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Jessica In Jail - Part Two
Jessica In Jail - Part Two

Jessica In Jail - Part Two

apemannAndy (Formerly Apemann)

The only noise to be heard for several minutes was heavy breathing as we all recovered. I was still as horny as hell, though, and seeing all of those delicious cocks disappearing back into pants was disappointing to say the least.

"I need COCK!" I said loudly, immediately regaining their attention. "Fifteen cocks and a hot wet pussy waiting to be filled. C'mon you guys, all of you can have me if you can get your asses in here!" I declared, sitting on the cell floor and fingering my pussy.

There was an immediate babble of voices as the guys called to me, one or two of them calling me unpleasant names, too, but they were shouted down quick-smart. One voice rose above the others and soon calmed them all down.

"Are you serious, Jess?" Mr Handsome asked

“Hell, yes!” I said smiling at him. “Seeing all you guys jerking off has made me hornier then I’ve ever been!”

Mr Handsome looked at me, that sexy small smile on his lips again. Jeez, but he had something that did it for me.

The guys stood around all looking at one another. A couple shrugged their shoulders as if to say ‘what the hell can we do’ while others suggested trying to break down the mesh between them and me. One guy went so far as to pull on it, but it didn’t even budge an inch. I just sat there, watching and listening, playing with my pussy and tits as they talked amongst themselves. Then someone suggested they needed to try and get the deputy to open the cell, somehow or other and others laughed at him. All except Mr Handsome.
“That’s not such a bad idea” he said over the all the other voices. Everyone immediately quit talking.

“What do you mean, man?” a Hispanic-sounding voice asked.

“If one of us was to suddenly become really ill” Mr Handsome said, smiling, “the deputy would have to come and see what the problem is, wouldn’t he?” Five minutes later a guy they called Bobby agreed to be the ‘victim’. I told them that whatever they did, they must not hurt the deputy. Mr Handsome assured me that they wouldn’t and winked at me again. He suggested that I collect my clothes and hide them, then cover myself over with the blanket on the bunk. I did exactly that as Bobby suddenly fell to the floor making horrible choking noises and thrashing about on the cell floor like he was having a fit. All the other guys set up a noise enough to wake the dead, which had its desired effect. The young deputy came a-running , took one look at Bobby and immediately ordered the rest of the guys back from the cell door as he unlocked it.

As soon as he knelt down to look at Bobby, the big black guy, the guys called him Brick, clamped a hand over the poor guy’s face and lifted him clean off the ground. The other swarmed round and one took his weapon off him and his night-stick, while another freed his handcuffs. In seconds he was securely anchored to the front bars of the cell, a torn strip of somebody’s shirt a gag across his mouth. He looked terrified.

“You’re not gonna be harmed” Mr Handsome told him gently. “We’ve been invited to a party with our neighbour” he added, motioning with his hand to me. A round of cheers went up along with good natured laughter. The deputy’s keys were still in the cell door lock and Mr Handsome removed them and with the other guys trailing single-file behind him, unlocked my cell door.

“Hello boys”, I said, throwing back the rough blanket that covered me, “Let’s party! They all cheered and crowded around me.

The bunk wasn’t fixed to the wall. As I’d never in my life been in a jail cell, I had no idea whether that was normal or not, but I thought it probably wasn’t. Anyway, what it meant was that, when about six of the guys lifted the whole thing up with me on it, I was deposited in the middle of the cell with fifteen guys all to myself! I was almost salivating with the excitement of it all. A few of the guys were wasting no time either. Several of them had already dropped their pants and were holding their swelling cocks.

“Just two rules, guys” I said above their chatter, “no kissing, and no cumming inside me. I wanna see all that lovely cream all over me, got it?” There were one or two groans of disappointment but they were soon drowned out by the others agreeing to my terms. Seconds later, it seemed, I was looking at fifteen cocks ranging in size from Brick’s huge black cock to the smaller but tasty-looking slim one of another guy who looked a bit shy to me. I wasn’t fussy: cock was cock whatever shape or size it was.

There were a few moments of awkwardness as the guys looked at me, not one of them making a move to touch me. I took the initiative and grabbed the nearest cock to me, which just happened to be Mr Handsome’s. I opened my mouth and swallowed the smooth shiny head, tasting his cum. He began to swell to full stiffness as I sucked him hard and as deep into my throat as I could take him. I felt hands grabbing at my tits and my legs being opened wide before the rough wet feel of somebody’s tongue licking greedily at my pussy made me feel wet and hot. Other hands were stroking all over my body and a felt somebody poking around my asshole. In seconds at least one finger was deep inside me and I moaned in pleasure around Mr Hansome’s thick cock.

