Gay Prison Men, Man Prison Cock - CockFilledMen.com

Updated: December 1st, 2025

Ramming Riley

amateur 2:01
Twinks Prisoners Get Ass Punished

twinks 5:00
06232013s4

bdsm 2:06
Bears Fuck In Prison

bears 1:51
Puppy Prisoner

bdsm 2:06
Stake Out Part 2 - STG - Str8 to Gay - Bryce Star & Haigen Sence

couples :57
Prison Guard Fucked!

anal, bisexual, group 9:57
Broke Straight Boys - Jason and Anthony

straight boys 5:00
taking advantage of a twink inmate

hardcore 1:04
big bear sucks cock and gets fucked

blowjobs, masturbation, cumshot, anal, bears, hunks 1:00
Jake Steel and Scott Campbell

hardcore 1:06
Prison Shower 4 - DMH - Drill My Hole - Johnny Rapid - Landon Conrad - Cooper Reed

anal, asslicking, big cock, blowjobs, group, hardcore, hunks, twinks 1:04
Guard-Prisoner ORGY

hardcore 2:03
Prison Shower 4 - DMH - Drill My Hole - Johnny Rapid - Landon Conrad - Cooper Reed

hardcore 1:04
Prison Fuckers

bareback, blowjobs, masturbation, anal, hardcore 2:09
Military Twinks Fuck Prisoners

outdoor :55
Prison Banging

bareback 2:02
Raw Attitude

asslicking, bears, blowjobs 2:39
Lawless

fisting, hardcore, pornstars 2:00
Zipped UP

bdsm 2:06
Jail Fuckers

amateur, bareback, anal, hardcore 1:07
Chained Up Prisoner

bdsm 2:06
Naughty Prisoner Fucked with Baton

bdsm 2:06
Prisoner #12282010 Gets Fucked

bdsm 2:06
prisoner and the guard

twinks 5:00
Jail Ass Licker

asslicking, jocks, masturbation 2:00
Prison Sex

interracial 7:32
interracial cock sucking and jerking

interracial 1:30
Stake Out Part 2 - STG - Str8 to Gay - Bryce Star & Haigen Sence

couples :57
Ramming Riley

amateur 2:01
Ramming Riley

amateur, anal, bareback 2:01
Zoltan and Kalman

bareback, blowjobs, masturbation, anal, hardcore 2:00
E-stim

bdsm 2:06
Raw Attitude

bears 2:39
Confused Prisoner

bdsm 2:06
Military Twinks Fuck Prisoners

outdoor :55
Raw in Reno

amateur 2:34
Chained Up

amateur, muscle, masturbation 17:24
Military Prisoners

amateur, military, hardcore 1:48
Arab Wrapped Cock Pounding Ass

couples 5:05
Chained and Forced to Suck

bdsm 2:06
Zipped UP

bdsm 2:06
Prison Threesome

bareback, jocks, blowjobs, masturbation, cumshot, anal, group, hardcore 18:26
Crazed Prison Sex

muscle, group, hardcore 2:01
big bear sucks cock and gets fucked

blowjobs, masturbation, cumshot, anal, bears, hunks 1:00
Two Horny Captive Twinks

group 5:00
Prison Riot

group 9:57
Twink Prisoner

twinks, blowjobs, anal 10:38
Arab Wrapped Cock Pounding Ass

anal, couples, hunks, masturbation 5:05
Gay Cop Punishes Prisoner BDSM Sex

anal, bdsm, blowjobs, group 4:00
Guard-Prisoner ORGY

anal, big cock, blowjobs, group, hardcore, hunks, muscle 2:03
Larry

muscle, masturbation, fucking machines, hunks, hairy 1:30
Under Arrest

anal, group, hardcore 2:00
JAIL CELL JERK OFF

masturbation, straight boys, hunks 5:00
Tied Up Prisoner

bdsm 19:00
Prisoners Fucked

asian 3:50
Chained Up Prisoner

bdsm 2:06
Prisoner Life

outdoor 1:44
Prisoners Excellent Outdoor Hard Fucked Action

outdoor 3:00
Danny

cumshot 1:30
Prisoned Boys

asslicking, muscle, hunks 8:17
Jailhouse Fucking

muscle, group, hardcore 18:26
Prison Shower 2 - Studs Fuck

group 1:02
Puppy Prisoner

bdsm 2:06
Confused Prisoner

bdsm 2:06
Prisoners Excellent Outdoor Hard Fucked Action

latino 3:00
Raw in Reno

amateur 2:34
prisoner gang fuck

twinks, blowjobs, bdsm 1:01
My Little Prisoner

dildo, hardcore, bdsm 15:02
Prison Threesome

amateur, bareback, blowjobs, anal, group, hardcore 15:07
Punishing A Prisoner

asslicking, bears, military 9:57
Man Behind Bars

hairy 2:00
Jail Bangers

hardcore 26:04
Prison Riot

bareback 3:05
Prison Sex

group 2:04
Prisoners Get Punished

bdsm 5:00
Prison Cellmates

hardcore 11:48
Police Man

bdsm 2:00
Prison Slave Fuck

bdsm 2:03
Broke Straight Boys - Jason and Anthony

straight boys 5:00
Gay Enjoyed In

anal, cum eating, voyeur 3:55
Redhead Sexy Corrections Officer Strokes His Big Meat

