A Warden's Mistress (Open)

[Lady_Jade666]

A Warden's Mistress (Closed)

Thread Now Closed

Hope Miller had been thrown in prison for twenty years for a crime she honestly never did, she knew that saying she didn't do it looked stupid. A lot of people said that but there was a few that were innocent. She had been in jail for a year while her trial was on going, and it took that time to find her guilty of man slaughter which meant 5 to 7 years in hell. She was terrified she would be hurt mind or body she was printed, photo taken and it was really scary, the CO's were very nice though it was nice to be able to talk to them. They made her laugh a little, but she went silent when they got her to her cell and locked the door behind her, they gave her a bag of clothing, and she changed giving them her street clothing and earings, and a necklace that she hadn't taken off in five years. Once she was alone she sat on her bed and cried, she was scared and hurt.

Hope wasn't the kind of person that opened up her mouth and speak, she was a mouse and that was a nick name for her through school. She was the kind that was easy to intimdate and she hated that part of her. She wanted to be much stronger then that, but in prison it was a different ball game. She fell asleep in her cell crying herself to sleep, and when she was woken up for breakfast she just ignored it. She stayed in her cell for a week without eating, she was in a ball sleeping all the time. And that was the first time she met the warden he was a very handsome man. He came to her with no one with him, sat on her bed and placed a hand on her back while she cried. She had stopped crying and listened to what he had to say, he was a very sweet guy. When she looked at him he was more then good looking, she looked into his dark brown eyes and his shoulder length dark brown hair.

He came to her just about every day and sometimes went to his office. She got to know the man he was, not the warden he was suppose to be. He was kind and sometimes she noticed he was playing with his wedding ring, she figured they were seperated or going through a divorce. Everyday they were seeing each other in the office or at least three time a week. He believed her story that she was innocent and was pulling favors left and right. But the thing was, she was in love with him and he was in love with her. She had no idea what he thought of her but she was in love. She was called to his office one day and when the door closed, he went over to the door and locked it. She swollowed hard unsure what he wanted.

 

[hadruprider]

Danny Jepp was 27 and had been working at the prison for four years. The work was boring and the environment was not very pleasant, but being a women's prison, the job had perks. Most of the women in there were easy and he would often get a blow job in return for cigarettes or whatever else they craved. Some were whores anyway, and they were all criminals. He was young and good-looking and many of the women were happy to put out for him, regardless of how he treated them.

The sexual outlet through his work in the prison made up for the failure of his marriage. They had married too young and now realised it wasn't going to work out. They argued a lot and she hardly ever let him screw her these days. They were going through a divorce, which was a bit painful but was probably for the best in the long run.

One day a new girl arrived at the prison. She was very young and very pretty and different from all the rest in some way. She just didn't seem like a criminal. Yet she was in for manslaughter. She was often in tears, so he would try to comfort her. He wondered if she really was innocent, as she claimed. She would look up at him with her big dark eyes, and he felt that she had a crush on him. His feelings for her were different. He wanted to get to know her intimately but gradually.

After they had got to know each other a little, he started on his plan. He brought Hope around to his office, locked the door behind him and sat down in his chair at his desk, leaving her standing.
"Now then young lady. I don't think you did it, and I can help you get out of here. But I'd like you to do some things for me first. How about taking that top off to start with?"

 

[Lady_Jade666]

Hope was always shy around everyone and that was a major thing when she was around the warden, shy and very mouse like. But he looked past that at least she hoped he did, she never knew what to say around him. What would get her in trouble, what would get her to the shrink. But she didn't care to much, any time away from the general population she felt so much better when away. No one tried anything on her yet, but she didn't know why that was. She was greatful however but was afraid to ask questions. She watched him come in and she cocked her head to the side. Sitting in one of his chairs that was in front of his desk, she watched him it and heard what he said about believing her. And then a twist to the conversation when he asked her to remove her shirt. She had a thing for him, but did he have a thing with her? she didn't know. She knew he had a thing for women since his life was shit in the woman department. She slowly stood up and walked up to him, close enough to touch her if he so desired.

