Punished Videos (35,426)

Cougar TS mother in law punishing lazy teeanger

Cougar TS mother in law punishing lazy teeanger

4Wank 1 year ago

Crossdresser punishment

Crossdresser punishment

Eporner 3 years ago

Master Turns Tranny Slave into Cock Sucking Cum Slut after Ass Punishment

Master Turns Tranny Slave into Cock Sucking Cum Slut after Ass Punishment

TrannyGem 6 years ago

Wild Sabrina Private Show

55% HD 2:00 / 8:19

Wild Sabrina Private Show

Flirt4Free 3 years ago

Award Winning Roleplay

52% HD 2:00 / 47:07

Award Winning Roleplay

Flirt4Free 4 weeks ago

Dasha Sento Private Show

4K 2:00 / 19:49

Dasha Sento Private Show

Flirt4Free 1 week ago

Sophia Loreen Party on May 13, 2025 - Part 2

48% 4K 2:00 / 32:47

Sophia Loreen Party on May 13, 2025 - Part 2

Flirt4Free 3 months ago

Sissy Maid Icy Hot Wooden Pony Punishment 2

Sissy Maid Icy Hot Wooden Pony Punishment 2

xHamster 2 years ago

Liam & Jacob Private Show

68% HD 2:00 / 5:51

Liam & Jacob Private Show

Flirt4Free 11 months ago

Nasty tranny cop Aylla fucks guy

Nasty tranny cop Aylla fucks guy

xHamster 11 months ago

Kinky Whore in Her New Hood

62% HD 1:01 / 31:25

Kinky Whore in Her New Hood

FapHouse 5 months ago

TS Boss Punishes Employee!

TS Boss Punishes Employee!

aShemaleTube 6 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

TSDOMME: Str8 Chap Fastened and Punished

TSDOMME: Str8 Chap Fastened and Punished

ShemaleSin 6 months ago

Amateur Tranny Punishes A Submissive Guy

Amateur Tranny Punishes A Submissive Guy

BeMyHole 2 years ago

Easy to dress fake girl sakura experiences various gameplay of Punishment rack

54% 0:16 / 13:14

Easy to dress fake girl sakura experiences various gameplay of Punishment rack

C4S 8 months ago

Mara Nova and Sydney Farron In Punishment by Principal

Mara Nova and Sydney Farron In Punishment by Principal

Tranny.one 5 years ago

Shemale mechanic Miss Jane Starr anal fucks and creampies busty babe Penny Barber

Shemale mechanic Miss Jane Starr anal fucks and creampies busty babe Penny Barber

Eporner 1 day ago

Sophia Loreen Party on May 15, 2025 - Part 2

64% 4K 2:00 / 22:37

Sophia Loreen Party on May 15, 2025 - Part 2

Flirt4Free 3 months ago

Sophia Loreen Party on Aug 16, 2025 - Part 3

HD 2:00 / 20:16

Sophia Loreen Party on Aug 16, 2025 - Part 3

Flirt4Free 1 week ago

Raw and Uncensored Good Tranny Takes on the Punishment

Raw and Uncensored Good Tranny Takes on the Punishment

Love4Porn 2 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 4 days ago

Punished for wearing wifes panties

Punished for wearing wifes panties

xHamster 2 years ago

Sissy Bimbo Maid Gets Punished

HD 0:10 / 29:34

Sissy Bimbo Maid Gets Punished

Clips4sale 3 years ago

Big Tits Submissive Russian Slut Returns For Ass Eating & Rough Sex

Big Tits Submissive Russian Slut Returns For Ass Eating & Rough Sex

FapCat 4 months ago

Transgender Natalie Mars fisted & tightened by MOMMY Penny Barber

Transgender Natalie Mars fisted & tightened by MOMMY Penny Barber

Rainblow 4 months ago

Slim Domina Pegs a Sissy Femboy For Wearing Her Panties And Milks His Cock Till He Drains His Balls

Slim Domina Pegs a Sissy Femboy For Wearing Her Panties And Milks His Cock Till He Drains His Balls

