711 Results

Painful Punishment Porn Videos

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

99.9K views
Not available in United States

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

75.3K views
Not available in United States

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

55.3K 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

14.3K views
Not available in United States

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

35.4K views
Not available in United States

09:59
How to torture a beautiful sissy cock
MyLolaTrav

19K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

48.3K views
Not available in United States

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

20.3K views
Not available in United States

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

13.1K 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

18K views
Not available in United States

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

25.7K 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

9.8K views
Not available in United States

17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.5K views
Not available in United States

10:07
Domination and pain with this 2 shemales hardcore punishment
Latina Tranny

27.2K views
Not available in United States

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

2.8K 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

7.6K views
Not available in United States

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

6.8K views
Not available in United States

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

1.1K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

16K views
Not available in United States

02:50
Tabasco Dildo Punishment for forgetting my butt plug today...
Sissy-Hinata

1.6K views
Not available in United States

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

3.1K views
Not available in United States

18:03
A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
MyLolaTrav

3.8K views
Not available in United States

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

2.7K views
Not available in United States

10:49
Rebecca's painful Orgasm
R Rebeccafuxx

6K views
Not available in United States

07:02
Mistress Cy IPL Hair Removal Punishment
Cyanide Mistress Of Darkness

9.9K views
Not available in United States

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

4.5K views
Not available in United States

06:02
Shemale cock and nipples pain...
MyLolaTrav

2.6K views
Not available in United States

10:18
Little sluts bills punishment
Lizz_ss25

4K views
Not available in United States

30:01
(P.4-5) Athena 50 Shades of FUCKED UP TATTOO BDSM XXX 666
Cyanide Mistress Of Darkness

6.7K views
Not available in United States

05:57
DRIPPING HOT WAX ON MY COCK
Kenzie Star

3.7K views
Not available in United States

06:35
BambiChrista gets punished for making demands of her Master. She has to hit clothspins off her butt and thighs
Bambi Christa

3.3K views
Not available in United States

06:27
Maso Muslima squirts in Pain
R Rebeccafuxx

11.7K views
Not available in United States

05:11
Masochistic tranny whips himself with flogger
Keeno666

1.3K views
Not available in United States

01:14
Tyche_Toxic Winces In Pain During Self CBT
Tyche Toxic

3.9K views
Not available in United States

04:15
Hot Wax On Sissy Cock
SubmissiveFetish

2.9K views
Not available in United States

03:41
The Pressure of Pain and Punishment
BadGod

3K views
Not available in United States

05:12
FtM punished fir being lazy
BonusholeToy

891 views
Not available in United States

03:02
Fat Sissy light ball torture and wax play in chastity
Chubby Sissy Dani

2.9K views
Not available in United States

02:59
Sissy tortured with wax
Sissy_Nadiene

329 views
Not available in United States

05:10
FtM boy punished for being lazy
BonusholeToy

2.3K views
Not available in United States

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

2.4K views
Not available in United States

09:19
Painful nipple torture chains

1.2K views
Not available in United States

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

4.9K views
Not available in United States

00:07
Cock Punishment
SubmissiveFetish

1.3K views
Not available in United States

01:15:03
Pain and Pleasure Part 2

193.6K views
Not available in United States

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

260.9K views
Not available in United States

14:58
Pain Is Her Pleasure
Kink

915.1K views