Punish Videos (39,719)

Part 1:- Goddess Satana teaches Headmistress Frankie with BooBoo

Part 1:- Goddess Satana teaches Headmistress Frankie with BooBoo

ShemaleSin 3 weeks ago

Live in sissy girls uniform inspection

68% 0:30 / 6:12

Live in sissy girls uniform inspection

Clips4sale 1 year ago

T-Girl domme anal punish cheater

T-Girl domme anal punish cheater

Sheshaft 5 years ago

Troy Khalil Private Show

HD 2:00 / 10:46

Troy Khalil Private Show

Flirt4Free 2 years ago

TS sub in latex Ella Hollywood bound and anal punished by master Sebastian Keys

TS sub in latex Ella Hollywood bound and anal punished by master Sebastian Keys

KeekAss 4 months ago

BNWO Sissy Breeding Stables

45% HD 0:29 / 10:41

BNWO Sissy Breeding Stables

Clips4sale 4 months ago

Three shemales in leather outfits spank and fuck a stud in

Three shemales in leather outfits spank and fuck a stud in

xHamster 1 year ago

Sissies Punishment by Princess Aurora & Slavena

Sissies Punishment by Princess Aurora & Slavena

Clips4sale 1 year ago

SHEMALE DOMINATION - 73 - ANNE ANTONELA & RICK BITCH - CLIP 3 OF 6 - MP4

65% 0:18 / 5:05

SHEMALE DOMINATION - 73 - ANNE ANTONELA & RICK BITCH - CLIP 3 OF 6 - MP4

Clips4sale 7 months ago

Jessica Host One Night Stand

Jessica Host One Night Stand

aShemaleTube 7 months ago

”Hardcore sex in a dungeon with transgender punishment”

”Hardcore sex in a dungeon with transgender punishment”

429Men 3 weeks ago

The punishment of Louisa Part 8 of 8 Final clip in this set

66% 0:30 / 6:50

The punishment of Louisa Part 8 of 8 Final clip in this set

Clips4sale 1 year ago

”Huge tits Latin STEPMOM & chubby beauty fuck big cock tbabe professor”

”Huge tits Latin STEPMOM & chubby beauty fuck big cock tbabe professor”

Rainblow 11 months ago

Post Orgasm Fleshlight Milking

HD 1:01 / 18:00

Post Orgasm Fleshlight Milking

FapHouse 2 years ago

Cigar Domme Lilli Holly's Bound & Smoked Punishment

Cigar Domme Lilli Holly's Bound & Smoked Punishment

xHamster 11 months ago

Crossdresser Dominates Pussy and Ass

Crossdresser Dominates Pussy and Ass

xHamster 3 months ago

roommate discipline with sophie ladder and sinn sage tranny one

roommate discipline with sophie ladder and sinn sage tranny one

PornOne 2 years ago

Kinky Morning Quickie w/ Nicole Knight!

Kinky Morning Quickie w/ Nicole Knight!

APClips 11 months ago

River Enza Punishes Big Tranny Asshole With Dildo

River Enza Punishes Big Tranny Asshole With Dildo

ShemaleSex 1 month ago

Electro stimulation and remote control butt plug orgasm

Electro stimulation and remote control butt plug orgasm

XVideos 5 months ago

crossdresser slave punishment

crossdresser slave punishment

Eporner 4 years ago

Mistress fucked his ass in the shower

Mistress fucked his ass in the shower

XVideos 1 year ago

Punish-fucked By Head Mistress Starlight Preview With Ally Sparkles And Johnny Starlight

Punish-fucked By Head Mistress Starlight Preview With Ally Sparkles And Johnny Starlight

AbTranny 2 years ago

Spank my Hole

77% 0:57 / 16:08

Clips4sale 2 years ago

esmagando a cara da sissy com nossas bundas enormes

esmagando a cara da sissy com nossas bundas enormes

PornBox 2 years ago

Lora Bakers Private Show

HD 2:00 / 24:21

Lora Bakers Private Show

Flirt4Free 1 year ago

Sissy Club Slut: Deep Throating, Pegging, and More PART 1 OF 2 (1080p)

47% HD 0:30 / 21:43

Sissy Club Slut: Deep Throating, Pegging, and More PART 1 OF 2 (1080p)

Clips4sale 2 years ago

TRANNY PUNISHERS - Sexy and Kinky Tranny Domination

TRANNY PUNISHERS - Sexy and Kinky Tranny Domination

ShemaleSin 1 year ago

Useless male to prissy sissy - Double domme training

Useless male to prissy sissy - Double domme training

Clips4sale 1 year ago

Hot milf fucked him hard with strapon

Hot milf fucked him hard with strapon

XVideos 1 year ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

63% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 3 weeks ago

Sophia Loreen Party on Dec 10, 2025 - Part 2

4K 2:00 / 1:26:04

Sophia Loreen Party on Dec 10, 2025 - Part 2

Flirt4Free 1 month 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 3 years ago

