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Punished: 166 Movies, sorted by Popularity

Crossdresser Spanking

Crossdresser Spanking

01:38
Torturing of babes sexy assets

Torturing of babes sexy assets

05:09
Crossdresser Punishment Milking

Crossdresser Punishment Milking

09:02
Simatra Nursery Panthere Panties Punish Anal # 1

Simatra Nursery Panthere Panties Punish Anal # 1

03:00
Spanking slowmotion

Spanking slowmotion

43:38
One guy gets punished with six shemale dicks

One guy gets punished with six shemale dicks

05:05
Sissy gets Strapon punishment

Sissy gets Strapon punishment

08:23
TS Yoga Instructor Dominates Foot-Sniffer

TS Yoga Instructor Dominates Foot-Sniffer

10:55
Strict hostess punishes her maid

Strict hostess punishes her maid

11:45
Sissy Boy Punished Hard

Sissy Boy Punished Hard

08:19
My strict Mistress punishes me

My strict Mistress punishes me

16:21
TS Domme Punishing Slave

TS Domme Punishing Slave

05:30
Dominant Shemale Punishers In Full Action

Dominant Shemale Punishers In Full Action

05:14
Dominant Shemale Punishers In Full Action

Dominant Shemale Punishers In Full Action

05:14
Tammy's Hairbrush Punishment for Spending Too Much Money.

Tammy's Hairbrush Punishment for Spending Too Much Money.

00:52
Mistresses punishing man

Mistresses punishing man

11:30
Suck my dick for your punishment for not paying me

Suck my dick for your punishment for not paying me

06:43
Anna's harsh self-punishment with two cables .

Anna's harsh self-punishment with two cables .

24:33
Crossdresser punish with candles

Crossdresser punish with candles

06:47
Mature trans covers herself with spunk

Mature trans covers herself with spunk

06:02
Dude Punished With Giant Long Black Cock

Dude Punished With Giant Long Black Cock

11:47
TRANSFIXED - OOPSIE! House Robber Korra Del Rio Is Caught By Couple And Tag Teamed As Punish

TRANSFIXED - OOPSIE! House Robber Korra Del Rio Is Caught By Couple And Tag Teamed As Punish

14:06
Gangbanged TS punished with cum in own mouth

Gangbanged TS punished with cum in own mouth

10:00
Perfect TS Punishment

Perfect TS Punishment

09:34
Femdom shemale punish cuckold

Femdom shemale punish cuckold

12:17
Sissy Audrey Punished

Sissy Audrey Punished

07:14
Simatra Sexy Brunette Fat Beauty Ass Fuck Anal Punish hardcore # 2

Simatra Sexy Brunette Fat Beauty Ass Fuck Anal Punish hardcore # 2

04:38
TS Jesse Punishes a Cis and TS Man!

TS Jesse Punishes a Cis and TS Man!

10:11
Naughty TGirl maids get bondage and ass spanking punishment

Naughty TGirl maids get bondage and ass spanking punishment

10:11
Naughty TGirl maids bondage spanking punishment for caught playing together

Naughty TGirl maids bondage spanking punishment for caught playing together

10:10
Raid over Japan , Asian Ladyboy punished and fucked in the ass hardcore

Raid over Japan , Asian Ladyboy punished and fucked in the ass hardcore

26:03
Six shemale cops punish just one criminal man

Six shemale cops punish just one criminal man

05:05
3 shemale punishers

3 shemale punishers

19:31
Krissy gets Punished

Krissy gets Punished

11:39
punishment shemale fucking

punishment shemale fucking

19:32
Big Boys Punish A Bad Tranny Slut

Big Boys Punish A Bad Tranny Slut

24:27
Crossdresser Punishment

Crossdresser Punishment

15:28
Isadora Venturini And Rayna Leah - Cock Hungry Shemales Ganging Up On Their Slave

Isadora Venturini And Rayna Leah - Cock Hungry Shemales Ganging Up On Their Slave

