https://www.429men.com/tags/prison/ Mon 12 Oct 2026 08:28:51 +0200 https://www.429men.com/videos/484887/intimate-moments-a-female-guard-succumbs-to-a-prisoner-s-desire/
Things are usually a bit rougher in prison, but this slim female guard obviously prefers a more relaxed approach. Every now and then, she strolls through the cells and lets an inmate have sex with her. Of course, the inmate could use the opportunity to escape, but why bother when you can have sex with a young female guard? The made-up policewoman with curly hair seems only interested in being fucked and ultimately getting a cumshot on her face. ]]> Wed 30 Sep 2026 13:11:18 +0200 https://www.429men.com/videos/484887/intimate-moments-a-female-guard-succumbs-to-a-prisoner-s-desire/ https://www.429men.com/videos/485302/yasmin-lee-fucks-the-innocent/
]]> Sat 26 Sep 2026 10:55:08 +0200 https://www.429men.com/videos/485302/yasmin-lee-fucks-the-innocent/ https://www.429men.com/videos/485722/a-slim-redheaded-woman-delivers-an-intense-blowjob-in-a-cage/
The slender babe is a redhead who has to give a blowjob. There's a reason she's behind bars. But to get her freedom, the young woman in nylons would do anything, and that includes giving the guard a blowjob. The man, of course, is happy to oblige and even opens the woman's cell. After the German blowjob, she also gets a cumshot in her mouth. ]]> Wed 23 Sep 2026 00:46:28 +0200 https://www.429men.com/videos/485722/a-slim-redheaded-woman-delivers-an-intense-blowjob-in-a-cage/ https://www.429men.com/videos/487008/a-forbidden-encounter-guard-and-inmate-ignite-passion-behind-bars/
In the women's prison, you'll find a few pretty women, including this inmate. The young woman is a slut with curly hair who only wanted to take a nap, but she starts touching herself. A guard catches the babe in the act and immediately jumps on the horse with her. So he fucks the young slut in the prison cell and then cums in her mouth. The guy really enjoys it. ]]> Mon 21 Sep 2026 13:17:09 +0200 https://www.429men.com/videos/487008/a-forbidden-encounter-guard-and-inmate-ignite-passion-behind-bars/ https://www.429men.com/videos/484084/swinging-delights-a-slim-beauty-s-night-at-the-club/
In a swingers club, a man is masturbating when a woman notices him. He invites the slender Jessy Hot in, because it's more fun with two people than alone. The woman accepts his invitation and immediately starts giving him a blowjob. Finally, she lies down with her upper body on a sex swing, allowing herself to be taken from behind while standing in this prison-like setting. A truly successful encounter in a German swingers club. ]]> Sun 13 Sep 2026 12:12:34 +0200 https://www.429men.com/videos/484084/swinging-delights-a-slim-beauty-s-night-at-the-club/ https://www.429men.com/videos/484611/tgirl-prisoner-jade-venus-always-gets-her-way-with-the-guard/
Tgirl prisoner Jade Venus always gets her way with the guard.The busty tgirl seduces him and kisses him.The blonde transsexual inmate sucks off his dick.The big tits trans lets him deepthroat her big tranny cock before she gets anal barebacked ]]> Sat 12 Sep 2026 15:25:01 +0200 https://www.429men.com/videos/484611/tgirl-prisoner-jade-venus-always-gets-her-way-with-the-guard/ https://www.429men.com/videos/462791/chantal-danielle-and-mazee-the-goat-navigate-the-challenges-of-being-locked-up/
In the far future, rebellious Chantal Danielle has been cuffed and locked in a prison cell that resists all her attempts to breach the barrier. She's gotten bored of pacing when the guards throw inmate Mazee in with her. The only thing worse than being locked up is locked up with a whiner, so Chantal tells Mazee she needs total silence and a good fuck, and he's happy to oblige. Chantal sucks him, then snaps her cuffs so she can put him right where she wants him as they fuck all over the cell. Chantal wears him out, and after he cums on her face, she finally gets some peace and quiet! ]]> Sat 29 Aug 2026 13:23:34 +0200 https://www.429men.com/videos/462791/chantal-danielle-and-mazee-the-goat-navigate-the-challenges-of-being-locked-up/ https://www.429men.com/videos/464242/lapaisita-tatiana-alvarez-yeri-blue-and-valentino-roca-get-cuffed-for-a-wild-adventure/
LaPaisita arrives at the prison, surrendering her buttplug and belongings before guards probe her holes and strip her into an orange jumpsuit. In her cell, Tatiana Alvarez explains rules while seducing her with hungry kisses and pussy grinds. The first guardian interrupts, as Tatiana sucks him deep, he calls Yeri Blue for backup, sparking a wild foursome fuck in cell and hallway. Girls take turns on thick cocks milking explosive cumshots across their faces and big tits. Exhausted guards collapse as the inmates steal keys and escape through the vents. ]]> Tue 14 Jul 2026 20:34:39 +0200 https://www.429men.com/videos/464242/lapaisita-tatiana-alvarez-yeri-blue-and-valentino-roca-get-cuffed-for-a-wild-adventure/ https://www.429men.com/videos/466199/gatita-veve-and-juan-lucho-deliver-an-unforgettable-experience-behind-bars/
Gatita Veve is a cop who has her run of the local prison... and all the available men inside. Juan Lucho is one such prisoner she has her eye on. She lets him out of his cell so that she can get a taste of his big dick! Maybe jail isn't so bad after all? ]]> Sat 11 Jul 2026 23:30:07 +0200 https://www.429men.com/videos/466199/gatita-veve-and-juan-lucho-deliver-an-unforgettable-experience-behind-bars/ https://www.429men.com/videos/467468/octavia-red-and-alex-jones-experience-an-unexpected-connection-in-the-drifter-part-1/
Stuck in stir, the Drifter(Alex Jones)'s claims of innocence fall on the deaf ears of the two deputies. But although the male cop is hostile, Deputy Taylor (Octavia Red) just might be more kindly inclined to the handsome stranger... especially when they're left alone. Taylor lets the Drifter know she's interested in his pistol, kissing him and then sucking him through the bars. She needs more and lets herself into his cell to get thoroughly satisfied, but after she takes a facial, there's a surprise in store for the red-headed deputy. The Drifter can't be held prisoner for long... but there's a bounty on his head! ]]> Wed 08 Jul 2026 15:13:20 +0200 https://www.429men.com/videos/467468/octavia-red-and-alex-jones-experience-an-unexpected-connection-in-the-drifter-part-1/ https://www.429men.com/videos/450524/prison-guard-anal-fucks-shemale-inmate/
Prison guard sees shemale inmate Andylynn Payne fucking cellmate Sasha Tatcha and wants his big cock sucked off.The petite brunette sucks both the tgirls big tranny dick and the guys boner before shes banged by the ts.The tranny bareback anal rides ]]> Mon 22 Jun 2026 00:15:52 +0200 https://www.429men.com/videos/450524/prison-guard-anal-fucks-shemale-inmate/ https://www.429men.com/videos/458025/transsensual-sweaty-gym-seduction/
This is nasty naughty TS sex! Loaded with mutiple positions and explosive climaxes you cannot miss! ]]> Fri 05 Jun 2026 05:00:49 +0200 https://www.429men.com/videos/458025/transsensual-sweaty-gym-seduction/