Most Popular Prison Sissy Videos

  • I Want To Be a Sissy Subliminal Programing

    I Want To Be a Sissy Subliminal Programing
    Views: 44854 Added: 28 Mar 13
    Time: 03:41 Tube: XHamster
    Tags: Shemales, Sissy

  • Sissy Slut in Motel

    Sissy Slut in Motel
    Views: 45155 Added: 28 Mar 13
    Time: 58:39 Tube: XHamster
    Tags: Hotel, Shemales, Sissy

  • La prison des fantasmes

    La prison des fantasmes
    Views: 167823 Added: 12 Jul 13
    Time: 10:17 Tube: XVideos
    Tags: French, Jail, Prison

  • Sissy sexy leather outfit 1

    Sissy sexy leather outfit 1
    Views: 16584 Added: 14 Jan 13
    Time: 01:04 Tube: XHamster
    Tags: Leather, Sexy, Sissy

  • K3: Prison of Hell

    K3: Prison of Hell
    Views: 10241 Added: 8 Mar 13
    Time: 02:32 Tube: XHamster
    Tags: Bdsm, Prison

  • Annamalice Sissy Self Hypnosis #813 - Lingerie Suck

    Annamalice Sissy Self Hypnosis #813 - Lingerie Suck
    Views: 40307 Added: 12 Jul 13
    Time: 03:11 Tube: XVideos
    Tags: Amateur, General, Lingerie

  • Most prisons

    Most prisons
    Views: 4360 Added: 4 Mar 13
    Time: 05:22 Tube: H2Porn
    Tags: Bdsm, Bondage, Domination

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    Properly trained white sissy
    Views: 45757 Added: 22 Feb 13
    Time: 00:15 Tube: XHamster
    Tags: Ladyboy, Shemales, Sissy

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    pegging a sissy
    Views: 2137 Added: 20 Oct 13
    Time: 02:43 Tube: XHamster
    Tags: Amateur, Bisexual, Femdom

  • Midget prisoners nailed the housewife

    Midget prisoners nailed the housewife
    Views: 48609 Added: 10 Apr 13
    Time: 21:14 Tube: RedTube
    Tags: Anal, Blowjob, Cumshots

  • Spank in prison

    Spank in prison
    Views: 282121 Added: 15 Feb 13
    Time: 04:32 Tube: H2Porn
    Tags: Extreme, Prison, Spanking

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    Views: 27447 Added: 22 Feb 13
    Time: 08:32 Tube: XHamster
    Tags: Ladyboy, Shemales, Sissy

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    A Sissy Made
    Views: 35891 Added: 20 Oct 13
    Time: 02:04 Tube: XHamster
    Tags: Cuckold, Femdom, Sissy

  • Sissy Sex Slave

    Sissy Sex Slave
    Views: 44854 Added: 28 Mar 13
    Time: 22:02 Tube: XHamster
    Tags: Shemales, Sissy, Slave

  • Busty prisoner used as sex slave

    Busty prisoner used as sex slave
    Views: 4360 Added: 4 Mar 13
    Time: 05:20 Tube: H2Porn
    Tags: Bdsm, Bondage, Busty

  • sissy bitch wendy jane fucks cyndee in the ass

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    Views: 7548 Added: 20 Feb 13
    Time: 12:17 Tube: XHamster
    Tags: Ass, Bitch, Fucking

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    Views: 14578 Added: 22 Feb 13
    Time: 03:31 Tube: XHamster
    Tags: Bitch, Ladyboy, Shemales

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    A Sissy Made Foot Milking
    Views: 72818 Added: 20 Oct 13
    Time: 02:25 Tube: XHamster
    Tags: Cuckold, Femdom, Foot fetish

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    Spanking prisoner
    Views: 7524 Added: 10 Dec 18
    Time: 20:05 Tube: XHamster
    Tags: 18 year old, Prison, Spanking

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    sissy big butt plug insertion
    Views: 4758 Added: 22 Dec 12
    Time: 00:19 Tube: XHamster
    Tags: Buttplug, Insertions, Sissy

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    Japanese Secret Women&,#039,s Prison part 4
    Views: 2159 Added: 20 Feb 13
    Time: 15:02 Tube: XHamster
    Tags: Asian, Babes, Japanese

