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6 years ago
8:02

TrannyOne

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3 years ago
20:26

TrannyOne

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1 year ago
7:43

aShemaleTube

Tranny was naughty so she got punished anally

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1 year ago
7:00

ShemaleSin

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SPANKING THE MONKEY #04 - (FULL HD Movie Original Version)
2 years ago
30:53

TrannyOne

SPANKING THE MONKEY #04 - (FULL HD Movie Original Version)

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TBabe Jenna Tales punish Chads butthole
6 years ago
6:11

TrannyOne

TBabe Jenna Tales punish Chads butthole

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3 years ago
6:49

TrannyOne

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Helium Air Clyster For Crazy Meaty Butt T-Model COUGAR Karolina
2 years ago
8:37

KeekAss

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taskmaster Turns blonde lady-man bondman Suzie Into penis sucking sperm skank After Her anal spanking punishment
6 years ago
9:40

ShemaleZ

taskmaster Turns blonde lady-man bondman Suzie Into penis sucking sperm skank After Her anal spanking punishment

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Punished For Skipping Chores - 1/2 - Spanked And Paddled
2 years ago
23:38

ShemaleZ

Punished For Skipping Chores - 1/2 - Spanked And Paddled

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Feminized Pain Toy
3 years ago
2:58

TrannyOne

Feminized Pain Toy

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Punished For Skipping Chores - 2/2 - Spanked On The Hole And Plugged
2 years ago
9:41

ShemaleZ

Punished For Skipping Chores - 2/2 - Spanked On The Hole And Plugged

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Korra Del Rio - Tranny Nun Punishes A Dirty Sinner!
3 years ago
3:30

ShemaleZ

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2 years ago
4:24

TrannyOne

Sucking Nylon cock an spanking

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2 years ago
13:55

TrannyOne

Kinky ladyboy dominates an innocent bald guy in the hardcore bondage fuck

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Sexy tranny spreads her cute little feet for some anal punishment
2 years ago
9:43

aShemaleTube

Sexy tranny spreads her cute little feet for some anal punishment

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Hot Fucked First Wives' Club - The Punishment Of An Unfaithful Husband Series, Part 4
3 years ago
4:51

BeMyHole

Hot Fucked First Wives' Club - The Punishment Of An Unfaithful Husband Series, Part 4

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She was naughty and got punished for it
2 years ago
7:12

aShemaleTube

She was naughty and got punished for it

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Pimp and prostitute-shemale punished prostitute-rival
6 years ago
5:58

ShemaleZ

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Shemale Yasmin Fonthys Dominate Her Man and Punishes Him Till Orgasm
2 years ago
8:03

aShemaleTube

Shemale Yasmin Fonthys Dominate Her Man and Punishes Him Till Orgasm

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River Enza punishes big tranny asshole with dildo
1 year ago
9:34

aShemaleTube

River Enza punishes big tranny asshole with dildo

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2 years ago
3:35

ShemaleSin

DWT Thrall with gigantic silicone Melons and a great Outfit - My Bazookas torso with enormous Monster Bazookas and my longest and thickest Toys for bi

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Ebony shemale punishing a white guy's asshole
1 year ago
3:50

aShemaleTube

Ebony shemale punishing a white guy's asshole

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Bustylicious Ts Punishing Her German Slave
2 years ago
7:38

ShemaleZ

Bustylicious Ts Punishing Her German Slave

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2 years ago
6:31

aShemaleTube

Thick tattooed tranny punishes a dude raw

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Sissy Princess getting punished an Owned by Madam Kitty Kaos
1 year ago
18:09

aShemaleTube

Sissy Princess getting punished an Owned by Madam Kitty Kaos

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1 year ago
3:40

aShemaleTube

CD mistress punish and fuck her slut

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2 years ago
3:43

ShemaleSin

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Punish-fucked By Head Mistress Starlight Preview With Ally Sparkles And Johnny Starlight
1 year ago
7:35

ShemaleZ

Punish-fucked By Head Mistress Starlight Preview With Ally Sparkles And Johnny Starlight

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Pink haired cutie spreads her legs for anal punishment
2 years ago
5:24

aShemaleTube

Pink haired cutie spreads her legs for anal punishment

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Chained and gagged first-timer attempts to ride massive dildo while being punished
1 year ago
18:40

