#12282010

12282010

Shirt Size: 

Medium

Pants Size: 

33/32

Boot Size: 

10.5

Asshole: 

Tight

Limits: 

None

Notes: 

Bad Behavior: Was able to free self from Leg Irons - High Security Needed

Rating: 

4.57143
Average: 4.6 (7 votes)

Video Scenes

05162015s7

The prisoner patiently waits, chained to the urinal, for Sir's return but his patience is rewarded by being stepped over as Sir goes to piss right in front of his face.  Once finished Sir turns to face fuck the cock hungry prisoner.  The toe of Sir's boot then finds it's place on a helpless cock as he works toward a howling orgasm.

Play
8th July 2015
3.00
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
1st 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
4.50
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
12262014s6

Fully bound in a heavy duty straight jacket the prisoner is teased before being forced to take Sir's cock.  

Play
11th February 2015
4.00
12262014s5

The prisoner, still tied to the spider web, is still plenty feisty and the puppy shows him no mercy as he tortures his feet.  Laughter erupts along with pleading whimpers as puppy works to keep the prisoner's feet still, the caine stinging in sudden bursts.  The prisoner refuses to hold still and puppy responds with distraction and unexpected strikes, making the prisoner dance with joyful fear.  When the time comes to give the feet a rest puppy reverts biting, tickling, knife play and ball slapping.

Play
4th February 2015
4.00
12262014s4

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.  

Play
28th January 2015
4.00
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
21st 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
14th 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
7th January 2015
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
3rd December 2014
4.00
08162014s14

With time to kill one of our prisoners takes to teasing the other's cock, sometimes jacking hard, sometimes teasing lightly.  He squeezes and stretches his balls, polishes his head, and tickles his shaft.  

Play
19th November 2014
4.00
08162014s13

What was supposed to be a very serious forced workout scene turned into a hyper-competetive farce as the mostly naked prisoners fail to one up each other through their sets, stumbling on almost every exercise.  Puppy is then forced to keep them moving by stinging their asses with a fine carbon fiber rod that gets them unleashing profanities as they try to keep pace.  

Play
12th November 2014
4.00
08162014s8

Our two prisoners find themselves with a little downtime between scenes and despite plenty of play during their visit they can't keep their hands (and mouths) off each other.  

Play
8th October 2014
4.00
08162014s5

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. 

Play
24th September 2014
5.00
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
3rd 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
27th August 2014
5.00
10272013s1

Sir Pan has a new toy, and he needs someone to try it out.  It's homemade, and he isn't completely sure it will stay bolted to the wall...  Luckily prisoner #12282010 has been volunteered to assist.  Sir Pan chains him to the spinning octagon and rotates him upside-down, waiting to see if anything will break.  And as a thank you for helping out, Sir Pan very nicely beats up the prisoner with another new toy.

Fetishes:
Play
20th November 2013
4.00
10272013s2

Sir Pan tests out his new piece of gear, a custom made 7'6" diameter rotating steel octagon on Prisoner #12282010. The Prisoner is suspended by chain to the octagon and fucked with while being inverted several times - strapped in painfully by heavy steel chain. Eventually Sir Pan allows the Prisoner to cum while inverted and he blows a huge load all over his own face. 

Fetishes:
Play
13th November 2013
4.00

After some CBT and choking Prisoner #12282010 is ordered to jack off Sir Pan in the cell until Sir Pan blows a massive load all over the Prisoner and his cell. 
Sir Pan then pins the Prisoner's neck against the cell bars and requires the prisoner to jack himself off until he cums with a huge load shooting across the prison hall.

Fetishes:
Play
18th July 2013
4.00

Sir Pan chains Prisoner #12282010 spread eagle to the trough urinal and wall starts in on some CBT. Sir Pan then adds a harsh heavy steel ball crusher to the Prisoner's ball sac and pulls it to the wall with heavy chain. Watch the Prisoner squirm as he helplessly tries to ease the pain in his balls.

Play
11th July 2013
4.00
08072012s2

Instead of releasing the prisoner Sir Pan escorts him into the wet room and chains him to the comfortable chair.  Having his balls stuffed in the ball crusher makes the prisoner's cock hard.  The e-stim on his balls just makes him harder, then the prisoner is required to edge himself while Sir Pan stands by to watch.

