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

70.8K views
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08:37
Black blow up spiked butt plug for my S&M Daddies!
Victoria Lecherri

18.7K 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

17.3K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

5.2K views
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10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
TheToxicTwins

29.2K views
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10:01
Working on Sissy Slave Denise Humain Nipples for hours Part 1
Denise Humain

42.8K 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

17.3K 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

27.5K views
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02:17
Boss tranny show him his painful role
XXL4XXL

25.8K views
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03:41
Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
Cyanide Mistress Of Darkness

7.2K views
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06:39
I am a naughty bitch that needs to be punished severely
Victoria Lecherri

2.6K views
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03:30
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HatanoMiwa

282.4K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

8.8K views
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03:26
Kill that sweet butthole with a Dildo
Charlotte Wilde

4.7K views
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23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain

4.4K views
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02:02
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
Denise Humain

3.1K views
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10:24
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 4 - 4
Denise Humain

3.4K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

7.3K views
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02:33
Hot Crossdresser fucks herself with a massive homemade toy!!
Dope Slut

1.1K 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

2K views
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08:03
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
Denise Humain

1.7K views
Not available in United States

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

2K views
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00:20
Sissy training Extreme CBT electric shock cock pain bdsm
iFetFuc

10.7K views
Not available in United States

00:26
FUCKING MY HOLE WITH A BOTTLE
Natasha Fox

1.2K views
Not available in United States

36:28
Pain Slut Kira
Twistedrama

34.4K views
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18:29
Just because I can..
Twistedrama

74.2K views
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10:53
The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
alinanightsky

4.7K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

96.4K views
Not available in United States

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

53K views
Not available in United States

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

34.4K views
Not available in United States

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

63.6K views
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09:59
How to torture a beautiful sissy cock
MyLolaTrav

18.2K views
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17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699

48.5K views
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04:56
Caning and choking Kitsy
Kitsy Meow

47.3K views
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08:01
Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
Linzy19

31.4K views
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02:46
Daddy domination over his sissy sex slave and to taught her that my place is under his balls
alinanightsky

2.3K views
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10:29
How a Tgirl severely punishs her big cock.
MyLolaTrav

19.5K views
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25:04
Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
Derek6699

7.9K views
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14:42
Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
Denise Humain

11.8K views
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00:43
Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
Allmylinks

27.2K views
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02:20
116 min degrading of bdsm sissy pain whore Alina
alinanightsky

6.8K views
Not available in United States

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

25.2K 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

9.2K views
Not available in United States

03:36
Step-sister pinkish Jim got long painful anal with squirting on her engagement in the morning time
xhtad1

20.2K views
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09:09
3 dildos, a crop, clothspins and a horny girl on a bed
Bambi Christa

8.4K views
Not available in United States

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

4.6K views
Not available in United States

10:55
Kylie's prediciment
K Kylie Lynn

9.5K views