Punishment (1,767)

Professor's Naughty Lesson – Misty Addams & Naejae Onyxx Dominate the Dean's Office (SD 720p WMV)

HD 0:28 / 23:20

Professor's Naughty Lesson – Misty Addams & Naejae Onyxx Dominate the Dean's Office (SD 720p WMV)

Clips4sale 7 months ago

Stepson Caught gooning gets pegged and fisted by London River (2024 AVN Domme of the year)

66% HD 0:10 / 21:18

Stepson Caught gooning gets pegged and fisted by London River (2024 AVN Domme of the year)

Clips4sale 2 years ago

TGirl Threesome Fun

Premium 55% 20:22

TGirl Threesome Fun

APClips 1 year ago

EXTREME KINK BONDAGE TRAINING - BDSM Punishment, Bondage and Restraints, Crossdresser Bondage, Sissy Bondage Erotic Mind Fuck

EXTREME KINK BONDAGE TRAINING - BDSM Punishment, Bondage and Restraints, Crossdresser Bondage, Sissy Bondage Erotic Mind Fuck

Clips4sale 1 year ago

Wheel of Fortune

Wheel of Fortune

Clips4sale 1 year ago

Punishing the Cupcake Thief - A trans anal scene featuring: strap-on, BBW with trans, pegging, lesbian domination, and feederism - 1080 MP4

65% HD 0:29 / 25:39

Punishing the Cupcake Thief - A trans anal scene featuring: strap-on, BBW with trans, pegging, lesbian domination, and feederism - 1080 MP4

Clips4sale 2 years ago

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

59% 0:30 / 16:29

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

Clips4sale 5 months ago

Busted Watching Porn at Work Boss Punishes Bad Employee with Her Own Cock

65% 0:11 / 38:52

Busted Watching Porn at Work Boss Punishes Bad Employee with Her Own Cock

Clips4sale 2 years ago

Pink SissPiggy Training

Pink SissPiggy Training

Clips4sale 3 years ago

Bullwhipped For Smoking (WMV HD)

Bullwhipped For Smoking (WMV HD)

Clips4sale 7 months ago

The Struggle Is Real (720p)

HD 0:30 / 19:35

The Struggle Is Real (720p)

Clips4sale 7 months ago

Sexual Punishment From Futa Principal - Ft Imilia Audley

Sexual Punishment From Futa Principal - Ft Imilia Audley

Clips4sale 5 months ago

CAUGHT & FEMINIZED BY PATRIARCH

CAUGHT & FEMINIZED BY PATRIARCH

Clips4sale 6 months ago

The Governess shows Auntie Bea just how it’s done. @TFrillyknicks

The Governess shows Auntie Bea just how it’s done. @TFrillyknicks

LoyalFans 5 months ago

Pretty in Pink, Punished in Full

HD 0:10 / 20:20

Pretty in Pink, Punished in Full

LoyalFans 3 months ago

Choking, Impact Play and Teat Punishment for Lascivious Sub! - Full Fansly Trickle

Choking, Impact Play and Teat Punishment for Lascivious Sub! - Full Fansly Trickle

ShemaleSin 1 month ago

hot girl spanking the ass clip 01 of 03

hot girl spanking the ass clip 01 of 03

Clips4sale 2 years ago

Bad Girl Punished 3 mp4

Bad Girl Punished 3 mp4

Clips4sale 2 years ago

Beating your Balls Locktober Day 2

4K 0:30 / 12:05

Beating your Balls Locktober Day 2

Clips4sale 1 year ago

Punishing you for looking at trans porn

Punishing you for looking at trans porn

LoyalFans 2 years ago

Scarlett Kage catches Joey jerking off in her panties: FULL video! sissification, caught jerking off, stepmom fantasy, role play, cross dressing, spanking, anal play, pegging, jerking, dirty talk MP4

Scarlett Kage catches Joey jerking off in her panties: FULL video! sissification, caught jerking off, stepmom fantasy, role play, cross dressing, spanking, anal play, pegging, jerking, dirty talk MP4

Clips4sale 2 years ago

A good slave to lick our feet - clip 02 of 03

A good slave to lick our feet - clip 02 of 03

Clips4sale 2 years ago

The cross dresser is punished

56% 0:11 / 2:13

The cross dresser is punished

Clips4sale 1 year ago

futa step-sis makes you her slave - punishment painal, slapping, spitting, and facefucking

HD 0:10 / 21:03

futa step-sis makes you her slave - punishment painal, slapping, spitting, and facefucking

