https://www.thepornstar.com/tags/prison-sex2/ Tue 14 Apr 2026 20:03:15 +0200 https://www.thepornstar.com/videos/435334/clea-gaultier-the-prisoner/
]]> Sat 11 Apr 2026 14:51:54 +0200 https://www.thepornstar.com/videos/435334/clea-gaultier-the-prisoner/ https://www.thepornstar.com/videos/429716/licensed-to-lick-aiden-starr-prison-guard-lesbian-fun/
Aiden Starr and Haley Cummings 2 big natural tits prison guards enjoy sweet lesbian fun together in a cell. ]]> Sat 11 Apr 2026 11:00:42 +0200 https://www.thepornstar.com/videos/429716/licensed-to-lick-aiden-starr-prison-guard-lesbian-fun/ https://www.thepornstar.com/videos/162087/women-prisons-are-sexy-spicy/
Hot lesbians lick pussy ]]> Sat 27 Dec 2025 09:44:54 +0200 https://www.thepornstar.com/videos/162087/women-prisons-are-sexy-spicy/ https://www.thepornstar.com/videos/168488/hot-august-ames-becomes-a-prisoner-s-bitch-sex-video-pinflix/
]]> Wed 03 Dec 2025 11:45:28 +0200 https://www.thepornstar.com/videos/168488/hot-august-ames-becomes-a-prisoner-s-bitch-sex-video-pinflix/ https://www.thepornstar.com/videos/394473/cowboy-1st-session/
This is Cowboy's very first video. I ran into him in an alley behind a bar, singing his heart out. He said it was his birthday. That was the start of a 16 year tumultuous relationship. I still love him to death and wish he was here. He loves sex, and is a total loving machine. He'll give it to you all night long. Cowboy is in prison now and I miss him terribly. ]]> Mon 15 Sep 2025 12:30:56 +0200 https://www.thepornstar.com/videos/394473/cowboy-1st-session/ https://www.thepornstar.com/videos/153312/scamangels-abella-danger-zoe-monroe-seduce-fuck-prison-guardian/
Abella Danger gets locked up, and she needs Zoe Monroe to get out. They seduce the jail guardian and suck his big dick inside the cell. He fucks these hot girls, and after the intense sex session, these women scam him into letting them go. ]]> Sun 27 Jul 2025 14:38:49 +0200 https://www.thepornstar.com/videos/153312/scamangels-abella-danger-zoe-monroe-seduce-fuck-prison-guardian/ https://www.thepornstar.com/videos/103895/prison-lesbo-sex-with-a-shy-asian-cutie/
Life in prison is hard, no doubt. But having a cute cellmate can certainly improve the conditions. Short-haired lesbian Lily Cade seduces her Asian cellmate Marika Hase and quickly removes her orange jumpsuit to satisfy her pussy like no one before. ]]> Wed 14 May 2025 19:18:11 +0200 https://www.thepornstar.com/videos/103895/prison-lesbo-sex-with-a-shy-asian-cutie/ https://www.thepornstar.com/videos/303827/hot-shot-for-shot-remake-of-one-of-our-classic-scene3/
Police officer Joseph Hart is only a few feet into Baxxx's jail cell when he begins shedding his uniform and recreating Hal Drake and Mike Cole's inmate hookup from the Falcon Studios' classic 'Upperclassman'. Leaning down on a cot, the horny cop starts off the behind-bars fuck by swallowing down the detainee's big dick and throwing back his muscular thighs as Baxxx rims his hole. With both men wanting more, Baxxx begins barebacking the officer and having his cock go from ass-to-mouth until Joseph's bubble butt is completely coated in cum. ]]> Thu 16 Jan 2025 21:46:03 +0200 https://www.thepornstar.com/videos/303827/hot-shot-for-shot-remake-of-one-of-our-classic-scene3/ https://www.thepornstar.com/videos/165640/porn-blonde-burglar-chloe-rose-ravaged-in-prison-by-detective/
Blonde Thief Chloe Rose Fucked In Jail By Detective ]]> Sat 16 Nov 2024 17:54:09 +0200 https://www.thepornstar.com/videos/165640/porn-blonde-burglar-chloe-rose-ravaged-in-prison-by-detective/ https://www.thepornstar.com/videos/165366/two-sexy-teens-scarlett-cadey-having-some-alone-time/
Former prisoner Cadey has just come out from jail, and she bumps into a unsuspecting teen that wants to know everything about life behind bars. They start kissing on the bed and smiling at each other, but after that they swiftly undress each other and the rest is history. ]]> Sat 12 Oct 2024 17:51:11 +0200 https://www.thepornstar.com/videos/165366/two-sexy-teens-scarlett-cadey-having-some-alone-time/