https://www.transhero.com/tags/jail/ Tue 14 Apr 2026 15:23:25 +0200 https://www.transhero.com/videos/238239/law4k-pretty-lassie-con-hermosos-servicios-de-cuerpo-joven-dos-guardias/
]]> Thu 19 Mar 2026 04:48:47 +0200 https://www.transhero.com/videos/238239/law4k-pretty-lassie-con-hermosos-servicios-de-cuerpo-joven-dos-guardias/ https://www.transhero.com/videos/256992/fuckin-for-freedom/
All a caged bird wants to do is get out and spread its wings. What does a caged jailbird want to do? If the jailbird is a thick, big-bootied bitch like Tia Sweet, she'll want to get out of confinement, too. With her luscious assets, we don't think that'll be too hard. Tia grabs the attention of our janitor Big Pike by popping her booty and making her ass cheeks clap. "Why don't you look over here?" she asks with a purr. "If you help me get out of here, I'll do you a little favor." "Yeah?" Pike responds. "What kind of favor?" Tia's favors are the best you'll ever get. She starts by sucking on his fat cock while she bounces her ass behind her. "Oh, your cock is so big," she says in between gagging on it. This is where Tia really shows she craves her freedom as much as she does a stiff cock splitting her cunt. She hops on top of him reverse cowgirl and pops her ass and pussy for Pike. "Oh, I needed that cock," she moans. Then Pike gets up, turns Tia over and beasts on her pussy doggy-style. He's getting everything this favor has coming to him, and so is Tia. She cums with moans that are a mix of pain and pleasure as he beats her pussy up, and she vibrates her ass on his cock when another orgasm washes over her. Eventually, this jailbird gets her own favor in return: a hot load of cum all over tanned ass. "So, are you going to let me out now?" Tia asks. "Well, I guess I owe you now," Pike responds. ]]> Wed 18 Mar 2026 01:31:33 +0200 https://www.transhero.com/videos/256992/fuckin-for-freedom/ https://www.transhero.com/videos/360219/good-milf-bad-milf/
Audacious cops Cece and Tokyo have caught Nick Strokes, an accomplice in a major heist. After interviewing him for a while without any results, the ladies decide to take a whole new approach, a sexy kind of questioning that will surely make the felon spill the beans and make Chief Feels feel proud of them. ]]> Mon 16 Mar 2026 01:18:03 +0200 https://www.transhero.com/videos/360219/good-milf-bad-milf/ 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/283309/spring-breakers-part-3-welcome-to-skeetsville/
Spring Breakers (Part 3 of 3): After Rory, Octavia, and Jasmine have had their fun with Lucky, they are reprimanded and brought into custody by Skeetsville law enforcement. Skeetsville isn’t just any ordinary town - freeuse is legal and enforced here. Officers Charles and Donnie interrogate the spring breakers and try to get to the bottom of their heist. The girls know very little about Lucky, so they have nothing to give the officers except their sweet pussies. If the girls want to keep the good times rolling while also staying out of trouble, they’ll have to go along with whatever the officers tell them. ]]> Sat 07 Mar 2026 17:58:31 +0200 https://www.transhero.com/videos/283309/spring-breakers-part-3-welcome-to-skeetsville/ https://www.transhero.com/videos/358306/jail-sex-with-gay-black-dude-and-cell-mate-marco-di-antoni-and-micah-martinez/
Marco has a gambling problem and as the results of these bad habits he is in Jail. Jail has not seemed to have set him straight because he seems to be able to find just about anything to bet on in here. So playing Dominoes with his cellmate even on this he has to place a bet with the only thing he has left to wager, his ass. His cellmate has been in for years and knows how to let a boy build up his debt to him. So finally after the last game it was put up or put out. Marco gets up to head into the cell but Micah says, "Oh No right here bitch where everyone can see who owns your ass now." Marco can see everyone is watching now but with little choice he crawls over to Micah's Cock and starts sucking. Finally even Marco admits it's kind of hot sucking cock in front of everyone like a slut. Micah is going to put him through all his paces eating his ass and fucking him real good for all the boys to see. Finally shooting his nut right on Marco's chest Micah tells Marco to leave the nut where it is and go down to cell 30 to see his buddy Leon, cause he is next and likes his boys messy. ]]> Sat 07 Mar 2026 07:36:35 +0200 https://www.transhero.com/videos/358306/jail-sex-with-gay-black-dude-and-cell-mate-marco-di-antoni-and-micah-martinez/ https://www.transhero.com/videos/404495/submissive-slave-spanked-hard-while-in-jail-and-chains/
Submissive slave is spanked hard while in chains, showcasing the pleasure and pain involved in submission. ]]> Sat 21 Feb 2026 23:30:00 +0200 https://www.transhero.com/videos/404495/submissive-slave-spanked-hard-while-in-jail-and-chains/ https://www.transhero.com/videos/163335/case-no-8476358/
Case #8476358 - April 25th, 9:32 PM. Suspect is a dark-haired woman. She identifies herself as Tia Cyrus. Employees alert the Loss Prevention Officer on duty of suspicious behavior in the candy section of the store. The suspect is detained and the edible underwear is found on her body. The suspect refuses to serve jail time or face arrest, and to avoid law enforcement involvement, she strikes a deal with the Officer on store premises. The rest of this case is classified. ]]> Tue 17 Feb 2026 14:46:21 +0200 https://www.transhero.com/videos/163335/case-no-8476358/ https://www.transhero.com/videos/289656/man-s-best-friend-my-loyal-lola-aiko/
Lola is a naughty girl, and she loves being treated like one. When she gets on all fours while wearing her collar, leash, and laced underwear, she always begs me to satisfy her as her master. She is always craving a bone that she can lick and lick until her urges disappear, and I have one just for her inside my pants. ]]> Mon 16 Feb 2026 14:43:42 +0200 https://www.transhero.com/videos/289656/man-s-best-friend-my-loyal-lola-aiko/ https://www.transhero.com/videos/274072/liza-del-sierra-the-busty-nurse-pleasuring-all-the-prisoners/
]]> Sun 15 Feb 2026 09:29:34 +0200 https://www.transhero.com/videos/274072/liza-del-sierra-the-busty-nurse-pleasuring-all-the-prisoners/ https://www.transhero.com/videos/137284/case-no-3192018/
Case #3192018 - June 20th, 7:21 PM. Suspect is an Asian female with red-dyed hair. She identifies herself as Kimberly Chi. She calls her mother, Christy Love, to pick her up. To make sure her daughter doesn't go to jail, Christy agrees to follow through with proper protocol while her daughter watches. The rest of this case is classified. ]]> Sun 15 Feb 2026 07:14:13 +0200 https://www.transhero.com/videos/137284/case-no-3192018/ https://www.transhero.com/videos/207228/porn-intense-jail-fuck-with-ambitious-redhead-octavia-red/
PORN+ Intense Jail Fuck With Ambitious Redhead Octavia Red ]]> Mon 09 Feb 2026 10:28:13 +0200 https://www.transhero.com/videos/207228/porn-intense-jail-fuck-with-ambitious-redhead-octavia-red/