Most Popular caning sissy Videos

  • On Your Toes Sissy Boy

    On Your Toes Sissy Boy
    Views: 0 Added: 4 Feb 13
    Time: 06:43 Tube: DrTuber
    Tags: Bizarre, Bondage, Caning

  • Spanking Caning - Jeans and Bare Bottom

    Spanking Caning - Jeans and Bare Bottom
    Views: 16963 Added: 14 Jan 13
    Time: 08:13 Tube: XHamster
    Tags: Bdsm, British, Caning

  • Jail caning Amelia Rutherford

    Jail caning Amelia Rutherford
    Views: 14699 Added: 10 Dec 18
    Time: 03:07 Tube: XHamster
    Tags: 18 year old, Caning, Jail

  • 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

  • Disciplined with the cane, sternly but not severely.

    Disciplined with the cane, sternly but not severely.
    Views: 298582 Added: 14 Jan 13
    Time: 02:34 Tube: XHamster
    Tags: Bdsm, British, Caning

  • Sissy Slut in Motel

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

  • Naughty schoolgirl is caned and spanked

    Naughty schoolgirl is caned and spanked
    Views: 21834 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Naughty, Pain

  • Girl in pantyhose caned

    Girl in pantyhose caned
    Views: 2289 Added: 22 Feb 13
    Time: 01:09 Tube: XHamster
    Tags: Caning, Pantyhose, Spanking

  • CANED FOR DISOBEDIENCE

    CANED FOR DISOBEDIENCE
    Views: 24048 Added: 20 Oct 13
    Time: 02:07 Tube: XHamster
    Tags: Bdsm, Caning, Hardcore

  • 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

  • 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

  • Bound girl's ass is caned hard

    Bound girl's ass is caned hard
    Views: 7631 Added: 7 May 13
    Time: 03:00 Tube: TubeWolf
    Tags: Ass, Bondage, Bound

  • Caning Sequence

    Caning Sequence
    Views: 11653 Added: 20 Oct 13
    Time: 02:13 Tube: XHamster
    Tags: Bdsm, Caning, Czech

  • 101 strokes of the cane

    101 strokes of the cane
    Views: 26456 Added: 12 Jul 13
    Time: 30:02 Tube: XVideos
    Tags: Bdsm, Caning, Femdom

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

  • pegging a sissy

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

  • BDSM Spanking Caning - 10 Strokes

    BDSM Spanking Caning - 10 Strokes
    Views: 30320 Added: 28 Mar 13
    Time: 01:55 Tube: XHamster
    Tags: Bdsm, Caning, Spanking

  • retro caning

    retro caning
    Views: 16508 Added: 23 Dec 13
    Time: 04:46 Tube: XHamster
    Tags: Bdsm, Caning, Femdom

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    tranny slut cyndee sucks off sissy faggot whore
    Views: 27447 Added: 22 Feb 13
    Time: 08:32 Tube: XHamster
    Tags: Ladyboy, Shemales, Sissy

  • A Sissy Made

    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

  • sissy bitch wendy jane fucks cyndee in the ass

    sissy bitch wendy jane fucks cyndee in the ass
    Views: 7548 Added: 20 Feb 13
    Time: 12:17 Tube: XHamster
    Tags: Ass, Bitch, Fucking

  • Caned & DPed for Being A Vixen I Want it That Way

    Caned & DPed for Being A Vixen I Want it That Way
    Views: 23244 Added: 20 Oct 13
    Time: 03:48 Tube: XHamster
    Tags: Amateur, Caning, Dped

  • sissy bitch wendy jane gets her little limp dicky sucked oe

    sissy bitch wendy jane gets her little limp dicky sucked oe
    Views: 14578 Added: 22 Feb 13
    Time: 03:31 Tube: XHamster
    Tags: Bitch, Ladyboy, Shemales

  • A Sissy Made Foot Milking

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

  • Dominatrix Annabelle gives the cane

    Dominatrix Annabelle gives the cane
    Views: 5888 Added: 8 Mar 13
    Time: 00:42 Tube: XHamster
    Tags: Bdsm, British, Caning

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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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    Naked blonde caning
    Views: 5708 Added: 20 Feb 13
    Time: 05:20 Tube: XHamster
    Tags: Bdsm, Blondes, Caning

  • Caned balls

    Caned balls
    Views: 8838 Added: 28 Mar 13
    Time: 01:21 Tube: XHamster
    Tags: Caning

  • White Chiffon Sissy Blouse

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

  • Naughty nurse caning

    Naughty nurse caning
    Views: 7832 Added: 28 Mar 13
    Time: 07:19 Tube: XHamster
    Tags: Bdsm, Caning, Naughty

  • 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

  • She has needles in her body and he's caning her

    She has needles in her body and he's caning her
    Views: 201 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Bondage, Caning, Pain

  • Masked Sissy Sucker

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

  • Tied up gay caned and fucked in hairdresser shop

    Tied up gay caned and fucked in hairdresser shop
    Views: 1278 Added: 21 Jan 13
    Time: 01:46 Tube: DrTuber
    Tags: Bdsm, Bondage, Bound

