Punishment Videos (40,371)

”Slave in waching machine in public”

”Slave in waching machine in public”

TransHero 2 months ago

”Ah honey don't be upset, I let you fuck me ok? - Korra Del Rio”

”Ah honey don't be upset, I let you fuck me ok? - Korra Del Rio”

TransHero 5 years ago

TS Roxxie Moth flogs and fucks naughty maid Arielle Aquinas

TS Roxxie Moth flogs and fucks naughty maid Arielle Aquinas

Fapcat 10 months ago

Courageous TS Natalie Mars Bends Down And Lets The Giant Rubber Dick Destroy Her Asshole

Courageous TS Natalie Mars Bends Down And Lets The Giant Rubber Dick Destroy Her Asshole

Eporner 11 months ago

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

Eporner 8 years ago

”TGIRLS HOOKUP: Lying Top Gets Humiliated & Punished!”

”TGIRLS HOOKUP: Lying Top Gets Humiliated & Punished!”

4Wank 1 year ago

Viky & Master Private Show

61% HD 2:00 / 9:03

Viky & Master Private Show

Flirt4Free 2 months ago

Tgirl Mistress Jade Venus Dominates Bound Sub Draven On Spinning Wheel She Fucks Him Hard

Tgirl Mistress Jade Venus Dominates Bound Sub Draven On Spinning Wheel She Fucks Him Hard

Sheshaft 1 month ago

Sophia Loreen Party on Oct 16, 2024 - Part 3

HD 2:00 / 18:33

Sophia Loreen Party on Oct 16, 2024 - Part 3

Flirt4Free 1 year ago

Wild Sabrina Members-Only Show

Wild Sabrina Members-Only Show

Flirt4Free 5 years ago

Punished for wearing wifes panties

Punished for wearing wifes panties

xHamster 2 years ago

Avery Angel gets Punished #2 trailer full video Available now! Only 4.99

Avery Angel gets Punished #2 trailer full video Available now! Only 4.99

aShemaleTube 11 months ago

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

aShemaleTube 1 month ago

Liam Jacobson Private Show

Liam Jacobson Private Show

Flirt4Free 1 year ago

”Incompetent Nanny Punished By Bondage Orgasm - Kristen Scott,Ryan Driller”

”Incompetent Nanny Punished By Bondage Orgasm - Kristen Scott,Ryan Driller”

ThePornstar 1 year ago

”Mansion maid teaches Eiji BDSM”

”Mansion maid teaches Eiji BDSM”

TransHero 2 months ago

”Bitch stuffed with sausages in public”

”Bitch stuffed with sausages in public”

TransHero 3 months ago

Shemale punishes bound muscle stud

Shemale punishes bound muscle stud

TransTube.tv 3 weeks ago

Crossdresser spanking

Crossdresser spanking

Fetishpapa 4 years ago

MILF librarian Mistress Kara punishes misbehaved TS Stefani Special

MILF librarian Mistress Kara punishes misbehaved TS Stefani Special

Fetishpapa 8 months ago

Exercise Torment By Sexy, Fitness Babe, Jaquelin Braxton

Exercise Torment By Sexy, Fitness Babe, Jaquelin Braxton

AbTranny 9 years ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 3 months ago

Three domina trannies in leather corsets fuck a dude in the

Three domina trannies in leather corsets fuck a dude in the

xHamster 11 months ago

Trans Stepsister Femdom

65% HD 0:39 / 17:03

Trans Stepsister Femdom

FapHouse 1 year ago

Eumelissa wants to find a father to play with me

Eumelissa wants to find a father to play with me

xHamster 10 months ago

Bound shemale slave anal fucked and punished

Bound shemale slave anal fucked and punished

KeekAss 1 year ago

One blonde and two brunette shemales tie up and dude and

One blonde and two brunette shemales tie up and dude and

xHamster 1 year ago

Sexy Student

63% HD 2:00 / 6:50

Flirt4Free 2 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 years ago

Elix & Elias & Paulo Private Show

45% HD 2:00 / 5:24

Elix & Elias & Paulo Private Show

Flirt4Free 8 months ago

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Sheshaft 5 months ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 1 week ago

Unhappy wife cheating husband with her transsexual BFF!

Unhappy wife cheating husband with her transsexual BFF!

Tranny.one 4 years ago

Ladyboy Sapphire Legal-age in sexy lingerie punishing her pretty cock

Ladyboy Sapphire Legal-age in sexy lingerie punishing her pretty cock

Xshemale 3 years ago

Naughty guy gets punished by TS teacher for misbehavior as she bangs his tight ass deep and hard with her huge Tcock

Naughty guy gets punished by TS teacher for misbehavior as she bangs his tight ass deep and hard with her huge Tcock

BeMyHole 5 years ago

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

aShemaleTube 3 months ago

Hawt Transgenderw

Hawt Transgenderw

PornFreeNow 2 days ago

Walking in the grocery store

Walking in the grocery store

xHamster 2 years ago

Sophia Loreen Private Show

HD 2:00 / 11:05

Sophia Loreen Private Show

Flirt4Free 1 year ago

Margaux Fox Private Show

68% HD 2:00 / 25:19

Margaux Fox Private Show

Flirt4Free 4 years ago

Kitty Kunt and her huge she cock

56% HD 0:39 / 22:55

Kitty Kunt and her huge she cock

FapHouse 3 years ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 1 week ago

