13.9K Results

Crossdressers Punishment Porn Videos

Free Porn Videos

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

144.6K views
Not available in United States

36:35
Sissy Maid Self Bondage Electro Punishment
Derek6699

36.8K views
Not available in United States

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

49.2K views
Not available in United States

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

90.8K views
Not available in United States

11:33
Hard punishment and sex. KitsyMe0w
Kitsy Meow

66K views
Not available in United States

11:12
Roommate Feminized and Fucked for Punishment
Bailey Wilde

24.5K views
Not available in United States

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

126.4K views
Not available in United States

04:47
Sunday punishment by Master
PA8mmMaster

14.1K 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

38.4K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

42.3K views
Not available in United States

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

16.2K views
Not available in United States

08:18
Valentine's Day 1
KatyKoroleva

15.1K 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

6.1K views
Not available in United States

01:40
My Deep Throat
KatyKoroleva

7.6K views
Not available in United States

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

79.6K views
Not available in United States

21:51
British MILF Lisa spanks sissy Charlotte
Lisa Essex

19.7K views
Not available in United States

06:18
Punishment For A Naughty School Gurl
Chantal Fouet

6K views
Not available in United States

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

23K views
Not available in United States

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

20.7K views
Not available in United States

12:23
Sissy slut non stop edging as punishment
CindySissy

13.7K views
Not available in United States

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

6.2K views
Not available in United States

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

4.2K 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

11.6K views
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05:51
Ozriel Whipping Cock and Shaking Ass
Oznob Oznofla

8.1K views
Not available in United States

01:01
Trying some new devices
Aliska

13.6K views
Not available in United States

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

4.8K views
Not available in United States

20:25
Jayci's sissy clitty punishment
Sissy Jayci

1.9K views
Not available in United States

07:53
Sissy Maids Punishment
Derek6699

12.9K views
Not available in United States

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

26.3K views
Not available in United States

02:41
Walking in the grocery store
Sissy Michelle MTF

3.7K views
Not available in United States

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

1.6K views
Not available in United States

04:57
Leather BDSM tease
JessicaXD

4.8K views
Not available in United States

01:13
Guy Transformed into Hot Babe as Punishment by Female Roommate
Bailey Wilde

3.2K views
Not available in United States

11:43
Kitsy gets hand spanked OTK.
Kitsy Meow

4.5K views
Not available in United States

50:12
Horny small cock tranny jerking off, ordering and getting take away live on stream, and punished for being naughty
AnnYRegn

7.2K views
Not available in United States

05:57
DRIPPING HOT WAX ON MY COCK
Kenzie Star

2.3K views
Not available in United States

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

2.2K views
Not available in United States

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

4.3K views
Not available in United States

02:40
Sissy Punished for Being a Bad Roommate
Bailey Wilde

1.7K views
Not available in United States

02:32
caging my tiny limp cock back up
s sisswewt

2.2K views
Not available in United States

03:33
Sissy Camilla dressed for fucking and taking punishment to get ready for daddy
Sissy Camilla

2K 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

8.7K views
Not available in United States

03:41
The Pressure of Pain and Punishment
BadGod

2.2K views
Not available in United States

01:21
Man Made into Woman by Roommate as Punishment
Bailey Wilde

2.8K views
Not available in United States

03:33
flogging my sissyclit because I was a bad sissy
Emma Huntcock

2.3K views
Not available in United States

07:48
Playing My Self
KatyKoroleva

1.5K views
Not available in United States

23:49
Naughty trans NB punishes herself with spanking and gets rewarded by her vibrator
AnnYRegn

1.7K views