Punish Videos (39,862)

Master Collins Private Show

HD 2:00 / 2:41:27

Master Collins Private Show

Flirt4Free 2 weeks ago

Shemale punishers indoors gangbang

Shemale punishers indoors gangbang

BeMyHole 5 years ago

Jamer & Owen & Hercules Private Show

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years ago

A Gay Guy Is Punished Harshly By A Double Team Of Shemales

A Gay Guy Is Punished Harshly By A Double Team Of Shemales

ShemaleSex 2 months ago

Time to Model Some Speedos

Time to Model Some Speedos

Flirt4Free 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 week ago

FTM-Full Bladder, Edging Punishment, Squirting, Biggest Clitoris, Chubby Hirsute Soaked Snatch, Butch Dyke, Trans

FTM-Full Bladder, Edging Punishment, Squirting, Biggest Clitoris, Chubby Hirsute Soaked Snatch, Butch Dyke, Trans

ShemaleSin 4 months ago

Blk Mailed Into Doing Some Wild Stuff

Blk Mailed Into Doing Some Wild Stuff

FapHouse 4 months ago

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

xHamster 1 month ago

Three domina shemales tie up a dude and fuck him before

Three domina shemales tie up a dude and fuck him before

xHamster 1 year ago

Bound TS Honey Dominates With Huge Cock

Bound TS Honey Dominates With Huge Cock

TransTube.tv 4 days ago

My TS Stepdaughter Scene 4 - Kiss and Make Up!

HD 0:44 / 28:45

My TS Stepdaughter Scene 4 - Kiss and Make Up!

Transsensual 6 years ago

Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.

Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.

xHamster 2 years ago

Darksome skin transsexual punisher screws a chap in servitude and cums

Darksome skin transsexual punisher screws a chap in servitude and cums

ShemaleSin 1 year ago

Desire Sweet Private Show

63% HD 2:00 / 7:58

Desire Sweet Private Show

Flirt4Free 6 days ago

Sophia Loreen Party on Jan 16, 2026 - Part 3

4K 2:00 / 45:06

Sophia Loreen Party on Jan 16, 2026 - Part 3

Flirt4Free 4 weeks ago

One blonde and three brunette tranny punishers fuck a dude

One blonde and three brunette tranny punishers fuck a dude

xHamster 1 year ago

”Hogtied blonde caned & screwed”

”Hogtied blonde caned & screwed”

TransHero 2 months ago

Trans PornStar Taylor Jennings vs Femdom Alice Skary

Trans PornStar Taylor Jennings vs Femdom Alice Skary

Tranny.one 4 years ago

Thick ebony shemale punishes a dude hard

Thick ebony shemale punishes a dude hard

TrannyGem 2 years ago

Charlie Cano Private Show

61% HD 2:00 / 22:53

Charlie Cano Private Show

Flirt4Free 3 years ago

Brihana Boll Private Show

HD 2:00 / 14:33

Brihana Boll Private Show

Flirt4Free 3 weeks ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 month ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 months ago

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

xHamster 1 month ago

Luccas & Jhordy Private Show

59% HD 2:00 / 43:43

Luccas & Jhordy Private Show

Flirt4Free 4 months ago

Sofi Betancourt Private Show

63% HD 2:00 / 17:59

Sofi Betancourt Private Show

Flirt4Free 2 years ago

Rope tied TS Ella Hollywood is anal pounded deep by Sebastian Keys

Rope tied TS Ella Hollywood is anal pounded deep by Sebastian Keys

Wankoz 6 months ago

Slender tranny punishing her gf

Slender tranny punishing her gf

aShemaleTube 2 years ago

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

xHamster 1 month ago

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 3 weeks ago

Giant Goddess in High Heels Humiliation, Little Human Crushed

Giant Goddess in High Heels Humiliation, Little Human Crushed

FapHouse 7 months ago

Michael Hawtin Private Show

HD 2:00 / 32:48

Michael Hawtin Private Show

Flirt4Free 1 year ago

Naughty TGirl maid bent over Milfs knee for ass spanking

Naughty TGirl maid bent over Milfs knee for ass spanking

Tranny.one 4 years ago

Master & Ithan Private Show

60% HD 2:00 / 13:43

Master & Ithan Private Show

Flirt4Free 7 months ago

Sophia Loreen Party on Sep 21, 2024 - Part 2

HD 2:00 / 50:14

Sophia Loreen Party on Sep 21, 2024 - Part 2

Flirt4Free 1 year ago

Part 1 - Crazywifeslut and Futa Luсy Fuck Doll From Mrlsexdolls Compete to See Whose Ass Is Stronger