XGroovy 1 year ago

Submit, It Will Go A Lot Smoother: Ts Natassia Dreams Is BACK

66% 0:11 / 28:39

Submit, It Will Go A Lot Smoother: Ts Natassia Dreams Is BACK

C4S 2 years ago

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

53% HD 2:00 / 4:52

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

Flirt4Free 3 years ago

Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux

Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux

ThePornstar 2 months ago

Transgender Ryder Monroe bound fisted & screwed hard in AI punishment

Transgender Ryder Monroe bound fisted & screwed hard in AI punishment

ThePornstar 2 months ago

Big Dick Trans Police Woman Punishes You - Officer Jessica Bloom

HD 1:01 / 21:10

Big Dick Trans Police Woman Punishes You - Officer Jessica Bloom

FapHouse 4 days ago

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

TubeOn 1 year ago

Sandy Nell Private Show

4K 2:00 / 24:29

Sandy Nell Private Show

Flirt4Free 1 week ago

781361418434785280.mp4

HD 1:01 / 13:05

781361418434785280.mp4

FapHouse 1 week ago

Leela's Thanksgiving Day Dinner

63% HD 1:01 / 21:36

Leela's Thanksgiving Day Dinner

FapHouse 1 year ago

"LA ZIA E IL NIPOTE MINI PENE" --- "THE AUNT AND THE SMALL PENIS"

"LA ZIA E IL NIPOTE MINI PENE" --- "THE AUNT AND THE SMALL PENIS"

Clips4sale 1 year ago

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

Pervclips 3 months ago

Getting Punished in His Office for Failing His Course. Bless That Dick

Getting Punished in His Office for Failing His Course. Bless That Dick

xHamster 8 months ago

Bound thieves punished by rough shemale domme

Bound thieves punished by rough shemale domme

XXXShake 3 years ago

Sniffing Shemale Marcela Dimov Dirty Farts III

Sniffing Shemale Marcela Dimov Dirty Farts III

Clips4sale 1 year ago

Caning and choking Kitsy

Caning and choking Kitsy

xHamster 3 years ago

Trixxy Blowbang

64% 0:10 / 22:52

Trixxy Blowbang

APClips 6 months ago

Hey! I Want You to Let Yourself Be Seduced.

Hey! I Want You to Let Yourself Be Seduced.

Flirt4Free 11 months ago

Four femdom shemales punish and anal fuck submissive males

Four femdom shemales punish and anal fuck submissive males

Eporner 1 month 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 4 months ago

Naughty shemale Ella Hollywood gets hardcore punished by Dom Sebastian Keys

Naughty shemale Ella Hollywood gets hardcore punished by Dom Sebastian Keys

aShemaleTube 3 weeks ago

Sophia Loreen Members-Only Show - Part 2

HD 2:00 / 1:13:36

Sophia Loreen Members-Only Show - Part 2

Flirt4Free 1 week ago

Fucked Behind Bars

Fucked Behind Bars

Zatube 9 months ago

The Teacher is Paddled - WMV 720x480

68% 4K 0:23 / 20:06

The Teacher is Paddled - WMV 720x480

Clips4sale 4 years ago

Four brunette shemales in black leather boots fuck their

Four brunette shemales in black leather boots fuck their

xHamster 5 months ago

Jaquline Braxton Catches Pervy Peeping Tom and Seduces him with her Hard Cock and Luscious Ass.

67% HD 1:26 / 37:33

Jaquline Braxton Catches Pervy Peeping Tom and Seduces him with her Hard Cock and Luscious Ass.

KinkTrans 9 years ago

Master Spanks, Toys, Punishes, and Fucks Sissy Slave Girl

Master Spanks, Toys, Punishes, and Fucks Sissy Slave Girl

TrannyGem 4 years ago

Sophia Loreen Private Show

HD 2:00 / 16:24

Sophia Loreen Private Show

Flirt4Free 1 month ago

Bondage hentai bride with bigtits gets punishment

Bondage hentai bride with bigtits gets punishment

VikiPorn 12 years ago

Hottie lesbo Skin Diamond gets slit punished

Hottie lesbo Skin Diamond gets slit punished

4KPorn 4 years ago

Mint & Melissa Private Show

69% HD 2:00 / 4:54

Mint & Melissa Private Show

Flirt4Free 2 years ago

strict mistress with huge strapon and big cock catch and punish her robber

strict mistress with huge strapon and big cock catch and punish her robber

aShemaleTube 3 months ago

Military Sluts Aphrodite Adams and Rachael Belle are Punished by Drill Sargent Cherry Mavrik

Military Sluts Aphrodite Adams and Rachael Belle are Punished by Drill Sargent Cherry Mavrik

