A Halloween Prisoner Pt 02

Allison led Jennifer by her leash out of the door, into her New York apartment building hallway. Jennifer suddenly felt extremely exposed now she was out in the open, even though there was no one to be seen thus far.

"Follow me inmate, the car is in the garage," said Allison as she tugged on her leash, walking towards the elevator. Jennifer felt her eyes dart left and right, just paranoid one of her neighbors would walk out and see her like this. Her hands were still handcuffed to her waist chain, and her orange bit gag was tightly clamped in her mouth. On one hand, no one would think she was an actual prisoner given how crazy her costume was. On another... she was right now handcuffed, gagged in a hallway, wearing just panties waist down, and had a hanging paddle.

The elevator dinged and the doors opened. Jennifer's eyes widened all the way as she saw two young guys in the elevator. One was holding a Nintendo switch and the other was on his phone, but it took just a second or two before they looked up and had their jaws drop.

Allison smiled as she pulled Jennifer into the elevator behind her.

"Hey boys, want to meet my prisoner?" she said energetically, as Jennifer was pulled in and the doors shut behind them. It was obvious that both of them were in complete shock at what they were looking at, and Jennifer could see the one farthest from her staring directly at her prisoner panties.

"Um, wow.. that's quite a costume. Where did you get it?" stammered the first one.

Before answering, Allison pushed the button to the car garage. These boys were getting off in the lobby.

"Me? Well I made mine. My prisoner here got hers issued when she was arrested," said Allison. Jennifer grunted into the gag, to almost acknowledge the joke. Her pussy was so wet now, and she was scared they would notice.

"That's..." said the first one.

"Can I get a picture with you girls?" cut in the second one.

The elevator was still going down. It's fairly slow, and there were 23 stories to go.

"Well, unfortunately cops aren't allowed to take pictures with fans, but you are more than welcome to take a picture with Inmate 298192 here," said Allison. "Have a phone?"

Jennifer shook her head. Wow, was Allison really going to humiliate her like this? She regretted not believing in her ability to choose a good Halloween costume.

"Yes, of course," said the young guy in a giddy tone, passing a phone from his pocket to Allison, and then turning to his friend, "Wanna get in on this?"

Elevator was around floor 14 now. Jennifer decided to not fight this, as both boys flanked her sides and Allison stood on the opposite side of the elevator. Then she decided to unclip one of her remaining sets of handcuffs, pass it to the guy on the left and said, "Why don't you twirl this as a prop as if you just arrested this naughty girl."

Grinning, he took the handcuffs set. Allison then turned to the other boy.

"And you, you got a name?" asked Allison.

"Uh, Roger, offic- ma'am," he said. Allison smiled at Roger's instinct to call her officer. Jennifer thought Allison must feel really good about herself. Then Allison said something that would have made Jennifer's jaw drop if it wasn't already forced open by her bit gag.

"Great. Grab that paddle hanging from her belt and make it look like you are giving her a nice spanking. In my jail, we spank our inmates since they are naughty girls."

Roger laughing said, "Ok, you are the boss warden."

Jennifer grunted into the gag. She felt so wet but so humiliated at the same time.

"Say 'Jail!'" motioned Allison. Both boys said it in unison, with Jennifer chiming in haphazardly, only to remember she was gagged. The camera had flash enabled and Allison shot the picture.

At the same time, the elevator doors opened to the lobby, and a group of drunk girls outside were about to get in, only to see what was happening. You can tell they were about to howl in laughter, and the boys, not wanting to catch a scene, quickly returned the props to Allison, received their phone, and thanked her for the opportunity.

They jumped out. Meanwhile, one of the girls giggling looked at Allison and said, "are you going up?"

Allison smiled and said: "Nope, going down to lock up my inmate." The doors closed.

Jennifer wanted to scream at Allison, to which she yelled but only muffled noises came out. That was easily the fastest her heart had ever beat. And the fact that those guys had a picture of her like this? With one spanking her? She knew they were going to be masterbating to that picture for the rest of time.

Allison laughed and said, "Look convict, you are going to have quite the night, I will tell you that."

Jennifer wanted to squirm inside. This night had already been eventful as ever. Could it get any worse? The elevator doors opened and they were able to walk (or in Jennifer's case, hobble) outside of the elevator. Jennifer looked for Allison's car, and spied it to the left. It looked normal - at this stage she expected it to even be a police cruiser.

