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Chapter 16
by DamianWhite
Onward to your cell block. Or does something else happen?
To the cell block
You make it to the cell block without anything untoward happening. As always, "Grandma" is there at the station. You go over notes from the last couple of shifts. Apparently Doe was actually better behaved than normal, although "Grandma" still referred to her as "the bitch". Then she is gone, and you are in charge of the cell block for the next eight hours.
You start by pouring yourself a cup of coffee, as you always do first thing upon the start of your shift. You can tell that the coffee is pretty severely depleted in the thermos, due to Derek's actions, and the space the packet is taking up. You bide your time, drinking your coffee and going
through the ubiquitous paperwork. When your cup is finally empty, you pour yourself another, and let the last of it trickle into your cup, just barely topping it off. Then, conscious that your body is blocking the camera, you give the thermos a solid shake, dislodging the packet, which you are then able to carefully pull out through the top of the thermos.
You clean it off carefully with a kleenex, then slip it into your chest pocket. You continue sipping at your coffee for a while. You want to rush to Doe's cell so badly, but that would be suspicious. So you nurse the cup for a while, then begin your rounds, arranging things so that your favorite little prisoner is your last stop.
It actually takes you about an hour to check on the few other prisoners, and tend to their needs, but finally you find yourself standing in front of her cell. Doe is sitting on her bed, watching you as you slowly unlock the door and enter her cell. She smiles at you hopefully.
You want to say that you missed her, and couldn't wait to see her again. That you love her, and want to feel her in your arms again. But deep down, you know what she most wants to hear at the moment.
"I have it," you say simply, walking further into the cell. With a little squeal of pleasure, Doe bounces up from the small prison bed, and meets you halfway. You pull the packet out of your pocket, and have just barely started to hold it out to her when you feel her mouth on top of yours, even as her hand closes over the packet, her tongue prying open your lips as her fingers wiggle their way into your hand, unwrapping it from the packet. After almost a minute, she finally breaks the kiss, backing away from you, the packet held gingerly in her hands.
"I wasn't sure if you were going to go through with it," she smiles. "But I'm really glad you did. And since you kept up your part of the bargain, I will too..." She moves up to you again, kissing you lightly on the lips. "Give me a few minutes to get ready." She smiles demurely. "Oh, and do you have something that will help us... well, you know. I've never done this before, so I will probably be really tight."
"Yeah, I can get something," you reply, thinking of the gel you keep available for cavity searches. That is, in effect, what you will be doing anyway. You should have brought some anyway, but you know that Doe would have needed some alone time anyway. You let yourself out of the cell, and head to the supply closet, recovering a tube of the gel. It's only a few minutes until you return to the cell, but Doe is already stretched out naked on the bed, her clothes neatly folded on the desk, and the packet nowhere in site, even though you know that she has already opened it.
"I've been waiting for you," Doe giggles playfully, twisting sexily on her bed. Her voice has already taken on an etherealness to it, but also a little bit of hyper-ness. But if anything, they are just slight exaggerations of her normal state.
"Why are you not naked yet, John," she pouts, and climbs off the bed. That is a good question, you think, and assist her as she starts undressing you. You actually have to slow her down, to keep her from tearing buttons off of your shirt. She notices the tube in your pocket, and pulls it out. Glancing at it quickly, she giggles and puts it on top of her clothes on the desk, then pulls your shirt off and helps you with your pants.
As your pants slide down, she kneels down then, and pulls your underwear down as well. Not surprisingly, your cock has been erect for some time now, and she grabs it softly with one hand, eying it with mock seriousness.
"Now, how are we going to get this big thing into my teeny-tiny ass," she muses to herself, then giggles again. She starts stroking it gently, then pops the head into her mouth. You see her free hands slide down between her legs, and as she sucks on your cock, she begins rubbing her clitoris. As her expert mouth works on your aching cock, she starts sliding a finger into herself, giving herself at least as much pleasure as she is giving you at the moment.
She doesn't even try to pull you out of her mouth this time before you cum; instead, she just swallows it all as you cum, not letting any of it out. Doe takes your cock out of her mouth, licking the tip to make sure nothing is lost, then pulls her finger out of her pussy and sucks on that, looking up at you as she stands up slowly, still holding on to your cock.
"I know you aren't finished yet, loverboy," Doe murmurs, her hand squeezing your cock. And she's right. Even after the mind-shatteringly good blowjob, first and foremost in your mind is what is about to come next, and it is enough to keep you hard.
Doe leads you over to the bed via her hand on your cock. She picks up the tube of gel from it's place on her desk, then pulls a pillow off of her bed, and sits it down on the floor by the side of the bed. Turning around, she kneels down on it, then slowly leans down over the bed, resting on her elbows. She looks back at you, looking a little nervous now.