She swollowed and removed her god awful orange prison shirt, it showed a black bra under it. She had a feeling that he would ask for her to remove her bra and she turned around, her backside now showing the warden. She slowly reached her hands back and began to unclip her bra and allowed it to hit the floor, she turned her head looking at him, her hands covering her breasts and her body slowly turned so her naked torso were close enough to him. She bit her lip, blushing heavily. She had never been naked in front of a man before, she was always wanting to be with an older man. She never liked guys her age, she didn't know why exactly but she just did. Now she stood half naked in front of him, wondering if he saw her like the other women of the prison. Or was she something different for him, she heard stories of him fucking different women in the prison. But she knew never to ask or say anything, she maybe in her own personal hell in prison, but she wanted and needed at least one good thing in her life.

"Does this please you?" She asked softly and in a shy manner.

 

[hadruprider]

Danny grinned as Hope started to obey his instructions. The pretty young girl seemed eager to get out of her prison uniform and quickly took her top off as he had ordered. Her skin was soft and smooth and she wore a plain black bra. He would have to get her some nicer underwear.

He was enjoying looking at her, and the sense of power he had over her. He was thinking of what to ask her to do next, when without him asking her, she seemed to read his mind and she started to take her bra off, removing it slowly like a stripper and holding her hands over her breasts before conpletely revealing them to him. She had lovely tits, firm and round, and she stood there right next to him, red-faced, apparently awaiting further instructions and asking if she pleased him.

He thought for a moment. He wanted to fuck her right there over the desk, and he felt that was what she wanted too. But he felt differently about thus girl. Most of the women in the prison were just holes to fuck as far as he was concerned, but this one was so young, so sweet and innocent. He wondered if she was a virgin. He really could not believe that she had committed any crime.

"Yeah, not bad," he said. He grabbed her firmly by the hair and pulled her onto his lap. With his other hand he reached up and gently cupped a breast, feeling its weight and shape, feeling her nipple grow hard in his palm. "Nice tits," he added, bending forward to feel the other one with his lips, pulling her nipple into his mouth and teasing it with his teeth, almost but not quite biting her. Then suddenly he pushed her away from him, giving her a firm spank on her ass.

"You need a nice bra and matching panties," he said. "I'll get them tonight. What size are yiu?" He could guess, but it was better to ask. Then he ordered her out of the office, until tomorrow.

 

[Lady_Jade666]

She watched him seeing how please he was and she was happy, it's hard to imagine what was on his mind. But she heard everything he said and she told him that she was a size Large due to her large bust, she got dressed quickly and left his office. She went right to her cell ignoring everyone, she knew it was better to do that and when it came down to it she was curious as to what he would do. Something in her made her think he really cared about her. But she was sure that he would help her, she had been in prison and god knows how long but she stopped counting the days, it just made it harder. She sighed a little it was hard to imagine what it would be like to just be free, but she knew also she could sue them and she would sue the place for every dime it was worth. The only good thing wa the warden, she stayed in her cell, a CO that liked her brought her mills to her cell and she didn't even bother doing anything but just relax. When she woke up the next day she noticed a box with a bow on it, tilting her head she went to it.

Amy opened it up and noticed what it was, she smiled happily and put it on then put her prison uniform on. This little bit of outside on the inside, she had a book in her hand as she was waiting for when ever he would come to her or ask for her.

 

[hadruprider]

Danny enjoyed going to the women's underwear store. He enjoyed running his fingers over the silky fabrics, knowing that they would soon be up against some woman's tits or pussy. He enjoyed looking at the big posters of beautiful young models, almost naked and pouting suggestively towards him. He enjoyed eyeing up the sales girls and the customers, wondering what they were wearing underneath. He selected a silky, silvery-white bra with lacy edging, in her 36D size, and matching panties. Then he went to the back of the store where they sold other products for women. He bought a bullet for Hope, of the type other women in the prison had begged him to get for them to while away the long hours in their cells - one of them had been his sex slave for a week in return for one of these. He was looking forward to when she ran out of batteries.