  • SoloInterviews Sasha Cane small tits brunette

    SoloInterviews Sasha Cane small tits brunette
    Views: 9441 Added: 10 Apr 13
    Time: 03:04 Tube: RedTube
    Tags: Brunettes, Caning, Masturbating

  • Sissy Slut

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

  • Prison Caning and Birching

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

  • British Slut Sasha Cane JOI

    British Slut Sasha Cane JOI
    Views: 12256 Added: 28 Mar 13
    Time: 09:05 Tube: XHamster
    Tags: British, Brunettes, Caning

  • 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

  • Hot chick in a skirt is caned badly

    Hot chick in a skirt is caned badly
    Views: 6827 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Chick, Pain

  • The girl is caned and it leaves terrible marks

    The girl is caned and it leaves terrible marks
    Views: 15905 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Pain

  • Watch a rough and painful caning

    Watch a rough and painful caning
    Views: 10045 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Pain, Rough

  • Brutal Caning

    Brutal Caning
    Views: 478 Added: 14 Jan 13
    Time: 07:56 Tube: XHamster
    Tags: Brutal, Caning, Femdom

  • Extreme caning by masochistic female

    Extreme caning by masochistic female
    Views: 14699 Added: 14 Nov 18
    Time: 01:59 Tube: XHamster
    Tags: Caning, Extreme, Romanian

  • 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

  • Russian guy with sissy crossdresser

    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

  • Double caning

    Double caning
    Views: 678 Added: 20 Feb 13
    Time: 04:59 Tube: XHamster
    Tags: Bdsm, Caning, Double penetration

  • Randy Miss A. got a caning

    Randy Miss A. got a caning
    Views: 9206 Added: 2 Dec 18
    Time: 02:12 Tube: XHamster
    Tags: Bdsm, Caning, Spanking

  • Mental Poison - Sissy Compilation

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

  • Freaks of Nature 137 Scinny Young woman and the Cane

    Freaks of Nature 137 Scinny Young woman and the Cane
    Views: 11653 Added: 8 Mar 13
    Time: 09:29 Tube: XHamster
    Tags: Bdsm, Caning, Nature

  • Super naughty blonde fucked and spanked

    Super naughty blonde fucked and spanked
    Views: 301 Added: 4 Feb 13
    Time: 05:20 Tube: DrTuber
    Tags: Blondes, Caning, Fetish

  • Caned for lateness

    Caned for lateness
    Views: 1081 Added: 22 Feb 13
    Time: 10:42 Tube: XHamster
    Tags: Bdsm, Caning, Femdom

  • Sissy Gives Head

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

  • EP2

    EP2
    Views: 9285 Added: 4 Feb 13
    Time: 11:00 Tube: DrTuber
    Tags: Bdsm, Blondes, Brunettes

  • sissy slave

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

  • Domina pegging worthless sissy

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

  • Chastity Mistress Femdom Humiliation cb6000 Slave Sissy fellow

    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

  • whipped caned and sucked...gfawkes

    whipped caned and sucked...gfawkes
    Views: 13493 Added: 28 Mar 13
    Time: 00:48 Tube: XHamster
    Tags: Bdsm, Caning, Spanking

  • Sissy Daddys stable

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

  • She's bent over, tied down and caned hard

    She's bent over, tied down and caned hard
    Views: 16307 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Bondage, Caning, Pain

  • Awesome Caning 2

    Awesome Caning 2
    Views: 7430 Added: 8 Mar 13
    Time: 07:13 Tube: XHamster
    Tags: Awesome, Bdsm, Caning

  • 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

  • sent for a caning

    sent for a caning
    Views: 7028 Added: 23 Dec 13
    Time: 28:10 Tube: XHamster
    Tags: Bdsm, Caning, Spanking

  • 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

  • Breast caning and cruel bullwhipping with Lola.

    Breast caning and cruel bullwhipping with Lola.
    Views: 16508 Added: 28 Mar 13
    Time: 00:52 Tube: XHamster
    Tags: Bdsm, Breast, Caning

  • The girl pulls down her pants and gets a caning

    The girl pulls down her pants and gets a caning
    Views: 6511 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Pain, Panties

  • mistress uses her slave and a cane

    mistress uses her slave and a cane
    Views: 11854 Added: 23 Dec 13
    Time: 30:03 Tube: XHamster
    Tags: Caning, Femdom, Mistress

  • 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

  • Tied Caned And Clamped

    Tied Caned And Clamped
    Views: 201 Added: 8 Mar 13
    Time: 12:05 Tube: XHamster
    Tags: Bdsm, Caning, Clamp

  • 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

  • Chick is spanked hard and caned hard

    Chick is spanked hard and caned hard
    Views: 201 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Caning, Chick, Pain

  • Passionated giving blowjob sissy

    Passionated giving blowjob sissy
    Views: 201 Added: 20 Oct 13
    Time: 01:44 Tube: XHamster
    Tags: Amateur, Blowjob, Dick

