Session Three for Prisoner #08162014
Category: BDSM and Fetish
Added: 14 Sep 14
Views: 217
Comments:0
Duration: 0:02:06
Tags: long term confinement cells masks jerk off sucking cum cum Iron Lockup

Description: The Prisoner, being generally useless in his cell gets a temporary reprieve when Sir allows him to suck on his cock. The bitch eagerly takes to Sir's cock and hungrily deep throats it till he chokes. He is horny beyond control and isn't satisfied till he's covered in Sir's load.
Two Prisoners
Category: BDSM and Fetish
Added: 31 Aug 14
Views: 2261
Comments:0
Duration: 0:02:06
Tags: restraints chains CBT threesome tug of war big dick boots masks Iron Lockup

Description: Rob Karota & Milan Tatoo|Milan has two things he's pretty stoked about - one is a new camera that he's not putting down for anything - not even a blow job that his big dick (the other thing he's stoked about) is currently getting. The pierced up tattooed bad boy is watching Rob suck on his schlong and then he rams him hard with his raw pierced pecker.|bareback, twink, piercings, kissing, big dick, blow job, POV, tattoos, cum shots, Twinks 08162014s1|Sir likes balls. They're like puppies who like a game of tug of war, it's just that the boys they are attached to don't seem to agree. Stuck between the discomfort of the ball stretchers tugging on their jewels and their arms bound above the boys work to find a happy medium. Of course, Sir disagrees with this objective and raises the stakes.
Prisoner #05092014s12
Category: BDSM and Fetish
Added: 15 Aug 14
Views: 2829
Comments:0
Duration: 0:02:06
Tags: cells gas mask jock masturbate long term confinement dildo anal play Iron Lockup

Description: Strapped into a gas mask prisoner rams a large dong up his ass and masturbates while seeming noting that he can barely feel the huge dong with his stretched asshole.
Cumming To
Category: Leather
Added: 07 Aug 14
Views: 2286
Comments:0
Duration: 0:05:10
Tags: bareback breeding fetish fisting leather big cocks punks gloryholes

Description: Demitrius takes on Matthias' cock through an iron gate glory hole, then its time for a mutual suck n fuck until Matt spooges a huge load all over his face.
Prisoner Number 05092014
Category: BDSM and Fetish
Added: 20 Jul 14
Views: 1922
Comments:0
Duration: 0:02:06
Tags: long term confinement cells masks jerk off boots big dick Iron Lockup

Description: Eagerly awaiting the next scene the prisoner passes the time in his usual manner by playing with his cock, he continues to jackoff after the scene
Prisoner # 05092014s7
Category: BDSM and Fetish
Added: 12 Jul 14
Views: 1597
Comments:0
Duration: 0:02:06
Tags: gas mask cells long term confinement piss intake cavity search the pit Iron Lockup

Description: 08022013 returns to the Iron Lockup, Sir does the intake and is very thorough with the cavity search. After given a good welcoming the bitch is shown to the newly remodeled, super cozy pit where he is given a golden warm second welcoming
Prisoner #05092014 Session Six
Category: Leather
Added: 28 Jun 14
Views: 2186
Comments:0
Duration: 0:02:06
Tags: gas mask cells long term confinement piss wanking cum cum cum eating toys butt plug Iron Lockup

Description: The prisoner is locked up again. He's got strict orders to piss himself instead of having permission to use the toilet. Obeying authority makes the bitch so horny that he can't help but jerk off with his piss still pooling on the floor. After finishing off on his hands and knees like a bitch he licks his cum off the bedsheet.
Enter Prisoner 05092014
Category: Leather
Added: 21 Jun 14
Views: 1763
Comments:0
Duration: 0:02:06
Tags: fisting restraints rubber masks Iron Lockup

Description: "Warning: Do not misuse this piece of equipment" It was so clearly printed on the Roman chair, one has to wonder if this includes fisting. Tonight the bitch wants to know if he can finally take puppy's paws which happen to be larger than your average paws. So much lube, so much whining, so much begging, and such shiny rubber pants... it was a "full" evening.
Prisoner 05092014s3
Category: BDSM and Fetish
Added: 08 Jun 14
Views: 1407
Comments:0
Duration: 0:02:06
Tags: restraints sports equipment punching electro whipping masturbation masks Iron Lockup

Description: Punching bags hold many drawbacks for boxers. For one, they don't move and buckle like a person, they don't respond to your touch the same way, they don't fear shot loaded gloves. Of course, Sir found a solution to these problems: chain a bitch to the bag; it really is the best of both worlds. A little time with a flat fiberglass cane summons the most pathetic begging, not that Sir is receptive to such things. Don't miss the dance of the little red stick.
Runway Model Jerks
Category: Solo (1)
Added: 14 Jun 14
Views: 27637
Comments:0
Duration: 0:11:26
Tags: model jerk solo sexy frat big dick

Description: Jack Rider really is your All-American boy. Tall, dark, and handsome with a southern twang to him that will melt your heart. He's very clean cut and straight forward, but there's a bad boy side to him few get to see. Jack just got done swinging the iron at the driving range with Josh Harnett, and is feeling horny. The best part about this full package is his voluptuous ass and hard throbbing cock!
Prisoner Number 05092014s2
Category: BDSM and Fetish
Added: 07 Jun 14
Views: 740
Comments:0
Duration: 0:02:06
Tags: masks restraints big dick nipple play paddle beating flogging Iron Lockup

