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Crossdressed Punished Porn Videos

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Did you mean crossdresser punished?

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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

71K views
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03:35
Crossdresser with Huge Tits Cup Z in Fishnet Suit - Let my Sexy Big Boobs Swing and Show my Huge Dildos for Anal Torture
Endless Deeply

34.7K views
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08:42
Trans girl punishes this guy by destroying his ass
Marika Ferreira

176.1K views
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07:45
Trans Lesbian Anal Fisting And Cum in Own Mouth - Jessica Bloom And Jenby Doll
Jessica Bloom

31.4K views
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11:27
New Task-cock torture with toothpaste
Loreleyadd

21.4K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

97.1K views
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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

71.8K views
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36:35
Sissy Maid Self Bondage Electro Punishment
Derek6699

46.2K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

53.4K views
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15:10
Maintenance spanking for Kitsy. Blowjob and sex following the punishment.
Kitsy Meow

109.7K views
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11:33
Hard punishment and sex. KitsyMe0w
Kitsy Meow

81.2K views
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04:44
No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
Derek6699

149.7K views
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05:43
Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
alinanightsky

63.6K views
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11:12
Roommate Feminized and Fucked for Punishment
Bailey Wilde

31.6K 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

45.3K views
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04:47
Sunday punishment by Master
PA8mmMaster

18K views
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06:37
First tortured with electric shocks, then cummed in stockings
Loreleyadd

4.5K views
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04:56
Caning and choking Kitsy
Kitsy Meow

47.5K views
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08:18
Valentine's Day 1
KatyKoroleva

26.9K views
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05:18
New task - cock torture with toothpaste in pantyhose 3
Loreleyadd

19.1K views
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19:26
POV You are caught using and stealing the owner's dildo - XXL dildo anal - Sissification
Elvi Lynx

18.1K views
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06:18
Punishment For A Naughty School Gurl
Chantal Fouet

8.2K views
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15:12
Sissy Maids Spiked Chastity Cage Self Bondage Torment
Derek6699

8.3K views
Not available in United States

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

25.4K views
Not available in United States

21:51
British MILF Lisa spanks sissy Charlotte
Lisa Essex

22.2K views
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23:50
Doc punishing his bratty submissive femboy sissy Michele
Sissy Michelle MTF

95.9K views
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12:23
Sissy slut non stop edging as punishment
CindySissy

29.4K 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

9.4K views
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01:40
My Deep Throat
KatyKoroleva

9.7K 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

17.7K views
Not available in United States

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

29.1K views
Not available in United States

05:50
Shemale mistress in high heeled boots punishes her slave by destroying his ass
Marika Ferreira

29.8K views
Not available in United States

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

5.9K views
Not available in United States

05:08
FGO Spy Cosplayer Defeat by the Enemy, she receives various Sexual punishments from enemies, Asian femboy ladyboy latex
Haru

13.8K views
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05:08
Kelli gagged with a pee covered penis gag
Kelli UK

6.3K views
Not available in United States

17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.2K views
Not available in United States

01:01
Trying some new devices
Aliska

14.6K views
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01:13
Guy Transformed into Hot Woman as Punishment by Roommate
Bailey Wilde

7.4K views
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00:38
Sucker for Punishment
Jennifer Lunden

10.2K views
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05:51
Ozriel Whipping Cock and Shaking Ass
Oznob Oznofla

10.3K views
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08:01
MATURE CROSSDRESSER TVROSE COCK, BALLS AND ASS PUNISHED

23.2K views
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15:26
Story of Kt - part 1 meeting my mistress April
Loyalfans

7.2K views
Not available in United States

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

9.6K views
Not available in United States

18:23
10 Minutes of Torment
Derek6699

15.2K views
Not available in United States

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

2.7K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

15.6K views
Not available in United States

20:25
Jayci's sissy clitty punishment
Sissy Jayci

2.4K views