Allison led Jennifer by her leash towards her car, and unlocked it with her keys. Jennifer naturally motioned to move around the front to get into the passenger seat, but then Allison abruptly tugged her in the other direction.

"Nuh uh uh, prisoners are transported in the back, not the front. C'mon, silly," teased Allison. Jennifer rolled her eyes. Of course. Allison didn't seem amused and retorted, "Do I need to spank you for that eye roll, inmate?"

Jennifer vigorously shook her head no.

"Good," said Allison. She opened the passenger door and helped Jennifer get inside.

Wow. While the exterior of the car was no different, Allison had taken some type of mesh, like one of those locker bookshelf things, and partitioned the front of the car from the back. She essentially had made a 'police car feel' in the back. To add to the wildness, Allison had printed out a piece of paper outlining all of the rules of her prison and affixed it to the back of her drivers seat.

It read:

Inmates must be restrained by default, and must be monitored when free.

Any major infractions lead to a spanking. A spanker may be hung by the inmate's side for easy access.

Inmates may wear clothing establishing their guilt prior to a guilty verdict being reached. This helps remind them of what may be ahead. If a guilty verdict is reached, the inmate is mandated to have the word GUILTY visibly on their uniform.

This girl was something else. How did she underestimate her? #3 was also a bit specific, oddly. Maybe a bit too semantic?

Allison got into the driver's seat and turned on the car. Immediately the sound system came on, and it became clear she had downloaded some fake police radar noises and had it playing via an aux cable or something like that. A+ for immersion, F- for being gagged, cuffed, and dressed like a prison slut.

As Allison started to pull out of the driveway, she said: "By the way, we aren't going to the party just yet, we have to make a stop."

A stop?? Jennifer muffled something into her gag in confusion. What was Allison now planning. Could it be any more torture?

"Haha, I figured you would be confused, inmate," said Allison, as she pulled out of Jennifer's apartment complex's garage. "But you were just arrested. Your clothing may say guilty, but if you paid attention to rule #3, you still need to stand trial. So on the way to the courthouse."

Jennifer again tried to say something against her gag. The courthouse? Surely Allison wouldn't bring her into the actual courthouse. It couldn't possibly be open at this hour. What on earth was she talking about? Was Allison trying to be vague?

"Oh don't worry, inmate," said Allison, "I am sure Judge Hopperfield will not be too strict on you."

OMG. She didn't mean an actual courthouse. She meant something way worse: Hopperfield was Amy Hopperfield's last name, her sorority little from college. Jennifer wasn't the best big and definitely put her little through some torture in college but didn't ever reciprocate the love back after pledging finished. And Amy definitely couldn't see her like this. What on earth is happening.

"That's right Jennifer, I got a whole night planned for ya," smiled Allison, breaking the 4th wall in a rare occurrence. She then returned back to character: "All inmates need to stand trial."

10 minutes later, in a rather uneventful car ride, save Jennifer's progressively dripping pussy, they pulled up to what was presumably Amy's walkup residence. Allison parked the car, went back, and opened the door and helped Jennifer get out. For the first time, she also pulled out a walkie talkie from her bag and spoke into it: "Copy 1 2 3, have arrived with the prisoner."

Allison then walked behind Jennifer. To her surprise, she grabbed her pussy and rubbed it, letting the sweet sensation of her touch ripple across her body. She then whispered into Jennifer's ear: "Remember what collar you are wearing. I am going to take off the gag, but I expect you to not speak a single word unless instructed by me. Not a single word. Understood?"

Jennifer nodded. Anything to take the gag off, even if she was still silenced. Allison unbuckled the gag from the back of her head and pulled it off, slipping it into her bag. She then helped Jennifer climb up the stairs and then knocked on the door.

Moments later, Amy opened the door, in her radiant beauty wearing a realistic looking judge's robe while clutching a gavel, and started howling with laughter.

"Oh my god, Allison, sorry, hahah, Officer Allison, what.. Wow Jennifer,.. What have you gotten into," started Amy. Jennifer could feel Allison lightly spank her butt as a harsh reminder of what she just said about being quiet. Amy, after realizing Jennifer was being compliant, got into character and said: "Ah right, you have your inmate in check. Great. Please, come in so we can get this trial done."

Allison, with that cue, led Jennifer in from her leash, Jennifer staying quiet to avoid getting stung by her shock collar. To her partial surprise, as it was becoming increasingly clear that Allison had gone all out, she saw that Amy had cleared out her living room and there was a makeshift court.

