Punishment Videos (39,430)

Dutch and TS Teighjiana Boring Date Becomes Rough Sex Club Fucking Anal Blowjobs and Licking

Dutch and TS Teighjiana Boring Date Becomes Rough Sex Club Fucking Anal Blowjobs and Licking

Sheshaft 1 week ago

Toxic male ***: dominated & made to eat trans girl ass

HD 0:39 / 21:11

Toxic male ***: dominated & made to eat trans girl ass

FapHouse 3 years ago

Pimp and prostitute-shemale punished prostitute-rival

Pimp and prostitute-shemale punished prostitute-rival

aShemaleTube 7 years ago

sloppy sluts femdom orgy

68% HD 0:30 / 23:50

sloppy sluts femdom orgy

PornBox 1 year ago

Hercules & Lian & Lance Private Show

50% HD 2:00 / 9:07

Hercules & Lian & Lance Private Show

Flirt4Free 3 years ago

”Lesbian ass fucking toyed in pile driver”

”Lesbian ass fucking toyed in pile driver”

TransHero 4 weeks ago

Treated like a slut and squeezed like a cow

Treated like a slut and squeezed like a cow

xHamster 1 year ago

TS Jayla Marie has fucking power of a machine that will set men straight

TS Jayla Marie has fucking power of a machine that will set men straight

Pornwhite 2 weeks ago

Bound up femboy required to cum! Post Climax Punishment

Bound up femboy required to cum! Post Climax Punishment

ShemaleSin 9 months ago

Anal Threesome at the Office Hardcore

Anal Threesome at the Office Hardcore

xHamster 4 months ago

Strapon & Piss Enema for Diapered Sissy Husband

Strapon & Piss Enema for Diapered Sissy Husband

xHamster 2 years ago

”Dirty hoe ravaged in public garage”

”Dirty hoe ravaged in public garage”

TransHero 4 weeks ago

Big Dick Trans Mommy Cumming and Milking her Tits

Big Dick Trans Mommy Cumming and Milking her Tits

xHamster 1 month ago

Avery Angel gets Punished

Avery Angel gets Punished

aShemaleTube 1 year ago

Avery Angel gets fucked by The BBC PUNISHER! Full 22 min vid available now! SO HOT!

Avery Angel gets fucked by The BBC PUNISHER! Full 22 min vid available now! SO HOT!

aShemaleTube 4 months ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 7 months ago

”Alexander Gustavo loves his horny punishment from Transgender Morgan Bailey”

”Alexander Gustavo loves his horny punishment from Transgender Morgan Bailey”

LesbianBliss 3 days ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

aShemaleTube 10 months ago

Nick & Diego & Liam Private Show

53% HD 2:00 / 1:06:19

Nick & Diego & Liam Private Show

Flirt4Free 3 years 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 8 months ago

Sissyfication 1

58% HD 1:01 / 10:56

Sissyfication 1

FapHouse 8 months ago

Elix & Elias & Paulo Private Show

70% HD 2:00 / 4:57

Elix & Elias & Paulo Private Show

Flirt4Free 3 months ago

Strap-on & chastity punishment for stealing Mistress' clothes 😭🔐 @Saskia_and_Sasha on OF

Strap-on & chastity punishment for stealing Mistress' clothes 😭🔐 @Saskia_and_Sasha on OF

aShemaleTube 1 year ago

”Post Orgasm Punishment”

”Post Orgasm Punishment”

TransHero 2 days ago

Pt 1 Self Punishment BDSM Ballbusting Spanking Clothespin Part 1

HD 0:39 / 14:56

Pt 1 Self Punishment BDSM Ballbusting Spanking Clothespin Part 1

FapHouse 2 weeks ago

The Punishment

50% 4K 2:00 / 20:15

Flirt4Free 3 months ago

You failed the exam, teacher wants to punish you by feminizing and fucking your sissy hole(FEMINIZATION ROLEPLAY - AI GENERATED)

You failed the exam, teacher wants to punish you by feminizing and fucking your sissy hole(FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 9 months ago

Anonymous Cock Wall BJ Facefuck Facial Cumshot for Chastity Tgirl

Anonymous Cock Wall BJ Facefuck Facial Cumshot for Chastity Tgirl

XVideosRed 1 year ago

Redhead TGirl slut handcuffed spanked and whipped in the garden by leather clad master

