Punishment Videos (40,253)

Transsexual Superstars 2

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

Transsexual Superstars 2

AEBN 3 years ago

Liam Jacobson Private Show

Liam Jacobson Private Show

Flirt4Free 3 months ago

Four shemale dominas punish a man and fuck him before facial

Four shemale dominas punish a man and fuck him before facial

xHamster 10 months ago

$Sex and Cum in Elias\' Mouth$ 57% HD 2:00 / 35:38

Sex and Cum in Elias\' Mouth

Flirt4Free 5 months ago

Bellas Balls of Justice 2 - a New Goon Order

51% 1:01 / 43:47

Bellas Balls of Justice 2 - a New Goon Order

FapHouse 4 months ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 2 weeks ago

Burglar Gets Punished by Hung Trannies Yasmin Dornelles n Bruna Ferrari

Burglar Gets Punished by Hung Trannies Yasmin Dornelles n Bruna Ferrari

Tranny.one 5 years ago

Transgender submissive dominated, punished, and pleasured

Transgender submissive dominated, punished, and pleasured

XXXShemalePorn 1 year ago

Trans honey Sunshyne Monroe gets biggest ramrod in her hawt trans butt

Trans honey Sunshyne Monroe gets biggest ramrod in her hawt trans butt

ShemaleSin 1 week ago

Richii Smiith Private Show

Richii Smiith Private Show

Flirt4Free 1 month ago

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

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

LesbianBliss 2 weeks ago

I paid my tailor with a rough ass fuck for measuring my suit

I paid my tailor with a rough ass fuck for measuring my suit

UrGayPorn 1 year ago

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

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

xHamster 11 months ago

Sexy Trans Avery Angel gets fucked by The BBC PUNISHER & Hooly72

Sexy Trans Avery Angel gets fucked by The BBC PUNISHER & Hooly72

aShemaleTube 3 weeks ago

FUTA MISTRESSES PUNISHED BAD SANTA CLAUS WITH DEEP THROAT AND ANAL SEX (SIMS ANIME HENTAI SFM)

FUTA MISTRESSES PUNISHED BAD SANTA CLAUS WITH DEEP THROAT AND ANAL SEX (SIMS ANIME HENTAI SFM)

XVideos 1 year ago

Swallowed bull sperm from a condom KellyAErick

Swallowed bull sperm from a condom KellyAErick

Tranny.one 2 years ago

FTM Puppy Gets Wedgie and Locked in a Cell

FTM Puppy Gets Wedgie and Locked in a Cell

TransTube.tv 9 months ago

Czech MILF dominates a stranger with her strapon KellyAErick

Czech MILF dominates a stranger with her strapon KellyAErick

Tranny.one 3 years ago

”Big Titted tbabe Daisty Taylor gets dominated”

”Big Titted tbabe Daisty Taylor gets dominated”

LesbianBliss 2 days ago

Petite Lanita Enjoys Huge Black Cock

Petite Lanita Enjoys Huge Black Cock

xHamster 7 years ago

Paul Walkers Private Show

HD 2:00 / 11:28

Paul Walkers Private Show

Flirt4Free 7 months ago

She is Dominatrix Ladyboy punishing her slave with pain

She is Dominatrix Ladyboy punishing her slave with pain

Fapnado 5 years ago

Wild Sabrina Members-Only Show

61% HD 2:00 / 29:48

Wild Sabrina Members-Only Show

Flirt4Free 4 years 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 2 months ago

Sexy tgirl smokes and burn her shlong with cigarette cherry an ashes punishment

Sexy tgirl smokes and burn her shlong with cigarette cherry an ashes punishment

ShemaleSin 3 years ago

Jhon & Derek & Chris Private Show - Part 2

66% HD 2:00 / 5:56

Jhon & Derek & Chris Private Show - Part 2

Flirt4Free 3 years ago

2 Strict Mistresses and Trans-submissive! Rough BDSM Using! Arya Grander and Mistress Priest

2 Strict Mistresses and Trans-submissive! Rough BDSM Using! Arya Grander and Mistress Priest

xHamster 1 year ago

Desire Sweet Private Show

HD 2:00 / 12:46

Desire Sweet Private Show

Flirt4Free 1 week ago

Shemale Dating Turns Into Rough Sex

Shemale Dating Turns Into Rough Sex

GayVids 3 months ago

Kiara Lovee Private Show

HD 2:00 / 26:59

Kiara Lovee Private Show

Flirt4Free 1 year ago

Jhordy & Cody & Archie Private Show

66% HD 2:00 / 13:34

Jhordy & Cody & Archie Private Show

Flirt4Free 3 weeks ago

A Perfect Punish - Morgan Bailey And Alexander Gustavo

A Perfect Punish - Morgan Bailey And Alexander Gustavo

PornUse 5 months ago

I want to give you a hot dance, strip and then lick your cock until you cum!!! #STRIP #BLOWJOB

65% HD 2:00 / 4:53

I want to give you a hot dance, strip and then lick your cock until you cum!!! #STRIP #BLOWJOB

