A Halloween Prisoner

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Jennifer let her friend choose Halloween costumes. Big oops.
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Part 1 of the 6 part series

Updated 06/09/2023
Created 06/08/2020
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Jennifer usually put in a lot of effort into her Halloween costumes. Last year she went as a witch and spent hours on her makeup and broom. Before that, she went as a cheerleader but managed to get an official Dallas Cowboys uniform and even learned the cheers. But this year, she was letting her friend Allison choose the costume.

It all started during a bet. They were playing a board game.

"Jennifer, I bet I can outdo your Halloween game," said Allison.

Jennifer, thinking that was absurd, replied: "Shut up Allison, my costume game is prime. In fast, last year you just went as a ghost."

"Sure, but I'm willing to go all out this year, but I get to choose the costumes," shot back Allison. It always surprised Jennifer that Allison usually had poor costumes. She was an attractive girl, with breasts fit for a model and usually a wardrobe well equipped for any event. Oddly, she just never had shown a penchant for a good Halloween costume.

Jennifer also considered herself attractive, with slender brown hair and perky breasts. She just loved dressing up, and showing off her body at events.

After thinking about it for a little bit, she figured that worst comes to worst, she will have one poor Halloween in the books. Maybe this would inspire Allison to be a bit more creative.

"Ok, you are on," said Jennifer, "But no pre-made costumes."

"Yup, don't worry."

-- -- --

Fast forward to Halloween, and Jennifer and Allison were going to go to a costume party in Brooklyn hosted by their sorority sister from their college. They lived in Manhattan and it was a bit of a trek to Brooklyn, but they were pretty excited to see everyone and their costumes.

Jennifer was waiting at home. Allison was supposed to arrive soon, and she was bringing their costumes. She hadn't the faintest clue what it was going to be. While this was a friendly bet, she hoped it was something good. After all, she just loved to dress up.

The doorbell rang.

"Allison, is that you?" said Jennifer, as she walked towards the door.

"Hey Jennifer, I have our costumes, but I need you to unlock the door and then turn around, as I want mine to be a surprise," yelled Alison from the other side.

Hmmm. Perplexing, thought Jennifer. Maybe this won't be such a let down after all. She said that sounded good, unlocked the door, and then turned around, closing her eyes for extra effect.

Allison presumably walked in, Jennifer hearing she had some sort of heel or boots on since the footsteps were audible. But then all of a sudden she back Allison's hands grab her wrists, pull them back behind her body, and a cold, metallic device encircle her wrists all of a sudden. It happened all so fast.

"Allison, what the fuc-" yelled Jennifer, unable to see what was going on.

"Jennifer Malone, you are under arrest for false impersonation," said Allison in a theatrical voice.

OMG, thought Jennifer. Was Allison really going for the cop and prisoner set-up. She then realized that the cold metal things around her wrists must be handcuffs. She quickly tugged her wrists apart and felt there was a chain attached. A short chain as well - these felt like real handcuffs.

Allison then tugged on Jennifer's left arm and spun her around.

Damn. She looked stunning. She had on a police cap and was wearing blue heels and dark navy tights. Her outfit was a blue unitard but across her breasts was the word "POLICE" in white ink. She could tell Allison had stamped it on herself given minor discrepancies. She had on a realistic looking badge, and around her waist was a belt with a realistic looking baton, another two sets of dangling handcuffs, a pouch slightly smaller than a tennis ball, and a walkie talkie. On one side of her chest was a nametag that was engraved with the words "OFFICER ALLISON".

Allison smiled and then turned around so Jennifer could see the back of her uniform. It was snuggly fit alongside her body, and had the word POLICE on the back as well in larger letters.

"Damn Allison you look stunning," replied Jennifer, still in a frenzy due to her arms handcuffed behind her back.

"Thanks hun, but it's time to get you processed," she said coyly, with a little smirk. Jennifer was impressed that she was actually staying in character. She had clearly put in a lot of work.

"What do you mean, processed?" asked Jennifer, albeit knowing what Allison meant. Allison spun her around again, then unlocked the handcuff from one wrist, turned Jennifer around, and then locked her hands in it quickly in the front. Jennifer was pretty impressive how smooth that was; it was like she had been practicing it.

"So what am I going to be, your prisoner?" asked Jennifer.

"Oh hun, you aren't just my prisoner. Tonight you are a prisoner of the New York State Government," smirked Allison. She then fetched a bag by the door that she had brought in with her.

