Jill Kelly Goes to Prison

Authors note: I was only planning on posting two chapters to this story, but I've been asked to fill in the time between the two, so I will.

This chapter picks up right after the First chapter. I call it, "Jill joins the club."

Jill Kelly Goes to Prison CH. 2

(Jill joins the club)

By

Deputy Duffy

Tired and on the brink of exhaustion, Jill pulled into the driveway of her Connecticut home. It had been a long drive from Vermont, which capped off an even longer day. She drew herself a hot bath and then poured herself a glass of wine. She stripped off her clothes (for the second time today), and splashed into the tub. She lit a few candles, before putting a hot washcloth over her eyes.

Her mind drifted back over today's events, questions running through her head: Did she really make it though today? Could she really go back there? Was April really interested in her as a friend? Could she really trade sexually favors like her?

The hot bath water was about the only thing keeping Jill calm. She suddenly remembered the short conversation she had with April in the prison's parking lot. She was invited back up to Vermont in a couple of weeks to meet some of the other unfortunate wives. April even called it a "little club of prisoner wives."

Taking a sip of wine, she remembered her meeting with her husband. It had been so long, his body felt even bigger and stronger than she remembered. The two spent most of their thirty minutes together locked in a loving embrace. The only words the two exchanged were "sorry" and it seemed to sum up their present positions in life, but they both vowed that they still loved each other.

Suddenly, it felt like she had been struck by lighting, when she remembered glancing over her shoulder at April. April was down on her knees, her skirt bunched around her waist, her head in her husband lap, bobbing up and down, while the young guard was only a few feet away, licking his lips, obviously enjoying the show. "Or maybe waiting for his turn," Jill thought, with a shiver.

Her stomach turned, as she pictured herself doing that to her husband, as the guard watched. Her husband had asked her several times early into their marriage, for oral sex, but Jill just couldn't go through with it. She just couldn't get over her fears about putting a penis into her mouth.

As she continued soaking, her mind drifted back to the conversation with April after their session. April told her how after her visit with her husband, she had to go into the break room and blow the sergeant, but they deputy had to leave on a call. She stuck a finger into her mouth and pretended that it was the sergeant's hard cock. She had to take it out several times to stop from gagging. "Just how and the hell do bad girls do that?" She asked herself several times.

The following week, April called several times to talk. Jill tried to learn as much as possible to try and avoid the amount of humiliation she endured in her last visit. April invited her up to her cabin, the following Friday for the prisoner wives meeting. She also said that she'd arranged to go back to the prison and visit their men on Saturday. Jill said she would come, only after some coaxing from April.

The following week was a hectic one for Jill. She needed a job and after numerous interviews she finally got one at this little bookstore. She was also suffering from a lack of sleep. She didn't know what was making her more nervous, her next prison trip, or meeting the other wives, or maybe it was spending the night at April's house. She figured it was a combination of all three that was causing her sleepless nights.

Friday, she made the trip up to April's cabin, which was relatively easy to find, as it was located among a popular ski resort. She pulled up to the cabin and spotted April's four by four. It took her nearly twenty minutes before she built up all her courage and walked up and knocked on the cabin's front door.

April answered the door with a smile. They shared a warm embrace, and then April grabbed her hand and led her into the cabin. She introduced Jill to the other women, and then the other women stood up and introduced themselves. There was Beth, an older, overweight woman. Candy was a tough looking blonde dressed like a biker chick, who could have passed for April's sister. And the last woman was a tall sexy redhead, who surprised Jill by greeting her with a soft kiss on the cheek.

"You can call me Red, as in red hot," she purred into Jill's ear.

"C'mon Red, don't scare the poor girl," April said, as she pushed Red away. "Don't worry, Red is just a little affectionate, that's all."

The wine started to flow, and the women settled into the living room and exchanged stories on why their husbands were in prison. Jill went last and they all got a kick out of Jill's story.

