Jill Kelly Goes to Prison

Jill Kelly Goes to Prison Ch.5

By

Deputy Duffy

"Jill, why don't you go to the fridge and get the deputy another beer. He looks like he could use it," Red teased.

"He looks like he could use a cold shower!" Candy cried, and the women all giggled. The deputy bit his tongue, thinking about that line about, he who laughs….

Jill, with a huff, went to the fridge and got the beer.

"I guess you all want to know why the deputy is really here." Jill heard April say when she returned. "Well ever since I saw the deputy in prison that day, and gave him my number, we've been talking on the phone about the one thing I know we all want."

"He's gunna get our men out," Candy cried out.

"I'm good, but not that good," the deputy said, cracking open the beer.

"No, but he gunna pull some strings and get us one hour with our man…no guards…no one watching."

"Someone's always watching," Candy said, skeptically.

"Not in the break room, that's deep in the prison. No one uses it, so there aren't any cameras, and the guard will be outside the door," the deputy said.

"C'mon girls, how cool would it be to have one hour alone, and just think how our men will feel," April said.

The women all looked at each other and then started hugging. It is what they all wanted since their husbands were incarcerated. It was the next best thing to having them come home.

"Wait a minute, why?" Candy said, interrupting the celebration.

"Why, what?" April asked.

"No, why would the deputy do that for us? We know that conjugal visits aren't allowed," Candy said, as she looked at the deputy and the rest of the women followed. The deputy sat back and took a sip of beer. It was now time…time to see if they wanted to play.

"I could say because I'm a nice guy, but we know that's not why," the deputy started. "Well, when April first asked me for this, I thought, you know, April knows how things work. If I do something for her, well, she does something for me. So I looked into it and well it was going to take some doings, but I could pull it off, since I know enough people."

"Yeah, but I also thought of my girls as well," April interrupted.

"Yeah, she had to do some convincing on that one. I mean, one convict free pass was one thing, but three more," the deputy said.

"Hey, what about Beth?" Jill moaned, doing the math.

"Beth, well her hubby should be out in a month or two," April said, before she reminded them. "He really is going to have to stick his neck out for us, if we are going to do this."

"Why wouldn't we do this?" An excited Red spat. Jill and Candy also seemed to be waiting for the answer, as April and the deputy were exchanging glances.

"Because you have to pass a little test," the deputy finally moaned.

"What test?" "C'mon," "What the...?" Candy cried, and the other women soon followed.

"Hey, settle down," April cried out.

"It's a test, to prove to me that you are worth sticking my neck out for," the deputy said sternly.

"We're not going to like it are we? All you pigs are the same!" Candy barked out, as she couldn't hide her true feelings for the deputy any longer.

"Well, I can see I wore out my welcome," the deputy said, as he rose to leave.

"Candy, shut the fuck up!" Red cried out, and she hopped up and grabbed the deputy by the arm. "Please at least tell us about the test. My old man has three more years."

"It's not really a test, but more of a challenge. If you pass, we win and if you fail, then the deputy wins," April said quickly.

"I'll grab another beer and I'll wait in the kitchen. You talk it over. If you don't want my help, no biggie," the deputy said, before he walked into the kitchen.

"April, why the fuck did you invite him here?" Candy whined, which Jill was surprised at, as she had acted like she was comfortable with his presence all along.

"You guys aren't looking at the bigger picture…the prize if we win," April whispered.

"We thank you for that, but as much as I want to be intimate with my husband, I know when you tell us what we have to do, I'm gunna want to kill you again, ain't I?" Candy said, shaking her head.

"C'mon Candy, let's give her a break for a sec. Go on tell us April," Red said.

"Well, it's p-pretty simple," April mumbled, as she could feel the heat from the other women's stare. "You have five minutes."

"Five minutes to what?" Candy barked.

"Well, to ah...hummm," April murmured. "To get the deputy, up and down."

"Fuck, April!" Candy cried out. Red also threw a pillow at her.

"Ok, now you can kill her, Candy!" Red screamed.

"What guys?" Jill said, as she was a little confused.

