Prisoner's Dilemma (rework) (Patreon)

When John had met Tracy, he was a small-time  gangster making some bucks by running scams and selling drugs on the  campus. He instantly knew she was the perfect girl for him the moment  he’d seen her. Tracy was a dream coming true: sexy but shy, smart but  very insecure about her abilities and, best of all, easy to manipulate  for a guy like him. She fell for his roguish charm in no time and John  had put her looks to good use ever since. He would work out schemes with  her being the bait for rich young students on campus. She would seduce  them, get them drunk and then take compromising pictures, blackmailing  them for cash. If they refused, John would pay those entitled pricks a  visit and force them to pay the hard way. Not only did Tracy make them a  lot of money, she was also willingly pleasing John in bed whenever he  so demanded. As the weeks of their liaison turned into months, he had  made her his obedient girlfriend at daytime and a dangerous femme fatale  at night, always looking out for stupid men to prey on.

Everything  went down well, for John especially. While Tracy became more and more  involved with plotting new coups, he spent most of his money on girls.  He was never quite sure if Tracy knew about his infidelities, but he  just assumed she was too dependent on him to leave. When the cops  eventually took notice of their little business and things got too hot,  the couple decided to take a few months off and planned to return when  everything had settled down a bit. They went to a remote place somewhere  in the eastern pacific region, a country John had rarely ever heard of  before. It could have been their sanctuary, had it not been for Johns  old habits taking the upper hand again… After he had blown most part of  their savings for women and gambling, he soon needed to think of a way  to make more. So, as always, he dragged Tracy back into the outlaw life.

They played their game like they  did back home, but Tracy was looking out for businessmen rather than  students this time. One of their victims was related to some very  influential person in that strange country’s high society. His  reputation at stake, he was willing to pay almost everything for the  pictures to disappear – and he did. John thought they’d hit the jackpot,  but Tracy got suspicious about how easy all of this was going down. She  convinced him to hide all the cash they’d made in the basement of an  abandoned barn in the countryside and keep a low profile for a while.  As  always, she was right. Screwing over important people in a corrupt  country was never a good idea, and soon they got arrested by the local  authorities. Tracy was scared, so John promised her everything would be  alright. The cops hadn’t found the money and with just one person  accusing them, there wasn’t enough evidence to justify a long sentence.  They promised not to testify against the other, before they were  separated for interrogation and brought to a run-down prison somewhere  in the outskirts of the city.

It was at this point John noticed that every official he’d seen there was female. Maybe a coincidence,  he thought. Most of them didn’t even speak English, so it was hard for  him to fully understand what was going on. After hours of being  interrogated by a surprisingly young and beautiful officer, John was  offered a simple deal: he should confess to all their crimes and they  would go easy on him, blame Tracy for most of their wrongdoings and let  him go on parole. If he didn’t confess though, they’d charge both for  what they could proof, resulting in a six-month sentence in prison. He  didn’t have to think long about this. Would he spill the beans, they  would lock Tracy away and they’d be out of the business for years. Also,  a sentence of six months was ridiculous compared to what he’d be  expecting had they found out all about their criminal career. All of this is a fucking joke, he thought, we’re gonna do our time, get out, pick up the money and leave this god-awful country for good.  The warden accepted his decision with a smirk. She disappeared behind  him and suddenly, a spike of incredible pain paralyzed his whole body.  The electric buzzing of the warden’s taser still echoing in his ears,  everything went dark.

