Punishment Videos (40,310)

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

xHamster 4 months ago

Columbian Boys Wedgie War

48% HD 2:00 / 15:54

Columbian Boys Wedgie War

Flirt4Free 5 months ago

Feelipe & Adara Private Show

62% HD 2:00 / 12:01

Feelipe & Adara Private Show

Flirt4Free 8 months ago

Dustin Hans Private Show

Dustin Hans Private Show

Flirt4Free 3 days ago

Jhordy & Maxx Private Show

66% HD 2:00 / 1:24:58

Jhordy & Maxx Private Show

Flirt4Free 7 months ago

Viky & Master Private Show

60% HD 2:00 / 7:04

Viky & Master Private Show

Flirt4Free 3 months ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Ts gets punished Helpless teenager Kaisey Dean was on her way to witness her grandma but

Ts gets punished Helpless teenager Kaisey Dean was on her way to witness her grandma but

Eporner 2 years ago

Brutus K Private Show

59% HD 2:00 / 6:01

Brutus K Private Show

Flirt4Free 9 years ago

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

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

xHamster 3 months ago

Sophia Loreen Private Show

61% HD 2:00 / 25:48

Sophia Loreen Private Show

Flirt4Free 1 week ago

TS domina punishing her festive bf

TS domina punishing her festive bf

Sheshaft 2 weeks ago

Naughty TGirl maids get bondage and spanking punishment after being caught playing together

Naughty TGirl maids get bondage and spanking punishment after being caught playing together

aShemaleTube 7 years ago

Pervert pigs 2

51% HD 0:39 / 11:02

FapHouse 3 years ago

Headmaster punishes and fucks bound trans student

Headmaster punishes and fucks bound trans student

Sheshaft 1 year ago

Jacob Malik Private Show

63% HD 2:00 / 15:29

Jacob Malik Private Show

Flirt4Free 2 weeks ago

The Most beautiful Trans Tits in the World Pinched and Lactating

The Most beautiful Trans Tits in the World Pinched and Lactating

xHamster 3 months ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

xHamster 1 month ago

La Cherry Spice, Dorian

La Cherry Spice, Dorian

xHamster 11 months ago

Sophia Loreen Private Show

63% HD 2:00 / 10:44

Sophia Loreen Private Show

Flirt4Free 1 year ago

Nicolle & Christian Private Show

63% HD 2:00 / 5:00

Nicolle & Christian Private Show

Flirt4Free 8 months ago

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

TrannyGem 4 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Jhordy & Maxx Private Show

58% HD 2:00 / 7:55

Jhordy & Maxx Private Show

Flirt4Free 7 months ago

Crossdresser Mistress Luci May spanks blonde tranny maid tight ass giving her lovely peachy red bum

Crossdresser Mistress Luci May spanks blonde tranny maid tight ass giving her lovely peachy red bum

SleazyNEasy 8 years ago

Ubeer & Paulo Private Show

62% HD 2:00 / 4:46

Ubeer & Paulo Private Show

Flirt4Free 8 months ago

Cock sounding punishment for pitiful slaves in group session

Cock sounding punishment for pitiful slaves in group session

PornLib 1 month ago

Sophia Loreen Private Show

4K 2:00 / 1:04:35

Sophia Loreen Private Show

Flirt4Free 1 month ago

Troy Khalil Private Show

HD 2:00 / 24:00

Troy Khalil Private Show

Flirt4Free 2 years ago

$Christian\'s Turn to Eject His Cum into Master\'s Mouth$ HD 2:00 / 9:58

Christian\'s Turn to Eject His Cum into Master\'s Mouth

Flirt4Free 3 years ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

xHamster 1 year ago

Sexy Avery Angel gets fucked by The BBC PUNISHER and takes a nasty ! Full video available now 😈

Sexy Avery Angel gets fucked by The BBC PUNISHER and takes a nasty ! Full video available now 😈

aShemaleTube 5 months ago

**** Duo Domme Ballbusting: Unbreakable Sissy Takes Our Hardest Kicks!

**** Duo Domme Ballbusting: Unbreakable Sissy Takes Our Hardest Kicks!

LoyalFans 5 months ago

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

xHamster 4 months ago

TS Natalie Mars fisted and stretched by MILF Penny Barber

TS Natalie Mars fisted and stretched by MILF Penny Barber

UrGayPorn 7 months ago

Soft eggs for breakfast... Ballbusting until cumshot! CBT by cute Tranny Girl

Soft eggs for breakfast... Ballbusting until cumshot! CBT by cute Tranny Girl

xHamster 1 year ago

Brutus K Flexes His Muscles Just for You

HD 2:00 / 14:44

Brutus K Flexes His Muscles Just for You

Flirt4Free 11 years ago

Young Waiter Has To Pay For His Clumsiness By Letting a Sexy Curvy Latina Tranny Fuck Him Hard