LoyalFans 1 year ago

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Premium HD 3:14:26

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Clips4sale 1 year ago

Spank my Hole

77% 0:57 / 16:08

Clips4sale 2 years ago

Beautiful women and crossdresser 20:The Punishment of the Stunning Black Stocking Queen

Beautiful women and crossdresser 20:The Punishment of the Stunning Black Stocking Queen

Clips4sale 1 month ago

Completely compromised

66% HD 0:10 / 19:21

Completely compromised

LoyalFans 1 month ago

Permanent Punisher

Permanent Punisher

Clips4sale 4 months ago

Patricia the crossdresser gets into all sorts of trouble

Patricia the crossdresser gets into all sorts of trouble

LoyalFans 3 months ago

I have a lot of fun with you

I have a lot of fun with you

LoyalFans 2 months ago

Sissy Shelby Torture

Sissy Shelby Torture

ShemaleSin 3 months ago

Facefucked by Krampus - Jaq Quicksilver Punishes You With POV Demon Cock and Big Clit Facefucking - FtM, trans, femdom, holiday, strapon - 720p mp4

Facefucked by Krampus - Jaq Quicksilver Punishes You With POV Demon Cock and Big Clit Facefucking - FtM, trans, femdom, holiday, strapon - 720p mp4

Clips4sale 3 months ago

I like red ass (wmv)

HD 0:16 / 13:07

I like red ass (wmv)

Clips4sale 4 years ago

Foot Tease & POV Ball Busting (HD1080 WMV)

Foot Tease & POV Ball Busting (HD1080 WMV)

Clips4sale 3 years ago

Anastasia Rose Spanked, Flogged and Cropped (HD1080 MP4)

Anastasia Rose Spanked, Flogged and Cropped (HD1080 MP4)

Clips4sale 3 years ago

Cucked & Punished by Horny Nuns - TRANS LESBIAN Nuns Deliver HUMILIATION and FEMDOM POV CUCKOLDING with Cherry Mavrick & Sydney Screams - HD 1080 MP4

HD 0:25 / 20:08

Cucked & Punished by Horny Nuns - TRANS LESBIAN Nuns Deliver HUMILIATION and FEMDOM POV CUCKOLDING with Cherry Mavrick & Sydney Screams - HD 1080 MP4

Clips4sale 3 years ago

Goddess Lohan and Inara - Punish slave maid

Goddess Lohan and Inara - Punish slave maid

Clips4sale 3 years ago

Sequel: Futanari Step-sister Punishes You For Spying - Ft Imilia Audley

Sequel: Futanari Step-sister Punishes You For Spying - Ft Imilia Audley

Clips4sale 1 month ago

PUNISHING MY MAID WITH LONG STINKY FARTS - BY BABI VENTURA - CLIP 1 IN FULL HD

Premium HD 5:00

PUNISHING MY MAID WITH LONG STINKY FARTS - BY BABI VENTURA - CLIP 1 IN FULL HD

Clips4sale 3 years ago

Shemale Maylla Mendes Cruel Punishment VI

Shemale Maylla Mendes Cruel Punishment VI

Clips4sale 3 years ago

Elf On A Shelf Part 2 Pervert Payback

Elf On A Shelf Part 2 Pervert Payback

Clips4sale 3 years ago

FARTING ON THE IDIOT SLAVE'S RIDICULOUS DICK - BY MEGERA AND ISABELITA - FULL VERSION IN FULL HD

HD 1:00 / 24:11

FARTING ON THE IDIOT SLAVE'S RIDICULOUS DICK - BY MEGERA AND ISABELITA - FULL VERSION IN FULL HD

Clips4sale 3 years ago

futa step-sis makes you her slave - punishment painal, slapping, spitting - SD - wmv

futa step-sis makes you her slave - punishment painal, slapping, spitting - SD - wmv

Clips4sale 3 years ago

Sissy punished for stealing Mistress' clothes

Sissy punished for stealing Mistress' clothes

Clips4sale 2 years ago

Sissy maid exposed-fantasy - Spanked in front of my mean friends

Sissy maid exposed-fantasy - Spanked in front of my mean friends

Clips4sale 2 years ago

French bitch gets punished - Episode 1 mp4

HD 1:00 / 30:22

French bitch gets punished - Episode 1 mp4

Clips4sale 1 year ago

Kelly Shore & Jason Miller

66% 0:11 / 43:23

Kelly Shore & Jason Miller

C4S 2 years ago

Wedgies and Spanking Self Punishment (HD1080 MP4)

