Punishment Videos (40,310)

Hot European Stud Jerks Off

Hot European Stud Jerks Off

Flirt4Free 9 years ago

Going Knuckle Deep torture

Going Knuckle Deep torture

TrannyGem 5 years ago

Punish Her

Eporner 3 weeks ago

Outdoor Fisting Gangbang - Past the Elbow Featuring Jasmine_dlight, Hairy Kink Mоther & Roxxie Sweetheart

67% HD 1:01 / 10:47

Outdoor Fisting Gangbang - Past the Elbow Featuring Jasmine_dlight, Hairy Kink Mоther & Roxxie Sweetheart

FapHouse 3 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Sabrina Smiith Private Show - Part 2

4K 2:00 / 23:00

Sabrina Smiith Private Show - Part 2

Flirt4Free 2 months ago

Helena Price Presents - Training Her Tranny Ass With My BBC!!!

55% 4K 0:11 / 57:10

Helena Price Presents - Training Her Tranny Ass With My BBC!!!

Clips4sale 3 years ago

Three busty shemale punishers get their dicks sucked by a dude

Three busty shemale punishers get their dicks sucked by a dude

aShemaleTube 1 year ago

Dimitri Caruso Private Show

HD 2:00 / 13:34

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Troy Khalil Private Show

66% HD 2:00 / 6:40

Troy Khalil Private Show

Flirt4Free 2 years ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 10 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 months ago

