Punish Videos (59,396)

plump older caning

plump older caning

MatureTubeHere 5 years ago

Sophia Loreen Private Show

HD 2:00 / 12:23

Sophia Loreen Private Show

Camster 1 month ago

Naughty Italian MILF Anna Hickiman dominates & punishes attendant on couch

Naughty Italian MILF Anna Hickiman dominates & punishes attendant on couch

TrannyMovs 10 months ago

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

Fetishpapa 1 year ago

Instruction from the trainer No 12 Exposure walk in the sports park

Instruction from the trainer No 12 Exposure walk in the sports park

XHamster 8 months ago

Worship Khloe: Submissive Helena Locke Devotes Herself to Mistress Kay

Worship Khloe: Submissive Helena Locke Devotes Herself to Mistress Kay

XHamster 1 month ago

Colombian Boys Private Show

48% HD 2:00 / 7:59

Colombian Boys Private Show

Flirt4Free 2 years ago

Gorgeous TS babe doggystyled by partner

Gorgeous TS babe doggystyled by partner

Some.Porn 11 months ago

Big Girl Cock: Aspen Brooks Punishes Kip Johnson on Their Anniversary

Big Girl Cock: Aspen Brooks Punishes Kip Johnson on Their Anniversary

XHamster 9 months ago

A Disgrace to Our Town Part 1

56% 1:01 / 21:04

A Disgrace to Our Town Part 1

FapHouse 1 year ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Camster 1 week ago

Zara Clark Private Show

65% 4K 2:00 / 6:41

Zara Clark Private Show

Flirt4Free 2 months ago

Booty Calls Ep 1: Shiri Allwood Fucks Nikki Darling's Whore Holes!

Booty Calls Ep 1: Shiri Allwood Fucks Nikki Darling's Whore Holes!

XHamster 9 months ago

Roommate Issues

Roommate Issues

Some.Porn 2 years ago

You Won't Cum if You're Not GAY

66% 4K 0:30 / 15:16

You Won't Cum if You're Not GAY

Clips4sale 5 months ago

Shemale Slut Carla Fucking Her Ass with a Big Dildo

Shemale Slut Carla Fucking Her Ass with a Big Dildo

XHamster 1 month ago

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

Sitting on my Slave&#039_s Face and Farting

Premium HD 11:45

Sitting on my Slave&#039_s Face and Farting

XNXXGold 1 year ago

Shemale Mafia Punish Poor Girl

Shemale Mafia Punish Poor Girl

Wankoz 4 days ago

Sophia Loreen Private Show

HD 2:00 / 18:41

Sophia Loreen Private Show

Flirt4Free 4 weeks ago

Cute Big Tits Trans Girl in Caulifla Cosplay Pumping and Punishing her Tits with Vacuum Milking Machine and Lactation

Cute Big Tits Trans Girl in Caulifla Cosplay Pumping and Punishing her Tits with Vacuum Milking Machine and Lactation

XHamster 1 month ago

Step-mommy Teaches You About Condoms JOI

Step-mommy Teaches You About Condoms JOI

XHamster 1 year ago

West Wing Porn - the Dirtiest Business of All - Politics

West Wing Porn - the Dirtiest Business of All - Politics

Amateur8 2 weeks ago

TS Yoga Instructor Dominates Foot-Sniffer

TS Yoga Instructor Dominates Foot-Sniffer

AShemaleTube 10 years ago

Alice Kizar Private Show

55% 4K 2:00 / 7:37

Alice Kizar Private Show

Camster 2 weeks ago

Black and beautiful professor teaches you how to please her

Black and beautiful professor teaches you how to please her

XHamster 4 months ago

TSlut steel bound for FemDom orgasms (MP4 HD 6000kbps)

HD 0:11 / 10:35

TSlut steel bound for FemDom orgasms (MP4 HD 6000kbps)