Wedgies and Spanking Self Punishment (HD1080 MP4)

Clips4sale 2 years ago

Wedgies and Spanking Self Punishment (STANDARD MP4)

Wedgies and Spanking Self Punishment (STANDARD MP4)

Clips4sale 2 years ago

Transsexual dominating his lover in chastity

Transsexual dominating his lover in chastity

ShemaleSin 4 years ago

Window Cleaners Surprise Part 7 StrapOn Punishment

Window Cleaners Surprise Part 7 StrapOn Punishment

Clips4sale 4 years ago

No escape from straitjacket

No escape from straitjacket

Clips4sale 4 years ago

Latex TGirl slave ass whipping (720p)

HD 0:11 / 11:09

Latex TGirl slave ass whipping (720p)

Clips4sale 3 years ago

Cunt Busting My Slave Girl Anastasia Rose (STANDARD MP4)

Cunt Busting My Slave Girl Anastasia Rose (STANDARD MP4)

Clips4sale 3 years ago

Natalie Luxxurious Tries To Teach Me How To Burp (STANDARD MP4)

Natalie Luxxurious Tries To Teach Me How To Burp (STANDARD MP4)

Clips4sale 3 years ago

PEGGING NURSES

68% HD 0:30 / 9:46

Clips4sale 3 years ago

SHEMALE DOMINATION - 09 - FULL VERSION - WMV

HD 0:11 / 22:34

SHEMALE DOMINATION - 09 - FULL VERSION - WMV

Clips4sale 3 years ago

Strap On GF and CEI Punishment

57% HD 0:11 / 11:59

Strap On GF and CEI Punishment

Clips4sale 4 years ago

Our Personal Foot Slave I

Our Personal Foot Slave I

Clips4sale 4 years ago

Training My Sissy

46% HD 0:15 / 8:49

Training My Sissy

Clips4sale 4 years ago

Lets spank your ass

HD 0:10 / 11:46

Lets spank your ass

Clips4sale 4 years ago

I Will Rub My Ass In Your Face Until I Cum! - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 33 MINUTES FOR US$ 19,99!

HD 0:30 / 33:23

I Will Rub My Ass In Your Face Until I Cum! - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 33 MINUTES FOR US$ 19,99!

Clips4sale 1 year ago

Pussy punishment in suspension bondage

Pussy punishment in suspension bondage

APClips 1 year ago

AUDIO: Cucked: futa boss fucks your GF while you listen on work call

AUDIO: Cucked: futa boss fucks your GF while you listen on work call

APClips 1 year ago

SHEMALE DOMINATION - 67 - YANCA COSTA & SAFIRA MEL - CLIP 1 OF 5 - WMV

SHEMALE DOMINATION - 67 - YANCA COSTA & SAFIRA MEL - CLIP 1 OF 5 - WMV

Clips4sale 1 year ago

Shemale Ana Carolina First Farting Experience III

Shemale Ana Carolina First Farting Experience III

Clips4sale 10 months ago

Pinky Tries To Earn His Release Thru CBT (720p)

68% HD 0:30 / 12:48

Pinky Tries To Earn His Release Thru CBT (720p)

Clips4sale 9 months ago

You will be trampled and humiliated by cruel dick-girl, fc327x 1080p

66% HD 0:22 / 10:22

You will be trampled and humiliated by cruel dick-girl, fc327x 1080p

Clips4sale 11 months ago

TWOFOLD: Two Taboo Futas

Premium HD 30:40

TWOFOLD: Two Taboo Futas

Clips4sale 1 year ago

Anal Punishment for Christmas

Anal Punishment for Christmas

aShemaleTube 1 year ago

The maid betrayed her boss and now she will be punished with farts - BY NATASHA CRUEL AND PENELOPE PINK - FULL VERSION IN FULL HD

HD 0:59 / 25:27

The maid betrayed her boss and now she will be punished with farts - BY NATASHA CRUEL AND PENELOPE PINK - FULL VERSION IN FULL HD

