A Halloween Prisoner Pt. 06

Eventually, Jennifer finished Amara's torturous run, surviving Carmen's spankings while she was at it. The fourth kilometer was undoubtedly the worst of the five--something about tasting her own sweat and swishing flags from her breasts was peak humiliating. For the fifth kilometer, Amara let her off a bit easy, allowing her run the lap in the earlier prisoner gym uniform-costume, the only constraint being a shock to her shock collar whenever she dipped below six kilometers. That only happened once.

It wasn't beyond Jennifer that the girls had taken things too far, but her wetness kept her from protesting, secretly desiring some relief from her well excited pussy.

Now, the treadmill came to a halt, Jennifer huffing, tired from the whole ordeal.

"What now?" Jennifer asked, wanting to rub one out, too embarrassed to do it in front of Amara or Carmen.

"Well, I think both Carmen and I could agree that you passed your physical," said Amara.

"Amazing. What's my prize?"

Amara winked. "Getting admitted to prison."

Before she was allowed to change out of her running outfit, she was forced to take some photographs with Carmen and Amara, who were extra obnoxious with the poses, always asserting the fact that they were the law, and Jennifer was the prisoner. As a result, the handcuffs were used plenty for this gram-worthy photoshoot. To Jennifer's surprise, at one point, she was allowed to mock handcuff Amara, pretending to arrest her for being a dirty guard whilst the South Asian beauty pouted, but the role reversal only lasted a second before the cuffs were swatted from Jennifer's hands.

"Alright, let's get you changed into uniform," said Amara, returning the skimpy, orange uniform that Jennifer had first arrived in.

While Jennifer started putting on the clothes, Amara handed Jennifer's sweaty clothes to Carmen. "Can you get these to Sarah-Josephine? May come in handy for torturing Mark."

Jennifer blinked. "Wait, Mark's here?"

Amara devilishly smiled. "Of course. Speaking of which, hurry up and get dressed! It's time you meet your cellmate for the night."

* * * * * * * * * * * * *

Surprise, surprise. There was a young man at this party. Just one. Me. And trust me, I didn't want to be here. In fact, these girls hated me during college. Of course, I didn't hate them. Hell, I had a crush on half of them--especially Amara, Jennifer, Sarah-Josephine, and Annabelle.

Right, the bit of history about the girls hating me. They really did. They had a good reason to as well. See, I was a bit of a perv during college. Not like, stalk-girls-in-the-library-perverted, god no. Just a little bit of a perv. I was part of an opposing frat that won a bet against them ahead of Heartfest. Not even a bet, just a really shitty deal that Jennifer put together because we were fucking at the time.

Long story short, I put the girls in French Maid outfits. That was me. All me. I guess I had a thing for the costume, and I chose outfits from the whole spectrum. Big, frilly, gaudy ones. Ones that were just cute, the stuff an average college girl would buy for a party. And, of course, the downright skimpy cuts. I even made some of the girls run with a feather duster and a spray bottle.

Anyways, they hated me after I made them do that. I was a bit arrogant at the time, and I basically followed Jennifer's footsteps and made a bad deal. They banned me from sorority events after Heartfest, only agreeing to lift the ban if I agreed to a wager. In college, I was studying to become an investment banker, and had already been offered a $180,000 salary out of the gate. Long story short, if, in three years, I was making more money annually than anyone else in the sorority, my top four crushes--Amara, Sarah-Josephine, Jennifer, and Annabelle, would dress up as my prisoners for Halloween with me as their arresting officer. I know what you are thinking--why that? Well, truth be told, I have a huge prisoner-cop roleplay fetish, and the girls knew it, a number of them having dated me especially close to Halloween. I guess the girls knew that that was an offer I couldn't pass up, especially with my high salary. Well, there was the other side to that bet--if I lost, I, instead, would have to be their prisoner for Halloween, with an additional provision that I would have to do anything they command, nothing off the table. And guess what? Fucking Amara sold her startup two months back, and is making significantly more bank than me as a result.

The girls, who weren't too fond of Jennifer themselves, hatched a plan to punish the both of us. I knew this was coming, but I still was surprised when I opened my doorbell and found Amara standing there, smug smile across her lips, dressed to the nines as a sexy prison guard, whacking a police baton across her palm. She was joined by Sarah-Josephine who was wearing a gorgeous sexy cop outfit. Honestly, at that moment, I was excited--both of them looked so attractive.

Boy was I wrong. They forced me against a wall, handcuffed me aggressively, theatrically read me my Miranda Rights, and then proceeded to take cheeky mugshots of me with a inmate # sign around my neck. What do I mean by cheeky? Well, they first stripped me all the way down (I had to comply, rules of the bet), and then handed me a pair of orange bikini-cut panties that had PRISONER stamped across the ass. Amid my protests, they forced me to wear the garment over my derriere, swatting my butt when I proved too slow to don them. To make things worse, my erection was an obvious bump in all of those mugshots.

"Looks like Mark's excited to be our inmate," teased Amara.

"A little too excited, might I add," giggled Sarah-Josephine. "Perhaps we need to fix that."

I would soon learn that Sarah-Josephine was not exaggerating in her threat. The girls stressed that in their prison, there was one golden rule: male prisoners weren't allowed to relieve themselves. I promised that wouldn't be a problem, but given my throbbing erection, the girls weren't too convinced (didn't help that I gave my dick a few passing caresses as I moved my hands around).

Finally, I was offered a choice.

