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Jessica in Jail - Part One
Jessica in Jail - Part One

Jessica in Jail - Part One

apemannAndy (Formerly Apemann)


It was all a stupid misunderstanding - more on the cop's part than mine - but he still hauled my ass to the local jailhouse in some Hicksville town in the back-of-beyond. I was furious, ready to sue every mother-fuckin' son-of-a-whore between here and hell and back. But...things turned out better than expected... much better than expected.

He was little more than a kid, the cop, and seemed almost embarrassed to have me in his custody as he led me to the cells. He blushed as he explained that due to the sheriff trying to prevent a couple of local gangs getting involved in a huge fight at a out-of-town bar, he'd hauled in about fifteen known members of one gang and incarcerated them in the jail for their own good. The jail, though, had another cell, he explained and I'd be in one on my own. I sarcastically thanked him for his consideration as the steel bars slammed behind me. Fuck, it was gonna be a long night. I turned my back on the bunch of Neanderthals who began wolf-whistling and cat-calling as soon as they saw me, and lay down on the uncomfortable bunk.

It didn't do me any good when I closed my eyes and tried to will myself to sleep. I could hear the guys in the adjoining cell, and what they were saying. "Oh, man, I'd love to have me a piece of that ass" one said. "Yeah, man, and I bet she has a real sweet pussy, too" another said. Aggressive male laughter erupted from the groups as one after another they speculated on various parts of my anatomy. As hard as I tried to shut them out, I couldn't. And, to be honest, I was getting kinda turned-on, too... I love my body, and I sure as hell liked fucking! Then one voice called through the bars to me.

"Hey honey, c'mon now, don't be shy. Instead of just layin' there all lonesome, come and talk to us" It was a nice voice, with a slight drawl and sounded educated. I was bored and, now that my anger had lessened, was feeling real down. I turned and sat on the edge of the bunk. A cheer went up from the guys in the next cell.

"So, what's your name, honey?" a good-looking guy with the educated voice asked.

"Jessica" I answered, smiling at him, feeling a familiar ache start low down in my pussy. Shit! Two sentences and I was getting horny.

"So how did a pretty little thing like you end up in a jailhouse?" Mr. Educated asked.

I spent the next ten minutes explaining how the sheriff's deputy had picked me up allegedly for soliciting! I had all of their attentions, and they were all angry on my behalf and offered to sort out the deputy when he returned. I laughed and said that that would not be necessary. I asked why they were all locked up and they told me that their gang was at war with a rival gang and that evening they were gonna 'sort it out once and for all' but word had leaked out and the sheriff had pulled them all in for their own good. Angry mutters and threats were muttered by some of the guys but Mr. Educated told them "to shut the hell up" and they did. Just like that. Man, this guy was getting my pussy wet!

"So, Jessica, what do you do for a living" he asked, winking at me. I just looked at him, curling the corners of my mouth in a slow sexy smile. "Can't you guess?" I teased.

I was still wearing the clothes I wore to work that evening: a short, very tight black leather shirt that clung like a second skin to my slightly-too-large round ass. My panty-hose was sheer, showing off my shapely legs, and the my six-inch high black stiletto heels gave extra length to them. The bustiere I was wearing was my favourite. It pushed my ample tits high up on my chest and showed plenty of cleavage and I could feel several pairs of eyes boring into me as I talked.

"Well, you're no secretary" Mr Educated said, laughing, "and you look too classy to be a whore" he added. Some of the other guys called out other ideas. Then a huge black guy, who had said nothing since I'd arrived, spoke in the deepest voice I'd very heard.

"She gotta be some kinda exotic dancer" he said. I smiled at him, giving him the full benefit of several thousand dollars worth of painful dental work. He looked shyly at me and quickly turned his head away.

"He's right" I said. "I dance at an exclusive club for executives and other well-placed businessmen" I told my captive audience. I explained that the club was invitation only, and there was a $500 entrance fee for each visit. Boy, did that ever get their backs up! The guys all began to shout and talk at once, saying how fucking outrageous it was and other shit like that. Mr Educated eventually calmed them down again.

