31.4K Results

Crossdresser Punishment Porn Videos

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09:02
Crossdresser Punishment Milking

211.7K views
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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

206.9K views
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05:43
Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
alinanightsky

146.1K views
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07:12
Mia was betrayed by her friend and husband. Eliel loves Mia but doesn't miss an opportunity to be sucked by a
Mirella Diniz

24.8K views
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23:50
Doc punishing his bratty submissive femboy sissy Michele
Sissy Michelle MTF

113K views
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02:37
BDSM Sissy Slut get punish and hits
alinanightsky

30.6K views
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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

99.3K views

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

173.4K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

117.4K views
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00:38
Sucker for Punishment
Jennifer Lunden

38.6K views
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11:33
Hard punishment and sex. KitsyMe0w
Kitsy Meow

95.1K views
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12:23
Sissy slut non stop edging as punishment
CindySissy

42.5K views
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15:10
Maintenance spanking for Kitsy. Blowjob and sex following the punishment.
Kitsy Meow

127.6K views
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07:45
Trans Lesbian Anal Fisting And Cum in Own Mouth - Jessica Bloom And Jenby Doll
Jessica Bloom

47.7K 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

8.7K views
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01:16
Tranny dom punishes the perverted panty sniffer! Now he's her bitch!
TV_Helena

6.9K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

66.7K 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

19.8K views
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08:18
Valentine's Day 1
KatyKoroleva

38.6K views
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04:56
Caning and choking Kitsy
Kitsy Meow

54.5K views
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11:46
Nady catches me caressing myself and to punish me smashes my pussy and cums on my little panties
Nady-So

51.2K views
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36:35
Sissy Maid Self Bondage Electro Punishment
Derek6699

56.8K views
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06:53
More maintenance spanking for Kitsy. OTK punishment.
Kitsy Meow

8.4K views
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07:50
Transgirl lactation, young sissy milks her hormonate tits, teen shemale torture her nipples and slaps them.
fermerino

35.9K views
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04:47
Sunday punishment by Master
PA8mmMaster

23.6K views
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14:51
BDSM Transgirl Lactation Rough Punishment Homonate Puffy Boobs Shemale
fermerino

40K views
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21:51
British MILF Lisa spanks sissy Charlotte
Lisa Essex

26.9K views
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11:12
Roommate Feminized and Fucked for Punishment
Bailey Wilde

38.6K views
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42:01
Watch torment of a Asian shemale
Alfacontent World

44.3K views
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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

25.2K views
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09:04
Two naughty blonde trans schoolgirls are punished by Sir Rob
Mrs Samantha

3.7K views
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05:21
Nasty Viper🤍Being too sexy can be wrong, and bad Nikke deserves punishment!
Nasty Azu

5.7K views
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12:44
Sissy balls torture ballbusting
cdvaleria1996

3.4K views
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14:53
Blonde and naughty schoolgirls Daphne and Samantha give Sir Rob a good Blowjob!
Mrs Samantha

2.3K views
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14:24
Spanking naughty Schoolgirl Daphne, close-up shots while chained to the bed and receiving some spanking as punishment
Mrs Samantha

2.6K views
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04:16
Sissy Crossdresser maid gets punished by BigDaddy8inchz -Onlyfans
BBC_4Sissy

13.1K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

28.5K views
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03:12
sissy sarah nipple tits torture
Sissy_sarah69

12.2K views
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07:53
Sissy Maids Punishment
Derek6699

18.4K views
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33:24
Sissys Wooden Pony Ballet Boot Torment
Derek6699

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

4.2K views
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10:57
Getting caught sunbathing when I should be working.
DonnaCDUK

10.6K views
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06:19
Kitsy gets Maintenance spanking. Adorable socks and feet.
Kitsy Meow

6.1K views
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28:23
A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
Denise Humain

4K views
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10:57
BDSM Pretty Sissy boy Punished, Spanked Balls and Ass, Shemale Whipped so Hard on Webcam
fermerino

7.9K views
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24:42
Sissy Maid CBT Self Bondage Torture
Derek6699

13.4K views
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05:51
Ozriel Whipping Cock and Shaking Ass
Oznob Oznofla

13K views