Punishment Videos (58,791)

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

57% HD 1:01 / 7:45

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

FapHouse 5 months ago

Gay bottoms deepthroat then get their asses wrecked hard

Gay bottoms deepthroat then get their asses wrecked hard

AnalPornVids 2 months ago

Consequences for Breaking Out of Chastity

66% HD 1:01 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 1 month 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

Watch torment of a Asian shemale

Watch torment of a Asian shemale

XHamster 2 years ago

Futa Punishes Her Step-slut

64% 0:39 / 19:11

Futa Punishes Her Step-slut

FapHouse 5 months 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

Sophia Loreen Strip

54% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 3 years ago

Punish Her

BeMyHole 1 month ago

I'm Angry with You, My Boy! as a Punishment, You Punch Yourself While Jerking off! JOI CBT German

47% HD 0:39 / 7:44

I'm Angry with You, My Boy! as a Punishment, You Punch Yourself While Jerking off! JOI CBT German

FapHouse 5 months ago

Skinny ts punished by BBC

Skinny ts punished by BBC

KeekAss 1 month ago

Threesome with bella

Threesome with bella

Tranny.one 4 years ago

Young sissy edges and cums while riding huge dildo

Young sissy edges and cums while riding huge dildo

Tranny.one 4 years ago

Caught Stepbro in Fishnets - Now His Punishment Is Stepbrother’s Huge Cock

59% 1:01 / 9:57

Caught Stepbro in Fishnets - Now His Punishment Is Stepbrother’s Huge Cock

FapHouse 4 months 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

Wild Sabrina Private Show

50% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 6 years ago

Watch this hot Latino boy humiliate his buddy by making him pay for his sins on the roof

Watch this hot Latino boy humiliate his buddy by making him pay for his sins on the roof

GayVD 1 week ago

Hot teasing til you cum in your chastity cage! Tranny JOI for Chastity Losers!

Hot teasing til you cum in your chastity cage! Tranny JOI for Chastity Losers!

XHamster 3 weeks ago

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

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

XHamster 6 months ago

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

XHamster 1 year ago

TS Victoria Neves Punished And Fucked Bareback

TS Victoria Neves Punished And Fucked Bareback

Sheshaft 2 years ago

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

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

4Wank 3 years ago

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

73% HD 1:01 / 13:12

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

FapHouse 5 months ago

Mmm My Thong is So Wet

Mmm My Thong is So Wet

Flirt4Free 1 year 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

Newhalf hottie Koyuki Takahashi gets her ass fucked

66% HD 0:39 / 29:59

Newhalf hottie Koyuki Takahashi gets her ass fucked

FapHouse 5 years ago

Sissy's punishment

Sissy's punishment

XHamster 3 years ago

Dustin & Angel & Bayron Private Show

53% HD 2:00 / 4:45

Dustin & Angel & Bayron Private Show

Flirt4Free 2 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

BeMyHole 6 years ago

Jia’s Punishment

65% 4K 0:24 / 11:35

Jia’s Punishment

Futanari 4 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

GetTranny 7 months ago

Hot Asian Nurse Fucks TS step-daughter

HD 0:10 / 14:57

Hot Asian Nurse Fucks TS step-daughter

LoyalFans 1 week ago

Sophia Loreen Private Show

73% HD 2:00 / 18:04

Sophia Loreen Private Show

Flirt4Free 2 months ago

Edlin Dockray Private Show

63% HD 2:00 / 13:31

Edlin Dockray Private Show

Flirt4Free 2 years ago

Discipline for the Office Girls

Discipline for the Office Girls

Tranny.one 2 years ago

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

XHamster 1 month ago

West Wing Porn - the Dirtiest Business of All - Politics

HD 0:39 / 43:37

West Wing Porn - the Dirtiest Business of All - Politics

FapHouse 2 days 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

Two BBC Men Punish Cute TS Latina

Two BBC Men Punish Cute TS Latina

An4lPorn 2 years ago

Ts creampie guys ass first time Punish my nineteen year-old caboose and mouth

Ts creampie guys ass first time Punish my nineteen year-old caboose and mouth

Eporner 2 years 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 4 months 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

