Prison Escape

Prison Escapee

By Katie Kulka

Chapter One - Visitation

I forced a smile as I saw my family pleasantly waiting for me, wearing their Sunday best. Meanwhile I'm wearing an orange top and matching pants, along with cloth shoes. It was visiting day at the prison, and my parents had come to see me and presumably inform me about the status of my appeal.

I'm Kimberly Reynolds, a 24-year-old who had joined in with a group of outlaws who made their money running scams, cons, and robberies. Things were good for a while. The money was great, I had a boyfriend, Sergio, who I had adored and lusted after greatly. But then things fell apart as often happens.

I had been the getaway driver for a robbery, a simple smash and grab at a jewelry store. We weren't even armed as the store didn't have a guard. The whole thing was supposed to take less than 5 minutes, I would drive us away, and then we would fence the jewelry with a buyer on the black-market Sergio knew.

But as chance would have it, a passing patrol unit nabbed me outside the store right after a clerk hit the silent alarm. Sitting outside the store in a dark sedan with the engine running, wearing a baseball cap and a mask was a dead giveaway to the cops that I was part of the robbery team. The patrol unit took me into custody while the team inside had snuck out the back and darted into the woods, narrowly escaping the authorities.

After a short stint in county jail where I had been denied bail, I had been convicted of participating in the robbery and sentenced to a number of years in prison. The actual number of years wasn't important, I wasn't really paying attention at the time. The judge had scolded me for drifting away and not paying attention to him. To say I wasn't a fan of him and his bloviating would be an understatement.

And the prosecutor was somehow even worse. He had tried to get me to turn state's evidence in exchange for probation. There was no way that I was being a rat. Not to mention the consequences if I ratted out the men that I was working with.

Rumor had it the last girl who turned state's evidence and ratted had ended up working south of the border in Tijuana. No thanks to that. I had made my bed, and I could sleep in it. I had always considered serving time upstate as a potential hazard of the life I had chosen. I just had to deal with it.

My parents, the good people that they are, had pleaded with me to take the deal, especially after the prosecutor had upped the offer to immunity and witness protection but I had steadfastly refused. I couldn't live with myself if I was a rat and I suspected that the group I had joined would find me anyway if I went into witness protection.

Even if they didn't find me, there was no way I was living out the rest of my life working the counter at Panera in Peoria, Illinois or whatever backwaters town the prosecutor would ship me off to if I agreed to testify against my accomplices, friends mind you, before getting shipped off far away.

After my conviction, my parents had hired some supposed hot-shot appeals lawyer to pursue an appeal on my behalf. I had blessed it because a pending appeal added a little bit of levity to my otherwise mundane and boring days, as nearly every day in jail was. Unless there was a fight, but the guards kept us in line. Well, most of the time.

I can still remember the last fight I was in. I ended up with a black eye and bruised ribs. But the other girl has a nose that is still crooked until she can get out and get a plastic surgeon to correct it. The time in the hole was worth it as I got to see her most days in the chow line, exercise yard, or elsewhere with the bent nose that was a direct result from my right cross.

"Hi dear," Mom said. "How are you holding up?"

"Okay," I replied with a forced smile, without offering any details.

This world was so much different than either my mom or dad could ever envision. It was best to be vague with them

"We brought a friend for you," Mom replied. Dad was as stoic as always. The friend was my high school ex-boyfriend Danny.

Danny was a nice guy, attractive, studious, and lived a few doors down in our neighborhood. I had dated him before I knew that there were other, more adventurous guys for me to meet. Danny was predictably devastated when I had broken up with him a couple of days before prom. He probably thought that I was going to show up with some other guy from our high school, but I had actually spent the night drinking in the woods with some older guys, drinking, smoking weed, and having other fun activities. You can probably imagine what.

My parents thought the world of Danny though. As they should. He's a great guy. Just not for me. From the look on his face, I could tell that they had dragged him along, hoping that me seeing him would rekindle something in me from years ago. But truth be told, I've always been like this, a schemer looking for the easy way in life.

But, unfortunately for Danny, I could also tell that at least part of him pined for me still, or at least for the girl he thought I was when we were going out in high school.

"It's good to see you Danny," I said with a smile. "What's new?"

