Jailhouse Coc

About me? Well, I'm the senior training officer charged with updating the skills of the many prison wardens spread across the Eastern states of Australia. I am 6 foot tall, I work out every day so I'm pretty ripped, I have a 9" cock, so I guess you could say I'm popular with the ladies. I'm also serious about discipline and appearance, so my uniform is always right on the money; crisp fitted shirt to show off my pecs and shoulders, always in short sleeves to leave my biceps intimidating to the guys and enticing to the girls. And my views on discipline don't end with work either.

The class filed in to the briefing room. The 'class' was the latest batch of prison guards to come through my training sessions and they were the usual lot, either scruffy or over-primped. Except.........the chick who just walked through the door! At first glance she could almost blend in with the rest, but once I saw her I couldn't take my eyes off her! I don't know whether it was the way she walked, the way she eyed me up and down with those sexy green eyes of hers, or the way she had left the top couple of shirt buttons undone. Mmmm, a hint of cleavage, that's always hot!

She was the last one in and was looking for an empty seat, of which there were several near the back. Luckily there was one right down the front too, and I suggested she take that before she had a chance to spot the other ones. As she sat her tight little arse down in front of me I copped an eyeful of that fantastic cleavage. She wasn't particularly tall, so that just gave me a better view! 'Sweet Jesus, They would have to be double D's at least!' I thought as she took her seat. I love big tits on a small woman. I noticed the name 'Jessie' on her tag (well, it was close to her cleavage!), and all through my session I noticed she was checking out my crotch. Not surprising, since I was always checking her out, and she was making me hard!

The end of the training session arrived and they all started to file out. "Jessie, I would like you to hang back, I have some paperwork for that no-good boss of yours" I said, desperately trying not to smile. Jessie came back to my desk and waited, a glint in her eye, a playful smile on her lips.

"The paperwork isn't here, it's in my office." I lied. I told her to follow me, and we wound our way through the old prison. I took her to a part of the complex that's hardly ever used, except by me. I found a cell that I keep clean, and stocked. Before she could protest, I gently but firmly led her into the cell, closed the door shut behind us, and pulled her to me, kissing her hard. She put her hands on my chest to resist, then softened as she started to enjoy the kiss. I was so ready for her, and I knew she could feel my hardness through our clothes. I took my handcuffs from my belt and quickly pulled her arms behind her back, snapped the cuffs on her wrists, and around the cell bar behind her. Suitably restrained, I could now do as I pleased with her. I stepped back, and took hold of her shirt and ripped it open, buttons scattering, to reveal her ample chest. The delicate lace of her bra was struggling to hold back her breasts, heaving as she panted, obviously wanting more.

I took her in my arms again and kissed her hard, my hands under the remains of her shirt, caressing her back and unclipping her bra with one hand. I pushed her shirt down her arms to her wrists, and pulled her bra up and over her head and down her arms with her shirt. Now topless, I could fully appreciate how good her tits looked. And they were fantastic! Jessie obviously took good care of herself, she had a sexy athletic figure, and these gorgeous full breasts, topped off with beautifully hard nipples! As soon as my hands were on them, squeezing and caressing, I knew they weren't fake. These puppies were real womanly flesh. I played with her tits, feeling the weight of them, their smooth skin, their warmth, their erect nipples so inviting! I leaned down and took one in my mouth and she instantly let out a little moan, her head tilting back slightly. Eagerly I sucked at her breast, biting her hard nub, feeling her body writhe against mine.

"Oh God that's good! But we can't do this here! We'll get caught!" Jessie said breathlessly. I pushed her up against the bars, and thrust my hand between her legs, and felt her heat. I knew she wanted me so! I leaned down, pulled her knees forward and lowered her onto the floor into a kneeling position, with her hands still restrained behind her back. I took my belt off and dropped it onto the hard cell bed, then opened my pants, my hard cock springing out. Her eyes widened as she realised how big I was. They all do that.

"Now you're going so suck it." I told her firmly.

"No, I couldn't fit that it my mouth!" she replied. I wasn't going to take her word for it, so I stepped forward and put my hand under her chin. At first she protested, but as soon as her lips touched my knob, she changed her mind. Like a pro she slid her mouth onto the head of my penis, her saliva lubricating as she went. Her mouth felt awesome on my cock, so warm and soft, and soon she was sucking and licking it like there was no tomorrow! I watched as her mouth moved along the shaft of my dick, taking my whole length in.

"Don't you make me cum in your mouth Jessie! I'm not finished with you yet." I told her. But God, how good it felt! The longer she sucked my meat like that the more I knew I wasn't going to be able to hold back. Then I got to the point of no return and I knew I was going to cum. I grabbed each side of her head and started to fuck her mouth hard, and I could hear hear slurping and slopping as I thrust my cock into her mouth. Closer and closer I got, and I knew she liked it too, as I could feel her starting to moan, and the vibrations from her throat pushed me over the edge. My hips bucked as I came, and my load of hot cum flooded her sweet little mouth and to her credit she swallowed the lot, and there was a plenty of it!