Description: Consider for a moment being blinded, with limited audible capabilities, restricted airflow and no way to escape. Sir has left you alone with a boy whose depth of cruelty is an unknown.Today, that boy has decided your ass needs tenderizing... sorry bitch, you're fucked!
Mummification
Category: BDSM and Fetish
Added: 23 May 14
Views: 2420
Comments:0
Duration: 0:02:06
Tags: mummification restraints nipple play sucking big dick jerk off cum cum clamps mask Iron Lockup

Description: This week's scene is one for the books because it takes mummification to a whole new level. Instead of saran wrap and duct tape Master Pan has chosen palette wrap. When the prisoner sweats and gives off body heat, the wrap begins to fuse with the skin. The finale has the effect of a full body band aid being mercilessly ripped off.
Prisoner #01172014s12
Category: BDSM and Fetish
Added: 07 May 14
Views: 2623
Comments:0
Duration: 0:02:06
Tags: cells long term confinement mask jerk off chastity Iron Lockup

Description: Having been worked up on the available porn left in the prison our frustrated bitch finds himself working to hunting for any drop of pleasure alotted by his steel chastity device. His balls are strained and the barely accessible tip of his cock does little but draw a pathetic stream of precum. Eventually desperation overtakes him and the real war between him and his chastity ensues. No, we won't be telling you who wins...
Prisoner Number 01172014s10
Category: BDSM and Fetish
Added: 18 Apr 14
Views: 1427
Comments:0
Duration: 0:02:07
Tags: workout masks gym CBT paddles caning Iron Lockup

Description: You think your trainer is mean? Try a psychotic puppy workout complete with CBT, tt, ass and thigh caning. No, your sets are not timed, puppy doesn't care if you are winded, go bitch go!
AJ Irons fucks hairy twink
Category: Latino
Added: 24 Apr 14
Views: 1155
Comments:0
Duration: 0:06:17
Tags: dirtytony gay for pay gay-boys gay-anal gay-assfuck gay-blowjob gay-fucking gay-bigcock gay-oral gay-porn gay-sex gay-porno gay-sucking

Description: This summer the east coast met the west coast. Our friend from Penn-Seth, was warming up the sheets with California born and raised Fabian. Long and lean Seth is no stranger to my door, and he can't wait for beautiful brown skinned Fabian to come a'knocking on his. They talk about music, surfing, mountain biking, snowboarding... is there anything my boys can't (or won't) do? While discussing the joy of sex and all of its sights and smells, Fabian's love muscle starts flexing before the rest of him does. A steamy makeout session ensues, and quickly after Fabian gets a little more than he bargined for. Undaunted by the sheer size of the cock before him Fabian dives right in-lips first, trying to conquer Seth with his tongue. Not to be outdone, Seth pushes Fabian to his feet and gives him the sucking of his life. Oh yes, it gets better! The action gets more and more hardcore as the boning begins. There is everything from a romantic missionary position to a cowboy ride Fabian is not likely
Getting His Hole Stuffed
Category: Anal Sex / Fucking
Added: 10 Apr 14
Views: 1365
Comments:0
Duration: 0:04:16
Tags: all-americanheroes gay-boys gay-anal gay-assfuck gay-blowjob gay-fucking gay-bigcock gay-oral gay-porn gay-sex gay-porno gay-sucking gay-handjob gay-sucking gay-cocksucking gay-jackoff gay-blowjob AJ Irons

Description: Fabian is ready to plunge his throbbing Latino dick into Clayton's horny hole. Fabian finally having his chance to plow his huge rod deep into that tight, bubble ass of Clayton's. He gets so excited, ramming his dick straight into the officer's puckered hole. These two could definitely fuck for hours, but like all good times, they must come to an end eventually. Fabian, fucking his power bottom, pulls out his hard cock, unleashing streams of warm cum all over Clayton's tan torso. With man gravy dripping down Clayton's torso and eager to show his own load, huge wads of creamy man juice spray out of his swollen head onto his ripped six pack. FUCKING HOT!
Straight Lee
Category: Masturbation / Jerking Off
Added: 31 Mar 14
Views: 465
Comments:0
Duration: 0:05:00
Tags: mature dads older str8 straight gay4pay hairy

Description: Another nice find from the sidewalks of Ponce de Leon avenue. He's a 27 y/o, iron worker who has travelled around the country but seems to want to settle down here. Says he'd "love to fuck a sexy man in the woods", although he's basically straight.
Prisoner 01172014s7
Category: BDSM and Fetish
Added: 25 Mar 14
Views: 659
Comments:0
Duration: 0:02:07
Tags: mask bondage bound boots punching masturbation edging Iron Lockup

Description: The prisoner is such a wimp that he needs kneepads just to kneel on the floor. All the boy does is hit him a bit and the bitch starts whining and moaning. Still, it seems like he likes it; his dick gets hard and stays that way despite suffering further indignities.