"Started working at my dad's firm this week," he said.

"How about a girlfriend?" I asked. "You must be beating them off with a stick."

"Not quite," he replied. "I'm in between girlfriends at the moment."

"Maybe you and him could have another go when you get out," Mom offered, helpfully she thought.

"I have my own place," Danny helpfully offered.

"Yeah sure, whatever," I replied, while stroking my hair behind my ear. "Maybe you'll make an honest woman out of me yet."

It was obvious that mom wasn't going to let up on the idea of me and Danny. In her perfect world, I would be married to him by now with a bun in the oven. As if. That world just wasn't for me. Someday my parents might see that, but they hadn't yet.

"Wonderful dear," Mom exclaimed.

"Let's talk about your appeal hearing," Dad interjected.

Finally, something that wasn't about my love life. Or lack thereof.

"Yeah, sure. When is that again?" I asked.

"This upcoming Tuesday, like I told you dear," Dad replied, that I had forgotten the date.

Dad went on to explain how the judge had displayed animus against me and there was certain evidence that he had included that should have excluded. I wasn't paying attention during most of the trial, so I hadn't noticed it. Nor did I understand the first thing about courtroom procedures.

"So, what is the bottom line?" I asked once dad had finished explaining everything.

"The lawyer thinks you have a good chance to get a new trial," Dad said. "Or the charges dismissed entirely."

"That's good to hear," I replied.

Internally, I was rolling my eyes. My fellow inmates had told me appeals have a miniscule chance of succeeding. And while none of them had law degrees, they all had filed their own appeals only to see them be rejected.

It was likely that the lawyer fed my parents a load of horse manure about my appeal so that they would pay his exorbitant rate. But my parents were eternally optimistic about everything and believed everything that the lawyer said just so they would foot the money for my appeal.

"I can't wait for the appeal," I replied with a forced smile. "I'll get to be there, right?"

"Of course, dear," Mom replied. "We'll have proper clothes awaiting you at the courthouse to change into."

"That would be wonderful," I replied. "Will you be there Danny? Please? To support me?"

"Of course," Danny replied. "You know I would do anything for you."

"You're so kind, Danny," I replied, before giving him a big hug.

I gave Danny a bone-crushing hug, for a long time, until a guard called out to knock it off. Physical contact was prohibited, but not grossly so. The guards just used the rule to keep order in the visiting room.

I'm blessed with a reasonably ample bust and I'm sure Danny got a rush from me pressing my unrestrained breasts against his chest. It was a just reward for my parents dragging all the way out here to see me. Plus, I'm sure it helped to convince my parents that I was all-in on the hope of being freed via my lawyer's appeal.

Plus, I didn't mind the feeling of being pressed up against a free man, while his masculine scent infiltrated my nostrils. As an added bonus, Danny's dick was erect and pressing up against my stomach as we hugged. It provided a jolt of confidence that knowing after all these years and everything that Danny still carried a torch for me.

"I should get going," I said, once I broke the hug with Danny. "It's mealtime soon."

"You'll be out soon dear," Mom said.

"And I'll be waiting for you Kimberly," Danny said.

I'm not sure if he was saying that or if he actually harbored hopes of us being together. I did wish he would find someone else to date, marry, and have a family with. A guy like him deserved a good girl to dote over him. Not someone like me who was devoted to a life of crimes and scheming. But he was going to have to come to that realization himself.

Chapter Two - Guard Gentry

I winked back and waived at my parents and Danny, as I arched my back, giving Danny a good look at my ass, before exiting the visiting room, where I entered the room where we would be processed back into the general population. Guard Gentry was working the desk today.

Gentry was a homely man, 5'8" with a shaved head to mask a receding hair line, pot belly, and his left arm was completely covered in tattoos as he thought it made him look tough. Even though it didn't.

I stood there before Guard Gentry as he processed me back into the general population. First, he had to scan my wristband before the unpleasant part. One that I had grown accustomed to by now.

"Turn and drop your pants, Reynolds," Gentry said without looking up as he completed the paperwork.

