Jill Kelly Goes To Prison Ch. 1 & 2

"That's over two years?" April interrupted.

Jill looked down somewhat ashamed, it even seemed ten times longer.

"If you love him, and you wanna stay with him, you have to check your ego at the door, and swallow your pride, otherwise forget he ever existed and move on," April hissed.

"No way, he is the only man I'll ever love," Jill interrupted.

"I know how you feel, I would never leave my dumb ass husband either. Ok then here is how it works around here, quickly cause we don't have much time," April hissed as Jill leaned closer.

"When you come to visit, wear something like me, something simple, forget the bra, cuz they won't let you take it in anyways," April whispered into Jill's ear.

Jill couldn't believe what she was hearing.

"If you wear an outfit like yours, then their gonna make a big show out of stripping it off of you, you'll see. Usually I just flash em, and then I'm in," April groaned.

Jill looked at her with a quizzical look on her face.

"I think they just wanted someone more experienced, to make it easier for yah, they told me how you chickened out last time," April continued as Jill shook with anger, remembering that day.

"You have to pretend you like them no matter how much you wanna scratch their eyes out. Look if they sense fear and loathing they will just use it against yah, they are all power hungry," April said.

Finally, That was one thing Jill could agree with.

"And when you finally make it in to see your old man, dressing like this works too, as it gives your man easier accesses to your body, you see the guards won't let you take off your clothes, in the visitors room." April said.

Jill once again flashed April a shocked look.

"Believe me when your man finally she's yah he's gonna want touch you everywhere and he's gonna want to be touched, shit their locked in cages 23 hours a day, 23 hours, 7 days a week, do the math girl," April continued.

Jill looked down in humiliation again. She also hated to think of her powerful man locked up in a cage like an animal.

"Don't the guards watch...I mean?" She mumbled.

"Yah they watch, their perverts too, but believe me you'll get to the point where being with your man is more important, then a few stares," April moaned, "Oh yah, just don't tell your man what you had to go through to see him, there are some things a guy in prison just doesn't need to hear."

Jill watched as the two men ended their conversation and sauntered back over towards them.

"Where were we, ah yes Jill are you ready?" Duffy asked.

Jill nodded her head, still spinning from April's sermon.

"Very good then, why don't you start by unbuttoning that sweater," Duffy commanded.

Jill's fingers trembled with her buttons; she had lied when she said she was ready.

"Ok now hold it open," was the next order.

Jill slowly opened her sweater up, exposing her white bra.

"All the way," Duffy barked.

Jill spread out the sweater a far as it would go, her arms were like rubber, tears already forming in her eyes.

After a minute, she finally took it off, per Duffy's orders, and handed it to Adams for inspection.

"Ok lift your bra away from your tits and shake'em out," Duffy hissed.

Jill hesitated for a moment, a little confused by the order and she also just hated the word (tits.)

"Need some help," Sergeant Adams barked.

Reluctantly Jill pulled the cups away from her breasts and shook her shoulders.

"Lean forward and continue," Duffy hissed.

Jill did so, almost breaking into tears, but trying not to give them the satisfaction, somehow, someway, she had to make it though this.

"Ok since bras aren't allowed in the visitor's room, I'm afraid I'm going to have to confiscate it, hand it over!" Sergeant Adams barked.

Jill looked at April who was standing next to her, she flashed her that (see) look. Jill's face flushed as she reached back and unhooked her bra, no one but her husband and her doctor had seen her naked since she developed. Her Husband had been her one and only lover. Slowly, unintentionally seductive, she slid the straps off her shoulders and pulled it away from her body, she handed it over to Sergeant Adams and then quickly covered her breasts with her hands.

"Look buddy another one for my collection, man this thing is heavy," Adams said, as he held it in front of his own chest.

The two men laughed, which just added to Jill's embarrassment and then they just stared at her.

"What?" Jill managed.