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    training sissy to suck dick sph joi
    Views: 201 Added: 2 Dec 18
    Time: 15:01 Tube: XHamster
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  • 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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    Views: 201 Added: 14 Jan 13
    Time: 09:00 Tube: XHamster
    Tags: Cuckold, Cumshots, Femdom

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    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

  • Sissy fun

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

  • Touching toes caning

    Touching toes caning
    Views: 7229 Added: 8 Mar 13
    Time: 05:53 Tube: XHamster
    Tags: Bdsm, Caning, Spanking

  • Cum Sissy

    Cum Sissy
    Views: 2417 Added: 20 Oct 13
    Time: 00:36 Tube: XHamster
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  • Babe caned and humiliated

    Babe caned and humiliated
    Views: 679 Added: 15 Feb 13
    Time: 05:29 Tube: H2Porn
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    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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    Girls trying something new spanking
    Views: 2088 Added: 21 Jan 13
    Time: 03:20 Tube: DrTuber
    Tags: Ass, Brunettes, Caning

  • The schoolgirl gets caned and it hurts

    The schoolgirl gets caned and it hurts
    Views: 8234 Added: 7 May 13
    Time: 03:01 Tube: TubeWolf
    Tags: Bondage, Caning, Pain

  • Her ass is beaten hard with a miniature cane

    Her ass is beaten hard with a miniature cane
    Views: 11452 Added: 7 May 13
    Time: 03:00 Tube: TubeWolf
    Tags: Ass, Caning, Femdom

  • MY Alluring SISSY Cunt

    MY Alluring SISSY Cunt
    Views: 1777 Added: 20 Oct 13
    Time: 02:20 Tube: XHamster
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    new sissy stockings!!!
    Views: 2819 Added: 22 Feb 13
    Time: 13:31 Tube: XHamster
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  • Vacuum machine, cane and electrified gun

    Vacuum machine, cane and electrified gun
    Views: 7229 Added: 10 Dec 18
    Time: 06:37 Tube: XHamster
    Tags: Amateur, Bdsm, Caning

  • POV sissy cocksucker humiliation

    POV sissy cocksucker humiliation
    Views: 1812 Added: 8 Mar 13
    Time: 11:39 Tube: XHamster
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  • Caning &, Dildo

    Caning &, Dildo
    Views: 1081 Added: 22 Feb 13
    Time: 07:15 Tube: XHamster
    Tags: Bdsm, Caning, Dildo

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    how to give a sissy BJ
    Views: 811 Added: 20 Oct 13
    Time: 05:05 Tube: XHamster
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  • sissy maid gets own hole cleaned out after work - fisting

    sissy maid gets own hole cleaned out after work - fisting
    Views: 543 Added: 20 Oct 13
    Time: 01:34 Tube: XHamster
    Tags: Amateur, Bdsm, Cleaner

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    Cruel femdom wife spanking hubbys ass hard
    Views: 14156 Added: 12 Jul 13
    Time: 00:43 Tube: XVideos
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    POV sissy humiliation training
    Views: 3558 Added: 8 Mar 13
    Time: 04:53 Tube: XHamster
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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
    Tags: Bdsm, Bisexual, Cuckold

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    Seductive japanese Light Caning
    Views: 9843 Added: 10 Dec 18
    Time: 15:15 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
    Views: 5432 Added: 8 Mar 13
    Time: 03:42 Tube: XHamster
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    Views: 595 Added: 20 Oct 13
    Time: 05:43 Tube: XHamster
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  • Naughty teen gets punished

    Naughty teen gets punished
    Views: 301 Added: 21 Jan 13
    Time: 06:19 Tube: DrTuber
    Tags: Caning, Fetish, Hardcore

  • 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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    Mistress Cleo canes
    Views: 14556 Added: 8 Mar 13
    Time: 03:42 Tube: XHamster
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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
    Tags: Bdsm, Bondage, Domination

  • Ass Punished Sexy Brunette

    Ass Punished Sexy Brunette
    Views: 4099 Added: 4 Feb 13
    Time: 06:31 Tube: DrTuber
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    BIG Ebony MONSTER rubber toy destroying a WHITE SISSY Butt
    Views: 15514 Added: 20 Oct 13
    Time: 00:25 Tube: XHamster
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  • Blonde throat fucked and caned

    Blonde throat fucked and caned
    Views: 7028 Added: 10 Apr 13
    Time: 01:47 Tube: RedTube
    Tags: Blondes, Caning, Fucking

  • 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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    Candy Cane Shaped Dildo Penetration HD
    Views: 679 Added: 15 Feb 13
    Time: 06:58 Tube: H2Porn
    Tags: Amateur, Babes, Caning

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    Cuckold sissy banged with huge red strap on dick
    Views: 3824 Added: 8 Mar 13
    Time: 08:08 Tube: XHamster
    Tags: Amateur, Banging, Cuckold
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