by Meg Jackson
“Oh, fuck, girl,” the Sheriff said, then grabbed me and pulled me towards him. He began kissing my neck and fondling my breast with one hand, the other wrapped around my waist. As much as I hated the Sheriff for keeping Cash locked up, my body was reacting to the attention all the same. He licked my earlobe and I moaned. Pulling away, the Sheriff put both his hands on my tits, fondling them and brushing my nipples with his thumbs. I shuddered.
“Oh, you are bad,” the Sheriff said. “Maybe you do need a little punishment.” I panicked for a moment, wondering what I’d gotten myself into. The Sheriff grabbed my hand and pulled me towards the desk. I nearly crashed into the edge, but right before I collided with it, the Sheriff pushed my shoulders and I fell over the desk so that I was leaning over it.
“Oh, Sheriff, how are you gonna punish me,” I said, wiggling my ass.
“There’s only one way to punish bad little sluts,” he said. I felt his hand grab my ass roughly, massaging it through my jeans. Then, I felt him pull my shorts down entirely, leaving my ass exposed. I looked at him as he rubbed my ass cheeks; suddenly, I felt a sharp slap against my butt and squealed. Another slap followed, and then another. I was shocked at first, not expecting it, but the more he spanked me the more it felt good; it kind of left a stinging, burning sensation that made me crave another.
“Oh, thank you, Sheriff,” I moaned, leaning forward further onto the desk so he had better access to my petite ass.
“Bad little girls can only be taught one way,” Sheriff said, spanking me yet again.
“Teach me, I’m such a bad little slut, Sheriff, please,” I moaned, crying out as he spanked me again. I felt his other hand on the small of my back, pushing my body down as he slapped me again and again, each time making me want another even more.
“Are you gonna keep being such a bad little slut?” the Sheriff barked.
“Oh, no, sir, I promise I’ll be a good little girl from now on,” I whimpered, wiggling my ass, needing another spanking. I was disappointed when another slap never came; instead, the Sheriff’s hands were rubbing my ass again, spreading my cheeks wide.
I felt one of his fingers dip into my slit, which was gushing at this point with both my own juices and Cash’s cum. I panicked for a moment, thinking that the Sheriff might realize what I’d just been doing, but he didn’t seem to notice. Then, I was surprised to feel his finger slide up to my asshole.
I felt his finger circling it, wetting it with my own juices; he dipped his finger in my pussy again and did the same thing; this time, though, he pressed his finger ever so slightly into my asshole. I realized what was going on and tried to stand up but found I was pinned against the desk by Sheriff’s hand on my back.
“No, not there, please, I’ve never been fucked there,” I pleaded, looking at him over my shoulder. He looked up at me and grinned.
“You’re telling me a bad little girl like you never had her asshole fucked before?”
“No, sir, I swear, never,” I moaned. Despite my fear, the Sheriff’s finger in my ass didn’t feel that bad. In fact, it felt kind of good. He pushed it in farther and I moaned again.
“Sounds like you kinda like it,” Sheriff said. I could hear him smiling from behind me.
“Oh, yes, sir, that feels good, sir,” I moaned as he pushed his finger even deeper. The sensation was a lot different than having a finger in my pussy, but it felt good all the same. Sheriff removed his fingers and I heard metal clinking. Looking back again, I saw the Sheriff pulling his handcuffs from his belt.
“Sir…” I started to say, wanting to stop him before things got out of hand.
“Shut up and I might let your boyfriend go,” the Sheriff replied, in a tone that was no longer so friendly. I knew this was my one chance to help Cash, so I obliged by crossing my hands behind my back. The metal felt cold on my wrists as the Sheriff locked them into place. Then, I felt him pull me upwards; I jerked up and almost fell back into him.
He began pulling me out of the office and into the hallway. I didn’t dare speak, in case I angered him. He pulled me through another doorway and I heard low whistles and hooting before I saw anything. The corridor along which the Sheriff was taking me was a holding cell; there were inmates in a bunch of the cells, and as I walked past them they all rushed to the bars of their cages.
“Whoo! Looka dat!”
“Fine piece of ass, Sheriff.”
