Punishment Videos (39,619)

”Bitch stuffed with sausages in public”

”Bitch stuffed with sausages in public”

TransHero 1 month ago

Doctor Brutus Exams You and Takes Your Sperm in Latex Gloves

51% HD 2:00 / 5:34

Doctor Brutus Exams You and Takes Your Sperm in Latex Gloves

Flirt4Free 7 years ago

Cuffed, Spanked & Toyed

Cuffed, Spanked & Toyed

Tranny.one 4 years ago

”Big tits tranny Leilani Li anally rammed submissive blond Sage Roux”

”Big tits tranny Leilani Li anally rammed submissive blond Sage Roux”

LesbianBliss 1 week ago

”Dillon Diaz gets seduced from Tranny boss Gracie Jane”

”Dillon Diaz gets seduced from Tranny boss Gracie Jane”

LesbianBliss 1 week ago

pee in my pussy after sex w roxie moth pt 2

pee in my pussy after sex w roxie moth pt 2

PornBox 1 year ago

Your Love of Pain Gets You the Cane

72% 1:01 / 10:07

Your Love of Pain Gets You the Cane

FapHouse 11 months ago

Dance

HD 2:00 / 1:31:22

Flirt4Free 1 year ago

”Pissed trans Korra Del Rio pumps white man”

”Pissed trans Korra Del Rio pumps white man”

429Men 3 weeks ago

Liam Jacobson Private Show

61% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 2 months ago

The BBC Punisher fucks Jenny Wei

The BBC Punisher fucks Jenny Wei

aShemaleTube 2 years ago

Roy is a the Best Bottom

50% HD 2:00 / 9:57

Roy is a the Best Bottom

Flirt4Free 3 years ago

”Mesmerizing Kasey Kei submits to King Noire for rough ass pumping punishment”

”Mesmerizing Kasey Kei submits to King Noire for rough ass pumping punishment”

Fapnow 7 months ago

TS sub in latex Ella Hollywood bound and anal punished by master Sebastian Keys

TS sub in latex Ella Hollywood bound and anal punished by master Sebastian Keys

KeekAss 4 months ago

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

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

xHamster 1 year ago

Nyobi Khan and Rico

Nyobi Khan and Rico

xHamster 7 months ago

Ts punish girl and wet rough sex first time Cummie, the Painal Cum Cat

Ts punish girl and wet rough sex first time Cummie, the Painal Cum Cat

Eporner 6 years ago

Hard Cash Payback!

Hard Cash Payback!

xHamster 1 year ago

Alexander Batista Private Show

HD 2:00 / 11:35

Alexander Batista Private Show

Flirt4Free 3 years ago

Krista Becomes Fucktoy for BDSM Big Ass Big Tits Mistress with Sadistic Dildo Humiliation and Slave Helpers Fuck Punishment

61% HD 1:01 / 22:36

Krista Becomes Fucktoy for BDSM Big Ass Big Tits Mistress with Sadistic Dildo Humiliation and Slave Helpers Fuck Punishment

FapHouse 3 years ago

Sissy Gimp Disciplined for Vaping instead of Smoking

Sissy Gimp Disciplined for Vaping instead of Smoking

TrannyGem 5 years 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

Lilly Riley Party on Apr 11, 2023 - Part 3

HD 2:00 / 15:24

Lilly Riley Party on Apr 11, 2023 - Part 3

Flirt4Free 2 years ago

Muscular submissive slave man wants to be tied and whipped

Muscular submissive slave man wants to be tied and whipped

xHamster 2 years ago

Liam Jacobson Private Show

46% HD 2:00 / 38:49

Liam Jacobson Private Show

Flirt4Free 1 year ago

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Tranny.one 4 years ago

”Amazingly adorable TBabe Khloe Kay's butt is marvelous”

”Amazingly adorable TBabe Khloe Kay's butt is marvelous”

