Jill Kelly Goes To Prison Ch. 3

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Jill goes back to prison for more humiliation.
5.6k words
4.31
140.1k
16

Part 2 of the 5 part series

Updated 10/10/2022
Created 02/20/2002
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Jill tossed and turned in her sleep all night, she had just lived through a long day and she knew she had another long one in front of her. She shifted between a light sleep and periods of being wide awake. When she slept, she seemed to only dream about April licking her pussy. She kept asking herself, What did this mean? Did she really want April to do it, or was she fearful that she would?

Jill was somewhat surprised when April woke her up and told her to hurry up and take a shower and dress, that they all had to leave for the prison soon. It felt like Jill hadn't slept at all, she was still having a little trouble separating reality from her dreams.

Jill showered while April laid out her clothes, the same ones from yesterday and also gave her some coconut body lotion to put on. After the shower and her rub down. Jill noticed that Red and Candy were hanging out in the kitchen, dressed in really sexy outfits. For the next hour they helped Jill with her hair and make up, because they wanted her to look just right, on the other hand Jill's mind kept wandering back to the vision of them using the strap-on, last night, but she never dared asked them about it.

April bounced into the room and announced that she was ready and the four of them left the cabin and headed for the prison. Candy rode her Harley, while the other three women went in April's four by four. They arrived at the prison just after one in the afternoon. They wanted to let the families clear out, as families were allowed visits only on Saturday mornings.

They checked in and sauntered into the waiting room and quickly noticed three teen-aged boys sitting there, they looked kind of young, but they knew that they were at least 18, because the prison didn't allow anyone under 18 in the prison after noontime. The three boys were sitting next to an older woman, who they guessed was their mom. The four women took some seats on the opposite side of the small waiting room.

"If their eyes get any wider there going to pop out of their head," April purred.

"Shhh..." Jill hissed.

"Hey! I think the big one is looking up my dress," Red moaned.

"Oh my god close your legs," Jill hissed.

She saw that Red had her legs spread apart, her small dress was riding up her thighs, and she knew that Red didn't have panties on, in fact none of them did. Her own leather skirt was just as short, but at least she used her hand and arm to block their view. She watched as Red put her arms behind her back and the back of Candy, who was sitting on the other side, this pulled her already tight dress even tighter and higher. Jill let out a small gasp when she looked at the three boy's lustful expressions.

"C'mon Red quit it!" Jill moaned.

"What they want to look, I'm just giving them something to look at," Red purred.

While Jill tried her best to cover up, all three of the other girls took their little turns teasing the boys, a move here a move there. April even bent down to retie Red's boot, giving the boys an eye full of her deep cleavage, while Red also bent down to assist her, Red's left breast somehow escaping from it's hiding place. Their teasing of the boys went on for ten minutes until a guard came in and motioned for them to follow him.

"C'mon boys," the older woman with the boys barked, as she slapped the oldest looking boy on the back of the head.

"You girls should be ashamed of yourselves," she hissed, as she walked by, as she was a little more aware of what had happened then she had let on, as it happened.

Jill was mortified, but the other three women all laughed, they just felt like they had some harmless fun teasing the young men. After a half an hour the guard came back and got the four women.

"Hey dude where's Sergeant Adams?" April asked the guard.

"It's Correctional Officer Lincoln," he barked.

"Sorry!" April moaned.

"Well, he is at his son's little football game, if you must know, but the wardens still around," he mumbled.

April and Jill were led into the break room, slash bar room, while Red and Candy were led into the processing room for their search. Jill asked Officer Lincoln if they could all be searched together, but he said that April and Jill would have to wait, until the other girls half-hour was over, he also said it rather rudely.

"Jill just relax Sergeant Adams isn't even here today, so you lucked out, I don't know that guard, I think he is new, just flip your skirt up and then pull your top up and we should be all set." April said.

"Oh yah no sweat," Jill said sarcastically.

After many nervous minutes, the door suddenly opened and a burly guard entered followed by an older gentleman, who walked with a cane and a limp.

"Whatever happens don't touch the wardens cane," April whispered into Jill's ear.