"Ok, very funny, but my costume better not just be these handcuffs, as fun as that sounds," Jennifer replied.

Allison looked up at her and said mysteriously, "oh you are going to wish your costume was just the handcuffs."

Wow, a threat? She was amused how much in character Allison had gotten, though she was also a little bit nervous what she meant. Deciding to get into character herself, Jennifer shot back, "Alright, you bitch, bring it on."

Allison smiled as she withdrew something rolled up from her bag. She then proceeded to go to the wall in the back. Then Allison unfurled the thing, letting it roll out with gravity. Jennifer noted that it was pasting to the wall as she did that, and then realized it had numbers for height and everything. She realized what was up: it was a mugshot background. Wow, Allison had actually gotten a prop as well.

Allison went back to Jennifer and then dragged her by her handcuffed arms in front of the mugshot background. Jennifer joked in protest, "wow, good job with this, but a fancy ruler isn't fixing up my simple costume situation right now."

Allison just smiled in response and had Jennifer stand in front of the background. She then touched Jennifer's hair to quickly straighten it up, and then said, "Alright prisoner, time for you to get booked."

"I'm sorry, I beg your pardon miss?" said Jennifer coyly, but also a little sincerely confused.

She then proceeded to take out of the bag a folded up camera tripod and an old fashioned looking camera. How much money had she spent on these props, wondered Jennifer? This was more involved than even the year she dressed up as a cheerleader. Allison set up the tripod, and mounted the camera on top.

"Don't worry Jen, this won't be in tomorrow's newspaper," Allison winked, before turning around, "Or will it."

"I gotta say, I'm impressed so far."

Allison then returned to her bag and pulled out a rectangular thin item with strings attached. She then walked over to Jennifer and reached over Jennifer's neck, to which Jennifer bowed her head in instinct. She draped the strings around her neck so that the rectangular piece hung over her chest, just below her breasts. She couldn't see it easily so she pivoted her body to the right to access a mirror on the nearby, adjacent wall.

She almost melted in amazement at how much detail her friend actually had gone into. It was also embarrassing, a good bit embarrassing at that, that her friend had made her a real life mugshot sign. It read,

JENNIFER MALONE

298192

CRIME: FALSE IMPERSONATION

NEW YORK STATE INMATE

It looked real with block, plastic white letters, and was definitely not cheap.

"How'd you find this? And how did you find the time," asked Jennifer, bewildered.

"Alright inmate, eyes straight at the camera," spoke Allison sternly, in character, completely ignoring Jennifer's question. Jennifer laughed at how serious she was taking this. Allison then pressed a button and the camera flashed.

"Alright Prisoner, turn to the left," she said, leaking a small giggle. Jennifer went from grinning to frowning to get into the vibe and turned to the left. The last mugshot definitely had her laughing - she must have looked like a lunatic. Another flash. "Turn to the right" Another flash.

Jennifer had to admit that getting arrested wasn't exactly on her bucket list, but if it was, this would have counted plenty.

"Ok, Allison, I am very impressed with the camera and this background and all, but a fancy sign and handcuffs, you hardly are topping last year's costumes," teased Jennifer.

"No, the sign isn't even part of your costume you dummy. That's just for booking you," said Allison as she lifted it off of Jennifer.

"Ok, but what's my real costume then. You didn't just buy one of those jumpsuits you get at Party City, right?"

Allison approached her, ignoring the question again, and unlocked her handcuffs. She flexed her wrists afterwards, confused that she now didn't have either of the things she thought composited her costume.

Allison put the handcuffs on the table and then turned to her and said, "Alright Prisoner, time to get you in uniform. Strip."

This took Jennifer off guard. They had seen each other in underwear here and there, such as when they went to the beach and stuff and were changing - since they are such close friends - but that wasn't expected.

"Oh, I can just change in the bathroom if - " asked Jennifer.

Allison now unhooked her baton and waived it at Jennifer: "Don't talk back inmate, I'm the boss here, now strip," said Allison sternly, and then adding in a coy manner, "Plus, you wanted a real costume, Jen. Comes with a real experience."

Jennifer, while hesitant, decided to go with it and started to take off her shirt and shorts. She was in her blue bra and panties and then looked at Allison for further instructions, just ensuring she didn't mean everything.

"I'm sorry, didn't I say strip," said Allison sternly.