"Up and down, is prison slang for getting someone off. You know, making someone cum," Candy snarled.

"We have five minutes to make the deputy cum," Red said, as even she wasn't happy with it. "And he's probably a limp dick."

Jill sat, her mouth agape. April had to know how much distain she had for the deputy. After all, she was there the day they first met. She knew their history. Surely she must understand.

"April," Jill moaned.

"Look, there is three of you and one of him," April tried to explain.

"Three of us, what about you," Candy interrupted.

"I...um.…"

"You fucking slut!" Candy cried out.

"Look, you know how it is. He did a favor, so I had to return it," April said, trying to retain her composure.

"What did he do? He's a fucking deputy ass clown. He even busted Jill's fucking husband," Candy cried out.

"He ah.…"

"He did me a favor too, I think," Jill interrupted.

"What Jill?" Candy moaned, as the fire of the room suddenly cooled.

"I mean, I was new and nervous and well I didn't know anything and…." Jill rambled, nervously fighting back tears. "And then April said she would, but I didn't know what she meant. And then last time, there was this mean guard giving us a hard time. I thought he might even rape us, but the deputy helped us out."

Jill held her hands to her face, as she lost control of her emotions, nothing new for Jill, only this time the other women felt for her, as they felt many of the same emotions, only time had hardened theirs.

After several minutes, the women finally helped Jill clean her face, and Red held her in her arms.

"Ok, April, I think we see why you did what you did, but there is still one thing your not telling us," Candy said, as she leaned back against the couch. "How about telling us what happens if we can't, well you know, in five minutes."

The women seemed to all share the feeling, their gaze locked on April, who shifted nervously in her seat.

"Well you shouldn't fail. I mean, why do you think I told my story and talked Red into telling hers," April said, with a nervous twitch.

Jill looked up into Red eyes, as if to apologize for some of the things she said to herself about Red. Red seemed to understand, as she gave Jill a quick soft kiss on the lips.

"But what if...?" Candy said.

April gulped. "If you fail, well, then for one night, we're, ah, his personal play thing," April said, her voice trailing off.

The three women didn't even move, or hardly even breath, as they looked at April, not sure if they heard her right.

Candy huffed. "Did you just suggest we wager the one thing that we have left, our last straw?"

"C'mon, it's just for one night, and we'll even be in pairs. Me and Jill, and Red and Candy, but you shouldn't lose!" April pleaded.

"April, one night, you mean we have to...?" Jill groaned, catching up to speed.

"Yes Jill," Red answered for April.

"Yeah, anything he wants," April mumbled. "But look if I was you guys, I mean five minutes is a long time, and he is no limp dick, so here's what you guys should do."

The deputy walked back into the room, interrupting April. "April, I'm getting a little lonely in the kitchen. Let's let the ladies decide," the deputy said, and he took April's hand. "You have five minutes to decide."

The deputy returned to the kitchen with April in tow.

"I can't believe this!" The women said to each other, at first.

"Man, what's he have a 'five minute' fetish!" Candy quipped.

"I'm sorry girls, I should have told you he was coming," Red said, before she quickly added. "But I didn't know anything about this. Jill just told me to tell my story in front of him, and to make it extra sexy, and hot."

"So you made up the story?" Candy asked.

"Just a little," Red said with a nervous giggle. "When we got into the bedroom, Wendy was all over me and Danny was begging to watch. Finally, after some convincing, Wendy said he could, but he would have to watch from the closet, so she could pretend he wasn't watching. That's what really happened, and then she switched places with him and that's basically it. They never touched each other, I just added that part for the deputy," Red said, and Candy giggled, before Red added. "And I wouldn't let some pimple faced teenager fuck my ass. You should know that Candy."

"It did surprise me."

"Alright, let's figure this out," Jill said, as she was growing nervous with the sex talk.

"Well, we have to do it," Candy mumbled.

"You mean?"

"No, I don't want to do it Jill. I hate pigs, but we have to now. If we back out, we'll hurt the deputy's feelings," Candy said.

"So," Jill snapped.

