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Chapter 5
by ffq
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Lillian Holley, Ass of Crown Point (pt 1)
The past week had not been kind to former sheriff Lillian Holley. Dillinger's escape from her jail had rapidly turned her jurisdiction of Crown Point into a national joke. Headlines and radio segments buzzed about her failure to keep the notorious bank robber contained. Some of the very men responsible for those stories were in this very room. But what made it truly embarrassing wasn't how Dillinger managed to trick her deputies with a wooden gun, or even that he stole her prized Ford V8.
It was showing her literal ass to the whole town.
As a hostage, as sheriff, and as a woman, Dillinger made very good use of all three traits she carried when he **** her to aid his escape. She remembered the wind whipping her fat cheeks as Dillinger sped down the road, all of it stuck out the passenger side window while Dillinger kept his very real gun trained on her to **** compliance. The scandalized gasps from her constituents still rang in her ears. Fortunately, no cameras caught her display for posterity.
Unfortunately, there were plenty of cameras here to capture this one. She could hear them snapping away. See the bulb flashes against the wall. She knew exactly how it would look when those pictures ran in all of tomorrow's newspapers with some careful editing. But just in case she forgot, one of the nearby men kindly reminded her while talking amongst themselves.
"There she is. The Ass of Crown Point."
Lillian fumed. By court order, she had arrived at this function expecting a chance to tell her side of the story. Instead, she ended up in this degrading booth, her ass resting in a gap crafted to her dimensions. The court order said it very plainly. For failing in her duty, the Indiana Republican Editorial Association demanded her presence. She would present herself to these editors for the entire day in a manner befitting her job performance. During that time, she would remain available for direct feedback.
They looked so innocent at first read. If she had only read the fine print outlining each aspect in full detail.
"What can you expect from a Democrat?" an editor mused. "And a woman at that?"
She felt another hard smack and jerked, before righting herself. Only an hour in and her cheeks already throbbed. Her lips thinned as hands plied her ass apart. Every touch served as a grim reminder of how she ended up here.
"I'm stunned we were able to get her here in the first place. How did they get her to do this?"
"Dems are stupid, Carl. She probably overheard someone call her a jackass and thought she had to show hers to represent the party."
Their laughter stung more than her abused backside. At least until she felt something long, hard, and unmistakably wooden jammed into her tight asshole. In and out they went with it, testing her depths and what it took to make her anus clench in response. She hated the prop. Absolutely hated it. With her hatred inversely proportional to the unfettered joy felt by the editors screwing with her.
"Yours for the broom that swept the Statehouse Clean. Nice motto. I bet it gets lots of traction come election day."
"It'll get even more traction when we tell people every one of these has been shoved up the Ass of Crown Point. It's one thing to have a prop, it's another to have one personally 'signed' by the biggest failure this state has ever seen."
Up until now, Lillian Holley tried to let it all flow off her. They were Republicans, they said all kinds of horrible sexist things. But that last comment gave her pause. Had her thinking. 'Every prop gun? That's... that's...'
"FIVE HUNDRED?!" she suddenly shouted. Earning her a swift, sharp spank.
"Hey. No talking," an editor chided. "You did enough of it out of your ass before Dillinger escaped. It's our turn now."
"But. But five hundred. I don't think my body can- OW. OW! OOOWW!"
She recognized a paddle when she felt it. It hit much harder. Spanned much longer. Three strikes were all it took to make her shut her mouth.
"Where were we? Ah yes. I think we can ride this ass all the way to a majority. Maybe even a supermajority."
"We'll know for certain once it hits the papers."
The papers. Tomorrow's papers. Lillian envisioned that page so clearly. At the top, a headline like so many she had already seen. WOMAN SHERIFF SHOWS ASS. Followed by a large front page photo of that very ass front and center, perfectly positioned and framed for visual appeal. Rows of the wooden prop guns on each side. Giant banner proclaiming her as ASS OF CROWN POINT hanging above. And then her butt, the real star of the story, her gaping hole censored just enough to publish and put out on news stands across the state. Maybe the country.
She never set out to make a name for herself. The role of sheriff fell into her lap and she filled it. Yet she found a name anyway, as these prop guns filled her. She only hoped that she might one day live them down.
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FFQ Caption Collection
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Updated on Jun 18, 2025
by ffq
Created on Sep 15, 2020
by ffq
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