Three sexy shemale punishers give facials to a dude in bondage

Three sexy shemale punishers give facials to a dude in bondage

aShemaleTube 1 year ago

Sissy guy cums too early and gets punished with rough fucking

Sissy guy cums too early and gets punished with rough fucking

Amazoniansex 6 years ago

French Older SADOMASOCHISM two of three

French Older SADOMASOCHISM two of three

SortPorn 5 years ago

Sophia Loreen Private Show

63% HD 2:00 / 10:58

Sophia Loreen Private Show

Flirt4Free 1 year ago

”Transgender Ryder Monroe bound fisted & screwed hard in AI punishment”

”Transgender Ryder Monroe bound fisted & screwed hard in AI punishment”

Zatube 6 months ago

Their slaves ass needs a little punishment

Their slaves ass needs a little punishment

xHamster 8 months ago

Dianna Campbel Private Show

Dianna Campbel Private Show

Flirt4Free 1 week ago

Hot Shemale Anal Punishment - Homemade

Hot Shemale Anal Punishment - Homemade

Eporner 6 years ago

Ts Punishment

AbTranny 2 years ago

Jhon & Derek & Chris Private Show

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

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

HD 1:01 / 11:02

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

FapHouse 5 days ago

Dominatrix Mistress April - Two Mistresses and a Sissy Whore P1

57% HD 0:39 / 49:01

Dominatrix Mistress April - Two Mistresses and a Sissy Whore P1

FapHouse 1 year ago

Nikki Montero pissing on herself dildo punish dominated by a dude

Nikki Montero pissing on herself dildo punish dominated by a dude

FapHouse 3 years ago

TGIRLSEX.XXX: Jill Pilll's Xmas Hardcore!

TGIRLSEX.XXX: Jill Pilll's Xmas Hardcore!

Fapnado 1 year ago

Brazilian nubiles Facundo And Antonio without a condom

Brazilian nubiles Facundo And Antonio without a condom

GayCK 6 years ago

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

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

Xshemale 2 months ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 1 month ago

”Shemale pornstar Lena Kelly's Kinky Encounter with Sgt Miles”

”Shemale pornstar Lena Kelly's Kinky Encounter with Sgt Miles”

StarWank 1 year ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 2 weeks ago

German Domina punish a crossdresser slave

German Domina punish a crossdresser slave

DrTuber 2 years ago

RUBBER PETS MATCH MAKERS

55% HD 0:10 / 26:24

RUBBER PETS MATCH MAKERS

LoyalFans 1 year ago

Strict tranny mistress punishing guy

Strict tranny mistress punishing guy

aShemaleTube 13 years ago

Punishment Spanking and Reward Sex Dani Sorrento and Trans Dominatrix

Punishment Spanking and Reward Sex Dani Sorrento and Trans Dominatrix

XVideos 3 years ago

”TBabe Tori Easton uses her big dick to inflict pain on my butt”

”TBabe Tori Easton uses her big dick to inflict pain on my butt”

LesbianBliss 1 month ago

Sissy Bimbo Dildo Gauntlet - Dolly's First Attempt

HD 0:10 / 13:11

Sissy Bimbo Dildo Gauntlet - Dolly's First Attempt

LoyalFans 1 year ago

”Hardcore sex in a dungeon with transgender punishment”

”Hardcore sex in a dungeon with transgender punishment”

TransHero 2 years ago

Brihana Boll Private Show

61% HD 2:00 / 25:22

Brihana Boll Private Show

Flirt4Free 8 months ago

Victoria Becker Private Show

62% HD 2:00 / 4:56

Victoria Becker Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

58% HD 2:00 / 13:50

Sophia Loreen Private Show

Flirt4Free 8 months ago

Loud pussy farting & queefing on big cock after discipline

57% HD 1:01 / 10:31

Loud pussy farting & queefing on big cock after discipline

FapHouse 3 years ago

Naughty smoking blonde crossdresser maid has tight pert ass spanked for hot kinky punishment

Naughty smoking blonde crossdresser maid has tight pert ass spanked for hot kinky punishment

aShemaleTube 8 years ago

Crook Gets Punished by Big Dicked Trannies Bruna Ferrari and Yasmin Dornelles

Crook Gets Punished by Big Dicked Trannies Bruna Ferrari and Yasmin Dornelles

xHamster 5 months ago

”T-girl Paradise gets tightened her anus by Jayden Marcos”

”T-girl Paradise gets tightened her anus by Jayden Marcos”

LesbianBliss 3 weeks ago

Trans-Tastic Four

63% HD 0:30 / 1:34:00

Trans-Tastic Four

AEBN 9 years ago

Please Don't Tell Countess!