Lance & Christian & Master Private Show

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

Jeans Spanking

Flirt4Free 1 year ago

No rights day in da house. Painal for a harrased snowbunny the sissy slut Alina

No rights day in da house. Painal for a harrased snowbunny the sissy slut Alina

xHamster 1 year ago

Submissive sissy guy dressed as a cute girl gets dominated by the nasty TS chick

Submissive sissy guy dressed as a cute girl gets dominated by the nasty TS chick

Tranny.one 4 years ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

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

55% HD 0:39 / 42:45

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

FapHouse 2 months ago

Ruby Daviss Private Show

HD 2:00 / 15:58

Ruby Daviss Private Show

Flirt4Free 2 years ago

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

FapHouse 3 months ago

Sophia Loreen Party on Jan 24, 2026 - Part 7

4K 2:00 / 31:24

Sophia Loreen Party on Jan 24, 2026 - Part 7

Flirt4Free 1 month ago

Sophia Loreen Party on May 15, 2025 - Part 2

59% 4K 2:00 / 22:37

Sophia Loreen Party on May 15, 2025 - Part 2

Flirt4Free 9 months ago

Dominatrix caning useless slave

Dominatrix caning useless slave

Tranny.one 4 years ago

cherry and i dominate our disobedient puppies nyxi and livi

41% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

AnalVids 1 year ago

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

64% HD 1:01 / 7:45

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

FapHouse 1 month ago

Sissy Maid Self Bondage Electro Punishment

Sissy Maid Self Bondage Electro Punishment

xHamster 2 years ago

Lucky dude fucks and gets fucked by a bunch of hot trannies

Lucky dude fucks and gets fucked by a bunch of hot trannies

Fapality 1 year ago

Nikolly Gaucha punishes his partner

Nikolly Gaucha punishes his partner

xHamster 1 year ago

big beautiful woman FTM Love button Punishment Until Squirt

big beautiful woman FTM Love button Punishment Until Squirt

ShemaleSin 1 week ago

Liam Jacobson Private Show

60% HD 2:00 / 7:51

Liam Jacobson Private Show

Flirt4Free 1 year ago

Punishing A Guy Outdoors - Alana Ferreira

Punishing A Guy Outdoors - Alana Ferreira

AbTranny 3 years ago

Anahi Hefner Private Show

HD 2:00 / 39:07

Anahi Hefner Private Show

Flirt4Free 3 years ago

Trans Military Has No Borders

Trans Military Has No Borders

Eporner 11 months ago

Jhordy & Cody & Archie Private Show

57% HD 2:00 / 8:58

Jhordy & Cody & Archie Private Show

Flirt4Free 1 month ago

Live Uncut Sissy Masturbation: Webcam Domination & Ass-toy Cumshot

Live Uncut Sissy Masturbation: Webcam Domination & Ass-toy Cumshot

xHamster 1 month ago

Kendall Penny: Bury Your Face Into My Goddess Hole

Premium 75% HD 51:53

Kendall Penny: Bury Your Face Into My Goddess Hole

Kink 5 years ago

Naughty Boys Get Punished

Naughty Boys Get Punished

xHamster 1 year ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium 56% HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

XVideosRed 1 year ago

Caught Stepbro in Fishnets - Now His Punishment Is Stepbrother’s Huge Cock

Caught Stepbro in Fishnets - Now His Punishment Is Stepbrother’s Huge Cock

FapHouse 3 weeks ago

Futa Punishes Her Step-slut

62% 0:39 / 19:11

Futa Punishes Her Step-slut

FapHouse 1 month ago

secretary caught jerking off

62% HD 0:10 / 39:44

secretary caught jerking off

Clips4sale 2 years ago

Master & Ithan Private Show

56% HD 2:00 / 5:59

Master & Ithan Private Show

Flirt4Free 7 months ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 3 weeks ago

Desire Sweet Private Show

HD 2:00 / 18:06

Desire Sweet Private Show

Flirt4Free 5 months ago

TGirl Threesome Fun

Premium 55% 20:22

TGirl Threesome Fun

APClips 1 year ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

aShemaleTube 5 months ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 4 months ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 2 weeks ago

I can't stop thinking about my best friend's relationship with me

I can't stop thinking about my best friend's relationship with me

xHamster 2 months ago

TS Esther gets fucked by The BBC PUNISHER and takes a nasty facial cumshot

TS Esther gets fucked by The BBC PUNISHER and takes a nasty facial cumshot

aShemaleTube 1 week ago

Troy Khalil Private Show

65% 4K 2:00 / 14:59

Troy Khalil Private Show

Flirt4Free 5 months ago

Femboy Couple Blows Penis Spanks Ass

Femboy Couple Blows Penis Spanks Ass

Tranny.one 4 years ago

How Badly Do You Want to Play with My Belly and Navel?

64% HD 2:00 / 28:26

How Badly Do You Want to Play with My Belly and Navel?

Flirt4Free 2 years ago

Cute Tranny Gal Lactating her Titties after Punishing her Teats with Sex-toy, Clamps and Vacuum Milking Machine

Cute Tranny Gal Lactating her Titties after Punishing her Teats with Sex-toy, Clamps and Vacuum Milking Machine

SortPorn 3 weeks ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Horny shemale Karen Venus punishing a wet pussy

Horny shemale Karen Venus punishing a wet pussy

Tranny.one 5 years ago

”Faustine Lee gets punished”

”Faustine Lee gets punished”

ThePornstar 7 months ago

Sissy Caned by Two Cruel Mistresses

Sissy Caned by Two Cruel Mistresses

xHamster 1 month ago

Bella Nightwish Private Show

65% 2:00 / 4:02

Bella Nightwish Private Show

Flirt4Free 2 months ago

Jepsen Rae Private Show

Jepsen Rae Private Show

Flirt4Free 3 days ago

I'm so overwhelmed right now that I'm trying to make myself feel better

I'm so overwhelmed right now that I'm trying to make myself feel better

xHamster 2 months ago

Elias & Elix Private Show

61% HD 2:00 / 13:10

Elias & Elix Private Show

Flirt4Free 4 months ago

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

56% HD 0:39 / 15:56

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

FapHouse 4 months ago

DOMMY MOMMY COFFINS PUNISHES SABINA

Premium HD 25:06

DOMMY MOMMY COFFINS PUNISHES SABINA

Sheer 3 years ago

Lily Demure Deepthroats

69% HD 1:01 / 30:01

Lily Demure Deepthroats

FapHouse 2 years ago

German TS Surprised by a Creep - as a Punishment, He Is Being Fucked Hard and Pissed on