Jessie licked her lips clean afterwards, a look of smug satisfaction on her face. "You shouldn't have done that. Now I'm going to punish you." I told her sternly. I pulled her to her feet and released the cuffs, also removing her shirt and bra from her wrists. I quickly led her over to my desk and bent her over it, re-cuffing her to the bars opposite. I knew she had a great arse, and looking at her bent over like that, the curves of her were so enticing. I ran my hand over her behind, feeling the firmness of her, and I could see a smile creep over her lips.

"This is not for your pleasure Jessie." I said, and slapped her arse sharply, and her beautiful green eyes widened and twinkled. I wasn't going to let her think it's going to be a tickle fest for her. I brought my hand down harder on her arse this time, the material of her pants barely cushioning the blow. 'It's time to turn it up a notch' I thought, and reached around her waist, loosened her belt and pants. Roughly I pulled the waist of her pants down her hips, and past her thighs and her calves, and I noticed at some stage she managed to get her shoes off as well. So there she was, hand cuffed and bent over my desk, her arse barely covered by her skimpy knickers. I might have just cum a short time ago, but things were already stirring again. I unbuttoned my shirt, exposing my washboard abs and pretty serious pecs - all that time in my gym paid off. I could see Jessie turning her head to check me out. Fair enough - I'd been checking her out all afternoon! I gently laid my hand on her smooth, taut rump and she slowly gyrated her hips, thinking it was cuddly time. Quickly raising my hand I brought it down on her bare cheeks with a resounding slap! She flinched, and a little cry escaped her lips before she could stop herself. Again I gently caressed her reddening cheeks, soothing the burn.

"I told you to not let me cum in your mouth Jessie, but you did. Bad girl." Another slap followed. She was ready this time, so the flinch was less, and I noticed she was pushing her arse out to me, inviting more. This time when I touched her bum, I took hold of her knickers and pulled them down so they were level with her butt cheeks. I pulled the waist elastic tightly and let go, letting it snap against her. Pretty tame compared to my hand, but a nice change I thought. I thought she looked hot as fuck there, and so vulnerable. Bent over the old desk, her knickers slightly down. Now I was getting quite hard again and I wanted her. I pulled her knickers off completely and Jessie immediately spread her feet wide, and I saw how smooth and perfect her pussy was. It was then I decided to really tease her. Out of my top drawer I pulled a short riding crop, with the leather snap on the end. First I showed this to her, and that brought a smile to her face, then I slowly caressed her face with it, moving down her neck to her shapely shoulders. At this point I pulled the tie from her hair, and let her long blonde hair fall naturally. I took my seat behind her, and resumed my tour of her body with my crop, I caressed the back of her neck, and followed the contours of her spine, and I admired her stunning physique. Although much shorter than me, she obviously took very good care of herself as she had a sexy, athletic body, the kind you could see in a tiny bikini, tackling the waves on a surfboard.

The leather snap reached the top of her arse cheeks, and then I raised it a little way, and sharply smacked her left cheek. The sound of leather on flesh always turns me on, and this was no exception. This chick had a great derriere, and she was obviously liking what I was doing, the way she would sway her hips just after I slapped her. I did the same on her right cheek, and then I could hear her gently moan each time my crop made contact. A couple more and I decided to cool off for a bit, so I stroked her bare thighs from her knees to her tight pussy. I playfully touched her pussy with the crop, then had a wicked idea. Stroking her labia with the leather, she immediately responded by going with it, moving in time with me. I ran the crop along the length of her smooth slit, then just inside her. She moaned and gently writhed on my desk. The crop slid in further, her lips parting slightly. I knew I had found her clit by the way she jumped slightly, the pleasure sensations taking her a little by surprise. With slow circular movements I massaged her clit, and her breathing became shorter and she pushed her hips towards me with each stroke.

"Oh fuck, Andrew, that feels so good!" Jessie breathed. Faster and faster I fucked her with the crop, and I couldn't take my eyes off her pussy, I wanted her, and wanted her bad! I knew she was getting tantalisingly close to orgasm, and I leaned over and slapped her hard on her arse cheek. That did it, Jessie moaned very loudly as she came, her body jerking with delicious orgasm, made all the more sweet by the fact it was a leather crop rubbing her clit. I backed off my crop, knowing she would be very sensitive now, and I let her cool down again.