  • White Chiffon Sissy Blouse

    White Chiffon Sissy Blouse
    Views: 18099 Added: 8 Mar 13
    Time: 15:32 Tube: XHamster
    Tags: Shemales, Sissy, White

  • Prisoner taken to medical facility

    Prisoner taken to medical facility
    Views: 201 Added: 10 Apr 13
    Time: 04:00 Tube: RedTube
    Tags: Bondage, Couple, Domination

  • Take That Strap-on Sissy

    Take That Strap-on Sissy
    Views: 201 Added: 10 Apr 13
    Time: 01:59 Tube: RedTube
    Tags: Lesbian, Sissy, Strapon

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    Sissy loser femdom handjob
    Views: 201 Added: 4 Mar 13
    Time: 05:25 Tube: H2Porn
    Tags: Bdsm, Bondage, Cfnm

  • Masked Sissy Sucker

    Masked Sissy Sucker
    Views: 201 Added: 22 Feb 13
    Time: 09:39 Tube: XHamster
    Tags: Gay, Mask, Sissy

  • Sissy Slut

    Sissy Slut
    Views: 14132 Added: 20 Feb 13
    Time: 15:52 Tube: XHamster
    Tags: Sissy, Slut

  • Japanese Women in prison (3)

    Japanese Women in prison (3)
    Views: 550 Added: 22 Feb 13
    Time: 18:48 Tube: XHamster
    Tags: Bdsm, Japanese, Lesbian

  • Prison Caning and Birching

    Prison Caning and Birching
    Views: 3156 Added: 22 Feb 13
    Time: 32:23 Tube: XHamster
    Tags: Caning, Prison, Spanking

  • Sissy gets to fuck mistress

    Sissy gets to fuck mistress
    Views: 43189 Added: 8 Mar 13
    Time: 31:10 Tube: XHamster
    Tags: Amateur, Cuckold, Fucking

  • Sissy Boy Spanked And Machined In The Ass

    Sissy Boy Spanked And Machined In The Ass
    Views: 8561 Added: 22 Feb 13
    Time: 13:45 Tube: XHamster
    Tags: Anal, Ass, Femdom

  • Sexy blonde prison warden with big tits gets

    Sexy blonde prison warden with big tits gets
    Views: 1556 Added: 10 Apr 13
    Time: 54:45 Tube: RedTube
    Tags: Blondes, Gangbang, Group sex

  • sissy captions

    sissy captions
    Views: 44854 Added: 22 Feb 13
    Time: 03:47 Tube: XHamster
    Tags: Ladyboy, Shemales, Sissy

  • Cruel Sissy Humiliation From Red Haired Princess

    Cruel Sissy Humiliation From Red Haired Princess
    Views: 45757 Added: 8 Mar 13
    Time: 04:41 Tube: XHamster
    Tags: British, Femdom, Humiliation

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    Russian guy with sissy crossdresser
    Views: 1188 Added: 14 Jan 13
    Time: 13:38 Tube: XHamster
    Tags: Crossdressing, Gay, Russian

  • Doing Something Naughty For Sissy Hubby

    Doing Something Naughty For Sissy Hubby
    Views: 271 Added: 12 Jul 13
    Time: 05:00 Tube: XVideos
    Tags: Big tits, Blondes, Busty

  • Busty police bitch gets shagged in prison

    Busty police bitch gets shagged in prison
    Views: 10233 Added: 27 Jan 13
    Time: 04:29 Tube: RedTube
    Tags: Big tits, Bitch, Blowjob

  • Mental Poison - Sissy Compilation

    Mental Poison - Sissy Compilation
    Views: 26062 Added: 20 Oct 13
    Time: 32:50 Tube: XHamster
    Tags: Compilation, Femdom, Sissy

  • Sissy Gives Head

    Sissy Gives Head
    Views: 13902 Added: 22 Feb 13
    Time: 01:32 Tube: XHamster
    Tags: Shemales, Sissy

  • sissy slave

    sissy slave
    Views: 6223 Added: 22 Feb 13
    Time: 05:08 Tube: XHamster
    Tags: Ladyboy, Shemales, Sissy

  • Cops humiliating and punishing prisoners

    Cops humiliating and punishing prisoners
    Views: 4059 Added: 4 Mar 13
    Time: 05:02 Tube: H2Porn
    Tags: Bdsm, Cfnm, Cop