"She didn't mean it like that," Red said. "It's just, he knows enough people in there to make life easy for our men, but he can also make life hard for them…real hard," Red said, as she stroked Jill's hair. Jill took a deep gulp, as she never even thought of that.

"But listen Jill, me and Red can handle most of it. In fact, I'm hopping Red can work her magic tongue," Candy said. "You said you can suck as good as April, now's your chance to prove it."

"I never said that, did I?"

"Have you guys ever?" Jill mumbled. "You know."

"What? Oh, I hope you're asking about the deputy?" Candy groaned.

"Ah, yah."

"The only time I saw him before today was just outside the prison, last time," Red said and Candy was shaking her head. "And you Candy?"

"I saw him, too. That's why I got the hell out of there."

"Why?"

"Ok, but don't tell anyone this, but he arrested me once,"

Candy said, her mind going back in time.

"What for?" Red quizzed.

"One stupid joint, in my butts pack."

"What happened?"

"Well, so, he brings me to the station where he strip-searches me…probes my pussy and ass and everything. Then I could tell he wanted me to suck his cock. He hinted at it, but I wouldn't. I told him I rather rot in jail, and now…. Life is so twisted." Candy said, before she turned to Red. "Red, do you mind? I mean I'll help, but I'll puke if I…."

"I understand. He's just pretend he's a stranger to me, but, ah, maybe you can jerk him, or cup his balls, while I'll use my mouth. I hope April taught me well," Red said, and she giggled nervously. "And Jill, I know you're not going to like this, but you can use your tits, ah, those nipples."

"What do you mean?"

"You know Jill, rub them in his face, let him suck on them," Red said.

"Oh, really?" Jill moaned.

"Hey, I'm gunna have his cock in my mouth and then when he comes…." Red said, as her voice trailed off.

Jill saw her point, but was still dealing with the realization that they were going to actually play the deputy's perverted game.

"Oh god! If my husband ever found out that I sucked off a cop, he'd kill me," Red cried out.

The deputy walked into the room followed by April, who was looking down at the floor. She was also buck-naked, her nipples showing signs of sexual contact.

"What the!" Jill gasped.

"Ok, ladies, as you can see April's already got me going. Now what's it going to be?" The deputy said, as he walked back in forth in front of the women.

Red finally broke the uncomfortable silence, "We'll do it."

"Oh, thank god," April moaned. This surprised Jill, and she figured that April had something more riding on their decision then she led on.

"Five minutes ladies. Here April you time them," the deputy said, as he produced a stopwatch and tossed it over. "Ok, only one little thing to do first, and then we will start."

They watched the deputy, who was doing his best to hide his excitement over the group's decision, bend down and take something out of his sock, under one of his pant legs.

"Only one rule…you have to wear these," the deputy said, as he held up three zip-ties.

"Hey, no fair…we can't use our hands," Candy cried out, surprised that the deputy would try something, after they agreed.

"I didn't say you couldn't, you're just gunna have your hands behind your back…or no go," the deputy said, confident they wouldn't back out now. He also knew he probably didn't stand a chance, otherwise. Ever since April helped him come up with the plan, the deputy would enlist the help of his girlfriend Farrah, who after hearing the plan, would do her best to try and make him cum in less then five minutes. She tried everyday. Sometimes the deputy could hold out, sometimes he couldn't. It was this fact that led him to the "no hands" idea. He even made sure before he came over this evening, that she gave him her fiercest blowjob. Her reward, a promise to participate in the "fun" should the deputy hold out.

"Let's go, stand up," the deputy said, trying to sound as authoritative as possible, while trying not to give them time to change their minds.

The three women slowly stood up and the deputy moved in front of the dirty blonde, with the bad attitude, Candy. He spun her around and quickly slipped her wrists into the Zip-ties, before she could protest anymore, and then he spun her back around. He spent a couple of seconds looking her right in the eyes. She sported the look. He had seen that look before: Total lack of respect for the law.

"Shirt on, or off?" The deputy asked.

"What?"

"I Just thought, well, your choice," the deputy said, as he moved over in front of Red.

