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07:53
Sissy Maids Punishment
Derek6699

15.4K views
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14:55
Sissy Maid - Pain & Pleasure Bondage
Derek6699

8.8K views
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01:17
Daddy Loving Sissy Pain Slut Whipping
JessicaLynn15

4.4K views
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06:08
Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro
MyLolaTrav

2.4K views
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05:11
Masochistic tranny whips himself with flogger
Keeno666

1.2K views
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05:41
Sadistic vampire Mistress
Jazebel

1.8K views
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36:28
Pain Slut Kira
Twistedrama

34K views
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18:29
Just because I can..
Twistedrama

73.8K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

96K views
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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

70.6K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

52.7K views
Not available in United States

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

1.6K 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

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

18.6K 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

63.3K 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

48.4K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

47.1K views
Not available in United States

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

17.2K views
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08:01
Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
Linzy19

31.1K views
Not available in United States

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

5.2K views
Not available in United States

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

29.1K views
Not available in United States

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

19.5K views
Not available in United States

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

7.8K views
Not available in United States

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

1.3K views
Not available in United States

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

42.7K views
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14:42
Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
Denise Humain

11.6K 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

17.1K views
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00:43
Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
Allmylinks

27.1K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

25.2K views
Not available in United States

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

5.9K views
Not available in United States

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

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

27.3K 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
Not available in United States

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

8.3K 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
Not available in United States

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

3.5K views
Not available in United States

02:05
Compilation with Weekly Episodes from the pain whore Alina
alinanightsky

7.4K views
Not available in United States

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

15.4K views
Not available in United States

17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.1K views
Not available in United States

02:17
Boss tranny show him his painful role
XXL4XXL

25.8K views
Not available in United States

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

15K views
Not available in United States

04:04
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HatanoMiwa

57.3K views
Not available in United States

04:34
painful anal stretching and outdoor cumshot
Chantal Fouet

3.3K views
Not available in United States

08:09
Urethral sounding and vibration of a caged and bound shemale
MyLolaTrav

15.8K views
Not available in United States

04:08
dumb slut gets the belt for cumming without permission
Bambi Christa

6.5K views