Part 1 - Crazywifeslut and Futa Luсy Fuck Doll From Mrlsexdolls Compete to See Whose Ass Is Stronger

FapHouse 2 months ago

Between the Lines & Between My Legs

Between the Lines & Between My Legs

xHamster 4 months ago

Three shemale punishers in black leather boots fuck their

Three shemale punishers in black leather boots fuck their

xHamster 1 year ago

Nasty Secretary

HD 2:00 / 21:26

Nasty Secretary

Flirt4Free 2 years ago

Dustin Hans Private Show

Dustin Hans Private Show

Flirt4Free 1 week ago

Jessica Liam Private Show

Jessica Liam Private Show

Flirt4Free 1 week ago

Futa None punish little brat sissy

Futa None punish little brat sissy

xHamster 1 year ago

Alexxa & Francesco Private Show

63% HD 2:00 / 12:09

Alexxa & Francesco Private Show

Flirt4Free 2 years ago

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 1 week ago

”Rope tied Tranny Ella Hollywood is ass fucking pounded deep by Sebastian Keys”

”Rope tied Tranny Ella Hollywood is ass fucking pounded deep by Sebastian Keys”

LesbianBliss 1 week ago

Italian Transsexual Job 5

50% HD 0:30 / 2:39:00

Italian Transsexual Job 5

AEBN 16 years ago

Joker Does Some Ass Play with the Ohmibod

Joker Does Some Ass Play with the Ohmibod

Flirt4Free 5 years ago

Talking at Work

HD 2:00 / 11:57

Talking at Work

Flirt4Free 1 year 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

Transsexual Teacher Punishes Her Slutty Student

Transsexual Teacher Punishes Her Slutty Student

BeMyHole 1 year ago

You Failed No Nut November

You Failed No Nut November

FapHouse 11 months ago

Think twice before disrespecting your principal!

Think twice before disrespecting your principal!

Fapcat 8 months ago

FUCK REALISTIC PUSSY & LOUD MOANING GUY & TANTALY SEX DOLL, UNTIL FUCKING CUM ON BELLY - SoloXman

FUCK REALISTIC PUSSY & LOUD MOANING GUY & TANTALY SEX DOLL, UNTIL FUCKING CUM ON BELLY - SoloXman

xHamster 2 years ago

Danna Hudson Private Show

Danna Hudson Private Show

Flirt4Free 2 years ago

Brutus K Private Show

HD 2:00 / 28:20

Brutus K Private Show

Flirt4Free 5 years ago

SISSY DIAPER slave gets PEGGED after releasing PISS ENEMA

SISSY DIAPER slave gets PEGGED after releasing PISS ENEMA

xHamster 1 year ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 1 week ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 1 week ago

”Titty tgirl Ember Fiera slaps & fucks Andrew Connor's booty”

”Titty tgirl Ember Fiera slaps & fucks Andrew Connor's booty”

TransHero 2 years ago

The Wicked Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

The Wicked Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

ShemaleSin 1 month ago

Hanna Ven Private Show

HD 2:00 / 14:45

Hanna Ven Private Show

Flirt4Free 1 year ago

Hot Crossdresser's Slow Punishment

68% HD 1:01 / 19:59

Hot Crossdresser's Slow Punishment

FapHouse 8 months ago

Desire Sweet Private Show

HD 2:00 / 24:38

Desire Sweet Private Show

Flirt4Free 5 days ago

Master Socks Punishes Me Hard !

65% 4K 2:00 / 14:08

Master Socks Punishes Me Hard !

