Feature Slide

08162014s1
28th August 2014 08162014s1 Play

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.

08162014s1
05092014s14
21st August 2014 05092014s14
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The toilet is only three feet away but the prisoner can't be bothered with actually taking off his pants and so he spends the rest of the night with a very wet leg.  With the smell of piss all around him he becomes thoroughly aroused and masterbates with a rather large dildo up his ass.

05092014s14
05092014s13
14th August 2014 05092014s13
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In the hopes of deep play the prisoner prepares his ass inside and out with a massive douching.  Not satisfied with his overall cleanliness he follows up with a shower as well.

05092014s13
05092014s12
7th August 2014 05092014s12
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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.

05092014s12
05092014s11
31st July 2014 05092014s11
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Secured to the ceiling the bitch moans as Sir shocks him down to his core with an electric flyswatter and nerve stimulator.  Not satisfied with the screams Sir brings out the boot paddle and pounds the bitch's ass.  Sir then decides the bitches cock needs stimulating but doesn't settle for an average jerking, no, this bitch must beg...

05092014s11
05092014s10
24th July 2014 05092014s10
Featuring:
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Beating his own dick with a wild ferocity mega bitch struggles to keep Sir's cock in his mouth, he laps at the air to try to direct it back in and then Sir forces him to deepthroat it.  All of this, of course, is just foreplay as Sir soon bends him over the unforgiving chain and plows his ass, grabbing hold of his bindings and making them bite into his gut as Sir rams his dick in deeper.

05092014s10
05092014s9
17th July 2014 05092014s9
Featuring:
Play

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.

05092014s9
9th July 2014 05092014s8
Featuring:
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Having placed a rather large dong up his ass the bitch hunts for a second dinner and once he's blown his load he greedily scoops the cum in. 

05092014s7
3rd July 2014 05092014s7
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#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.  

05092014s7
05092014s6
26th June 2014 05092014s6
Featuring:
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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 dog he licks his cum off the bedsheet.

05092014s6

Iron Lockup Updates

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.

Play
28th August 2014
5.00
05092014s14

The toilet is only three feet away but the prisoner can't be bothered with actually taking off his pants and so he spends the rest of the night with a very wet leg.  With the smell of piss all around him he becomes thoroughly aroused and masterbates with a rather large dildo up his ass.

Play
21st August 2014
4.00
05092014s13

In the hopes of deep play the prisoner prepares his ass inside and out with a massive douching.  Not satisfied with his overall cleanliness he follows up with a shower as well.

Fetishes:
Play
14th August 2014
4.00
05092014s12

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.

Play
7th August 2014
4.00
05092014s11

Secured to the ceiling the bitch moans as Sir shocks him down to his core with an electric flyswatter and nerve stimulator.  Not satisfied with the screams Sir brings out the boot paddle and pounds the bitch's ass.  Sir then decides the bitches cock needs stimulating but doesn't settle for an average jerking, no, this bitch must beg...

Play
31st July 2014
4.00
05092014s10

Beating his own dick with a wild ferocity mega bitch struggles to keep Sir's cock in his mouth, he laps at the air to try to direct it back in and then Sir forces him to deepthroat it.  All of this, of course, is just foreplay as Sir soon bends him over the unforgiving chain and plows his ass, grabbing hold of his bindings and making them bite into his gut as Sir rams his dick in deeper.

Play
24th July 2014
4.00
05092014s9

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.

Play
17th July 2014
4.00

Having placed a rather large dong up his ass the bitch hunts for a second dinner and once he's blown his load he greedily scoops the cum in. 

Play
9th July 2014
4.00