Punishment Videos (61,191)

Hot Sissy Extreme 16cm High Heel Shoe Removal Challenge + Milking

66% 4K 0:27 / 1:12:41

Hot Sissy Extreme 16cm High Heel Shoe Removal Challenge + Milking

Clips4sale 3 months ago

Corrine Dittmann Private Show

Corrine Dittmann Private Show

Camster 3 months ago

Sophia Loreen Private Show

HD 2:00 / 52:09

Sophia Loreen Private Show

Camster 2 months ago

Mrs. Foxx has been a naughty!

Mrs. Foxx has been a naughty!

Some.Porn 1 year ago

STEPBROTHER TURNED SISSY AT OUR SLUMBER PARTY 1080P - ELLIE IDOL

46% HD 0:25 / 21:05

STEPBROTHER TURNED SISSY AT OUR SLUMBER PARTY 1080P - ELLIE IDOL

Clips4sale 2 years ago

Max Russel Private Show

Max Russel Private Show

Flirt4Free 3 years ago

BUBBLE BOOTY ESTHER Gets Punished #5 HOT scene full video available now!

BUBBLE BOOTY ESTHER Gets Punished #5 HOT scene full video available now!

AShemaleTube 4 months ago

Bullying her Sissy Balls Part 3: Squeezed & Teased

55% HD 0:10 / 12:19

Bullying her Sissy Balls Part 3: Squeezed & Teased

LoyalFans 1 month ago

We Matched with This Guy and He Said He Was Making a Video for the First Time

We Matched with This Guy and He Said He Was Making a Video for the First Time

XHamster 1 year ago

A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE

A TERRIBLE PUNISHING SESSION FOR THIS POOR SLAVE

AShemaleTube 5 years ago

What a pathetic sissy slut - Time for punishment

What a pathetic sissy slut - Time for punishment

XHamster 7 months ago

Blazing Hot Domination by The Fire FULL video from

Blazing Hot Domination by The Fire FULL video from

XHamster 2 years ago

French Older S&M two of three

French Older S&M two of three

MatureTubeHere 5 years ago

Doc punishing his bratty submissive femboy crossdresser michele

Doc punishing his bratty submissive femboy crossdresser michele

XXXShemalePorn 3 years ago

Dick Tickling Footjob

60% HD 2:00 / 16:03

Dick Tickling Footjob

Flirt4Free 6 years ago

Vicious very matures shemales use a slave guy

Vicious very matures shemales use a slave guy

Fetishpapa 1 year ago

Lika Kai Private Show

62% 4K 2:00 / 8:58

Lika Kai Private Show

Camster 1 month ago

Diapered and spanked (720p)

Diapered and spanked (720p)

Clips4sale 4 years ago

a firm hand for her TS Pet

a firm hand for her TS Pet

IWantClips 3 months ago

Stepmom punishes her stepdaughter

Stepmom punishes her stepdaughter

ShemaleSin 1 month ago

T-girl Angels Vaniity And Mia Isabella Dominate And Punish Thieves With Hardcore Sex

T-girl Angels Vaniity And Mia Isabella Dominate And Punish Thieves With Hardcore Sex

Sheshaft 8 months ago

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

XHamster 10 months ago

Shemale punishers hot fuck

Shemale punishers hot fuck

BeMyHole 5 years ago

”Hardcore sex in a dungeon with transgender punishment”

”Hardcore sex in a dungeon with transgender punishment”

TransHero 2 years ago

Spanking Punishment From A Nun

Spanking Punishment From A Nun

AbTranny 2 years ago

MOMMY PUNISHMENT 2

MOMMY PUNISHMENT 2

AShemaleTube 6 months ago

”River Enza punishes big transgender butthole with dildo”

”River Enza punishes big transgender butthole with dildo”

LesbianBliss 7 months ago

Ashley Porch Private Show

Ashley Porch Private Show

Flirt4Free 2 years ago

Wicked family games two

Wicked family games two

MatureTubeHere 5 years ago

Sissy Discipline (4k)

Premium 4K 25:07

Sissy Discipline (4k)

Clips4sale 5 months ago

Kinky Joanna Jet dominates and punishes her student Sarah Vandella with a big dick in her pussy

Kinky Joanna Jet dominates and punishes her student Sarah Vandella with a big dick in her pussy

Wankoz 10 months 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 3 years ago