ShemaleTaxi

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2 years ago
2:27

aShemaleTube

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2 years ago
8:07

aShemaleTube

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2 years ago
10:54

ShemaleTaxi

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four Eggs in Arse and Plumb It Rock-Hard Out of Me
1 year ago
2:12

KeekAss

four Eggs in Arse and Plumb It Rock-Hard Out of Me

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Crossdressed twink fucked bareback by straight curious Arab
2 years ago
20:58

TrannyOne

Crossdressed twink fucked bareback by straight curious Arab

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Two friends humiliate and punish a sissy
1 year ago
2:55

aShemaleTube

Two friends humiliate and punish a sissy

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Gagged, Handcuffed, and Drooling from Climax Punishment
2 years ago
7:59

ShemaleSin

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Spanked and dominated stud anal fucked by Asian TS Venus Lux
3 years ago
6:00

TrannyOne

Spanked and dominated stud anal fucked by Asian TS Venus Lux

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Slender tranny punishes her mischievous fat bf
2 years ago
6:50

aShemaleTube

Slender tranny punishes her mischievous fat bf

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She has a hot anal orgasm as a fan punishes her ass
2 years ago
6:13

aShemaleTube

She has a hot anal orgasm as a fan punishes her ass

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Medic penalizing his bratty obedient femboy sissy Michele
2 years ago
23:50

KeekAss

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2 years ago
6:18

aShemaleTube

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Latin ts in lingerie punishing a dude's mouth and ass
2 years ago
8:08

aShemaleTube

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2 years ago
5:18

ShemaleSin

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1 year ago
4:46

aShemaleTube

Shemale mistress stayed home to punish her slave

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1 year ago
15:01

ShemaleTaxi

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Brunette slim shemale babe punishes bound slave's cock and ass
6 years ago
8:06

TrannyOne

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Don't Do It Again
3 years ago
20:30

TrannyOne

Don't Do It Again

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Tranny Nun Punishes a Dirty Sinner!
1 year ago
4:00

TrannyOne

Tranny Nun Punishes a Dirty Sinner!

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She male Ebony Mistess
2 years ago
25:21

FetishPapa

She male Ebony Mistess

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2 years ago
9:32

ShemaleTaxi

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2 years ago
7:25

ShemaleTaxi

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Post Climax Punishment Compilation. 4 Outstanding Cumshots
4 years ago
4:46

ShemaleSin

Post Climax Punishment Compilation. 4 Outstanding Cumshots

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Sissy Punish Sissy
1 year ago
17:18

ShemaleZ

Sissy Punish Sissy

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DOMINATION & SUBMISSION Transgender Princess Lactation Tough Penalty Homonate Perky Knockers Ladyboy
1 year ago
14:51

KeekAss

DOMINATION & SUBMISSION Transgender Princess Lactation Tough Penalty Homonate Perky Knockers Ladyboy

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Enchanting punishment
3 years ago
1:47

ShemaleSin

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Mistress T punishing sissy with big toys
2 years ago
23:41

TrannyOne

Mistress T punishing sissy with big toys

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1 year ago
2:38

aShemaleTube

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Rafael Almeida And Marika Ferreira In Shemale Mistress In High Heeled Boots Punishes Her Slave By Destroying His Ass 6 Min
1 year ago
5:15

ShemaleZ

Rafael Almeida And Marika Ferreira In Shemale Mistress In High Heeled Boots Punishes Her Slave By Destroying His Ass 6 Min

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One guy gets punished with six shemale dicks
4 years ago
5:05

TrannyOne

One guy gets punished with six shemale dicks

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A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE
3 years ago
16:23

TrannyOne

A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE

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Blonde sissy Charlotte punished with intense spanking and caning by master Mike
1 year ago
37:46

ShemaleTaxi

Blonde sissy Charlotte punished with intense spanking and caning by master Mike

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Shemales Punish Guy
4 years ago
5:08

TrannyOne

Shemales Punish Guy

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Naughty Teen Shemales Deepthroat and Ass Spanking
3 years ago
10:36

TrannyOne

Naughty Teen Shemales Deepthroat and Ass Spanking

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Busty Ebony Tranny Punishes A Thief On The Floor
1 year ago
6:11