"Are you gonna just stand there and massage your tits all day, or are you gonna put your hands down so we can inspect your titties?" Duffy said with a smirk.

Jill slowly dropped her hands, while the two men didn't even hide the fact that they were gawking at her. Jill just wanted to die, she looked down at her breasts, they were medium sized, a little on the pointy side, but it was her pink marshmallow like nipples that embarrassed Jill the most, but from the smiles the two men traded, it didn't seem to bother them.

"Ah hum...unbutton your pants," Duffy managed, almost losing his professional demeanor for a second.

Jill fumbled with the three buttons on her pants.

"Ok now put you hands over you head," Duffy said.

Jill did so although a little confused.

"What's this all about?" She thought.

"Now shake your hips," Duffy ordered.

Jill slowly, reluctantly, shook her hips, she also knew that she was shaking her tits too. She looked at April, who again flashed her that (see) look and Jill remembered what she said about them making a show out of it. She also whished she talked to April sooner, as her pants started to slither down her thighs before dropping around her ankles. She also finally got the shaking the hips thing.

"What you planning on doing a little jogging later," Adams said as Jill running shorts came into view.

"Can you please pull the shorts down?" Duffy said annoyingly. "I thought her pants were awful fluffy earlier," he thought.

Jill heard laughter as she pulled down her shorts that raveled her large white granny like panties; even April couldn't help but chuckle at poor Jill's panty selection.

Jill's face was beet red, her heart felt like it was going to exploded out of her chest, she again thought she might die of embarrassment.

"Are there any more clothes under your huge granny panties?" Duffy hissed.

Jill could only shake her head back and forth.

She looked at Deputy Duffy with watery eyes, he just placed his hands on his hips and tapped his foot, Jill knew what he wanted, she mustered up all her strength and rolled her panties down. Standing back up she used her hands to cover her crotch.

"Now finally, please turn around," Duffy barked.

Jill turned around; it was a little awkward with her pants, shorts, and panties still wrapped around her ankles.

"Now bend forward at the waist and untie your shoes, take them off, and remove the pants and stuff," Duffy barked.

Jill bent over and started to untie her shoes when she looked at the two men between her legs, they were staring at her back side, that's when it hit her, the view she must be giving them in this position. She picked up the pace and piled the rest of her clothes on the table.

Sergeant Adams again examined them.

"C'mon get your cute little ass on the table, lye on your back," Duffy punctuated his command with a slap on Jill's ass.

Jill hoped on the table and fell back her feet dangling of the side.

"Now what the hell is he doing," she thought.

"Put your feet up on the edge of the table," Duffy barked.

Jill looked down; Deputy Duffy was now standing in between her legs, she had to spread her legs wide to avoid him, as they now rested on the edge.

"Wider!" Duffy barked, "that's better," when she replied.

Jill had never been this mortified in her life. She always hated this position at the doctors' office, but here and now, in front of this asshole, it seemed a million times worse.

"How was she ever possibly going to do this again?" She thought.

"Jill you know it would be easier on everyone if you would shave your pussy, next time," Duffy hissed.

Jill just couldn't believe this could get any worse.

"Since I can't do a visual search I'm going to have to do a manual one," Duffy hissed.

Jill was wrong, it just did.

"Now Jill before I proceeded I have to have your permission, just to be ethical." Deputy Duffy said.

Jill looked at Deputy Duffy with a stunned expression.

"Ethical, this asshole doesn't have an ethical bone in his whole body," Jill thought.

"You can't be serious," Jill said.

"I'm afraid so, or you'll have gone all this way for not," Duffy said.

Jill looked at Duffy in disbelief, "how could such a nice looking young man be so evil?" She thought, "I can' believe I'm doing this."

"I need to hear it out loud," Duffy barked.

"Man I can't believe this," she screamed out, "all right search my fucking pussy, is that what you wanted to hear?" Jill said, as she had just about enough of this mother fucker's mind games.