"I can't believe he stopped to ask directions from an off-duty Deputy," Beth cried out. "Men never ask for directions!"

"Eight years! Wow, that's along time to be locked in a little cage with another guy," Red said, and the other women nodded.

"I wonder if he's doing the pitching or the catching?" She said, and the ladies giggled. Jill didn't know exactly what that meant, but she figured it was some sort of gay joke, which made her skin crawl.

"So Jill, since it's your first time here with us, let's hear about your first visit to our little state facility," Beth said.

Jill rambled through her story rather quickly, blushing all the way, as it seemed just as embarrassing to tell her story, as it had been when she went through it.

"Jill, did you forget that I was there with you, so I know you left out a few things," April said with a laugh. "Like, it was really your second trip, as you chickened out on the first try."

"Please April, this is embarrassing," Jill cried out, a small tear leaking from her eye.

"Jill, what are we going to do with you?" April moaned. "We have to toughen you up some, can't have you balling your eyes out all the time, it's embarrassing for all us women, and I think I know where we can start."

Jill tried to clear her eyes.

"Jill, just answer this one simple question, did you shave your pussy yet, as they suggested?"

"What!" Jill gasped.

"You heard me," April said, her face serious.

"I trimmed it a little," Jill mumbled, but it was a lie.

"That's what I figured. Well, we now know what your initiation into our little club is going to be," April announced, as she stood up. "Red, go to the bathroom and bring back the shaving kit."

"Cool!" Red cried out, before running into the bathroom.

The other two women grabbed Jill by the arms and pulled her off the couch.

"Lay her down on the coffee table," April barked, and the women did, as Jill was protesting profusely.

"Let's get that ugly skirt off. I really have to give you some fashions tips, you dress like you're sixty years old," April said, as she stripped Jill's skirt off, while Beth and Candy held her arms.

"Nice pantyhose, at least you left the running trunks at home this time," April teased, as they soon joined her skirt on the floor. "Stop fighting or we'll tie you to the table…. Just like…."

Jill relaxed her body, knowing just what April was hinting at.

"Found it!" Red announced, as she ran back into the room, shaving kit in hand, naked as the day she was born.

"What the frig...!" Jill cried, when she saw Red's nakedness.

"Don't mind Red, she works hard to keep her body in tip-top shape, and she also likes to show it off," April said, holding Jill's legs.

"What, I had a new dress on and I didn't want it all messy," Red offered.

Jill had to admit that Red had a great body, her skin seemed to shimmer, her breasts were firm and her nipples were pink and puffy, but Jill started to get an uneasy feeling remembering her kiss, and April's actions at the prison.

"Please April, I'm not a lesbian!" Jill cried out, which brought out laughter from the other women.

"Hey girls, little Jill thinks, even though we are all married to men, that we're all lezbos," April said with a laugh. "Well, we might like the company of women once in a while, but we ain't no lezbo club."

April wiped a bead of perspiration from Jill's face, and then licked her finger. "Now, if you don't quit your crying we are going to have to gag you, with these," April said, as she pulled down Jill panties. "It's not like it's going to hurt to have your pussy shaved, you might even like it. Plus we're all baldies, too."

"Wow! Look at that bush, you want me to get the hedge trimmers out back!" Red teased, when Jill's dark pubic bush came into view, and the women giggled.

Jill was fighting back tears, it wasn't even the shaving, it was the fact that the shaving was going to expose her pussy to these women, and then later at the prison. Jill's body was no longer relaxed.

"Hold her girls," April said with a chuckle, as she was enjoying herself. She didn't want to be thought of as gay, but she didn't mind fooling around with other women, especially when her husband was in jail, as he often was.

April knelt on the floor, while Red spread Jill's legs apart and dropped one off each side of the table. Crouching underneath the table, she used Jill's pantyhose to tie her ankles to the table legs.