FlyFlv

Busty Ebony Tranny Punishes A Thief On The Floor

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Saturday Impact play with Michelle
2 years ago
32:06

TrannyOne

Saturday Impact play with Michelle

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Transsexual mistress Aubrey Kate punishes deep throat and anal hole of submissive dude
5 years ago
4:00

AnySex

Transsexual mistress Aubrey Kate punishes deep throat and anal hole of submissive dude

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Cheating sissy trap jerking in a golden satin silk long maxi sundress
2 years ago
3:50

KeekAss

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Schlong and ball punishment, vibrated clitoris and good spunk flow...
2 years ago
9:08

ShemaleSin

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Ashley Is Spanked And Rimmed
3 years ago
4:29

TrannyOne

Ashley Is Spanked And Rimmed

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Arabic squirt compilation 4
2 years ago
4:37

TrannyOne

Arabic squirt compilation 4

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Busty amateur transsexual solo pulling dick
3 years ago
6:07

TrannyOne

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Feminized and Spanked
3 years ago
5:29

TrannyOne

Feminized and Spanked

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Large shaggy pussy clamped and widen out in a vagina dreamcatcher for snatch punishment, stretching, figging, tough sextoy screwing. Preview / teaser
2 years ago
2:27

ShemaleSin

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3 years ago
2:53

TrannyOne

Sissy boy twerks

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2 years ago
2:43

ShemaleSin

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Hot t-girl punishes a slender man hard.
2 years ago
6:31

ShemaleSin

Hot t-girl punishes a slender man hard.

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Spit-roasted And Treated Like A Plaything
3 years ago
10:35

TrannyOne

Spit-roasted And Treated Like A Plaything

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PornHolidays 4
5 years ago
35:19

KeekAss

PornHolidays 4

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doggystyle and spanking
3 years ago
3:29

TrannyOne

doggystyle and spanking

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Blonde fucked in the ass in public
3 years ago
5:18

TrannyOne

Blonde fucked in the ass in public

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AnitaForYou The Submissive
3 years ago
4:19

TrannyOne

AnitaForYou The Submissive

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Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad
3 years ago
19:45

TrannyOne

Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad

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Fetish tgirl gets spanked
3 years ago
5:30

TrannyOne

Fetish tgirl gets spanked

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In this amateur collection hot and horny shemales dominate their male partners in hardcore anal sex
2 years ago
39:26

TrannyOne

In this amateur collection hot and horny shemales dominate their male partners in hardcore anal sex

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2 years ago
1:53

TrannyOne

Fer, mi papi me hace suya de nuevo

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Sissy Crossdresser maninlace81 in detention part 3
3 years ago
12:42

TrannyOne

Sissy Crossdresser maninlace81 in detention part 3

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Yasmin Fonthys - Shemale Dominate Her Man And Punishes Him Till Orgasm
2 years ago
7:34

ShemaleZ

Yasmin Fonthys - Shemale Dominate Her Man And Punishes Him Till Orgasm

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Slender tranny punishes a gay dude hard
2 years ago
7:08

aShemaleTube

Slender tranny punishes a gay dude hard

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Sissy slave Harley Quinn punished and fucked xhqtFb3
2 years ago
5:09

TrannyOne

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Dumb sissy bitch was a bad angel. So dad punished her butt until it was red.
3 years ago
2:04

ShemaleSin

Dumb sissy bitch was a bad angel. So dad punished her butt until it was red.

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Big cock shemale nun punishes sinner
4 years ago
4:53

BeMyHole

Big cock shemale nun punishes sinner

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Tranny Punishing Guys Asshole
3 years ago
5:41

ShemaleZ

Tranny Punishing Guys Asshole

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A Private Punishment With Natalie Mars
3 years ago
6:57

ShemaleZ

A Private Punishment With Natalie Mars

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Dudes caught transexual and punished him orally and anally
7 years ago
37:36

TrannyOne

Dudes caught transexual and punished him orally and anally

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Rough anal treatment for Tranny Sabina
3 years ago
5:17

TrannyOne

Rough anal treatment for Tranny Sabina

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Submissive guy serves his thick ass to the hot and horny ebony Tgirl with a BBC
3 years ago
28:15

