Punishment Videos (59,729)

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

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

AShemaleTube 2 years ago

Horny babe smashed in IR gangbang

Horny babe smashed in IR gangbang

Some.Porn 1 year ago

Master & Christian & Nicco Private Show

54% HD 2:00 / 9:51

Master & Christian & Nicco Private Show

Flirt4Free 2 years ago

Broke out of Chastity and Punished - TS Gray Perrier Dominated by SlayerXXX

Premium HD 41:59

Broke out of Chastity and Punished - TS Gray Perrier Dominated by SlayerXXX

Sheer 2 months ago

”Shemale housewife wait all day for her hubby's cock”

”Shemale housewife wait all day for her hubby's cock”

LesbianBliss 6 months ago

Master & Christian & Patric Private Show

63% HD 2:00 / 12:10

Master & Christian & Patric Private Show

Flirt4Free 3 years ago

”Stalking guy talks stepsis into having some nasty sex with him”

”Stalking guy talks stepsis into having some nasty sex with him”

TransHero 7 months 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 1 week ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Flirt4Free 6 days ago

Sophie Fantasy Private Show - Part 2

Sophie Fantasy Private Show - Part 2

Flirt4Free 4 weeks ago

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

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

Tranny.one 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 2 weeks ago

double fisting for alice maze, punishment and humiliation

HD 0:49 / 31:56

double fisting for alice maze, punishment and humiliation

AnalVids 1 year ago

Sophia Loreen Private Show

66% HD 2:00 / 17:12

Sophia Loreen Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

65% HD 2:00 / 18:40

Sophia Loreen Private Show

Camster 3 weeks ago

Sophia Loreen Private Show

HD 2:00 / 15:34

Sophia Loreen Private Show

Flirt4Free 2 months ago

”Babe in rope bondage muff toyed”

”Babe in rope bondage muff toyed”

TransHero 7 months ago

TS Jesse Punishes a Cis and TS Man!

TS Jesse Punishes a Cis and TS Man!

XXXShemalePorn 8 years ago

Hard Pegging Male In The Kitchen

Hard Pegging Male In The Kitchen

XNXXGold 1 year ago

Natalia La Potra and Goody Make Love - BlackTGirlsHardcore

Natalia La Potra and Goody Make Love - BlackTGirlsHardcore

AbTranny 6 years ago

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 4

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 4

LoyalFans 2 years ago

Sophia Loreen Private Show

61% HD 2:00 / 12:52

Sophia Loreen Private Show

Flirt4Free 1 year ago

Hank Wants Me in My Leather Gear to Make Him Smell It

Hank Wants Me in My Leather Gear to Make Him Smell It

Flirt4Free 8 months ago

Horny lez gets anal fisted by cougar

Horny lez gets anal fisted by cougar

Some.Porn 1 year ago

Katy Ling Private Show

HD 2:00 / 13:59

Katy Ling Private Show

Flirt4Free 1 day ago

I felt like I was the only one in the house Clip 1

I felt like I was the only one in the house Clip 1

XHamster 2 months ago

DOMINATE'S GRIP CHOKES CONTROL IN SHADOWED CHAINS

DOMINATE'S GRIP CHOKES CONTROL IN SHADOWED CHAINS

BoyFriendTV 4 months ago

Naughty Teen Ladyboy Anal Punishment

Naughty Teen Ladyboy Anal Punishment

Eporner 4 months ago

Sophia Loreen Party on Jul 30, 2026 - Part 3

57% 4K 2:00 / 42:41

Sophia Loreen Party on Jul 30, 2026 - Part 3

Camster 6 days ago

TS Jesse Punishes A Cis and Trans Man - See Full Video at ShemaleDream.Tube

TS Jesse Punishes A Cis and Trans Man - See Full Video at ShemaleDream.Tube

Eporner 8 years ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 1 year ago

Ts Coming For Cheating Bf And Punishes Him With Shecock In The Ass - Jessica Fox

Ts Coming For Cheating Bf And Punishes Him With Shecock In The Ass - Jessica Fox

AbTranny 6 months ago

”Samantha Bentley fucking the priest”

”Samantha Bentley fucking the priest”

ThePornstar 1 year ago

Choking and caning kitsy

Choking and caning kitsy

XXXShemalePorn 2 years ago

MILF librarian Mistress Kara punishes misbehaved TS Stefani Special

MILF librarian Mistress Kara punishes misbehaved TS Stefani Special

Fetishpapa 1 year ago

Part 2:- Lanist Bear takes Maid Jayne in the dungeon for her punishments.

Part 2:- Lanist Bear takes Maid Jayne in the dungeon for her punishments.