Redhead TGirl slut handcuffed spanked and whipped in the garden by leather clad master

Tranny.one 4 years ago

Three shemales in black leather outfits spank and fuck a

Three shemales in black leather outfits spank and fuck a

xHamster 8 months 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 8 years ago

”Transgender Paradise gets tightened her butthole by Jayden Marcos”

”Transgender Paradise gets tightened her butthole by Jayden Marcos”

HQBang 2 years ago

Erotic Asian Transsexual Domination With Ballbusting And Facesitting By Ts Venus Lux

45% HD 0:30 / 29:00

Erotic Asian Transsexual Domination With Ballbusting And Facesitting By Ts Venus Lux

AEBN 12 years ago

India new sexx girls happy moment

India new sexx girls happy moment

xHamster 11 months ago

Shemale jade punishes boy friend

Shemale jade punishes boy friend

Fetishpapa 3 years ago

Liam Jacobson Private Show

63% HD 2:00 / 5:47

Liam Jacobson Private Show

Flirt4Free 1 year ago

Crossdresser Tickled and Vibed in Slut Heels

75% HD 1:01 / 8:37

Crossdresser Tickled and Vibed in Slut Heels

FapHouse 8 months ago

Slave paradise

Tranny.one 4 years ago

Mistress Kora Bell Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

Mistress Kora Bell Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

getTranny 1 week ago

”T-girl military has no borders”

”T-girl military has no borders”

4Wank 2 years ago

bbw fart punishment on trans girlfriend face & cock ass worship domination

HD 0:12 / 23:58

bbw fart punishment on trans girlfriend face & cock ass worship domination

PornBox 2 weeks ago

Sophia Loreen Party on Nov 20, 2025 - Part 2

4K 2:00 / 42:07

Sophia Loreen Party on Nov 20, 2025 - Part 2

Flirt4Free 1 month ago

Unhappy wife cheating husband with her transsexual BFF!

Unhappy wife cheating husband with her transsexual BFF!

aShemaleTube 5 years ago

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

KeekAss 6 months ago

Master & Christian & Nicco Private Show

63% HD 2:00 / 6:22

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

One blonde and two brunette trannies get a blowjob from

One blonde and two brunette trannies get a blowjob from

xHamster 10 months ago

Caught Peeping By Your Trans Roommate Teaser

Caught Peeping By Your Trans Roommate Teaser

xHamster 5 years ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 3 weeks ago

Lay Down with Me and Ejoy

HD 2:00 / 15:16

Lay Down with Me and Ejoy

Flirt4Free 2 years ago

Poor guy moans loudly as the beautiful tranny babe bangs him hard

Poor guy moans loudly as the beautiful tranny babe bangs him hard

Tranny.one 4 years ago

Put Your Tongue into My Foreskin

Put Your Tongue into My Foreskin

Flirt4Free 1 year ago

Tall Shemale Domina Punishes Hunk

Tall Shemale Domina Punishes Hunk

BeMyHole 3 months ago

Hang Ups & Hook Ups: Kayleigh Coxx Calls up Mason Lear

Hang Ups & Hook Ups: Kayleigh Coxx Calls up Mason Lear

xHamster 1 month ago

Lanna & Nefertiti Private Show

Lanna & Nefertiti Private Show

Flirt4Free 2 years ago

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

KAMS 11 months ago

Sophia Loreen Private Show

4K 2:00 / 1:23:18

Sophia Loreen Private Show

Flirt4Free 4 days ago

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

55% 0:39 / 32:47

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

FapHouse 2 weeks ago

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

69% HD 0:39 / 31:41

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

FapHouse 2 months ago

Welcome to Paradise Side of Prison

Welcome to Paradise Side of Prison

FapHouse 2 weeks ago

Shemale Police Officer punishes bad boy

Shemale Police Officer punishes bad boy

aShemaleTube 7 years ago

TS Mistress Dominates Beefy Sub

TS Mistress Dominates Beefy Sub

TrannyGem 1 week ago

Sophia Loreen Party on May 23, 2025 - Part 2

53% 4K 2:00 / 1:04:12

Sophia Loreen Party on May 23, 2025 - Part 2

Flirt4Free 7 months ago

Sissy Hope slut again giving to her hole a really harder punishment, loving rough and deep masturbation, damn bitch

Sissy Hope slut again giving to her hole a really harder punishment, loving rough and deep masturbation, damn bitch

xHamster 3 years ago

Maximum punishment for chaste loser slave: fuck rubber doll with cage!

