a low howl.

“Is that going to be a problem?” he asked.

“Noooooooooooo, Sir” Buttercup’s mouth was still in an O shape.

“Uncuff her,” Mike instructed me. I pretended I’d forgotten my key and that Emily would be stuck there forever. A nearby Master offered me his casually, as if it was a can opener. I laughed and said that I’d had mine the entire time.

When I uncuffed her, Butter held her position. Mike told her to stand up and he plucked his finger out of her asshole. “Open wide, Butt” he said.

She made a disgusted face and scrunched her nose, but she opened her mouth. “If you don’t like the taste of your own peanut butter then who else would?” he asked her as she closed her mouth around his finger and sucked it clean for him. “Very good,” he said as he withdrew his finger.

“Now stick your own finger up your ass and keep it like that until I tell you to take it out,” he said.

Buttercup grinned a little and dunked her finger in her butt. He sent her back to her mother to keep talking to her before the race. Mike leaned into me and said, “I am starting to think she is actually serious,” he chuckled.

I liked being the one person Mike confided in. He was a strong father figure type. I’d never had that before. I didn’t want to ruin the moment by telling him that or anything though. I chuckled like he did. It was nice watching my cousin walk around with a finger up her own butt.

Courtney and Stefan were allowed to return so they could watch their mother’s triumphant victory over her fellow ponies. They talked to my cousin as well and seemed to accept her decision to be a submissive. Courtney giggled and seemed even more interested in Buttercup now. The two of them had had this weird lesbian-crush vibe going on, even before Buttercup started trying to prove she could be trained.

I started calling my cousin Butter or Butt for short. You may see me do that as I continue telling you how things shook out after my cousin made this startling decision. If I got angry with her, I called her Buttercunt, and she let me get away with it. I can’t tell you in words that adequately describe how happy that all made me.

Girls pulling heavy wagons with their tits bouncing as their bodies strained to move a heavy object, was interesting to watch. I admit I didn’t care much for the pony boy competitions, but Courtney and her brother watched them intently, so I did as well. I was mostly looking at Courtney’s pretty little tits to be quite honest. I think she knew that and didn’t care.