Bdsm Punishment Videos (41,484)

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Tranny.one 4 years ago

Kinky twink gets his ass plummeted by the nasty Tgirl on the couch

Kinky twink gets his ass plummeted by the nasty Tgirl on the couch

Tranny.one 4 years ago

Caroline Bella Private Show

HD 2:00 / 10:26

Caroline Bella Private Show

Flirt4Free 2 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

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

Trashreality 10 months ago

Watch torment of a Asian shemale

Watch torment of a Asian shemale

XHamster 2 years ago

Shemale Punishes Her Puffy Nipples Until Lactation

65% HD 1:01 / 5:40

Shemale Punishes Her Puffy Nipples Until Lactation

FapHouse 10 months ago

Sophia Loreen Strip

54% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 3 years ago

Wild Sabrina Private Show

50% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 6 years 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

Sophia Loreen Private Show

73% HD 2:00 / 18:04

Sophia Loreen Private Show

Flirt4Free 2 months 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

GetTranny 7 months ago

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

69% HD 0:39 / 11:02

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

FapHouse 3 months ago

Dustin & Angel & Bayron Private Show

53% HD 2:00 / 4:45

Dustin & Angel & Bayron Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Jun 19, 2026 - Part 3

65% HD 2:00 / 47:03

Sophia Loreen Party on Jun 19, 2026 - Part 3

Camster 2 weeks ago

Shemale Asuka Extreme Tits Vacuum Pump Lactation and Nipple Punishment with Heels

Shemale Asuka Extreme Tits Vacuum Pump Lactation and Nipple Punishment with Heels

XHamster 1 month ago

Trans woman forming a submissive partner with dogplay while her husband films.

Trans woman forming a submissive partner with dogplay while her husband films.

BoyFriendTV 3 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 day ago

Sophia Loreen Party on Jun 18, 2026 - Part 4

67% HD 2:00 / 58:05

Sophia Loreen Party on Jun 18, 2026 - Part 4

Flirt4Free 2 weeks ago

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

XHamster 1 year ago

Orianna Dunn Private Show

47% HD 2:00 / 4:33

Orianna Dunn Private Show

Flirt4Free 2 years ago

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

63% HD 0:10 / 27:36

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

LoyalFans 1 year ago

Sissy Dee should be cleaning, but she gets carried away playing

Sissy Dee should be cleaning, but she gets carried away playing

XHamster 2 months ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

XHamster 7 months ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

XHamster 1 month ago

Beautiful Kasey Kei submits to King Noire for rough anal punishment

Beautiful Kasey Kei submits to King Noire for rough anal punishment

Fapnado 1 year ago

TRANSFIXED - Two Naughty Students In Detention Get Punished By Hot Trans Teacher TS Foxxy

TRANSFIXED - Two Naughty Students In Detention Get Punished By Hot Trans Teacher TS Foxxy

Some.Porn 6 months ago

Sophia Loreen Private Show

61% HD 2:00 / 8:40

Sophia Loreen Private Show

Camster 2 weeks ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

69% HD 0:39 / 7:13

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

FapHouse 3 months ago

”Blonde babe shocked on the streets”

”Blonde babe shocked on the streets”

TransHero 7 months ago

Fucked him before work. Hardcore Pegging!

Fucked him before work. Hardcore Pegging!

