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2 years ago
33:55

TrannyOne

BBW mistress owning her CD slut

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Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!
8 years ago
4:00

TubeDupe

Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

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Woman Knob Penalizes Army Cadet
4 years ago
5:44

KeekAss

Woman Knob Penalizes Army Cadet

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Trans PornStar Taylor Jennings vs Femdom Alice Skary
2 years ago
1:29

TrannyOne

Trans PornStar Taylor Jennings vs Femdom Alice Skary

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My strict Mistress punishes me
11 years ago
16:21

aShemaleTube

My strict Mistress punishes me

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11 years ago
11:30

aShemaleTube

Mistresses punishing man

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7 years ago
5:53

DrTuber

Brutal shemale punished hard

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Threeway Punishment
11 years ago
26:16

aShemaleTube

Threeway Punishment

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Good looking babe with small tits and her punisher in the dungeon
8 days ago
10:18

xHamster

Good looking babe with small tits and her punisher in the dungeon

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13 years ago
4:38

aShemaleTube

Severe punishments with lash for big balloons shemale

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TS Chick Punished Hot
12 years ago
30:11

aShemaleTube

TS Chick Punished Hot

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Shemale punk Danni Daniels punishes her Tgirl sex slave Eva Lin
10 years ago
5:10

aShemaleTube

Shemale punk Danni Daniels punishes her Tgirl sex slave Eva Lin

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Pornstars: eva lin

Titty tranny punished guy
11 years ago
7:36

aShemaleTube

Titty tranny punished guy

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11 years ago
6:15

aShemaleTube

Tranny cop punishes shemale by spanking

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Sissy Audrey Punished
7 years ago
7:14

xHamster

Sissy Audrey Punished

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Femboy Slut Astolfo gets his ass destroyed and full of cum
2 years ago
16:16

TrannyOne

Femboy Slut Astolfo gets his ass destroyed and full of cum

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These Women Are Very Cruel
11 years ago
3:01

FlyFlv

These Women Are Very Cruel

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today I am your present, you can do what you want with me, I will let you suck it, you let me suck it 02
1 year ago
1:07

TrannyOne

today I am your present, you can do what you want with me, I will let you suck it, you let me suck it 02

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Submissive ladyboy mouth and booty punished
17 days ago
6:25

AnalDin

Submissive ladyboy mouth and booty punished

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Shemale Punishing Her Man
7 years ago
3:11

aShemaleTube

Shemale Punishing Her Man

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Trans in chastity punished and anal fucked
32 days ago
5:05

aShemaleTube

Trans in chastity punished and anal fucked

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

FlyFlv

Shemale Using Bond Slave For Their Pleasure

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Tranny Emma Lee Domination, Punishment and Discipline
8 years ago
5:15

aShemaleTube

Tranny Emma Lee Domination, Punishment and Discipline

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Submissive ladyboy whore got mouth and bum used
12 days ago
6:27

AnalDin

Submissive ladyboy whore got mouth and bum used

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Hot Brand Transsexual Diva Punishes a Guy
11 years ago
4:00

aShemaleTube

Hot Brand Transsexual Diva Punishes a Guy

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A Perfect Punishment!
8 years ago
4:00

TubeDupe

A Perfect Punishment!

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futanari professor punishing her pupil in a 3d animatio
4 days ago
2:00

aShemaleTube

futanari professor punishing her pupil in a 3d animatio

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Sissy Katelyn Drinks her own Piss (Sissy Punishment)
7 years ago
5:20

xHamster

Sissy Katelyn Drinks her own Piss (Sissy Punishment)

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Rough transsexual police officer punishes a naughty guy
10 years ago
5:10

aShemaleTube

Rough transsexual police officer punishes a naughty guy

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Enticing shemale punishes her boyfriend's ass the way he deserves it
7 years ago
10:00

DrTuber

Enticing shemale punishes her boyfriend's ass the way he deserves it

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Tied Up Man Gets Dominated By Three Shemales
11 years ago
2:59

FlyFlv

Tied Up Man Gets Dominated By Three Shemales

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7 years ago
24:23

Txxx

Caught and punished

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Agatha strokes her big cock while a hung stud punishes her anal hole
7 years ago
8:00