TrannyOne

Submissive guy serves his thick ass to the hot and horny ebony Tgirl with a BBC

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Me with my mate
3 years ago
6:12

TrannyOne

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Doctor femboy dong and ball punishment session POV! (Trailer)
1 year ago
0:32

ShemaleSin

Doctor femboy dong and ball punishment session POV! (Trailer)

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Shemale police officers punish a man
4 years ago
6:28

aShemaleTube

Shemale police officers punish a man

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Muscle man gets dominated by the nasty TS chick in this hardcore sex
3 years ago
42:36

TrannyOne

Muscle man gets dominated by the nasty TS chick in this hardcore sex

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Busty exotic shemale babe punishes and fucks her young slave
6 years ago
8:07

TrannyOne

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3 years ago
10:56

TrannyOne

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Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad
3 years ago
15:58

TrannyOne

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Poor guy moans loudly as the beautiful tranny babe bangs him hard
3 years ago
15:29

TrannyOne

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TS mastix Shiri Allwood plays with her captive servant in the dungeon. This Chab sucks her weenie and balls in a sexy sixty-nine. The youthful and hot
2 years ago
4:11

ShemaleSin

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1 year ago
4:05

ShemaleSin

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Beautiful and curvy shemale dom punishes her male slave's ass
6 years ago
8:02

TrannyOne

Beautiful and curvy shemale dom punishes her male slave's ass

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Ladyboy BDSM punished and sucking cock and getting anal
3 years ago
7:14

aShemaleTube

Ladyboy BDSM punished and sucking cock and getting anal

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Mature Shemale Fuck And Punish Old Bastard
3 years ago
4:38

ShemaleZ

Mature Shemale Fuck And Punish Old Bastard

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PornHolidays 2
5 years ago
33:09

KeekAss

PornHolidays 2

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Gorgeous shemale secretary Yasmine Lee punishes her sexist boss' asshole
6 years ago
42:30

AshemaleOne

Gorgeous shemale secretary Yasmine Lee punishes her sexist boss' asshole

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Tall TS Domme Punishes Beefcake Lance
7 years ago
11:00

xHamster

Tall TS Domme Punishes Beefcake Lance

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TS domina punishes her submissive slave
5 years ago
6:06

aShemaleTube

TS domina punishes her submissive slave

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3 years ago
10:57

ShemaleTaxi

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Ts domina punishes her handsome slave
5 years ago
6:00

aShemaleTube

Ts domina punishes her handsome slave

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Indoors And Short Hair Boyfriend PUNISHMENT - TS Foxxy Pounds Loser Boyfriend Mike Panic's Ass, Part 9
3 years ago
4:51

BeMyHole

Indoors And Short Hair Boyfriend PUNISHMENT - TS Foxxy Pounds Loser Boyfriend Mike Panic's Ass, Part 9

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tony naked and punishing his male slave nipples
3 years ago
12:24

HClips

tony naked and punishing his male slave nipples

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Ts Punishment
2 years ago
48:08

ShemaleZ

Ts Punishment

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Latex wearing transgender babe tortures and fucks a helpless slave without a condom
3 years ago
6:48

TrannyOne

Latex wearing transgender babe tortures and fucks a helpless slave without a condom

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crossdresser spanking
3 years ago
12:56

aShemaleTube

crossdresser spanking

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Youthful lad gets caught sniffing her pants, so that babe punishes him by   him to choke down her thick chunky schlong, previous to violating his taut
4 years ago
24:46

ShemaleSin

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Punished And Fucked Xhqtfb3 With Sissy Slave And Harley Quinn
2 years ago
4:39

HClips

Punished And Fucked Xhqtfb3 With Sissy Slave And Harley Quinn

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Femboy biotch gets firm arse slapping as penalty (SissySandyy20 Solo)
2 years ago
3:43

KeekAss

Femboy biotch gets firm arse slapping as penalty (SissySandyy20 Solo)

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Hot TS Anal Punishment
4 years ago
4:59

BeMyHole

Hot TS Anal Punishment

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Teased and punished tranny
5 years ago
3:25

ShemaleZ

Teased and punished tranny

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WOMEN POWER, or Adult games of hot mature couple from Russia
3 years ago
22:48