”Tranny Yasmin Lee humiliates her sexist boss Lucas Knight with her shaft”

”Tranny Yasmin Lee humiliates her sexist boss Lucas Knight with her shaft”

LesbianBliss 1 month ago

Sophia Loreen Party on Jul 4, 2024

62% HD 2:00 / 1:19:46

Sophia Loreen Party on Jul 4, 2024

Flirt4Free 1 year ago

”Hardcore sex in a dungeon with shemale punishment”

”Hardcore sex in a dungeon with shemale punishment”

4Wank 1 year ago

Visceratio Gets Her Ass Punished - ShemaleDreamCams

Visceratio Gets Her Ass Punished - ShemaleDreamCams

Sheshaft 7 years ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

68% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 2 years ago

Double Trans Girl Deep Throat Punishment PART 1

55% 4K 0:29 / 16:22

Double Trans Girl Deep Throat Punishment PART 1

Clips4sale 2 years ago

Fuck, You Told My Cis Girlfriend That I Cheated On Her With A Trans Dominatrix, Oh And Now She's Here And Y'all Are Going to Doubleteam Spitroast Me Til You Facial Me With A Cumshot?

56% 0:10 / 25:32

Fuck, You Told My Cis Girlfriend That I Cheated On Her With A Trans Dominatrix, Oh And Now She's Here And Y'all Are Going to Doubleteam Spitroast Me Til You Facial Me With A Cumshot?

Clips4sale 1 year ago

Buried Under Shemale Lanah Frias Perfect Ass - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

HD 0:30 / 33:52

Buried Under Shemale Lanah Frias Perfect Ass - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

Clips4sale 2 months ago

Rashel Mendoza Private Show

HD 2:00 / 16:57

Rashel Mendoza Private Show

Flirt4Free 6 months ago

”Tranny Jenna Gargles & Pierce Paris starts the morning with hard ass fucking”

”Tranny Jenna Gargles & Pierce Paris starts the morning with hard ass fucking”

LesbianBliss 3 weeks ago

Futanari teacher punishing her student in a 3d animation

Futanari teacher punishing her student in a 3d animation

xHamster 1 year ago

”Spanking attempt is not enough to discipline the hot stepdaughter”

”Spanking attempt is not enough to discipline the hot stepdaughter”

ThePornstar 1 year ago

Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass

Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass

XVideos 2 years ago

Shemale Jhoany Wilker First Horny Face Fuck - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 33 MINUTES FOR US$ 15,99!

HD 0:26 / 32:55

Shemale Jhoany Wilker First Horny Face Fuck - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 33 MINUTES FOR US$ 15,99!

Clips4sale 1 week ago

Trans Ria Bentley Gets Peg Punished By Dana Delvey

78% 0:30 / 21:27

Trans Ria Bentley Gets Peg Punished By Dana Delvey

Clips4sale 6 months ago

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie Clip 2

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie Clip 2

xHamster 2 months ago

Tender morning of the sissy Alice

Tender morning of the sissy Alice

xHamster 5 months ago

Security man gets his juicy ass smashed deep and hard by the glamorous TS babe in the dressing room

Security man gets his juicy ass smashed deep and hard by the glamorous TS babe in the dressing room

Tranny.one 4 years ago

HR NIGHTMARE *HD 1080*

63% HD 0:35 / 17:56

HR NIGHTMARE *HD 1080*

Clips4sale 3 years ago

Bound up femboy required to cum! Post Climax Punishment

Bound up femboy required to cum! Post Climax Punishment

ShemaleSin 9 months ago

Hot Trans Sabrina gets her punishment after fucking my partner.

Hot Trans Sabrina gets her punishment after fucking my partner.

