Feature Slide

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25th September 2014 08162014s5 Coming Soon

The pee-shy prisoner is chained down across from his cellmate and told that they would remain chained until he summons the courage to piss but when inspiration fails to bring the flow he and his companion start to pass the time.  Both hard and frustrated they test the limits of their chains and find that they are both barely within reach of each other. 

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08162014s4
18th September 2014 08162014s4 Play

Blindfolded and gagged the prisoner has no idea what Sir has in mind for him.  He is secured to a chair using incredibly heavy duty leather cuffs and he hears the coming of the boy who is equipped with a rather large dong secured to his boot.  Rock hard, drooling and moaning one can only assume he is enjoying himself as he desperately fights to cum.

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08162014s3
11th September 2014 08162014s3
Featuring:
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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.

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08162014s2
4th September 2014 08162014s2
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Stuck between his rocks and a hard place today's subject gets abused by Sir with his balls in a humbler.  In order to keep his members in place he must endure Sir's game.

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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.

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05092014s14
21st August 2014 05092014s14
Featuring:
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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.

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05092014s13
14th August 2014 05092014s13
Featuring:
Play

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.

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05092014s12
7th August 2014 05092014s12
Featuring:
Play

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.

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05092014s11
31st July 2014 05092014s11
Featuring:
Play

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...

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05092014s10
24th July 2014 05092014s10
Featuring:
Play

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.

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Iron Lockup Updates

08162014s4

Blindfolded and gagged the prisoner has no idea what Sir has in mind for him.  He is secured to a chair using incredibly heavy duty leather cuffs and he hears the coming of the boy who is equipped with a rather large dong secured to his boot.  Rock hard, drooling and moaning one can only assume he is enjoying himself as he desperately fights to cum.

Play
18th September 2014
4.00
08162014s3

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.

Play
11th September 2014
4.00
08162014s2

Stuck between his rocks and a hard place today's subject gets abused by Sir with his balls in a humbler.  In order to keep his members in place he must endure Sir's game.

Play
4th September 2014
4.00
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