Jill looked over at the warden, he was really old and frail looking. She figured he was in his late 70's or even 80's, but somehow he still sent a shiver down her back, just by the way he was looking at them. Jill was ever so nervous when he called the two of them over to the pool table and had them stand side by side.

"My name is Warden Johnson," the old man groaned in a gravelly voice.

"I have seen this one around before," he said pointing at April. "But you, you must be relatively new." he said now pointing at Jill with his cane.

"This is Jill Kelly, her husband is prisoner 5689-ds. He is in for drug smuggling, 10-12 years," the burly guard rambled, reading from his clipboard.

"A God dammed drug smuggler," the warden hissed, as Jill looked down ashamed, only to have the wardens cane lift her head back up. He went on to tell them a rambling speech about the early years, when he was in his prime. He told them about his iron fist, and finally how God had nothing over him. Jill got the sense that he had enjoyed his years and his power as the warden, and it seemed like some the guards were following in his footsteps.

"I still can't understand how some convicts could have such good-looking women," the warden hissed.

He used his cane to run it along Jill's shoulder and then it traveled down her breast. It was all Jill could do to not bat the cruel thing away from her, it rubbed her nipple repeatedly, before he motioned for her turn around, her legs felt numb as she turned around. She felt the cane under her skirt and then it lifted up. She was mortified that the old warden would do this to her, as he was now looking at her exposed pussy and ass from behind.

She felt the wardens cane on her back, pushing her forward, she reluctantly leaned over and put her hands and shoulders on the pool table. The warden then turned his attention to April, who after a quick inspection soon found herself in the same position as Jill.

The guard came back in, inadvertently breaking up the action, he announced that he wanted to search the women now, but the warden said they were clean and that they could see their husbands now, much too the disappointment of the guard, who left muttering to himself.

The two women adjusted their clothing and the burly guard said he would take them into the visiting room.

"Wow this is your luck day," April purred, but Jill was somewhat a little shaken from the wardens cane assault, plus she personally didn't feel real lucky.

Jill's husband was surprised to see her at first, they didn't even tell him she was coming, but he was defiantly more surprised by the way she was dressed and the way her hair and her make up was done.

"Wow honey you look so...different," Jill's husband Bob mumbled.

"Do you like it?" Jill asked nervously after the two had shared a long embrace.

"Yah, it's just, you know different," Bob managed a little stunned at his wife's transformation.

"My new friend April over there has been helping me with my hair and make up and some other things," Jill said looking at April.

They both noticed that April was already giving her husband oral sex.

"That's your new friend!" Bob said, a little stunned.

"Is she supposed to be doing that?" he whispered.

Jill was really too nervous and embarrassed to answer, she just hugged him for several minutes and tried to gather her strength, she looked down into his lap and noticed his groin was stirring.

"Bob would you...Want me to do that to you?" Jill whispered in his ear, barley able to get the words out.

"What the fuck has gotten into you?" Bob fired back.

"Please don't be mad, it's just, I felt so bad leaving you all excited last time, and I noticed that you were getting a little turned on," Jill said, as she stroked her husband's hair.

"Well it's just been so long, but baby," Bob moaned.

"I know honey that's why I'm making the offer, I would love to make love to you instead, I just didn't know if they allow that," Jill said while kissing Bob.

"But..." Bob started before being cut of by his wife's lips.

"Trust me for once," she purred.

Jill spent some time kissing her husband before moving down his body, and was now kneeling in front of him. She tried to hide under the table as much as possible. She pulled her husbands now erect cock out of his prison pants and began to stroke it, at first she just licked the head with her tongue, and then ran it down the shaft several times before finally getting over her fears of putting it in her mouth.

She tried to remember the lessons from the night before. She began moving her head up and down, she looked up at her husband who had a shocked look on his face. She was thankful that the guard was more interested in April's blowjob than hers. She was fighting her gag reflex and applying more pressure. Her husband couldn't hold out long and blasted a shot of cum into her mouth. The first blast caught Jill by surprise as she almost forgot about that part, and then she swallowed most of it down. She used some paper towels that were on the table to clean the rest off.

