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Story: There's a Way

Master took a few steps back and looked down. “Well well well, it seems the lad might be a right faggot after all, coming with a cock down his throat. All fours little faggot, and lick yourmess up. Ships have to be spotless lest the rats take over, so get to it, lad.”

I shook my head no and he grabbed my nipple to pull me up, and then grabbed my balls and squeezed until I screamed for real — no words, just all the agonizing pain I was feeling coming out because it fuckinghurt.

“Nod your head lad — you gonna lick your mess up if I let go?”

I frantically nodded, he let go and moved to the side, and I went to all fours and started licking.

“Smart lad. Later this evening you’ll get the strap for every second I’ve had to squeeze your balls. We’re up to nine seconds. I didn’t get off yet, but that’s okay. Polish the mat with yer tongue and then walk to the bottom of me bed.”

Most people think the old-timey thing that locks a person’s neck and wrists between wooden slats, so they’re forced to bend over, are called stocks, but they’re actually called a pillory. Stocks hold a person’s wrists and ankles while they sit on their ass.

There’s a pillory made into the footboard of the playroom bed, designed so you can stand on the floor and have to lean over for it, or kneel on the bed with your wrists and throat in it.

Today, it appeared I’d be leaning over for it, so Master could fuck my ass while I was all locked up in it.

Did I want to fight him, or merely refuse to lean over and put my neck and wrists in, or should I comply?

I absolutely didn’t want my balls squeezed again, but Master would enjoy this more if I didn’t comply, so when we got to the bed, I ran to the door and tried to open it, but of course it was locked and I couldn’t get out, so I sat on the floor, grabbed my nuts, and rolled into a ball to protect them while begging, “Please don’t, Sire! Please find some mercy and don’t buggerme again! Please, Sire! I’m already so sore back there, I can’t possibly live through it again!”

Master didn’t chase me, which surprised me, but then I looked up to see him settling the wooden pony under the winch, and I wanted to kick myself. Why hadn’t I remembered that riding the wooden pony was originally some kind of demented medieval torture? Hell, it’d probably been invented long before then, but it was for sure used before and during the time period Master and I were in.

When Master came to get me, he pushed my chest to the floor, connected my wrist cuffs together, and snapped a circular clamp around the top of my balls — a clamp with a leash already attached to it, so I had no choice but to scramble across the floor on all fours rather than have him pull my balls off. There was no time to stand, I just had to crawl as fast as I could to keep up.

Chapter 24

Will

I knew Davy had run away to please me, to make the evening more fun for me, but it was still important I show I was in total control. My wooden pony has all kinds of toppers to go on the board, and today I chose one with a softly angled point — thin enough it would get between his balls, but rounded so there wouldn’t be any true damage so long as he didn’t spend too much time on it.

I stood him up under the winch, looped his wrists over the hook, and then lifted it until he was on tiptoe. I removed the clamp around his balls and slid the pony between his legs, which spread them, and then finally lifted the apparatus to the predetermined mark, which put his weight on the pony. He lifted himself with his arms to hold himself off it, and I moved a chair in front of the pony so I could sit and watch the process.

“When you’re ready to put your head and wrists on the pillory so I can lock you in, let me know.”

Three and a half minutes later, “I’m sorry, Sire. I’ll position myself for the pillory. Please let me off this contraption!”

“Not quite yet, but it’s good to know we understand each other a little better.”

It took eleven minutes for him to finally allow his full weight to rest on the pony, his arms sagging above him, and I waited another ninety seconds before I walked to him and lowered the pony before pulling it from between his legs.

I put my arm around him before using my remote to lower the winch. I released the carabiner between his wrists while my boy leaned heavily on me.

“Walk to the pillory and settle into it as ye promised, lad.”

He did so, and I brought the piece down that would lock all three appendages in place — both wrists and his neck.

His cock had gone soft on the pony, and normally I don’t care much whether he’s hard or soft when I play with him, but for this kind of scene I often break my own rules, so I grabbed him and jacked his cock a dozen or so times until he was well on the way to hard.

“You fucked the girl you’re to marry yet, lad?”

“No, Sire! Not until we’re married!”

“Odds are, if I allow ye to return when I’m done playin’ with ye, she’ll be married to someone else by then.”

“No, Sire! She loves me, and I love her!”

“So, ye’re a virgin all around. The cook has a girl he keeps in his cabin. I might barter with him so we can watch you fuck her in a few weeks’ time. How many licks of the strap did we decide you were getting?”

“Nine, Sire.”