186 Results

Pain Porn Videos

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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

71.8K views
Not available in United States

01:48
1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR

569.5K views
Not available in United States

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

34K views
Not available in United States

14:58
Pain Is Her Pleasure
Kink

926.1K views
Not available in United States

01:14
pain turns me on
boobyb0y

83.4K views
Not available in United States

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

23.9K views
Not available in United States

01:15:03
Pain and Pleasure Part 2

201.2K views
Not available in United States

01:15:02
Pain and pleasure, chastity and lust, Part 2

268.3K views
Not available in United States

03:30
Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
HatanoMiwa

291.4K views
Not available in United States

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

105.8K 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

31.7K views
Not available in United States

36:28
Pain Slut Kira
Twistedrama

44.1K views
Not available in United States

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

12.9K views
Not available in United States

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

36.5K views
Not available in United States

02:37
DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM

161.6K views
Not available in United States

13:35
Lisa Femelle - The Whore of Master pain-

43.5K views
Not available in United States

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

59K 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

60.4K views
Not available in United States

02:17
Boss tranny show him his painful role
XXL4XXL

29.6K views
Not available in United States

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

22.3K views
Not available in United States

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

30.7K views
Not available in United States

01:33
fucking my femboy slave sissy slut painful anal

111.7K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

50.4K views
Not available in United States

03:04
25 min of abuse and hard use for the pain whore Alina
alinanightsky

3K views
Not available in United States

18:18
Anal fist fuck faggot love to feel the pain in the ass
Nicole Montero

112.4K views
Not available in United States

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

54.1K views
Not available in United States

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

42.7K views
Not available in United States

06:53
More maintenance spanking for Kitsy. OTK punishment.
Kitsy Meow

4.6K 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

69.3K views
Not available in United States

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

51.3K views
Not available in United States

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

22K views
Not available in United States

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

45.4K views
Not available in United States

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

14.4K views
Not available in United States

03:14
Pleasure Pain Sissy

37.6K views
Not available in United States

09:59
How to torture a beautiful sissy cock
MyLolaTrav

20.1K views
Not available in United States

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

36.6K views
Not available in United States

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

26.5K views
Not available in United States

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

16.3K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

16.8K 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

19.5K views
Not available in United States

51:35
Pain and pleasure, chastity and lust, Part 1

106.2K views
Not available in United States

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

43.3K views
Not available in United States

28:23
A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
Denise Humain

2.1K views
Not available in United States

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

5.4K views
Not available in United States

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

30.5K views
Not available in United States

11:32
Sissy faggot bitch
Sissy Cindy Slut

6.4K views
Not available in United States

04:02
Finishing up with pain on my balls
Naomi Perv

2.9K views