Cheryl’s Probation

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“Cheryl, you’ve got to stop getting into trouble. This is probably the last time I’m going to be able to get you out. If you screw up again you go to prison. Do you understand?” He looked across the interview table at his client. She was under arrest for a violation of her probation, for the second time. She was 43, about 5’6″ and 150 pounds. She was fairly attractive, with long brown hair, even though she had a belly on her.

“I know. I promise I won’t screw up anymore. I’ll do whatever they tell me to do.” Cheryl honestly knew that she was at the door of going to prison. She’d really tried to do what she was supposed to do, but when her ex-boyfriend had come over on her birthday with the coke, she just couldn’t refuse.

She hated to disappoint her attorney, because he’d tried awfully hard for her and really seemed to care about her. It was too bad she never seemed to get a man like him, she always ended up with bums. Bums who did nothing but get her in trouble. Like her ex. She’d been doing so good, nearly seven months of clean time. But she was lonely too, the only people she met were those in her rehab program, and they were just as afraid of her as she was of them.

When she got arrested this time she’d called her attorney and he’d come to see her before he was even re-appointed. She’d told him what had happened and begged him to try to get her out of jail. He’d listened and then chewed her ass about screwing up. But she knew she deserved it. She could tell he was a little attracted to her, because he always treated her so nice. She’d had other attorneys, and they just treated her like a piece of meat. He was married, but she knew he wasn’t totally married, because she saw him occasionally glance down the front of her jail top. It was a little too big, and she hadn’t been wearing a bra when she was arrested, so she still didn’t have one. She had a tattoo just above her left breast, and when she leaned forward the shirt billowed out to where the tattoo was clearly visible. She liked leaning forward, every so often, and although he never directly stared down her shirt, she could see his gaze wander there periodically.

After leaving the jail, he filed the motion for bond reduction, then made some calls before heading home. That night in the shower his thoughts wandered to Cheryl. He liked her voice, which was a little like baby talk. However, she was no baby, he thought. He thought of her tattoo, and tried to imagine what her tits looked like. If only she’d stay out of trouble he thought. She just needs to have somebody to keep an eye on her and tell her what to do. But as he thought this, his hand rubbed his erect penis, soaping it down good as he imagined various scenarios where he was telling Cheryl what to do. Soon he heard his wife, the blood left his cock, and he again went to bed frustrated.

* * *

“Hi. I made bond! Thank you, oh thank you. You don’t know how happy I am to be out of there. You said to call you when I got out, so here I am.” Cheryl was very excited to be out of jail. He’d gotten her bond reduced to an O.R. and she’d gotten out after only a couple of days. It took them until after 5 pm to book her out, but she called like he’d told her to, and she was a little surprised to find him still at work.

“Congratulations. Where are you?” He asked. He was alone in the office, everyone else having left about half an hour earlier. Normally he’d have been gone too, but he thought she’d make bond tonight, so he’d waited to see if she’d call. Besides it was a Friday, and his wife had taken their daughter to visit the in-laws two hours away. He had nothing else to do.

“I’m just right down at the corner. I guess I’ll go try to see if my sister will let me stay with her tonight.” Cheryl wanted to get into a hot tub, and some clean clothes. They’d given her back the same clothes she’d been arrested in a week ago.

“I want you to stop by and see me, okay?” He tried to put a little authority in his request.

“Okay. But isn’t your office closed? How will I get in?”

“I’ll look for you at the door. Come to the front.” He walked out of his office, down the hall to the conference room where he could see the street out front. His cock started to harden at the prospect of having Cheryl here alone. Kayseri Escort There wasn’t anything wrong about meeting with a client, alone, after hours. But he wasn’t thinking about work this night, and the wicked thoughts he was having excited him. In a couple of minutes he saw her approaching down the sidewalk. He unlocked the door for her, and held it open so she had to brush against him to get in. Once inside he followed her back to his office in the corner. He was pleased she remembered the way.

“Lets talk in the conference room down the hall Cheryl,” he directed her. He guided her not to the big room they used for clients, but to the small private room that the attorneys used for brainstorming, and informal meetings. Inside the small room were a couple of couches and a desk. He sat on one of the couches and saw that she immediately took the other one.

“How are you doing?” He asked. He was taking in the outfit Cheryl had on. He’d only seen her in something besides jail clothing once before. She was wearing jeans and a loose fitting white blouse. Unfortunately the blouse concealed more than the jail top did, and he was disappointed. “Do you think you’re going to be able to stay out of trouble this time? Because if you commit the slightest violation while on bond they’ll throw you back in jail, and we’ll have no chance at re-instatement at the hearing.”

“I know. I’m going to do what ever they tell me to. I sure don’t want to go back to jail, or to prison.”

“Are you sure you can do that? It won’t be easy.”

“I know, but I can do it. No matter what, I’m just going to keep my mouth shut and do what I’m told.” Cheryl answered.

