I dropped off my netbook and my cigar play kit at the cabin. It was late, but I was awake. I decided to wander.
I didn’t go far. As I crossed the grass in front of my cabin, I saw people gathered in front of the horseshoe. Gray, Lochai, and Rough were there, smoking cigars and enjoying the company.
I took a seat. Pulled out my notebook. Wrote about my day.
As I worked, Rough called me over; he had a head of ash for my consumption.
After my treat, the back and forth to Oink began. Rough asked me to retrieve his wristband for the Whorephange game. Then he wanted his money from the packet. Then his leather wrist band. Then he sent one of them back. Once, I remarked to myself, Ah, the joys of service; I feel like a gopher. I laughed to myself and kept to my task.
As I nestled on the grass, Rough had me tear up the sheets of paper that were his money. He then needed to sign the back of each fake bill. As he worked, I offered him a business deal.
The rules of Whorephange stated as a bottom I won if I had the most money in the end. Rough could win if he had his signature on the most bills. I suggested Rough and I trade money. He’d have his name on twice as much fake cash to start. I would have a pile of fake cash to claim as my own.
Rough didn’t quite like my terms. He didn’t want a 1 to 1 deal. He wanted more bang for his buck. A 3 to 1 ratio was his preferred exchange. Since we each received $1400, Gray calculated this would be about $470.
“$500,” I countered.
“You want to go against Gray’s wishes?”
“Yes. I know I’ll pay dearly for that.”
I was sent back to the cabin, this time under Gray’s direction, to retrieve his big bundle of ow.
When I returned, Gray made me play a little game. First I picked three toys; they were immediately discarded. Next I picked two more. They were kept. Both were canes. The last toy I picked was the one Gray would use on me. The other cane was for Rough to use on me some time in the future.
Gray wanted me face down in the grass, but first I was to strip. As I gave my show, I turned my body so both Rough and Gray would enjoy the reveal.
Twisting my body, I got on my hands and knees, my head by Rough’s boots. Gray stood. Asked me what ratio of cane strikes I thought I deserved. I suggested 1 to 10.
“No,” said Gray. “You said one word that cost you. You said you’d pay ‘dearly’. One to one; thirty cane strokes.”
“That’s a lot,” said Rough. “I may get bored and just leave.” I looked up at him.
“Am I ever boring?” Rough gave me an intrigued look. “I am never boring.”
I laid in the grass.
Gray came down on my ass hard. I whimpered. Said, “One, thank you.” He continued.
I sobbed. I writhed in the grass. I counted each of Gray’s strikes and thanked him for each punishment.
Rough rested his boots on my back as Gray attacked my ass. Gray’s strokes grew worse and worse through to the final lashing blow. Once he finished, Gray sat back down and join Rough in his use of me as a foot stool.
When I regained my composure, Rough leaned down with a stack of money, signed. I had earned my payment. He said I could deliver his cash whenever; he trusted me. He stood, ready to go. I tried to peek under his kilt. He wagged his finger no at me, then left.
Gray, however, wasn’t quite done yet.
He stood up and began alternately caning and kicking me to the beat of the music playing in the background. He had me flip onto my back. And then he began kicking my cunt.
“Are you gonna cum on my boot?”
“If you let me.”
“Sure, but you have to do it before the song ends.”
I writhed my clit against the sole of his boot. Heard his instruction and let my orgasm fly. Squirmed in the grass as the pleasure raced through me. Smiled, happy and sore.
I tied up his big bundle of ow. Returned it to his cabin. Came back and saw my friend ArrogantSlut arrive.
“I was just stood up for my bootblacking,” he said as I re-entered the lounge area.
“No,” I said. “I didn’t stand you up. I was in the middle of a scene.”
I ran back to my cabin. Grabbed my bootblack kit. Set up in the grass by him. Began working on his shoes.
Gray was tired. He gathered his things, kissed me on my cheek, and headed off to bed.
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