Clips4sale 3 years ago

FARTING WITH MY BEST FRIEND ON MY SLAVE'S HORRIBLE DICK - BY BABI VENTURA AND BRUNA PAES - FULL VERSION IN FULL HD

HD 1:00 / 21:14

FARTING WITH MY BEST FRIEND ON MY SLAVE'S HORRIBLE DICK - BY BABI VENTURA AND BRUNA PAES - FULL VERSION IN FULL HD

Clips4sale 3 years ago

FARTING WITH MY BEST FRIEND ON MY SLAVE'S HORRIBLE DICK - BY BABI VENTURA AND BRUNA PAES - CLIP 1 IN FULL HD

Premium HD 5:00

FARTING WITH MY BEST FRIEND ON MY SLAVE'S HORRIBLE DICK - BY BABI VENTURA AND BRUNA PAES - CLIP 1 IN FULL HD

Clips4sale 3 years ago

POWERFULL FARTS IN YOUR UGLY DICK - BY THAY FLORES AND RAVE GIRL - CLIP 1 IN FULL HD

Premium HD 5:00

POWERFULL FARTS IN YOUR UGLY DICK - BY THAY FLORES AND RAVE GIRL - CLIP 1 IN FULL HD

Clips4sale 3 years ago

SHEMALE DOMINATION - 15 - CLIP 3 OF 4 - WMV

SHEMALE DOMINATION - 15 - CLIP 3 OF 4 - WMV

Clips4sale 2 years ago

SHEMALE DOMINATION - 15 - CLIP 1 OF 4 - MP4

SHEMALE DOMINATION - 15 - CLIP 1 OF 4 - MP4

Clips4sale 2 years ago

My big sissy bitch get's punished

My big sissy bitch get's punished

Clips4sale 2 years ago

PUNISHING MY MAID WITH LONG STINKY FARTS - BY BABI VENTURA - FULL VERSION IN FULL HD

HD 0:59 / 20:58

PUNISHING MY MAID WITH LONG STINKY FARTS - BY BABI VENTURA - FULL VERSION IN FULL HD

Clips4sale 3 years ago

JessicaXD - Rubber Doll out of her chasity

JessicaXD - Rubber Doll out of her chasity

xHamster 3 years ago

FARTING ON THE IDIOT SLAVE'S RIDICULOUS DICK - BY MEGERA AND ISABELITA - CLIP 1 IN FULL HD

Premium HD 5:00

FARTING ON THE IDIOT SLAVE'S RIDICULOUS DICK - BY MEGERA AND ISABELITA - CLIP 1 IN FULL HD

Clips4sale 3 years ago

PUNISHING POOR JACK WITH DUAL FART BOMBS - BY THAY FLORES AND RAVE GIRL - CLIP 1 IN FULL HD

Premium HD 5:00

PUNISHING POOR JACK WITH DUAL FART BOMBS - BY THAY FLORES AND RAVE GIRL - CLIP 1 IN FULL HD

Clips4sale 3 years ago

Tied and Spanked submissive Femboy at forest

Tied and Spanked submissive Femboy at forest

xHamster 3 years ago

The Locker Room Take Down

The Locker Room Take Down

C4S 2 years ago

Petite Pinup's Pussy Punishment Director's Cut

HD 0:29 / 48:08

Petite Pinup's Pussy Punishment Director's Cut

Clips4sale 2 years ago

Punished by Mistress (Full)

Punished by Mistress (Full)

LoyalFans 2 years ago

AlexxaVonHell defiles the ass of two boarding school lovers

AlexxaVonHell defiles the ass of two boarding school lovers

Clips4sale 1 year ago

Hunted and Caged Part 10 - Prisoner to sissy Transformation 4 with Anna List

4K 0:47 / 10:18

Hunted and Caged Part 10 - Prisoner to sissy Transformation 4 with Anna List

Clips4sale 2 years ago

Her Prisoner Part 24 - Sissy Training VII

59% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 2 years ago

asscheek fucking turns into futa domination pov

asscheek fucking turns into futa domination pov

Clips4sale 2 years ago

Cunt Busting Stefania Mafra (HD1080 MP4)

Cunt Busting Stefania Mafra (HD1080 MP4)

Clips4sale 2 years ago

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 2 AND PART 3

HD 0:10 / 25:17

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 2 AND PART 3

LoyalFans 2 years ago

mistress claus's mean punishment pegging for naughty boys - HD - wmv

HD 0:29 / 12:03

mistress claus's mean punishment pegging for naughty boys - HD - wmv

Clips4sale 3 years ago

Cross & Dressed - MP4 - 1920

Cross & Dressed - MP4 - 1920

Clips4sale 3 years ago

FEEL MY STINKY FARTS DEEPLY RIDICULOUS OGRE - BY KIMBERLY SATINA - CLIP 3 IN FULL HD

Premium HD 5:00

FEEL MY STINKY FARTS DEEPLY RIDICULOUS OGRE - BY KIMBERLY SATINA - CLIP 3 IN FULL HD

Clips4sale 3 years ago

mean coworker pegs you for embarrassing her at work - HD - wmv

mean coworker pegs you for embarrassing her at work - HD - wmv

Clips4sale 3 years ago

Bound Tickle Play With Trans Beauties Mary Max & Nikola Ophan - PART 2 (HD 1080p MP4)

