Jailhouse Blues

The year was 1893, and I rode into dusty Knoxville, Georgia in Crawford County at the end of a long day.  I boarded my horse for the night and found lodging in the hotel.  I cleaned up and shaved and headed downstairs to the restaurant.  After a meal, I headed out to the saloon for a drink and see if there was a card game going.

The saloon was crowded and they had a show going on with a guy playing piano and some dance girls.   I ordered a drink and looked around at a few card tables.  I saw one table with only 5 players and watched a few hands.  I noticed that one of the players looked to be a lawman of sorts.

While I wasn’t a card shark, I was pretty good at poker and asked if I could join the table.  They obliged me and I lost the first few hands.  My luck changed and I started winning.  It wasn’t long before I could tell that some of the other members weren’t too pleased with my good fortune.  I stood up to leave the game and head back to the hotel, when one of the other members stood up and drew his pistol.

“You’re a thievin’ card cheat!  I know that you are cheatin’ me out of my money.  Give me my money back or I’ll blow a hole through your cheatin’ heart, you son-of-a-bitch.”

The saloon got quiet as they watched this drama play out.  My hand was on my gun thinking about my next move.

The Sheriff, who was playing cards at our table, stood up and said, “Fred, what’s your beef here with our guest?”

“That low down varmint has cheated me out of my money.  I want my money back that he stole.”

“Fred, if you have a complaint, I suggest you put your gun down before you shoot someone, and make this a formal complaint.”

Fred put his gun back in his holster and said, “Sheriff, I want you to lock up this good for nuthin’ varmint for cheatin’ us at cards.  I want my money back that he stole.”

The Sheriff turned to me and asked me to stand up.  I slowly stood up.

“I know that you’re a visitor here in our town of Knoxville, but until I clear this up, I am going to need you to come down to the jailhouse.  Hands behind your back.  Now Fred, I’m gonna take these winnings back to the jail until I get to the bottom of your complaint.  Come see me in the morning.”

The Sheriff handcuffed me and lead me out of the saloon.  He took me to the end of the street and into the jail.  He took me to a cell and pushed me down on the cot and hogtied me up in the jail cell.

 “I’m sure that we will get this sorted in the morning, and you will be on your way, stranger.  I guess you and me will spend the night together.”

The Sheriff pulled out a whiskey bottle and took a swig.  He started playing cards until just past 11.  I was wondering how long the Sheriff was going to keep me tied up.  I was tired and ready to sleep.

 “Well, let’s see what sort of prisoner I got here tonight”, the Sheriff said as he came into my cell and untied me but left me handcuffed.

Damn it felt good to be untied.  What happened next was quite surprise.

“I need to search you, pard’ner, to see if you got any cards or other evidence of cheatin’ to clear you of your charge.”

The Sheriff proceeded to uncuff my hands and took me over to the cell bars.  He had me put my hands through the bars and re-cuffed me.  Next he started to take off my boots, my chaps, and my pants.  I protested but the Sheriff just kept on stripping me naked.

“Nope, no sign of cheatin’.  Like I said, I was sure I could clear up this misunderstanding and git you on your way by morning.  By the way, your boots and chaps look nice.  I think I’m gonna try them on.”

The Sheriff put on my boots and chaps.

“Damn I love wearin’ another guy’s gear.  How ‘bout you?”  He grabbed my nuts.  “Damn fine set of balls, cowboy.  Yeah, we’re gonna have a fun night ahead of us.”

The Sheriff put leg irons on me and a rope around my neck.  He uncuffed me and got me down on the ground where I was hogtied again.  The Sheriff kicked the crap out of me with my own boots and spurs and then made me lick my boots clean.

 “Yeah, cowboy.  Lick my new boots.  You like my new boots?  You may not be getting’ these fuckers back.  Make you leave town barefooted”.  The Sheriff laughed as I licked the boots.  “Yeah, lick my stud boots clean for me! Clean ‘em up good for me boy, this cowboy likes to look good in his slicked-up new boots.  Then ya got another job waitin’ for ya up a little higher....yeah, you been staring at the bulge in my jeans boy....you know you've been anxious to get your lips and tongue on it.  Shit watching you lick my boots gets my dick rock hard.”