Young Waiter Has To Pay For His Clumsiness By Letting a Sexy Curvy Latina Tranny Fuck Him Hard

AnySex 1 year ago

Bukkake #2 the *** 9 T-girls Mass Cumming

48% HD 0:39 / 29:35

Bukkake #2 the *** 9 T-girls Mass Cumming

FapHouse 3 years ago

Cum in the Mouth, Kissing, Fucking and Sucking

59% HD 2:00 / 1:09:57

Cum in the Mouth, Kissing, Fucking and Sucking

Flirt4Free 3 years ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

xHamster 2 years ago

pool game where both players win

pool game where both players win

Tranny.one 4 years ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

FetishShrine 8 months ago

26mins (FULL) Five Mistresses and One Boytoy

26mins (FULL) Five Mistresses and One Boytoy

xHamster 1 year ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 2 weeks ago

Richii Smiith Private Show

4K 2:00 / 10:51

Richii Smiith Private Show

Flirt4Free 1 month ago

Sophia Loreen Private Show

69% HD 2:00 / 5:30

Sophia Loreen Private Show

Flirt4Free 3 years ago

Jamer & Owen & Hercules Private Show

43% HD 2:00 / 54:50

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

[voiced] LOL Futa JOI game with punishment

[voiced] LOL Futa JOI game with punishment

Eporner 1 year ago

Alexander & Patric & Alfonso Private Show

61% HD 2:00 / 1:33:17

Alexander & Patric & Alfonso Private Show

Flirt4Free 3 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 month ago

Hot wax torture for sissy maid

Hot wax torture for sissy maid

xHamster 1 year ago

HOT Trans Avery Angel gets fucked by the BBC PUNISHER and takes a nice facial cumshot

HOT Trans Avery Angel gets fucked by the BBC PUNISHER and takes a nice facial cumshot

aShemaleTube 1 year ago

Zara Clark Private Show

4K 2:00 / 12:12

Zara Clark Private Show

Flirt4Free 2 months ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 2 months ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

xHamster 1 month ago

Figging DP: caning with figged holes

Figging DP: caning with figged holes

FapHouse 3 years ago

More maintenance spanking for Kitsy. OTK punishment.

More maintenance spanking for Kitsy. OTK punishment.

xHamster 1 year ago

”Apolonia & Zoe Doll are going to get punished for being wet down their pants”

”Apolonia & Zoe Doll are going to get punished for being wet down their pants”

ThePornstar 1 year ago

Big clit twitching after being sucked for hours

Big clit twitching after being sucked for hours

Tranny.one 3 years ago

Nicolle & Christian Private Show

63% HD 2:00 / 11:02

Nicolle & Christian Private Show

Flirt4Free 7 months ago

Richii Smiith Private Show

Richii Smiith Private Show

Flirt4Free 1 month ago

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

xHamster 3 weeks ago

ADULT TIME - Hot Public FUTANARI Fuck And Suck! Lauren Phillips, Chloe Surreal, And Hailey Rose!

ADULT TIME - Hot Public FUTANARI Fuck And Suck! Lauren Phillips, Chloe Surreal, And Hailey Rose!

its.PORN 1 year ago

Dionisio & Perseo & Elvis Private Show

53% HD 2:00 / 30:47

Dionisio & Perseo & Elvis Private Show

Flirt4Free 3 years ago

3 tranny mistress with 2 prisoners

65% HD 1:01 / 25:56

3 tranny mistress with 2 prisoners

FapHouse 4 years ago

Charlie Cano Private Show

Charlie Cano Private Show

Flirt4Free 3 years ago

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

AbTranny 4 years ago

Indian Step Father Punishes His Young Step Daughter After He Caught Her Having Sex Her Bf transsexual

Indian Step Father Punishes His Young Step Daughter After He Caught Her Having Sex Her Bf transsexual

Eporner 1 week ago

Jhordy & Maxx Private Show

52% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 7 months ago

Jhon & Derek & Chris Private Show

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Sabrina Smiith Private Show

4K 2:00 / 20:37

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Charlie Cano Private Show

55% HD 2:00 / 7:16

Charlie Cano Private Show

Flirt4Free 3 years ago

JADE 2548

Fapcat 3 years 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 4 months 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 7 months ago

Luccas & Jhordy Private Show

63% HD 2:00 / 7:43

Luccas & Jhordy Private Show

Flirt4Free 7 months ago

Facesitting asian domina punishes her slave

Facesitting asian domina punishes her slave

aShemaleTube 6 years ago

Dude Binds His Buddy to Penalize Him on the Roof

Dude Binds His Buddy to Penalize Him on the Roof

4Gay 1 year ago

Sophia Loreen Private Show

55% 4K 2:00 / 4:43

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

55% HD 0:39 / 25:09

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

FapHouse 7 months ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

Shemale Domination - 15 - Isa Laurens & Rick Bitch

xHamster 2 months ago

Cami Scott Private Show

HD 2:00 / 20:51

Cami Scott Private Show

Flirt4Free 1 year ago

Christian & Nicco & Elvis Private Show

41% HD 2:00 / 19:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Black thrall gets hard whipped by slavemaster then gets crotch roped and waxed on hogtie