He went to the checkout with his purchases, bulging strongly with excitement, wondering if the girl on the counter noticed - her smile suggested she did. He got her to wrap them seperately. Back at the prison he slipped the underwear package into Hope's cell but kept the vibe for later.

Next day he made her wait until mid-afternoon, then took her to his office, locked the door and slumped in his chair, leaving her standing nervously. "Now then young lady," he said, "is there anything you'd like to show me today?"

 

[Lady_Jade666]

She liked what he bought for her and loved wearing it, gave her a small feel of freedom. Though she wasn't the kind of girl to wear it, it was new to her. But she knew how things went of course, she maybe a virgin but she wasn't stupid about the nicer things. She waited for what seemed forever when he came by finally and she went beside him, watching him shut and lock the door she already knew what he was going to ask her, so by the time he asked she was already up and getting ready. When he asked she smiled at him and first she removed her shirt first, allowing her breasts to breath in such a beautiful fabric it was really nice something she felt before. It was nice to enjoy something like this, and then she allowed her pants to fall and she kicked them away and slowly turned around him, showing off her body in what he got her.

"Do you approve?" she asked softly.

 

[hadruprider]

Danny sat back in his chair and looked up at the pretty young girl, looking forward to the show and wondering what she would look like in the sexy underwear he had bought her. He didn't have to wait long, or give her any further instructions. She smiled sweetly at him as she slipped out of her shirt, showing her full young breasts bulging out of the silky bra. Then she wriggled out of her pants, revealing her lovely curvy hips and thighs wrapped up in the matching panties. She turned around showing him her ass and the front and back of her legs,so much finer than the other older women in the prison.
"Yeah, I approve," he said in a deep lustful voice. His cock was throbbing and growing as he ran his eyes over the curves of her hot body. "Turn around again. Give me a twirl. Bend over." He was testing her obedience. She did everything he asked. "I reckon I can get you out of here. I know this hotshot attorney. Told her about your case. She's looking into it. But first - look what you done. That's your fault. What you gonna do about that?"
He grabbed her hand and pulled her close to him, then pushed her down onto her knees, and unzipped, bursting out in front of her, thick and hard and purple.

 

[Lady_Jade666]

She did everything he asked if it meant getting out but she also felt something for him to she didn't know if it was foolish or not, it was hard to say that much she knew. She twirled, bend anything he wanted and then she noticed his pants unzipped seeing what she did to him, then she felt him grab hold and make her hold onto him, she began to stroke him up and down. This made her really horny she was a virgin yes but for some weird reason she wanted him to be her first, so to try to make that happen, she bent down placing his head in her mouth and began to suck just a little and she was careful of her teeth. She went up and down using her teeth only a little, while she was handling him in her mouth her free hand went to her pants, and began to rub her clit under her panties, she was really getting into it. She stopped for a moment and spoike'

"I wish you would fuck me" She said in a shy tone as she went back to giving him a blow job

 

[hadruprider]

Danny smiled with satisfaction as Hope bent down to her task, first holding his cock in her hand, then taking it a little way into her mouth. "Hey, keep your teeth out of the way please! Lips and tongue... yes that's better. You're not very experienced at this, are you? I think you need a lot more practice."

Then she pulled her mouth away and said she wanted to be fucked.
"Did I say you could stop?" He held her head firmly in his hand and pushed her down over him, thrusting up into her mouth at the same time. "Now, how much of it can you get into your mouth? You know Jane, the big woman two cells down from you? She can get the whole lot in her mouth." He pushed in deeper, holding her hair, but she choked and spluttered, so he pulled back slightly so her lips were just working on his sensitive head.
"So you want me to fuck you? What a filthy little slut you are. Well keep begging and doing what I tell you, and when you are really good at cock-sucking I might fuck you."
With the feel of her soft lips on his cock and the feeling of power over her, he knew he was really close.
"Now I'm going to come in your mouth and you are going to swallow every drop." He gave a loud grunt and shuddered with pleasure as he shot his first strong jet over her tongue, holding her hair so she couldn't pull away.