TubeON

Agatha strokes her big cock while a hung stud punishes her anal hole

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Punished By Her Dominating Cock
8 years ago
4:00

TubeDupe

Punished By Her Dominating Cock

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Cruel Shemale Punishment
13 years ago
3:10

aShemaleTube

Cruel Shemale Punishment

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Dominant Transsexuals Humiliate Submissive Male
11 years ago
2:58

FlyFlv

Dominant Transsexuals Humiliate Submissive Male

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First Wives' Club: The Punishment of an Unfaithful Husband Series
8 years ago
4:00

Txxx

First Wives' Club: The Punishment of an Unfaithful Husband Series

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Bound shemale slave anal fucked and punished
36 days ago
5:07

KeekAss

Bound shemale slave anal fucked and punished

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Mistress Savannah Hannah punishment
8 years ago
8:25

aShemaleTube

Mistress Savannah Hannah punishment

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Pornstars: savannah

Bald Guy Getting Spit On His Anus
11 years ago
3:05

FlyFlv

Bald Guy Getting Spit On His Anus

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Rude TS mistress punished guy
11 years ago
6:02

aShemaleTube

Rude TS mistress punished guy

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Sexy Milf gives horny big cock TGirl ass and cock punishment
7 years ago
6:37

xHamster

Sexy Milf gives horny big cock TGirl ass and cock punishment

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Features of Public Sex 45+ Sweet mature whore AimeePapadise!
2 years ago
28:10

TrannyOne

Features of Public Sex 45+ Sweet mature whore AimeePapadise!

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Mistress Kara is a hot Milf Librarian who will Punish misbehavers
8 years ago
4:00

TubeDupe

Mistress Kara is a hot Milf Librarian who will Punish misbehavers

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Beautiful stud Junior invites a buxom black tranny to punish his ass
7 years ago
10:00

DrTuber

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

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Shemales Punish Their Little Man Slut
10 years ago
3:00

FlyFlv

Shemales Punish Their Little Man Slut

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Dark Hair Shemale Whipping A Black Guy Before Fucking His Mouth
11 years ago
2:58

FlyFlv

Dark Hair Shemale Whipping A Black Guy Before Fucking His Mouth

Tags: ass, bdsm, black, boots, dark hair, domination, fetish, high heels, interracial, whip

I couldn't resist this beautiful ass, so I punished him with my BBC !
3 days ago
2:08

aShemaleTube

I couldn't resist this beautiful ass, so I punished him with my BBC !

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The Shemale Gladly Punish The Sexy Brunette
11 years ago
3:58

FlyFlv

The Shemale Gladly Punish The Sexy Brunette

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Pornstars: casey cumz, venus lux

Hot TS Anal Punishment
9 years ago
5:16

aShemaleTube

Hot TS Anal Punishment

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Pornstars: venus lux

English femdoms punish submissive outdoors
8 years ago
6:00

TnaFlix

English femdoms punish submissive outdoors

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Bad Shemale Punished Anally
12 years ago
25:38

aShemaleTube

Bad Shemale Punished Anally

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Tranny soccer team punishing male
11 years ago
5:00

aShemaleTube

Tranny soccer team punishing male

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All For You A Pleasure-Filled POV Punishment!
8 years ago
4:00

TubeDupe

All For You A Pleasure-Filled POV Punishment!

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Dominant Shemales Wants Their Whole Body To Be Licked
11 years ago
3:01

FlyFlv

Dominant Shemales Wants Their Whole Body To Be Licked

Tags: 4some, asslick, bdsm, big ass, blonde, bondage, brunette, fetish, humiliation, punishment

Beautiful blonde tranny Mel Vogue has a black bull punishing her ass
7 years ago
10:00

DrTuber

Beautiful blonde tranny Mel Vogue has a black bull punishing her ass

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Domme shemale cop Sasha Strokes fucks thief for punishment
8 years ago
5:26

aShemaleTube

Domme shemale cop Sasha Strokes fucks thief for punishment

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Headmaster punishes and fucks bound shemale student
32 days ago
5:05

aShemaleTube

Headmaster punishes and fucks bound shemale student

Tags: anal, bound, domination, fetish, hd, punishment, student, teen (18+)