"All in all it wasn't that bad," she thought. She was glad for one thing that if she had to suck dick at least the first dick she sucked was her husbands and not some piece of shit guards. She still didn't know how she was going to handle that.

The guard took away their husbands and the two women cleaned up in the women's room. They giggled away like two schoolgirls as Jill told her story to April. Jill felt a strange sense of pride as she had conquered her fear, while also pleasuring her husband. As they were leaving the room the guard that had been denied his strip search by the warden stopped the girls.

"Hey you aren't leaving yet, I enjoyed your little show Jill, but really hiding under the table. C'mon into the break room and show me what you were hiding," he said grabbing Jill by the arm.

"Hey asshole, you're hurting me," Jill cried.

"Yah back off, she's with me!" April barked, as she freed Jill from the guard's grasp.

"Yah well Sergeant Adams ain't here to protect your sweet ass, so you can get in there too, big tits," the guard barked, as he blocked their path.

"You'll get out of our way if you know what is good for yah!" April hissed, as the two women stared the guard down.

"Hey Lincoln is there a problem here," a voice boomed off the hall walls.

The two girls saw the young Deputy from their last visit, standing in the hallway.

"No, no problem Deputy Duffy, just having a little fun with the ladies," the guard said.

"Right, April come over here," Duffy barked.

April gave the angry guard the finger and then grabbed Jill's wrist and they scampered down the hall. As they chatted Deputy Duffy walked the two women to the parking lot. The two were glad that he had showed up when he did. Lucky, he had to drop off a convict that had left his work release program on Friday and he had just caught him. They stopped by his police car and April gave the young Deputy her phone number and address.

"What was that all about April," Jill asked as they walked over to her truck.

"C'mon Jill haven't you learned that in there, no good deed goes un-rewarded," April hissed.

Jill didn't even have time to think about that as she noticed Red leaning against April's truck and she was talking to one of the teenaged boys that they had teased earlier.

"Hey! What did you do to her?" April barked, as they noticed that Red was crying.

"Please April he didn't do anything," Red mumbled, trying to regain her composer. The young man seemed to panic and hopped into an old sports car and sped off.

"Red what the fucks going on?" Jill barked.

"Please, let just go, I'll tell you on the way home," she moaned, as they climbed into the truck. On the ride home Red told them her story.

"The young man was waiting for us at the truck and well I was the first one out. Well I asked him what he wanted, and well at first he though we were all like strippers or more. I wasn't real surprised since the show we put on for them, and the way we were dressed, but then he got all serious and had a hard time talking, he was even chocking up a bit, so I knew it must have been serious. Then he told me about his cousin, he was the skinny one with the ball hat. Well...He has cancer and it's gotten to the point were there nothing else they can do for him," Red mumbled.

"Aw that's terrible, but why did he want to tell us?" April asked, as Jill was thinking the same thing.

"Well Ok, but don't laugh, well tonight's his cousin's 19th birthday and he wanted to know if we would come," Red said.

"Really, cake and ice cream with mom and dad?" April said with a laugh.

"I told you not to laugh, I was getting to it, he wanted to know if we would strip for his cousin, at the party?"

"I hope you told him that we weren't strippers." Jill barked.

"I did and that's where the, more, thing comes into effect. He said that while his cousin didn't fear dying, well he just didn't want to die a virgin." Red moaned, as the truck erupted in a chorus of skepticism and criticism from the two other women.

"Let me finish, he said that they had talked a girl from school to do it, but she backed out at the last minute, he said that the guy's older sister was even willing to do it, but they were trying to do anything to avoid that. He even gave me $247.00 that they raised for the girl.

"Red tell me you didn't take it?" April barked.

"Yah," Red said while showing them the money, which was followed by more yelling from the women which lasted until they finally got back to April's cabin.

"I have to make a phone call, this sounds like some BS story. I know someone who works at the hospital. Give me that!" April barked as she grabbed the paper that had the name and address of his Uncle's house where the party was.

For the next hour April made several phone calls, while Red and Jill paced in the living room. Finally April came into the living room, her eyes glassy.