"It's gonna be a long night here, Jessica" he said, slowly, "so do you feel up to giving us a demonstration?"

"What, dance for you guys"

A chorus of cheers and 'go on, do it' type comments erupted. It didn't take me long to make up my mind . I was becoming hornier by the minute and some of those guys were hot looking. Mr Educated had one of those faces that made me want to get down on my hands and knees and begged to be fucked, rough and hard!

"Sure, why not?" I said. A huge, very loud, cheer went up, "but you guys have gotta do something for me" I added. They groaned. "I like cock. I LOVE cock!" I told them and they cheered again. "I wanna see cock. I wanna see you guys whipping yours out and beating-off as I dance. That's the deal" I said. The groan that went up sounded like the jailhouse was collapsing. I sat down on the bunk again, feeling horny, as the guys huddled together, talking quietly. One or two of them, I could tell, were dead set against the idea and the other guys were trying to talk them into agreeing. After about five minutes, they all high-fived and Mr Educated turned around and spoke to me.

"You've got a deal, honey" he said, giving me a dazzling smile that set my pussy on fire.

I wasted no more time with words. I stood up and positioned myself a couple of feet away from the dividing mesh between my cell and the guys'. I began to slowly gyrate my hips, provocatively pushing my pussy forward while at the same time stroking my tits. I felt my pussy getting wetter as I saw some of the guys start to stroke themselves, their bulges growing in their pants. The biggest bulge was Mr Educated's I noticed.

"C'mon, guys, let's see some cock" I called out as I began to slowly unfasten my bustiere. It had easy to open 'hook and eye' fastenings, and as the first one popped open, so I saw the cocks begin to appear. My pussy was getting wetter by the second as my fingers undid more of the fastenings, revealing more and more of my creamy-white flesh and my tits. All fifteen guys were lined up along their side of the mesh divider, cocks in hand, beating off as the last fastening came undone.

I could hear the guys as they commented on my body. I casually threw the bustiere aside and reached for my tits. I moistened a blood-red painted fingertip and lightly stroked it over the pink nipple of one tit. Immediately, my nipple stiffened, standing hard and proud from the slightly darker aureole. I smiled as I felt thirty unblinking eyes watch my fingers pinch and stretch my sensitive buds. I pouted my lips, thrust my hips suggestively forward and laughed at the collective groan that went up from the other side of the mesh. The sound of fifteen cocks being simultaneously jacked off was something else, too. The groans of pleasure, the heavy breathing and panting were making my pussy wetter than I could ever remember it getting.

I slid one hand off my tits and stroked it over my flat stomach. I toyed with the belt buckle that was strapped around my slim waist before sliding my hand over the soft leather of my skirt. As my fingers played with the hem, the guys all seemed to hold their breath at once., waiting to see what I was going to do next. I slowly raised the hem.... very slowly.... and gave them a glimpse of the red trimmed, black lacy panties I was wearing. At least three or four of the guys let out deep groans as they came. My pussy felt on fire as I slid a single finger along my crotch. My finger was damp when I removed it and slid it between my lips and smiled sexily.

I turned around and presented my back to the guys, then bent forward, raising my plump ass high in the air. The chorus of groans and cries as the guys saw me reach between my legs made me smile. Guys were so easy to turn on! I eased one finger between the damp crotch of my panties and my wet pussy and slid it into my body. Even a couldn't help myself from letting out a small moan of pleasure as I fingered myself. More of the guys watching me let out loud groans of release as they jacked themselves to climax.

I flipped my skirt onto my back then hooked my thumbs into the waistband of my panties. I slowly began to ease them off my ass cheeks, revealing all of my wet glistening pussy as the guys looked on. I slid the panties down my thighs and allowed them to fall to my feet. I wiggled my ass, slid a single finger of one hand between my ass cheeks and lightly touched my asshole as I slid three fingers of my other hand deep into my pussy. The groans from behind me got louder and more desperate as I finger-fucked my own pussy and fingered my asshole.