Somebody complained that Mr Handsome was being greedy with my mouth so he slid himself out and was immediately replaced by another cock, slimmer and thinner than Mr Handsome’s. I was able to take it further into my throat and the guy was moaning like fuck as he felt my tongue lashing his smooth head and my teeth scraping along his length. In less than a couple of minutes I tasted his pre-cum and spat his cock out. He swore in frustration as he was elbowed aside by the next guy in line. Before I had time to draw another breath my mouth was filled with cock again and I sucked hard. I felt my pussy being stretched as a thick cock filled me. I couldn’t see who it was inside me but it felt good. He took long slow strokes, enjoying the feel of my tight pussy wrapped around his swollen shaft, holding him inside me. Hands took hold of my arms and I felt my fingers being wrapped around two more cocks. I started to wank them as another cock slipped into my ever waiting mouth.

My pussy emptied, but it was only seconds before another stiff cock filled me again. This guy was in a hurry and began to fuck me hard and fast, just how I liked it! His cock wasn’t very long as it didn’t seem to go very deep into my pussy, but it was thick and hard and it felt great as the guy fucked me. It couldn’t have been more than a minute later when he suddenly whipped himself out of me and I felt his hot cum splashing down onto my belly. I felt the cock in my right hand thicken and I rubbed my thumb over the smooth head. It was wet with pre-cum and the guy was moaning “make me cum, Jess” so I wanked him harder and faster, gripping his cock as tightly as I could. He cried out loudly as a thick wet stream of cum shot from him and dribbled down my arm and wet my hand. I continued to wank him until he went soft and he stepped away. My hand wasn’t idle long, though as my cum-sticky fingers were wrapped around another long thick cock. I looked up to see a guy who looked a little older than most of the guys. He winked at me as my hand moved up and down his shaft. I wanked him slowly, hoping that he didn’t want me to make him cum. I wanted that cock in my pussy!

My asshole was stretched wide enough for one of the guys to put what felt like three of his fingers in me. With yet another cock fucking me hard and now fingers rubbing my swollen clitty, I was on the edge of cumming. I felt the thick cock I was wanking with my left hand slip out of my grasp to be replaced my another one. The older guy looked at me again and winked once more. I let go of his cock and he stepped back. I saw him walk to my feet, then felt his hands stroking my legs before he carefully removed my shoes. I felt a new thrill buzz through my highly aroused body as his lips kissed my feet and his tongue licked each toe in turn, before his mouth sucked them.

One guy was sucking on my left tit as another sucked my right, drawing the nipple into his mouth and biting gently on it. The pain and pleasure were incredible and I felt my orgasm building to its peak. As the guy fucking my pussy withdrew and wanked his load over my belly, I felt a tongue lapping at my clitty. Suddenly my body spasmed and my mind went blank as I came. The guy whose cock I was sucking yelped in pain as my jaw clamped in reflex around it, but he didn’t try to remove himself from my mouth. If anything, he seemed to swell thicker and bigger! I had to let him go though as I needed get some air into my lungs. I gasped as a second, then a third wave of intense sensations washed through my whole body.

Seeing me orgasm seemed to tip both of the guys I was wanking over the edge as they both almost simultaneously climaxed in my hands. I lay on the bunk gasping and still shuddering from the intensity of my orgasm, thick cum running down my arms and covering my hands. I felt the fingers in my ass slip out. Another cock slid between my lips and I began to suck it. I felt my legs being raised into the air, my ankles resting on broad sweaty shoulders. Seconds later the unmistakable smoothness of a cock head was pushing against my asshole.

The guy was none to gentle as his length slipped into me and filled my ass with his swollen shaft. He started to fuck my ass hard, which drove me crazy. I wanked the two cocks in my hand as hard as I could and felt new fingers filling my pussy and rubbing my clit. I almost immediately had another small orgasm as the guy in my ass fucked me with a regular smooth rhythm. The cock in my mouth was replaced by another. The guy shoved himself deep into my throat which made me gag but I just sucked him as hard as I could as he face-fucked me. He was good, and knew just how far to push himself. His cock was quite long and quite thick and felt good in my mouth. I slipped the tip of my tongue into the hole on his shiny head and he groaned in pleasure. If I could have, I would have smiled.

