https://hdporn.video/tags/prison-sex/ Sat, 02 May 2026 08:35:07 UTC https://hdporn.video/video/196329/unbelievable-jail-scene-guard-fucks-prisoner-s-girlfriend-in-front-of-him/
Girlfriend gets fucked by BBC guard in prison and takes a deep creampie while her boyfriend watches ]]> Fri, 13 Mar 2026 12:40:59 UTC https://hdporn.video/video/196329/unbelievable-jail-scene-guard-fucks-prisoner-s-girlfriend-in-front-of-him/ https://hdporn.video/video/185137/ride-or-die-sc-8-raging-stallion/
EPISODE 8 - WIDE OPEN: Hell-bent on staying in Pierce Paris’s good graces – particularly following the violent incident between Beau Butler and Pierce’s rap star pal – Warden Cole Connor sends recently fucked inmate Alpha Wolfe to the business mogul’s palatial home. Ready to release the week’s stress, Pierce pushes Alpha onto his hands and knees, commanding him to spread his satisfying hole. Wielding his power, the mega-rich businessman sniffs and fingers Alpha’s fuzzy fuck-slit before pushing his eager tongue in for a taste. But, if he’s to truly prepare Alpha for his oversized cock, he’ll need to stretch the jailbird’s hole to the extreme. Pierce pounds the prisoner with two large man-ramming dildos before feeding Alpha his gargantuan cock and low-hanging nut sack. Pierce then grabs a stiff-dicked Alpha by his ankles, spinning the inked convict onto his back and spreading his legs wide open. From above, Pierce plunges his hard-on in and out of Alpha’s cavernous gape. Alpha’s rock-solid dick bounces against his thick bush as the billionaire smacks his furry ass and fucks him bareback on all-fours. Just when Alpha thinks his hole has been totally wrecked, Pierce throws him on his back and goes back in, balls-deep. The inmate, submitting fully to pleasure, shoots gobs of pearly-white cum onto his hairy chest. As Pierce pulls out of Alpha’s worked-over ass, he squirts a hot load of cum onto the prisoner’s tongue before putting his asshole-flavored dick back in Alpha’s mouth. Is Pierce satisfied with The Warden’s “gift” enough to forgive Cole, or will there be hell to pay? ]]> Wed, 17 Aug 2022 00:00:00 UTC https://hdporn.video/video/185137/ride-or-die-sc-8-raging-stallion/ https://hdporn.video/video/185146/ride-or-die-sc-7-raging-stallion/
EPISODE 7 - SLIPPERY WHEN WET: Convinced that new inmate Alpha Wolfe is the snitch perpetuating chatter about the warden’s sex trafficking scheme, faithful guard Drew Sebastian corners Alpha in the prison showers. Under the lukewarm water, Drew stuffs his thick cock down Alpha’s throat, gagging the bearded inmate. A particularly rough mouth-fuck doesn’t appear to be enough oral action for Officer Sebastian, who turns around and spreads his beefy ass in Alpha’s ruggedly handsome face. Alpha wants to stay on Drew’s good side, so he tongue-fucks The Officer’s musky backdoor before being braced up against the cold, tiled wall. Grabbing a bar of soap from the floor, Drew savagely cleans Alpha’s over-used asshole before plunging his raw dick deep inside. With a towel, The Officer holds Alpha down on the shower floor while he pumps his cock in and out of Alpha’s hairy butt. Drew takes it to the next level by fingering Alpha’s gaping hole before having him take a bareback ride on his massive dick. As soon as Drew hits the right spot, Alpha explodes and then kneels to take Drew’s fresh jizz all over his face. What secrets does Alpha know, and how might they impact his fellow inmates and The Warden? ]]> Wed, 10 Aug 2022 00:00:00 UTC https://hdporn.video/video/185146/ride-or-die-sc-7-raging-stallion/ https://hdporn.video/video/185147/ride-or-die-sc-6-raging-stallion/
EPISODE 6 - THE GANG’S ALL HERE: To punish Beau Butler for his misconduct at rap star Andre Donovan’s estate, the warden instructs his henchmen to take it out on the one thing that Beau loves most, his boyfriend. The guards arrange for intimidating inmates Bennett Anthony, Chris Damned, Reign and Alpha Wolfe to gang-bang Drew Valentino until he’s completely broken down. Bennett pushes Drew over a cafeteria table as Chris and Alpha hold the hairy prisoner in place. Ripping Drew’s prison-issued boxers at the back, Bennett rams his ginger cock straight up Drew’s bushy butthole before letting Chris have a turn. When Bennett notices that that the stoic Reign is tentative and hanging back, he pressures the tattooed hunk to get his enormous cock warmed in Drew’s guts. With Drew on the ground, he is served not only the raw dicks that were just deep inside him but also Bennett’s red-hot cum-chute. Once Drew is flipped onto his back, his legs are held wide apart by Alpha and Reign while Chris squats down to smother Drew with his sweaty asshole. Bennett next licks Drew’s meat ring, warming it up for a second round of bareback hole-punching that leaves Drew covered in everyone’s cum. Will Drew survive to protect his boyfriend from The Warden’s wrath? ]]> Fri, 05 Aug 2022 00:00:00 UTC https://hdporn.video/video/185147/ride-or-die-sc-6-raging-stallion/ https://hdporn.video/video/185333/deep-sentence-and-anal-oracle-club-inferno-dungeon/
Join the gaping studs of this fisting double feature ‘Deep Sentence & Anal Oracle’. Watch two movies on one spectacular DVD. First, a hardcore prison fisting fest, and then a vision quest filled with true pleasure magic, deep fisting and busted holes. Get locked up and have your fortune told with award-winning director Tom Moore, where you'll find everything you need to fulfill all of your piggiest desires. In ‘Deep Sentence’, prison Warden Dale Savage, pays a visit to inmate Drew Dixon to destroy the convict’s smooth ass in his cell. Joey Wagner walks in on his cellmate Sherman Maus, while he’s destroying fellow inmate Gunner's hole with his fist. Joey joins in, gets his fisting cherry popped, and double fists Sherman before sharing Sherman's giant load with Gunner. When Warden Dale Savage ends up a prisoner, he gets thrown into Drew Dixon's cell. Drew gets his revenge by double fisting the ex-warden. When Costas pays a visit to Drew Dixon, the ‘Anal Oracle’, Drew shows him his potential pleasure future by fist fucking the horny hunk. The psychic hole-stretching culminates with Costas blowing a load on himself as Drew finishes his reading with his fist still inside the curious spiritual traveler. Gunner and Joey Wagner seek the advice of fortuneteller, Sherman Maus, who suggests fisting as a way to bring them together. After both Gunner and Joey get stretched by Sherman, they take Sherman's advice and double fist him until all three studs blow their loads all over Sherman's tight body. Costas pays a final visit to Drew Dixon to finally complete his studies on the energy power of fisting. Drew rides Costas' clenched fist until he's convinced that Drew has finished his lessons. From intense, gritty prison fisting to finding a pleasure awakening through deep, penetrating and stretching fist play, 'Deep Sentence & Anal Oracle' is the hardcore fisting double feature you’ve been waiting for. ]]> Fri, 16 Aug 2019 00:00:00 UTC https://hdporn.video/video/185333/deep-sentence-and-anal-oracle-club-inferno-dungeon/