Punishment Videos (40,089)

Kendall Penny: Bury Your Face Into My Goddess Hole

Premium 75% HD 51:53

Kendall Penny: Bury Your Face Into My Goddess Hole

Kink 5 years ago

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

66% HD 0:39 / 6:30

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

FapHouse 2 weeks ago

Do you deserve to be punished?

Do you deserve to be punished?

FapHouse 2 years ago

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Tranny.one 4 years ago

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

HentaiGem 2 years ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 2 years ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

xHamster 3 weeks ago

Dominant Ts punishes her maid & fucked his bussy hard

Dominant Ts punishes her maid & fucked his bussy hard

aShemaleTube 3 weeks 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 8 months ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

xHamster 1 month ago

Shemale dominating guy

Shemale dominating guy

aShemaleTube 1 month ago

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

xHamster 3 months ago

Veruzca Bigcock punishes guy so hard

Veruzca Bigcock punishes guy so hard

aShemaleTube 3 months ago

Futa Punishes Her Step-slut

58% 1:01 / 19:11

Futa Punishes Her Step-slut

FapHouse 3 weeks ago

Blonde Sissy Gets fucked by The BBC PUNISHER and Facialed full scene

Blonde Sissy Gets fucked by The BBC PUNISHER and Facialed full scene

aShemaleTube 6 days ago

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

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

HQBang 2 years ago

”Punished T-girl Natalie Mars gets ravaged hard by headmaster Dale Savage”

”Punished T-girl Natalie Mars gets ravaged hard by headmaster Dale Savage”

LesbianBliss 2 months ago

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass Clip 2

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass Clip 2

xHamster 2 months ago

Trans Stepsister Femdom

Trans Stepsister Femdom

xHamster 1 year ago

Lovely lad fulfills the TS babe's feet fetish before sucking and riding her thick cock

Lovely lad fulfills the TS babe's feet fetish before sucking and riding her thick cock

Tranny.one 4 years ago

Self Sucking Facial

63% HD 2:00 / 8:19

Self Sucking Facial

Flirt4Free 5 years ago

Roy & Hercules & Jamer Private Show

49% HD 2:00 / 4:09

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

60% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 4 months ago

This cute asian ladyboy needs a real hard punishement

This cute asian ladyboy needs a real hard punishement

Sheshaft 5 years ago

Catheterized Chastity Slave, Become Obligatory a Sissy

HD 1:01 / 18:53

Catheterized Chastity Slave, Become Obligatory a Sissy

FapHouse 1 month ago

PUNISHMENT

aShemaleTube 4 months ago

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

55% 1:01 / 24:48

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

FapHouse 2 months ago

cum show

58% HD 2:00 / 7:48

Flirt4Free 4 years ago

Blazing Hot Domination by The Fire FULL video from

Blazing Hot Domination by The Fire FULL video from

xHamster 1 year ago

Shemale Punishes Her Puffy Nipples Until Lactation

Shemale Punishes Her Puffy Nipples Until Lactation

xHamster 4 months ago

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliat

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliat

PornoXO 1 year ago

Threesome with bella

Threesome with bella

Tranny.one 4 years ago

Red lingeried domina ts punishing her bf

Red lingeried domina ts punishing her bf

aShemaleTube 1 month ago

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Tranny.one 4 years ago

Basic training to become a sissy maid - Locked up and punished

Basic training to become a sissy maid - Locked up and punished

xHamster 3 weeks ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 1 week ago

Luscious Ladies In Latex - A TS Seduction Collection

Luscious Ladies In Latex - A TS Seduction Collection

Tranny.one 4 years ago

DOMMY MOMMY COFFINS PUNISHES SABINA

Premium HD 25:06

DOMMY MOMMY COFFINS PUNISHES SABINA

XVideosRed 3 years ago

Transvestite from hell

Transvestite from hell

xHamster 10 months ago

Damazonia & Rachel Rampage train their sluts to be Orgy party favors

70% HD 0:10 / 26:24

Damazonia & Rachel Rampage train their sluts to be Orgy party favors

LoyalFans 11 months ago

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

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

xHamster 2 months ago

TS domina punishing her festive bf

TS domina punishing her festive bf

Sheshaft 1 week ago

Bukkake #2 the *** 9 T-girls Mass Cumming

48% HD 0:39 / 29:35

Bukkake #2 the *** 9 T-girls Mass Cumming

FapHouse 3 years ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 5 days ago