The guy fucking my ass suddenly yanked his cock out of my body and cried out my name as his cum splashed onto my body. There was a lot of it and he moaned and made noises of pleasure as he wanked himself over me. It felt as though every inch of my body that was reachable was being touched, licked, kissed, touched, fingered or fucked and I was heaven! I felt another stiff cock slip into my pussy, then into my ass, then back to my pussy. Fuck, but that felt amazing! The guy doing it to me had obviously done it before as he never spent too long in one hole or the other.

The cock in my mouth removed itself and another quickly took its place. This one was probably the smallest of the cocks I’d sucked and the guy wasn’t in me very long before pre-cum started to dribble from his head. I licked it off and swallowed and was about to let him go when his hips suddenly jerked forwards and my mouth was filled with his cum. I swallowed it all, sucking the bastard dry before opening my mouth and allowing him to pull his wilting cock out. The guy had a smug look on his face and strutted away like he’d scored something over me. Fucking asshole!

The guy who’d winked at me and done things with my feet was still around and I was just about able to see him as he positioned himself between my wide-open legs. I held me breath as his long thick cock slid into me, filling me like none of the other guys had done. He began to fuck me with long slow strokes of his beautiful shaft. I felt my pussy tighten around him as he fucked me, like he had all the time in the world. I felt his gentle fingers feeling around my asshole before slipping into me. They began to move backwards and forwards, finger-fucking my ass as his cock fucked my pussy. Another guy began to rub my sensitive clitty slowly and lightly, sending me off into a dream world of amazing and fantastic sexual arousal. I flopped back as another load of cum rained down on my battered body, wallowing in the pure sensual pleasure of have my pussy and ass fucked at the same time as well as having my clitty rubbed. If I’d been a cat, I would have purred with pleasure.

It wasn’t too long before my body began to respond to all of the stimulation it was receiving. I felt my orgasm begin deep inside me and gradually build in intensity as the Winking Guy continued to fuck me and finger-fuck my ass. I raised my ass off the bunk, willing the guy rubbing my clit to make me cum. I felt his fingers press more firmly against my clit then moments later, it felt as though my body exploded as another incredibly powerful orgasm left me weak and delirious, writhing on the bunk with my pussy and ass still being stimulated. I felt the Winking Guy’s cock swell and thicken inside me, but he kept his same rhythm, sliding in and out of me for at least another minute before suddenly taking his cock out and grabbing hold of it with his free hand. He stroked himself maybe half a dozen times before he exhaled a loud breath and uttered a low groan as his cock gave up its load of cum which arced into the air and landed onto my cum-slick body. Still he continued to finger-fuck my ass as another load of cum followed the first, then another. Only when there was nothing left to come from his cock did he remove his fingers from my ass and stop wanking himself. He looked me right in the eye, winked again, then turned away.

The noise in the cell was quietening down as guys who had done whatever they wanted with me drifted away. Three or four more shoved themselves into me - my ass and pussy - before cumming over my tits and belly. I wasn’t at all surprised to find that the last two guys left were Mr. Handsome and the big black guy, Brick. Both of their cocks were rock hard stiff.

“Ever done a DP, Jess?” Mr Handsome asked? I just nodded, yes. It had been a while but it had also been incredible. Mr Handsome and Brick helped me to my feet and steadied me while Mr Handsome took my place on the bunk. I wasted no time at all in positioning my ass above his gorgeous cock and lowering myself onto it. He slid smoothly into me and eased me back so that I was laying on his chest. His hands immediately cupped my tits and began to tweak my nipples. Brick took his position between my open legs and pressed the head of his massive cock against my pussy lips.

I was blessed with a tight pussy and when he tried to slip into me he found that he was too big. I told him to not worry about hurting me, that I wanted his cock in me no matter what it took. he looked at me and I told him to shove that fucking thing in me no matter what. A small smile lit his face for a moment as he pushed his cock more firmly against me and I felt my pussy being stretched as it had never been before. Inch by inch Brick slipped himself into my body and I felt filled up as I have never ever felt before. Jeez, but it felt like something I could never have imagined as the big black guy began to carefully and slowly fuck me.

With my ass full of Mr Handsome’s swollen cock and my pussy stuffed full, I could barely move. Every movement of Brick’s cock sent incredible feelings through my ass as well, and all Mr Handsome had to do was lay under me. His hands were clamped to my large tits, teasing and pinching my nipples, stretching them painfully but it all felt so fantastic that the pain was wonderful; welcome even. I slid my hands over my body, rubbing in all the cum that was on me into my skin. I traced my hand down through my tangle of curly hair and found my sore, sensitive clitty.