Please Don't Tell Countess!

xHamster 1 year ago

Sara & Elver Private Show

52% HD 2:00 / 8:25

Sara & Elver Private Show

Flirt4Free 3 months ago

Part 3:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

Part 3:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

xHamster 5 months 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

Cutie Rika Fox gets punished #9 SO HOT! 🔥🔥🔥

Cutie Rika Fox gets punished #9 SO HOT! 🔥🔥🔥

aShemaleTube 1 month ago

MILF Busts Sneaky Kitchen Blowjob

MILF Busts Sneaky Kitchen Blowjob

Some.Porn 6 months ago

Jennifer Jen Private Show

Jennifer Jen 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 1 year ago

[Trans] Spanish 101

Premium 51% VR 32:23

[Trans] Spanish 101

VRPorn 2 years ago

The English education of a cuckold

The English education of a cuckold

xHamster 1 year ago

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

aShemaleTube 10 months 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

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

Fapcat 10 months ago

Four shemale punishers take turns at fucking their male prisoner

Four shemale punishers take turns at fucking their male prisoner

aShemaleTube 1 year ago

Shemale punishes guy

Shemale punishes guy

aShemaleTube 11 years ago

JD Phoenix gets his butthole fucked by brunette tranny Jessy

JD Phoenix gets his butthole fucked by brunette tranny Jessy

Wankoz 1 week ago

”Hardcore sex in a dungeon with shemale punishment”

”Hardcore sex in a dungeon with shemale punishment”

4Wank 1 year ago

Bound For Delivery: Tori Easton and Rodrigo Amor

Premium HD 58:12

Bound For Delivery: Tori Easton and Rodrigo Amor

Kink 3 years ago

Brihana Boll Private Show

HD 2:00 / 33:23

Brihana Boll Private Show

Flirt4Free 6 months ago

Jakes Africa Private Show

Jakes Africa Private Show

Flirt4Free 7 years ago

Trans cutie punished for cumming early

Trans cutie punished for cumming early

ShemaleSin 1 year ago

Trans Girl with Big Puffy Nipples Lactating and Gets her FAT ASS Spanked and Punished

Trans Girl with Big Puffy Nipples Lactating and Gets her FAT ASS Spanked and Punished

xHamster 6 months ago

Sophia Loreen Private Show

58% 4K 2:00 / 4:47

Sophia Loreen Private Show

Flirt4Free 6 months ago

Dustin Hans Private Show

Dustin Hans Private Show

Flirt4Free 2 months ago

You Missed a Spot

You Missed a Spot

xHamster 5 months ago

Sabrina Smiith Private Show

4K 2:00 / 11:06

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Crossdresser mistress use and fuck her slave

Crossdresser mistress use and fuck her slave

Fetishpapa 2 months ago

TS Juliana Belfort and Hex Fetish: Hotel Room Desires (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking - Trans Anal - Trans Sex

61% HD 0:28 / 25:53

TS Juliana Belfort and Hex Fetish: Hotel Room Desires (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking - Trans Anal - Trans Sex

Clips4sale 3 months ago

Mrs. Principal Punishes Student Roleplay ~ Shemale hentai Dominium Chapter two: Carnage

Mrs. Principal Punishes Student Roleplay ~ Shemale hentai Dominium Chapter two: Carnage

SortPorn 4 months ago

I punish my husband because he doesn't lick his

I punish my husband because he doesn't lick his

xHamster 1 year ago

TS Stars Anal Punish Thieves

TS Stars Anal Punish Thieves

BeMyHole 5 months ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

Nuvid 11 months ago

Mistress Makes House Slave Cross-dress, Orders Him to Fap, Watches Him Jerk off His Dick, and Cum Denial with Handjob

HD 0:39 / 32:22

Mistress Makes House Slave Cross-dress, Orders Him to Fap, Watches Him Jerk off His Dick, and Cum Denial with Handjob

FapHouse 8 months ago

Danny & Daniel & Johan & Ivan Private Show

Danny & Daniel & Johan & Ivan Private Show

Flirt4Free 1 year ago

Hot Brand Transsexual Diva Punishes a Guy

aShemaleTube 13 years ago

Blonde Femdom Shemale Anal Pounding

Blonde Femdom Shemale Anal Pounding

TrannyGem 2 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 11 months ago

Three trannies anal punishing guy

Three trannies anal punishing guy

aShemaleTube 8 years ago

Introducing Kinky TS Kitty Kat

46% 1:01 / 14:21

Introducing Kinky TS Kitty Kat

FapHouse 1 year ago

School's In Lesson One: Suck Her Cock

School's In Lesson One: Suck Her Cock

AbTranny 9 years ago

Diapered Pup Vibe Session

Diapered Pup Vibe Session

xHamster 1 year ago

Sophia Loreen Party on Sep 19, 2025 - Part 3

68% 4K 2:00 / 58:36

Sophia Loreen Party on Sep 19, 2025 - Part 3

Flirt4Free 5 months ago

Esmagando a cara da sissy com nossas bundas enormes

Premium HD 12:47

Esmagando a cara da sissy com nossas bundas enormes

XVideosRed 2 years ago

shemale

PornOne 5 years ago

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