I sighed and did as he directed, dropping my prison issue pants along with my white cotton panties to my ankles. The cavity search was a necessary but unenviable part of returning to my cell. The jail would have preferred to have a female guard do it, but they were in short supply and apparently Gentry drew the duty today. Rumor had it some of the male guards gambled amongst themselves for the duty. I bent over slightly at the waist to give Gentry easy access to my pussy and anal cavity. The sooner this was over, the better.

I smirked as Gentry inserted a gloved finger inside of me, probing my pussy before slipping his finger in my ass to check for contraband. Of course, I didn't have any. The good stuff was smuggled in through other means, but the guards had their protocols to follow.

I pushed back into Gentry's finger when he lingered inside of my anus a little bit more than was necessary. I was no stranger to having things in my bum, as Sergio used to fuck my ass often. To say I missed that man, his glorious cock, and getting seeded with the prodigious cum loads he produced would be an understatement.

"You're all good Reynolds," Gentry said, after withdrawing his finger and disposing the glove in the trash can. The number of gloves in the trash can indicated how many inspections that he had performed already today. I'm sure lots of guys would love Gentry's gig, even if many of the girls in here weren't exactly billboard material.

I pulled my pants and panties back up and waited for Gentry to buzz the door open. When the big metal door opened, I walked through it. The door closed behind me with a loud thud. It was still the middle of the day and the general areas were open, but I decided to make my way back to my cell.

My cellmate Tiana was there, splayed out on the bottom bunk, watching television, although the channels we got were shit. Tiana was in here, like so many others, after getting collared from drug related offense or another. I forget exactly. The details weren't all that important.

Tiana is gorgeous though. Tall at 5'9", dark curly hair, full, firm breasts, luscious lips, a curvy body, and gorgeous caramel skin that somehow doesn't have one blemish despite not having access to a good skin care routine.

"Good news girl?" Tiana asked.

"Family filed an appeal on my behalf, but it's bogus," I replied, sitting down next to her. "They all are."

The bottom bunk was mine, but we used it as a makeshift couch during the day to hang out and watch television together or just chat and gossip.

"You can't think that way girl," Tiana objected. "Who knows what some dumb judge might think."

"Unless he fell on his head that morning, there is no way my conviction is getting overturned," I replied glumly.

"All the better for me," Tiana said. "Means I don't need to break in a new cellmate anytime soon."

I smirked back at her. Tiana was one of the bright spots in this place.

"Reynolds," Gentry called out.

I sighed and looked up at him. He must have gotten relieved from fingering duty, as I called it, shortly after I was admitted back into the general population.

"Yes Sir?" I asked, raising my eyebrows and rolling my eyes as looked up at him.

"Come with me, now," Gentry said.

What sucked about prison life, besides the obvious, was that the guards never had to give a reason for anything. It was like playing Simon Says, but without a winner. I sighed and stood up. There was no objecting unless I wanted to get written up and maybe end up in solitary.

"Busted," Tiana playfully called out as I walked out of the cell, only to have Gentry grab me by the upper arm and roughly escort me down the hall, parading me past the cell block.

A few minutes later, we ended up near an interview room, the kind that the prisoners were permitted with their lawyers. There would be no prying cameras in these rooms.

"Inside," Gentry said, using a key to open the door.

I didn't have much of a choice as he roughly escorted me inside the cell by pushing on my back, forcing me in. Like always, the guards, especially Gentry, liked to assert their physical dominance over the inmates. For Gentry it was probably because he got his ass kicked playing football way back when and needed some outlet for his aggression and a way to validate his masculinity.

Chapter Three - Interrogation

Guard Gentry followed me in the secluded room and pounced. A mere second or two after he closed and locked the door, he was forcing his tongue down my throat before pulling off my prison issue top which soon fell to the floor, exposing my unsupported tits. He quickly wiggled me out of the pants, leaving me standing there in nothing but my white cotton panties.

Despite not being the most imposing man, Gentry was much bigger than my 5'4", 120 pound frame. He lewdly and roughly rubbed his hands all over my body.

"I've missed you so much," Gentry whispered in my ear. "I love your hot body."

"I thought you were going to take me over your desk just a bit ago," I whispered back. "I was so horny when you were fingering me."

"You want my big dick babe?" Gentry asked.

"More than anything," I moaned back as I ran my hands over Gentry's body, focusing on groping my tight ass.

"Suck it Reynolds, like a good girl," Gentry said.