“Yeah, fuck ‘er good.”
The remarks came from all over, and even though I was mortified by being dragged along, naked and handcuffed, before a prison full of inmates, I couldn’t help but be slightly turned on by the way my body was being exhibited. The Sheriff stopped before an empty cell and pushed me into it. There was a bed, a sink, and a toilet, and nothing else. The cell next to it was empty, too, but the cell across from it and the next cell in the line were occupied.
The prisoners inside rushed up to the bars and looked on eagerly. The Sheriff pushed me up against the bars; my tits were squashed against the cold metal, and the sensation sent tingles throughout my body.
“This is where we put all the bad little girls,” the Sheriff whispered into my ear. I heard him unzipping his pants and soon felt his warm, hard cock pressed against my ass cheeks. My face was pressed sideways against the bars; out of the corner of my eye I could see the man across from me starting to play with his package.
“Yeah, fuck that ass.”
“Gimme her, lemme show her a real cock.”
“I’d fuck those titties til tomorrow.”
The prisoners kept yelling, and the way I was on display like a piece of meat started to get me very horny. One of the bars was directly between my legs, and I could feel it pressing against my clit. Without even thinking about it, I started rubbing against the bar, allowing the cold metal to slide up and down my clit, sending vibrations of pleasure throughout my body. I felt the Sheriff’s cock pressed against my asshole and shuddered; his fingers had felt good, but I wasn’t sure I was ready to take a whole cock into my virgin asshole.
He pressed harder and I felt the head of his cock enter my asshole; my body tensed but then relaxed almost immediately; I was still sliding my clit along the bar and I could feel my pussy getting wet. My hands were still restrained behind me. As the Sheriff began thrusting, slowly, further and further into my asshole I groaned; it hurt a little bit, but mostly it felt really good, especially while I was still rubbing my clit against the metal bars.
“Fuck, she’s loving it!”
“Yeah, fuck that slut!”
The catcalls and yelling only made me hornier as the Sheriff’s cock slid further and further up my asshole. It was a weird feeling, but I liked it a lot, and I found myself timing myself so that I slid down the bar at the same time he was thrusting into me.
“Do you like getting fucked in the ass,” the Sheriff whispered into my ear.
“Yes, sir,” I moaned, pushing harder against his cock.
“Louder.”
“Yes sir! I love being fucked in the ass! Please fuck me harder!” I cried out; a chorus of hoots and shouts followed as the prisoners began rattling their cages. I could see out of the corner of my eye that the man across from me had pulled his cock out and was pumping it furiously, watching me fuck myself against the pole while the Sheriff fucked my asshole.
“What kind of girls like being ass fucked?” the Sheriff whispered, starting to pump into me faster now.
“Bad little sluts, sir, dirty little sluts love having their asses fucked, please fuck me harder,” I cried.
“Fuck that dirty slut!”
“Jam it in her asshole!”
The shouts kept coming, and each one made me hornier and hornier. I slid up and down the bar faster now, too, meeting each thrust of the Sheriff’s cock in my asshole; I could feel the way his dick was stretching my virgin asshole. It felt amazing to have his big cock pumping in and out of my asshole while I rubbed my clit against the cold metal bars; the constant yelling of the prisoners turned m
e on anymore, and soon I was begging the Sheriff to go faster, and deeper.
“Please, sir, fuck my ass harder, please fuck me deeper,” I cried out. I could hear him grunting behind me. In front of me, the prisoner was jacking himself off furiously now, a lecherous grin plastered on his face; behind me, the Sheriff was grunting loudly and thrusting into me harder now.
Each time he pulled his cock away and then pumped it back in I could feel my ass contracting, and his thrusting slammed me into the metal bar, rubbing against my clit even harder each time. I could feel the familiar pressure of a climax building inside me and I couldn’t help but crying out at each thrust.
“Yes, Sheriff, fuck my little ass, please,” I moaned against the bars, to the pleasure of the inmates around me. I could hear the Sheriff’s breath getting quicker, and his pumps got even faster; he was fucking me deeply now, his whole cock pumping into my asshole.
