Whitey Winn One Shots

Maybe you should have been more careful what you asked for

Whitey sat in the office. Minding the one prisoner they had locked in the cells. A girl had come into town and there was a wanted poster out for her. So Bill grabbed her and shoved her into a cell. The issue was he then had to leave. Meaning she was left with Whitey Winn. Who'd been so desperate for attention lately he has actually begun humping his pillow at night. And he was... Loving her!

Y/n noticed Whitey staring at her from his desk. Rolling her eyes as she leant on the cell bars in her skirt and top. Knowing just from how his hand sat that he was stroking his cock through his pocket as he looked at her, "Something interesting over here deputy?" She teased him

Whitey stood up abruptly, his cock throbbing in his pants. He walked over to the cell, his eyes roaming over her body. "Well now miss... I reckon you know why you're here." he said, trying to keep his voice steady as he looked at her ass. He unlocked the cell door and opened it slowly. "But seeing as sheriff ain't back yet..."

Y/n figured immediately what was happening so she backed away from the door with a sly smile, "That so deputy?"

Whitey stepped into the cell, closing the door behind him. He leaned against it, his eyes never leaving hers. "Yeah... I reckon I could let you go... if you let me..." he trailed off, gesturing down at his crotch. His voice was low and husky, filled with desire.

Y/n licked her lips, a wicked smile spreading across her face, "humm well? Which would you rather cutie? My mouth, my hand or my pussy?"

Whitey's eyes widened slightly at her boldness, he was kinda assuming she'd have slapped him across the face or called him a perv but... she was... actually going along with it! For a moment his brain broke and he had to consider what on earth to say next... as he had no concept what to do now. Having never even imagined he'd get this far, but he quickly recovered. A smirk spread across his face as he considered her options. "Let's start with that pretty mouth of yours... Kiss it better."

"Then take your pants off, deputy" Y/n smirked, getting on her knees,

Whitey quickly undid his belt buckle and pushed his pants and boxers down to his ankles, his erection springing free. He stepped out of them, kicking them aside. He strode over to Y/n, his cock twitching with every step. He grabbed her chin, forcing her to look up at him with an intense gaze. "Well then baby... Let's see what you got." He leaned down, hovering his cock over her waiting mouth.

Y/n opened wide, enveloping his stiff shaft with her warm moist lips.

Whitey groaned as Y/n took him deep into her throat, bobbing her head up and down his thick length. He ran his fingers through her hair, guiding her pace. "Fuck yeah baby... Take it all. Show me that pretty little mouth of yours." Whitey's cock twitched in Y/n's mouth as she continued to pleasure him with her talented lips and tongue. He could feel himself getting closer and closer to the edge, "Damn baby... You're gonna make me blow my load... Gonna fill that pretty little mouth of yours."

Y/n kept going making sure to make him as happy as possible,

Whitey's breath hitched in his chest as Y/n took him deeper into her throat, her skilled tongue swirling around the sensitive head of his cock. He could feel the familiar tingle starting at the base of his spine, warning him of the impending explosion. He tried desperately not to cum so quickly but he was already surprised he'd lasted this long. "Fuck... I'm gonna cum soon..." Whitey's cock twitched in Y/n's mouth as he felt his orgasm approaching. He pulled her hair, forcing her to look up at him as he knew it was too late, his thick cum shooting out and filling her eager mouth.

Y/n swallowed greedily, savouring every drop as Whitey groaned in pleasure, his spent cock slipping from her lips with a pop, she stood and kissed his lips letting him slowly make out with her in his lusty state. Y/n took the opportunity while Whitey recovered from his orgasm and while he kissed her so deeply, to grab the keys for the cell and bolting for the door managing to get out and slam it shut locking Whitey inside seconds before he grabbed her. "Hummm Hiya deputy. Looks like you got a little distracted." She teased,

Whitey's eyes narrowed as he glared at her from behind the bars of the cell. He could still taste her on his lips and it only fueled his anger. "Damn it Y/n... You better not think this is over. I'll get out of here and when I do..."

"you'll what? Spank me for being such a naughty girl?" She teased,

Whitey's face turned red at her words, his cock starting to stir again at the thought of punishing her. "Don't tempt me little girl... I'll think of something a lot worse than spanking for you." He growled, his muscles tensing as he tried to find a way out of the cell.

Y/n smirked and cupped his hardening cock through the bars

Whitey gasped as Y/n's hand wrapped around his sensitive length, her touch making him weak in the knees.

"Mmm I bet you're a lot of fun to play with deputy... Wanna see how bad I can make you squirm?"

Whitey's eyes rolled back in his head as Y/n continued to stroke him through the bars of the cell. He could feel himself getting harder with every pass of her hand, his balls tightening in anticipation. "Damn it Y/n... Stop teasing me before I lose my mind. I need to fuck you so badly right now..."

"Want or need Whitey?"

Whitey growled in frustration, his cock twitching in Y/n's hand. "I need to be inside you, You're gonna make me beg aren't you?"

"humm Y/nbe... Or maybe I'm gonna make you cum so much you'll be begging me to stop." She smirked grabbing some handcuffs and cuffing his wrists to the bars so he couldn't move back. Then knelt on the floor kissing his cock.

Whitey's breath hitched as Y/n knelt before him, her lips wrapping around the head of his cock. He groaned loudly, thrusting forward helplessly as she took him deep into her warm mouth. "Fuck yes baby..."

"How many times have you ever come in one day Whitey?" She cooed between paused sucks and kisses,

Whitey's hips bucked wildly as Y/n continued to work him over with her mouth. "Shit..." he panted, trying to focus on her question. "I don't know... maybe five or six times? Fuck I'm gonna blast my load... You're gonna make me lose count for sure..."

"five? Sounds too easy. Let's say... Ten and then we'll see if you have enough strength to fuck me."

Whitey whined but almost buckled his knees, With a loud cry, his cum shot out in long, intense spurts as he came in Y/n's mouth. "Fuck... fuck... fuck... please... please... Mercy."

"Mercy? Already?" She cooed, "You're the one who came asking for attention. Maybe you should have been more careful what you asked for." She winked before she started again,