Flirt4Free 4 months ago

Want to warm up this morning? (fire) JOIN the group and get a sexy show with my body, strip, spanks, twerk, and RIDE TOY... lets get wet and hot (yummy)

Want to warm up this morning? (fire) JOIN the group and get a sexy show with my body, strip, spanks, twerk, and RIDE TOY... lets get wet and hot (yummy)

Flirt4Free 1 year ago

sissy punishment by wife caning-spanking-fucking (camera 1)

sissy punishment by wife caning-spanking-fucking (camera 1)

AbTranny 7 years ago

Naughty smoking blonde crossdresser maid has tight pert ass spanked for hot kinky punishment

Naughty smoking blonde crossdresser maid has tight pert ass spanked for hot kinky punishment

aShemaleTube 8 years ago

Master Collins Private Show

HD 2:00 / 21:41

Master Collins Private Show

Flirt4Free 1 year ago

trio.

Tranny.one 4 years ago

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

Sheshaft 7 months ago

My fag life and journey serving Sir

My fag life and journey serving Sir

Tranny.one 4 years ago

Sandy Nell Private Show

4K 2:00 / 24:11

Sandy Nell Private Show

Flirt4Free 1 month ago

”Hot shemale Stefani Special rails stranger Endza Adairs in the sauna”

”Hot shemale Stefani Special rails stranger Endza Adairs in the sauna”

429Men 3 weeks ago

Sabrina Smiith Private Show

4K 2:00 / 14:22

Sabrina Smiith Private Show

Flirt4Free 1 month ago

Shemaleplace.org - crossdresser bitch receives punishment

Shemaleplace.org - crossdresser bitch receives punishment

XXXShemalePorn 2 years ago

Abril & Nadimara Private Show

HD 2:00 / 17:46

Abril & Nadimara Private Show

Flirt4Free 2 years ago

Emma & Master Private Show

Emma & Master Private Show

Flirt4Free 1 day ago

Fantasy Football Loser

Fantasy Football Loser

FapHouse 3 months ago

”Shemale pornstar Lena Kelly's Kinky Encounter with Sgt Miles”

”Shemale pornstar Lena Kelly's Kinky Encounter with Sgt Miles”

Trashreality 1 year ago

Julieta Shayk Private Show

HD 2:00 / 10:07

Julieta Shayk Private Show

Flirt4Free 5 years ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 1 week ago

Asian MILF shemale domina punish fucked her assistant

Asian MILF shemale domina punish fucked her assistant

Tranny.one 4 years ago

Beg for a Take Down. Beg. Ts Ms. Toya and her cop cock.

Beg for a Take Down. Beg. Ts Ms. Toya and her cop cock.

AbTranny 9 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Must-share moment from "perform extreme cam assignments with fire and thumbtacks"

Must-share moment from "perform extreme cam assignments with fire and thumbtacks"

xHamster 3 months ago

Tbabe River Enza tied up in diaper with hot fellow shemale

Tbabe River Enza tied up in diaper with hot fellow shemale

UrGayPorn 1 year ago

Tight Breast Bind Exposed Ass Whipped and Plugged Femdom

73% HD 0:55 / 20:47

Tight Breast Bind Exposed Ass Whipped and Plugged Femdom

Clips4sale 1 year ago

Sissy marionette Harley Quinn smashed

Sissy marionette Harley Quinn smashed

TransTube.tv 1 year ago

Gabriella Bruni Private Show

Gabriella Bruni Private Show

Flirt4Free 8 months ago

Latex Shemale Dom Pegs Sub

Latex Shemale Dom Pegs Sub

TrannyGem 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 8 months ago

Ohmibod and Cumshot

HD 2:00 / 46:13

Ohmibod and Cumshot

Flirt4Free 7 years ago

”Nutty : Bareback Punishment”

”Nutty : Bareback Punishment”

TransHero 6 years ago

”Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux”

”Huge boobs transgender Leilani Li anally rammed submissive blond Sage Roux”