“Yeah, fuck that dirty little slut,” a voice yelled; I pressed myself harder against the bar, relishing each stroke against my engorged clit as the pressure built further and further.
“Yes, Sheriff, I’m a bad little girl, please fuck me…fuck me…harde- oh fuck I’m comminnnng,” I screamed as an orgasm rocked me; I pressed my body harder against the cold bars of the prison cell as my orgasm shook through me, making me lose control of my legs and almost collapsing onto the Sheriff’s dick, which was still thrusting in and out of my ass, each stroke making me climax even harder; I couldn’t see anything, or hear anything, lost in the blinding pleasure of my clit against the cold metal and the cock in my asshole.
“Fuck you slut,” I head the Sheriff groan, and suddenly felt a stream of hot cum exploding inside me as the Sheriff came, released load upon load inside my once-virginal asshole. He grabbed my hips as he came, pulling me against his cock as he unloaded inside me. Finally, he released his grip and we just stood there, his dick still in my asshole, both breathing heavily.
Looking out of the corner of my eye, I watched the man across from me shoot his cum across the cell. I felt the Sheriff pull out of me and groaned as his cock popped out of my asshole. I heard metal jangling and felt the handcuffs release. Turning around, I saw the Sheriff staring at me with what looked like regret on his face. I looked back at him, putting on my best little girl face again.
“Your boyfriend?” He said, his face growing cold. I nodded, looking up at him wide-eyed. He stood for a moment longer with the cold look on his face, then I saw it soften.
“Okay. You know what? Okay. He can go,” he said with a sigh. My heart raced with joy as I imagined Cash running out of his cell into my waiting arms. A moment later though, my heart crashed as I realized what I’d done. What if Cash hated me for this? What if he thought I was just some stupid slut who’d do anything with anyone?
I let the Sheriff lead me back to the main office, ignoring the hooting and jeers coming from the prisoners as we walked. I could feel the Sheriff’s cum leaking out of my asshole and cringed, thinking that it could all have been for nothing if Cash decided he didn’t want me anymore. In the main office, I slipped back into my clothes while the Sheriff disappeared into the other corridor, the one were Cash was being kept. Soon, I heard them approaching down the hallway.
“Special circumstances…bail…insufficient funds for…rigamarole…” I heard parts of the Sheriff’s speech as they neared the main office. As soon as I saw Cash enter, I threw myself into his arms. The Sheriff sighed and took his seat behind his desk. I turned to him, gleeful.
“Thank you so…” I started, but he interrupted me with a wave of his hand.
“Just leave now, please,” he said. I grabbed Cash’s hand and practically ran out of the office, so glad to have Cash back, but also so worried to tell him exactly how it had happened.
Once we were in the car and on the road, I didn’t know what to say. Should I just blurt it out? Be tactful? Maybe I just shouldn’t say anything at all?
“I’m not gonna ask what you did for me back there, teacup,” Cash said suddenly, making me jump and pulling me away from my thoughts.
“Wh-what?” I asked, fear clutching at my throat.
“I said, I’m not gonna ask what you did. I don’t care. I’m just grateful. I know lots of ways to get around the law and, well, I’m just saying thanks,” he said, looking at me with that half-smile on. I melted in relief; I was so happy that I wouldn’t need to tell him, that he not only forgave me, but was actually grateful. I put my hand on his thigh.
“Of course, I’d do anything for you,” I said, meaning it with all my heart.
We drove back to the bar and promptly disappeared into the office, what I had come to think of as our love nest. I was tired from all the activity at the prison, and I sat on his lap as he looked through some papers. I still wanted to know more: what was the deal with this club, anyway? What did they do? Why was there always so much money lying around?
I pushed all that out of my head though, and relaxed, leaning back against Cash. I was playing with his vest idly, letting my mind wander, when suddenly I found myself speaking, saying something I’d long felt but been afraid to say.
“Cash, I think I love you.” He’d looked up at me, then back down quickly. He took a long sip of whiskey. My heart fell and I started to get up. He pulled me back.
