https://www.transhero.com/tags/prisoner/ Thu 30 Apr 2026 22:06:16 +0200 https://www.transhero.com/videos/260925/sucking-and-fucking-behind-bars/
Kloe is a bad babe who ended up behind bars. But she is cunning in the most wicked sense, and she knows how to get what she wants. She knows how to convince Jors to do whatever she says. When she offers to suck his cock, he jumps at the opportunity. Jors and Kloe fuck around in the clink, and the Latina mommy rides his cock like a pro. Jors gives the sweet chick a big facial to enjoy. ]]> Thu 12 Mar 2026 15:10:44 +0200 https://www.transhero.com/videos/260925/sucking-and-fucking-behind-bars/ https://www.transhero.com/videos/338073/milf-fugitive-hungry-for-cock/
]]> Mon 09 Mar 2026 20:49:04 +0200 https://www.transhero.com/videos/338073/milf-fugitive-hungry-for-cock/ https://www.transhero.com/videos/116850/the-best-of-sex-behind-bars/
The bars on their cells won’t hold back these horny inmates from fucking! Watch some of Brazzers hottest babes spread their legs and get some cock while in lockdown in this steamy compilation! ]]> Fri 06 Mar 2026 14:25:32 +0200 https://www.transhero.com/videos/116850/the-best-of-sex-behind-bars/ https://www.transhero.com/videos/319519/disruptivefilms-ex-criminal-ass-fucked-by-his-parole-officer/
Ex-con Davin Strong hopes parole officer Jayden Marcos helps him, but Jayden screws him for freedom. ]]> Sun 15 Feb 2026 05:59:25 +0200 https://www.transhero.com/videos/319519/disruptivefilms-ex-criminal-ass-fucked-by-his-parole-officer/ https://www.transhero.com/videos/203156/hot-sex-in-a-jail-cell/
]]> Fri 06 Feb 2026 21:23:45 +0200 https://www.transhero.com/videos/203156/hot-sex-in-a-jail-cell/ https://www.transhero.com/videos/372970/district-attorney-s-interview-turns-into-steamy-escape-plan/
District Attorney Hopkins (Isiah Maxwell) interviews Gibbs's girls, Gigi (Xwife Karen) and Cindy (Connie Perignon), and they hint that they might be able to help find the missing cop, but not from lockup. The DA has Officer Baker (Jmac) take the women to the cell, and Gigi and Cindy see the opportunity for escape... if they can convince Baker to unlock the bars. The women treat him to a show, and Cindy talks him into taking out his cock. They suck it and back up onto it, and a little sweet talking convinces him it would feel much better without the bars in the way! The horny babes take the time to share the cop's dick till he busts on their faces before they bust out. ]]> Wed 14 Jan 2026 19:37:00 +0200 https://www.transhero.com/videos/372970/district-attorney-s-interview-turns-into-steamy-escape-plan/ https://www.transhero.com/videos/423294/lauren-phillips-is-going-to-have-to-pay-the-price-with-her-immaculate-body/
It’s time for a MYLF Labs update - let’s see what the experiment is this time! Behind Bars is pretty straightforward - see the hottest milfs in the business behind bars getting their pussies stuffed! Much like Shoplyfter Mylf, this experiment sees naughty milfs learning hard lessons. What a way to kick off a concept, too - who fucking hotter than Lauren Philips to set the bar? (No pun intended). She tries her luck and gives the guard a mean attitude, which he doesn’t take kindly to. Now, Lauren is going to have to pay the price with her immaculate body. Big perfect booty and an incredible bounce to her magnificent tits is like a godsend. She gets fucked no mercy by another inmate, and if she keeps up this attitude of hers, it certainly won’t be the last time it happens… ]]> Sun 04 Jan 2026 21:51:36 +0200 https://www.transhero.com/videos/423294/lauren-phillips-is-going-to-have-to-pay-the-price-with-her-immaculate-body/ https://www.transhero.com/videos/427096/prisoner-sahara-knite-shows-petite-body-to-horny-officer/
Petite prisoner Sahara Knite strips naked for Horny officer and shows him how to finger her wet and juicy pussy ]]> Sat 03 Jan 2026 21:00:01 +0200 https://www.transhero.com/videos/427096/prisoner-sahara-knite-shows-petite-body-to-horny-officer/ https://www.transhero.com/videos/107738/jamie-huxley-prisoner-ho-gets-her-pussy-pounded/
Jamie Huxley prisoner ho gets her pussy pounded in rough sex jail cell session ]]> Sat 27 Dec 2025 17:39:27 +0200 https://www.transhero.com/videos/107738/jamie-huxley-prisoner-ho-gets-her-pussy-pounded/ https://www.transhero.com/videos/37571/arielle-aquinas-bangs-the-tight-ass-of-blonde-chelsea-marie/
Arielle Aquinas is a strong willed prisoner of war. She refuses to give in to the demands of her tall, beautiful, busty captor, Chelsea Marie. ]]> Tue 08 Apr 2025 07:58:02 +0200 https://www.transhero.com/videos/37571/arielle-aquinas-bangs-the-tight-ass-of-blonde-chelsea-marie/ https://www.transhero.com/videos/35721/he-had-me-cumming/
Glamorous jailbird Kalli Grace is fed up with being stuck inside her cell. However, handsome prison guard Roman Todd is on hand help the gorgeous tgirl pass the time! Clad in sexy lingerie and leather boots, Kalli passionately kisses the hunky officer before bending over to suck his rock-hard cock, making sure to take the entire length of it in her mouth until she gags. Next, the blonde-haired babe asks Roman to teach her a lesson for being a bad girl, so he spanks her curvy ass while drilling her tight hole from behind in doggy position! Afterwards, the horny pair enjoy an intense side-fuck on the bed, and then all-natural Kalli sticks her legs up in the air to take a missionary-style pounding before hopping on top and riding Roman’s thick dick in reverse. Close to cumming, the beautiful trans babe strokes her shenis to orgasm, and then she kneels down to receive a sticky facial! ]]> Fri 11 Oct 2024 13:09:53 +0200 https://www.transhero.com/videos/35721/he-had-me-cumming/ https://www.transhero.com/videos/35719/banged-behind-bars/
After locking hunky criminal Michael Jackman inside his cell, sexy prison officer Kourtney Dash seductively bends over to retrieve her baton before sliding her rock-hard shenis between the bars! The mustachioed stud is eager to receive his punishment as raven-haired Kourtney bangs him in standing doggy, and then he greedily sucks the athletic tgirl's thick she-cock in a deepthroat blowjob. Afterwards, Kourtney penetrates Michael’s tight hole in missionary position until the big-boobed trans babe pulls out and cums inside the prisoner's mouth! ]]> Fri 11 Oct 2024 13:09:46 +0200 https://www.transhero.com/videos/35719/banged-behind-bars/