Clips4sale 1 year ago

Sophia Loreen Party on May 13, 2026 - Part 3

55% HD 2:00 / 34:53

Sophia Loreen Party on May 13, 2026 - Part 3

Flirt4Free 2 months ago

Whores Get Banged: Recent Cutie Ella Hollywood Screwed by Sebastian Keys

Whores Get Banged: Recent Cutie Ella Hollywood Screwed by Sebastian Keys

ShemaleSin 2 months ago

Dominic Pacifico Punishes Disobedient TS Lianna Lawson Rough BDSM Latex Bondage Spanking Suspension

Dominic Pacifico Punishes Disobedient TS Lianna Lawson Rough BDSM Latex Bondage Spanking Suspension

Sheshaft 8 months ago

Caught in the act

Caught in the act

Eporner 3 years ago

Stepdad pounds his stepdaughter's tight pussy while wearing braces - Scarlet Skies

Stepdad pounds his stepdaughter's tight pussy while wearing braces - Scarlet Skies

Some.Porn 2 years ago

Natasha Milk Private Show

Natasha Milk Private Show

Camster 1 week ago

Sophie Fantasy Private Show

61% HD 2:00 / 31:39

Sophie Fantasy Private Show

Flirt4Free 3 weeks ago

Sophia Loreen Private Show

54% HD 2:00 / 13:02

Sophia Loreen Private Show

Flirt4Free 2 months ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Flirt4Free 1 day ago

Ponytailed Ladyboy Slave For Cock

Ponytailed Ladyboy Slave For Cock

Eporner 3 years ago

TS Goddess POV Punishment

TS Goddess POV Punishment

Sheshaft 3 days ago

Pregnant Ayla Aysel Spanks and Wedgies Her Pathetic Slave (STANDARD WMV)

63% 0:11 / 12:23

Pregnant Ayla Aysel Spanks and Wedgies Her Pathetic Slave (STANDARD WMV)

Clips4sale 4 years ago

TS VIVIANA ROSE GETS PUNISHED #1 ❤️ she's so fucking sexy

TS VIVIANA ROSE GETS PUNISHED #1 ❤️ she's so fucking sexy

AShemaleTube 6 months ago

Bitch caught watching tranny porn and masturbating alone, she must be punished now

Bitch caught watching tranny porn and masturbating alone, she must be punished now

XHamster 6 months ago

Tranny Addiction 4

52% HD 0:30 / 2:02:00

Tranny Addiction 4

AEBN 8 years ago

Bitches Get Banged: Recent Gal Ella Hollywood Drilled by Sebastian Keys

Bitches Get Banged: Recent Gal Ella Hollywood Drilled by Sebastian Keys

ShemaleSin 1 month ago

Strap On GF and CEI Punishment

57% HD 0:11 / 11:59

Strap On GF and CEI Punishment

Clips4sale 4 years ago

Hot shemale punisher in black fishnets gives a massive

Hot shemale punisher in black fishnets gives a massive

XHamster 2 years ago

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

XHamster 5 months ago

femout - jill pill portland tranny xmas hardcore sex

femout - jill pill portland tranny xmas hardcore sex

TransDoe 2 years ago

Poor guy gets humiliated and dominated by the beastly TS babe

Poor guy gets humiliated and dominated by the beastly TS babe

Tranny.one 4 years ago

BDSM and fist for crossdresser

BDSM and fist for crossdresser

Fetishpapa 8 months ago

Aub Kat - Wife Punishes You

Aub Kat - Wife Punishes You

Eporner 1 year ago

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 1

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 1

XHamster 1 month ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 4 months ago

Hard Cash Payback!

Hard Cash Payback!

XHamster 1 year ago

Sexy strip, twerk naked, playing with my nipples and with my pussy, lets play with my dildo and make me wet!!

Sexy strip, twerk naked, playing with my nipples and with my pussy, lets play with my dildo and make me wet!!