Flirt4Free 1 year ago

Ebony Inmate gets Assfucked by Ebony Officer

Ebony Inmate gets Assfucked by Ebony Officer

Ebony8 7 years ago

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

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

Zatube 5 months ago

Monica Farell Private Show

Monica Farell Private Show

Flirt4Free 1 year ago

Gas Mask Domination

Gas Mask Domination

Flirt4Free 4 years ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

Nuvid 11 months ago

Nicco & Patric & Santiago Private Show

59% HD 2:00 / 16:28

Nicco & Patric & Santiago Private Show

Flirt4Free 1 year ago

”Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux”

”Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux”

Rainblow 1 month ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 1 week ago

Tammy Broxx Private Show

Tammy Broxx Private Show

Flirt4Free 3 years ago

Loky & Dionisio Private Show

55% HD 2:00 / 8:00

Loky & Dionisio Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Apr 3, 2025 - Part 17

46% 4K 2:00 / 11:32

Sophia Loreen Party on Apr 3, 2025 - Part 17

Flirt4Free 11 months ago

MESMERIZED - T-Doll Lola Morena PUNISHED By Female dominance Chief Ana Foxxx After Office Dickprint Mishap!

MESMERIZED - T-Doll Lola Morena PUNISHED By Female dominance Chief Ana Foxxx After Office Dickprint Mishap!

KeekAss 1 month ago

Tovez Private Show

67% HD 2:00 / 36:59

Tovez Private Show

Flirt4Free 1 year ago

Transgender Princess Punishers Raunchy up Man Plaything Evelin Rangel , Bruna Castro

Transgender Princess Punishers Raunchy up Man Plaything Evelin Rangel , Bruna Castro

TrannyGem 5 years ago

Bad ladyboy punished for cheating

Bad ladyboy punished for cheating

Pornwhite 2 years ago

TS Jesse Punishes A Cis and Trans Man

TS Jesse Punishes A Cis and Trans Man

BeMyHole 5 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

You can't Touch Yourself without Permission! Veronica Vixen & Gracie Jane for GenderFlux

You can't Touch Yourself without Permission! Veronica Vixen & Gracie Jane for GenderFlux

xHamster 4 months ago

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

BeMyHole 2 years ago

Danny & Bayron & Alonso & Jazar Private Show

Danny & Bayron & Alonso & Jazar Private Show

Flirt4Free 1 year ago

Booty TS Graziella Toledo punishes helpless man with her mighty dick

Booty TS Graziella Toledo punishes helpless man with her mighty dick

Wankoz 3 months ago

Sophia Loreen Private Show

4K 2:00 / 43:56

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Five shemale punishers tie up a dude and fuck him in the ass

Five shemale punishers tie up a dude and fuck him in the ass

xHamster 1 year ago

Sucker for Punishment

HD 1:01 / 14:55

Sucker for Punishment

FapHouse 1 year ago

Boss Punishes Bad Female Employees With A Big Dick

Boss Punishes Bad Female Employees With A Big Dick

11Hentai 2 months ago

TS Jade Venus Dominates Draven Navarro

TS Jade Venus Dominates Draven Navarro

TrannyGem 3 weeks ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 3 weeks ago

”Bitch stuffed with sausages in public”

”Bitch stuffed with sausages in public”

TransHero 2 months ago

Goddess Cherry Punishes My Slutty Holes

64% HD 1:01 / 23:44

Goddess Cherry Punishes My Slutty Holes

FapHouse 2 years ago

Punishment must be

Punishment must be

xHamster 1 week ago

Nasty tranny professor punishes the student as she fucks his ass nice and hard

Nasty tranny professor punishes the student as she fucks his ass nice and hard

BeMyHole 5 years ago

Alice Kizar Private Show

4K 2:00 / 21:04

Alice Kizar Private Show

Flirt4Free 3 weeks ago

Avery Angel gets Punished

Avery Angel gets Punished

aShemaleTube 1 year 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!

58% 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

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 years ago

Jacob Malik Party on Aug 18, 2024

71% HD 2:00 / 1:10:04

Jacob Malik Party on Aug 18, 2024

Flirt4Free 1 year ago

Jenny Wei gets Punished in her last film

Jenny Wei gets Punished in her last film

aShemaleTube 1 year 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

Public Punishment for Naughty Men by Dominant Ladies

Public Punishment for Naughty Men by Dominant Ladies

Jizzberry 2 years ago

Islam Niram Private Show

HD 2:00 / 13:14

Islam Niram Private Show

Flirt4Free 3 years ago

I Was so Overwhelmed That I Had to Take Care of Myself

I Was so Overwhelmed That I Had to Take Care of Myself

FapHouse 3 weeks ago

Trans in latex post climax punishment FULL MOVIE

Trans in latex post climax punishment FULL MOVIE

SortPorn 3 years ago

Submissive ladyboy mouth and ass punished

Submissive ladyboy mouth and ass punished

Sheshaft 2 years ago

When the girlfriend begins nagging...

When the girlfriend begins nagging...

