27.3K Results

Crossdresser Torture Porn Videos

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05:03
Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
alinanightsky

195.9K views
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05:43
Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
alinanightsky

141.6K views
Not available in United States

02:37
BDSM Sissy Slut get punish and hits
alinanightsky

28.7K views
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23:50
Doc punishing his bratty submissive femboy sissy Michele
Sissy Michelle MTF

111.6K views
Not available in United States

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

96.8K views
Not available in United States

04:44
No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
Derek6699

172.2K views
Not available in United States

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

115.3K views

Not available in United States

00:38
Sucker for Punishment
Jennifer Lunden

36.4K views
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11:33
Hard punishment and sex. KitsyMe0w
Kitsy Meow

93.8K views
Not available in United States

15:10
Maintenance spanking for Kitsy. Blowjob and sex following the punishment.
Kitsy Meow

125.9K views
Not available in United States

12:23
Sissy slut non stop edging as punishment
CindySissy

40.9K views
Not available in United States

07:45
Trans Lesbian Anal Fisting And Cum in Own Mouth - Jessica Bloom And Jenby Doll
Jessica Bloom

46.4K views
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11:38
Blonde trans schoolgirl Daphne is being punished by head mistress Mrs Samantha for playing around with the boys
Mrs Samantha

7.9K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

65.7K views
Not available in United States

01:16
Tranny dom punishes the perverted panty sniffer! Now he's her bitch!
TV_Helena

5.9K 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

19.1K views
Not available in United States

08:18
Valentine's Day 1
KatyKoroleva

37.8K views
Not available in United States

36:35
Sissy Maid Self Bondage Electro Punishment
Derek6699

55.8K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

53.9K views
Not available in United States

11:46
Nady catches me caressing myself and to punish me smashes my pussy and cums on my little panties
Nady-So

50.8K views
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07:50
Transgirl lactation, young sissy milks her hormonate tits, teen shemale torture her nipples and slaps them.
fermerino

35.3K views
Not available in United States

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

7.8K views
Not available in United States

14:51
BDSM Transgirl Lactation Rough Punishment Homonate Puffy Boobs Shemale
fermerino

39.3K views
Not available in United States

21:51
British MILF Lisa spanks sissy Charlotte
Lisa Essex

26.5K views
Not available in United States

11:12
Roommate Feminized and Fucked for Punishment
Bailey Wilde

38K views
Not available in United States

04:47
Sunday punishment by Master
PA8mmMaster

23.2K views
Not available in United States

05:21
Nasty Viper🤍Being too sexy can be wrong, and bad Nikke deserves punishment!
Nasty Azu

5K views
Not available in United States

09:04
Two naughty blonde trans schoolgirls are punished by Sir Rob
Mrs Samantha

3.2K views
Not available in United States

14:24
Spanking naughty Schoolgirl Daphne, close-up shots while chained to the bed and receiving some spanking as punishment
Mrs Samantha

2.4K views
Not available in United States

06:07
Huge dildo is pushed deeper into the ass by rubber bands. BDSM TS self bondage torture. Huge Tits Cup-Z Anal Fuck Extreme deep
Endless Deeply

24.2K views
Not available in United States

12:44
Sissy balls torture ballbusting
cdvaleria1996

2.8K views
Not available in United States

12:27
Naughty schoolgirl Daphne, receiving punishment and rewards from head mistress Samantha!
Mrs Samantha

4K views
Not available in United States

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

28.3K views
Not available in United States

04:16
Sissy Crossdresser maid gets punished by BigDaddy8inchz -Onlyfans
BBC_4Sissy

12.8K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

18.2K views
Not available in United States

14:53
Blonde and naughty schoolgirls Daphne and Samantha give Sir Rob a good Blowjob!
Mrs Samantha

1.5K views
Not available in United States

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

3.7K views
Not available in United States

33:24
Sissys Wooden Pony Ballet Boot Torment
Derek6699

11.8K views
Not available in United States

05:51
Ozriel Whipping Cock and Shaking Ass
Oznob Oznofla

12.8K views
Not available in United States

18:52
Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.
Kitsy Meow

14.1K views
Not available in United States

24:42
Sissy Maid CBT Self Bondage Torture
Derek6699

13.2K views
Not available in United States

10:57
BDSM Pretty Sissy boy Punished, Spanked Balls and Ass, Shemale Whipped so Hard on Webcam
fermerino

7.8K views
Not available in United States

05:08
Kelli gagged with a pee covered penis gag
Kelli UK

8.1K views
Not available in United States

06:19
Kitsy gets Maintenance spanking. Adorable socks and feet.
Kitsy Meow

5.8K views
Not available in United States

04:03
Gagged and bound getting torture with candle wax
CindySissy

8.8K views
Not available in United States

12:24
New ElisyaHijabDoll 2024 extreme masturbation Fuck fast with dildo with a hot candle
HijabRubberSexDoll

9.1K views
Not available in United States

11:43
Kitsy gets hand spanked OTK.
Kitsy Meow

8.8K views