"Wait a sec, off, take it off!" Candy cried, as much as she didn't want to, she conceded the inevitable and also was hoping for a head start. She also was just trying to show the deputy that she wasn't afraid of him or his stupid test. Jill and Red both looked at Candy wondering what she had planned, and what the deputy had planned.

The deputy shifted back, and slowly moved his hand up to the top of the shirt. Smiling, noticing that its collar had been cut into a V. He grasped it right in the V, exposing Candy's impressive cleavage, and then in a violently quick motion, ripped the shirt in half.

"What are you Hulk Hogan!" Candy said, trying to show strength.

"Ah, nice, better than I expected," the deputy said, as he ran a finger over Candy's breast, finally rolling her nipple back and forth. Just when it looked like Candy was going to react, the deputy spun her around. Grabbing her wrists, he pulled up on them, forcing Candy to bend at the waist and lean forward, as she screamed out, not from pain, but at the suddenness of the movement. He took a couple seconds to tie the shirt pieces around her elbows

"Please Sir," Red pleaded.

"Quiet," the deputy screamed, and he brought his hand down and smacked Candy's ample backside several times. The sound of his blows jolting each of the women. Candy received one smack for each letter in the word "pigs." He spun her back around and moved over in front of Red, to avoid any sudden retaliation.

The deputy reached out and stroked Red's short hair, admiring her beauty, before moving his hands down her robe.

"Nice robe, on or off?" The deputy whispered.

"Ah, off, I guess," Red said, following Candy's lead, although she really didn't know why. Red was proud of her body, but wasn't looking forward to the deputy taking liberties with it. Red didn't have a submissive bone in her body. She was always the one in charge, even in the bedroom.

The deputy smiled, inwardly. Red was the one woman in the room that he hadn't seen naked yet. He grabbed the robe's silk bow and untied it. He licked his lips and slowly pulled the small robe open, by slowly sliding the robe off one shoulder and then the next. He almost let out a small gasp when Red's perfect body came into view. Only his training had kept him stone-faced and in control. He turned her around and slipped her wrists into the zip-ties.

Looking over her shoulder, the deputy slid his hand down Red's body, circling each breast, and down her flat stomach. He pushed up on her wrists and she responded quickly, by bending over, hoping to avoid the spanking part. But the deputy was focused elsewhere. He licked a finger and slowly worked it around her glorious, hairless pussy lips. Red held her breath, as she felt the deputy spread her open, before slowly pressing a finger in and out.

The deputy was only broken from his trance like probing when Red moaned loudly. He quickly stood up, and cleared his throat. He wiped his brow. "Ok, who is next?"

A small tear rolled down Red's cheek. Candy bumped her shoulder, and Red knew what she meant. As humiliating as it had been for the women, their plan was working, because the Deputy now showed obvious signs of excitement.

He moved in front of Jill. "And now the shy one," the deputy said, as he fondly remembered their first encounter. He always enjoyed the shy ones.

"Sweatshirt," the deputy said.

"Like I have a choice," Jill sighed.

"Fine, leave it on."

Jill could tell from the frowns on Red's and Candy's face that they weren't happy with her answer, either.

"Off," she said, looking to the floor.

"What's that," the deputy said, a hand to his ear.

"Off, you can take it off…Jerk."

"And there is that temper I remember," the deputy said, as he moved over and lifted the sweatshirt over her head.

"Pussy Power, I guess we shall see," the deputy teased.

Jill's skin crawled, as the deputy looked her over, dressed only in her sheer black negligee. She almost looked as dirty as she felt. He spun her around and zipped her wrists.

Jill felt helpless, as the deputy's hands slid down her body. He slid her g-string down her legs and picked up one foot and then the other and held them up.

"Hey, what happened to the granny panties?" He laughed, remembering the past. "And it looks like someone has shaved."

He spun her around again. Looking into her eyes, he was hoping his expression was effectively transmitting the immense pleasure this was giving him. The deputy was used to having women strip for him, so it was an added bonus to be able to do the stripping. He reached down and caressed each breast, and teased her nipples with his thumbs. He remembered the great nipples the girl sported. Reaching into the top of her negligee, he pulled out her left breast from its hiding place and then the right one, and returned his attention to her nipples.