54% 1:01 / 17:35

German TS Surprised by a Creep - as a Punishment, He Is Being Fucked Hard and Pissed on

FapHouse 2 years ago

Aleex & Paulo Private Show

55% HD 2:00 / 8:12

Aleex & Paulo Private Show

Flirt4Free 9 months ago

I come home and find a tranny who fucked my wife and so I punish her. Full video on my OF Page.

I come home and find a tranny who fucked my wife and so I punish her. Full video on my OF Page.

xHamster 2 months ago

I'm so Excited to Be Able to Take Care of Myself Right Now

I'm so Excited to Be Able to Take Care of Myself Right Now

FapHouse 2 weeks ago

Athletic trans loves painal by bbc

Athletic trans loves painal by bbc

Sheshaft 1 month ago

Kennedy Rose Gets a Donut on her Butthole While Taking 2 Strap-ons

Kennedy Rose Gets a Donut on her Butthole While Taking 2 Strap-ons

Some.Porn 6 months ago

The Reward for the Locked-up Sissy

The Reward for the Locked-up Sissy

xHamster 3 months ago

The Horny Police Officer Is Back to Punish You!

66% HD 1:01 / 14:18

The Horny Police Officer Is Back to Punish You!

FapHouse 1 year ago

TS Playground 12

HD 0:30 / 3:15:00

TS Playground 12

AEBN 11 years ago

Sissyfication 1

58% HD 1:01 / 10:56

Sissyfication 1

FapHouse 10 months ago

Femboy Samus Wedgie and Anal Stretching Punishment with Huge Dildo

Femboy Samus Wedgie and Anal Stretching Punishment with Huge Dildo

xHamster 1 month ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 9 months ago

See the New Slave They Humiliate, Torment & Hard Fist

56% HD 0:39 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year ago

Epic moment from "It's easy to get out in the middle of the night and it's raining"

Epic moment from "It's easy to get out in the middle of the night and it's raining"

xHamster 4 months ago

Sophia Loreen Private Show

61% 4K 2:00 / 4:05

Sophia Loreen Private Show

Flirt4Free 2 months ago

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

xHamster 4 months ago

Verbal Domination + Giant Cumshot

51% HD 2:00 / 21:32

Verbal Domination + Giant Cumshot

Flirt4Free 3 years ago

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

aShemaleTube 1 month ago

Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!

Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!

xHamster 2 years ago

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

xHamster 2 years ago

I Can't Stop Thinking About My Best Friend's Relationship with Me

I Can't Stop Thinking About My Best Friend's Relationship with Me

FapHouse 3 weeks ago

Sissy was shocked at the size the mistress was going to shove up her ass

Sissy was shocked at the size the mistress was going to shove up her ass

xHamster 1 year ago

Lucky man gets gangbanged by the gorgeous TS chicks

Lucky man gets gangbanged by the gorgeous TS chicks

Tranny.one 4 years ago

thaysa carvalho (ts) fucked hard by white boyfriend

thaysa carvalho (ts) fucked hard by white boyfriend

PornOne 3 years ago

Troy Khalil Private Show

HD 2:00 / 15:13

Troy Khalil Private Show

Flirt4Free 2 years ago

Nasty Kigurumi CD: Cord Servitude Cuff Punishment & Intensive Tugjob to Immodest Explosive Spunk fountain

Nasty Kigurumi CD: Cord Servitude Cuff Punishment & Intensive Tugjob to Immodest Explosive Spunk fountain