4KPorn 1 year ago

The Mermaid: The Siren of Seduction

65% 0:11 / 33:57

The Mermaid: The Siren of Seduction

C4S 2 years ago

Satisfying Kasey Kei submits to King Noire for rough assfucking punishment

Satisfying Kasey Kei submits to King Noire for rough assfucking punishment

HQBang 4 months ago

Sexy FTM Punishes Tits With Clothespins

55% 0:11 / 3:46

Sexy FTM Punishes Tits With Clothespins

C4S 2 years ago

Spanked and Sucked In Suspenders 720

49% HD 0:37 / 10:39

Spanked and Sucked In Suspenders 720

Clips4sale 8 months ago

Izzi Private Show

Izzi Private Show

Flirt4Free 4 weeks ago

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

xHamster 3 years ago

Tiny Bimbo Transformation: Giantess Ravens Futa Pocket Pet - Giantess, Bimbofication, Futa

40% 4K 0:29 / 21:02

Tiny Bimbo Transformation: Giantess Ravens Futa Pocket Pet - Giantess, Bimbofication, Futa

Clips4sale 6 months ago

Gemma spanking and fucking her slut

Gemma spanking and fucking her slut

Tranny.one 3 years ago

Fuckmachine torture

Fuckmachine torture

xHamster 2 years ago

Luna Florez Private Show

68% 4K 2:00 / 19:21

Luna Florez Private Show

Flirt4Free 3 months ago

Adriana Rodrigues in black leather boots punishes her

Adriana Rodrigues in black leather boots punishes her

xHamster 1 year ago

Barbara Perez - The Nurse Knows Best

Barbara Perez - The Nurse Knows Best

Tranny.one 4 years ago

Charlie Cano Private Show

66% HD 2:00 / 7:16

Charlie Cano Private Show

Flirt4Free 2 years ago

Punished for Perfection

Punished for Perfection

Hoes.tube 4 months ago

African boy gets fucked by a 2 big black dicks raw

African boy gets fucked by a 2 big black dicks raw

Tranny.one 3 years ago

Christian & Nicco & Elvis Private Show

HD 2:00 / 17:06

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

xHamster 1 year ago

Patric & Oliver Private Show

66% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 2 years ago

Foot Tease & POV Ball Busting (HD1080 MP4)

57% 0:11 / 11:25

Foot Tease & POV Ball Busting (HD1080 MP4)

Clips4sale 3 years ago

Group sex with four brunette shemales dominating a dude

Group sex with four brunette shemales dominating a dude

xHamster 5 months ago

Piss as punishment

49% HD 0:13 / 4:18

Piss as punishment

Clips4sale 3 years ago

Mint & Melissa Private Show

66% HD 2:00 / 43:06

Mint & Melissa Private Show

Flirt4Free 2 years ago

Spank Bank

Tranny.one 3 years ago

Church Girl Takes Control of Older Man

4K 0:29 / 13:35

Church Girl Takes Control of Older Man

Clips4sale 1 year ago

Shemale jade punishes boy friend

Shemale jade punishes boy friend

Fetishpapa 3 years ago

fat ass shaking, girl moaning & groaning. we also spread anal & hairy vagina so we can look there. daddy punishes his young & beautiful girl. spanking her big white ass very hard.

64% HD 0:28 / 9:24

fat ass shaking, girl moaning & groaning. we also spread anal & hairy vagina so we can look there. daddy punishes his young & beautiful girl. spanking her big white ass very hard.

PornBox 2 years ago

Thicc Juicy BBQ

Thicc Juicy BBQ

Rainblow 9 months ago

Hanna Ven Private Show

58% HD 2:00 / 10:25

Hanna Ven Private Show

Flirt4Free 1 year ago

thaysa carvalho (ts) fucked hard by white boyfriend

thaysa carvalho (ts) fucked hard by white boyfriend

PornOne 3 years ago

T-Girls On Film 29

63% HD 0:30 / 1:20:00

T-Girls On Film 29

AEBN 14 years ago

TS Yasmin Lee humiliates her sexist boss Lucas Knight with her meat

TS Yasmin Lee humiliates her sexist boss Lucas Knight with her meat

UrGayPorn 1 month ago

TS Wife Wait All Day For Her Husband's Dick

TS Wife Wait All Day For Her Husband's Dick

Eporner 4 months ago

Jhon & Derek & Chris Private Show

44% HD 2:00 / 31:06

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Ryann Clark Private Show

58% HD 2:00 / 4:36

Ryann Clark Private Show

Flirt4Free 3 months ago

Master & Christian Mckenzie & Christian Rey Private Show

54% HD 2:00 / 13:53

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 2 years ago

Desire Sweet Private Show

HD 2:00 / 34:32

Desire Sweet Private Show

Flirt4Free 2 days ago

Milk ENEMA bath for SISSY slave with full CONDOM inside his ass

Milk ENEMA bath for SISSY slave with full CONDOM inside his ass

xHamster 10 months ago

Casey Kisses' hard missionary bang with a teacher

Casey Kisses' hard missionary bang with a teacher

Pornicom 2 weeks ago

Shemale Izabelly Santana Delicious Face Fuck VII

Shemale Izabelly Santana Delicious Face Fuck VII

Clips4sale 1 month ago

It appears the spanker machine is also good for ballbusting

It appears the spanker machine is also good for ballbusting

xHamster 3 years ago

Punishing the Pool Boy

Punishing the Pool Boy

Hoes.tube 3 months ago

T-GIRL PUNISHMENT - (Full Original Clip in HD Version)