  • Domina pegging worthless sissy

    Domina pegging worthless sissy
    Views: 3020 Added: 4 Feb 13
    Time: 05:05 Tube: DrTuber
    Tags: Bdsm, Brunettes, Domination

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    Chastity Mistress Femdom Humiliation cb6000 Slave Sissy fellow
    Views: 796 Added: 20 Oct 13
    Time: 00:51 Tube: XHamster
    Tags: Amateur, Bbw, Blondes

  • Sissy maid gets rammed

    Sissy maid gets rammed
    Views: 804 Added: 28 Mar 13
    Time: 02:10 Tube: XHamster
    Tags: Maid, Shemales, Sissy

  • Sissy Daddys stable

    Sissy Daddys stable
    Views: 13182 Added: 8 Mar 13
    Time: 00:50 Tube: XHamster
    Tags: Shemales, Sissy

  • Latin boys in prison shower

    Latin boys in prison shower
    Views: 3758 Added: 28 Mar 13
    Time: 11:48 Tube: XHamster
    Tags: Gay, Latina, Prison

  • Lesbian prisoner 2

    Lesbian prisoner 2
    Views: 34480 Added: 11 Jan 13
    Time: 11:02 Tube: RedTube
    Tags: Bondage, Domination, Fetish

  • The Sissy and Her Dominatrix

    The Sissy and Her Dominatrix
    Views: 5587 Added: 28 Mar 13
    Time: 16:21 Tube: XHamster
    Tags: Dominatrix, Ladyboy, Shemales

  • Cuckold femdom sissifies pathetic white guy

    Cuckold femdom sissifies pathetic white guy
    Views: 5432 Added: 15 Feb 13
    Time: 05:20 Tube: H2Porn
    Tags: Bdsm, Cuckold, Femdom

  • Sissy Chastity Slave Worships Feet

    Sissy Chastity Slave Worships Feet
    Views: 4427 Added: 15 Feb 13
    Time: 07:03 Tube: H2Porn
    Tags: Bdsm, Chastity, Domination

  • Kandi the sweet girl in prison

    Kandi the sweet girl in prison
    Views: 201 Added: 27 Jan 13
    Time: 04:59 Tube: RedTube
    Tags: Asian, Blowjob, Brunettes

  • 3D animated girl is getting gangbanged by a bunch of prisoners

    3D animated girl is getting gangbanged by a bunch of prisoners
    Views: 201 Added: 4 Feb 13
    Time: 04:31 Tube: DrTuber
    Tags: 3d, Animation, Anime

  • Blonde mistress wants to punish this sissy babe

    Blonde mistress wants to punish this sissy babe
    Views: 201 Added: 18 Apr 13
    Time: 01:43 Tube: PornerBros
    Tags: Babes, Bdsm, Blondes

  • in prison are the hard cocks

    in prison are the hard cocks
    Views: 201 Added: 22 Feb 13
    Time: 06:56 Tube: XHamster
    Tags: Dick, Prison, Vintage

  • Elegant sluts fucking prisoners

    Elegant sluts fucking prisoners
    Views: 201 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Blowjob, Fucking, Hardcore

  • prison gloryhole

    prison gloryhole
    Views: 201 Added: 14 Jan 13
    Time: 04:30 Tube: XHamster
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    Passionated giving blowjob sissy
    Views: 201 Added: 20 Oct 13
    Time: 01:44 Tube: XHamster
    Tags: Amateur, Blowjob, Dick

  • training sissy to suck dick sph joi

    training sissy to suck dick sph joi
    Views: 201 Added: 2 Dec 18
    Time: 15:01 Tube: XHamster
    Tags: Amateur, Bbw, Dick

  • Love Pecker - Sissy Self

    Love Pecker - Sissy Self
    Views: 201 Added: 20 Oct 13
    Time: 05:51 Tube: XHamster
    Tags: Dick, Femdom, Sissy

  • Sissy Boy's Ruined Orgasm

    Sissy Boy's Ruined Orgasm
    Views: 201 Added: 21 Jan 13
    Time: 21:49 Tube: DrTuber
    Tags: Anal, Bondage, Dildo