"Aaaaaah, Jessica, babe!" one guy cried out "Aaaaaahhhhh.... FUCK!!!" he yelled and I heard several of the guys laughing at him as he moaned liked a wounded animal as he came. I slowly slid my fingers out of my pussy and fingered my swollen, aching clit as I stood upright again. I turned slowly around to face the guys again and licked each of my fingers in turn, The big black guy stared at me as if he'd never seen anything like me before, pounding his enormous cock as though his life depended on it, his eyes glued to me. Mr. Educated stroked his eight inch cock slowly, a slightly amused expression on his face as he watched me unbuckle the belt holding my skirt to my body. He winked at me and for the merest moment I felt my knees weaken. Damn, there was something about that guy that got me hot! My skirt fell to my feet and I gave the guys another good look at my wet pussy and ass when I bent over to pick it up.

I stood upright again and turned around slowly, giving my audience a good look at my body. I was now naked except for the heels. I stood in front of the guys, sliding my hands over my highly aroused body, over my large tits, tweaking my swollen nipples which sent small shivers through me. I slid one hand down my stomach and snaked my fingers through my neat triangle of pubic hair and quickly found my swollen clitty. I began to rub myself slowly, savouring the incredible feelings and the voyeuristic elements of having all those guys watching me. More of the guys were cumming as I masturbated, raising my personal pleasure level off the scale.

This was the most incredible experience I'd ever had and my clitty felt even more sensitive and aroused that it usually did. Mr Handsome was watching me intently, the hand stroking his beautiful cock moving in time with my fingers I noticed. The big black guy seemed to have not blinked once since I started and the hand gripping his massive cock was pounding his shaft hard and fast. His cock-head glistened, shiny with pre-cum and I felt myself becoming hotter as I realised what was about to happen. I rubbed my clitty frantically as the big guy's face screwed-up and a low rumble began deep in his chest. My eyes fixed on his thick cock as his hand moved in a blur. I felt my breath catch in my throat as he let his breath out in a loud hiss, like air escaping under pressure. Suddenly, the biggest and thickest stream of cum I'd ever seen erupted from the head of his cock. It shot into the air, through the mesh and landed wetly in my cell. Another thick load followed moments later and still he kept pumping himself. More cum shot from his massive cock and he hissed through his teeth, his eyes screwed tightly shut. I was rubbing my clitty frantically, so turned on at the sight of his cock cumming like that. I soon felt my orgasm begin to build inside me. Mr Handsome's face still wore that slight smile and he watched me intently as I rubbed myself.

He was the only one of the guys who hadn't cum yet and our eyes locked as I brought myself closer to orgasm. it was like he could see inside me, the intensity of his stare driving me crazy. My breathing became more ragged as my body tensed and stiffened. I saw pre-cum dribble form Mr Handsome's cock as I felt my pussy clench. I was only marginally aware that he'd begun to pump his cock faster and harder as my body spasmed and I cried out when I tipped myself into orgasm. I'd had many, many orgasms, but nothing prepared me for the overwhelming intensity of that one. My knees buckled and I sunk to the floor, my fingers still frantically rubbing my clitty as wave after wave of the most intense sexual sensations I had ever felt washed through my body. My eyes locked onto Mr Handsome and his hand that pumped his cock.

More pre-cum dribbled from its swollen shiny head and a broad smile split his face as he came. He stared at me, his hand moving rapidly as several long streams of creamy cum shot from his cock. My orgasm peaked and slowly died away and I sat on the cell floor panting heavily, watching Mr Handsome shooting stream after stream of thick cum onto the floor of the cell he was in. After what seemed like an impossibly long time, his hand slowed and stopped altogether and he released his semi-hard cock. It hung down in front of him, still swollen, still dribbling cum...

end of part one....

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About The Author
Andy (Formerly Apemann)
About This Story
23 Dec, 2012
Read Time
12 mins
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