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Painful Spanking Porn Videos

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36:28
Pain Slut Kira
Twistedrama

14.2K views
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18:29
Just because I can..
Twistedrama

56.8K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

79K views
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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

49K views
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04:56
Caning and choking Kitsy
Kitsy Meow

42.3K views
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06:36
Morning Procedures - bathing in sheer lingerie and painful anal stretching
Chantal Fouet

3K views
Not available in United States

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

6.1K views
Not available in United States

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

2.2K views
Not available in United States

05:37
Pink psycho bath bondage
Jazebel

1.3K views
Not available in United States

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

3.9K views
Not available in United States

05:41
Sadistic vampire Mistress
Jazebel

1.1K views
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02:49
sissy slut punishing herself with a paddle
Emma Huntcock

2.1K views
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03:43
Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
Sissy Sandy

4.5K views
Not available in United States

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

42.2K views
Not available in United States

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

29.8K 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

55.1K views
Not available in United States

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

13.8K views
Not available in United States

09:59
How to torture a beautiful sissy cock
MyLolaTrav

15.6K views
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17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699

43K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

4.3K 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

15.1K views
Not available in United States

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

15.8K views
Not available in United States

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

4.9K views
Not available in United States

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

26.6K views
Not available in United States

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

22.4K views
Not available in United States

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

37.1K views
Not available in United States

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

13.4K views
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08:01
Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
Linzy19

15.7K 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

6K views
Not available in United States

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

23K 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
Bihar

18.5K 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

20.3K 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

3.5K 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

14K views
Not available in United States

17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

14.6K views
Not available in United States

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

7.8K views
Not available in United States

02:17
Boss tranny show him his painful role
XXL4XXL

21.4K views
Not available in United States

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

13.1K views
Not available in United States

04:04
Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass
HatanoMiwa

54.1K views
Not available in United States

02:46
Becca squirts in shiny pantyhose
Rebeccafuxx

2.5K views
Not available in United States

04:34
painful anal stretching and outdoor cumshot
Chantal Fouet

2.9K views
Not available in United States

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

4.9K views
Not available in United States

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

14.8K views
Not available in United States

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

6.6K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

12.9K views
Not available in United States

07:03
Maso Bitch Rebecca
Rebeccafuxx

2.1K views
Not available in United States

22:12
Rebeccas Maso Perversions
Rebeccafuxx

8.4K views