Maximum punishment for chaste loser slave: fuck rubber doll with cage!

xHamster 11 months ago

Chastity Christmas! Nasty t-girl beauty gets punished! Drubbing! Mouthfuck! Assfuck!

Chastity Christmas! Nasty t-girl beauty gets punished! Drubbing! Mouthfuck! Assfuck!

FreePorn8 4 days ago

Amateur thief Casey Cumz cuffed and punished by trans Venus Lux

Amateur thief Casey Cumz cuffed and punished by trans Venus Lux

FetishShrine 1 week ago

”TS Aubrey Kate face fucks & assfucking plows Pierce Paris”

”TS Aubrey Kate face fucks & assfucking plows Pierce Paris”

429Men 3 days ago

Sophia Loreen Party on Jul 1, 2025 - Part 2

50% HD 2:00 / 30:11

Sophia Loreen Party on Jul 1, 2025 - Part 2

Flirt4Free 6 months ago

This Town Ain't Big Enough for the Two of Us: Futa Sheriff Gives Criminal Rough Punishment Pegging

This Town Ain't Big Enough for the Two of Us: Futa Sheriff Gives Criminal Rough Punishment Pegging

FapHouse 1 week ago

Sophia Loreen Party on Dec 27, 2025 - Part 2

65% 4K 2:00 / 45:19

Sophia Loreen Party on Dec 27, 2025 - Part 2

Flirt4Free 3 weeks ago

”Shemale Aspen Brooks dominates & pounds Jessie Prather butt”

”Shemale Aspen Brooks dominates & pounds Jessie Prather butt”

LesbianBliss 2 weeks ago

Embarrassing Jerk off in Black Stockings and Slut Heels

Embarrassing Jerk off in Black Stockings and Slut Heels

FapHouse 5 months ago

hard pegging male in the kitchen

hard pegging male in the kitchen

AnalVids 1 year ago

Latina Red Movie Punishes Her Big Ass with Her Toy to Make You Put Your Tongue

Latina Red Movie Punishes Her Big Ass with Her Toy to Make You Put Your Tongue

FapHouse 4 days ago

”Nutty : Bareback Punishment”

”Nutty : Bareback Punishment”

TransHero 5 years ago

Sexy dance, savage twerk, enjoy my streaptase while i make my body shine with oil, twerk in your face and red spanks, lets make my pussy wet with me riding my NEW TOY!

HD 2:00 / 19:53

Sexy dance, savage twerk, enjoy my streaptase while i make my body shine with oil, twerk in your face and red spanks, lets make my pussy wet with me riding my NEW TOY!

Flirt4Free 3 years ago

”Fucked Behind Bars”

”Fucked Behind Bars”

429Men 4 months ago

Release Me! Superman is the Villain's Bitch by ManUpFilms

Release Me! Superman is the Villain's Bitch by ManUpFilms

xHamster 1 year ago

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant

BeMyHole 2 years ago

Trans Angels Vaniity And Mia Isabella Dominate And Punish Thieves With Hardcore Sex

Trans Angels Vaniity And Mia Isabella Dominate And Punish Thieves With Hardcore Sex

KeekAss 2 days ago

Addam Parker Private Show

Addam Parker Private Show

Flirt4Free 3 years ago

TS Natalie Mars fisted and stretched by MILF Penny Barber

TS Natalie Mars fisted and stretched by MILF Penny Barber

VikiPorn 6 months ago

Justin Evanss Private Show

HD 2:00 / 13:53

Justin Evanss Private Show

Flirt4Free 3 weeks ago

Fit shemale domina punishing a dude and fucking him in the ass

Fit shemale domina punishing a dude and fucking him in the ass

aShemaleTube 10 months ago

Chanel Santini Has To Punish Her Employees When They Get Caught Masturbating On The Clock!

Chanel Santini Has To Punish Her Employees When They Get Caught Masturbating On The Clock!