I lightly touched myself as Brick slipped himself in and out of me. I urged him to fuck me harder, to slide his magnificent shaft as deep into me as he could get it. He looked at me as if to say ‘are you sure’ and I nodded at him frantically. I was rewarded with the feel of his cock slipping even deeper into me, deeper than any cock had gone before. I swear I was moaning with ecstasy as Brick fucked me, gaining in confidence when he saw that I could take every inch he had to give me. He started to move a little faster, his hip thrusts a little firmer. His face wore a look of grim determination as his massive cock fucked me like I’d never been fucked before.

My cum-slick fingers rubbed my swollen clitty frantically as the feel of Bricks cock in my pussy and Mr Handsome’s cock in my ass drove me to a level of arousal I had never experienced before. I was vaguely aware that the rest of the guys were watching the three of us as my frantic panting became the only sound in the two cells. I couldn’t have cared if there was an audience of thousands, just as long as the cocks that were driving me crazy stayed just where they were!

My whole body was a mass of super-sensitive nerve endings as I responded to the growing sexual tension the two guys and my own fingers were creating. Brick was fucking me harder and faster now, his massive thick organ filling my pussy with it’s meaty length. Mr Handsome was now moving his hips up and down, ramming his cock into my ass as far as he was able to. I placed my hands either side of his body and raised my ass slightly, which gave him more room to move. He immediately began to thrust his rigid cock harder and deeper into my ass, his hands squeezed my tits harder and I rubbed my clitty faster.

I felt my pussy tighten around Brick’s length as my orgasm began to build deep inside me. I was moaning and crying out, sweat dripping into my eyes as Brick pounded his massive cock into me and Mr Handsome thrust himself into my ass. My hand was a blur as I rubbed my clit, the tension in my body making my ass and pussy tighter still. Brick’s face was wet with sweat as he fucked me and I could hear Mr Handsome breathing heavily under me. The tension in my pussy was becoming almost unbearable as I willed myself to orgasm.

Just when I thought I couldn’t bear it another moment longer, my mind went completely blank and all that I was aware of was the pure sexual sensations flooding me to the very core of my being. I cried out loudly as wave after sensuous wave of release and pleasure swamped me. My pussy tightened around Brick’s shaft as he pounded in me. After three of four more thrusts of his hips he suddenly yanked his length out of me and a thick long stream of creamy cum erupted all over my chest and belly. Brick growled like an enraged bear as another load spouted from him, matching the first in intensity. Several more followed, smaller loads, and Brick grinned like a small child as his cock began to soften. I managed to find a smile for him from my haze of sexual ecstasy, still with Mr Handsome’s cock pounding my ass.

I felt his arms wrap around me as his hips thrust as hard as they could. I felt his cock swell tightly in my ass and he groaned loudly. I felt wet warmth flood my ass as his cock pumped its load into my tight passage. Still he kept pounding until I could feel his cum leaking out of me. He let a huge sigh of satisfaction when he had emptied himself into me and I felt his cock soften before it slipped out of me completely. I lay back and Mr Handsome moved across the bunk so that I could lay beside him.

We lay there for maybe ten minutes, not speaking. Eventually, he raised himself off the bunk, kissed me chastely on the cheek and rejoined the rest of his gang in the other cell.

I could feel the young deputy’s eyes boring into me as I stood and gathered my clothes.

“Hey, Jess!”, one of the guys called to me, “looks like our boy here wants in on the action” he said.

There was a good natured ripple of laughter amongst the group as a couple of them hauled the deputy to his feet. There was an impressive-looking bulge at his crotch.

“Maybe you ought to thank him for his hospitality, like” another voice suggested and other voices murmured their agreement.

I saw the deputy’s eyes widen in shock and fear. I smiled at him, giving him my most dazzling smile.

“Sure”, I said as I dumped my clothes on the bunk and made my way into the other cell.

Naked and cum-covered, I stood in front of the uniformed boy.

Really, he could not have been more than twenty-two or twenty three. He was a good-looking guy in a slightly geeky way, the deputy’s uniform looking out of place on his slim frame. I leaned forward, pressing my chest against him as my hand reached towards his crotch and stroked his bulge. His faced reddened in embarrassment as my fingers lightly brushed along his swollen length.

