https://www.freepornflix.com/categories/prison-play/ Sun, 21 Jun 2026 22:40:14 UTC https://www.freepornflix.com/video/1005885/shoplifting-sluts-get-stripped-and-spanked-in-prison/
Repeat offenders melodie and darina are back in custody for shoplifting… again. this time, strict prison guard noir is done playing nice. she orders melodie to strip down completely naked while darina was already naked and scared in the corner on the bed. intimidated, shaking, but a bit bratty, melodie had to peel off every piece of clothing under her loud, intimidating shouts until she was standing there totally bare and exposed. but the punishment has only just begun. noir makes the humiliated girls turn on each other and spank one another hard. loud, stinging slaps on their bare asses while she watches and barks more orders. every smack echoes through the cell as the two naked shoplifters are made to discipline each other, red marks blooming on their cheeks while they whimper and obey.  fear, nudity, humiliation, and corporal punishment… exactly what these repeat offenders needed.   ]]> Sat, 20 Jun 2026 10:28:05 UTC https://www.freepornflix.com/video/1005885/shoplifting-sluts-get-stripped-and-spanked-in-prison/ https://www.freepornflix.com/video/998587/dein-erster-tag-bei-mir-im-gefangnis-deutsche-version-wmv/
Angeführt und in meine aluminium käfigzelle gesperrt, bist du nun mein gefangener! verhaftet für wiederholtes, unerlaubtes wichsen, ist dir sicher klar, dass auch dein schwanz hinter gitter kommen wird! den kleinst möglichen keuschheitskäfig hab ich für dich ausgesucht. und den legen wir jetzt an!erst mal kommen ein paar schmerzhafte nippelklammern, um sicher zu gehen dass dein schwanz auch nicht zu sehr aktiv wird. nach dem anlegen des käfigs kommt die hammerharte polizei peitsche in den einsatz. was dich wohl sonst noch so als mein häftling erwartet?wmv file version ]]> Wed, 17 Jun 2026 09:18:36 UTC https://www.freepornflix.com/video/998587/dein-erster-tag-bei-mir-im-gefangnis-deutsche-version-wmv/ https://www.freepornflix.com/video/988950/prisoner-of-femdom-1080p/
Prisoners arrive at the uk penitentiary. they are brought here to be "detained and trained' depending on the crimes committed will determine the punishments & the amount of time a prisoner will be incarcerated. these two prisoners are new and settling into their new environment. basically chained to the wall in stocks interrogated & humiliated by the chief prison warden. what will be their fate...? ]]> Sat, 13 Jun 2026 12:24:34 UTC https://www.freepornflix.com/video/988950/prisoner-of-femdom-1080p/ https://www.freepornflix.com/video/952985/first-hour-in-her-prison-cell-kora-summers-locked-up-in-her-prison-cell-shackled-and-barefoot-1080p-mov/
Kora is an inmate facing a long sentence. she walks into the cell and the chains on her ankles scrape across the floor. the door is slammed shut behind her, and the co removes her handcuffs. the shackles are left on. she won't need them off, and they're not coming off. she's going to be in this cell all day, every day, for the entire duration of her sentence.kora looks around the room. she paces. she investigates the center piece of her new home, a toilet sink combo. she nervously talks to herself and anxiously looks for something to occupy her focus and energy. there is nothing, she is locked up, and all she has to do is sit and stare out the bars. this first hour passes so slowly, and every hour that follows will be much the same. endless monotony awaits her in this cold modern dungeon. this is only the first hour, but the fear and anxiety seems to quietly build in the background of her mind as she tugs at the uniform she is wearing, which never seems to be able to sit comfortably on her body.this is the 1080p mp4 version of this video. 4k and mov formats are also available. ]]> Tue, 26 May 2026 11:26:07 UTC https://www.freepornflix.com/video/952985/first-hour-in-her-prison-cell-kora-summers-locked-up-in-her-prison-cell-shackled-and-barefoot-1080p-mov/ https://www.freepornflix.com/video/947106/the-mad-nurse-in-the-nuthouse-wmv-1080p/
]]> Sun, 24 May 2026 11:17:36 UTC https://www.freepornflix.com/video/947106/the-mad-nurse-in-the-nuthouse-wmv-1080p/ https://www.freepornflix.com/video/932457/what-to-do-with-a-blonde-maid-in-a-cage/
The blonde maid alice is kept in a cage by the witch judge and tormented and penetrated in it. she is allowed out of the cage to lick the wet floor clean and is dragged over the slippery floor of the dungeon. back in the cage, she pees in a high arc as she tries to reach the key to her freedom with her bare feet from the outside...scene #1 from movie 'alice – hexenflug (the flying witch)' – german language ]]> Sun, 17 May 2026 11:34:09 UTC https://www.freepornflix.com/video/932457/what-to-do-with-a-blonde-maid-in-a-cage/ https://www.freepornflix.com/video/909107/industrial-control-session-rotating-punishment-game-720-mov/