At the end was a nice, wooden chair, slightly elevated above the rest. This was obviously the judge's seat. In the middle, was a desk with a metal loop in the center with a handcuff attached to it. It had a chair behind it, presumably the chair of the defendant. There was also a witness stand to the left of the judge.

Allison had Jennifer sit down. She was still processing this woman had the time to set up a fake trial. And she was treating her like a real prisoner! Well, if being a real prisoner meant being paraded around in a skimpy, skin tight outfit.

She attached the handcuff on the desk to the chain of her cuffs around her hands, releasing the cuffed hands from the waist chain. Essentially, she was just as bound, but now her hands were affixed to the desk.

As if on cue, Amy sat on her judges chair, pretended to be all officially and smug, and Allison stood next to Jennifer. Amy then looked at Jennifer and comedically banged her gavel on a little podium next to her chair. This was a makeshift courthouse, to say the least, but they had definitely tried a lot.

"Order, order in the court," said Amy, to what was otherwise a silent room. Then smiling, she looked at Jennifer and said, "Inmate, you have the option to plead guilty and receive a punishment of 100 intense spankings. How do you plead."

Not thinking twice, and remembering the beating her ass got just moments ago, Jennifer immediately replied: "Um, Amy, I am innoce-."

"Excuse me, it is Your Honor," interrupted Amy, sternly.

Jennifer was wide eyed. Oh dear. Amy wasn't playing, was she? Jennifer continued: "Sorry, your honor, I am innocent. This is all a mistake." She was trying to play along.

"Very well, I do call the first witness, your arresting officer Allison," said Amy, officially and with gravitas.

With that cue, Allison walked up to the witness stand and said, "I will say the truth, truth, truth, you know, the truth thing." Jennifer laughed - with all the effort she put in, she didn't clearly care about the oath. In return, Allison shot her a half judging look.

Amy said, "Great, and what is your testimony, Officer Allison."

Allison cleared her throat. "I have found the inmate to have impersonated the sorority president's signature to approve of new pledging techniques with the charter."

OMG. Jennifer was blown away. How did Amy find out that the hazing and pledging techniques were her idea? It was something only between her and Maddy, who was her partner in crime (oh wow, that's funny now) in college. And yes, they faked a signature of the sorority president approving of these things, since the sorority president was relatively checked out.

Wow. Now Jennifer was terrified. She had made Amy do some really embarrassing stuff, including wearing her panties, from the day before, over her head every time she watched TV in the sorority house. She even made her streak and fetch the mail naked 3 times, once even when the neighboring fraternity brothers were on their lawns. Oh dear. Oh, oh dear. Jennifer had blamed all of this on "standard procedure" that the sorority had had, she had hidden it was her idea all along.

"I object!" yelled Jennifer," there is NO PROOF of that AT ALL!" She wished she could hold her hands up to object physically, but they were still locked to the desk.

"Order, order in the court," yelled Amy, now trying to hide a smile. She then looked at Allison and said, "I am afraid Officer Allison, that while your testimony is troubling, I cannot convict if you are the sole witness."

Oh Hooray, thought Jennifer. This whole thing was a set up. She was about to be freed, or at least go to this party in a more normal costume. Maybe they would give her pants and take off the cuffs. She was so relieved.

"That's fair," replied Allison, looking gloomy. She then looked up and smiled, an evil and cunning smile that Jennifer knew a thousand times over: "So as a result, I would like to call my SURPRISE WITNESS."

Wait? Surprise witness. Jennifer's heart sank. She wasn't free after all. Who was Allison referring to in the first place? She turned to the right where Allison pulled someone originally hidden in a partitioned off side of the room. She hadn't even noticed that before.

Jennifer didn't have her gag in now, and as a result, her jaw actually dropped. Oh my god. It was Maddy. And not just Maddy walking in casually. She was in a full prisoner costume too. Maddy was a beautiful, blonde woman with amazing eyes and fair cheeks. She was tall, had D sized breasts, and an incredibly toned ass. But while Jennifer had seen Maddy before - what was both stunning and sexy as hell was her costume.

Just like Jennifer, she prison orange panties on, with GUILTY stamped across her crotch. There was a mirror in the far corner behind her, so she could see it was the same uniformed panties as hers, with PRISONER on her ass, and the numerals 298191 as her prisoner number. Looks like in Allison's fictitious universe, she was the prisoner booked right before Allison.