 

[Lady_Jade666]

She couldn't believe she said what she did, she had never been in this situation at all and this was really new to her, she heard what he said and did as he was told, when he was forcing himself into her mouth she was having a hard time with how deep he was going, but it was then that he shivered and then she begn to taste what was being shot into her mouth, tasted salty her first taste of cum, she didn't really try to pull away but it was hard to breath, she looked up into his eyes wanting to be able to breath again, she didn't know what he would do with her now, or what. Did he truly mean she was a slut or just called her that over what she said, because she had no idea about anything sextual. Virgin body and virgin mind when it came down to a lot of different things. It was hard to imagine what he would do with her, then she invisioned having sex with him and she settled down after he did, waiting for him to let go.

 

[Joe_Doe_Stories]

"Don't swallow," Danny said. "I want you to keep it in your mouth, and swish it around, so you get a really good taste. That's it. Swirl it around really good. Can you taste that?"

Bopping her head, Hope nodded.

"That's what submission tastes like. Now I know you probably wouldn't even give me a second look if we were on the outside. But that doesn't matter, convict, because in here that sweet little pussy of yours belongs to me. Do you understand?"

Bopping her head, Hope nodded again.

 

[hadruprider]

Danny gave a contented sigh as the last spasms of his orgasm subsided, and his entire load of cum had been deposited into the mouth of the beautiful young girl kneeling in front of him in her silky underwear.
"Good girl, good girl," he said as he recovered his breath, stroking her head gently, his cock gradually softening in her mouth as she gulped and swallowed. "I hope you.enjoyed that. I certainly did, but you could do better."

He pulled himself out of her mouth and pulled her up, sitting her on his knee, looking into her pretty face with her cum-stained lips. "Now remember what you were told when you arrived. The prison is keen to educate and train inmates, so that they are equipped with the skills they will need when they leave here. So I am prepared to give you regular cock-sucking lessons, every afternoon, so that you can practise and become an expert. Then when you've achieved that I will do as you ask and fuck you."
He slipped a hand down to her silky panties, and felt her slit through the thin material. It was getting quite wet. He enjoyed the tease of making her wait.
"Here's a banana for you to practise on - see how much of it you can get into your mouth. Now get dressed and back to your cell." And he gave her a firm but playful slap on her thighs to send her on her way.

 

[Lady_Jade666]

She listened to him it was interesting to hear what he had to say, being on his knee felt odd but knew in time it would get better, least she hoped. It was really hard to imagine herself doing anything but she took what he gve her and sighed silently she got back in her clothing and tucked the fruit away in her shirt and the guard came back to get her. She went back to her cell and sighed softly. Once the cell doors were shot she went back to her cell not talking to anyone. She read a little bit then began to practice, problem was that the bananna was not as thick as he was but she used her imagination. She was at her desk writing, she loved to write always wanted to be a writer since she had it she thought. She didn't know when she would be called upon, but she was quite saying nothing about it.

 

[hadruprider]

So for the next few days, Danny had Hope in his office every afternoon. He made her strip down to her bra and panties, then kneel in front if him and suck him off. Each time she would manage to get a little bit more cock into her mouth before she started to choke. He taught her where the most sensitive parts were, and how to give him the most pleasure with her lips and tongue. He showed her how to cup and fondle his balls in her hand while she was sucking him, and sometimes he would get her to take him out of her mouth and finish him off by hand, pumping him and milking him with her fist until he came in strong spurts all over her face, his cum dripping down over her tits. Sometimes he would get her to take her bra off, but never her panties - he was saving that pleasure fir later.

After a few days of this training, he gave her the vibe he had bought.
"Now here's another little present for you, Hope. Take it back to your cell and try it out tonight. Then tomorrow afternoon you'll come here and show me how you got on with it, give me a demonstration."