Crossdresser punishment

Crossdresser punishment

aShemaleTube 4 years 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

Ebony tgirl domina punishes her bf in the kitchen

Ebony tgirl domina punishes her bf in the kitchen

Sheshaft 2 months ago

Ts domination hd Punish my 19 year-old culo and mouth

Ts domination hd Punish my 19 year-old culo and mouth

ProPorn 4 years ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

xHamster 2 years ago

School teenie Practices Painfull Sensation

School teenie Practices Painfull Sensation

GayVids 3 years ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Sunday loving after Saturday torment

Sunday loving after Saturday torment

Tranny.one 4 years ago

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

xHamster 3 months ago

Hercules & Lian & Lance Private Show

51% HD 2:00 / 9:07

Hercules & Lian & Lance Private Show

Flirt4Free 3 years ago

How Badly Do You Want to Play with My Belly and Navel?

64% HD 2:00 / 28:26

How Badly Do You Want to Play with My Belly and Navel?

Flirt4Free 2 years ago

Sophia Loreen Private Show

4K 2:00 / 30:05

Sophia Loreen Private Show

Flirt4Free 8 months ago

TS Mistress Alexa Dominates Muscular

TS Mistress Alexa Dominates Muscular

TransTube.tv 2 weeks ago

Junnior & Archie Private Show

60% HD 2:00 / 12:12

Junnior & Archie Private Show

Flirt4Free 2 weeks ago

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant feat. Anna Hickhiman (trans),Tommy Bravo - Trans n Shemale

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant feat. Anna Hickhiman (trans),Tommy Bravo - Trans n Shemale

xHamster 2 years ago

Elvis & Alfonso & Master Private Show

62% HD 2:00 / 8:58

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Smooth Ass Twerk and Cum - Gape

4K 2:00 / 23:23

Smooth Ass Twerk and Cum - Gape

Flirt4Free 7 years ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 1 week ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

aShemaleTube 5 months ago

Trans in latex post climax punishment FULL MOVIE SCENE

Trans in latex post climax punishment FULL MOVIE SCENE

ShemaleSin 3 years ago

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

xHamster 1 month ago

TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom

TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom

xHamster 2 months ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

xHamster 1 year ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 9 months ago

Wanted: Episode 1

Wanted: Episode 1

Some.Porn 5 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 4 years ago

TS Pussy Hunters 7: Ultimate Sex Fights

65% HD 0:30 / 2:44:00

TS Pussy Hunters 7: Ultimate Sex Fights

AEBN 7 years ago

Hercules & Lance & Lian Miller Private Show

63% HD 2:00 / 8:05

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Pliant a.i. - Hawt Ryder Monroe Is Punished by Cynical Scientist

Pliant a.i. - Hawt Ryder Monroe Is Punished by Cynical Scientist

ShemaleSin 4 weeks ago

Peepers Punishment Is Punished By Shecock - Ts Foxxy

Peepers Punishment Is Punished By Shecock - Ts Foxxy

AbTranny 5 months ago

Alexander & Patric & Alfonso Private Show

42% HD 2:00 / 1:26:38

Alexander & Patric & Alfonso Private Show

Flirt4Free 3 years ago

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

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

FapHouse 1 week ago

Brutus K Flexes and Jerks Off for You

HD 2:00 / 14:29

Brutus K Flexes and Jerks Off for You

Flirt4Free 8 years ago

Ubeer & Paulo Private Show

62% HD 2:00 / 4:46

Ubeer & Paulo Private Show

Flirt4Free 8 months ago

Ubeer & Paulo Private Show

63% HD 2:00 / 8:13

Ubeer & Paulo Private Show

Flirt4Free 8 months ago

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

Flirt4Free 1 year ago

Shemale Samus Soft Tit Slapping with Bbc dildo and Lactating her Puffy Nipples

Shemale Samus Soft Tit Slapping with Bbc dildo and Lactating her Puffy Nipples

xHamster 1 week ago

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

xHamster 1 month ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 6 months ago