He woke from a  dull aching in his balls, realizing he had been bound and gagged in a  deviously unpleasant position and could barely wiggle. A stinging pain  from his nipples was the next thing he noticed. He stared down his rigid  body as far as he could and found the cause of his discomfort: clamps  had been applied to his nipples, his cock was locked away in a little  steel cage and his balls were tied and stretched out with rope. Much  worse though was another sensation burning in his body which felt like  an unappeasable thirst. He could hardly believe it, but he felt intense  arousal! John was incredibly horny and, despite his predicament, his  cock was straining in its prison, fueled by this unnatural desire. He  moaned in agony, as he heard clicking high heels approaching his cell.  The door opened and Tracy appeared in the frame. John stared at her in  disbelief. She looked gorgeous, fresh and clean and as seductively as  she always used to when hooking up with her victims. When she entered,  the scent of her perfume filled the room, causing his cock to  involuntarily twitch and ooze a stream of precum down to the floor. “Hi  John! Oh god, look what they did to you! You’re such a naughty boy, but  this is even worse than I imagined!” Confused, John could just gaze upon  her perfect nylon-covered legs as she took a seat next to his bound  form. “Oh, poor boy, you still don’t get it, do you? Never been the  smartest, sweetie! Let me explain. They made me the same offer as they  made you. Had we both testified against each other, they’d have had  enough evidence to put us behind bars for way longer… but even if we  both refused there was this six-month lockup… And you know, I am just  not made for prison. So, there was a simple solution to this dilemma. I  testified against you and just hoped you’d be stupid enough to keep your  promise and keep your mouth shut. And I must say, I’m really happy you  did! You’re so much stronger than I am, baby! Now I’m free to go, all  thanks to you!”

John was sweating, a  terrible feeling creeping up on him, far worse than the pain in his  balls and nipples, even making him forget the desperate need to come for  a moment. What was happening here? “I see it’s still hard to grasp. I’m  afraid, since I blamed everything on you and you were very uncompliant  and didn’t confess, they’ll punish you far beyond the regular treatment.  You’re basically their example now for an unregretful, cruel criminal  who forced his innocent girlfriend to join him in his unlawful  activities. The wardens were so caring to me once they knew all you did.  They told me a bit about your sentence. You’re in for the maximum  security and discipline program, tightly bound and gagged all the time!  And I bet you feel a little… tingly down there, huh? Must be the new  drug they’re testing on you. They didn’t go into details, but from what I  understood it’s multiplying the arousal someone is able to feel,  causing the worst case of blue balls you could possibly imagine.  Combined with that mean chastity device… this must be pure torture!” He  produced another muffled scream into his gag. Fuck you! What have you done?! Get me out of this!  “Yeah, it’s quite harsh. Since the revolution here carried a matriarchy  to power, the new government isn’t too fond about cocky men in general.  But you’re a special case babe, you should have seen the faces of all  those female wardens when I mentioned your obsession with sex and how  you treat females as objects. Oh gosh, they can’t wait to get their  hands on you! Judging by that tag on your collar, you’re definitely  gonna spend some quality time with them, haha!”

Was this a joke to her? Get me out of this you cunt! I can’t stand this!  “As for the duration of your stay…”, she continued, ignoring his  efforts, “I’m afraid you’ll be serving a life sentence, baby.” Her calm,  matter-of fact delivery of that sentence made John explode in furious  rage. He screamed in his gag and fought his bonds as hard as he could,  but to no avail. Tracy reached for the plugged tube protruding from his  gag and gently guided his head back to face her. “That’s right. Scream.  Struggle. It’s too late. The deal is sealed and there’s no way back.  You’ve taught me everything you knew about scamming people, about  ripping off innocent men. You thought you were the big bad boy, but you  never were as ambitious as I am. You would have never stopped your  gangster-lifestyle and sooner or later would have both of us gotten  killed. It’s quite ironic, but the best decision you ever made for me –  not confessing or telling the cops where we hid the money – now turned  out to be the absolute worst decision you could have possibly made for  yourself.” As the meaning of her words was slowly sinking in, John  desperately tried to produce any coherent words, convince her she was  making a mistake, sweettalk himself out of this like he had done so many  times before. Out came a pitiful, sobbing noise causing Tracy to smile.

“There’s nothing you can do. Who’s the helpless little girl now? So, I  think I’ll put your share of the money to a better use after I’ve left  the country. I will live the life I could never have with you, have fun,  travel, party… fuck. All while you’re trapped here, teased and denied,  unable to escape your lifelong torment, just sentient enough to realize  that you became just another victim of the monster you created. Bye now  honey. Enjoy your sentence!”