 

[Lady_Jade666]

She did everything he asked her because she was afraid what would happen if she didn't. She took it in her hand and bit her lip, she wanted to make sure she did this right because she was a virgin and this would open her up and she knew what that meant. She would do it she didn't want to see him pissed because she knew his temper was very bad from what she has heard personally and what she was told. She cleared her throat and when he looked at her she was blushing.

"I will do what you have asked of me but you need to know that I am a virgin, I always wanted to loose it to a man not a toy. But if that is what you command I will I just want you to know that, but I will do it" She repeated it so he knew that she would do it. To avoid what happens if she refused it

 

[hadruprider]

He was surprised to hear that she was a virgin and wasn't sure whether to believe her. The way she had asked him to fuck her, quite bluntly, had made him think she had done it with lots of men and was into casual sex. But maybe she was telling the truth. He hoped so. Taking her virginity would make sex with her even more enjoyable. He was also surprised that she didn't seem to know much about sex toys.
"Really? You're a virgin?" He smiled at her. "And you want me to fuck you? You want mine to be the first cock in your pussy? My pleasure!"
He took the vibrator back from her and took it out of its box.
"Now let me explain to you how this works. It's called a bullet vibrator. You don't put it inside your pussy. You turn it on, like this." The little thing started buzzing quietly. He held it to her cheek so that she could feel the vibrations.
"Then you touch your clit with it. Or if that feels too intense, just hold it beside, or close to your clit. You should find, with a bit of practise, that you have a strong orgasm quite quickly. Now do as you are told. Go back to your cell and try it out. Try not to make too much noise! Then tomorrow afternoon you will come here, strip completely for me, open your legs wide so I can check your virgin pussy, then use the vibrator on yourself, so I can watch you come."

 

[Lady_Jade666]

She watched him and didn't know what was going to happen but she heard what he said she was glad that he listened to her, believed her. She was curious about this thing he was showing her. Nodding of course she listened and would obey. She would do it though she didn't want to. That much she knew but she nodded took it, got dressed and went back to her cell. She sat on her bed not wanting to do it but she knew she had to. Once the lights went out she put a clean sock in her mouth and did as he commanded her to do, she really didn't like it but that was all she did for him. Once she was done trying it she went to bed, she didn't want to cum like that she wanted to cum with a man for the first time, but she would deal.

 

[hadruprider]

Danny went home to his wife that night. She was in a foul mood - maybe she suspected he was having sex with women at the prison - and she would hardly even talk to him, so he knew there was no chance of a fuck. So after she had retired to bed he started fantasising about his new virgin slave- girl, Hope, wondering what it was going to feel like when he finally had her, thinking about her masturbating with the vibrator. He jerked off watching a porn video of a girl doing that, but he was still thinking of her when he came.

Next day seemed to drag slowly, until it was time to get her to come into his office. He put on some soft music and reminded her of what he wanted to do. "OK, first you are going to slowly take all your clothes off, like a professional stripper. Then, you are going to open your legs wide for me and show me your tight little virgin pussy. Then, you are going to play with yourself in front of me, using the vibrator on your clit."
He smiled at her and sat back in his chair, looking forward to her performance.

 

[Lady_Jade666]

She was enjoying the simple moring, she had breakfast and instead of going out she just went to her room and read, she took another shower to make sure she was shaven and clean. She got dressed and put the vibrator away on her. Then when the guard came she sighed softly and got up walking with them, she was curious why she wasn't being cuffed but didn't answer and didn't care. When she was set before the warden she just nodded to him and heard the soft music. She stood in the center of the room and closed her eyes, she slowly sway her hips allowing the music to fill her up. She sang softly with it since she sang really well, she opened up her eyes and got in the mood she swayed her his and began to take off her shirt, her back facing him as she bent down showing her orange ass no thanks to the damn pants, she removed her shirt allowing her shirt to come off and hit the ground, she forced herself to face him her arm and hand covering her breasts, and as she moved around she moved right up to him and uncovered her breasts showing them inches from his face.