"All right, I think I will!" Deputy Duffy hissed, "If I can find the fucking thing, under all this pubic hair!"

Jill closed her eyes as Deputy Duffy's finger found it mark, slowly entering her pussy. She cringed at the Deputy's light laugh, he was obviously amused at how wet she had involuntarily become. Jill squirmed about on the table as Duffy added another finger into her pussy and was thrusting them upwards and inwards, finding Jill's special spot.

It had been a long time for Jill, she was always worried about her husband in jail and in prison, to worried too even masturbate, so as hard as she tried to fight it, her body was betraying her, Jill felt another finger start to rub her now exposed clit.

"Hey what the..." she groaned.

Jill open her eyes and was surprised to see that the finger rubbing her clit belonged to April. She was sitting on the table next to her and just pressed a finger to her lips and hissed.

"Was April doing this because she wanted to, or were the two guards making her?" Jill asked herself as her head started to swirl; her skin tingled, audible moans now escaping from her lips.

"Oh my god, not now, not here!" Jill thought, as she felt a soft hand now squeezing her breast, fingernails lightly scrapping her nipple, she didn't have to open her eyes to know who was doing the squeezing.

Deputy Duffy's fingers were now aggressively thrusting in and out, much harder and much more skilled than she had ever experienced before, Aprils soft, yet wicked hands hard at work, it was to much for Jill to take, she finally gave in, she knew she had lost the fight anyways.

"Please, oh please, I'm cuming!" Jill's voice flooded the room, echoing off the soundproof walls, as her body thrashed about on the table. Jill's body enjoying its first orgasm in years.

Quickly a mixture of pleasure and pain raced through Jill. She had never experienced anything quite as pleasurable as that before, even in her married life, but why did it have to happen here and like this? Tears started to flow down her cheek.

April lifted her off the table into a sitting position, arms locked around her in a warm embrace.

"It's going to be all right," she whispered into Jill's ear as she caressed her back for several minutes.

"You made it though, your first time...now you," April whispered.

"No she didn't...there is still one more thing," Sergeant Adams interrupted.

"C'mon guys she been through enough for one day," April groaned.

"Well we still have to now if she's gonna play by our rules, she still seems a little rebellious," Adams interrupted again.

"Please, she hasn't been with her husband in over two years, could you guys give her a break just for today, please for me?" April groaned.

"Well...I guess so, but just for you," Adams said softly, looking at his buddy who was just nodding.

Jill tried to dry her eyes, using her running shorts. She was still trying to get over today's events.

"Well April it looks like your gonna have to pull double duty then today," Adams said.

"What ever just leave us alone so we can dress, and get ready!" April hissed.

"All right, I'll tell the guard to fetch your men," Adams said as the two men left the room, not before giving each other a high five. Adams had told Deputy Duffy about April's masterful blowjobs. So they figured Jill could wait, her husband was in for quite a stretch.

"April what the fuck just happened?" Jill whispered.

"You just went through your initiation, my dear. Welcome to the prisoner's wife's life." April said as she finally pulled down her top and skirt.

"And the double duty stuff?" Jill asked meekly.

"My guess from the bulges in their pants, I have a couple of blowjobs to perform, but I don't exactly know, every time it's different, I've had to serve them beer naked or masturbate for them, play with toys," April answered.

Jill once again looked at April in disbelief.

"And you know that three months crap, in-between visits, there's ways around that too. There is no way I'm going to make my man wait three months, I come here whenever I fucking want to. You do favors for them and they do favors for you, it's that simple," April hissed.

"Who the guards?" Jill interrupted

"Yah, guards, prison officials, cops, and who's ever there, one time they had me blow the mailman just cuz he was by, like I said it's a power thing," April hissed.

"Oh my god," Jill gasped, as April now wasn't helping her anxiety level any.

"They have this room, it's like a break room or something, but it looks like a small barroom, they drink beers and watch sports," April said.