XVideos 1 month ago

Making A Baddie Out Of My Teen Step-Daughter- Gizelle Blanco

Making A Baddie Out Of My Teen Step-Daughter- Gizelle Blanco

XVideos 2 years ago

you were meant to be a girl: loving feminization and pov bj - SD wmv

you were meant to be a girl: loving feminization and pov bj - SD wmv

Clips4sale 8 months ago

Jessica Host one night stand

Jessica Host one night stand

AbTranny 9 years 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 5 months ago

Mistress Kora Bell, Bell Trans And Kora Bell In Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

Mistress Kora Bell, Bell Trans And Kora Bell In Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

PePorn 2 months ago

TS Nicole Pitty dominates Silvia Bianco's holes with rough anal and deepthroat punishment

TS Nicole Pitty dominates Silvia Bianco's holes with rough anal and deepthroat punishment

Sheshaft 2 months ago

Big ass shemale punisher in leather corset fucks a stud doggystyle

Big ass shemale punisher in leather corset fucks a stud doggystyle

aShemaleTube 11 months ago

Masturbate with Jinx ^^

Masturbate with Jinx ^^

Flirt4Free 10 months ago

Meeting &amp_ Eating New Girlfriend - Gogo Fukme, Lulu Chu / Brazzers / stream full from www.zzfull.com/finally

Meeting &amp_ Eating New Girlfriend - Gogo Fukme, Lulu Chu / Brazzers / stream full from www.zzfull.com/finally

XVideos 3 years ago

Bratty Satin Office Girl Jessica Kat Learns a Lesson

70% 0:25 / 17:35

Bratty Satin Office Girl Jessica Kat Learns a Lesson

Clips4sale 1 year ago

Wedgie to Big Ass Femboy Humiliated and Spanked in Halloween Cosplay by BBC Dildo

Wedgie to Big Ass Femboy Humiliated and Spanked in Halloween Cosplay by BBC Dildo

xHamster 3 months ago

Chastity Cuck Punishment

Premium HD 21:15

Chastity Cuck Punishment

Clips4sale 1 year ago

Headmaster punishes and bangs fastened t-girl student (Natalie Mars)

Headmaster punishes and bangs fastened t-girl student (Natalie Mars)

ShemaleSin 1 year ago

Valentin & Harris Private Show

Valentin & Harris Private Show

Flirt4Free 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 weeks ago

German TS surprised by burglar - as a punishment, he is being fucked hard and pissed on - trailer Emily Adaire TS

German TS surprised by burglar - as a punishment, he is being fucked hard and pissed on - trailer Emily Adaire TS

XVideos 3 years ago

Brats Get Punished

Brats Get Punished

TrashyNeverClassy 11 months ago

BigCock latina TS anal fucked and punished!

BigCock latina TS anal fucked and punished!

aShemaleTube 6 years ago

Mommy Taboo Tgirl Punishment and Facial

Premium HD 35:26

Mommy Taboo Tgirl Punishment and Facial

xnxxGold 3 years ago

Master & Ithan Private Show

62% HD 2:00 / 20:20

Master & Ithan Private Show

Flirt4Free 8 months ago

Release Ya Freak

Release Ya Freak

ShemaleSin 1 year ago

Sophia Loreen Party on Jan 14, 2026 - Part 3

4K 2:00 / 35:36

Sophia Loreen Party on Jan 14, 2026 - Part 3

Flirt4Free 3 weeks ago

BACHELORETTE PARTY

HD 1:25 / 19:38

BACHELORETTE PARTY

BoLatino 1 year ago

Rashel Mendoza Private Show

Rashel Mendoza Private Show

Flirt4Free 7 months ago

Sandy Nell Private Show

61% HD 2:00 / 4:35

Sandy Nell Private Show

Flirt4Free 2 years ago

Tranny domina Barbara Cristina fucks her prisoner doggystyle

Tranny domina Barbara Cristina fucks her prisoner doggystyle

xHamster 9 months ago

Contratamos uma travesti loira dotada para um novo prazer

Premium HD 14:28

Contratamos uma travesti loira dotada para um novo prazer

XVideosRed 2 years ago

Teachers Sa Jay &amp_ Angelina Castro Fuck Pupil Gia in Class!

Teachers Sa Jay &amp_ Angelina Castro Fuck Pupil Gia in Class!

XVideos 9 years ago

Scarleth Broown Private Show

HD 2:00 / 17:31

Scarleth Broown Private Show

Flirt4Free 2 years ago

Ema Devine Private Show

Ema Devine Private Show

Flirt4Free 5 months ago

Moan

HD 2:00 / 13:45

Flirt4Free 1 year ago

Trans Sub Ana Cums Over and Over PART 2

60% HD 0:30 / 12:28

Trans Sub Ana Cums Over and Over PART 2

Clips4sale 4 years ago

Caroline Bella Private Show

63% 4K 2:00 / 5:12

Caroline Bella Private Show

Flirt4Free 7 months ago

Gemma israel is back and wants to punish her slave with her monstrous dick

Gemma israel is back and wants to punish her slave with her monstrous dick

XXXShemalePorn 5 years ago

Denali Danger gets Punished

Denali Danger gets Punished

aShemaleTube 1 year ago

Sophia Loreen Party on Apr 5, 2024

HD 2:00 / 33:57

Sophia Loreen Party on Apr 5, 2024

Flirt4Free 1 year ago

Punishment or Reward?