I smiled coyly, before sinking to my knees. Gentry, like all the guards, was wearing a standard issue guard suit, complete with a button-down shirt, blue pants, a belt, and a nightstick that was far more impressive than anything in his pants.

Nevertheless, I pulled open his belt and his fly. Like always, Gentry's manhood was straining against his pants. He was wearing briefs today, like usual, although they weren't white this time, thankfully. I'll never know what fashion designer thought that white briefs were a good look for men.

His dick flopped out when I pulled his briefs. Gentry's dick was average at best and his pubic hair was ungroomed, like always. I guess there was no reason to groom your pubic hair when you had a sure thing locked up. Quite literally. I doubt Gentry even chased after girls on the outside anymore now that he had me to orally service him at his discretion.

I quickly engulfed his dick with my mouth, sucking on it, like I had many times before. Gentry had a firm grasp of my hair, forcing me down on his dick. I made a show of gagging on it, but accommodating his member was easy, especially compared to many, even most, of the men that I had sucked off.

As I worked his dick like a runway model, Gentry groans grew louder and louder. He did his best to stifle them, but I doubted that anyone could hear us in this room anyway.

What Gentry and I were doing was against the rules obviously, but I doubted Gentry was the only guard who flouted this particular rule, although no one talked about it for fear of getting found out.

A couple of months back, shortly after I become accustomed to being an involuntary resident of this institution, I had seduced Gentry. It wasn't hard because I could tell from his mannerisms that he had the hots for me.

Despite Gentry knowing how wrong it was, he easily gave in to my advances, and we had partaken in quite a number of clandestine sexual rendezvous since. Once or twice, we had almost gotten caught, but to date it hadn't happened, thankfully.

"I want you to fuck me stud," I moaned as I took my mouth off of his dick momentarily, as I looked up at him, while stroking his dick.

"Don't got a rubber today, Kimberly," Gentry said. "Your mouth feels too good anyway. Swallow my seed like a good girl."

I had to physically stop myself from audibly sighing. My pussy was begging for attention. I was near the peak of my fertility cycle and fucking horny as hell. That combined with not getting cum in my pussy for seemingly forever had me positively feral.

"I love how your dick tastes," I seductively replied, once I collected myself, before sucking on his dick once again, easily deepthroating it as I massaged his hairy testicles, which unlike his cock were huge.

Guard Gentry was a rulebreaker, but he wasn't stupid. No guard in their right mind would fuck a con bareback. If I got pregnant or saved any of his seed and told on Gentry, it would mean losing his job among many other consequences. All of them bad. Very bad. And very serious.

As I continued slurping on Gentry's dick, I knew he was close. Both from his audible groans growing higher pitched and that he had taken a firm grasp of my head holding on tightly with his fingers.

Less than a minute later, Gentry groaned loudly as his dick twitched on my tongue and cum spurted into my mouth, coating my tongue and hitting the back of my throat. The taste was sour like always, owing to his presumed diet of fatty foods, diet colas, and brown liquor. I made a huge show of swallowing it like always, pretending that it tasted good.

"You were incredible as always," Gentry said, caressing my cheek.

"I love sucking your dick," I replied looking up at him with a smile. "I can't wait until I can do it everyday."

"In time babe," Gentry said.

I stood up and pressed my curvy body into Gentry's plump frame and rested my hand on his chest.

"You just got to tell me the plans on Tuesday and I will be yours forever," I pleaded with longing eyes.

"The van will leave at 10 am," Gentry said. "At mile marker 380 a group of men will jump the van and whisk you off to my cabin in the woods. I'll meet you there once the hoopla dies down."

Gentry had previously told me about a cabin he owned, deep in the woods that his great-uncle had left him. As of right now Gentry was 54 and near the state-mandated retirement age of 54 for guards. The plan was for me to hide out in his cabin, while Gentry worked his last few months on the job. After that his plan was to retire, hunt, fish, and have a sexy girlfriend, aka me, take care of the place and be sexually available.

Gentry had previously worked in a men's correctional institution and retained connections with a few ex-cons who were supposed to bust me out in exchange for an apparently significant fee. And Gentry apparently had a bunch of money saved up from years of working overtime along with not having a wife and family to support.