Christian & Lian Private Show

53% HD 2:00 / 15:05

Christian & Lian Private Show

Flirt4Free 3 years ago

Patric & Simon & Frederick Private Show

54% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 1 year ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 1 week ago

A slim girl getting punished by her old master in a dungeon

A slim girl getting punished by her old master in a dungeon

xHamster 1 year 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

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

TrannyGem 4 years ago

Curvy inked tranny punishes her best friend

Curvy inked tranny punishes her best friend

Eporner 3 years ago

Archie Blossom Private Show

57% HD 2:00 / 26:57

Archie Blossom Private Show

Flirt4Free 1 week ago

Sophia Loreen Private Show

55% 4K 2:00 / 4:43

Sophia Loreen Private Show

Flirt4Free 1 week 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

Sophia Loreen Party on Jan 14, 2026 - Part 3

4K 2:00 / 32:14

Sophia Loreen Party on Jan 14, 2026 - Part 3

Flirt4Free 1 month ago

Patric & Alexander & Lian Private Show

50% HD 2:00 / 1:09:57

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Lanna & Nefertiti Private Show

57% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

Femboy Asuna maid clumsy and soapy

63% HD 0:39 / 26:17

Femboy Asuna maid clumsy and soapy

FapHouse 3 years ago

Two dominant amateur babes in lingerie punish a horny slave

Two dominant amateur babes in lingerie punish a horny slave

PornLib 5 years ago

Crossdresser Tickled and Vibed in Slut Heels

75% HD 1:01 / 8:37

Crossdresser Tickled and Vibed in Slut Heels

FapHouse 9 months ago

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

FreePorn8 2 months ago

”Blonde babe shocked on the streets”

”Blonde babe shocked on the streets”

TransHero 2 months ago

Sophia Loreen Party on Jan 24, 2026 - Part 7

4K 2:00 / 31:24

Sophia Loreen Party on Jan 24, 2026 - Part 7

Flirt4Free 1 month ago

from cheater to sissy: punishment pegging from futa mommy

55% HD 0:10 / 13:09

from cheater to sissy: punishment pegging from futa mommy

LoyalFans 1 year ago

Cute Femboy Lactating her Tits after Punishing her Nipples with Dildo, Clamps and Vacuum Milking Machine

Cute Femboy Lactating her Tits after Punishing her Nipples with Dildo, Clamps and Vacuum Milking Machine

xHamster 2 weeks ago

Big Dick Trans Mommy Cumming and Milking her Tits

Big Dick Trans Mommy Cumming and Milking her Tits

xHamster 3 months ago

Master & Ithan & Aleex Private Show

41% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 7 months ago

crossdresser bitch

crossdresser bitch

MenGem 4 years ago

Even though we had too much time to keep my body warm

Even though we had too much time to keep my body warm

xHamster 2 weeks ago

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

aShemaleTube 1 week ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

xHamster 4 months ago

Richii Smiith Private Show

Richii Smiith Private Show

Flirt4Free 1 month ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Rika Fox gets punished #8 full 23 min vid out now! Subscribe and enjoy 😉

Rika Fox gets punished #8 full 23 min vid out now! Subscribe and enjoy 😉

aShemaleTube 8 months ago

Goddess Cherry Punishes My Slutty Holes

60% HD 0:39 / 23:44

Goddess Cherry Punishes My Slutty Holes

FapHouse 2 years ago

Sophia Loreen Party on Sep 10, 2025 - Part 2

54% 4K 2:00 / 7:22

Sophia Loreen Party on Sep 10, 2025 - Part 2

Flirt4Free 5 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

BeMyHole 5 years ago

A Private Punishment

A Private Punishment

Tranny.one 4 years ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 1 week ago

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