Flirt4Free 4 years ago

strict mistress with huge strapon and big cock catch and punish her robber

strict mistress with huge strapon and big cock catch and punish her robber

AShemaleTube 1 year ago

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

60% HD 0:39 / 21:15

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

FapHouse 4 weeks ago

Freak of Nature 38 Older SADOMASOCHISM

Freak of Nature 38 Older SADOMASOCHISM

MatureTubeHere 5 years ago

Wearing to cross dress

Wearing to cross dress

XHamster 1 year ago

Elvis & Alfonso & Master Private Show

68% HD 2:00 / 14:58

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Their slaves ass needs a little punishment

Their slaves ass needs a little punishment

XHamster 1 year ago

Axel & David Private Show

59% HD 2:00 / 16:49

Axel & David Private Show

Flirt4Free 3 years ago

A Perfect Punish - Morgan Bailey, Alex Ander And Alexander Gustavo

A Perfect Punish - Morgan Bailey, Alex Ander And Alexander Gustavo

AbTranny 2 years ago

Sophia Loreen Party on Jul 23, 2026 - Part 4

HD 2:00 / 13:47

Sophia Loreen Party on Jul 23, 2026 - Part 4

Camster 1 week ago

Master & Chris & Elvis Rey Private Show

63% HD 2:00 / 10:11

Master & Chris & Elvis Rey Private Show

Flirt4Free 3 years ago

Moroccan whore riding on a prosthesis or a master on her cock with a lock 🤤

Moroccan whore riding on a prosthesis or a master on her cock with a lock 🤤

XHamster 7 months ago

Domina shemale damages spiderman's ass

Domina shemale damages spiderman's ass

Eporner 5 months ago

Ts Jesse Milks John Dry FiveTimes

Ts Jesse Milks John Dry FiveTimes

Analdin 3 months ago

Bound shemale slave anal fucked and punished

Bound shemale slave anal fucked and punished

Eporner 2 years ago

Petite Alt Girl Gets Ragdolled Sweet & Rough by Dominant Tgirl and Takes Her Load

Petite Alt Girl Gets Ragdolled Sweet & Rough by Dominant Tgirl and Takes Her Load

FapHouse 1 month ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

AShemaleTube 10 months ago

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

AShemaleTube 1 year ago

2623 they spit on you and break you

67% HD 0:15 / 9:16

2623 they spit on you and break you

IWantClips 1 month ago

Trans Angel Worships His Trans Weenie Previous to This guy Wrecks Her Booty

Trans Angel Worships His Trans Weenie Previous to This guy Wrecks Her Booty

ShemaleSin 7 months ago

Jenny Wei Gets Punished #3

Jenny Wei Gets Punished #3

AShemaleTube 6 months ago

Jenny Wei is BACK! Gets fucked and facialed by The BBC PUNISHER

Jenny Wei is BACK! Gets fucked and facialed by The BBC PUNISHER

AShemaleTube 4 months ago

Shemale fucks male sub in pink dungeon

Shemale fucks male sub in pink dungeon

GayVids 10 months ago

”Sexy Stepmom Tranny punishing naughty hubby”

”Sexy Stepmom Tranny punishing naughty hubby”

HQBang 2 years ago

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

HD 0:23 / 41:59

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

AnalVids 2 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 1 week ago

Blonde TS Samara De Macedo Gangbanged

Blonde TS Samara De Macedo Gangbanged

Sheshaft 4 years ago

Camila & Samael Private Show

77% HD 2:00 / 22:30

Camila & Samael Private Show

Flirt4Free 1 year ago

Three shemale dominas in high heels spank and fuck their

Three shemale dominas in high heels spank and fuck their

XHamster 2 years ago

Sophia Loreen Private Show

62% HD 2:00 / 8:41

Sophia Loreen Private Show

Flirt4Free 2 months ago

Dare to Get a Little Closer.

Dare to Get a Little Closer.