Nasty shemale cop Danika Dreamz punishes and fucks a bad guy
11 years ago
5:06

aShemaleTube

Nasty shemale cop Danika Dreamz punishes and fucks a bad guy

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Three Transsexuals Dominate Their Slave
9 years ago
3:05

FlyFlv

Three Transsexuals Dominate Their Slave

Tags: anal, brunette, domination, from behind, gangbang, milf, outdoor, slave, tranny, transsexual

Rough shemales punishing a guy
12 years ago
5:30

aShemaleTube

Rough shemales punishing a guy

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Horny guy punished by trannies outdoor
11 years ago
7:03

aShemaleTube

Horny guy punished by trannies outdoor

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Anal punishment with big dick
15 days ago
4:08

XXXDan

Anal punishment with big dick

Tags: amateur, anal, big ass, big cock, dildo, fishnet, huge dildo, lingerie, masturbation, pov

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

TrannyOne

Tranny Nun Punishes a Dirty Sinner!

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

ShemaleZ

Sexy Trans Student Andrea Will Be Punished

Tags: big cock, brunette, cumshot, hd, latina, punishment, stockings, student, teen (18+), transsexual

Mean tranny babe punishing her slave
4 months ago
5:36

aShemaleTube

Mean tranny babe punishing her slave

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The Punishment
2 years ago
2:33

TrannyOne

The Punishment

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BDSM with two matures crossdressers and an old man
2 years ago
11:13

TrannyOne

BDSM with two matures crossdressers and an old man

Tags: amateur, bdsm, crossdressing, domination, grandpa, hd, homevideo, mature, old, old farts

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

TrannyOne

Blonde fucked in the ass in public

Tags: anal, anus, ass, assfucking, bdsm, big cock, big tits, bizarre, blonde, bondage

Pornstars: lea lexus, princess donna

Flogging Session on the Spanking Bench!
2 years ago
35:35

TrannyOne

Flogging Session on the Spanking Bench!

Tags: amateur, bdsm, domination, femdom, mature, mistress, punishment, spanking

Venus punishes a blonde, fucks her in the ass
9 years ago
5:03

aShemaleTube

Venus punishes a blonde, fucks her in the ass

Tags: ass, blonde, pornstar, punishment

Pornstars: venus lux

Tbabe punished by two guys
11 years ago
17:02

aShemaleTube

Tbabe punished by two guys

Tags: punishment

Blonde shemale is punished and anal fucked
46 days ago
5:08

KeekAss

Blonde shemale is punished and anal fucked

Tags: anal, barebacking, bdsm, blonde, bondage, domination, fetish, handjob, hardcore, hd

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

TrannyOne

TBabe Jenna Tales punish Chads butthole

Tags: anal, ass, big cock, big tits, blonde, blowjob, cumshot, domination, hd, tranny

Slutty tranny Rachel loves PVC nylons and spanking Milf's tight ass
2 years ago
9:01

TrannyOne

Slutty tranny Rachel loves PVC nylons and spanking Milf's tight ass

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Pornstars: rachel love

Ebony TS Adrielly Bronze Punishes Handyman for Waking Her Up
48 days ago
8:00

XXXDan

Ebony TS Adrielly Bronze Punishes Handyman for Waking Her Up

Tags: anal, big cock, black, ebony, hardcore, pornstar, punishment, sucking, teen (18+), transsexual

Pornstars: bronze

Fucked and Punished by a Tran
11 years ago
6:38

aShemaleTube

Fucked and Punished by a Tran

Tags: punishment

TS Slut Punishing A Guy Asshole
13 years ago
5:02

aShemaleTube

TS Slut Punishing A Guy Asshole

Tags: ass, punishment, slut, transsexual

Shemale police officers punish a man
13 years ago
6:36

aShemaleTube

Shemale police officers punish a man

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Guy punished by shemale cops
12 years ago
5:30

aShemaleTube

Guy punished by shemale cops

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TS Jasmine Jewels punishes and rams Tgirl Ashley George
9 years ago
5:10

aShemaleTube

TS Jasmine Jewels punishes and rams Tgirl Ashley George

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Highly Rock-Hard Penalty For She-Male Superslut Hefty Clyster and Electro shock
2 years ago
6:02