XVideosRed 1 year ago

Sissy Maid Self Bondage Electro Punishment

Sissy Maid Self Bondage Electro Punishment

XHamster 3 years ago

Sissy Dee and Lady Fee in Matching Outfits

63% HD 0:39 / 7:45

Sissy Dee and Lady Fee in Matching Outfits

FapHouse 1 week ago

Shemales in leather boots tie up a man before fucking him in

Shemales in leather boots tie up a man before fucking him in

XHamster 1 year ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

55% HD 2:00 / 56:20

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 3 months ago

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

Tranny.one 4 years ago

Dani Saenz Private Show

HD 2:00 / 40:44

Dani Saenz Private Show

Flirt4Free 4 years ago

Viky & Master Private Show

46% HD 2:00 / 9:05

Viky & Master Private Show

Flirt4Free 7 months ago

squirt - Part 2

59% 4K 2:00 / 9:52

squirt - Part 2

Flirt4Free 1 year ago

Hot White Dress

Hot White Dress

Flirt4Free 3 months ago

SEXY TRANS VARIETYITSOL RECEIVES PUNISHMENT AND PEGGING FROM LIVIE BLAINN

SEXY TRANS VARIETYITSOL RECEIVES PUNISHMENT AND PEGGING FROM LIVIE BLAINN

XHamster 10 months ago

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

58% HD 0:39 / 5:12

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

FapHouse 3 months ago

Finger Blowjob Hot Sexy

Finger Blowjob Hot Sexy

Flirt4Free 3 months ago

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

XHamster 2 years ago

Gia Darling and Her Scrub Brush

Gia Darling and Her Scrub Brush

XHamster 1 year ago

Transvestite from hell

Transvestite from hell

XHamster 1 year ago

Sophia Loreen Party on May 13, 2026 - Part 3

62% HD 2:00 / 34:53

Sophia Loreen Party on May 13, 2026 - Part 3

Flirt4Free 1 month ago

Eva Lin First Trans BDSM Domination

Eva Lin First Trans BDSM Domination

GayVids 4 months ago

King Noire Fucks Pixi Lust Tiny Asshole

King Noire Fucks Pixi Lust Tiny Asshole

GayVids 4 months ago

Hanna Ven Private Show

61% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 2 years ago

Busty shemale punisher spanks and fucks her lover with a

Busty shemale punisher spanks and fucks her lover with a

XHamster 1 year ago

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

65% HD 1:01 / 9:37

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

FapHouse 1 year ago

Tv Goddess Foxxy Punishes Loser Boyfriend

Tv Goddess Foxxy Punishes Loser Boyfriend

Tranny.one 4 years ago

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

GetTranny 3 years ago

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

56% HD 0:39 / 21:15

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

FapHouse 1 week ago

Submissive bloke gets his ass destroyed by the horny TS babe

Submissive bloke gets his ass destroyed by the horny TS babe

Tranny.one 4 years ago

Columbian Boys Wedgie War

54% HD 2:00 / 15:54

Columbian Boys Wedgie War

Flirt4Free 9 months ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

64% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 5 months ago

Jessica Dolls Weekly Fuckmachine Therepy

62% HD 0:39 / 12:59

Jessica Dolls Weekly Fuckmachine Therepy

FapHouse 5 months ago

Pledge and get spot for my group show..start now!!

64% HD 2:00 / 19:52

Pledge and get spot for my group show..start now!!

Flirt4Free 6 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 4 months ago

Leya Falcon punishes Aphrodite Adams with massive strap on

Leya Falcon punishes Aphrodite Adams with massive strap on

Fapnado 1 month ago

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

Rainblow 1 year 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

Sexy secretary talks about small in meeting room

Sexy secretary talks about small in meeting room

Some.Porn 2 years ago

Viky & Emma Private Show

60% HD 2:00 / 5:59

Viky & Emma Private Show

Flirt4Free 5 months ago

Freaks of Nature 22 Midget two

Freaks of Nature 22 Midget two

SortPorn 3 years ago

Colombian Boys Private Show

64% HD 2:00 / 33:09

Colombian Boys Private Show

Flirt4Free 9 months ago

Sara & Elver Private Show

Sara & Elver Private Show

Camster 5 months ago

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

HD 0:39 / 19:40

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

FapHouse 4 days 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

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

Busty TS chick dominates a hogtied submissive masked man

Busty TS chick dominates a hogtied submissive masked man

Tranny.one 4 years ago

BDSM Bondage Sex Slave Harley Sissy Crossdresser Slut POV

BDSM Bondage Sex Slave Harley Sissy Crossdresser Slut POV

XHamster 4 years ago

Sophia Loreen Private Show

72% 4K 2:00 / 13:07

Sophia Loreen Private Show

Flirt4Free 7 months ago

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

66% HD 1:01 / 15:56

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

FapHouse 8 months ago

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Tranny.one 4 years ago

SQUIRT IN FACE!

55% 4K 2:00 / 10:00

SQUIRT IN FACE!

Flirt4Free 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 4 years ago

Wild Sabrina Members-Only Show

46% HD 2:00 / 12:20

Wild Sabrina Members-Only Show

Flirt4Free 5 years ago

Hot Trans Vaniity Mia Isabella Fuck

Hot Trans Vaniity Mia Isabella Fuck

TransTube.tv 1 week ago

Slave rental

XHamster 1 year ago

Troy Khalil Private Show

74% HD 2:00 / 18:38

Troy Khalil Private Show

Flirt4Free 2 years ago

Troy Khalil Private Show

64% HD 2:00 / 5:47

Troy Khalil Private Show

Flirt4Free 2 years ago

Trans domme beats and fucks FtM in Pillory - Jaq Quicksilver and Cherry Mavrik - MtF dominatrix puts trans man in bondage for punishment - T4T, stocks, BDSM, ts, spanking, facefuck