Flirt4Free 1 week ago

Big Tits Femboy Ben Tennyson Lactating and Pumping her Puffy Nipples with Vacuum Milking Machine

Big Tits Femboy Ben Tennyson Lactating and Pumping her Puffy Nipples with Vacuum Milking Machine

XHamster 1 month ago

Two friends humiliate and punish a sissy

Two friends humiliate and punish a sissy

AShemaleTube 3 years ago

Passionate Preacher

Passionate Preacher

Some.Porn 6 months ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

XHamster 6 months ago

Towheaded Whipped

Towheaded Whipped

TrannyGem 6 years ago

Paris & Oliver Private Show

HD 2:00 / 29:21

Paris & Oliver Private Show

Camster 3 years ago

Mistress T punishing sissy with big toys

Mistress T punishing sissy with big toys

Tranny.one 3 years ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Camster 1 year ago

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

XHamster 5 months ago

Sophia Loreen Private Show

61% HD 2:00 / 13:06

Sophia Loreen Private Show

Camster 1 month ago

SHEMALE PUNISHERS - Shemale Domme Trio In The Jungle

SHEMALE PUNISHERS - Shemale Domme Trio In The Jungle

XHamster 1 year ago

La Cherry Spice, Dorian

La Cherry Spice, Dorian

XHamster 1 year ago

COCK IN A FROCK #6

74% 4K 0:30 / 13:00

COCK IN A FROCK #6

Clips4sale 2 years ago

Trans Dominatrix Girl Punishes This Guy By Destroying His Ass

Trans Dominatrix Girl Punishes This Guy By Destroying His Ass

BeMyHole 2 years ago

Sophia Loreen Private Show

HD 2:00 / 23:59

Sophia Loreen Private Show

Camster 5 days ago

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

XHamster 2 years ago

Master & Christian Mckenzie & Christian Rey Private Show

58% HD 2:00 / 39:40

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Sub Tgirl Fucked Rough by Master!

Sub Tgirl Fucked Rough by Master!

Eporner 5 years ago

Christian & Nicco & Elvis Private Show

51% HD 2:00 / 4:40

Christian & Nicco & Elvis Private Show

Flirt4Free 2 years ago

Shemale Mafia Punish Poor Girl

Shemale Mafia Punish Poor Girl

Eporner 4 days ago

MILF Librarian Punishes TS Delinquent

MILF Librarian Punishes TS Delinquent

AShemaleTube 11 years ago

Crossdresser Tickled and Vibed in Slut Heels

75% HD 1:01 / 8:37

Crossdresser Tickled and Vibed in Slut Heels

FapHouse 1 year ago

Straight guy together with freind of him who has boobs punishes whity

Straight guy together with freind of him who has boobs punishes whity

Tranny.one 9 years ago

Sophia Loreen Private Show

HD 2:00 / 23:59

Sophia Loreen Private Show

Flirt4Free 5 days ago

Lanna & Nefertiti Private Show

64% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

Painfully decorated and stuffed

Painfully decorated and stuffed

XHamster 2 years ago

lizzy laynez punished lizzy laines

lizzy laynez punished lizzy laines

PornOne 2 years ago

The Boss! TS Domination

The Boss! TS Domination

XHamster 1 month ago

Lesbian Seeks TGirl

63% HD 0:30 / 1:46:00

Lesbian Seeks TGirl

AEBN 6 years ago

Italian tranny Anna Hickiman punishes wardrobe attendant

66% HD 1:01 / 46:46

Italian tranny Anna Hickiman punishes wardrobe attendant

FapHouse 3 years ago

Out Foxed, Flogged, and Fucked

58% HD 0:39 / 34:05

Out Foxed, Flogged, and Fucked

FapHouse 2 months ago

Sophia Loreen Private Show

71% HD 2:00 / 16:24

Sophia Loreen Private Show

Flirt4Free 1 year ago

Trans Maid Punished by Smoking Beautiful Asian Goddess Cynthia

HD 0:10 / 11:59

Trans Maid Punished by Smoking Beautiful Asian Goddess Cynthia

LoyalFans 4 days ago

Sissy Cocksucker gets Slapped on her Big Puffy Lactating Nipples

Sissy Cocksucker gets Slapped on her Big Puffy Lactating Nipples

XHamster 9 months ago

Sophia Loreen Private Show - Part 2

HD 2:00 / 40:15

Sophia Loreen Private Show - Part 2

Flirt4Free 1 week ago

Desire Sweet Private Show

HD 2:00 / 13:54

Desire Sweet Private Show

Camster 2 weeks ago

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