Jill offered one more plea, "Please, I can do it myself." She could tell by April wicked smile that it was a futile one. When Red stood up, she realized by trying to close her spread open legs what she had done.

"One more thing," Red said, sliding a small pillow under Jill's lower back. April smiled with approval. Jill gasped, as she saw the pillows effect.

April, working with experience, started with her scissors, trimming as much pubic hair as she could, and then grabbed her husband's beard trimmer and carved a V, into the top of her pubic mound, pointing to Jill's clit hood. Then used a straight edge and gel to shave around her pussy. Finally using a facecloth, she cleaned up Jill's new pussy.

"Well lookie here, she has a nice little pussy after all," April purred, as she ran her finger lightly along Jill's pussy lips. "Yes, this is much better."

Jill tried to struggle free, but Beth and Candy had a good hold of her arms, and the pantyhose stretched, but held there grip.

"She sure is a squirmy little fish, ain't she," Beth chuckled.

"Oh yeah, you should have seen her on the steel table in the processing room," April said with a giggle. "The deputy was giving her quite the probing. I just had to help him out, I figured she hadn't had an orgasm in awhile, so I rubbed her clit."

"April, you're a naughty one!" Beth gasped, and then she laughed.

Jill couldn't help but feel flushed when she remembered her powerful orgasm that she experienced that day. Jill was still confused, as her body was betraying her again, as April continued running her finger over her pussy. She also felt that this in a strange way was cheating on her husband.

"Please April, stop. We shouldn't be doing this, I don't want to do this to my husband," Jill cried out.

April answered by sliding her finger into Jill's moist pussy. "Speaking of your husband, you didn't even give him some relief. I mean, I saw the bulge in his pants when the guards took him back to his cell."

"I-I-I just couldn't…owww…."

"Man, you left your man all hard," Beth barked, and the other women just shook their heads at Jill.

"There is so much you have to learn girl, and we can help you a lot, but you have to trust us, plus we wouldn't do anything to hurt yah," April said, pulling her finger out and sucking it clean.

The women released Jill's arms and Red untied her legs. April pulled Jill into her body and the two locked in a warm embrace as Jill started balling her eyes out, on her shoulder. Life lately had just become one humiliating experience after the next. She wished she was more like April and the other girls, but she knew she was along ways from that. She had her doubts as to whether she could make that transition.

After an hour, Jill had managed to compose herself somewhat. The wine was helping and then she took a hot shower at April's request, only to find that her clothes were missing, as she dried off with a small cotton towel. She wrapped it around her the best she could and entered the living room.

"April, where are my clothes?" Jill asked, seeing her sitting on the couch.

"I gave them to Beth to drop in the Goodwill box on her way home, except we kept your shoes."

"What!" Jill barked, a little upset with April's boldness, while she thought, "Thank goodness I packed some extra clothes for my prison visit."

"Well, that's the next lesson," April said while standing up. "We are going to show you how to dress for your prison visits. Now drop that towel and lets get started."

"B-b-but, I'm n-n-naked," Jill stuttered, as she was quickly back to being nervous, as she watched Candy and Red walk back into the room carrying a pile of clothes. They dumped them on the couch. April looked over to Jill and motioned for her to drop the towel. Jill shook her head. April smacked her lips and snatched the towel away. Jill quickly covered her breasts with her hands. April had to laugh, remembering that she did the same thing at the prison.

"Don't pee on my rug, girl," April teased. It seemed to put Jill at ease.

The three girls surrounded Jill, each having an idea of what she should wear, and they began putting on and pulling off clothes for the next hour. Jill felt silly, never playing dress up, at least not as a grown woman. April also fixed Jill's makeup. When the women announced that they were happy, Jill looked at her reflection in the full-length mirror, on the bathroom door. She couldn't believe what the girls finally decided on, her jaw almost hit the floor. She was wearing a small black satin top that hugged her breasts, the outline of her nipples clearly defined. She had a black leather mini skirt that didn't even come down to middle of her thighs. Looking lower, she wore black knee high spiked boots, and of course they didn't give her any underwear. She started to strike different poses. It seemed like the only pose that didn't leave her exposed was standing straight up and down. She didn't think she could ever wear this outfit out in public.