TrannyOne

WOMEN POWER, or Adult games of hot mature couple from Russia

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Makeup Pause And Punishment
3 years ago
7:11

ShemaleZ

Makeup Pause And Punishment

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Busted Watching Porn at Work-Boss Punishes Bad Employee w/Her Own Cock
8 years ago
4:00

ShemaleZ

Busted Watching Porn at Work-Boss Punishes Bad Employee w/Her Own Cock

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Nun Punishing Butt Fuck Male Prisoner
3 years ago
5:09

ShemaleZ

Nun Punishing Butt Fuck Male Prisoner

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Tranny Soccer Players Punishing Sales Referee
3 years ago
28:14

ShemaleZ

Tranny Soccer Players Punishing Sales Referee

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Blonde Dirty Talking Blond Heshe Punishes A Bald Dude
3 years ago
6:21

BeMyHole

Blonde Dirty Talking Blond Heshe Punishes A Bald Dude

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Transsexual Milf Punished Her Latina Maid With Hard Sex 8 Min
2 years ago
7:30

ShemaleZ

Transsexual Milf Punished Her Latina Maid With Hard Sex 8 Min

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mistress Jamie - corporal Punishment Session Pt 0four 4-13-2019
3 years ago
30:34

ShemaleTaxi

mistress Jamie - corporal Punishment Session Pt 0four 4-13-2019

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Tranny gets anally punished
2 years ago
6:20

aShemaleTube

Tranny gets anally punished

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Innocent lad gets punished by her tranny boss with hot anal pounding
4 years ago
6:42

BeMyHole

Innocent lad gets punished by her tranny boss with hot anal pounding

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Interracial The Sketch Artist - Model Natassia Dreams Punishes Pathetic Creep, Part 7
3 years ago
4:52

BeMyHole

Interracial The Sketch Artist - Model Natassia Dreams Punishes Pathetic Creep, Part 7

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crossdresser punishment
3 years ago
1:13:13

aShemaleTube

crossdresser punishment

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Mouth Fucking The League Of Extraordinary Transsexuals - The Final Punishment, Part 4
3 years ago
4:52

BeMyHole

Mouth Fucking The League Of Extraordinary Transsexuals - The Final Punishment, Part 4

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Facesitting All For You - A Pleasure-Filled POV Punishment, Part 6
3 years ago
4:52

BeMyHole

Facesitting All For You - A Pleasure-Filled POV Punishment, Part 6

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Sissy-training, punishment
4 years ago
25:05

ShemaleTaxi

Sissy-training, punishment

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Laela Knight Punishes Line Jumper
10 years ago
5:07

aShemaleTube

Laela Knight Punishes Line Jumper

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Hung blond shemale punishes a guy
2 years ago
7:06

aShemaleTube

Hung blond shemale punishes a guy

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Small Cock Sissy Cums Hard
3 years ago
30:18

TrannyOne

Small Cock Sissy Cums Hard

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Punish my incredible thick ass
2 years ago
8:10

aShemaleTube

Punish my incredible thick ass

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Sissy In Stockings Gets Anal Punishment From His Mistress
3 years ago
14:03

ShemaleZ

Sissy In Stockings Gets Anal Punishment From His Mistress

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Dominate The Naughty Nun - Korra Del Rio Punishes Disgraceful Sinner DJ, Part 8
3 years ago
4:51

BeMyHole

Dominate The Naughty Nun - Korra Del Rio Punishes Disgraceful Sinner DJ, Part 8

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naughty TGirl maids bondage smacking punishment for caught toying together
4 years ago
10:20

ShemaleMovie

naughty TGirl maids bondage smacking punishment for caught toying together

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FemDom Lifestyle - sissy maid scolded and punished
5 years ago
7:36

ShemaleZ

FemDom Lifestyle - sissy maid scolded and punished

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Mature stockings, shemale punishment
3 years ago
43:45

ShemaleTaxi

Mature stockings, shemale punishment

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Fat Slut deserve punishment from her Transgender Dominatrix
4 years ago
9:49

xHamster

Fat Slut deserve punishment from her Transgender Dominatrix

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Sissy Slave Tranny Punished & Fucked - Full Video
3 years ago
10:46

xHamster

Sissy Slave Tranny Punished & Fucked - Full Video

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Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass
4 years ago
12:56

