Whitey Winn One Shots

Humilliated

I made my way into town on horseback as the sun was setting. I tied my horse Maggie to the post outside the bar where she could drink. I turned and quickly spotted where I wanted the sheriff's office.

I slowly approached seeing the lights on within. I stopped a moment just before the porch and I rubbed my eyes until they were red, and held my dress a little making sure to create the image I needed before going to the door giving it a few soft taps.

"Come in!" The voice calls from within so I headed inside see the typical sheriff's office set up and just a boy sat at the sheriff's desk. He had a small panflet in hand comic or news of some sort but closed It and set it on the desk "Ohh- well Hiya ma'am, you ain't a Labelle lady I know it?" He said as he looked at me a smile growing across his lips

"No, I was travelling it appears I've lost my way"

"AHH I thought I didn't recognize ya."

"This is the sheriff's office correct?"

"That it is ma'am."

"Ohh you must be the lovely sheriff then" I smiled moving closer

"you'd think that but unfortunately not, deputy whitey Winn, I am very pleasant to make your acquaintance"

"Aww well I was hoping for some help, Mr Winn"

"Of course, deputies have to help lovely ladies" he smiled getting up from the chair to stand at the desk

"Well I was travelling" I began moving my dress a little slowly exposing my unstockinged leg which immediately got his attention his focus was completely in me and my exposed leg he didn't notice as I grabbed my pistol from my thigh holster "and decided to rob this little place"

He sent to reach for his gun but I clocked my own pointing it right at his head

"Ma'am"

"Take off your gunbelt."

"Ma'am please -"

"Take it off."

"Alright -" he agreed keeping eye contact as he moved his hands to his belt buckle undoing it quickly and setting his gunbelt on the table

"Both of them Mr Winn"

He looked angry and upset but did as I asked trying to undo the other buckle at his back but immediately he struggled having to glance at it to undo it before finally sitting it on the desk

"Good boy" I smiled "Now get the keys and open up the cell" I ordered and he looked like he was gonna cry "Do it." So he took the keys and went across the office his face utterly frustrated and furious as he unlocked the centre cell and pulled open the door leaning on it "Go on in then" I told him and begrudgingly he went inside knowing he didn't exactly have a choice so I quickly went shutting the cell door behind him and locking it tight "there perfect."

"What are ya gonna do to me?"

"Nothing if you behave yourself" I smirked putting my gun away and even in this state he still looked

He came close to the bars grabbing them in his hands "I'm the law you can't just -" he began but I grabbed his shirt and kissed him for a moment he didn't kiss back but very quickly melted into the kiss kissing me back as much as I kissed him till I let him go "whoa-" he gulped "Hiya"

"Hi" I giggled

"I uhhhh I uhh I never got your name?"

"Y/n."

"Uhhh Hiya y/n. So uhh what's gonna happen now?"

"What Indeed" I smiled pulling him into and kiss which he happily obliged by moving his hands through the bars to wrap around my waist his thumbs stroking the boning in my dress groans and moans in his throat as we kissed but as we kissed I slipped my hand down grabbing my gun and setting the barrels end on his chest "back up"

"Okay. Okay." He nods moving back with his hands up

"Take off your shirt," I told him

"Ma'am please -"

"Now," I demanded

He grimaced but did as I asked removing his dark jumper with half buttons and of course, his badge revealing a once white button down

"Both of them" I demanded

He sighed but slowly unbuttoned his shirt and tossed it to the floor leaving his chest utterly exposed slightly pale where this skin never sees the sun.

"Good boy" I cooed "take off your britches"

"What!' he yelped already nervous crossing his arms over his chest

"Your pants. Off. Now." I demanded

He knew he didn't have a choice so rolled his eyes and undid his pants pushing them off and stepping out of them leaving him in only his brown dirty boots and his off-white cotton underwear

"Happy now?" He glared

"Very happy thank you whitey" I giggled

"Well now what now you've completely humiliated me"

I smiled grabbing his arm and pulling him back into a kiss which he happily kissed back into slightly moaning into the kiss as I stroked down his body giving his underwear a playful snap

"good boy" I cooed

"Uhh yeah- so uh what uhh what's your plan for me then?"

I giggled tapping his nose secretly grabbing a pair of handcuffs from the desk and unlocking the cell going inside with him

"Ohh... my my y/n" he blushed getting excited I smiled and pushed him against the cell bars and kissed him even more passionately he immediately melted wrapping his arms around me and stroking my dress often moaning into the kisses "ummmm y/n ummmmmm uhhhhh ummmmmm y/n- uhhh I can hardly contain myself for your kisses" he gasped

"Good" I smirked grabbing his wrists and pinning them above his head locking them each into the handcuffs around the cell bar so he has no choice but to remain in this position

"Oh god-" he gulped realising he was pretty fucked

"Now you going to behave for me whitey?"

"Not like I really have a choice do I?"

"No but still"

"Fine I'll behave"

"Good boy" I giggled kissing down his neck and leaving a trail of hickeys

"Ohh uuuuuuuhhh! Oh my god-" he groans "uhhh uhhhhh y/n!" He moans feeling my intense kisses so I continue kissing down his chest leaving a hickey between his pecks "ughhh! You are vicious!" He smirked but I just continued kissing and biting as his skin left a hickey on his V "ooooohhhh holy- ohhh my god! Yes! Yes! Ughhhhh please I'm begging you!"

"What whitey?" I giggled

"ummmm you know what I want." He smirked "Lower. Please. Just a little lower please" he gasped

"Awww well how can we deny such a sweet boy's requests" I giggled moving his underwear down and immediately I saw how hard he was he blushed but I immediately began to kiss him

"Uuuughhhhh! Uummmmm y/n" he groans biting his lip hard "More please!"

I giggled and took him completely in my mouth sucking gently as I moved my head

"Oooohh my god- yes! Yes! Oohhhhh holy fucking- uuuuuuuhhh uuuuuuuhhh uuuuuuuhhh-uuughhhh uuhhhh yes! Y/N!" He moans and I had to move back as his erection twinged and softened the moment I moved back his jizz sprayed out across the floor leaving him to slowly soften as he gasped desperately

"Ohhh my whitey someone was on a bit of an easy trigger" I giggled stroking his hair

"To be fair." He gasped "No girls ever did that to me before - and you are ... one hell of a tease. I'm surprised I lasted that long"

"Awww cute."

"Now what exactly are you gonna do with me?"

"I've already done it" I giggled unlocking his handcuffs and giving him a kiss "See ya around whitey" I smiled going to leave but he grabbed me

"You ain't going anywhere darlin'"