Cheryl's Probation

His adventure with Cheryl was constantly on his mind for the next few days. The one time his wife was receptive to sex, all he thought about Cheryl, and how she had looked spread out in front of him. He knew he had to do it again, and various scenarios ran through his head as he tried to determine just what he could, and should, do.

All he had for Cheryl was a message phone number with her mother. Her mother was a nice woman, but she had lots of her own personal problems, and had taken on the added headaches of taking care of Cheryl's kids. Actually Cheryl's son was 20 years old now, and was living on his own. Her daughter had gotten into trouble with the law and had been shipped off to a juvenile work farm up north.

He called her mom and left a message for Cheryl to call me. Cheryl called back, just before 5 pm and said, "I wondered when you were going to call. I've been waiting."

"Are you doing everything you're supposed to?" He asked.

"Oh, yeah. My sister is letting me stay with her for a bit, but I've got to find my own place. They won't let me go back to my old house."

"Who won't?"

"My probation officer. They say it's in too bad an area, and that I'd just get back into trouble there."

"They're probably right. Somebody would show up with your door, and there you'd go again."

"No way! I'm not going back into that jail. I'm gonna do whatever they say."

"Is that right? I think I may need to test you on that a bit more. What do you think about that?"

"Yeah, okay. Do you want me to come by your office?"

"Where are you Cheryl?"

"I'm at my sister's. She's gone out for a while, so I'm using her phone."

"What are you wearing?"

"Just some jeans and a T-shirt." Cheryl looked down at herself and thought she wasn't dressed very well. He probably liked women who dressed up real fancy.

"Are you wearing a bra?"

"No, not right now. If I'm going to go out I ought to put one on though."

"How about panties?"

"Well, yeah."

"Does your sister have clothes there?"

"Yeah, she has lot's of nice stuff."

"I want you go get some of her clothes. This is what I want you to wear, okay? This is part of the test. Your sister won't mind if you wear some of her clothes will she?"

"Probably not. But she's smaller than I am."

"I want you to take off everything you've got on. I want you to take a quick shower, clean yourself real good, all over. Then I want you to wear a nice loose, short skirt, and a short sleeve blouse, white if you can. No bra, and no panties. Maybe just some sandals too. Think you can do that?"

"Yeah, I know just what she has that'll work too."

"Are you horny Cheryl? I want you to suck on your tits as you shower, but don't touch your pussy other than cleaning it. Don't touch it until I tell you to. Do you understand?"

"Uh huh." Cheryl's hand had already dropped to the outside on the crotch of her jeans. She wanted very much to rub her pussy, but she'd wait like he told her.

"When you're clean and dressed, call a taxi and have it take you to the Drop Inn Hotel down on south Broadway. I'll be waiting there for you."

"I don't have no money for a taxi." Cheryl replied.

"Don't worry. I'll take care of that. I'm giving you 45 minutes. No touching that pussy now."

Cheryl quickly ran to her sister's closet and started rifling through her clothes. She had a tan pleated skirt that Cheryl was pretty sure would fit. It went about down to her sister's knees, but on Cheryl it would be several inches above that. She also found a blouse, but it was going to be a tight fit. Maybe that's even better she thought. She stripped out of her clothes and jumped in the shower. It was a terrible frustration not to be able to slip her finger into her pussy and rub it like she always did in the shower. Ever since that last time with him, when she'd discovered the taste of her own tits, Cheryl enjoyed taking her nipples into her mouth and sucking hard. She liked the way it felt on her tits, and she really enjoyed the way her nipples got so hard in her mouth, and the whole area around the nipple seemed to get super sensitive.

Cheryl was glad she had trimmed her pubic hairs only a couple of days before. She knew if she had to do it now, she'd never be able to keep her hands of her swollen clit. But she did cheat a little. He'd told her to wash herself, and he'd said she could wash her pussy, so she decided not to use the wash cloth and just use her hands. She soaped up her hands with the bar and rubbed the soap into her pussy, getting it nice and clean. Being careful not to do too much, she carefully washed her clit too. Then she reached down and soaped around her asshole, sliding a finger inside to make sure it got good and clean.

She had no idea what he had in mind, but she wanted to be as clean as she could for him. If the last time was any indication, he was a lot kinkier than she'd imagined. No, there was no idea what he might want. Despite the fact she'd cleaned herself well, her pussy just flowed with anticipation and she could smell it's musky odor as she toweled. She sucked her nipples one last time, and slipped on her sister's clothes. The skirt fit well, and she could feel the fresh air on her crotch as she moved. The blouse was tight, pulling against her breasts. She looked in the mirror and she could see her dark nipples, and her tattoo, clearly through the white blouse.