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

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

XHamster 4 months ago

Orianna Dunn Private Show

47% HD 2:00 / 4:33

Orianna Dunn Private Show

Flirt4Free 2 years ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

XHamster 7 months ago

Dominant Cherry Mavrik Torments Submissive TS Jamie French

Dominant Cherry Mavrik Torments Submissive TS Jamie French

XHamster 1 year ago

Big cock police officer Lucy fucking and humiliating chastity sub

Big cock police officer Lucy fucking and humiliating chastity sub

XHamster 4 months ago

Sophia Loreen Private Show

61% HD 2:00 / 8:40

Sophia Loreen Private Show

Camster 2 weeks 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 3 weeks ago

Slut Takes Double Anal Punishment DP, DAP, ATM Covered in Cum Facials

Slut Takes Double Anal Punishment DP, DAP, ATM Covered in Cum Facials

XHamster 3 months 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

Hot Transgenderw

Hot Transgenderw

XHamster 4 months ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 8 years ago

Robber gets punished with some hardcore anal pounding by the horny TS chick

Robber gets punished with some hardcore anal pounding by the horny TS chick

Tranny.one 4 years ago

Anal Sluts: Audrey Rose and Lea Lexis

HD 1:01 / 1:24:48

Anal Sluts: Audrey Rose and Lea Lexis

FapHouse 3 weeks ago

Natalie Mars Punishment

Natalie Mars Punishment

Eporner 2 years ago

Tv Goddess Foxxy Punishes Loser Boyfriend

Tv Goddess Foxxy Punishes Loser Boyfriend

Tranny.one 4 years ago

Jacuzzi with French Trans Goddess Her GF Catches Us & Pegs Us Both

61% HD 1:01 / 32:18

Jacuzzi with French Trans Goddess Her GF Catches Us & Pegs Us Both

FapHouse 2 months ago

Nasty tranny cop Aylla fucks guy

Nasty tranny cop Aylla fucks guy

XHamster 1 year ago

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

XHamster 4 months ago

Tall shebabe punishes her bf's ass on the couch

Tall shebabe punishes her bf's ass on the couch

AShemaleTube 4 months ago

Cute Femboy punished by BBC

Cute Femboy punished by BBC

Eporner 1 year ago

Trans Maid Kaela Luna Wants to Be Used by Her New Boss

Trans Maid Kaela Luna Wants to Be Used by Her New Boss

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

”Faustine Lee gets punished”

”Faustine Lee gets punished”

ThePornstar 11 months ago

This Dildo Got What It Deserved

68% 0:39 / 4:05

This Dildo Got What It Deserved

FapHouse 6 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 9 years ago

”Blonde babe shocked on the streets”

”Blonde babe shocked on the streets”

TransHero 7 months ago

Young Waiter Has To Pay For His Clumsiness By Letting a Sexy Curvy Latina Tranny Fuck Him Hard

Young Waiter Has To Pay For His Clumsiness By Letting a Sexy Curvy Latina Tranny Fuck Him Hard

AnySex 1 year ago

Guess Who Got Punished This Time

63% 0:39 / 7:23

Guess Who Got Punished This Time

FapHouse 9 months 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

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

Jasmine_dlight & Pixie Vanora - a Deep & Sensual Exploration - Relentless Double Fist & Squirt

Jasmine_dlight & Pixie Vanora - a Deep & Sensual Exploration - Relentless Double Fist & Squirt

FapHouse 3 weeks ago

Guess Who Got Punished This Time

69% 1:01 / 7:23

Guess Who Got Punished This Time

FapHouse 9 months ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

XHamster 1 month ago

$I Think This is What You\'ve Wanted for So Long$ 54% 4K 0:42

I Think This is What You\'ve Wanted for So Long

Flirt4Free 4 months 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

Leela's Thanksgiving Day Dinner

59% HD 1:01 / 21:36

Leela's Thanksgiving Day Dinner

FapHouse 2 years ago

Julia Winston tops her lover

65% HD 0:39 / 31:09

Julia Winston tops her lover

FapHouse 5 years ago

Fucked him before work. Hardcore Pegging!

Fucked him before work. Hardcore Pegging!