Punish Her

Xshemale 5 months ago

Margie Evans Private Show

HD 2:00 / 24:48

Margie Evans Private Show

Camster 3 years ago

Sophie Fantasy Private Show

61% HD 2:00 / 44:13

Sophie Fantasy Private Show

Flirt4Free 1 month ago

Submissive in an Electrified Cage - Punishment Under Needles

Submissive in an Electrified Cage - Punishment Under Needles

XHamster 5 months ago

Ts Dani Marks traps Hex to a sling and fuck him upside down (1080p ENG-sub) Trans Woman - Anal Fucking - Trans Dominatrix - Trans Blowjob - Face Fucking

66% HD 0:34 / 23:18

Ts Dani Marks traps Hex to a sling and fuck him upside down (1080p ENG-sub) Trans Woman - Anal Fucking - Trans Dominatrix - Trans Blowjob - Face Fucking

Clips4sale 1 year ago

Christian & Lian Private Show

54% HD 2:00 / 5:42

Christian & Lian Private Show

Flirt4Free 3 years ago

TS Jesse Punishes A Cis and Trans Man - See Full Video at ShemaleDream.Tube

TS Jesse Punishes A Cis and Trans Man - See Full Video at ShemaleDream.Tube

Eporner 8 years ago

Black Shemale Takes a Painfully Big Cock

Black Shemale Takes a Painfully Big Cock

AShemaleTube 8 years ago

Marian & Richard Private Show

70% HD 2:00 / 4:23

Marian & Richard Private Show

Camster 1 month ago

Sissy Maid's caning punishment WL1718

71% 0:10 / 19:38

Sissy Maid's caning punishment WL1718

Clips4sale 2 years ago

Please punish me teacher for being bad

Please punish me teacher for being bad

Fapcat 1 year ago

Useless dude fucked anally in 3some

Useless dude fucked anally in 3some

Some.Porn 1 year ago

Slut Training PT2 - lets make use the teeth for a reason! - 480P

66% 0:15 / 9:37

Slut Training PT2 - lets make use the teeth for a reason! - 480P

Clips4sale 2 years ago

Sissy bride chastity - Wedding night tease

50% 0:11 / 12:31

Sissy bride chastity - Wedding night tease

Clips4sale 2 years ago

German Domina punish a crossdresser slave

German Domina punish a crossdresser slave

DrTuber 3 years ago

Blue Bunny Femboy Rope Slave's Punishment Challenge - Ultra-Thin Rope Tight Standing Bind, Hands Wrapped, Mouth Stuffed, Chastity Locked & Cum in Chastity Hogtie Milking Until Exhaustion

Premium 1:04:52

Blue Bunny Femboy Rope Slave's Punishment Challenge - Ultra-Thin Rope Tight Standing Bind, Hands Wrapped, Mouth Stuffed, Chastity Locked & Cum in Chastity Hogtie Milking Until Exhaustion

Clips4sale 9 months ago

Femdom Anal Annihilation: 60-minutes of Giant Strap-on Pegging & Deep Fisting Full-length

HD 1:01 / 1:04:15

Femdom Anal Annihilation: 60-minutes of Giant Strap-on Pegging & Deep Fisting Full-length

FapHouse 1 month ago

Very Hard Punishment For Tranny Slut Large Enema and Electro shock

Very Hard Punishment For Tranny Slut Large Enema and Electro shock

XHamster 4 years ago

Alejandro & Bayron & Angel & Johan Private Show

Alejandro & Bayron & Angel & Johan Private Show

Flirt4Free 2 years ago

Lanista Bear , Domina Satana and Allegro in the Dungeon Part 1

Lanista Bear , Domina Satana and Allegro in the Dungeon Part 1

XHamster 4 months ago

Penny Barber punished hard by her Ts for being a naughty tranny

Penny Barber punished hard by her Ts for being a naughty tranny

Katestube 9 months ago

Topping Emma Rose

47% HD 0:10 / 20:34

Topping Emma Rose

LoyalFans 8 months ago

Teen Ladyboy Meme Gives Blowjob And Ass Fucked

Teen Ladyboy Meme Gives Blowjob And Ass Fucked

Sheshaft 7 years ago

Crossdresser Mistress Luci May punishes spanks blonde tranny maid tight ass

Crossdresser Mistress Luci May punishes spanks blonde tranny maid tight ass

AShemaleTube 9 years ago

West Wing Porn - the Dirtiest Business of All - Politics

West Wing Porn - the Dirtiest Business of All - Politics

PornFreeNow 2 months 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 2 years ago