"Allison, I get it, you want to do a good job winning this bet, but you are taking this a tad too far-" started Jennifer, still smiling, but then Allison grabbed her shoulder, spun her around, and spanked her butt with her baton.

"I"m sorry, but as far as I remember, you are in jail and I am a cop, so do as I say," said Allison, not breaking her trance at all. Damn, she's gotten good at this acting, thought Jennifer. Was she going for an Emmy or something?

Jennifer had to respect the effort, decided to take the plunge into new ground and take off her bra and panties, so that her breasts and crotch were fully exposed. She felt pretty vulnerable now. And slightly, ever so slightly, turned on.

To lighten the mood, she let out a little giggle, and shaked her body so her breasts jiggled.

"Alright, time for a cavity search," said Allison, sternly. Wait, cavity search!?? Jennifer now felt violated.

"OK, ALLISON, YOU ARE TAKING THIS-" she started, but then Allison started laughing and cut her off.

"I'm joking you dummy, but I wanted to see your reaction. Don't worry though, you won't get a fun cavity search but you will get quite a prison uniform."

Jennifer breathed a sigh of relief. Whatever this mysterious uniform was, it couldn't be as bad as a cavity search. Damn, this girl had gone all out.

Allison leaned down to rummage through her bag. She then rose with some folded garments. She first tossed Jennifer a prison orange article.

"Put this on, they are your panties."

Jennifer put them on quickly, relieved to have clothes. She didn't even bother to inspect them at first. Since there was a mirror in the room, she would be able to see after. She turned to the mirror to look.

Oh, wow. Wow. The panties were pretty embarrassing. On the front of them, they had the word "GUILTY" in block letters, neatly stamped on professionally.

"Oh wow, this is definitely a female uniform," said Jennifer, trying to admit to herself she was definitely going to get embarrassed this Halloween.

"Prisoner, turn around to look at the back," replied Allison, still ever in character.

Jennifer revolved around. On the back was in small, black text "PRISONER" and below that in bigger, blocked numerals "298192", stamped right across her ass. It was a pretty covering panty, a little bit shorter than a pair of boyshorts, so the letters were fairly massive.

Then something hit Jennifer. Looks like Allison tried to trick her and was breaking the rules here.

"Wait, Allison, the rule was no precreated costumes, this seems pretty precreated," said Jennifer, finally feeling she found a weak spot in Allison's bravado performance.

"Nah, Jenni-, sorry inmate, trust me, this was costume made just for you."

She then tossed Jennifer what was obviously a bra. Jennifer put it on and looked at the mirror.

Her heart did a backflip. On the left breast, it prominently said "J. MALONE" and below that "PRISONER". On the other bra cup, it had her prisoner number in block letters. Unless a costume shop randomly made costumes with her last name and first initial on it, this was clearly a custom pair. They were fairly large bra cups, permitting a sizable font.

"Woah, how did you -" asked Jennifer.

"No more questions, more photos," chided Allison, making a "no-no-no" gesture, wagging her finger. She then pulled Jennifer back to the background and then unclipped one of her handcuffs from her belt, swung Jennifer around, and then re-cuffed Jennifer's hands behind her back.

"Woah Allison what-"

"We need an official mugshot of you in the costume, silly," she said, fetching the mugshot sign and draping it over her neck. She was fairly exposed - she was basically just wearing "prison underwear" - not even a full uniform.

Allison ran back to the camera. She took a photo and Jennifer felt pretty turned on now. This was definitely sexy but maybe.. a bit too sexy? Allison then repeated from before, "Turn left!"

Jennifer did, now a little bit over this whole charade of things. This seemed a bit excessive. Allison took another photo with flash. She then said:

"Turn left."

Jennifer, confused, turned just her head to Allison and said cheekly," You dumb officer, this is already my left."

"No, prisoner, turn left again, it's time for an ass mugshot"

Jennifer was pretty surprised at that but had to admit it was making her pussy really wet. She took the instruction to heart, and turned so that her butt faced Allison, well aware of what was stamped across her ass.

Then something occurred to Jennifer, that somehow didn't occur before. There had to be more to this costume than just this.

"Wait, Allison, this can't be all to my costume right??!?" asked Jennifer, a bit alarmed her friend was going to parade her into this party handcuffed in just a bra and panties, and a very embarrassing bra and panties at that.

