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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

53.7K views
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08:37
Black blow up spiked butt plug for my S&M Daddies!
Victoria Lecherri

14.6K views
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01:29:00
Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
Cyanide Mistress Of Darkness

15.5K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

4.5K views
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10:01
Working on Sissy Slave Denise Humain Nipples for hours Part 1
Denise Humain

38.1K views
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14:26
Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
Denise Humain

14.2K views
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06:08
Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
Candy Ass Sissy

21.8K views
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02:17
Boss tranny show him his painful role
XXL4XXL

22.1K views
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03:41
Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
Cyanide Mistress Of Darkness

6.7K views
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22:12
Rebeccas Maso Perversions
R Rebeccafuxx

8.5K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

8.2K views
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03:30
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274.3K views
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03:26
Kill that sweet butthole with a Dildo
Charlotte Wilde

3.8K views
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06:39
I am a naughty bitch that needs to be punished severely
Victoria Lecherri

2.2K views
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23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain

4K views
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02:02
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
Denise Humain

2.9K views
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10:24
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 4 - 4
Denise Humain

3.2K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

6.5K views
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02:33
Hot Crossdresser fucks herself with a massive homemade toy!!
Dope Slut

973 views
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00:29
Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
iFetFuc

1.6K views
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08:03
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
Denise Humain

1.6K views
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05:24
MissRose TS - Rosanna IN pRIVATE - WILD SHEMALE pAinal MASTURBATION - Rough ASSPLAY Big SHECOCK - cumshot
MissRose TS

1.5K views
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00:26
FUCKING MY HOLE WITH A BOTTLE
Natasha Fox

1.1K views
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36:28
Pain Slut Kira
Twistedrama

19K views
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18:29
Just because I can..
Twistedrama

60.1K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

82.2K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

44.4K views
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11:41
How to Give Pain and Pleasure to a Big Sissy Cock
MyLolaTrav

30.8K views
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06:06
My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
Nathalia Fontes

56.2K views
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09:59
How to torture a beautiful sissy cock
MyLolaTrav

16.1K views
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17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699

44.2K views
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04:56
Caning and choking Kitsy
Kitsy Meow

43.5K views
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10:29
How a Tgirl severely punishs her big cock.
MyLolaTrav

16.5K views
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10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
TheToxicTwins

27.1K views
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25:04
Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
Derek6699

5.5K views
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00:43
Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
Allmylinks

23.3K views
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08:01
Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
Linzy19

18K views
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13:59
Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
Denise Humain

6.6K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

23.4K views
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03:36
Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
Bihar

18.8K views
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29:58
Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
LaRicura16

3.7K views
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06:36
Morning Procedures - bathing in sheer lingerie and painful anal stretching
Chantal Fouet

3.1K views
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10:12
Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose

14.3K views
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14:42
Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
Denise Humain

8.5K views
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17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

14.9K views
Not available in United States

02:06
Sissy Nipple Cow Chastity Nipple Pump Electro Pain
Titten-Sau

13.5K views
Not available in United States

04:04
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54.7K views