KeekAss

Highly Rock-Hard Penalty For She-Male Superslut Hefty Clyster and Electro shock

Tags: amateur, anal, bdsm, big ass, blonde, bondage, crossdressing, fetish, lingerie, milf

Italian Tranny Punishes Wardrobe Attendant Feat Trans) Tommy Bravo - Trans N Shemale - Anna Hickiman And Anna Hickhiman
9 months ago
16:06

ShemaleZ

Italian Tranny Punishes Wardrobe Attendant Feat Trans) Tommy Bravo - Trans N Shemale - Anna Hickiman And Anna Hickhiman

Tags: big ass, big cock, brunette, italian, lingerie, pov, punishment, stockings, tranny, transsexual

Trucker punishes a submissive sissy
1 year ago
5:59

aShemaleTube

Trucker punishes a submissive sissy

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Group punishment Galactic Delight
3 months ago
8:00

IcePorn

Group punishment Galactic Delight

Tags: group sex, hd, pov, punishment, teen (18+)

I am a naughty bitch that needs to be punished severely
9 months ago
6:39

xHamster

I am a naughty bitch that needs to be punished severely

Tags: amateur, american, bbw, bdsm, beauty, bitch, crossdressing, domination, fetish, hd

frenchbaguettes-yaya-the-punisher
6 months ago
19:41

PornHub

frenchbaguettes-yaya-the-punisher

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Blond trap and her bf punishing each other dirtyholes
2 years ago
8:26

aShemaleTube

Blond trap and her bf punishing each other dirtyholes

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Big ass shemale punisher gets sucked before fucking a tied up dude
36 days ago
6:37

aShemaleTube

Big ass shemale punisher gets sucked before fucking a tied up dude

Tags: 3some, anal, big ass, big cock, big tits, blowjob, cumshot, domination, fetish, gangbang

Mistress Samantha punishes her tgirl slave Marina with a good spanking and teases her
55 days ago
14:09

XXXDan

Mistress Samantha punishes her tgirl slave Marina with a good spanking and teases her

Tags: amateur, bdsm, blowjob, couple, crossdressing, dutch, high heels, lingerie, masturbation, mature

Curvy tranny punishes a guy in front of his friend
7 months ago
4:53

JizzBunker

Curvy tranny punishes a guy in front of his friend

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Tranny Punishing A Dude On Their Dinner Table
1 year ago
5:00

ShemaleZ

Tranny Punishing A Dude On Their Dinner Table

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Man Made into Woman by Roommate as Punishment
5 months ago
1:21

xHamster

Man Made into Woman by Roommate as Punishment

Tags: amateur, american, bdsm, beauty, big cock, crossdressing, cum, domination, feminization, fetish

Sissy Maid Icy Hot Wooden Pony Punishment 2
2 months ago
23:29

XXXDan

Sissy Maid Icy Hot Wooden Pony Punishment 2

Tags: amateur, bdsm, beauty, bondage, boots, crossdressing, dildo, fetish, gagging, latex

Sexy tranny spreads her cute little feet for some anal punishment
1 year ago
9:43

aShemaleTube

Sexy tranny spreads her cute little feet for some anal punishment

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A slim girl getting punished by her old master in a dungeon
10 days ago
57:49

xHamster

A slim girl getting punished by her old master in a dungeon

Tags: amateur, american, bdsm, bondage, domination, dungeon, extreme, fantasy, fetish, fisting

Thai Lady And Jordan Pryce - Submissive Ladyboy Mouth And Ass Punished
4 months ago
6:25

ShemaleZ

Thai Lady And Jordan Pryce - Submissive Ladyboy Mouth And Ass Punished

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

KeekAss

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

Tags: amateur, anal, ass, big ass, crazy, crossdressing, dildo, dirty, fetish, fucking machine

Natasha Rotten Steals Christmas Toy And Gets Santas Punishment 8 Min
1 year ago
7:27

ShemaleZ

Natasha Rotten Steals Christmas Toy And Gets Santas Punishment 8 Min

Tags: big ass, big cock, brunette, cumshot, hd, latina, pov, punishment, small tits, solo