However, she didn't have a tank top on, like Jennifer's, and instead was made to wear a tube top that wrapped so tightly against her large breasts, showing incredible cleavage, with her prisoner number embossed in big numbers on it. She was handcuffed as well, with her hands in the front, but didn't have the same waist chain set up as Jennifer. And on her head, she wore an orange prisoner cap with M. LEWIS stamped on it.

"Maddy!" exclaimed Jennifer, shocked as ever to see her.

Maddy looked right at her, smiled, and winky mischievously one eye. Jennifer had no idea what she was about to expect. This was all a surprise. Allison had really brought the whole band back together.

"Order, order in my court, please be silent inmate, no collusion allowed!" ordered Amy, looking for whatever reason to bang her gavel, probably from a Party City store.

Allison assisted the cuffed Maddy to be at the witness stand, and then Amy took over once again.

"Please state your identification," asked Judge Amy.

Maddy took a moment to pause, grinned at Jennifer. Jennifer knew this grin. It was the "sorry, but gotta give you the 'L' this time" grin. Jennifer felt goosebumps. She almost knew exactly what was going to happen.

"Your honor, my name is Maddy Lewis, hereby known to the court as Prisoner 298191," said Maddy in a "matter of fact" tone. "I am pleading guilty, as I, with Jennifer Malone, impersonated Sorority President Rebecca Van Miller's signature to approve of the torture we subjected our peers to. I am *deeply* sorry."

Wow, thought Jennifer. Absolute betrayal. She knew Maddy was just playing along, but looks like her friends were ready to really pin it to her. Allison meanwhile couldn't stop grinning but let out a fake gasp at the revelation.

"Maddy!" exclaimed Jennifer, in contest.

"Order, please do not additionally make me hold you in contempt, inmate!" said Amy, also having difficulty reeling in her smile. "Please help the other inmate off the stand, Allison, and have her join the defendant."

Allison, exaggerating, grabbed Maddy's arm and pulled her over so she was standing side by side with Jennifer. Jennifer couldn't believe how formal Allison and Amy were taking this - and Maddy playing along! Did she make a bet that put her in this position as well? Though she could totally see her getting recruited into this all and wanting to play the part.

Amy then cleared her throat loudly. Looks like Jennifer was about to hear her fate in this make believe criminal justice system. First, she looked at Maddy, who was ignoring Jennifer's wide eyed looks.

"I, the very honorable Amy Hopperfield, first find Maddy Lewis, noting her cooperation, as an ideal convict and sentence her to a mild spanking by paddle of 5 spanks, and light incarceration at the hands of Officer Allison for the night."

Maddy smiled, clapped her handcuffed hands, and said, "Thank you judge, I will welcome your spanking as punishment for my crime."

Wow, what a snitch, thought Jennifer, getting into the mindset of this roleplay. Amy then turned down Jennifer and did a great job of removing all the warmth from her face.

"And I find you, Jennifer Malone, hereby known as Prisoner 298192, guilty of false impersonation," she said, sternly, "And hereby sentence you to maximum security incarceration at the hands of Officer Allison, a public announcement of your crime, and 10 years in prison with eligibility of parole after 1 night served."

OOF. Talk about punishment not fitting the crime. Very clever way of giving her a real sounding prison sentence with a caveat of it just being for Halloween. Either way, wow, this sounds scary. Max security? Oh dear. Better not be worse than it currently is. And what is this public announcement?

Maddy meanwhile wiggled her butt as Allison took her arm and moved her to the otherside of the desk so that she was facing Jennifer. She gave her a wink as Allison had Maddy bend over so that her ass was protruding up in the air. Jennifer was wide eyed.

"Prisoner Maddy will receive the first part of her punishment now," piped Amy. Moments after, Allison withdrew a small paddle, almost from nowhere and gave Maddy a spank. Jennifer didn't know what to say, she was still taking this all in.

"The prisoner will count after each spanking," said Allison, promptly.

Maddy smiled. She clearly was in for the lighter punishment. She said, very coyly, "One, Officer Allison."

She was given another spanking and proceeded to count. 2...3...4...5! On the fifth one, Allison definitely spanked her harder which led to Maddy saying "Owww". Her hands were still cuffed to her front so she couldn't rub her butt.