“My, you’re a big boy” I whispered in the sexiest voice I could manage. “Let’s have a look at what you’ve got to offer me” I said as my fingers drew down his zip.

The deputy began to struggle to get away from me, but as he was being securely held by guys almost twice his build, there was little chance of him succeeding. I knelt down in front of him and quickly unbuckled his belt and pants. I pulled them to his ankles then reached for his boxers. He let out a groan of defeat as I pulled them down and freed his stiff cock.

“Well, look at you!” I exclaimed. “That’s too nice a cock to leave unattended” I said as I looked at seven inches of swollen circumcised manhood. He wasn’t very thick but his slim cock with its exposed smooth head was very inviting.

I ran my fingers along its length from head to his balls. I cupped his balls in my hand and gently squeezed them. The deputy closed his eyes and his body seemed to slump a little when I wrapped my fingers around him and started to slowly rub him. Almost immediately his smooth cock head became wet with pre-cum.

I poked out my tongue and licked away the salty fluid. I felt his cock twitch when he felt my tongue licking him and I smiled wickedly. I was getting the impression that this boy was not very sexually experienced, at least not with oral sex. I was going to educate him big time.

I ran the tip of my tongue around his shiny head then down his length to his sac, before slowly running it back to his head. He groaned around the gag he still wore as I licked him again and again. More per-cum dribbled from him and my tongue greedily licked up every drop of it. My hand fondled his balls, squeezing them together as my tongue circled his cock head over and over. I felt myself becoming aroused again, my pussy beginning to ache as I teased the young boy. I reached between my thighs with my free hand and fingered my hard clitty as I closed my mouth over the deputy’s cock and took him into my mouth.

He groaned again when he felt his length enveloped in the moist velvety warmth of my mouth. I swallowed as much of his length as I could, my tongue lashing his head, my teeth lightly raking along his stiffness as I moved my head up and down. My hand working my pussy moved harder and faster as I brought myself to a quick intense orgasm. I shuddered in pleasure.

As I bobbed my head up and down on the deputy’s cock I reached a hand between his thighs. I slipped a finger between his ass cheeks and quickly found his asshole. When I pressed a finger against the tight ring, he bucked his hips forward, thrusting his cock deeper into my throat. I pressed harder against his ass and he groaned again, thrashing his head from side to side as my probing finger slipped part-way into his body.

I felt his cock swell bigger in my mouth as I finger-fucked his ass and sucked his smooth slim cock, pushing my finger all the way into his tight hole and out again. He was groaning continuously as his unwilling body responded to the pleasure I was giving it. I became aware that there was very little noise from the other guys in the cell as they watched me with the deputy. I felt fifteen pairs of eyes staring at me, which I found erotic in itself.

More pre-cum was dribbling from the deputy’s cock as my mouth licked and sucked him. I thrust my finger harder into his ass and sucked him harder still, my head bobbing quickly up and down on his length. I felt his cock swell and stiffen in my mouth and his body went rigid.

I quickly released him from my mouth and grabbed his cock. I wrapped my fingers around his saliva-slick manhood and began to pump my hand up and down it, my finger pounding his asshole. His face became flushed and beads of sweat popped out along his brow as my hands teased his body towards climax. His chest heaved with rapid pants of breath moments before I felt my finger clamped tightly in his ass and his cock thickened in my fingers.

I pumped him harder and faster and seconds later he cried out as a long stream of thick cum erupted from his cock and splashed over my chest. A second, then a third stream of creamy cum quickly followed as my hand pumped his length. It dribbled warmly down my chest as I drew several smaller spurts deep from his balls. I continued to pump him and finger-fuck his ass until his cock began to lose its rigidity and soften in my hand. I gently eased my finger out of his ass and freed his cock from my hand. I rose to my feet and stood in front of him. I leaned forward and kissed his cheek and mouthed ’thank you’ to him before turning wordlessly and returning to my cell.

The guys freed the deputy and removed the gag. The poor guy looked at me, blushed, and looked away again. He pulled his boxers and pants up and, with as much dignity as he could muster, retrieved his keys and wordlessly locked the guy’s cell door. He told me that there was a shower I could use if I wanted to. I thanked him, collected my clothes and followed him down the corridor. The guys all called after me, commenting on my bare ass as I wiggled it for their benefit. I showered and dressed and found myself released from custody. The deputy assured me that no action would be taken against the gang when they were released in the morning. I gave him my most dazzling sweet smile, kissed his cheek again, and sauntered off to await the cab he’d ordered for me...


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