“Don’t, teacup. It’s not that. I…well, I love you too, see. But it’s not that easy. It’s complicated. You wanna be with me, you gotta be with the whole club. I’m not just talking figuratively. You gotta swear to keep our secrets. You’ll know it all, but you gotta devote yourself to us. Entirely,” Cash said, looking at me with dead seriousness in his eyes. I nodded fervently.
“I will. I swear, I will. I would never hurt you, Cash,” I said, leaning in to kiss him. He pulled his head away.
“Not just that, teacup. You gotta be with the whole club, not just with our secrets. Do you get it?” He asked, eyes averted. I didn’t get it.
“No, I don’t understand, Cash. I mean, I like all the guys…” This was true. I’d spent a lot of time at the bar not just in the backroom. I had fun with the girls, and I had fun with the men. They were always nice to me, joking around, never too crude. I especially liked Tux, who’d followed Brian home, and a few of the older men who seemed fatherly to me.
“If you wanna be my old lady, you gotta prove your loyalty to everyone, teacup. Everyone’s done it. I mean, the girls.” He looked at me again and it finally clicked. I jumped off his lap.
“What? You mean I have to sleep with everyone here?” I cried out, unbelieving. Cash nodded solemnly. I was shocked. “Why would you even want that? Why would you want them touching me, if I’m yours?” Cash’s eyes grew hard and cold at that.
“Because they’re my family. We share everything. We’re not just a club, teacup. We’re brothers. Every time you touch one of them, it’s like you’re touching me. If you don’t get that, then you should leave. Now.” His tone was stern, serious, and I felt my resistance wilting.
“Well…I mean…how does it work? Is it like…one at a time or…or can I get it all done at once? Is it forever? Do I always have to….whenever someone wants….” I had so many questions. Cash’s eyes lit up and his face softened as he realized I was actually considering it. He gave me that damn half-grin, and I realized there was nothing I could do. I loved him too much. And if that meant I had to pleasure every man in that bar, I’d do it.
“All at once. And there are rules. Younger guys, they don’t get certain privileges. They know the rules. You don’t have to do anything, teacup, just be there. And do your best,” Cash said, staring deep into my eyes. I walked back towards him and straddled him in the chair.
“And then we can be together? For real? Officially?” I asked. He nodded. I took his head in my hands and pulled him in, kissing him softly on the mouth. Pulling back, I smiled.
“Okay. Okay, Cash. I can do this,” I said. And I knew it was true.
We were standing outside the bar that I had come to kn
ow and love so well.
“Teacup, you’re gonna do just fine. You’ll see. Once you’re in, you’re in, and you’ll be taken care of. All our secrets will be your secrets. Every man in the club will have your back. I promise. And you’ll never have to do it again. Unless you want to. Some of our ladies, they like us so much they do it all the time. But you don’t have to and I won’t love you any less,” Cash said as we stood outside the bar.
“But, I mean, there’s just so many…I don’t know…” I said, biting my lip. I looked into Cash’s eyes and thought, for the hundredth time, how strange it was for me to end up here. How did a good, suburban girl like me get involved with a biker gang? And why didn’t I care to find out the answers?
“There’s only ten official members, teacup. And you’ve got two hands, a mouth, a pussy, and an asshole. That’s five ways to pleasure a man. It’ll be over in a jiff. And don’t be surprised if you find yourself not wanting it to end. You might be…impressed by some of the men in there,” Cash said with his half-grin.
I smiled up at him and nodded. He grabbed my hand and led me up the porch and into the bar. The familiar faces of the bar were there, standing around talking in low voices. They straightened up as soon as I entered, and I heard a few wolf whistles. They made me blush, but the men’s eyes on my young body was more exciting, and less threatening, than I’d pictured. They’d rolled a bike into the center of the bar and Cash guided me towards it. I noticed that there was a camera set up and shot Cash a look.
“Need it, baby, for insurance. Sorry. I promise, it’s not getting out,” he said apologetically. I accepted this information without question, as I’d grown used to doing when it came to Cash and the club. I hadn’t been told exactly how it would all work, so I followed Cash’s directions when he told me to get on the bike. I felt the cold leather against my exposed pussy and gasped, which drew some smiles from the crowd. I blushed. Cash took my chin in his hand, pulling my face towards him, then leaned in and kissed me gently.