"Do I have too?"

"Only if you want a favor from them, like I did today," April interrupted Jill.

"I'm sorry about that April, I didn't mean," Jill whispered.

"That's ok, really I've kind of got used to it over the years, sometimes it really ain't that bad," April said.

"I don't know if I can do that," Jill said nervously as she was searching for her clothes.

"Most of the time they just want a blowjob, I don't think they get them at home so often and they usually don't last that long anyways," April groaned.

Jill looked at April with a panicked look on her face.

"Oh no don't tell me," April laughed.

"Isn't that gross!" Jill groaned.

"What sucking dick or the fact that you've made it this far in life without sucking one," April jeered.

"Please April," Jill hissed.

"I'm sorry Jill, I didn't mean to make fun of yah," April said, as she was helping Jill fix her hair.

"Giving head? It really ain't that bad. It's really the one time a woman has power over the man, I mean you have his sole reason for living, right in your mouth," April said, "I can honestly say I'm looking forward to sucking that cocky young Deputies cock, I'll make him cum in thirty seconds flat and then laugh at him."

For the first time the two women shared a laugh and a hug.

"Jill Kelly, do you know you share names with a famous porno starlet?" April asked.

"Too bad it isn't me, I'd probably have my husband out of jail by know!" Jill said, as the two women once again shared a laugh.

"Look we'll get together, wait for me at my truck, it's the big black, four by four, out front. We have a little group for prisoner's wives, guess we could use one more," April said

A young guard came into the room, just as Jill finished dressing.

Jill was a little uneasy about what April meant by, get together, but she had to admit, being touched by April soft hands earlier wasn't half bad.

"Let's go ladies," he barked.

The two women skipped down the hall, but not before showing the young guard their tits, to the visitors room doorway. Jill saw her husband nervously pacing the floor. Jill's heart raced, as the door open she jumped into his arms, the two locked in a warm embrace, Jill tears flowing; she had finally made it to her man.

She had made it through the most humiliating day of her life...So Far.

Part 2. Jill joins the prisoner's wives club.

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

Her mind drifted back to 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 join their club of prisoner's wives, could she really trade sexually favors. The hot bath water was about the only thing keeping Jill calm.

Her heart raced as she remembered her first embrace with her husband, it had been over two years, 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, as they both had a lot to be sorry about their present positions in life, but they both knew 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, while her husband kissed her neck. April was down on her knees, her skirt bunch around her waist, her head in her husband lap, bobbing up and down. The young guard was only a few feet away, licking his lips, obvious enjoying the show, or maybe waiting for his turn.

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 dick in her mouth.

As she soaked, her mind roamed to the conversation with April after their session. April had told her how after her visit with her husband, she had to go into the break room and blow the sergeant and the young Deputy. She stuck a finger in her mouth and pretended that it was a dick, she had to take it out several times to stop from gagging. Just how the hell do bad girls do that? She asked herself several times.

The following week she called April several times to talk, to try to learn as much as possible to try to avoid the amount of humiliation she endured in her first visit. April invited her up to her cabin, the following Friday for the prisoners wives clubs, Friday night meeting, and then they could go by the prison and visit their men on Saturday. She agreed only after some coaxing from April.

The following week was a hectic one for Jill. She sold her house and moved into a one-room studio over the bookstore. She also was 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 spending the night at April's house. She figured it was a combination of all three, that was causing her sleepless night.

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 with knocking knees; she knocked on the cabin door.

April answered the door. The two women shared a warm embrace, as she entered the cabin. April was introduced to the other women; while the other women stood up and introduced themselves. There was Beth, an older overweight woman, Candy, a tuff looking biker chick, who could have passed for April's sister. The last woman was a sexy tall redhead, who surprised Jill by greeting her with a soft kiss on the lips.

"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 hissed, as she pushed Red away, "don't worry, Red is just a little affectionate that's all."