XVideosRed 1 year 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

Gia Darling and Her Scrub Brush

Gia Darling and Her Scrub Brush

XHamster 1 year ago

A Day in the Life of a Sissy Part 2

A Day in the Life of a Sissy Part 2

FapHouse 1 week ago

Finger Blowjob Hot Sexy

Finger Blowjob Hot Sexy

Flirt4Free 3 months ago

Leather outfit ts domina punishes her slave's ass and mouth

Leather outfit ts domina punishes her slave's ass and mouth

AShemaleTube 5 months ago

Lika Kai Private Show

55% 4K 2:00 / 5:04

Lika Kai Private Show

Camster 2 weeks ago

Sissified by Lolth - Sissification, Chastity, Drow, D&d

Sissified by Lolth - Sissification, Chastity, Drow, D&d

FapHouse 1 year 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

Viky & Master Private Show

46% HD 2:00 / 9:05

Viky & Master Private Show

Flirt4Free 7 months ago

”T-girl wifey wait all day for her hubby's shaft”

”T-girl wifey wait all day for her hubby's shaft”

TransHero 3 years ago

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

ShemaleSex 20 hours ago

Drake Von punishes Khloe Kay for seducing his girlfriend

Drake Von punishes Khloe Kay for seducing his girlfriend

WeGotDicks 4 months ago

Corrine Dittmann Private Show

64% 4K 2:00 / 5:04

Corrine Dittmann Private Show

Flirt4Free 10 months ago

Ts dominates and rough sex with comrade duddy s sister Punish my nineteen year-old booty

Ts dominates and rough sex with comrade duddy s sister Punish my nineteen year-old booty

Eporner 8 years ago

Hot White Dress

Hot White Dress

Flirt4Free 3 months 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

Sexy secretary talks about small in meeting room

Sexy secretary talks about small in meeting room

Some.Porn 2 years 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

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

squirt - Part 2

59% 4K 2:00 / 9:52

squirt - Part 2

Flirt4Free 1 year ago

English Mistress punishes cross dressed guy

English Mistress punishes cross dressed guy

UiPorn 3 years ago

”Petite fan is viciously punished by her beloved femdom idol”

”Petite fan is viciously punished by her beloved femdom idol”

ThePornstar 1 year ago

Chubby ginger-haired babe punished with belt and dick by a hot shemale

Chubby ginger-haired babe punished with belt and dick by a hot shemale

GayX 2 months ago

Pink lingeried black shemale punishes her bf

Pink lingeried black shemale punishes her bf

AShemaleTube 4 months ago

Crossdresser punished and humiliated by merciless mistress

Crossdresser punished and humiliated by merciless mistress

PornLib 7 months ago

Real SISSY ENEMA slave cums in his own mouth

Real SISSY ENEMA slave cums in his own mouth

XHamster 1 year ago

Busty TS chick dominates a hogtied submissive masked man

Busty TS chick dominates a hogtied submissive masked man

Tranny.one 4 years 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

Jenna Reid Spanks Her French Maid Cross Dressing Cuckold

61% HD 1:01 / 33:29

Jenna Reid Spanks Her French Maid Cross Dressing Cuckold

FapHouse 3 years ago

Mara Nova and Sydney Farron In Punishment by Principal

Mara Nova and Sydney Farron In Punishment by Principal

Tranny.one 6 years ago

Hanna Ven Private Show

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

Hanna Ven Private Show

Flirt4Free 2 years ago

Shocking Confession to the Wedding Priest!

Shocking Confession to the Wedding Priest!

XHamster 2 years ago

Bad Cleaner Should Clean My Cock Now, Deepthroat Blowjob and Breeding Femboy's Tight Ass

58% 0:39 / 15:45

Bad Cleaner Should Clean My Cock Now, Deepthroat Blowjob and Breeding Femboy's Tight Ass

FapHouse 8 months ago

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

XHamster 2 months 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

Transvestite from hell

Transvestite from hell

XHamster 1 year ago

Nurse Tgirl fucked by perv policeman - GenderX Films

Nurse Tgirl fucked by perv policeman - GenderX Films

XGroovy 1 year ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

64% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 5 months ago

Butt Cork Black Nylons Jerk Off

Butt Cork Black Nylons Jerk Off

WebcamBros 2 weeks ago

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