XHamster 1 month ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 5 months ago

Horny Sandy Playing with Two Dildos

67% HD 2:00 / 7:01

Horny Sandy Playing with Two Dildos

Flirt4Free 10 years ago

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Xshemale 8 months ago

Violetta R Private Show

65% HD 2:00 / 12:17

Violetta R Private Show

Flirt4Free 3 years ago

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 2

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 2

XHamster 1 month ago

with a dildo and reflected in the mirror I will shake my pussy... #PLATFORM/DILDO/RIDER#

with a dildo and reflected in the mirror I will shake my pussy... #PLATFORM/DILDO/RIDER#

Camster 2 years ago

Guess Who Got Punished This Time

Guess Who Got Punished This Time

XNXXGold 1 year ago

crossdresser punishment

crossdresser punishment

AShemaleTube 4 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 7 months ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

51% HD 2:00 / 56:20

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 4 months ago

Educating A Bitchboy: Episode 4 "Last Chance"

Premium 46% HD 1:02:19

Educating A Bitchboy: Episode 4 "Last Chance"

Kink 15 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Two friends humiliate and punish a sissy

Two friends humiliate and punish a sissy

AShemaleTube 3 years ago

We Caning Competitions

We Caning Competitions

Some.Porn 1 year ago

Tall tattooed shemale punishes sub bf

Tall tattooed shemale punishes sub bf

TrannyGem 1 month ago

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

AbTranny 4 years ago

Latex Domination and Sissy Training

Latex Domination and Sissy Training

TransTube.tv 1 month ago

Naughty t-girl Nun punishing man

Naughty t-girl Nun punishing man

Analdin 1 month ago

Trans Stepsister Femdom

Trans Stepsister Femdom

XHamster 1 year ago

Fucking Behind Back

Fucking Behind Back

Some.Porn 1 year ago

Matt & Elvis & Aron Private Show

HD 2:00 / 13:25

Matt & Elvis & Aron Private Show

Flirt4Free 3 years ago

Sandy Lee Private Show

61% HD 2:00 / 11:59

Sandy Lee Private Show

Camster 11 years ago

Sissy Princess getting punished an Owned by Madam Kitty Kaos

Sissy Princess getting punished an Owned by Madam Kitty Kaos

AShemaleTube 2 years ago

Sandy Lee Private Show

HD 2:00 / 10:05

Sandy Lee Private Show

Camster 10 years ago

Hot TS mistress punished guy

Hot TS mistress punished guy

AShemaleTube 13 years ago

Allicia Nogueira spanks and fucks her slave until messy

Allicia Nogueira spanks and fucks her slave until messy

XHamster 2 years ago

Young Trans Girl Milks her Big Natural Tits after being Punished

Young Trans Girl Milks her Big Natural Tits after being Punished

XHamster 10 months ago

Sophia Loreen Private Show

HD 2:00 / 14:56

Sophia Loreen Private Show

Flirt4Free 3 years ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Sheer 1 year ago

Jenny Wei makes her porn return i'm getting punished by us truly. Full 18 min video out!

Jenny Wei makes her porn return i'm getting punished by us truly. Full 18 min video out!

AShemaleTube 1 year ago

Tranny Secretary Gets Wedgied and Spanked

Tranny Secretary Gets Wedgied and Spanked

XHamster 8 months ago

Nyobi Khan and Rico

HD 0:39 / 59:52

Nyobi Khan and Rico

FapHouse 1 year ago

crossdresser bitch

crossdresser bitch

Fetishpapa 3 years ago

Haycka Fucks the Gardener and Gets Fucked in the Ass by Her Boyfriend

Haycka Fucks the Gardener and Gets Fucked in the Ass by Her Boyfriend

XHamster 1 year ago

Sophia Loreen Party on Jul 18, 2026 - Part 3

HD 2:00 / 17:13

Sophia Loreen Party on Jul 18, 2026 - Part 3

Camster 2 weeks ago

European White Girl with Big Dildos

HD 2:00 / 14:51

European White Girl with Big Dildos

Camster 10 years ago

Spank Crossdresser slave

Spank Crossdresser slave

BoyFriendTV 6 years ago

Master & Ithan Private Show

62% HD 2:00 / 20:20

Master & Ithan Private Show

Flirt4Free 1 year ago

Cute Ass Femboy with Dva Cosplay Wedgie and Anal Fucked

Cute Ass Femboy with Dva Cosplay Wedgie and Anal Fucked

XHamster 7 months ago

”Brats Get Punished”

”Brats Get Punished”

ThePornstar 5 months ago

Luccas & Archie & Jose Private Show

57% HD 2:00 / 52:50

Luccas & Archie & Jose Private Show

Flirt4Free 6 months ago

Sandy Lee Private Show

65% HD 2:00 / 23:26

Sandy Lee Private Show

Flirt4Free 10 years ago

Booty TS Graziella Toledo punishes helpless man with her mighty dick

Booty TS Graziella Toledo punishes helpless man with her mighty dick

Wankoz 8 months ago

Leather T-girl Suspension and Pegging

Leather T-girl Suspension and Pegging

Analdin 3 months ago

BDSM and fist for crossdresser

BDSM and fist for crossdresser

Fetishpapa 8 months ago

Giant Femboy Goddess Tenderizes and Consumes You

Giant Femboy Goddess Tenderizes and Consumes You

FapHouse 3 months ago

Crossdresser boyfriend is fucked by dominatrix with strapon

Crossdresser boyfriend is fucked by dominatrix with strapon

XGroovy 3 years ago

”Big Boobed tgirl Ember Fiera slaps & fucks Andrew Connor's booty”