She brushed her hair, and teeth, and put on some makeup. Not much, but at 42 she needed a little help. She then called a cab and took off for the hotel. The driver was a greasy looking foreign guy, who didn't talk to her at all. For that she was thankful, because she felt like she was dressed like a hooker.

When she got to the hotel she saw him step out of a room about midway down. He approached the cab, and she told the driver that he was going to pay.

"How much is the fare?" He asked.

"$13.50" Said the driver.

"Do you see this lady you've been driving? Isn't she pretty?"

"Yeah, sure." The driver replied, not really looking at Cheryl.

"How about if she gives you a blow job for the fare? Sound good?"

Cheryl was shocked. Did he really think she'd give a blowjob to some stranger? Was this part of the test? If it was and she refused, then what? She had told him she'd do anything, and now here she was saying no. But she never thought she'd have to things with somebody else, she just thought she'd do things with him.

"You'll be glad to suck the man's dick for the fare, won't you Cheryl?" He looked challengingly at Cheryl, and she knew this was part of his "test".

"Yeah", she answered, rather quietly.

At his urging the cabbie opened the door and turned to put his feet outside the cab. Cheryl looked at him then turned toward the cabbie thinking I don't know why he had me get all cleaned up to touch this dirty guy. But she dropped to her knees in front of the man and reached out to undue his fly. She had unzipped the man's pants and reached in to pull his penis out, just starting to move her head down towards it, when she heard him speak.

"Nah, I've changed my mind. Come on Cheryl." He threw a $20 bill at the cabbie and pulled Cheryl to her feet. He led her into the room, and closed the door behind them. "I just wanted to see if you'd do it." He said.

"I thought it was part of your test, I didn't want to." Cheryl said.

"I know. Get on the bed okay. Scoot on up, lean against the pillows. That blouse is tight isn't it? Undo the buttons. Yeah. Open it up, I want to see your tattoo. Those tits look good too Cheryl. Do you still suck them yourself?"

"God, all the time. I wish I'd have figured it out a long time ago."

"Go ahead, suck them. I like watching you do yourself." Cheryl pulled her tit into her mouth and found that the nipple was already stiff. She reached down and rolled the other nipple between her finger with one hand. Cheryl kept this up for a few minutes, but the overpowering urge to rub her pussy forced her to stop.

"Can I rub my pussy?" She asked. That was what he'd had her do the last time.

"Not with your hand.". He replied. "I picked up a present for you." He reached into a bag behind him on the dresser and brought out a big neon green dildo. "Have you ever used one of these Cheryl?" He asked.

"No." She answered. The thing looked bigger than a real cock, and she started to wonder how it would feel up inside her. She'd seen a couple of porno films in her time where she'd seen the women put those inside themselves. Of course those women put everything, and everybody, inside themselves. She also heard that some of the women in jail used things that big, but the biggest she'd ever tried was the handle of a hairbrush. But that was short, and hard, while this thing looked about 10 inches long and made of jello. "Do you want me to try it?"

"Ooooh yeah, Cheryl." He said, as he handed it to her. " I want you to rub it all around your pussy and get it nice and slick."

Cheryl took the thing from him and it felt very spongy, but definitely stiff enough. She pulled up the skirt, then raised her ass off the bed and pulled the whole thing up away from her crotch. She brought her knees up, and out, opening her pussy up before him. She was already very wet, and she grabbed the dildo by the base and touched the end to her clit. "Ooohhhh." She moaned. "That feels weird!"

"Do you like it Cheryl?" He asked. He was very excited by the sight of her on the bed, with her blouse opened up showing her tits, and her skirt up over her tummy. He watched, mesmerized by her actions, and began to remove his clothes. When he was naked, with his cock hard and sticking up & out, he moved towards the bed and removed Cheryl's sandals, one by one. After getting the second one off, he lowered her foot onto his cock, and moved her sole up and down his shaft. "Try sticking it in now. Will it fit?"

"Oh God. That feels so good." Cheryl had thrown her head back on the pillows, all thoughts of sucking her tits forgotten. Her eyes were nearly closed and she was writhing on the bed in response to her own movements of the rubber dick.

"Stop Cheryl." He commanded, and she had to force herself to lay still. She took her hand off the dildo, but it was still sticking in her a couple of inches. "Oh, it's hard to just stop like that."