hunks, masturbation, military, muscle 4:07
Naughty Prisoner Fucked with Baton

bdsm, toys 2:06
Stake Out Part 2 - STG - Str8 to Gay - Bryce Star & Haigen Sence

anal, couples, hardcore :57
Broke Straight Boys - Jason and Anthony

anal, straight boys, twinks 5:00
Grindhouse Episode 2 - NakedSword Originals

muscle, big cock 2:05
Dreaming About Getting Out

twinks, blowjobs, anal 4:56
Richard B and Atilla M

bareback, blowjobs, masturbation, anal, hardcore 2:00
Military Punishes Prisoners

blowjobs, military, bdsm 5:00
Cop Uses His Prisoner

muscle, blowjobs, bears, military, hardcore 16:41
Bound Prisoner Examined

muscle, hunks, bdsm 5:18
Prison Gangbang

hardcore 2:01
Prison Riot

group 9:57
Prison Shower 2 - Group Sex

group 1:02
Piss Bitch

bdsm 2:06
Prisoner #12282010 Gets Fucked

bdsm 2:06
cops In Need

hairy 1:37
Broke Straight Boys - Jason and Anthony

straight boys 5:00
Redhead Sexy Corrections Officer Strokes His Big Meat

hunks 4:07
Piss Bitch

bdsm 2:06
Fantasy Prison Fuckfest

anal 1:27
Stake Out Part 2 - STG - Str8 to Gay - Bryce Star & Haigen Sence

couples :57
Ramming Riley

amateur 2:01
Larry

fucking machines 1:30
Mischivious Doctor

bdsm 4:01
Prisoners Fucking

anal 1:27
Gay Cop Ties Prisoner and forces Blowjob

bdsm 4:00
Guard-Prisoner ORGY

hardcore 2:03
prisoners of fuck

twinks, group, bdsm 5:00
Holding Cell

asslicking, jocks, toys, masturbation, object insertion 5:00
Military Twinks Fuck Prisoners

group, jocks, military, outdoor, twinks :55
Franco Fucks My Mouth

blowjobs, fucking machines, cumshot, hairy, stripping 1:30
Prison Punishment - Karl - The Rod

straight boys, bdsm 1:26
Arabian Prison Alexander Pictures

bears, latino 5:05
PRISON CUM SHOT

masturbation, straight boys, voyeur 2:22
Huge strong man

bareback, blowjobs, masturbation, anal, group, straight boys, hardcore 3:59
Boning In Prison

interracial, blowjobs, anal 13:21
Tiny Prison Bitch

blowjobs, anal, hardcore 12:29
Inmates Hard Fucking

muscle, anal, hardcore 18:19
Fucked On The Prison Toilet

cumshot, anal, hardcore 18:55
Prison Sex

blacks 15:20
Officer Fucks His Prisoner

hardcore 9:57
His First Internal

latino 3:31
Prison Breakers

amateur 2:58
Prison Bitch

amateur 1:00
Rikki Imprisoned

bdsm 7:48
Chained and Forced to Suck

bdsm 2:06
Gay Cop Punishes Prisoner BDSM Sex

bdsm 4:00
euro hunks with ink fucking in a barracks

military 2:00
06232013s4

bdsm 2:06
Prisoner Life

outdoor 1:44
Bareback Prisoner

bareback 1:12
Str8 Out Of Prison

amateur 1:46
Redhead Sexy Corrections Officer Strokes His Big Meat

hunks 4:07
Prison Shower 2 - Group Sex

muscle 1:02
Twinks Prisoners Get Ass Punished

twinks 5:00
E-stim

bdsm 2:06
Prison Bitch

anal, hardcore, hunks 1:07
Andrew

masturbation, fucking machines, cumshot, hairy, stripping 1:30
Prison Shower 2 - Drill My Hole - Johnny Rapid - Sebastian Young - Jack King

anal, group, hardcore, pornstars 1:02
LONELY NIGHTS IN THE STIR

muscle, masturbation, straight boys, hunks 5:00
Feeding On Cock

twinks, blowjobs, big cock 5:00
Arab Hunks Slapping Cocks Together

couples 5:05
Raw in Reno

amateur 2:34
Prison Shower 2 - Group Sex

anal, blowjobs, group, masturbation, muscle 1:02
Big Bears In Trouble

anal, bears, big cock, blowjobs, hardcore, object insertion 1:48
Prisoners Last Request

blowjobs, bears, hardcore 17:17
E-stim

bdsm 2:06
Prison Sex with

cumshot, anal, cum eating 17:30
Basement prison

bareback, blacks, blowjobs, masturbation, anal, hardcore 3:59

Browse Our List

Browse Our List

Our Good Friends