”Big Boobed tgirl Ember Fiera slaps & fucks Andrew Connor's booty”

HQBang 2 years ago

Stiv Soul Private Show

HD 2:00 / 17:22

Stiv Soul Private Show

Flirt4Free 1 month ago

BDSM master puts stick in sub's gaping pussy after fingering

BDSM master puts stick in sub's gaping pussy after fingering

Some.Porn 1 year ago

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

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

XHamster 2 years ago

Hard and Consensual Domination

66% HD 2:00 / 20:55

Hard and Consensual Domination

Flirt4Free 2 years ago

Busty latina teen suspect punish fucked by a LP officer

Busty latina teen suspect punish fucked by a LP officer

ALOTPorn 4 years ago

Muscular submissive slave man wants to be tied and whipped

Muscular submissive slave man wants to be tied and whipped

XHamster 3 years ago

Dominant Shemale Mistress Camila Smith Punishes Her Sex Slave

Dominant Shemale Mistress Camila Smith Punishes Her Sex Slave

GetTranny 4 years ago

West Wing Porn - the Dirtiest Business of All - Politics

HD 1:01 / 43:37

West Wing Porn - the Dirtiest Business of All - Politics

FapHouse 4 weeks ago

Sexy Mexican Mami Caricia De Angel Gets Punished #3 full video available now

Sexy Mexican Mami Caricia De Angel Gets Punished #3 full video available now

AShemaleTube 3 months ago

Painful scrutiny 1St Part (User Request)

Painful scrutiny 1St Part (User Request)

MatureTubeHere 5 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Dildo, Anal, Ass Gaping

Dildo, Anal, Ass Gaping

Camster 9 years ago

Marian & Richard Private Show

Marian & Richard Private Show

Camster 3 weeks ago

Spanking crossdresser

Spanking crossdresser

BoyFriendTV 1 year ago

Lady Fee Punishes Sissy Dee for Playing with Her Toys

Lady Fee Punishes Sissy Dee for Playing with Her Toys

XHamster 1 month ago

PUNISHED IN PLACE #1 featuring Erin Everheart

Premium HD 21:31

PUNISHED IN PLACE #1 featuring Erin Everheart

XVideosRed 2 years ago

Punishing A Guy Outdoors - Alana Ferreira

Punishing A Guy Outdoors - Alana Ferreira

AbTranny 4 years ago

tranny Punishers harsh Up lad fuck stick Evelin Rangel Bruna Castro

tranny Punishers harsh Up lad fuck stick Evelin Rangel Bruna Castro

TrannyGem 5 years ago

Islam Niram Private Show

HD 2:00 / 23:29

Islam Niram Private Show

Flirt4Free 1 week ago

A shy teen girl gets a hard spanking from her master with a long whip

A shy teen girl gets a hard spanking from her master with a long whip

XHamster 2 years ago

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

UrGayPorn 10 months ago

Ladyboy Many Punished Bareback

Ladyboy Many Punished Bareback

AShemaleTube 10 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Smalltits tgirl beauty gets interviewed

Smalltits tgirl beauty gets interviewed

XHamster 7 years ago

Punished bareback: ladyboy amys experience

Punished bareback: ladyboy amys experience

XXXShemalePorn 1 year ago

Marian & Richard Private Show

58% HD 2:00 / 4:51

Marian & Richard Private Show

Camster 4 weeks ago

Please punish me teacher for being bad

Please punish me teacher for being bad

Fapcat 1 year ago

Pink lingeried black shemale punishes her bf

Pink lingeried black shemale punishes her bf

Eporner 5 months ago

European Model Brutus Bounces His Pecs

European Model Brutus Bounces His Pecs

Flirt4Free 10 years ago

Sandy Lee Private Show

61% HD 2:00 / 7:30

Sandy Lee Private Show

Flirt4Free 11 years ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

62% HD 1:01 / 22:05

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

FapHouse 3 months ago

NAUGHTY VARIETY CAUGHT MASTURBATING

NAUGHTY VARIETY CAUGHT MASTURBATING

XVideosRed 10 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

HD 0:39 / 19:41

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

FapHouse 8 months ago

Maya Spring Private Show

61% 4K 2:00 / 53:11

Maya Spring Private Show

Camster 2 weeks ago

Jade Venus Rules Draven in BDSM Play

Jade Venus Rules Draven in BDSM Play

GayVids 1 month ago

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