You kneel down behind her, not minding the hard floor on your knees. You unscrew the top off of the tube, squirting a generous amount of the gel onto your hand. It's cold, so you rub it between your fingers until it warms up, then slowly bring your oily fingers to Doe's bottom, and run them up and down her crack, letting the gel cover her skin, your fingers just brushing over her backdoor for now. But your movements get more targeted, until you are rubbing the gel directly on Doe's asshole now. Gathering a glob of the gel on your middle finger, you gently work that finger into her, causing Doe to moan softly. You carefully work that finger in and out of her, twisting it around to evenly distribute the lubricant.
You set the tube back on Doe's clothes, then pull your finger out of her ass. She is very tight back there, and you are wondering are this will work out, even with the gel. Although thanks to the "present" you snuck in for her, her pain tolerance is almost certainly heightened at the moment. You move closer to her, and place the tip of your cock up against her little puckered hole. She looks back at you, biting her lower lip softly.
"Slowly," she whispers softly as you start to press against her. Although your finger went into her with relative ease, your cock is a good bit bigger, and Doe was apparently telling the truth when she said you would be her first one to take her ass. You keep pushing harder and harder, trying to get into her, but you are afraid of hurting her, even though you want nothing more than to plunge your dick deep into her ass.
"It's okay," Doe says softly. "I want you in me. I don't care if it hurts." Simultaneously reassured and even more concerned about inflicting pain on her, you still find yourself applying more ****, until suddenly you feel her ass suddenly give a little, and then with a sharp intake of air from Doe, the head of your cock slips in past her anus, squeezing hard against your cock.
"More," she begs, although there is a trace of pain in her voice. You oblige by pushing in a little deeper, making her body tremble against you. You pull back out a little, letting the gel you rubbed onto and into her ass cover your cock a little more before you slide it oh so slowly back in, letting it sink in to the hilt, drawing a loud moan from Doe and a incredible feeling of pleasure for you.
"Oh God," Doe moans as you slowly begin fucking her bottom. "I never thought I'd let anyone fuck me in the ass..." She reaches behind herself, feeling your cock as it moves in and out of her firm rear, to reassure herself that it was really happening.
"Does it hurt?" You know that it does, but still feel obliged to ask.
She looks back at you over one shoulder, her face half hidden by her hair, smiling gently. "Not as bad as it did at first. It's starting to feel good at the same time, too." She starts pushing herself back against you, meeting your thrusts. Timidly at first, but as the pain subsides, with more confidence. "And it will go even better next time you do it," she says mischievously, knowing the effect the suggestion that this could become a regular thing will have on you.
Both of your movements increase in **** and speed, and if she is still feeling any pain, she gives no sign of it. She is pushing herself back onto your cock just as much as you are thrusting it into her, and her body seems hungry for what you are giving it. Deep, throaty moans come escape from her mouth, in time with your deepest penetration into her, and her sweat and and the juices from her pussy mingle now with the gel you used on her earlier. She is looser around you now, although still incredibly tight, and she is far more lubricated as well. You don't know if you can say that this is definitely better then her pussy; it's certainly different, but you don't think you'd ever get tired of either.
"I'm going to cum," Doe moans loudly. "I want you to cum in my ass, John. I want you to fill my ass with your cum, so that I know I've been fucked there good and hard..." Her voice rises at the end, changing into a muffled scream as she crams her first into her mouth, and you feel her ass squeeze so tightly around your cock as she cums that you barely have time to bury it into her one last time before you start cumming yourself, and fulfill Doe's request that you fill her bowels with your cum. And you can't stop cumming, it seems like, even after cumming before when she sucked you off. You can feel it oozing out of her ass, around your cock, and running down her pussy and legs.
"Take it out slowly," Doe murmurs when both of you finally feel the last vestiges of orgasm gently fade away. "I want to keep your seed inside of me for as long as I can." You oblige, sliding your cock out slowly as she squeezes her anus around it tightly on the way out, letting only a trace of your semen spill out as you do so. She straightens up slowly when you are out, nestling her body back against you. You put your arms around her, crossing them over her chests and cupping her breasts from behind. Her nipples are still hard, and she brings her hands up to cover your hands. She turns her head to the side, and you oblige by leaning around her to kiss her firmly on the mouth.
"Stay with me a while, John," Doe begs. "It's so lonely once you're gone."
Do you risk staying with her longer, or do you head back to work before someone gets suspicious?
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The starlet and the prison guard
A hollywood starlet is sent to your jail, and may be ready to bargain for some special treatment.
Created on Jul 8, 2010 by DamianWhite
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