BeMyHole

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

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Sex Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig, Part 5
3 years ago
4:52

BeMyHole

Sex Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig, Part 5

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Punishment Dildoing by Diana
3 years ago
3:11

aShemaleTube

Punishment Dildoing by Diana

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Shemale Using Bond Slave For Their Pleasure
12 years ago
3:02

FlyFlv

Shemale Using Bond Slave For Their Pleasure

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A Private Punishment With Natalie Mars
3 years ago
7:03

ShemaleZ

A Private Punishment With Natalie Mars

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Sissy, punishment
2 years ago
10:16

ShemaleTaxi

Sissy, punishment

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TRANSSEXUAL Predominates Boy and Pops in his Throat!
5 years ago
3:17

KeekAss

TRANSSEXUAL Predominates Boy and Pops in his Throat!

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Tiny cocksluts bills penalty
3 years ago
10:18

KeekAss

Tiny cocksluts bills penalty

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Prissie Sissy Cock Punishment
3 years ago
6:36

ShemaleZ

Prissie Sissy Cock Punishment

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Strong Woman With A Big Cock Punishes An Insolent Thief
3 years ago
12:48

ShemaleZ

Strong Woman With A Big Cock Punishes An Insolent Thief

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Sissy Slave Tranny Punished Fucked Full Video xhgV9Vu 0
3 years ago
8:47

aShemaleTube

Sissy Slave Tranny Punished Fucked Full Video xhgV9Vu 0

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Phat Bum She-Male Mother Drilled with Romping Machine
2 years ago
11:01

KeekAss

Phat Bum She-Male Mother Drilled with Romping Machine

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#tgirl Sexy Shemale Punishes An Old Dude
2 years ago
5:16

BeMyHole

#tgirl Sexy Shemale Punishes An Old Dude

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Both Slaves Get Punished Together By Their Mistress
5 years ago
14:34

ShemaleZ

Both Slaves Get Punished Together By Their Mistress

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Sexy trans knockout Kayleigh Coxx issues rough punishment
4 years ago
6:53

HellPorno

Sexy trans knockout Kayleigh Coxx issues rough punishment

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Sexy Trans Student Andrea Will Be Punished
2 years ago
32:30

ShemaleZ

Sexy Trans Student Andrea Will Be Punished

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Sissy hard ass spanking
3 years ago
2:35

TrannyOne

Sissy hard ass spanking

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Busty heshe punishes a male fan
3 years ago
5:34

aShemaleTube

Busty heshe punishes a male fan

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Femtop.xxx - Roxxie Moth - Latex Sub Aphrodyte Adams Punished For Sneaking Out
3 years ago
32:28

ShemaleZ

Femtop.xxx - Roxxie Moth - Latex Sub Aphrodyte Adams Punished For Sneaking Out

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Wife Punished
3 years ago
3:42

ShemaleZ

Wife Punished

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Painslut Instructing with Sir James & Princess Kyaa in the Sensuous Agony Basement *directors Cut*
4 years ago
14:46

KeekAss

Painslut Instructing with Sir James & Princess Kyaa in the Sensuous Agony Basement *directors Cut*

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Dominant Ts Nurse Punishes Her Patient And Pounds His Ass - Yasmin Fonthys
3 years ago
8:12

ShemaleZ

Dominant Ts Nurse Punishes Her Patient And Pounds His Ass - Yasmin Fonthys

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Black strap ass trap Rosalina teaser
3 years ago
5:01

TrannyOne

Black strap ass trap Rosalina teaser

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Horny TS teacher punishes the naughty guy with her massive Tcock
4 years ago
6:05

BeMyHole

Horny TS teacher punishes the naughty guy with her massive Tcock

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Chubby Dude Punished By A Tranny Girl
2 years ago
7:03

HClips

Chubby Dude Punished By A Tranny Girl

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Cheating Man Punished By Shemale Dom
3 years ago
4:53

ShemaleZ

Cheating Man Punished By Shemale Dom

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Fake Boobs A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE
3 years ago
15:59

BeMyHole

Fake Boobs A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE

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