  • Femdom Starla Destroys Sissy Boys Ass

    Femdom Starla Destroys Sissy Boys Ass
    Views: 201 Added: 16 Feb 13
    Time: 06:20 Tube: H2Porn
    Tags: Anal, Ass, Bdsm

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    Cuckold sissy maid
    Views: 201 Added: 14 Jan 13
    Time: 09:00 Tube: XHamster
    Tags: Cuckold, Cumshots, Femdom

  • Hottie dresses her man as a maid and smacks him

    Hottie dresses her man as a maid and smacks him
    Views: 201 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Dress, Femdom, Maid

  • Hardcore orgy in the prison

    Hardcore orgy in the prison
    Views: 201 Added: 7 May 13
    Time: 03:00 Tube: TubeWolf
    Tags: Blowjob, Hardcore, Orgy

  • Prisoner nails the midget guardian

    Prisoner nails the midget guardian
    Views: 201 Added: 10 Apr 13
    Time: 22:43 Tube: RedTube
    Tags: Blowjob, Couple, Midget

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    Horny bisexual prisoners blowjob orgy
    Views: 201 Added: 4 Mar 13
    Time: 05:29 Tube: H2Porn
    Tags: Bisexual, Blowjob, Gay

  • Most prisons

    Most prisons
    Views: 201 Added: 15 Feb 13
    Time: 06:00 Tube: H2Porn
    Tags: Bdsm, Bondage, Domination

  • Two hot chicks fucking a dude in prison and he loves anal

    Two hot chicks fucking a dude in prison and he loves anal
    Views: 201 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Anal, Big tits, Boots

  • Sissy fun

    Sissy fun
    Views: 4025 Added: 20 Oct 13
    Time: 01:35 Tube: XHamster
    Tags: Amateur, Funny, Shemales

  • Prisoner Locked up by sensual Cop

    Prisoner Locked up by sensual Cop
    Views: 202 Added: 20 Oct 13
    Time: 16:22 Tube: XHamster
    Tags: Bear, Cop, Gay

  • Prison Tres Speciale Pour Femmes (1982) FULL VINTAGE MOVIE

    Prison Tres Speciale Pour Femmes (1982) FULL VINTAGE MOVIE
    Views: 4059 Added: 8 Mar 13
    Time: 12:02 Tube: XHamster
    Tags: Hairy, Milf, Prison

  • Cum Sissy

    Cum Sissy
    Views: 2417 Added: 20 Oct 13
    Time: 00:36 Tube: XHamster
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  • sissy training

    sissy training
    Views: 1611 Added: 22 Feb 13
    Time: 15:28 Tube: XHamster
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  • Dicklet Wax Torture

    Dicklet Wax Torture
    Views: 1386 Added: 21 Mar 13
    Time: 13:35 Tube: PornHub
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  • Pervert holds sluts prisoners in his basement fucking and using them forcing them to fuck

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    Views: 11537 Added: 21 Jan 13
    Time: 04:08 Tube: DrTuber
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    MY Alluring SISSY Cunt
    Views: 1777 Added: 20 Oct 13
    Time: 02:20 Tube: XHamster
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    Time: 13:31 Tube: XHamster
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    Views: 1812 Added: 8 Mar 13
    Time: 11:39 Tube: XHamster
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    Views: 811 Added: 20 Oct 13
    Time: 05:05 Tube: XHamster
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  • Nasty redhead cop takes care of some prisoners

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    Views: 1086 Added: 12 Jul 13
    Time: 05:01 Tube: XVideos
    Tags: Amateur, Anal, Babes

  • sissy maid gets own hole cleaned out after work - fisting

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    Views: 543 Added: 20 Oct 13
    Time: 01:34 Tube: XHamster
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    Time: 00:43 Tube: XVideos
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    Views: 3558 Added: 8 Mar 13
    Time: 04:53 Tube: XHamster
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    Views: 3837 Added: 4 Feb 13
    Time: 04:15 Tube: PornHub
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  • You want to be my sissy

    You want to be my sissy
    Views: 562 Added: 20 Oct 13
    Time: 02:14 Tube: XHamster
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    sanjon gorgeous sissy self suck
    Views: 2532 Added: 23 Dec 13
    Time: 39:10 Tube: XHamster
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  • Sissy Vicki pt1

    Sissy Vicki pt1
    Views: 5432 Added: 8 Mar 13
    Time: 03:42 Tube: XHamster
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  • Japanese Women in prison (5)