"I know. I'm going to take over, okay? I want you to lay back and let yourself come. I'm going to work this thing in and out, and I want you to come, okay? "

"Can I do anything?"

"Like what Cheryl?"

"Like suck my tits again, and maybe rub my clit?"

"If it'll help, yeah. Do you have multiple orgasms Cheryl?"

"I never have before, but I've never done anything like this before either. I think maybe I could right now!"

"Let's try." He gripped the dildo by the end, it felt similar to his own cock after he had come, and his cock wasn't so hard. But it was bigger than his, and it felt exciting to grasp it. He knew it wasn't a real cock, but it certainly was exciting.

Cheryl reached down with her right hand and began little butterfly strokes of her clit in time with his movements of the dildo. With her left hand she pulled her tit to her mouth and she started biting down on her tit.

He could see, by the juices on the dildo, how far in Cheryl had been pushing it. It looked like she'd not put it in any further than his own dick would reach. He decided to push it in further to see how she reacted. He watched, slowly rubbing his own cock occasionally, as he pushed the dildo in one, then two and three, inches past where Cheryl had put it.

"God, I've never had anything in me that far before." Cheryl cried out. "I'm gonna come! Is it okay, can I come now?"

"Do it Cheryl!. Come for me baby!" He called out. He could see she had quickened her pace with her finger, and her clit was stiff as a little cock itself. He pushed the dildo in and out, not as fast as her finger, but in the same rhythm.

"Ooooooooh! I'mmmmm Commmminnng!!" Cheryl screamed out. She felt her whole body convulse with pleasure as the orgasm seemed to start in her pussy and expand outward. She arched her back upward, impaling herself on the dildo even more. Then a second wave of orgasm started, followed by another. Cheryl shut her eyes and surrendered to the feelings as the waves of pleasure swept over her.

She opened her eyes and realized he was no longer moving the dildo, but was kneeling between her legs, looking down at her. She felt very weak, and glowing.

"That was about the sexiest thing I've ever seen Cheryl. I thought you were going to pass out. You must have come for two or three minutes. It was awesome! How do you feel?"

"Great! I've never felt anything like that before. I loved it. But it almost killed me! I don't think I can hardly move."

"I need to come too, okay? I want to move up and fuck you between the tits okay?" He stood and steeped over Cheryl. She could see his dick was very hard, and when he sat astride her belly she looked down to see the swollen head of his cock pointed up towards the valley of her tits. " I need to get this wet first." He said. Then he pulled the dildo out of Cheryl's cunt and placed it between her tits, slopping a lot of her own juices on her chest. " That ought to be enough. Do you think you can push your tits together for me?"

Cheryl had done this before, and she pushed on the outside of her tits, pushing them together around his cock. She could feel the throbbing of his organ, and she knew he wouldn't last long. He leaned forward, pushing his dick in between her titis, then he began to thrust. He was so damned turned on it wasn't going to take long, and he made no effort to hold back.

Cheryl though she'd surprise him a little and leaned her head down. When he thrust up, she managed to suck the head of his cock into her mouth, and she closed her lips tight around the mushroomed head of his cock as he pulled it back out. " That feels great! I'm gonna come Cheryl. I'm going to try and come in your mouth. I want you to take it. Take it. Aaasrrrrgh! Take It!"

He started coming and it felt to him like he could have launched a rocket with how hard he shot. His cock wasn't in Cheryl's mouth when he started coming, and he could feel her trying to suck him in as he came. But he couldn't hold back and bucked and thrust with great fury, coming all over her mouth, chin and chest.

Cheryl was surprised at the strength of his coming. She was proud of the fact that he was so worked up, so excited by her, that her was practically out of control. It had been a long time since she'd had that effect on a man.

He dropped on top of Cheryl, and quickly rolled to the side. He was totally spent for the moment, and his muscles were cramped in his arms. He hadn't come like that in years. Certainly not with his wife. He didn't want it to end, but he needed some recovery time. As he laid next to Cheryl, she turned to take him in her arms, and he responded in kind. If felt very natural to hold her. Without thinking he moved to kiss her, and it took him a second or two to figure out that she was still covered in his come, and that slick, salty taste was his own semen. By the time he figured it out it was nearly gone, so he didn't worry about it. He figured if she could handle the taste, then he surely could too.

After a while, he told her to hit the shower again. He joined her, and it was apparent that he had recovered, at least enough to get hard. "Put your clothes back on Cheryl, we're going out to dinner."

"Dressed like before?" She asked.

"Oh, yeah. I don't think we're through for the evening yet.." He replied with a sly smile.