05:00
Buxom tranny in stockings Rabeche has a hung dude punishing her ass

Buxom tranny in stockings Rabeche has a hung dude punishing her ass

10:00
Anal punishment for naughty cd

Anal punishment for naughty cd

08:21
crossdresser slave bitch

crossdresser slave bitch

33:34
That needs some punishment

That needs some punishment

55:33
Strict hostess punishes her maid

Strict hostess punishes her maid

11:45
Naughty smoking blonde TGirl maid has tight ass spanked as kinky punishment

Naughty smoking blonde TGirl maid has tight ass spanked as kinky punishment

10:07
Police ladyboy punishes brunette with her dick

Police ladyboy punishes brunette with her dick

30:47
Dorm Room Punishment

Dorm Room Punishment

06:37
Sissy Boy Punished Hard

Sissy Boy Punished Hard

08:19
Hardcore sex in a dungeon with tranny punishment

Hardcore sex in a dungeon with tranny punishment

24:17
Tslut punished at hotel room

Tslut punished at hotel room

17:18
Tranny domina punishing her tied up bf

Tranny domina punishing her tied up bf

12:33
Severe punishments with lash for big balloons shemale

Severe punishments with lash for big balloons shemale

04:38
Corporal Punishment Session Pt 01 4-16-2019

Corporal Punishment Session Pt 01 4-16-2019

44:53
Crossdresser Punishment

Crossdresser Punishment

04:06
Naughty TGirl Maid given full punishment spanking and anal fuck by mistress big strapon

Naughty TGirl Maid given full punishment spanking and anal fuck by mistress big strapon

10:55
This busty slut needs to be punish

This busty slut needs to be punish

26:04
Domme shemale cop Sasha Strokes fucks thief for punishment

Domme shemale cop Sasha Strokes fucks thief for punishment

05:26
Lance Hart Is Given To TS Foxxy For Punishment

Lance Hart Is Given To TS Foxxy For Punishment

08:49
Horny Shemale Karen Venus Punishing A Fat Pussy

Horny Shemale Karen Venus Punishing A Fat Pussy

05:00
Hot punishment from a vintage shemale

Hot punishment from a vintage shemale

10:22
Teen TS punishing

Teen TS punishing

25:58
Pre op trans girl slut Sarah gets punished by her wife mistress Petula

Pre op trans girl slut Sarah gets punished by her wife mistress Petula

11:29
Guy Gets Punished By Shemales

Guy Gets Punished By Shemales

10:04
Sara wants you to cum by artificial inte

Sara wants you to cum by artificial inte

10:09
Encasement, shemale nylon cumshot

Encasement, shemale nylon cumshot

22:47
Hard spanking

Hard spanking

10:51
Gorgeous TS Secretary Dominates Boss

Gorgeous TS Secretary Dominates Boss

05:13
Two girlfriends being punished by a hard cock

Two girlfriends being punished by a hard cock

24:18
Kinky boy has a busty black tranny punishing his tight ass on the bed

Kinky boy has a busty black tranny punishing his tight ass on the bed

10:00
guy gets feminized and ass fucked in prison by chick

guy gets feminized and ass fucked in prison by chick

18:05
Brutal shemale punished hard

Brutal shemale punished hard

05:53
3 Shemales Punish Him

3 Shemales Punish Him

02:21
Ts Goddess Foxxy Punishes Loser Boyfriend

Ts Goddess Foxxy Punishes Loser Boyfriend

10:31
Absolute stunner punishes her man for wetting her top

Absolute stunner punishes her man for wetting her top

10:59
Horny shemale punishing a wet pussy

Horny shemale punishing a wet pussy

05:00
TSgirl punished intensely by a massive cock - amazing POV

TSgirl punished intensely by a massive cock - amazing POV

10:31
Gangbanged TS punished with cum in own mouth

Gangbanged TS punished with cum in own mouth

10:00
Rayna Leah and Isadora Venturini 3Way Tranny Sex

Rayna Leah and Isadora Venturini 3Way Tranny Sex

05:01
Beautiful teenie punishment

Beautiful teenie punishment

40:31
Corporal Punishment Session Pt 02 4-16-2019

Corporal Punishment Session Pt 02 4-16-2019

45:03
Devastatingly Seductive Ts Yasmin Lee punishes Reed with a Deep Hard Fucking