ShemaleSin 4 days ago

Revved Straighty queer bj-service wazoo plow Act

Revved Straighty queer bj-service wazoo plow Act

GayDudesFucking 5 years ago

Shemale Ananda India Smelly Farts On Bitch Face III

Shemale Ananda India Smelly Farts On Bitch Face III

Clips4sale 8 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 week ago

Anal Fingering

Flirt4Free 4 years ago

Orgasm While Camping

Orgasm While Camping

xHamster 7 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation

58% HD 1:01 / 50:47

Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation

FapHouse 9 months ago

Kitty Kunt and her huge she cock

Kitty Kunt and her huge she cock

xHamster 2 weeks ago

Jenny Wei gets Punished

Jenny Wei gets Punished

aShemaleTube 1 year 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

Unhappy wife cheating husband with her transsexual BFF!

Unhappy wife cheating husband with her transsexual BFF!

aShemaleTube 5 years 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 2 months 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

”T-girl Tori Easton uses her huge dick to inflict pain on my booty”

”T-girl Tori Easton uses her huge dick to inflict pain on my booty”

Rainblow 1 month ago

Sophia Loreen Private Show

4K 2:00 / 21:43

Sophia Loreen Private Show

Flirt4Free 3 months ago

Master & Christian & Nicco Private Show

54% HD 2:00 / 9:51

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

Plugged during detention

Plugged during detention

ALOTPorn 3 weeks ago

Sensual Teasing and Pillow Riding

56% HD 2:00 / 7:10

Sensual Teasing and Pillow Riding

Flirt4Free 2 years ago

Desire Sweet Private Show

HD 2:00 / 18:47

Desire Sweet Private Show

Flirt4Free 1 month ago

Hot Dates with TS Gone Wrong

Hot Dates with TS Gone Wrong

GayVids 3 weeks ago

Ninel Croft Private Show

Ninel Croft Private Show

Flirt4Free 1 week ago

Crossdresser punished

Crossdresser punished

aShemaleTube 2 years ago

RachelSexyMaid - No.16 - Chained Slave Dungeon Punishment

RachelSexyMaid - No.16 - Chained Slave Dungeon Punishment

SexTubeSpot 6 years ago

Sophia Loreen Party on Oct 16, 2025 - Part 2

56% 4K 2:00 / 39:30

Sophia Loreen Party on Oct 16, 2025 - Part 2

Flirt4Free 4 months ago

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

Fapcat 9 months ago

Sophia Loreen Party on Mar 2, 2026 - Part 4

4K 2:00 / 39:17

Sophia Loreen Party on Mar 2, 2026 - Part 4

Flirt4Free 6 days ago

William Striptease Sexy Heartbreaker

66% HD 2:00 / 7:52

William Striptease Sexy Heartbreaker

Flirt4Free 4 years ago

Charlie Cano Private Show

61% HD 2:00 / 5:11

Charlie Cano Private Show

Flirt4Free 3 years ago

The BBC Punisher fucks Jenny Wei

The BBC Punisher fucks Jenny Wei

aShemaleTube 2 years ago

Kelly Shore and Jason Miller

Kelly Shore and Jason Miller

AbTranny 9 years ago

squirt... - Part 3

squirt... - Part 3

Flirt4Free 1 week ago

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

HD 0:39 / 16:04

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

FapHouse 2 months ago

Sophia Loreen Private Show

58% 4K 2:00 / 4:47

Sophia Loreen Private Show

Flirt4Free 5 months ago

Jhordy & Maxx Private Show

55% HD 2:00 / 24:57

Jhordy & Maxx Private Show

Flirt4Free 7 months ago

Three brunette and one blonde tranny punisher fuck a stud in bondage

Three brunette and one blonde tranny punisher fuck a stud in bondage

aShemaleTube 1 year ago

Amateur UK crossdressers suck fuck with Grandpa and stepdad CD

Amateur UK crossdressers suck fuck with Grandpa and stepdad CD

Tranny.one 4 years ago

Instruction From the Trainer No 12 Exposure Walk in the Sports Park

HD 0:39 / 24:04

Instruction From the Trainer No 12 Exposure Walk in the Sports Park

FapHouse 1 week ago

TGIRLS HOOKUP: Lying Top Gets Humiliated and Punished!

TGIRLS HOOKUP: Lying Top Gets Humiliated and Punished!

aShemaleTube 3 years ago

Roxanne Roulette Spank Ass Long Masturbate Anal Play

HD 2:00 / 47:43

Roxanne Roulette Spank Ass Long Masturbate Anal Play

Flirt4Free 9 years ago

Charlie And Roxy Spaulding - Lewd 4 - Pleasure And Punishment (full Hd Link Below)

Charlie And Roxy Spaulding - Lewd 4 - Pleasure And Punishment (full Hd Link Below)

AniPorn 2 years ago

Sophia Loreen Private Show

69% HD 2:00 / 5:30

Sophia Loreen Private Show

Flirt4Free 3 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

Nikolly Gaucha punishes his partner

57% HD 0:08 / 0:39

Nikolly Gaucha punishes his partner

FapHouse 1 year ago

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