HQBang 2 years ago

Iasmym Rios in high heels gets sucked and fucks her slave

Iasmym Rios in high heels gets sucked and fucks her slave

xHamster 10 months ago

futa sheriff gives criminal rough punishment pegging - full video on Veggiebabyy Manyvids

futa sheriff gives criminal rough punishment pegging - full video on Veggiebabyy Manyvids

xHamster 3 weeks ago

Lanista bear and Allegro in the Dungeon part 3

Lanista bear and Allegro in the Dungeon part 3

xHamster 2 months ago

Elias & Elix Private Show

61% HD 2:00 / 41:34

Elias & Elix Private Show

Flirt4Free 3 months ago

Sophia Loreen Party on Jan 24, 2026 - Part 2

4K 2:00 / 22:20

Sophia Loreen Party on Jan 24, 2026 - Part 2

Flirt4Free 1 week ago

Viky & Master Private Show

63% HD 2:00 / 25:32

Viky & Master Private Show

Flirt4Free 5 months ago

Beg for my strapon! Your ass needs punished.

Beg for my strapon! Your ass needs punished.

ALOTPorn 7 months ago

Freya Bliss Party on Dec 3, 2025 - Part 2

57% HD 2:00 / 32:21

Freya Bliss Party on Dec 3, 2025 - Part 2

Flirt4Free 2 months ago

Feelipe & Adara Private Show

62% HD 2:00 / 12:01

Feelipe & Adara Private Show

Flirt4Free 7 months ago

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Jenny

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Jenny

xHamster 3 years ago

Cute T-beauty Armpits Unshaved Masturbation and Titjob to Sex tool

Cute T-beauty Armpits Unshaved Masturbation and Titjob to Sex tool

Dafreeporn 6 days ago

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

FapHouse 1 year ago

Sophia Loreen Party on May 23, 2025 - Part 2

4K 2:00 / 35:08

Sophia Loreen Party on May 23, 2025 - Part 2

Flirt4Free 8 months ago

Elvis & Alfonso & Master Private Show

63% HD 2:00 / 14:58

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

Sheshaft 8 years ago

Dominant trans chick sticks her thick Tcock in the sissy's ass deep and hard

Dominant trans chick sticks her thick Tcock in the sissy's ass deep and hard

Tranny.one 4 years ago

Sandy Nell Private Show

69% HD 2:00 / 4:00

Sandy Nell Private Show

Flirt4Free 3 years ago

TS Maid Punished

TS Maid Punished

xHamster 2 years ago

Transsexual Superstars 2

70% HD 0:30 / 4:00:00+

Transsexual Superstars 2

AEBN 3 years ago

Graziella Toledo's massive tits and tight ass dominate helpless dude in hardcore BDSM session

Graziella Toledo's massive tits and tight ass dominate helpless dude in hardcore BDSM session

FetishShrine 2 months ago

”River Enza punishes big transgender butthole with dildo”

”River Enza punishes big transgender butthole with dildo”

4Wank 1 year ago

Treated like a slut and squeezed like a cow

Treated like a slut and squeezed like a cow

xHamster 1 year ago

Four trannies in black leather outfits enjoy dominating

Four trannies in black leather outfits enjoy dominating

xHamster 1 year ago

Kitsy - Paddled & caned (a severe flogging in strappado with anal hook)

Kitsy - Paddled & caned (a severe flogging in strappado with anal hook)

ShemaleSin 3 years ago

Whipping Punishment for the Sissy Slut - Part 1

Whipping Punishment for the Sissy Slut - Part 1

xHamster 1 year ago

Raid Over Japan Asian Ladyboy Punished And Fucked In AS

Raid Over Japan Asian Ladyboy Punished And Fucked In AS

Eporner 1 year ago

Bad ladyboy punished for cheating

Bad ladyboy punished for cheating

Eporner 2 years ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

Trashreality 1 year ago

Crossdresser slave

Crossdresser slave

Fetishpapa 4 years ago

Babysit On My Chest

Babysit On My Chest

Some.Porn 5 months ago

Cheating latina wife punish fucked by angry husband

Cheating latina wife punish fucked by angry husband

ALOTPorn 5 years ago

Banged Behind Bars

Premium 56% HD 19:10

Banged Behind Bars

TransAngels 1 year ago

Kira's punishment part one

HD 1:01 / 13:00

Kira's punishment part one

FapHouse 3 years ago

TS Slave Maid Spanking Punishment | MahoganyQen

68% HD 0:10 / 10:48

TS Slave Maid Spanking Punishment | MahoganyQen

LoyalFans 9 months ago

Collection of beautiful tranny chicks banging the lucky guys fat ass in hardcore amateur scenes