"So, we've chatted," said Amara, smiling stupidly, clearly enjoying every moment of this. "And you can either spend the entire party with your hands handcuffed behind your back OR we can try something more ... innovative."

I shrugged, somewhat curious to what innovative was referring to, and answered, "Let's do the innovative option."

Amara smiled even wider now. Out of her palm came a little orange device shaped like a penis, and after a bit of squinting, I gasped, realizing what it was: a chastity cage. On the side was the number 289178 stamped in black ink.

"I'm glad you chose it because we were going to force it on you anyway," said Amara, giggling.

"Hey! Don't reveal our secrets," teased Sarah-Josephine.

"No!" I protested, blushing. "You cannot possibly include--"

"Nuh, uh, uh," said Amara. "Could you repeat the rules of the bet?"

I stared at the floor, embarrassed. I feebly stated, "I have to agree to anything ... nothing off the table."

"Including a cock cage!" cheered Sarah-Josephine, her cheeks full.

"Including a cock cage," I muttered, red-faced.

With my hands still handcuffed behind my back, and the number-stamped panties slid down my buttocks, Amara iced up my cock, bringing it back to its normal size. I winced at the icy touch, and even more when she slipped the age around my member, locked it shut with a key, and proceeded to embed that key in a little holder tucked into her police badge. I, and my dick, was properly her prisoner.

"Can I get the rest of my costume," I insisted, rolling my eyes, suppressing the winces as my dick tried to engorge itself in its silvery prison.

"You mean, your uniform," teased Amara. "Let's not mince words here. You're our prisoner for real tonight."

"Yeah, yeah," I said snidely, looking aside.

"Oh please, as if you wouldn't be gloating over us had I not won our deal!"

"Whatever." I knew she was right. I would've been gloating all over them had I won, probably with my dick hard-as-fuck, uncaged, and throbbing.

Sarah-Josephine withdrew what apparently was the rest of my uniform. Admittedly, I'd expected it to be one of those orange, baggy jumpsuits; I was impatient for one since it would, well, cover up the fact that they'd made me wear panties. Stupidly, I'd ignored that very sign--they'd made me wear panties. What stops them from going even farther?

"You're joking," I huffed, eyes wide.

Sarah-Josephine theatrically shrugged. "Figured we'd dressed you exactly how you'd dress us."

She wasn't off-base ... well, only partly off-base. These girls already had their assets ... boobs ... but Sarah-Josephine was proffering an orange top cut like a sports-bra with ballooning inserted breast forms. The top matched the panties and was awfully embarrassing to say the least. The girls had had it custom made. On the left cup were the words INMATE MARK MONROE, #289178. On the right cup was a fake prison logo with the sorority crest. The back said PRISONER just like the panties.

"Let's get this on you," said Sarah-Josephine, uncuffing my hands.

I don't know what came over me, but I bolted for the door as soon as the cuffs were lifted. It's not like I had anywhere to go, but I felt like I should at least try to make a run for it. Big mistake. Huge mistake, honestly. Amara clicked a hidden button in her police badge and I suddenly felt the feeling of a dozen fire hands biting my balls. I winced and fell to the floor, grabbing at my package.

"YOU GAVE ME A SHOCK CAGE!" I blurted, hissing through my teeth.

"For good reason, it appears," said Amara, shaking her head at my collapsed figure. "Tsk tsk, I didn't expect the great Mark Monroe to welsh on a bet."

"I was ... I was playing my part," I whimpered, easing myself up.

"We'll decide on how you do that," said Amara smugly, spinning me around and forcing the uniform top onto me. They'd my size right; it fit snugly.

I looked ridiculous--my chest suddenly feminine, the elastic-like material hugging my body. Then, Amara suddenly swatted my buttocks making me yelp. A second later, she re-applied the handcuffs.

"And don't you dare disobey me again," she hissed.

I glanced at myself in the mirror. This couldn't be more embarrassing.

"This it, then?" I asked. "You're going to parade me around in a bra and panties set, prisoner themed."

"No," said Amara curtly. "We're not that cruel now, are we, Sarah?"

"We are not," said Sarah-Josephine, smiling mischievously. "Of course, if you're expecting a jumpsuit, it's not that."

"That would be too kind," added Amara. Then, she withdrew the final garment.

It was basically a prisoner dress--an orange romper. It reminded me of those Ally Catraz costumes I used to jerk off to (I told you, I have a prisoner fetish!). This one was, of course, custom made. The front were like the sports bra--had my name and prisoner number on one side, the sorority logo on the other. Surprisingly, the back didn't say PRISONER. Instead, it had the words: SORORITY PROPERTY.

This time when they unlocked the cuffs, I didn't attempt an escape. I very obediently put on the costume; like the others, it snugly fit. Amara christened the garment by gifting my butt another spank afterwards.

"Now, you better behave," said Amara, wagging a finder. "We reserve the right to strip you down."

"Why do I believe that's going to happen irrespective of my behavior," I said glumly.

Amara cracked a smile. "I cannot confirm or deny that."

I rolled my eyes.

"Before we go, we need you to say something for the memories," said Sarah-Josephine, withdrawing her phone.

"More pictures?" I complained, remembering the mugshots.

"No, a video," said Sarah-Josephine. "Repeat after me. 'I am Mark Monroe, and today, I'm the girl's obedient prisoner."

"Is this--"

"Yes!" hissed Sarah-Josephine, lifting the phone up and hitting the red button.

I sighed. This was going to be a long night.

"I am Mark Monroe, and today, I'm the girl's obedient prisoner."