"I guess the guys story about his cousin checks out, their parents have racked up quite a large hospital bill, my friend even gave me the doctors number, and when I finally got him, he said that there was nothing they could do for him now, it spread too far." April said before she burst into tears and ran into the bathroom.

"Jill I guess there is something you should know about April," Red whispered, as Jill looked at her with dripping eyes, "April lost both of her parents from cancer when she was younger."

That was the last straw for Jill as she too broke down. For the next several hours Red tried to comfort the two women, although April had locked herself in the bathroom, and Jill would just bat her away. Finally the bathroom door swung open an April marched into the living room.

"What are you two doing, let's get ready, we have a birthday party to attend," she barked.

Jill looked up at April with a shocked face.

"April you can't be serious," she mumbled.

"What, hey if you don't want to go, there is the fucking door, just don't ever come fucking back!" April barked before she marched into the bedroom.

Jill sat in stunned silence for several minutes, she had experienced a lot in a short time, but this was too much. She raced to the door, but for several more minutes, she just couldn't open it. April had become her new emotional pillar. She just didn't think she could make it anymore without April in her life. She even laughed to herself nervously. If I'm stripping with those two, who is going to be looking at me? And if the young man were going to pick one of use to have sex with after, surly he wouldn't pick me.

Jill went back and opened the bedroom door, the two women looked up and smiled, before they both gave her a big hug. After some time to regain their composer, April and Red announced that they were going to show Jill how to dress for the occasion. First they dressed Jill in a sexy black underwear, and then with a short black shirt and a white silk blouse, and stripper like high-heels. While the other two women wore sexy full-length gowns over their sexy underwear. They also grabbed sexy fur jackets. Jill wondered where April got all the nice clothes, but she figured this wasn't the time or place to ask, she also remembered her husband was in prison for theft.

The women followed the directions on the note and pulled up to a large farmhouse. The house was well lit up and there were several cars and trucks parked around.

"Well fellow strippers are we ready?" April moaned as they approached the house. Jill still felt anything but ready. The front door opened and the young man that they saw Red talking with bounced out.

"Wow thank God you girls really came, I told them you would, but they didn't believe me," he bellowed.

"Who is them and they," Jill quickly asked.

"Oh, I told Billy, that my cousin and his older sister Wendy, and I had to tell his parents, but that's it," the young man moaned.

"And his parents didn't have a problem with the whole thing," Jill asked skeptically.

"First, they just said Danny, that's me, you're full of shit like you always are, but finally after several tries, they said under the circumstances it would be all right," he mumbled, "come on in."

The three women enter the kitchen and stopped dead in their tracts, they had expected a room full of horny teenaged boys, but instead they had walked into a family party, people of all ages and mixed sexes, each one now giving them quizzical looks.

"Oh you must be Billy's school friends," an older woman said.

"Ah yes I guess," April moaned more than a little embarrassed, while Danny was busy talking to Billy.

"Here girls have some cake and ice cream," the older women said handing them some plates. The women looked at either other and broke out laughing as they remembered April's comments in the truck, when she first heard of the party.

April kept motioning for Danny to come back over and he finally got the hint.

"Danny I hope you don't think we are doing this here, in front of them!" April hissed.

"Oh no," Danny laughed, "I was thinking more like in Billy's room, and just for him, and well if I could watch too, that be it."

"Ok, but now if you could show us his room, I mean this is more than a little uncomfortable for us," April said.

"What you don't like my Aunt's cake either," he laughed, although he laughed alone.

"All right follow me, hopefully the party should be breaking up real soon," Danny said as the women quickly followed.

The three women nervously waited in Billy's bedroom, for the next half-hour, as Red took the time to explore the young man's room.

"Look guys a dirty magazine, Juggs, this is a sleazy one," Red purred.

"C'mon Red," Jill groaned as she sat in nervous tension.

"Good he has little boom box, and some CD's. I don't know how we forgot about music, cool he has the new Motley Crue CD." Red purred.

Finally, the bedroom door opened and Danny walked in with a plain looking brunette.

"Girls this is Wendy, she's Billy's older sister," Danny said.

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