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25:03 Jail guard gets some head, then a threesome by iluvhead on Feb 09, 2012 310,549 views and 114 likes

16:07 Jail Mates fucking with hot wax by prisonMaster on Feb 19, 2012 23,732 views and 10 likes

05:07 Inmates bumping uglies in a jail cell by xxxdewild on Aug 17, 2012 12,422 views and 3 likes

05:06 Black porn in jail super hot by lukkepra on Nov 11, 2011 34,131 views and 18 likes

16:49 Guy gets head threw a jail cell by seemybutt on Jul 21, 2011 61,448 views and 30 likes

10:05 Just out of jail by twinkletoes on Nov 22, 2011 240,748 views and 41 likes

29:35 Jail baits having an orgy by prisonMaster on Feb 20, 2012 65,481 views and 34 likes

09:15 Prison Guard Pounds Inmate In Jail Cell by osospolicias on Oct 08, 2012 50,635 views and 19 likes

04:34 Jail Cell Gloryhole Hardcore by lnight03 on Jan 21, 2013 30,691 views and 11 likes

19:30 Hairy guy fucked in jail cell by eatmeout on Sep 14, 2011 67,437 views and 17 likes

40:49 Hazed pledges wrestle in jelly and get fucked by HazeGuy on Apr 11, 2012 1,051,509 views and 176 likes

04:47 t-femanine Julia London by blueorchid on Mar 16, 2013 86,966 views and 2 likes

04:14 Julio Jimenez and Draven Torres fucking by blubfrut on Mar 08, 2013 1,077 views

05:18 Skinny Latin tranny has a jolly ass ride by pim8roller on Jan 12, 2013 212 views

05:17 tranny has a jolly assride by pim8roller on May 10, 2013 views

05:16 tranny has a jolly assride by pim8roller on Jan 12, 2013 1,135 views and 1 likes

05:17 guy tranny has a jolly assride by pim8roller on Jan 05, 2013 185 views

05:19 guy tranny has a jolly assride by pim8roller on Nov 13, 2012 490 views

05:17 guy tranny has a jolly assride by pim8roller on Feb 21, 2013 1,128 views

00:20 Jerk Off to Jewel by TheLeader25 on Oct 10, 2012 143 views

00:20 Mounting the legendary Jelly Kong by VaFFMedic on Oct 18, 2012 148 views and 1 likes

00:20 Mounting the Jelly Kong by VaFFMedic on Mar 14, 2013 72 views and 1 likes

05:20 guy tranny has a jolly assride by pim8roller on Apr 01, 2013 2,023 views

05:21 Teen tranny has a jolly assride by pim8roller on Jan 11, 2013 600 views

05:16 tranny has a jolly assride by pim8roller on Mar 14, 2013 1 views

32:15 Prison Master lays down the law by prisonMaster on Feb 21, 2012 41,181 views and 27 likes

06:12 A gay guide to passing time in prison by sharon1974 on Aug 21, 2012 22,803 views and 11 likes

00:31 What Happens On The Bus by johnty on May 10, 2011 23,689 views and 9 likes

16:09 Hairy office solo by greatgreyjay on May 27, 2011 112,133 views and 21 likes

17:32 pretty blonde guy deep throats cock like a pro by seemybutt on Jun 05, 2011 43,100 views and 19 likes

17:40 2 Latinos fuck by eatmeout on Sep 15, 2011 14,174 views and 6 likes

24:22 Breaking and entering by cowboycam on Sep 18, 2011 79,276 views and 78 likes

23:58 Stripped searched by cowboycam on Sep 20, 2011 94,545 views and 69 likes

05:11 Cop Thrashes Skater by Alternadudes on Dec 29, 2011 83,388 views and 51 likes

09:58 Just another day in the gay ghetto by bigBANGtheory69 on Feb 03, 2012 52,326 views and 45 likes

20:01 3 way inmate fuck fest in a small prison cell by mathewg on Feb 03, 2012 241,927 views and 102 likes

20:22 Guard falls for the prisoner and fucks by SupaGayMan on Feb 23, 2012 100,354 views and 34 likes

14:25 Collection of Men.com Hotties w/ Great Bodies by tobitickle on Jun 14, 2012 82,489 views and 33 likes

04:17 Drake Hanson and Zac Zaven in intense by blubfrut on Jan 16, 2013 2,208 views and 1 likes

05:24 Nasty bi prisoners by lustylucy on Feb 19, 2013 33,297 views

16:21 Prison Fuck HQ With Gorgeous Men WOW by shadow8 on Feb 21, 2013 86,943 views and 58 likes

07:29 3D prisoners having anal sex by h0wdyp45 on Mar 26, 2013 5,966 views and 3 likes

04:26 3D prison threesome by dpaulnr3 on Mar 30, 2013 4,116 views

07:48 Cop fucks his offender in cell by marinvulle on Apr 02, 2013 168,578 views and 21 likes

05:23 Respect His Authority! by kaylakink on Apr 14, 2013 25,477 views

05:16 User Upload Untitled by blubfrut on Apr 11, 2013 128 views

05:23 User Upload Untitled by kaylakink on Apr 03, 2013 110 views

04:47 beautiful tranny sexy tease show by blueorchid on Mar 29, 2013 22,466 views and 1 likes

06:09 Lucas the Latino Santa Clause sucks cock by genderb on Dec 24, 2011 36,089 views and 7 likes

02:09 Gay sex in the woods - with a theme song! by iridebotton111 on Feb 23, 2012 327,937 views and 10 likes