    Japanese Women in prison (5)
    Views: 2870 Added: 22 Feb 13
    Time: 11:45 Tube: XHamster
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  • Nasty redhead cop takes care of some prisoners

    Nasty redhead cop takes care of some prisoners
    Views: 4360 Added: 4 Mar 13
    Time: 05:00 Tube: NuVid
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  • Filthy blond gagged and bound in prison

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    Views: 4087 Added: 8 Mar 13
    Time: 19:28 Tube: XHamster
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    Views: 595 Added: 20 Oct 13
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  • Two amazing sluts talk to a prisoner

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    Views: 301 Added: 4 Feb 13
    Time: 04:47 Tube: DrTuber
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  • Mistress Tina&,#039,s Sissy Slut Maid Louise

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    Views: 33084 Added: 28 Mar 13
    Time: 04:39 Tube: XHamster
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  • French Lady fucked by two guys in Prison

    French Lady fucked by two guys in Prison
    Views: 614 Added: 10 Apr 13
    Time: 11:08 Tube: RedTube
    Tags: Anal, Cumshots, Double penetration

  • Bondage chair and toys held prisoner

    Bondage chair and toys held prisoner
    Views: 309 Added: 12 Jul 13
    Time: 03:49 Tube: XVideos
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  • Domina instructing her sissy servant

    Domina instructing her sissy servant
    Views: 312 Added: 4 Feb 13
    Time: 05:05 Tube: DrTuber
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    Views: 15514 Added: 20 Oct 13
    Time: 00:25 Tube: XHamster
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  • Die Sissy Tunte muss anschaffen.

    Die Sissy Tunte muss anschaffen.
    Views: 1611 Added: 8 Mar 13
    Time: 01:38 Tube: XHamster
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  • Sissy is getting fucked hard

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    Views: 8735 Added: 4 Feb 13
    Time: 20:49 Tube: DrTuber
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    Views: 3621 Added: 8 Mar 13
    Time: 02:33 Tube: XHamster
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    Views: 1983 Added: 28 Mar 13
    Time: 18:02 Tube: XHamster
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  • Three hot men in prison

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    Views: 1011 Added: 22 Feb 13
    Time: 27:46 Tube: XHamster
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  • prisoner of the cruel mistress

    prisoner of the cruel mistress
    Views: 2360 Added: 22 Feb 13
    Time: 46:07 Tube: XHamster
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  • Most prisons

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    Views: 4059 Added: 4 Mar 13
    Time: 05:43 Tube: H2Porn
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    Views: 3824 Added: 8 Mar 13
    Time: 08:08 Tube: XHamster
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    Views: 1756 Added: 22 Feb 13
    Time: 02:14 Tube: XHamster
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  • 10 Guys Fucking Sissy Slave Madysin (All Bareback)

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    Views: 3581 Added: 12 Jul 13
    Time: 17:58 Tube: XVideos
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    Views: 2159 Added: 20 Oct 13
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    Views: 1085 Added: 4 Mar 13
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    Views: 3285 Added: 20 Oct 13
    Time: 02:08 Tube: XHamster
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  • Worship his balls, sissy. PM vol. 25

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    Views: 366 Added: 22 Dec 12
    Time: 15:35 Tube: XHamster
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    Views: 4059 Added: 4 Mar 13
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  • Two chicks in puffy dresses feminizing a man

    Two chicks in puffy dresses feminizing a man
    Views: 4838 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
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  • prison life

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    Views: 5694 Added: 8 Mar 13
    Time: 35:45 Tube: XHamster
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    Views: 2310 Added: 20 Oct 13
    Time: 01:16 Tube: XHamster
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  • Most prisons

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    Views: 1556 Added: 4 Mar 13
    Time: 05:31 Tube: H2Porn
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  • My Sissy Bum Paddled in Panties with Pinky Lace Trim

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    Views: 1192 Added: 20 Oct 13
    Time: 05:55 Tube: XHamster
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    Views: 819 Added: 23 Dec 13
    Time: 01:09 Tube: XHamster
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    Views: 9491 Added: 14 Jan 13
    Time: 02:52 Tube: XHamster
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    Views: 432 Added: 10 Apr 13
    Time: 21:53 Tube: RedTube
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