Collection of beautiful tranny chicks banging the lucky guys fat ass in hardcore amateur scenes

Tranny.one 4 years ago

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

Premium 50% HD 13:39

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

XVideosRed 1 year ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 3 years ago

TS Yoga Instructor Dominates Foot-Sniffer

TS Yoga Instructor Dominates Foot-Sniffer

Tranny.one 4 years ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 3 weeks ago

Petite TS Avery Angel loves BBC! Avery gets punished she's so hot!

Petite TS Avery Angel loves BBC! Avery gets punished she's so hot!

aShemaleTube 1 month ago

The fat sissy pig has fun with the dildo

The fat sissy pig has fun with the dildo

xHamster 1 month ago

Big Dick Trans Mommy Cumming and Milking her Tits

Big Dick Trans Mommy Cumming and Milking her Tits

xHamster 2 months ago

Viky & Master Private Show

56% HD 2:00 / 13:43

Viky & Master Private Show

Flirt4Free 2 months ago

Schwangere holt sich Callboy

Schwangere holt sich Callboy

Tranny.one 4 years ago

Lady Punishes Her Sissy Slut Michelle for Not Wearing Propper Lingerie for Bed

Lady Punishes Her Sissy Slut Michelle for Not Wearing Propper Lingerie for Bed

Tranny.one 1 year ago

That’s What Happened in the New Slave Welcome Room

40% HD 1:01 / 8:02

That’s What Happened in the New Slave Welcome Room

FapHouse 2 years ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

59% HD 0:39 / 49:11

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

FapHouse 1 month ago

PURE TABOO - Mail order bride gets creampie

HD 1:01 / 1:05:50

PURE TABOO - Mail order bride gets creampie

FapHouse 5 years ago

TS Boss Punishes Employee!

TS Boss Punishes Employee!

aShemaleTube 6 years ago

TS Jessica Fox whips out her meat and fucks lustful Owen Michaels

TS Jessica Fox whips out her meat and fucks lustful Owen Michaels

UrGayPorn 5 months ago

Nyobi Khan - Cock Worship

Nyobi Khan - Cock Worship

xHamster 8 months ago

Unhappy wife cheating husband with her transsexual BFF!

Unhappy wife cheating husband with her transsexual BFF!

aShemaleTube 5 years ago

Worship My Package from a Very Close Distance

Worship My Package from a Very Close Distance

Flirt4Free 2 years ago

Liam Jacobson Private Show

61% HD 2:00 / 6:16

Liam Jacobson Private Show

Flirt4Free 1 year ago

Trans Girl Punishes And Dominates This Guy And Destroys His Asshole Roughly

Trans Girl Punishes And Dominates This Guy And Destroys His Asshole Roughly

BeMyHole 2 years ago

Dionisio & Perseo & Elvis Private Show

53% HD 2:00 / 30:47

Dionisio & Perseo & Elvis Private Show

Flirt4Free 3 years ago

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

UrGayPorn 3 months ago

Michelle Firestone swaps her pecker in and out of Juliette Marchs holes

Michelle Firestone swaps her pecker in and out of Juliette Marchs holes

Sheshaft 6 months ago

Chrismas Pegging for Lazy Elf Loren Aprile

Premium HD 23:10

Chrismas Pegging for Lazy Elf Loren Aprile

xnxxGold 2 years ago

TGirl Ria Bentley Gets Her Ass Punished By Car Repair Guy

63% HD 0:10 / 15:49

TGirl Ria Bentley Gets Her Ass Punished By Car Repair Guy

LoyalFans 3 months ago

Patric & Alexander & Lian Private Show

42% HD 2:00 / 33:17

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Sarah Dark her Own Crossdressing Sissy

Sarah Dark her Own Crossdressing Sissy

its.PORN 6 years ago

Crossdresser slut caught wanking her big cock is tied up for ass and cock punishment