“Really?! Let’s just see, okay? I’m going to give you a test to see if you really can make it. I want you to do exactly what I say, without any whining, or protest. You willing to give it a try?” He felt like he ought to give her an out, before he started something that could have serious repercussions for both of them.

“Yeah, sure.” She said. She had a pretty good idea what he had in mind, and she was rather anxious to find out how far he’d go. Not as far as she would, she’d bet.

“Okay, first I want you to stand up. Okay. Now, turn and face me. I want you to look at me the whole time, unless I tell you not to, Okay?”

“Yes.” She said, rather quietly. She was getting a little excited herself. Her lousy ex-boyfriend had fucked her the night he brought over the coke, but he’d been lousy. And while the opportunity was there in the jail with a couple of the women, Cheryl wasn’t really in to that. She’d gotten to finger herself a little in the cell, but not near enough to do any good. It had just whetted her appetite.

” Close the door. Good. Now lock it. Come back over here where you were. I want you to turn around, with your back to me. Now bend over and slip your shoes & socks off. You know, I like your ass Cheryl. It’s a nice womanly ass, not like a boys at all. Do you like your ass?”

“It’s okay I guess” She answered. She was bent over removing her socks. Just for the thrill of it she wiggled her ass at him a little. If he likes this ass I ‘ll just show it off a little, she thought.

“Now, stand back up. Are you wearing a bra?” He’d remembered that she’d not been wearing one in jail.

“No, I didn’t have one, and they don’t give you anything like that.”

“Turn around. You know I’ve seen a little of your tattoo, don’t you?”


“What’s the tattoo a picture of? I’ve not been able to get a very good look at it.”

“It’s a bouquet of roses,” she replied.

“I want to see it. Take your top off. Now.” He sat there mesmerized as she did as he told her. His cock was straining hard against his slacks, he was very excited. “Oh, I like your tits too Cheryl. That tattoo is pretty, but those big pink areola’s around those nipples are fantastic. Did you breast feed your children?”

“Yes, but that’s been almost 15 years ago now. Nobody hardly sucks on them anymore.” She had feeling that was about to change.

“That’s a waste.” He said. “They’re pretty good sized, and you got some sag from the years. Can’t you get them into your own mouth?”

This surprised Cheryl a little. She’d been looking down at her nipples Kayseri Escort Bayan with him, but looked up sharply at his question. “I don’t know. I’ve never tried.”

“Put your fingers in your mouth and wet them.” He said. “Now rub the saliva on your nipple. Get it nice and slick, do it a couple more times until they’re both nice & wet. There you go. How does that feel? Do you like it?”

“It feels nice.” She answered.

“Bend your head down, and lift the nipple into your mouth. See it fits! I thought it would. Now, I want you to suck on the one while you pinch the other between your fingers. C’mon! Suck hard! Pretend your trying to get milk out of that big boy. Okay, now switch. We need to keep them both nice and wet. Feels good, right?” He could see that she was enjoying this, even if she was fighting it a little.

“Mmmmmmm” She moaned as she was sucking on her own tit. I don’t know why I didn’t do this before, she thought. Of course, it’s a lot better with him here telling me to do it.

“Okay, stop.” He was surprised she did it so quickly. “Drop your pants. I thought so. No panties either, very nice. You don’t have a lot of hair on your pussy Cheryl, how come?”

“I like to keep it trimmed.”

“I like it that way too. Is it wet? Show me.”

Cheryl was a little embarrassed, but she did what he said. She slipped her finger into her cunt and, although she knew she was excited, she was surprised to feel just how wet she was. “Oooh! It’s really wet.” She pulled her finger out and held it where he could see.

“It sure is. Taste it. Tell me how it tastes.”

Again Cheryl found herself a little shocked by his command. Maybe he’s kinkier than I thought, she thought to herself. I’ve never tasted myself either. Oh well, it can’t be any worse than the times I tasted those other women on my boyfriends dick when he’d come home from partying & make me give him head. She slowly brought her hand up to her mouth and sucked her finger into her mouth. It was the same tangy taste she remembered from her boyfriend. But this was more exciting. This was her. And it was warm, and still wet, and she found herself greedily sucking all her juices off her finger. “That’s kinda good” She told him. “I’ve never done that before either.”

“What else hadn’t you done?” He asked.

“Well, I never sucked my own tit before. And I sure never did this kinda stuff in front of somebody else either.”

“But you’ve done it while alone?”

“Some stuff. I felt my pussy before.”

“Did you masturbate yourself?”


“When you were in jail?”

“A little. There’s no real privacy there. I ain’t had much beside myself for the last year or so.” Cheryl was surprised she was telling him this, but somehow, given the current situation, she felt like she had to answer whatever he asked.

“Do you make your self come, Cheryl?”


“How do you do it?”

“Different ways. I like to do it in the shower, but I usually can’t come that way. At night, when I go to bed, I sometimes make myself come.”