Chained to the frame, divine eve is completely immobilised, whilst her mistress lunatika slowly explores her body with various toys, taking full control of her reactions.   ]]> Thu, 07 May 2026 10:38:45 UTC https://www.freepornflix.com/video/909107/industrial-control-session-rotating-punishment-game-720-mov/ https://www.freepornflix.com/video/900751/lady-dark-angel-slave-arrival-processing-and-admission-of-guilt-at-the-owk/
Her thigh high boots clicking against the pavement stones, miss courtney leads in a troop of slaves into the compound, greeted by lady dark angel and miss morrigan hel. the slaves are lined up in a row and have to give up all their belongings for the time that they are at the owk to serve the sentence of their offences. no phones either nor watches as time is of no importance to them. it is all about being punished for their offences as following the assigment of their personal numbers, each slave is required to give a summary of their offences.the ladies examine the assembled slaves prior to admonishing them and then leading. them off, each carrying a bucket. the slaves follow suit, are not allowed to speak and especially not look at the asses of the ladies leading them. ]]> Sun, 03 May 2026 11:25:21 UTC https://www.freepornflix.com/video/900751/lady-dark-angel-slave-arrival-processing-and-admission-of-guilt-at-the-owk/ https://www.freepornflix.com/video/894212/lady-dark-angel-slave-girl-discovers-it-pays-to-stick-to-the-rules-in-prison/
The new female slave in lady dark angel’s entourage has been caught riling up the other girls in prison. upon discovering her antics, lady dark angel assures the girl she should be worried as she is taken out of her cell and ordered to mount the punishment chair with slots on which kneeling would be most uncomfortable. in addition, her hands are then secured and impaled against spikes at the top of the bacj of the chair. lady dark angel could leave the girl tied up for hours and then impresses on the girl she would deal with her excatly as she chooses.very soon the girl finds out what this means as lady dark angel brings her well-practised and hard hand down on the bottom of the female prisoner, delivering a hard spanking in various ways. forgetting her place,  she talks back to lady dark angel earning herself a double-handed spanking delivered at various levels of speed and impact. she tells the girl she will have a sore bottom for the rest of the day, the effect serving as a reminder of her mistress and that she will be hers to play with. the girl will have no option but to offer her servile agreement. her spanking continues harder and harder till lady dark angel is certain she has had enough, for now. ]]> Thu, 30 Apr 2026 12:31:43 UTC https://www.freepornflix.com/video/894212/lady-dark-angel-slave-girl-discovers-it-pays-to-stick-to-the-rules-in-prison/ https://www.freepornflix.com/video/886357/industrial-control-session-rotating-punishment-game-720/
Chained to the frame, divine eve is completely immobilised, whilst her mistress lunatika slowly explores her body with various toys, taking full control of her reactions. ]]> Sun, 26 Apr 2026 13:53:22 UTC https://www.freepornflix.com/video/886357/industrial-control-session-rotating-punishment-game-720/ https://www.freepornflix.com/video/885479/fugitive-strips-for-freedom/
“you gotta believe me officer, i’m innocent!” cupcake is in a standing cell, handcuffed and wearing an orange satin jumpsuit. she paces and pleads until the warden arrives! cupcake tries to explain her situation but the warden wants something in exchange for setting her free: seeing her strip! cupcake tries to strip as much as she can while cuffed, desperate for escape, but the warden laughs after watching and walks away. the next day the warden makes the same offer, and with only one hand cuffed to the cell bars, cupcake fully strips - humiliated but eager to go home! as the warden walks away poor naive cupcake realizes she fell for it again. will she ever escape? ]]> Sun, 26 Apr 2026 12:31:53 UTC https://www.freepornflix.com/video/885479/fugitive-strips-for-freedom/ https://www.freepornflix.com/video/876824/ily-arrested-for-drinking-while-dri-ng-part-2/
Stopped for a check, the girl is checked. while waiting to be let out and searched, the policeman handcuffs the wheel of the car for her safety   part 2 ]]> Wed, 22 Apr 2026 10:22:55 UTC https://www.freepornflix.com/video/876824/ily-arrested-for-drinking-while-dri-ng-part-2/