"Don't worry silly, of course there is more," said Allison smiling. Jennifer breathed a sigh of relief. Allison then went and fetch her whole bag. She then tossed Jennifer an bright orange, rubbery crop top. She must have forgot that her hands were still handcuffed behind her back, so it fell on the floor.

"Oh, let me help you out of those so you can actually put that on," said Allison, realizing her mistake.

"Thanks," said Jennifer, trying to get a glimpse of the outfit. Allison unhandcuffed one of her hands and then immediately slipped on the item onto her. Right after she had it on, Allison quickly grabbed her hands and re-handcuffed them behind her back. Jennifer was about to protest about her being a bit rough, but Allison quickly cut in: "Gotta keep my inmate under lock and key."

Allison then spun Jennifer sideways so that she could take a look at herself in the mirror. The crop top in massive letters had the word "PRISONER" on it in black. Underneath that was her prisoner number. It was rubbery and looked very sexual, and snuggly fit, promoting her breasts.

"Damn, I look hot," she mouthed under her breath. Allison meanwhile went to grab another thing from her bag. Jennifer could hear something metallic inside. What was possibly in there?

Allison pulled out a long assembly of chains. She looked at Jennifer and said, "You know how a few years ago you learned all those Dallaw Cowboy cheers and snatched a real cowboy uniform. Well I got you transport chains to compensate."

Damn, this girl was good. Allison then took two massive cuff things and cuffed them to her ankles. They weren't that tight but definitely would restrict her ability to run or even walk fast. It then connected to a central O ring, and from there a chain extended up.

Allison then unhandcuffed her wrists and proceeded to re-cuff them on the front. She then took this chain from the legs and attached it to the handcuff chain using some type of box that clipped on top. The box was rigid, and soon, Jennifer realized that her actuals wrists would have way less mobility now.

"Woah, this is crazy," said Jennifer.

Allison then retrieved another chain that made Jennifer shudder as she circled it around her waist. Jennifer had seen these in court cases before that prisoners wear. The metal was cold, and she felt it through her crop top, so she shuttered a little bit. Allison then connected it to the box around the handcuffs, effectively forcing her wrists to stick close to her waist. She was really immobilized now.

"Yup, this is what I mean about the rest of your costume, prisoner," Allison said.

Jennifer was in shock. She was completely tied up in these chains, in a very, very embarrassing tight fitted crop top (which extended just a tad below her belly button) and then just panties below. Meanwhile her friend was dressed in a sexy police costume.

"Allison, I can't possibly just wear-" said Jennifer.

"Shush inmate, I'll be right back," said Allison. She left and took the camera with her as she went. Jennifer started admiring herself in the mirror, rubbing her legs together a little bit. She was noticeably a little wet but not too wet that someone would notice without looking. Granted, if you saw an attractive woman dressed like this, would you not look at her crotch? She did look hot and incredibly sexualized right now. The chains added a lot of submissiveness but her outfit below also just screamed slut.

Allison returned and was holding a stack of two dozen or so papers. She went up to Jennifer and said," So, tonight, you are my prisoner, and at times, you may escape, and it is my job to find you. But, it makes sense for me, as a cop, to inform the common people of the party to keep a look out for a menace like you. So hence, I'll be posting these on the party walls."

Jennifer looked down and was nearly floored how fast her friend had made this. It was a WANTED flyer, with her mugshot picture (in the uniform) and used her ass picture for half of the copies. On the bottom it said in large font: "JENNIFER MALONE IS WANTED FOR FALSE IMPERSONATION. HANDCUFF, RESTRAIN, AND SPANK IF NECESSARY"

Jennifer was impressed but the last word shocked her," Wait, spank??"

"Oh, I forgot to mention, I took some inspiration from some older prisons that used to use corporal punishment on inmates, and since I am the cop, I get to decide. So that's the boat you are in, love," said Allison smiling. Jennifer was confused and then Allison retrieved from the bag a black ping pong paddle with the words "PRISONER SPANKER" on it. It had a little chain on it with a lock.

Before Jennifer could even react, Allison clipped it to Jennifer's waist chain, so that it dangled by her side.

"You know, in case any of the guys didn't have a Prisoner Spanker with them," said Allison with a wink.

"Listen, bitch, this is going way too far-" Jennifer said now, really, really humiliated how intense Allison was taking this.

Allison then took a few steps back and put her hand on her mouth. She pressed her body against Jennifer so that she could feel her other set of hanging handcuffs and baton. She then said:

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