He unzipped his pants and his rock solid manhood came out.  He rolled me over on my side and started stroking his cock with his pistol.

“You like the looks of my dick, fucker?  Shit, you know you’re gonna get this cock up your ass tonight?  Fuck yeah, this Sheriff is gonna get his prisoner to give me some relief.  Damn, it’s been too long since I’ve had a prisoner to get my dick up their ass.  Look at how rock hard I am.  Fuck yeah, I need some relief.”

The Sheriff put me back on the bars with my hands cuffed through the bars exposing my bare ass.  He took my gun belt and proceeded to whip my ass several times.

“How’s that feel?  I bet that hurts like hell!”  He whacked my butt again.  “Damn, I love the sound of leather on a man’s ass.”  Again, he whacked my butt.  “Shit yeah, boy.  Damn I love whippin’ a guy’s ass.”  Again, he whacked my butt.  “Shit, listen to the sound of that leather against your ass.”  Whack, he hit me again.

“I’m ready for a ride, cowboy.  Your ass probably hurts so much, you won’t even feel it when I fuck your brains out.”

The Sheriff lubed my fuckhole and rammed himself inside.  My ass did hurt, but not nearly as much as him ramming that huge cock up my ass.  I was gagged and tried to scream.  The Sheriff just laughed and rode my ass for what seemed like an eternity.  I felt his hot cum shoot up my ass.

“Damn yeah, boy.  That’s one fine ride your butthole has there.  I’m gonna keep you around for another ride tonight.”

The Sheriff strung me up in the jail cell and went to sleep.  I could hear him snoring.

After a couple of hours, I must have dozed up, I suddenly was awakened by the Sheriff untying me from the wall.  He thrust me onto the cot and tied me up again.

“Damn boy, I want another piece of your ass.  I’m gonna ride your ass again before the sun comes up and I have to let you go.  You ready to ride?  Like you have any option.  Hell, this is why I love being Sherriff.  Damn, I get to fuck any prisoner I want, and there’s nothing you can do fucker but take my shit.”

The Sheriff laid on top of me and thrust his cock up my ass.  He was still wearing my chaps and boots.  Damn it felt weird to be fucked by a guy, but was cool feeling those chaps and boots.

“Fuck yeah, cowboy.  Take my man meat up your ass.  Damn you are one helluva fuck.  I wish I could keep you longer.  We’d have lots more fun.  You enjoy having this Sheriff’s dick up your ass?  Shit yeah.  Oh fuck… fuck yeah… Damn I love riding your fuckin’ ass.  Ah… fuck… yeah… ”

And the Sheriff shot his load again.

The Sheriff pulled his dick out of my ass.  He then knelt at the head of the cot and forced his wet dick in my mouth.  He grabbed my hair and was forcing me to suck his damn cock.

“Yeah cowboy, suck this cock.  Clean my dick like you cleaned my boots.  Fuck yeah, boy.  I like getting my cock cleaned after a good fuck.  Ah… hell yeah… suck my cock… ”

The Sheriff stood up and zipped up his pants.

“Damn boy, I think I may need to find another set of charges to arrest you with so you don’t leave in the morning.  You might come to like Knoxville, boy.  Hell yeah, I might like ridin’ your ass every night.  You want that, cowboy?”

The Sheriff left my cell laughing.  Again, he sat at his desk and fell asleep.

Morning came and the Sheriff reluctantly gave me back my gear.  I was untied from the cot and allowed to get dressed.

After breakfast, the cowboy from the card game came in.  The Sheriff and him talked and the Sheriff gave him half his money back.  Told him he’d better learn to  play cards better and stop drawing his pistol unnecessarily.

After he left, the Sheriff let me go as well.  I immediately went to the hotel and grabbed my gear.  Then I went to the stable and saddled my horse and quickly rode out of Knoxville before the Sheriff changed his mind about letting me go.  I didn’t want to spend another night getting raped in his jail.  One night getting fucked by him was enough for this cowboy of the jailhouse blues.

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