Devastatingly Seductive Ts Yasmin Lee punishes Reed with a Deep Hard Fucking

04:00
Tranny punished another one like a doggyp

Tranny punished another one like a doggyp

10:45
Nasty blonde needs to be punish

Nasty blonde needs to be punish

24:41
Handsome young stud has a black shemale punishing his ass on the bed

Handsome young stud has a black shemale punishing his ass on the bed

10:00
Lustful white boy seduces a buxom black tranny to punish his needy ass

Lustful white boy seduces a buxom black tranny to punish his needy ass

10:00
Stud Punished By Black Shemale Cock

Stud Punished By Black Shemale Cock

10:37
Sissy in stockings gets Anal Punishment from his Mistress

Sissy in stockings gets Anal Punishment from his Mistress

14:32
Amateur, sissy, Skinny, Slave, Ass, Anal, punishment,

Amateur, sissy, Skinny, Slave, Ass, Anal, punishment,

14:10
9999cams-blogspot Girl, punished by older man on webcam

9999cams-blogspot Girl, punished by older man on webcam

10:05
Crossdresser punishment

Crossdresser punishment

28:19
TS Domme Punishing Slave

TS Domme Punishing Slave

05:30
Crossdresser punishment

Crossdresser punishment

21:13
shemale4ever aspen brooks punishes kip johnson

shemale4ever aspen brooks punishes kip johnson

10:27
Sexy Milf gives horny big cock TGirl ass and cock punishment

Sexy Milf gives horny big cock TGirl ass and cock punishment

06:38
Hot trannies punishing stud

Hot trannies punishing stud

22:56
TS Domme Punishing Slave

TS Domme Punishing Slave

05:30
Beautiful stud Junior invites a buxom black tranny to punish his ass

Beautiful stud Junior invites a buxom black tranny to punish his ass

10:00
Shemale punishers

Shemale punishers

19:04
Kay One by Bushido

Kay One by Bushido

11:23
Bad Tranny Punished Outdoors

Bad Tranny Punished Outdoors

26:07
Crossdresser punishing her bf's ass for being naughty

Crossdresser punishing her bf's ass for being naughty

11:56
TS Yoga Instructor Dominates Foot-Sniffer

TS Yoga Instructor Dominates Foot-Sniffer

10:55
Asian Ladyboy dominatrix punishing a slave client with a small micro dick faggot

Asian Ladyboy dominatrix punishing a slave client with a small micro dick faggot

15:13
Punish this horny ass

Punish this horny ass

22:51
They punish a married dude while his gf is filming

They punish a married dude while his gf is filming

10:40
Shemale punishes guy

Shemale punishes guy

17:23
crossdresser spanking

crossdresser spanking

28:18
debbie heart tv whipping myself for my mistress

debbie heart tv whipping myself for my mistress

04:05
Punishing my transgender Wife for starting arguement with me

Punishing my transgender Wife for starting arguement with me

01:03
Punished and fucked in my Sissy fuck hole

Punished and fucked in my Sissy fuck hole

12:07
Threeway Punishment

Threeway Punishment

26:16
Master turns tranny slave into cock sucking cum slut after ass punishment

Master turns tranny slave into cock sucking cum slut after ass punishment

10:09
Aspen Brooks Punishes Kip Johnson

Aspen Brooks Punishes Kip Johnson

10:17
Two sultty Halloween trannys give eachother blowjobs and swallow thick cum

Two sultty Halloween trannys give eachother blowjobs and swallow thick cum

10:47
Punished by Shemale Nuns

Punished by Shemale Nuns

40:00
Naughty smoking blonde TGirl maid has tight pert ass spanked for hot kinky punishment

Naughty smoking blonde TGirl maid has tight pert ass spanked for hot kinky punishment

10:03
Petite brunette tranny gets her ass punished

Petite brunette tranny gets her ass punished

19:16
Naughty TGirl maids get bondage and spanking punishment after being caught playing together

Naughty TGirl maids get bondage and spanking punishment after being caught playing together

10:10
TS Goddess POV Punishment

TS Goddess POV Punishment

07:00
Mistress Jamie - Corporal Punishment Session Pt 02 4-13-2019

Mistress Jamie - Corporal Punishment Session Pt 02 4-13-2019

30:04
Punishment 4 the slut

Punishment 4 the slut

10:36