Mint & Melissa Private Show

Mint & Melissa Private Show

Flirt4Free 3 years ago

Sophia Loreen Private Show

4K 2:00 / 11:26

Sophia Loreen Private Show

Camster 11 months ago

Angel Joseph Private Show

62% HD 2:00 / 5:48

Angel Joseph Private Show

Flirt4Free 2 weeks ago

Naughty little slave wants to be punished by shemale mistress

Naughty little slave wants to be punished by shemale mistress

Tranny.one 9 years ago

Lisan & Mine Private Show

55% 4K 2:00 / 4:59

Lisan & Mine Private Show

Camster 1 week ago

Rika Fox gets punished and takes a HUGE facial cumshot available now 😈

Rika Fox gets punished and takes a HUGE facial cumshot available now 😈

AShemaleTube 1 year ago

You Missed a Spot

60% HD 1:01 / 37:53

You Missed a Spot

FapHouse 11 months ago

”Divine Goddess in latex punish man”

”Divine Goddess in latex punish man”

TransHero 9 months ago

India new sexx girls happy moment

India new sexx girls happy moment

XHamster 1 year ago

Jhon & Derek & Chris Private Show - Part 2

67% HD 2:00 / 5:56

Jhon & Derek & Chris Private Show - Part 2

Flirt4Free 4 years ago

Bad Boy Whipping Hard by His Friend

Bad Boy Whipping Hard by His Friend

XHamster 1 month ago

Mike Swift & David Golden Private Show

HD 2:00 / 13:21

Mike Swift & David Golden Private Show

Flirt4Free 2 months ago

Mistress Sophie Spanks and Fucks Me

HD 0:25 / 14:37

Mistress Sophie Spanks and Fucks Me

IWantClips 3 months ago

Daylene Goes Deep

Daylene Goes Deep

Some.Porn 1 year ago

Chubby shemale punisher puts her male slave on a leash and fucks him

Chubby shemale punisher puts her male slave on a leash and fucks him

AShemaleTube 2 years ago

snacktime! the trans giantess is hungry for ... you!

HD 0:29 / 17:20

snacktime! the trans giantess is hungry for ... you!

PornBox 1 month ago

”T-girl wifey wait all day for her hubby's shaft”

”T-girl wifey wait all day for her hubby's shaft”

429Men 7 months ago

BDSM Sissy Slut get punish and hits

BDSM Sissy Slut get punish and hits

XHamster 1 year ago

Trans head mistress Joanna Jet punishes slutty student Sarah Vandella

Trans head mistress Joanna Jet punishes slutty student Sarah Vandella

Pornwhite 6 months ago

Nettles chastity torture

Nettles chastity torture

XHamster 3 years ago

Micky Mackenzie Private Show

66% HD 2:00 / 1:02:46

Micky Mackenzie Private Show

Flirt4Free 12 years ago

Sissy Trans Punished with Nipple Torture and Spanking!

Sissy Trans Punished with Nipple Torture and Spanking!

XXXShemalePorn 5 years ago

Michelle Firestone swaps her pecker in and out of Juliette Marchs holes

Michelle Firestone swaps her pecker in and out of Juliette Marchs holes

Sheshaft 1 year ago

One Night in Paris (part 2 of 2)

One Night in Paris (part 2 of 2)

PornFreeNow 3 months ago

Subby Gets Ass Punished by TS Sasha Blue

Subby Gets Ass Punished by TS Sasha Blue

ShemaleSex 4 months ago

A Private Discipline

A Private Discipline

Some.Porn 9 months ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

62% HD 1:01 / 22:05

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

FapHouse 4 months ago

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

58% 0:39 / 32:47

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

FapHouse 8 months ago

Taylor Diamond was naughty so her Sir punishes her ass for over an hour.

Premium HD 1:05:30

Taylor Diamond was naughty so her Sir punishes her ass for over an hour.