BeMyHole 2 years ago

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

Tranny.one 4 years ago

”Zafira out to punish her hoe”

”Zafira out to punish her hoe”

TransHero 3 weeks ago

Sophia Loreen Private Show

64% 4K 2:00 / 20:27

Sophia Loreen Private Show

Flirt4Free 3 months ago

crossdresser bitch

crossdresser bitch

MenGem 3 years ago

Hanna Ven Private Show

44% HD 2:00 / 11:49

Hanna Ven Private Show

Flirt4Free 1 year ago

Arrogant Man Dominated by TS Boss

Arrogant Man Dominated by TS Boss

TrannyGem 1 week ago

Julia Gives Student a Schooling - TGirlJapan

Julia Gives Student a Schooling - TGirlJapan

AbTranny 6 years ago

Patric & Oliver Private Show

68% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 3 years ago

Crossdresser punished

Crossdresser punished

aShemaleTube 1 year ago

Punish Chair, Let Me Cum to Becoming a Fountain

Punish Chair, Let Me Cum to Becoming a Fountain

xHamster 3 weeks ago

Latex Punishment and Fingering [Chastity OTK finger fuck]

HD 0:10 / 15:30

Latex Punishment and Fingering [Chastity OTK finger fuck]

LoyalFans 2 months ago

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

Premium 39% 20:43

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

XVideosRed 1 year ago

Dani Saenz Private Show

Dani Saenz Private Show

Flirt4Free 4 years ago

Jenny Wei is BACK! Jenny gets fucked by The BBC PUNISHER full video available now 😈

Jenny Wei is BACK! Jenny gets fucked by The BBC PUNISHER full video available now 😈

aShemaleTube 6 months ago

Shemale fucks male sub in pink dungeon

Shemale fucks male sub in pink dungeon

GayVids 4 months ago

Hot Shemale Made My Wife Cum & Orgasm Better Then I Can

Hot Shemale Made My Wife Cum & Orgasm Better Then I Can

xHamster 10 months ago

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

xHamster 2 months 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 8 months ago

BDSM Bondage Sex Slave Harley Sissy Crossdresser Slut POV

BDSM Bondage Sex Slave Harley Sissy Crossdresser Slut POV

xHamster 4 years ago

BDSM mommy punish me hard I also want to be always good

BDSM mommy punish me hard I also want to be always good

xHamster 3 years ago

Shemale Punishes Her Puffy Nipples Until Lactation

66% HD 0:39 / 5:40

Shemale Punishes Her Puffy Nipples Until Lactation

FapHouse 4 months ago

Short haired woman enjoys getting her ass spanked by her lord

Short haired woman enjoys getting her ass spanked by her lord

xHamster 1 year ago

crossdresser slave bitch

crossdresser slave bitch

aShemaleTube 4 years ago

Brihana Boll Private Show

HD 2:00 / 33:23

Brihana Boll Private Show

Flirt4Free 4 months ago

Shemales Punishing Men In Bondage

Shemales Punishing Men In Bondage

BeMyHole 10 months ago

”Elise Fatal Is Tied Up & Her Butt Is Banged Red”

”Elise Fatal Is Tied Up & Her Butt Is Banged Red”

429Men 3 weeks ago

Lizz_ss25 wax and piss sissy who're

Lizz_ss25 wax and piss sissy who're

xHamster 2 years ago

TS Kendall Penny Punishes For Faulty Laundry

61% HD 3:00 / 50:00

TS Kendall Penny Punishes For Faulty Laundry

AEBN 6 months ago

”TBabe military has no borders”

”TBabe military has no borders”

LesbianBliss 4 weeks ago

crossdresser slave

crossdresser slave

Eporner 1 year 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

hard pegging male in the kitchen

hard pegging male in the kitchen

PornBox 1 year ago

”VRB TRANSGENDER Bratty mistress Mia Maffia punish her friend VR Porn”

”VRB TRANSGENDER Bratty mistress Mia Maffia punish her friend VR Porn”

Zatube 1 year ago

Busty tranny boss loves to feel big black cock in her nice butt

Busty tranny boss loves to feel big black cock in her nice butt

XGroovy 2 years ago

”Ricky Larkin comes home with hard dick for Daisy Taylor”

”Ricky Larkin comes home with hard dick for Daisy Taylor”

TransHero 4 years ago

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