ShemaleSin 1 month ago

Luccas & Jhordy & Master Private Show

61% HD 2:00 / 14:28

Luccas & Jhordy & Master Private Show

Flirt4Free 1 month ago

t-girl Disciplined chick's cunny

t-girl Disciplined chick's cunny

TrannyGem 5 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 1 year ago

This ladyboy breezy Madeline is vulnerable as she gets stiff penalty from her tormentor

This ladyboy breezy Madeline is vulnerable as she gets stiff penalty from her tormentor

TrannyGem 4 years ago

Sophia Loreen Private Show

4K 2:00 / 29:01

Sophia Loreen Private Show

Flirt4Free 1 week ago

Hard belt self spanking Part 3

Hard belt self spanking Part 3

xHamster 1 year ago

Rough Punishment Fucking

47% HD 2:00 / 9:58

Rough Punishment Fucking

Flirt4Free 1 year ago

Getting ready for serve - Spiked games

Getting ready for serve - Spiked games

xHamster 2 years ago

Executioners

Some.Porn 9 months ago

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

xHamster 1 month ago

Brutus Shows Full Body Naked,flexes,fucks Pillow& Swears As Roleplay

56% HD 2:00 / 11:46

Brutus Shows Full Body Naked,flexes,fucks Pillow& Swears As Roleplay

Flirt4Free 8 years ago

Hanna Ven Private Show

57% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 1 year ago

femout - jill pill portland tranny xmas hardcore sex

femout - jill pill portland tranny xmas hardcore sex

TransDoe 2 years ago

Banged Behind Bars

Banged Behind Bars

Eporner 11 months ago

Adele & Eccatelina Private Show

59% HD 2:00 / 13:33

Adele & Eccatelina Private Show

Flirt4Free 3 years ago

Elix & Elias & Paulo Private Show

64% HD 2:00 / 7:41

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Jamer & Owen & Hercules Private Show

53% HD 2:00 / 10:23

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years ago

Tight Breast Bind Exposed Tgirl Ass Whipped Butt Plugged Femdom Orgasm Punishment

Tight Breast Bind Exposed Tgirl Ass Whipped Butt Plugged Femdom Orgasm Punishment

XVideos 1 year ago

Dom Daddy Punishes Bitch Sexually

70% HD 2:00 / 22:55

Dom Daddy Punishes Bitch Sexually

Flirt4Free 1 year ago

Gaping with Dildo and Plug

Gaping with Dildo and Plug

Flirt4Free 3 years ago

NEW RIKA FOX! The BBC PUNISHER fucks Rika Fox! Full video available now subscribe 😈

NEW RIKA FOX! The BBC PUNISHER fucks Rika Fox! Full video available now subscribe 😈

aShemaleTube 7 months ago

Punishing My Girlcock With a Fleshlight Until I Explode

Punishing My Girlcock With a Fleshlight Until I Explode

ShemaleSin 10 months ago

Bratty Natalie gets punished hard as Penny Barber spank

Bratty Natalie gets punished hard as Penny Barber spank

Eporner 4 months ago

He Rides That Dildo Like a Good Boi

HD 2:00 / 15:57

He Rides That Dildo Like a Good Boi

Flirt4Free 2 years ago

My best friend told me that while he was away I would watch videos of the two of us Clip 1

My best friend told me that while he was away I would watch videos of the two of us Clip 1

xHamster 2 months ago

TS judge punishes the hot guy with a hardcore ass pounding with her huge Tcock

TS judge punishes the hot guy with a hardcore ass pounding with her huge Tcock

Tranny.one 4 years ago

Xxxtranssex Akane 4 - TGirlJapan

Xxxtranssex Akane 4 - TGirlJapan

Tranny.one 4 years ago

Ts samanther as nasty teacher

Ts samanther as nasty teacher

ShemaleSin 2 years ago

”big black dick t-girl Leilani Li assfucking destroys tight booty for sub Sage Roux”

”big black dick t-girl Leilani Li assfucking destroys tight booty for sub Sage Roux”

LesbianBliss 2 weeks ago

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