Play
27th June 2013
5.00
08072012s1

Chained at the neck, wrists and ankles, prisoner #12282010 is zipped inside a body bag.  This confinement is intense. At long last the prisoner's cock is exposed and he is rewarded with a quick ball squeezing.

Play
20th June 2013
5.00
07032012s4

Prisoner #12282010 is brought into the wet room where a sling hangs ready.  He climbs in and Sir Pan proceeds to fuck him with a baton.

Play
6th June 2013
4.00
07032012s2

Sir Pan chains the prisoner standing in the center of the room, then ensures he won't be moving by plugging his ass with the anal hook.  Then Sir raises the height so the prisoner must stand on his tiptoes.  Sir edges him for almost an hour before removing the hook and denying the prisoner permission to cum.

Play
30th May 2013
4.75
07032012s1

Sir Pan chains a straight-jacket-wearing prisoner to the spider web and the prisoner's cock goes rock hard.  He writhes as Sir Pan slowly introduces new toys.  The prisoner is left, head covered, with no idea what to expect, until Sir Pan returns and moves him to the center of the room.  What will happen next?

Play
23rd May 2013
5.00
06112012s2

Sir Pan chains the prisoner to the bed then fucks him with his baton, through the cell bars.  Sir changes the prisoner's position so he can get a better hold on his cock, then resumes fucking him.  Between the chains and the fucking, prisoner #12282010 is clearly in ecstasy. 

Play
25th April 2013
4.00
06112012s1

Naked and blindfolded, prisoner #12282010 is chained inside a cell.  His prick gets hard immediately but he is made to wait.  Finally Sir Pan returns and rewards him with some cbt, not once but twice.  Then he eagerly deep-throats Sir's nightstick. 

Play
18th April 2013
4.00
05212012s2

After having his ass thoroughly warmed up prisoner #12282010 is fucked by Sir’s nightstick and then takes a massive dong.  Sir is sure to reward the boy’s good behavior with CBT.

Play
4th April 2013
3.00
05212012s1

Prisoner #12282010 finds himself in thick heavy chains and takes several different dongs up his ass.

Play
28th March 2013
5.00
04302012s3

The chain cage proves uncomfortable, but that doesn’t mean we took it off.  Instead the prisoner finds himself in total darkness only to be released after deep throating Sir’s baton. 

Play
7th March 2013
5.00
04302012s2

Having been warmed up with Sir’s night stick prisoner #12282010 takes a massive dong up his ass.  Once his ass has had enough he is required to stand, locked into a cold, pinchy chain cage.

Play
28th February 2013
5.00
04302012s1

Prisoner #12282010 returns only this time he finds himself chained up in the wet room.  He deep throats Sir’s night stick and then take it up his tight asshole. 

Play
21st February 2013
4.00
04152012s4

The psychological journey for prisoner #12282010 is almost at it’s end.  Balls stretched, nipples tweaked and groin shocked this scene takes a turn towards masturbation however only if the prisoner can reach his dick without pulling his balls off.

Play
13th February 2013
4.00
04152012s3

Prisoner #12282011 has his daydream interrupted as Sir stretches his ... ahem ... “imagination”.

Play
6th February 2013
3.00
04152012s2

For prisoner #12282010 being chained up between the cells in the prison is a practically out of body experience as he is left in total isolation, senses cut off from the outside world.  All he knows is the pinch of the chains and the cold rough concrete scratching at his back.

Play
30th January 2013
4.50
04152012s1

Everyone’s favorite short bitch takes a big swig of piss, deepthroats Sir’s cock, gets hard fucked, and is ordered to jack of his tiny bitch dick.

Fetishes:
Play
23rd January 2013
4.00
03182012s2

One of our more bizarre fantasies has somehow manifested itself in this long iron restraint scene.  Our favorite bottom finds himself still chained to the urinal with his balls in a clamp and his nipples being pinched and stretched.  Someone once told me that if you slapped a boys balls enough he will cum… apparently it’s true.

