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

73.6K views
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07:10
Redhead Asian shemale all covered in pain gets fucked
Extreme Ladyboys

40.4K 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

8.7K views
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02:20
116 min degrading of bdsm sissy pain whore Alina
alinanightsky

15K 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

65.1K views
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17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699

49.3K views
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11:32
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Sissy Cindy Slut

5.7K views
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01:57
Painful nice big cock

63.2K views
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02:05
Compilation with Weekly Episodes from the pain whore Alina
alinanightsky

12.1K 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

4.8K views
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10:55
Kylie's prediciment
K Kylie Lynn

9.7K views
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10:28
Teen Gets Her 1st Painful Screaming Anal But Let Her Finish

51.9K views
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05:55
Ass-to-Mouth Painful Sissy Bareback Fuck in Motel

29.3K views
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01:34
A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
alinanightsky

6.3K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

8.9K views
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17:02
Thick Anal Viring Gets Her 1st Time Very PAinful & Begging

42.2K views
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05:00
Sweet Anal Pain for Solo Sissy CD
Regina Blasegern

8.9K views
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01:04
Up Close Painful Femboy Dildo Practice
Khatara Shikiku

2.6K views
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14:21
Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
Denise Humain

4.4K views
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10:18
Little sluts bills punishment
Lizz_ss25

4K views
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06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku

4.3K views
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03:41
The Pressure of Pain and Punishment
BadGod

2.9K views
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01:28
First try for new plug and a bit bigger
Sanne

4.5K 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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17:28
Denise Humain Scene Mix (Anal, Nipple, Blowjob)
Denise Humain

1.8K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

7.4K views
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00:40
Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
Soloregin

2.2K views
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00:22
Pressing a giant plug out of my anus
Charlotte Wilde

2.7K views
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00:26
FUCKING MY HOLE WITH A BOTTLE
Natasha Fox

1.2K views
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01:14
pain turns me on
boobyb0y

75K views
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04:56
Caning and choking Kitsy
Kitsy Meow

48K views
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14:42
Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
Denise Humain

12.8K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

25.6K 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

9.7K views
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17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.4K views
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02:06
Sissy Nipple Cow Chastity Nipple Pump Electro Pain
Titten-Sau

15.4K views
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07:05
Candle Wax & Chastity Go Together like PB & Jelly
MJ

2.8K views
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14:55
Sissy Maid - Pain & Pleasure Bondage
Derek6699

9K views
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10:00
Girl loves pain and cum

12.8K views
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01:18
Sissy slut in pain
SissyPropertyUk

8.4K views
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01:23
Labor Pains

18.4K views
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04:15
Hot Wax On Sissy Cock
SubmissiveFetish

2.9K views
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06:12
Ladyboy Lisa 3 Pain And Pleasure
Ladyboy Gold

21.7K views
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00:59
Pain and Joy 2
Pai-chan

1.3K views
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00:46
Artist. Nithes (hard and Painful Sex, Big Thick and Milky Cock with Rich Testicles)
StrightAss

1.2K views
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17:10
Deepthroat Blowjob Training and Wax on Tits and Nipples
Denise Humain

4.3K 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

2.1K views