"Ah, sir, can we start now?" Red moaned, as she was hoping to spare, a teary eyed Jill, from any more fondling. She could also see that Candy's plan was really working well, because the deputy's pants sported a distinctive bulge.

"Why not," the deputy said, as he moved to the center of the room, where he took off his sweatshirt and tank top. He pulled his belt out of his pants and moved over to April and draped the belt around her neck.

He moved back into the center of the room. "Hit it, April."

The women stood in stunned silence at first.

"Go girls!" April cried out, and the surprised women jumped and approached the deputy. Red dropped to her knees in front of the deputy and Candy spun around and was doing her best to unbutton the deputy's pants. Her wrists feeling the stinging pain, as the zip-ties pinched her flesh.

"C'mon Candy," Red moaned. She also used her face to rub against the deputy's groin.

Jill stood frozen, looking at the deputy's face. He was just staring straight ahead, like he was in a trance, like he was trying to go to a different place, a different time in his mind.

It took Candy a full minute to get the deputy's pants undone and his fly down, and another thirty seconds to get them and his boxer briefs down to the middle of his thighs. Jill gasped when his cock sprang free. Red licked her lips, as she had access to his cock now. Red took as much of it in her mouth as she could, trying to get it well coated as quickly as she could. She was almost laughing at the absurdity of it all, while trying not to be impressed, although, she had seen bigger.

"Let's get him on the couch, so we can all help," Candy cried out.

Jill and Candy used their shoulders to push him over to the couch, while Red shuffled forwards on her knees trying to keep his cock in her mouth. The deputy, who was doing his best not to break out in laughter, finally tumbled onto the couch. Red went back to work, and she now had help from Candy. Candy also flashed a look towards Jill, who knew it was her time to act. Jill put her knees on the couch and leaned forward. The deputy, taking the bait, hungrily took her nipple into his mouth. Sounds of sucking skin filled the room.

April screamed out, "One minute left." The deputy was happy to have Jill's distraction. He focused on Jill's breast as much as he could, as Red was now at full speed and suction. She even deep throated him several times. Candy was sucking on his inner thigh, and flicking her tongue out, trying to lick his ball sac, while trying to stay out of Red's way, as she furiously moved her head up and down. Candy was also fighting off her frequent urges to clamp her jaw down tight.

"Ten seconds," April cried out, and she feared that they weren't going to make it. Red was bobbing franticly. She was puzzled, everything she tried, nothing seemed to work, even though his cock remained hard throughout, and she had sucked as hard as she ever had.

"Boy, that was a long ten seconds," the deputy said with a laugh.

"Time," April finally groaned, and the room erupted in a chorus of cries of foul play, as the deputy quickly scrambled to his feet, a little apprehensive of the women's immediate response to losing the bet. He also kicked his pants and underwear off from around his ankles.

"C'mon, shut it," the deputy barked, having enough of their crying. He laughted. "There is no crying in cock-sucking."

"Fuck you, you fucking…." Candy cried out, but stopped, when the deputy raised his hand.

"Say it!" the deputy spat. "It doesn't look like you're in any position. I'm sportin' wood and ready to go. Don't temp me."

"She's sorry," Red chirped, and she knew he was right about their position.

"But don't worry. You'll get the hour with your husbands, just for being good sports. Now don't say anything more that might make me change my mind," the deputy said, stroking his cock.

"We won't, and thanks," Red said, trying to play piece maker, as she could still see that Candy was steamed.

"That's a good little girl," he said, and then he lifted Red off her knees and pushed her in between Jill and Candy, who were sitting on the couch. "That's it, stay there." He wanted Red's impressive back view.

The deputy looked over to April, who was still sitting on the recliner, waiting for her punishment.

"Crawl," the deputy ordered with a snap of the finger.

April whimpered. She took the deputies belt and lopped it around her neck, pulling it tight, and then she dropped to the floor. She slowly cat walked over to the deputy.