XNXXGold 4 years ago

Edging Masturbation with Post Climax Punishment

Edging Masturbation with Post Climax Punishment

ShemaleSin 3 months ago

”Thicc Juicy BBQ”

”Thicc Juicy BBQ”

ThePornstar 1 year ago

Black Teen With Large Titties and natura boobs Gets Punished For Bad Grades - Alina Ali

Black Teen With Large Titties and natura boobs Gets Punished For Bad Grades - Alina Ali

Ebony8 1 year ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

XHamster 1 year ago

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

AShemaleTube 11 months ago

Runaway Punished with spitroast + left leaking tgirls cum

61% HD 0:10 / 13:00

Runaway Punished with spitroast + left leaking tgirls cum

LoyalFans 2 years ago

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

74% HD 1:01 / 13:12

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

FapHouse 7 months ago

Sophia Loreen Party on Aug 13, 2026 - Part 4

4K 2:00 / 1:06:43

Sophia Loreen Party on Aug 13, 2026 - Part 4

Camster 1 month ago

Natassia Dream and Casper Coxx

Natassia Dream and Casper Coxx

XHamster 1 year ago

Sophia Loreen Party on May 30, 2026 - Part 3

61% HD 2:00 / 1:08:30

Sophia Loreen Party on May 30, 2026 - Part 3

Camster 3 months ago

Marianna,young gal in heels gets ass whip

61% HD 0:39 / 3:19

Marianna,young gal in heels gets ass whip

FapHouse 6 years ago

Mormon Jock Punished with Hardcore Penalty for Being Late for Sex

Mormon Jock Punished with Hardcore Penalty for Being Late for Sex

GayX 1 month ago

Mistress and Her maid

73% 0:20 / 6:51

Mistress and Her maid

Clips4sale 1 year ago

Strict tranny mistress punishing guy

Strict tranny mistress punishing guy

AShemaleTube 13 years ago

eighteen Year Old Bratty Trans Lalin girl Stepdaughter Gets Punished For Coming Home Late

eighteen Year Old Bratty Trans Lalin girl Stepdaughter Gets Punished For Coming Home Late

FreePorn8 1 day ago

Foot Tease & POV Ball Busting (HD1080 WMV)

65% 0:11 / 11:25

Foot Tease & POV Ball Busting (HD1080 WMV)

Clips4sale 4 years ago

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Xshemale 2 years ago

Damn stepmm, your tits are insane!

Damn stepmm, your tits are insane!

Some.Porn 2 years ago

Ideal booty Ani Ebony Fox gets punished in gangbang

Ideal booty Ani Ebony Fox gets punished in gangbang

Ebony8 1 year ago

Chained hentai maid gets whipped and hard punishment

Chained hentai maid gets whipped and hard punishment

SleazyNEasy 12 years ago

Dazzling Rose Private Show

Dazzling Rose Private Show

Flirt4Free 1 year ago

Slave Olympics and the Punishment Orgy aftermath FullHD

55% HD 0:11 / 23:21

Slave Olympics and the Punishment Orgy aftermath FullHD

Clips4sale 4 years ago

cuntwhipping stapler ache

cuntwhipping stapler ache

MatureTubeHere 5 years ago

dommes in heels punish innocent trans catgirl

HD 0:30 / 13:24

dommes in heels punish innocent trans catgirl

PornBox 3 years ago

Blond Lassie Down On Her Luck Banged By Huge Movers - Dogfart

Blond Lassie Down On Her Luck Banged By Huge Movers - Dogfart

Some.Porn 1 year ago

Allicia Nogueira spanks and fucks her slave until messy

Allicia Nogueira spanks and fucks her slave until messy

XHamster 2 years ago

Maya Spring Party on Aug 11, 2026 - Part 3

65% 4K 2:00 / 50:00

Maya Spring Party on Aug 11, 2026 - Part 3

Flirt4Free 1 month ago

Sandy Lee Private Show

61% HD 2:00 / 13:41

Sandy Lee Private Show

Flirt4Free 10 years ago

Mint & Melissa Private Show

Mint & Melissa Private Show

Flirt4Free 3 years ago

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

KAMS 1 year ago

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

XHamster 1 year ago

”Shemale Delia DeLions punishes stepson & Siouxsie Q in spicy 3some”

”Shemale Delia DeLions punishes stepson & Siouxsie Q in spicy 3some”

StarWank 1 year ago

Mint & Melissa Private Show

63% HD 2:00 / 6:21

Mint & Melissa Private Show

Flirt4Free 4 years ago

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