Premium HD 11:07

Bound Tickle Play With Trans Beauties Mary Max & Nikola Ophan - PART 2 (HD 1080p MP4)

Clips4sale 2 years ago

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 2

HD 0:10 / 10:09

CANDY THIEF PUNISHMENT BY PEGGING AND GELDING - PART 2

LoyalFans 2 years ago

Sissy Maid Training Stage 1 (WMV)

Sissy Maid Training Stage 1 (WMV)

Clips4sale 2 years ago

Guy Transformed into Hot Babe as Punishment by Female Roommate

Guy Transformed into Hot Babe as Punishment by Female Roommate

xHamster 2 years ago

Punishing and Fucking Futa Tatsumaki

Punishing and Fucking Futa Tatsumaki

APClips 1 year ago

Futa Punishes You For No Nut November - Ft Imilia Audley

HD 0:20 / 11:12

Futa Punishes You For No Nut November - Ft Imilia Audley

Clips4sale 1 year ago

Suffer With Shemale Bianca Rosa Dirty Farts III

58% HD 0:30 / 5:10

Suffer With Shemale Bianca Rosa Dirty Farts III

Clips4sale 1 year ago

Jasmine Dlight finds Valentina Roasa's Pussy, breaks it and then gets heavily pegged as a punishment

Jasmine Dlight finds Valentina Roasa's Pussy, breaks it and then gets heavily pegged as a punishment

Clips4sale 1 year ago

Vertical Hogtie in Vinyl

4K 0:30 / 10:51

Vertical Hogtie in Vinyl

Clips4sale 11 months ago

Crossdressing Slave Orally and Anally Submitted - Full Version

HD 0:30 / 21:33

Crossdressing Slave Orally and Anally Submitted - Full Version

Clips4sale 1 year ago

Stacy sadistic punishes naughty kitten!

Stacy sadistic punishes naughty kitten!

APClips 1 year ago

Cheap Slut Part 3 Rimming Whore

Premium 49% 9:18

Cheap Slut Part 3 Rimming Whore

APClips 1 year ago

Padded Punishment w/ Mercy & River

Padded Punishment w/ Mercy & River

APClips 1 year ago

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the wel deserved Punishment, and cums over her

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the wel deserved Punishment, and cums over her

APClips 1 year ago

futa mommy pegs you - punished for stealing panties

futa mommy pegs you - punished for stealing panties

APClips 1 year ago

Dominating Kyla Keys Spanking and Bondage Fuck Submissive MILF Gets Punished and Rough Fucked by Trans Domme Creampie

Dominating Kyla Keys Spanking and Bondage Fuck Submissive MILF Gets Punished and Rough Fucked by Trans Domme Creampie

APClips 1 year ago

You're going to futa jail MP4

HD 0:26 / 11:00

You're going to futa jail MP4

Clips4sale 1 year ago

Your Sissy Uniform - Classic French Maid

Your Sissy Uniform - Classic French Maid

Clips4sale 1 year ago

Epic moment from "Hot Shemale Made My Wife Cum & Orgasm Better Then I Can"

Epic moment from "Hot Shemale Made My Wife Cum & Orgasm Better Then I Can"

xHamster 1 year ago

A Bet's A Bet w/ Nikki Venus

A Bet's A Bet w/ Nikki Venus

APClips 1 year ago

Giant Futa Humiliation

HD 0:50 / 18:25

Giant Futa Humiliation

Clips4sale 11 months ago

Tiny Bimbo Transformation: Giantess Ravens Futa Pocket Pet

64% HD 0:10 / 21:03

Tiny Bimbo Transformation: Giantess Ravens Futa Pocket Pet

LoyalFans 1 year ago

Crossdressing Stepsons need to be punished in chastity and humiliated by their Step Mother (short)

Crossdressing Stepsons need to be punished in chastity and humiliated by their Step Mother (short)

Clips4sale 1 year ago

Sasha Tengus French class

Sasha Tengus French class

Clips4sale 1 year ago

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