"That's a good girl," he said, taking the end of the belt.

"I am yours," April said, looking to the floor. "May I please suck your cock?"

"That redhead was good, but show'em, how it's done," the deputy said, pulling up on the belt and running his cock along her lips. "Yeah, that a girl."

April had already sucked him off before. But not in front her friends, and she knew how they felt about him, so she sucked hard, praying that he wouldn't last long.

"Don't forget my balls."

"Of course," April sarcastically moaned, as she already knew he liked that. She also knew now that he intended to draw out the show.

Jill closed her eyes, as April licked and sucked his balls. She just couldn't watch anymore.

"Ok, back to work," the deputy said, grabbing April's blonde hair. April took his cock into her mouth and braced, as she read his intentions. The deputy started slowly and then picked up the pace of his face fucking. Jill opened an eye, and quickly closed it, with a cringe. But even with her eyes closed she could still hear April's moaning and gagging gasps that seemed to go on forever.

April gasped loudly for air, when the deputy finally pulled out of her mouth, and began jerking his cock.

"Give me your eyes!" he barked, pulling back on her hair. He blasted a shot of cum, followed by several small ones onto April face. "Yes, finish me…finish me." The deputy pressed his cock against April's lips and she milked out the rest of his cum with her mouth.

"Show them," the deputy said, turning April's face towards her friends on the couch. Jill opened an eye, but quickly closed it. "Ok, don't look."

The deputy took his belt off April's neck, and she stumbled to the bathroom.

The deputy picked up his clothes and walked to the kitchen. Jill looked to the other girls, but they were looking to the floor, Candy mumbling under her breath. The deputy washed himself in the sink and grabbed a slice of pizza and the last beer from the fridge. He wanted to let the women cool off and he also had to regain his composer. After he dressed, he found a thin carving knife in a draw and returned to the living room.

"Miss me?" He teased, entering the room. "Now are you girls going to behave and do exactly what I say?

"Oh my god!" Jill screamed out, when she saw the knife.

The deputy laughed. "Relax girl, I don't need a knife to get women to do that…I have a badge."

The deputy used the knife to cut Red free and then Candy. They both went running into April's bedroom.

"Ah, Jill," the deputy moaned, as he moved behind Jill and cut her free. "I can't wait to have you with April."

"What are you talking about?" Jill snapped. "I thought you said we got our hour?"

"I did," the deputy said, spinning her around. "But you still lost, so you have to pay up." He leaned forward, but Jill turned her head away from the kiss.

"Yeah, you probably want her as much as I did," the deputy said, and he kissed her cheek.

"Let go of me, creep." Jill said, as she broke free. She picked up her sweatshirt and put it on. "One of these days you'll get yours."

"I try and get as much as I can," the deputy said, and he laughed.

Red and Candy came back into the room, but left quickly, after they kissed Jill goodbye, and made sure she was all right.

The deputy looked at his watch, "Looks like it's time for my exit as well. I look forward to our next meeting."

"I can't wait."

The deputy, didn't miss the sarcasm in Jill's statement, in fact, it turned him on.

"Just let April know how much I enjoyed her hospitality," the deputy said, as he walked towards the door.

When the Deputy left, April came out of the bathroom.

" April."

"I know…the deputy still wants his night with us," April said, before she gushed. "I'm sorry Jill. I really felt you guys could do it. I didn't know that he would still have his pants on. I even fooled around with him in the kitchen, but you probably noticed that."

Jill didn't want to think about that, although, she couldn't get the image of April with the deputy's belt wrapped around her neck and his cum dripping off her chin, out of her head.

"Jill, if you want to leave, for your long ride home, now would be the time," April said, as she sat down next to Jill, staring into her eyes.

"I, ah, I just want to be with you, stay with you," Jill mumbled, surprised that she could say it at all.

"Awww, that's so sweet Jill," April said, and they shared a warm embrace.

"Whatever happens with the deputy, just remember I would never let anyone hurt you, Jill," April whispered into Jill's ear, she turned Jill's face. "You can trust me."

"I trust you, April," Jill said, wrapping her arms around her.

The End

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