Punishment or Reward?

C4S 2 years ago

Monserrat Salvatore Private Show

HD 2:00 / 15:28

Monserrat Salvatore Private Show

Flirt4Free 1 year ago

Some wax and spanking before the rough bareback anal

Some wax and spanking before the rough bareback anal

Wankoz 2 years ago

Pegging My Stepson

53% HD 0:10 / 6:32

Pegging My Stepson

LoyalFans 1 year ago

”On The Wrong Track - Reagan Foxx, Madi Collins, Kimmy Kimm”

”On The Wrong Track - Reagan Foxx, Madi Collins, Kimmy Kimm”

TransHero 1 month ago

Sophia Loreen Party on Jan 21, 2026 - Part 3

4K 2:00 / 34:45

Sophia Loreen Party on Jan 21, 2026 - Part 3

Flirt4Free 1 week ago

Sabrina Smiith Private Show

4K 2:00 / 15:26

Sabrina Smiith Private Show

Flirt4Free 3 weeks ago

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

64% 4K 0:30 / 58:54

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

Clips4sale 1 year ago

Dark skinned shemale punisher gets a cumshot on her big tits

Dark skinned shemale punisher gets a cumshot on her big tits

aShemaleTube 11 months ago

”Deeper - Bridgette B Punished”

”Deeper - Bridgette B Punished”

TransHero 1 month ago

Nelly Gale Private Show

66% 4K 2:00 / 30:14

Nelly Gale Private Show

Flirt4Free 2 days ago

SHEMALE DOMINATION - 75 - YASMIN CASTRO & RICK BITCH - CLIP 5 OF 5 - MP4

SHEMALE DOMINATION - 75 - YASMIN CASTRO & RICK BITCH - CLIP 5 OF 5 - MP4

Clips4sale 7 months ago

FULL CLIP! Crazy fetish trannys! Chastity sex with a live rubber doll!

62% HD 0:29 / 18:26

FULL CLIP! Crazy fetish trannys! Chastity sex with a live rubber doll!

Clips4sale 1 year ago

”Loving Step Sister wins Dicklicking Marathon Comp.”

”Loving Step Sister wins Dicklicking Marathon Comp.”

ThePornstar 1 year ago

Dominated By Osha Inspector Princess Donna - FULL SCENE

Dominated By Osha Inspector Princess Donna - FULL SCENE

XVideos 11 months ago

Nyobi Khan - cock worship

Nyobi Khan - cock worship

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

XVideos 8 years ago

Rika Fox gets punished #8 full 23 min video available now 😉 plus all our other collabs

Rika Fox gets punished #8 full 23 min video available now 😉 plus all our other collabs

aShemaleTube 8 months ago

Lance Hart Is Given To TS Foxxy For Punishment

Lance Hart Is Given To TS Foxxy For Punishment

aShemaleTube 9 years ago

3 Maids and the Mistress sissy training group sex foursome group sex anal fucking doubleteam with big dicks and cumshots

3 Maids and the Mistress sissy training group sex foursome group sex anal fucking doubleteam with big dicks and cumshots

Clips4sale 1 year ago

Step Daughter Likes to get hardcore Punishment from her StepDad after rain Dance ( Full Movie )

Step Daughter Likes to get hardcore Punishment from her StepDad after rain Dance ( Full Movie )

XVideos 1 year ago

Mistress Yuna & Lady Lexi - The Whipped Maids - HD

Mistress Yuna & Lady Lexi - The Whipped Maids - HD

Clips4sale 2 years ago

Shemale Pietra Candy First Facesitting IV

Shemale Pietra Candy First Facesitting IV

Clips4sale 2 years ago

Monserrat & Jaxi Private Show

HD 2:00 / 11:12

Monserrat & Jaxi Private Show

Flirt4Free 1 year ago

Trans slave Luzi punished and fucked

HD 0:10 / 14:09

Trans slave Luzi punished and fucked

LoyalFans 2 years ago

Sissyslave Dizzy Miss Sizzy Hogtied!

Sissyslave Dizzy Miss Sizzy Hogtied!

XVideos 7 years ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

67% HD 0:39 / 49:11

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

FapHouse 1 month ago

Gabriella Bruni Private Show

Gabriella Bruni Private Show

Flirt4Free 6 months ago

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

38% 4K 0:29 / 21:02

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

Clips4sale 11 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 weeks ago

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