Jill lifted her skirt and noticed her newly shaved pussy shining in the mirror. Looking around to see if the coast was clear, she took some time to examine it. Her pussy hadn't been this bare since puberty. She even spread her pussy lips apart, examining her inner pinkness.

"Nice, huh?" April's voice purred.

Jill nearly jumped out of her skin. She didn't even notice that the bathroom had two doors, and she also felt the sting of being caught in such a naughty act.

"You scared me to death," Jill managed, her face flushed.

"It's a lot sexier to be cleanly shaved, huh? And just a little bit dirty too," April said, moving over and pulling Jill's skirt up to enjoy her handy work in the mirror.

"Please April, you're always teasing me," Jill moaned, pulling her skirt down as far as it would go.

"C'mon Jill, it's time for your last lesson of the night. We don't want to overload you too much for one night, " April said, as she led Jill back into the living room.

Jill was thinking it was to late for that. She could have never imagined that she would have been put through all this, when she had left her house earlier. She also wondered what was next.

Jill noticed two kitchen chairs in the middle of the living room. Red was sitting in one of them. "At least she was finally dressed," she thought. She wore green hospital pants and a small tank top.

"Ok Jill, we are going to pretend that Red here is your husband and Candy is a prison guard," April said, as Candy came into the room wearing a classic police uniform, slapping a nightstick in her hand. The girls chuckled, even Jill.

"April, where…?"

"I used to work at a costume store," April quickly answered, reading Jill's face.

Candy moved closer. "Ok, if you wanna see your husband I'm going to have to see some T and A," Candy said in a deep voice, which brought more chuckles, but not from Jill this time.

"You see how much easer this is going to be in this outfit," April moaned, while Jill just nodded.

"C'mon girl, lets see those titties," Candy bellowed.

"What you want me to really do it?" Jill cried out.

"If you want to see your husband, sweet cheeks," Candy said, as she ran her nightstick over Jill's right breast. Jill batted it away.

"Believe me, you need the practice," April chirped. "Plus, we've all seen you naked already, and you have a hot little body."

Jill blushed looking down, even though this was supposed to be practice, it felt a little too real as she lifted the bottom of her small shirt and rested it just over her breasts.

"Nice, I just love marshmallows," Candy purred, forgetting her deep voice this time, as her nightstick returned to Jill's breast. "That's the T and now the A."

Jill trembled as she turned around and bent forward. She could tell by the looks on the other women's faces that they must be enjoying playing their little perverted game. She felt her skirt being lifted up in back, letting out a gasp when the skirt flipped inside out and gathered around her waist. "Please," was all Jill could manage, feeling the smooth stick brush against her pussy lips.

"Ok slut, you can see your jerk off of a husband now," Candy said.

"Honey," Red cried out, while standing up. "Oh, you look so good, and it's been so long," she said, trying to deepen her sexy voice.

Red moved over and hugged Jill, while running her hands up and down Jill's back, making sure they ran over her naked ass. Things were happing a little to fast for Jill to even protest. Red grabbed Jill's face and starting kissing her. Her kisses slow at first, and then proceeding to a full-blown make out session. It startled Jill at first since she had never been kissed by another women before, but she closed her eyes and pretended it was her husband, although her husband's lips were not nearly as soft as Red's were.

Jill was surprised again when Red's lips left her lips, but quickly found her nipple, sucking on it for several minutes. Jill figured she couldn't have stopped her even if she wanted to. She had to admit to herself that it felt pretty good, although the audience make her uneasy.

"Oh honey, you are making me so excited. I'm as hard as a rock," Red oozed, as she guided Jill's hand to her crotch.