Play
13th December 2012
4.00
03182012s1

We got him by the balls!  Well, we got him by everything, but the balls are just so much more interesting and boy does it make him squirm.

Play
6th December 2012
3.00
03112012s2

After spending over an hours in “la la land” our subject is ready for some CBT.

Play
29th November 2012
4.00
03112012s1

There’s nothing like hyperbolically thorough bondage!

Play
22nd November 2012
4.00
12042011s2

Prisoner #12282010 is enjoying being chained down too much so Sir decides some punishment is in order.  The inmate is then milked and released.

Play
24th May 2012
4.00
12042011s1

Thoroughly chained to the gurney prisoner #12282010 has nothing to do but edge himself.  

Play
17th May 2012
4.00
10012011s6

Upon arrival prisoner #12282010 showed us his large collection of straight jackets… how could we say no?

Play
2nd February 2012
4.00
10012011s5

Left alone in cell one, locked in iron chains prisoner #12282010 spends hours in icy confinement.

Play
26th January 2012
4.00
10012011s4

Puppy comes to play with the inmates.  Prisoner #12282010 spends the scene the way he likes it, tightly bound and left in the corner while #12122010 gets whipped and caned.  What #12122010 doesn’t know is that #12282010 is wired into a sound activated electro unit that shocks his cell mate every time he screams.

Play
19th January 2012
5.00
10012011s3

Confined together in cell 1 Prisoners #12122010 and #12282010 are given the rare privilege to play with themselves and get off and, of course, prisoner #12122010 wastes no time getting started in using this rare freedom.  He masturbates viciously and then fucks himself with a large dong.  It doesn’t take prisoner #12282010 to join in the fun. 

Play
12th January 2012
4.00
10012011s2

Chained in the wet room prisoners #12122010 and #12282010 share a peaceful silence till Sir enters to feed #12122010 his piss.  

Play
5th January 2012
4.00
10012011s1

In this dual intake scene prisoners #12122010 and #12282010 receive a cavity search and #12202010 takes cbt while #12122010 gives Sir head.  Sir cums into the bitch’s hungry mouth.  Sir then gives permission to sub #12202010 to masturbate onto his inmate.

Play
29th December 2011
5.00
01292011s2

A rare simultaneous scene ensues.  Sir, disappointed that the small inmate had gotten off in the night without a mask on decides that punishment is in order while the Puppy challenges #12282010 to escape from his bondage.

Play
22nd September 2011
4.00
01292011s1

Prison intake.  Two inmates are inspected then the small one is required to lie down in the cold urinal and take Sir’s piss.  After a cavity search they are locked into cell 1 together.  The small one then searches for a place to put his dildo and finds the emergency escape hatch a perfect spot and proceeds to fuck himself.

Play
14th September 2011
4.00
12282010s5

Meat tenderizing says it all.  Sir Pan handcuffs the prisoner on a long chain in the wet room and handles him all over.  The prisoner can move around the room but he is at the mercy of Sir Pan's hands.

Play
7th September 2011
4.00
12282010s4

The prisoner is locked in a jail cell where he masturbates to pass the time.  He even finds a dirty old magazine somewhere to wank to.  And somehow he squeezes some piss out of his hardon too.

Fetishes:
Play
31st August 2011
4.00
12282010s3

After getting to enjoy Sir Pan's hospitality, the prisoner is forced to clean the wet room with only a tiny scrub brush.  His cock hangs out for all to see as he traverses the room on his knees.  At last he is allowed a shower, with Sir Pan standing by.

Fetishes:
Play
24th August 2011
4.00
12282010 scene 1

Confined in a gas mask right from the start prisoner #12282010 is spends some alone time in the wet room.

Play
18th August 2011
4.00

Photo Sets

Sir Pan chains a straight-jacket-wearing prisoner to the spider web and the prisoner's cock goes rock hard. He also gets to enjoy an anal hook in his ass and the sling.

View
7th June 2013
4.00

Prisoner #12282010 finds himself chained to the urinal contemplating life's mysteries.

View
16th May 2013
4.00

Prisoner #12282010 finds himself chained to the urinal.  Best he doesn't struggle given that his balls are chained to his legs.

View
9th May 2013
5.00