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05162015s5
24th June 2015 05162015s5
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Helpless against Sir's teasing of his cock the prisoner moans and jerks in vain as Sir violates his ass with his fingers. Sir releases his hands and the prisoner begins edging himself while still inverted.  With Sir's finger back in his ass the prisoner blows his load onto his own face.  

05162015s5
05162015s4
17th June 2015 05162015s4
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The prisoner swings back and forth as the pressure begins to build in his face.  His boots strapped are to the ceiling and his arms bound up by his chest as Sir teases his cock, foreshadowing the tease to come.  Lubing up his gloved hand Sir prepares to violate the prisoner's ass as the prisoner rocks helplessly upside down.

05162015s4
05162015s3
10th June 2015 05162015s3
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Standing like a mighty tree the prisoner's cock remains hard enough to pop.  Sir teases the tip which is already over stimulated and then he begins to reinsert the dong into the prisoners ass, making him move against his restraints.  Sir's hand goes full force on the prisoner's cock till it becomes too much and showers of cum flood out and drench his thighs. 

05162015s3
05162015s2
3rd June 2015 05162015s2
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In a long leather, chain, and straight jacket suspension the prisoner lies back with his cock standing at full attention.  He squirms against his bindings and awaits whatever evil Sir has planned for him.  After a long period of anticipating Sir begins to finger the prisoner's ass making the prisoner squirm more violently and moan with each stimulation.

05162015s2
05162015s1
27th May 2015 05162015s1
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Securely confined in a straight-jacket, the prisoner has no chance of escape from the start.  And he's naked from the waist down so his cock hangs out ready to be manhandled.  Sir Pan lays the prisoner flat on the gurney and his cock goes hard immediately.  He slowly prepares to raise the prisoner into the air where he will be at the full mercy of Sir Pan's devious whims.

05162015s1
05042015s2
20th May 2015 05042015s2
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Still wet from his golden shower the boy continues to service Sir's rock hard cock.  He braces himself against the bars of the cell as Sir forces him to deepthroat his cock.  With long snowy bursts Sir covers the boy in his cum, wiping his hand off on the boy's head.

05042015s2
05042015s1
13th May 2015 05042015s1
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The boys eyes are transfixed on Sir as he orders him to open up and deep throat his nightstick.  The boy is then bent over the prison toilet and made to take a beating to his junk and ass.  Sir then face fucks the boy but instead of cumming he showers the boy in piss.  

05042015s1
04282015s1
6th May 2015 04282015s1
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Arms suspended from the ceiling, helpless to endure Sir's intentions the boy is quickly bombarded by rapid, feather-light touches.  His protestations go unregistered as the fingertips work his body until finally he is out of breath and red in the face.  Sir embraces the boy as he tries to regain his breath.

04282015s1
04192015s1
29th April 2015 04192015s1
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Right after the little stinger whip is finished being made it's turned on it's creator.  Sir restrains the puppy and gives him hell with one fierce sting after another.  Puppy's playful attitude and unrelenting cuteness doesn't save him from Sir's swift hand as welt after welt is painted onto his body in fluid strokes.

04192015s1
04062015s2
22nd April 2015 04062015s2
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The boy is helplessly strapped down to the gurney and Sir is going to make the most of it.  The leather strap slaps down on his reddening ass but the boy's moans are barely audible through the bondage tape mask.  Then Sir makes him protest by striking his ass with the welting ball which builds up a fury of deep red hot pain.  When the boy can't take any more Sir returns to the strap and finishes with a face fucking.

04062015s2

Iron Lockup Updates

05162015s6

Kneeling on the wetroom floor, mostly naked except for boots, a hood and his chains the prisoner awaits Sir with a rock hard erection.  Sir taunts the sub with a little cock and ball torture but what he really wants is to ram his cock deep inside the prisoner's throat and make him choke on it.  The prisoner only gets hornier and begins to eat Sir's cock with hungry enthusiasm.

Play
29th July 2015
4.00
05162015s5

Helpless against Sir's teasing of his cock the prisoner moans and jerks in vain as Sir violates his ass with his fingers. Sir releases his hands and the prisoner begins edging himself while still inverted.  With Sir's finger back in his ass the prisoner blows his load onto his own face.  

Play
24th June 2015
4.00
05162015s4

The prisoner swings back and forth as the pressure begins to build in his face.  His boots strapped are to the ceiling and his arms bound up by his chest as Sir teases his cock, foreshadowing the tease to come.  Lubing up his gloved hand Sir prepares to violate the prisoner's ass as the prisoner rocks helplessly upside down.

Play
17th June 2015
4.00
05162015s3

Standing like a mighty tree the prisoner's cock remains hard enough to pop.  Sir teases the tip which is already over stimulated and then he begins to reinsert the dong into the prisoners ass, making him move against his restraints.  Sir's hand goes full force on the prisoner's cock till it becomes too much and showers of cum flood out and drench his thighs. 

Play
10th June 2015
4.00
05162015s2

In a long leather, chain, and straight jacket suspension the prisoner lies back with his cock standing at full attention.  He squirms against his bindings and awaits whatever evil Sir has planned for him.  After a long period of anticipating Sir begins to finger the prisoner's ass making the prisoner squirm more violently and moan with each stimulation.

Play
3rd June 2015
4.00
05162015s1

Securely confined in a straight-jacket, the prisoner has no chance of escape from the start.  And he's naked from the waist down so his cock hangs out ready to be manhandled.  Sir Pan lays the prisoner flat on the gurney and his cock goes hard immediately.  He slowly prepares to raise the prisoner into the air where he will be at the full mercy of Sir Pan's devious whims.

Play
27th May 2015
4.00
05042015s2

Still wet from his golden shower the boy continues to service Sir's rock hard cock.  He braces himself against the bars of the cell as Sir forces him to deepthroat his cock.  With long snowy bursts Sir covers the boy in his cum, wiping his hand off on the boy's head.

Play
20th May 2015
4.00
05042015s1

The boys eyes are transfixed on Sir as he orders him to open up and deep throat his nightstick.  The boy is then bent over the prison toilet and made to take a beating to his junk and ass.  Sir then face fucks the boy but instead of cumming he showers the boy in piss.  

Play
13th May 2015
4.00