Crossdresser slut caught wanking her big cock is tied up for ass and cock punishment

aShemaleTube 9 years ago

Nick & Diego & Liam Private Show

53% HD 2:00 / 1:00:15

Nick & Diego & Liam Private Show

Flirt4Free 3 years ago

Trans Larissa Albuquerque buggers bareback the crook who wanted to punish her

Trans Larissa Albuquerque buggers bareback the crook who wanted to punish her

xHamster 1 year ago

gangbang part.2 - punishing the mechanic who didnt deliver the job

gangbang part.2 - punishing the mechanic who didnt deliver the job

PornOne 1 year ago

Izzy Wilde tells stepbro she has a cock and gets anal punishment

Izzy Wilde tells stepbro she has a cock and gets anal punishment

AnySex 3 years ago

Caught with My Knickers Down!

Caught with My Knickers Down!

Flirt4Free 3 years ago

”T-girl Sergeant Jessy Dubai Trains Her New Recruits”

”T-girl Sergeant Jessy Dubai Trains Her New Recruits”

Fapnow 1 year ago

Crossdresser Dominates Breasts and Armpits 1

Crossdresser Dominates Breasts and Armpits 1

xHamster 3 months ago

Michelle Firestone swaps her dick in and out of Juliette Marchs holes

Michelle Firestone swaps her dick in and out of Juliette Marchs holes

SleazyNEasy 6 months ago

Sophia Loreen Party on May 17, 2025 - Part 2

46% 4K 2:00 / 21:35

Sophia Loreen Party on May 17, 2025 - Part 2

Flirt4Free 8 months 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

Sheshaft 7 years ago

Teen ladyboy Ass Punished Bareback

Teen ladyboy Ass Punished Bareback

Pornwhite 3 days ago

Troy & Kiros Private Show

HD 2:00 / 23:22

Troy & Kiros Private Show

Flirt4Free 1 year ago

Robbie Edwards Private Show

HD 2:00 / 35:16

Robbie Edwards Private Show

Flirt4Free 1 year ago

TS Yasmin Lee humiliates her sexist boss Lucas Knight with her meat

TS Yasmin Lee humiliates her sexist boss Lucas Knight with her meat

SleazyNEasy 6 months ago

Daddy fucks me in all positions

Daddy fucks me in all positions

xHamster 2 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 4 years ago

Tranny punisher Foxi strips her leather pants and plays with

Tranny punisher Foxi strips her leather pants and plays with

xHamster 9 months ago

Troy Khalil Party on Nov 6, 2025

45% 4K 2:00 / 50:13

Troy Khalil Party on Nov 6, 2025

Flirt4Free 3 months ago

Wild Sabrina Members-Only Show

56% HD 2:00 / 27:42

Wild Sabrina Members-Only Show

Flirt4Free 3 years ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 3 weeks ago

Charlie Cano Private Show

59% HD 2:00 / 20:04

Charlie Cano Private Show

Flirt4Free 3 years ago

Thai Sucker

Some.Porn 1 year ago

Spit on My Sweet Boobs

Spit on My Sweet Boobs

Flirt4Free 11 months ago

Post Climax Punishment - Black ilovelaylafeet lets me Cum inside her ripped Nylon

Post Climax Punishment - Black ilovelaylafeet lets me Cum inside her ripped Nylon

Ebony8 1 week ago

Futa Sailor Girl Domination: Latina Mistress Punishes Her Male Submissive

Futa Sailor Girl Domination: Latina Mistress Punishes Her Male Submissive

PornTopedia 1 month ago

Handcuffed Teen Ladyboy Swallows It All

Handcuffed Teen Ladyboy Swallows It All

Eporner 6 years ago

”Sexy Stepmom Tranny punishing naughty hubby”

”Sexy Stepmom Tranny punishing naughty hubby”

4Wank 2 years ago

My best friend told me that while he was away I would watch videos of the two of us Clip 1

My best friend told me that while he was away I would watch videos of the two of us Clip 1

xHamster 1 month ago

Ts bdsm Punish my nineteen year-old butt and mouth

Ts bdsm Punish my nineteen year-old butt and mouth

Eporner 3 years ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 8 months ago

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