Then she moved away her back towards him, she bent down and slapped her ass hard enough for him to hear, and grabbed the front of her pants and slid them down showing her panties that he gave her, and slapped her ass again. Stepping out of the pants, and kicking off the shoes she swayed her body and removed the bra letting herself show him and she grinded down onto him

 

[hadruprider]

He sat back and enjoyed the show. She swung her curvy body seductively in time to the music as she slowly started to undress for him. And singing along too, that was nice, she had a lovely soft, sexy voice. After a while she was down to her bra and panties, then the bra came off and she wiggled her tits in front of his face.
"Very good," he said, "have you thought of getting a job doing this? Some guys would pay good money to watch you dancing and taking your clothes off!"
She slapped herself on the ass- did she like that? Was she suggesting that he should give her a thorough hard spanking?
He had seen her go this far before. What he really was looking forward to was seeing her completely naked. Did she have a bush or was she shaved? What sort of pussy lips did she have? And what would she look like masturbating with the vibrator?

 

[Lady_Jade666]

She smiled at him, doing what ever was needed and she went to his ear and licked it, gently nibbling on and then let go. She removed her bra and very slowly removed her panties, she showed a clean shaven pussy and she grabbed the vibrator that was on the floor. " How would you like me sir?" She asked him bowing her head in respect since the music was over. She was ready to do what ever she had to. Then remembered what he wanted, and it was easy to tell she remembered. She had just gotten so into the moment, she hummed as she laid beside him on a couch that he had in there. One leg over the back of it, the other almost off the couch but enough to show her perfect hairless pussy.

 

[hadruprider]

His cock swelled and hardened as he watched her slowly wriggling out of the sexy panties he had got her, showing him her beautiful smooth mound and neat little pussy lips.
"Good girl," he said, "what a pretty little pussy you have."
As she lay down naked on the couch and opened her legs, he got so hard that he had to unzip his pants and allow his huge throbbing erection to burst out.
"Now, spread your legs really wide for me. And open up those pussy lips with your fingers, do I can get a really good look at you and check that you really are a virgin."
He moved closer to her an looked up between her thighs. Yes, he could see her thin, taut hymen and just a tiny little hole. "Very nice. I'm going to enjoy that later. But first, let's see you play with that vibe."
He slowly stroked his cock as he watched her bring the toy closer and closer to her clit, which was still small and tucked away. He wanted her pink and swollen and soaking wet before he would fuck her.

 

[Lady_Jade666]

He seemed pleased she as getting use to following his orders, she looked at him and took it in her hand. She swollowed hard and rested her head back and looked up at the ceiling and softly sighed a little bit, then she began to slowly put the vibrator against her clit, she bit her lip trying not to moan, she felt dirty doing this. She never saw the point of them, she wanted a real dick. And she knew that was coming, softly her eyes closed as she moaned loudly her clit swelling up becoming more and more like a bright pink. She felt herself getting wet, was kinda hard not to feel it since the couch was getting wet to.

 

[hadruprider]

He really enjoyed watching a girl masturbate. The sight of her body writhing, her genitals swelling and reddening, the moisture oozing from her pussy, the sounds, gasping, moaning, and the aroma as her juices started to flow.
He could see that Hope was getting close to orgasm, as her breathing got heavier and she started to thrash around a bit, throwing her head back, the muscles in her legs quivering.

"OK, now stop!" he ordered, snatching away the vibrator and turning it off, leaving her quivering on the brink of orgasm. "Now, I'm going to fuck you. You're going to lose your virginity. That's what you want, isn't it."
He stood over her by the couch, and gradually unbuttoned his shirt and slipped it off. Then he undid his belt and dropped his pants, and finally his boxer shorts came off, revealing his thick, fully erect cock. He knelt down between her open legs and leaned forward over her, giving her a little kiss. The tip of his cock brushed against her thigh, and he moved his hips skillfully until it nestled in her wet slit, brushing up and down until it was coated in her lube.
"So, are you ready for it?"