T-GIRL PUNISHMENT - (Full Original Clip in HD Version)

SortPorn 3 years ago

Femboy Craves CBT Punishment

70% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 3 years ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

FetishShrine 2 months ago

21mins (FULL) Trio of Kinky Dommes Show No Mercy

21mins (FULL) Trio of Kinky Dommes Show No Mercy

xHamster 1 year ago

Shemale Julia Vass Rotten Farts On Bitch Face III

57% HD 0:11 / 5:10

Shemale Julia Vass Rotten Farts On Bitch Face III

Clips4sale 1 year ago

I Tease and Squeeze his little sissy balls

I Tease and Squeeze his little sissy balls

xHamster 9 months ago

Russian Shemale Struggles with Her Dominant Lover

Russian Shemale Struggles with Her Dominant Lover

Babe4 1 year ago

Alicia Williams in My Step Sister Wants Me To Walk Her Like A Dog - S18:E1

Alicia Williams in My Step Sister Wants Me To Walk Her Like A Dog - S18:E1

Tranny.one 3 years ago

Submissive Slave Dominated By Ts Dommes [Full Movie]

Submissive Slave Dominated By Ts Dommes [Full Movie]

xHamster 6 months ago

Feelipe & Adara Private Show

63% HD 2:00 / 5:01

Feelipe & Adara Private Show

Flirt4Free 1 month ago

Shocking Confession to the Wedding Priest!

69% HD 0:39 / 9:27

Shocking Confession to the Wedding Priest!

FapHouse 1 year ago

Gonna Make Love in This Club - Laela Knight Fucks a Line Jumper

53% 0:11 / 39:51

Gonna Make Love in This Club - Laela Knight Fucks a Line Jumper

C4S 2 years ago

Her Prisoner Part 23 - Sissy Training VI **wmv version**

63% 4K 0:45 / 10:09

Her Prisoner Part 23 - Sissy Training VI **wmv version**

Clips4sale 1 year ago

Femdom shemale Aubrey Kate fucks face and tight ass to male sub Pierce Paris in her pink dungeon

Femdom shemale Aubrey Kate fucks face and tight ass to male sub Pierce Paris in her pink dungeon

Eporner 2 days ago

A Peculiar Cuckold Foursome Story of a Huge Jugs hot and Lusty cougar with 2 Long African Dick big black dick Men & a Cheating Hubby

A Peculiar Cuckold Foursome Story of a Huge Jugs hot and Lusty cougar with 2 Long African Dick big black dick Men & a Cheating Hubby

Love4Porn 2 years ago

Freaks of Nature 29 Humorous insertions Gear Lever

Freaks of Nature 29 Humorous insertions Gear Lever

MatureTubeHere 4 years ago

Trans Stepsister Femdom

50% HD 1:01 / 17:03

Trans Stepsister Femdom

FapHouse 8 months ago

Laundry Room Pounding: Cherish Moans as Dreezy Long Wrecks His Hole

Laundry Room Pounding: Cherish Moans as Dreezy Long Wrecks His Hole

ALOTPorn 3 weeks ago

Alexander Gustavo loves his lustful punishment from TS Morgan Bailey

Alexander Gustavo loves his lustful punishment from TS Morgan Bailey

VikiPorn 1 month ago

I Spanked His Nuts For Cheating. Slap Nuts Cumming

I Spanked His Nuts For Cheating. Slap Nuts Cumming

Love4Porn 4 years ago

9 10 11 12 13

35,426 results found

Narrow your search

punished teen 18+ teen punished 18+ wife punished mom punished secretary punished stepmom punished babysitter punished lesbian punished step dad punished anal bbc punished sara jay punished jenna haze punished angelina valentine punished dylan ryder punished shyla stylez punished ava addams punished pornstar punished bridgette b punished alanah rae punished kelly divine punished

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2025 Pornmd.com. All rights reserved.