Black thrall gets hard whipped by slavemaster then gets crotch roped and waxed on hogtie

Ebony8 7 months ago

Victoria Rousso Private Show

Victoria Rousso Private Show

Flirt4Free 2 years ago

Shemale nun punishes and anal fucks man

Shemale nun punishes and anal fucks man

KeekAss 1 year ago

Sex and Cum with Elias & Elix

34% HD 2:00 / 44:59

Sex and Cum with Elias & Elix

Flirt4Free 7 months ago

Tall redhead shemale punishing a dude's asshole

Tall redhead shemale punishing a dude's asshole

aShemaleTube 1 week ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 2 weeks ago

Ebony trans Leilani Li toys and roughly pounds her new sub

Ebony trans Leilani Li toys and roughly pounds her new sub

UrGayPorn 5 months 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

xHamster 3 weeks ago

Blonde tranny babe and a tattooed guy fuck each other in the bondage porn

Blonde tranny babe and a tattooed guy fuck each other in the bondage porn

Tranny.one 4 years ago

Rubberdomme Fetishplay Part 5 Human Ashtray Maulfotze

Premium 53% 9:35

Rubberdomme Fetishplay Part 5 Human Ashtray Maulfotze

APClips 1 year ago

Smooth Ass Twerk and Cum - Gape

4K 2:00 / 23:23

Smooth Ass Twerk and Cum - Gape

Flirt4Free 7 years ago

Mariana Pardo Private Show

HD 2:00 / 10:01

Mariana Pardo Private Show

Flirt4Free 3 years ago

Teacher Tranny Spanking Guy and Fucking His Ass in Classroom

Teacher Tranny Spanking Guy and Fucking His Ass in Classroom

Tranny.one 4 years ago

Tifany Rodriguez & Joel Pineda Private Show

63% HD 2:00 / 6:35

Tifany Rodriguez & Joel Pineda Private Show

Flirt4Free 2 years ago

Imilia Audley - Futa Mistress Punishes You With A Cummy Bed

Imilia Audley - Futa Mistress Punishes You With A Cummy Bed

ProPorn 1 month ago

Anne Johnsons Private Show

Anne Johnsons Private Show

Flirt4Free 1 week ago

Sandy Lee Private Show

HD 2:00 / 14:26

Sandy Lee Private Show

Flirt4Free 10 years ago

Sophia Loreen Private Show

4K 2:00 / 30:05

Sophia Loreen Private Show

Flirt4Free 8 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

shemale escort fucks guy

shemale escort fucks guy

Eporner 5 years ago

Matt & Elvis & Aron Private Show

Matt & Elvis & Aron Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Jan 15, 2026 - Part 2

4K 2:00 / 34:23

Sophia Loreen Party on Jan 15, 2026 - Part 2

Flirt4Free 1 month ago

Exploring Your Giantess!

Exploring Your Giantess!

LoyalFans 1 year ago

Cum with Free Hands

58% HD 2:00 / 8:27

Cum with Free Hands

Flirt4Free 1 year ago

Naughty Stepson Punished

63% HD 0:10 / 10:03

Naughty Stepson Punished

LoyalFans 1 year ago

Luccas & Jhordy Private Show

52% HD 2:00 / 29:22

Luccas & Jhordy Private Show

Flirt4Free 9 months ago

Beautiful & Sexy Rika Fox gets Fucked by The BBC PUNISHER and takes a nasty facial cumshot

Beautiful & Sexy Rika Fox gets Fucked by The BBC PUNISHER and takes a nasty facial cumshot

aShemaleTube 2 weeks ago

Mikes Hanon Private Show

Mikes Hanon Private Show

Flirt4Free 3 years ago

Asian Ladyboy dominatrix punishing a slave client micro

Asian Ladyboy dominatrix punishing a slave client micro

Sheshaft 2 years ago

Danny & Marcelo & Jesus Private Show

61% HD 2:00 / 5:55

Danny & Marcelo & Jesus Private Show

Flirt4Free 2 years ago

Cataleya Divine Private Show

Cataleya Divine Private Show

Flirt4Free 2 years ago

Office femdom paddling sub on the ground during domination

Office femdom paddling sub on the ground during domination

Some.Porn 1 year 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

Shiny Latex Slave Boy Kinky Anal Masturbation

HD 2:00 / 10:13

Shiny Latex Slave Boy Kinky Anal Masturbation

Flirt4Free 10 years ago

Asian Trans Jerking and Self Sucking

Asian Trans Jerking and Self Sucking

Flirt4Free 8 years ago

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