Premium HD 25:05

Trans domme beats and fucks FtM in Pillory - Jaq Quicksilver and Cherry Mavrik - MtF dominatrix puts trans man in bondage for punishment - T4T, stocks, BDSM, ts, spanking, facefuck

XVideosRed 1 year ago

Sissy Gimp Disciplined for Vaping instead of Smoking

Sissy Gimp Disciplined for Vaping instead of Smoking

TrannyGem 5 years ago

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

XHamster 1 year ago

Leather mistress punishes sub with gayblowjob

Leather mistress punishes sub with gayblowjob

SexTubeSpot 5 years ago

Discipline for the Office Cuties

Discipline for the Office Cuties

Dafreeporn 3 days ago

See the New Slave They Humiliate, Torment & Hard Fist

56% HD 0:39 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year ago

Her Prisoner Part 22 - Sissy Training V **MOV**

59% 4K 0:33 / 10:09

Her Prisoner Part 22 - Sissy Training V **MOV**

Clips4sale 2 years ago

Three amateur shemale sex party

Three amateur shemale sex party

Fetishpapa 2 days ago

Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!

Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!

XHamster 2 years ago

Crossdresser punished and humiliated by merciless mistress

Crossdresser punished and humiliated by merciless mistress

PornLib 7 months ago

Paulo & Liam Private Show

HD 2:00 / 10:03

Paulo & Liam Private Show

Flirt4Free 1 day ago

crossdresser slave

crossdresser slave

Eporner 2 years ago

Nature Can Be a Real Gem

Nature Can Be a Real Gem

Some.Porn 1 year ago

Bob & Stivens & Patric Private Show

64% HD 2:00 / 5:10

Bob & Stivens & Patric Private Show

Flirt4Free 3 years ago

Femdom Mistress Punishes Submissive with Outdoor Caning

Femdom Mistress Punishes Submissive with Outdoor Caning

XXXShake 4 years ago

Discipline for the Office Angels

Discipline for the Office Angels

PornFreeNow 3 days ago

A Day in the Life of a Sissy Part 2

A Day in the Life of a Sissy Part 2

FapHouse 6 days ago

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

55% HD 0:39 / 25:09

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

FapHouse 11 months ago

Boi paddles his ass red while plugged and gaped

Boi paddles his ass red while plugged and gaped

XHamster 2 weeks 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

Sophia Loreen Private Show

55% 4K 2:00 / 58:12

Sophia Loreen Private Show

Flirt4Free 1 year ago

Wearing to cross dress

Wearing to cross dress

XHamster 1 year ago

Jacob Malik Private Show

58% HD 2:00 / 11:23

Jacob Malik Private Show

Flirt4Free 4 months ago

Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged

Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged

XHamster 2 years ago

Ambar & Oliver Private Show

54% HD 2:00 / 7:59

Ambar & Oliver Private Show

Flirt4Free 2 months ago

Booty trans Jessy Dubai punishes Ruckus and gives him BDSM session

Booty trans Jessy Dubai punishes Ruckus and gives him BDSM session

MenGem 1 year ago

Mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min

Mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min

AbTranny 3 years ago

squirt!! - Part 3

65% HD 2:00 / 9:53

squirt!! - Part 3

Flirt4Free 2 months ago

Dude fucks tied-up slave

Dude fucks tied-up slave

Some.Porn 1 year ago

Brutus K Private Show

57% HD 2:00 / 6:01

Brutus K Private Show

Flirt4Free 9 years ago

TS Morgan Bailey humiliates Ryan Patrix in wild two on one threesome

TS Morgan Bailey humiliates Ryan Patrix in wild two on one threesome

Fapnado 1 year ago

Nicolle & Christian Private Show

50% HD 2:00 / 5:47

Nicolle & Christian Private Show

Flirt4Free 10 months ago

Discipline for the Office Beauties

Discipline for the Office Beauties

FreePorn8 3 days ago

Latex &amp_ Bondage III - Gray Perrier dominates Ava Holt in a Trans Lesbian Bondage Scene filled with power exchange, impact, and riding her until she explodes

Premium HD 39:22

Latex &amp_ Bondage III - Gray Perrier dominates Ava Holt in a Trans Lesbian Bondage Scene filled with power exchange, impact, and riding her until she explodes

XVideosRed 4 months ago

Honey FoXXX and Scout in Steamy Locker Room Encounter with College -Censored- Crush

Honey FoXXX and Scout in Steamy Locker Room Encounter with College -Censored- Crush

Sheshaft 1 month ago

Ema Devine Private Show

Ema Devine Private Show

Camster 1 year ago

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