Zatube 2 months ago

The Mistress's Punishment for the Cross-dressing Masochistic Man Is Strapon Deepthroating, Hot Wax, and Whipping

The Mistress's Punishment for the Cross-dressing Masochistic Man Is Strapon Deepthroating, Hot Wax, and Whipping

FapHouse 4 weeks ago

Gagged fastened black lesbo serf Nikki Darling down on knees with wrists and ankles fastened to spreader bar behind her back then perspired in hogtie caned by lezdom Claire Adams

Gagged fastened black lesbo serf Nikki Darling down on knees with wrists and ankles fastened to spreader bar behind her back then perspired in hogtie caned by lezdom Claire Adams

Ebony8 4 months ago

Muscled leather hunk at the mercy of Mr. Ducati

Premium 68% HD 53:51

Muscled leather hunk at the mercy of Mr. Ducati

KinkMen 10 years ago

Gabriella Bruni Private Show

61% 4K 2:00 / 5:58

Gabriella Bruni Private Show

Flirt4Free 5 months ago

College Pegging Part 2 - Miss Mk's Office - the Girls Get Dragged Into the Heads Office to Explain What They Have Been up to

58% HD 1:01 / 18:34

College Pegging Part 2 - Miss Mk's Office - the Girls Get Dragged Into the Heads Office to Explain What They Have Been up to

FapHouse 1 year ago

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

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

xHamster 4 weeks ago

Hot trannies punishing stud

Hot trannies punishing stud

aShemaleTube 12 years ago

Desire Sweet Private Show

HD 2:00 / 10:14

Desire Sweet Private Show

Flirt4Free 5 days ago

Prince Flynn Private Show

Prince Flynn Private Show

Flirt4Free 1 year ago

plump older caning

plump older caning

MatureTubeHere 4 years ago

Rika Fox gets punished and takes a MASSIVE facial

Rika Fox gets punished and takes a MASSIVE facial

aShemaleTube 1 year ago

Fear leads to Hot Fucking in this Steamy TsSeduction Switch Scene

Fear leads to Hot Fucking in this Steamy TsSeduction Switch Scene

AbTranny 9 years ago

dominated by osha inspector princess donna

55% HD 0:30 / 33:38

dominated by osha inspector princess donna

PornBox 1 year ago

Sissy Punished and Fucked for Removeing her Chastity Part 3 Final

Sissy Punished and Fucked for Removeing her Chastity Part 3 Final

BeMyHole 5 years ago

”Big dick shemales turn their yoga class into an ass fucking 3some”

”Big dick shemales turn their yoga class into an ass fucking 3some”

ThePornstar 1 month ago

TS Secretary Dominates Her Boss

TS Secretary Dominates Her Boss

Fapcat 1 year ago

SISSY receives chocolate ENEMA ang a big BUTT PLUG before CUM

SISSY receives chocolate ENEMA ang a big BUTT PLUG before CUM

xHamster 1 year ago

Extreme Anal Sissy Femboy Fucked Compilation Nasty Cosplay Ass Gaped

55% HD 1:01 / 35:30

Extreme Anal Sissy Femboy Fucked Compilation Nasty Cosplay Ass Gaped

FapHouse 4 months ago

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

xHamster 2 months ago

Lora Bakers Private Show

58% HD 2:00 / 5:36

Lora Bakers Private Show

Flirt4Free 1 year ago

Sissy Secretary Slut Wedgie and Anal Fucking with Dildo

Sissy Secretary Slut Wedgie and Anal Fucking with Dildo

FapHouse 6 days ago

CD Slut Fucked by Anon Grindr Cock

CD Slut Fucked by Anon Grindr Cock

Tranny.one 4 years ago

The Queenpin, The Fox & The Punishing A Narc In Sex Sting With Courtney Taylor, Lorelei Lee And Little Bird

The Queenpin, The Fox & The Punishing A Narc In Sex Sting With Courtney Taylor, Lorelei Lee And Little Bird

PornUse 7 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 week ago

Italian She Male 25

69% HD 0:30 / 2:42:00

Italian She Male 25

AEBN 18 years ago

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