You've Been a Bad Boy Mommy Wants to Punish You
27 days ago
1:17

aShemaleTube

You've Been a Bad Boy Mommy Wants to Punish You

Tags: big cock, boy, crossdressing, domination, femboy, hd, mom, pov, punishment, small tits

Italian Tranny Punishes Wardrobe Attendant With Anna Hickiman
7 months ago
16:06

ShemaleZ

Italian Tranny Punishes Wardrobe Attendant With Anna Hickiman

Tags: big tits, brunette, hd, italian, ladyboy, punishment, rimjob, stockings, tranny

PUNISHMENT WITHOUT RESISTANCE
12 days ago
23:21

JizzBunker

PUNISHMENT WITHOUT RESISTANCE

Tags: amateur, anal, babe, big ass, big cock, big tits, blonde, blowjob, brunette, cowgirl

No Se, Cl O And Saryu Usui - 298 Pork Meat Toilet Punishment Of Being Trans
2 months ago
43:48

ShemaleZ

No Se, Cl O And Saryu Usui - 298 Pork Meat Toilet Punishment Of Being Trans

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He Punishes That Tight Shemale Ass From Behind
2 years ago
6:08

ShemaleZ

He Punishes That Tight Shemale Ass From Behind

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Sissy Maid Self Bondage Electro Punishment
3 months ago
36:35

XXXDan

Sissy Maid Self Bondage Electro Punishment

Tags: amateur, anal, bdsm, bondage, crossdressing, dildo, gagging, latex, lingerie, maid

Tv Goddess Foxxy Punishes Loser Boyfriend
2 years ago
10:32

TrannyOne

Tv Goddess Foxxy Punishes Loser Boyfriend

Tags: anal, anus, ass, barebacking, bdsm, boyfriend, crossdressing, domination, goddess, hd

Punished slut
7 months ago
3:53

aShemaleTube

Punished slut

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White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis
15 days ago
6:47

XXXDan

White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis

Tags: anal, ass, big ass, big clit, black, dildo, feminization, lingerie, punishment, sissy

Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.
7 months ago
18:52

xHamster

Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.

Tags: amateur, ass, bdsm, beauty, couple, crossdressing, curvy, cute, domination, hd

Amazing blond sissy punished by her construction worker
3 months ago
7:00

aShemaleTube

Amazing blond sissy punished by her construction worker

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Good little CD Luci May sucking Santas big cock for a sack full of his christmas cum
2 years ago
8:02

TrannyOne

Good little CD Luci May sucking Santas big cock for a sack full of his christmas cum

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Spank Bank
2 years ago
6:08

TrannyOne

Spank Bank

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Punishing her bf's ass with a hot painal session
2 months ago
9:07

aShemaleTube

Punishing her bf's ass with a hot painal session

Tags: amateur, anal, ass, assfucking, hardcore, homevideo, punishment, tranny

Shiri Allwood - Femboy Brat Jasper Gets Punished
1 year ago
24:43

KeekAss

Shiri Allwood - Femboy Brat Jasper Gets Punished

Tags: anal, barebacking, beauty, blowjob, cum, cumshot, fantasy, femboy, fleshlight, hd

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

ShemaleZ

A Private Punishment With Natalie Mars

Tags: brunette, pov, punishment, small tits, tattoo, toys

Gorgeous shemale milf punishing her shecock with her fleshlight
8 months ago
7:33

aShemaleTube

Gorgeous shemale milf punishing her shecock with her fleshlight

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Submissive ladyboy mouth and ass punished
5 months ago
6:24

aShemaleTube

Submissive ladyboy mouth and ass punished

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Mistress T punishing sissy with big toys
1 year ago
23:41

TrannyOne

Mistress T punishing sissy with big toys

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Pornstars: mistress t

Short haired woman enjoys getting her ass spanked by her lord
14 days ago
57:58

xHamster

Short haired woman enjoys getting her ass spanked by her lord

Tags: amateur, american, ass, bdsm, bondage, domination, extreme, fetish, orgasm, punishment

Tranny Punishing A Dude In Front Of
10 months ago
4:30

ShemaleZ

Tranny Punishing A Dude In Front Of

Tags: amateur, bdsm, big tits, cumshot, domination, fetish, punishment, tranny