I stood up, my rock hard cock eager for her beaver. But I wanted to taste that sweet pussy first. I gently rolled her onto her back, and her entire naked body was before me, still restrained by the cuffs with her arms above her head, but with a big sexy smile on her face. Her pussy was right on the edge of the desk, so I knelt on the floor and for the first time my hand touched the smooth skin of her vagina. Oh man, was she wet! My fingers slid into her so easily, her legs opening wider so I could get deeper. I put 2 fingers inside her and pushed them all the way in, feeling her wetness surrounding them. Withdrawing them again, I couldn't wait any longer, and instantly my tongue was on her labia, tasting her hot pussy. Jessie arched her back as the sensations of incredible pleasure swept through her body. I rolled my tongue around her clit, and her juices tasted so good. She moaned softly now, and gradually I dropped my tongue lower, deeper into her slit. I ran my tongue along the delicate folds of her vagina, back and forward, covering every inch of her pleasure centre. I pushed my face into her pussy, my lips now inside her, and sucked her clit. The more I pushed my tongue into her pussy, the more she writhed and moaned, building her orgasm. Faster and deeper I worked, and louder she moaned, building to a delicious crescendo. I wanted her to cum to much, I love hearing a woman during an intense orgasm. I licked and licked and licked, concentrating my tongue on her clit, pushing, rolling and licking. When I knew she was close, I quickly slid my fingers deep into her dripping pussy, curling them up to stroke her g-spot. Jessie exploded, her orgasm sending her blissfully into orbit, her lithe body shaking with such intense, intimate pleasure, her juices covering my mouth, tongue and chin. And the sweet screams of climax were music to my ears, filling the halls of the old jail cells with feminine ecstasy.

My wanting was overpowering. I just had to have her. I stood up, my cock engorged with blood stood ready too.

"Fuck me hard baby." Jessie breathed, opening her legs wide. That was all I needed. I placed the head of my dick at the entrance to her dripping tunnel of pleasure, and gently ran it along the length of her warm slot, her body twitched as it passed over her still tingling clit. I slid inside her, her hot wetness engulfing my member as her pussy stretched to allow my substantial size in. Jessie caught her breath as she felt me fill her up, pushing all the way in, deep inside her, until my balls were hard up against her butt.

"Oh my God, that feels so good!" She said, throwing her head back. After hesitating a moment to enjoy that feeling of being swallowed by her pussy, I began to fuck Jessie. Slowly at first, pulling out so just the head was still inside her pussy, then ramming it home again, and I could feel her tight pussy constricting me so erotically. Gradually my speed increased, pumping her harder, causing her well rounded tits to bounce upwards towards her neck each time I thrust deep into her. This continued for some time and I could feel myself losing control but I didn't want to cum yet. I stopped fucking her, and pulled out, my cock thickly coated in her feminine juices. I rolled her onto her tummy, and I hated to hide her awesome tits but I wanted to fuck her from behind. And what a great behind it was! I swept my wet cock all over her arse cheeks, down her crack, and finally back into her wet pussy again.

It's funny how fucking the same pussy from various angles feel so different. And hot from any direction! I resumed pounding her again, her cheeks slapping against me every time I thrust into her. I held her hips firmly as I fucked her tight pussy, enjoying the total control I had. I could slow everything down and make love to her real gentle, watching my cock disappear inside her body until I was so very deep, then gradually pull out again, her pussy lips wrapped around my shaft as if trying to keep me inside. I could penetrate her just a little amount, just the head inside her, using small thrusts to pleasure her, then drive it home again, burying myself inside her vagina again. Every time I did this, Jessie would cry out with pleasure, and it felt so good for me too! Thrusting deep into her again, the feeling of my orgasm building was intoxicating, driving me to go faster and harder.

Closer and closer I approached my climax, feeling that sensation growing deep in my loins and spreading throughout my entire body. I held out for as long as I could, knowing that it would make it all the more intense. I moved my hands up to her breasts, cupping both of them, and her exquisite womanly flesh, her hard nipples tipped me over the edge into that wonderful abyss of orgasm and I finally came. That feeling of intense pleasure, my balls contracting ready to explode, then my hips thrusting hard as I shot my load of hot jism deep inside her tight wet pussy. It felt like I was cumming forever as I pumped more and more cum into her. Jessie also climaxed again, and I felt her body convulse as she came, yelling out loudly. As we both rode the waves of orgasm surging through our bodies, we gradually slowed down, trying desperately to keep those sensations going. Eventually though they died away and we stayed there, Jessie still bent over my desk and me bent over her body, both of us covered in sweat, our chests heaving as we caught our breath again. I reached up and released her hand cuffs, so thankful they were so well designed they didn't leave much more than small red marks on her slender wrists.

I helped her to her feet again, and I held her close, feeling her heart beating fast, close to my own racing heart, her head on my chest. We stood there for so long, both totally naked and totally spent. I led her into a nearby bathroom to shower and dress again, and neither of us knew whether this would happen again, but we were glad it happened today.

The End