Feature Slide

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29th January 2015 12262014s4 Coming Soon

And now for something completely serious: a puppy tickle torturing an innocent victim stuck to the spiderweb.  Puppy utilizes a pinwheel, a claw, and his teeth to make the prisoner scream (in horror or delight it's hard to say).  When the bamboo cane and the chair come out the prisoner gives a look of confusion, that is till he finds his feet propped up and caned.  

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12262014s3
22nd January 2015 12262014s3
Featuring:
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In a full straight jacket and chain suspension the prisoner is subjected to rough impact play as his legs flail in the air causing the chains to bite him mercilessly.  The prisoner remains rock hard through the torment.  Sir comes back, lube in hand, and begins to tease the prisoner's prostate. 

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12262014s2
15th January 2015 12262014s2
Featuring:
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Completely blind and restrained in a straight jacket the prisoner is uncomfortably chained to the ceiling, helpless against Sir's will.  The prisoner's cock at is at full attention as Sir begins to painfully tease him.  With a short break from the torment the prisoner struggles against the restraints, reminding himself that he is screwed.  Sir returns, armed with a flat fiberglass batten that stings the prisoner's thighs and balls.  Looking to potentially leave welts Sir then upgrades to a thin bamboo reed.

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12262014s1
8th January 2015 12262014s1 Play

Hands chained to the ceiling and facing each other the boy and prisoner try not to move lest they lose their noses.  Tied together by a pair of nose shackles they are subjected to Sir's torments with each reflexive motion turning into a painful tug.  Sir then gives them a challenge to complete but doing so could have painful consequences.

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12062014s3
1st January 2015 12062014s3
Featuring:
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With the cold of the chain spiderweb at his back the prisoner humps the air, waiting for whatever evil Sir has in mind but the foreplay doesn't last as Sir begins to secure the nose shackle to his septum.  He is ordered to edge himself but every stroke tuggs painfully at his nose until the prisoner blows a huge load.

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12062014s2
25th December 2014 12062014s2
Featuring:
Play

Bound and twitching with the rise and fall of the electronic current the prisoner remains defenseless against Sir's cruelty.  The wartenburg wheel sends a sharp sting of electricity through the boy as it traces his legs, perineum and balls.  Sir puts the boy's moaning to good use and clips a microphone to his mask turning every little whimper into an electric blast in his cock.  

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12062014s1
18th December 2014 12062014s1
Featuring:
Play

This first time prisoner's nerves are clearly worked up as he gets chained to the comfy chair. Sir warms him up with the threat of striking his chest and proceeds to tease his nipples. The boy starts to get really uncomfortable when the electrified pinwheel start to trace his body but the boy doesn't really start moaning till his dick gets charged.

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08172014s17
11th December 2014 08162014s17
Featuring:
Play

The prisoner takes a few minutes between scenes to play with his cock.  Waiting to cum in hopes that the next scene would force him to. 

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08162014s16
4th December 2014 08162014s16
Featuring:
Play

These prisoners are getting very fond of each other.  Both fighting to stay on the small prison bed they devour each other's cocks, stroking and deep throating like old friends or frat brothers.

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08162014s15
27th November 2014 08162014s15
Featuring:
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Armed with a dildo large enough to be considered an arm the prisoner penetrates himself and works toward his next orgasm.

08162014s15

Iron Lockup Updates

12262014s3

In a full straight jacket and chain suspension the prisoner is subjected to rough impact play as his legs flail in the air causing the chains to bite him mercilessly.  The prisoner remains rock hard through the torment.  Sir comes back, lube in hand, and begins to tease the prisoner's prostate. 

Play
22nd January 2015
4.00
12262014s2

Completely blind and restrained in a straight jacket the prisoner is uncomfortably chained to the ceiling, helpless against Sir's will.  The prisoner's cock at is at full attention as Sir begins to painfully tease him.  With a short break from the torment the prisoner struggles against the restraints, reminding himself that he is screwed.  Sir returns, armed with a flat fiberglass batten that stings the prisoner's thighs and balls.  Looking to potentially leave welts Sir then upgrades to a thin bamboo reed.

Play
15th January 2015
4.00
12262014s1

Hands chained to the ceiling and facing each other the boy and prisoner try not to move lest they lose their noses.  Tied together by a pair of nose shackles they are subjected to Sir's torments with each reflexive motion turning into a painful tug.  Sir then gives them a challenge to complete but doing so could have painful consequences.

Play
8th January 2015
4.00
12062014s3

With the cold of the chain spiderweb at his back the prisoner humps the air, waiting for whatever evil Sir has in mind but the foreplay doesn't last as Sir begins to secure the nose shackle to his septum.  He is ordered to edge himself but every stroke tuggs painfully at his nose until the prisoner blows a huge load.

Play
1st January 2015
5.00
12062014s2

Bound and twitching with the rise and fall of the electronic current the prisoner remains defenseless against Sir's cruelty.  The wartenburg wheel sends a sharp sting of electricity through the boy as it traces his legs, perineum and balls.  Sir puts the boy's moaning to good use and clips a microphone to his mask turning every little whimper into an electric blast in his cock.  

Play
25th December 2014
4.00
12062014s1

This first time prisoner's nerves are clearly worked up as he gets chained to the comfy chair. Sir warms him up with the threat of striking his chest and proceeds to tease his nipples. The boy starts to get really uncomfortable when the electrified pinwheel start to trace his body but the boy doesn't really start moaning till his dick gets charged.

Play
18th December 2014
4.00
08172014s17

The prisoner takes a few minutes between scenes to play with his cock.  Waiting to cum in hopes that the next scene would force him to. 

Play
11th December 2014
4.00
08162014s16

These prisoners are getting very fond of each other.  Both fighting to stay on the small prison bed they devour each other's cocks, stroking and deep throating like old friends or frat brothers.

Play
4th December 2014
4.00