"What the fuck!" Jill cried out, as she felt a large hard object in Red's pants. She jumped back, forgetting about her spiked boots that were a little too big for her, and crashed to the floor.

"You all right Jill?" April said, as she helped Jill off the floor. "I'm sorry, I guess we forgot to tell you about the strap on dildo thing."

Jill looked over at Red who had her pants around her ankles and was rubbing a flesh colored dildo that was strapped between her legs. She also wore a sly smile on her face. "I told yeah, I was hard."

"Man, it scared the shit out of me…I never saw one of those before," Jill gushed.

"Really! Big surprise there," April said sarcastically.

"W-w-what's it for?" Jill mumbled.

"Well, it's for a lot of things, but for right now, it's so we can pretend that it's your husband's cock. You see, I think it's basic blowing lesson time," April said, with a smile.

"You're kidding, right…? I'm not putting that thing in my mouth," Jill barked, seeing that they were serious.

"For a married woman you sure have a penis phobia. Do you let your husband put it in your pussy?" April teased, while Jill just flashed her a dirty look.

"All right, you remember how scared you were the first time you let a guy slide his cock into your pussy?" April said, patting her on the shoulder, while Red continued to stoke her man made cock.

"Ah, yeah, it was my husband, well before he was, and he has been the only one," Jill mumbled, her face burning.

"Really?" April said, a little surprised at her admission. "And now you probably like it. Well sucking cock is the same thing. You're scared to death the first time you do it, then it gets easier after that, and if you learn really good, you can get men to do anything you want. Right girls?"

Jill didn't know if she was buying it or not, but her logic seemed to make sense. She also knew deep down from the sounds of it, she wasn't going to make it eight years in the state prison, without ever having to do it, and she knew her husband would probably benefit.

"Now, you wanna learn how to suck dick, or not?" April asked.

Jill took a deep breath and nodded meekly.

"Alright, then take off your clothes and get over here." April said, pulling her top off. Jill's jaw dropped noticing Candy stripping too. Jill shook her head, wondering how many times this was tonight, as she began to undress. When the three women were naked, April pushed Red onto the wooden chair, and pulled off her tank top. Candy dropped three pillows on the floor and Jill knew that one was for her. With the three women kneeling in front of Red, she watched as April went first, then Candy, and then it was Jill's turn. Jill closed her eyes and slowly took the toy dildo into her mouth, and the other three women broke into applause. The next time she went, Jill felt someone fondling her breast, but with her eyes closed she wasn't sure who was doing it, but they certainly had soft hands.

For the next half hour, April and Candy showed Jill the basics. She still gagged here and there, but at least she didn't feel like puking, like she thought she would, and she even got a little more used to the girls fondling her breasts, while she sucked.

"But was she ready for the real thing?" she asked herself.

When April finally announced that it was getting late, and that Jill had learned enough for one day, Jill felt relieved, plus her jaw was starting to ache.

Jill and April cleaned up in the bathroom, where April suggested that they get ready for bed. April handed Jill a naughty nighty to wear. Jill followed April out of the bathroom, and she stopped dead in her tracks, at what she saw, on the couch. It looked like Red was fucking Candy from behind with the strap-on.

"And that's another use for it," April whispered, as she grabbed Jill's hand. "C'mon, let's let them play, and go to bed," she said, tearing the stunned Jill away from the living room and headed for the bedroom.

Jill was still apprehensive as she climbed into bed with April with everything that had happened today.

"Don't worry, I won't bite…but I will lick, if you want?" April purred, stroking Jill's hair.

Jill's head was spinning, "You mean, you want to lick my pussy?" She finally managed.

"Wow, you're so precious," April purred. "You better get your sleep now, you've been through a lot today and you have a big day tomorrow," April said, as she kissed Jill goodnight.

Jill closed her eyes. April finally said something that she totally agreed with.

The End...For now

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