“Do you use just your hands, or have you used other things?”

“Usually just my hands, but I have tried other things.”

“Like what? Tell me.”

“Well, I borrowed a dildo from a girlfriend once. It was real big, and colored black. It was shaped like the real thing, but it was so big it was uncomfortable. All I could do was just move it in and out. I like to work it all over, that’s when I can come the best. I’ve used a bar of soap, a hair brush handle, a shampoo bottle, I guess I mainly use something else in the shower.”

“I want you to lay down on the couch, right there. Here’s a pillow, prop your head up on the arm there. Now spread your legs. Nice, I like your tummy. I want to watch you play with yourself, I want you to make yourself come. I’m just going to stand down here at the end of the couch and watch you, okay?”

“Okay.” Cheryl laid down and spread her legs wide. She put her feet together in the middle, with her knees bent, and opened herself up. She saw him looking at her, and it was weird to her, but she liked it. She started running her finger down through her cunt like she liked it. She slipped the finger inside herself, Escort Kayseri getting it nice and wet, and pulling the wetness out to spread over her clit and labia lips. She had nice big lips, she knew, and when she got excited they puffed out and got real sensitive.

“I’m going to pull out my dick, okay? Right now I’m just going to stay here and watch you. I want to see what you look like when you come. Can you come for me? Do you think you can do that?” He had his pants down around his knees and was releasing his throbbing cock from his briefs. He was staring at Cheryl rubbing her own pussy. She looked so sexy.

“Okay. Yeah. I can do it. It feels so good. I really like rubbing myself, I actually do it all the time. Almost everyday. Can I taste it too? Would that be alright?”

“Sure, that’s okay. Tell me whatever’s going through your head. I want to know.”

Cheryl put her other hand down there and got the fingers on it wet, then she brought that hand to her mouth while continuing to rub herself with the other. “I like the taste. I liked sucking my own tit too. Can I do that again too?”

“Sure Cheryl, do it.”

After getting all the juices off her fingers she reached down and pulled a breast to her mouth. She leaned down as far as she could and took the nipple into her mouth, and sucked it as hard as she could.

“Have you ever had sex with another woman?” He was excited to see how much she liked the taste of herself.

She stopped sucking to answer him “No. I have tasted other women on my old boyfriend though. I never liked it at the time. One woman in the pod tried to get me once, but I was too afraid to say yes.”

“What did she do?”

“She just came up to me one day and said she wanted to eat me out. She said I’d really like it.”

“Do you wish you’d let her?”

“No. She was a nasty bitch, and I wouldn’t want to do it in the jail. But I might try it under other circumstances, with somebody else.”

“How are you doing? Are you getting close?”

“Some. It feels real good. I like to push my finger in as far as I can sometimes. Watch. Can I suck my tit some more, I really like that?”

“Sure.” He watched as she sucked her tit back into her mouth, and he could hear her sucking sounds. Her long finger was sliding all the way into her now, and she was rubbing her clit with her thumb. He was getting pretty near himself, but he sure didn’t want to come before she did, if even then. He was thinking how good it would feel to push his swollen cock into her pussy and fuck her. But for now he was just going to watch. He’d probably ought to get a rubber if he was going to fuck her. He’d had a vasectomy several years before, so there was no danger of pregnancy, but who knew who else had been fucking her. He sure didn’t want to get any sort of disease.

Cheryl built to a frenzy and she knew she was about to come. She stopped sucking her tit, and threw her head back. She concentrated on quick rubs on her clit, which was almost hard from excitement. Then the waves of orgasm swept over her. She felt the contractions begin, and her juices start to flow even more. Then she was there, and she cried out in pleasure. She lost all thought of him, last seen stroking the hell out of a decent sized cock. “AHHHHhhhhhhhhhh!” She cried out.

Just as the spasms started to subside she heard him groan and felt his warm semen squirting onto her legs. She opened her eyes, and saw him standing there, his cock just finishing it’s pumping, a glazed look on his face. ” Can I clean that off for you?” She asked.

“I insist. But gently, I think I was a little rough on it.”

She raised up and sucked the shrinking head of his cock into her mouth. She had always liked the salty taste of a man’s come, and his was no exception. After a minute or two, he was done. She let the cock slip from her mouth, and asked “Do you want me to keep going? I’m sure I can get it hard pretty quick?”

“I appreciate the offer Cheryl, but no. There’ll be other times for that. I want you to get dressed and go find a place to stay. I’ll call you tomorrow.” He slowly pushed his drained penis back into his boxers and pulled up his pants. He helped Cheryl with her clothes and walked her to the front door.

As she stepped outside, she turned and pulled hie head to her, where she kissed him, hard, on the mouth. “I did good, didn’t I?” She asked.

“So far, Cheryl. So far. I’m not done testing you yet.”

“You better not be.” She said with a big, mischievous, smile, and then she walked on down the street.

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