Punish Videos (60,806)

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

72% HD 0:39 / 11:02

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

FapHouse 6 months ago

Mike Swift & David Golden Private Show

64% HD 2:00 / 14:34

Mike Swift & David Golden Private Show

Flirt4Free 2 weeks ago

Futa Punishes Her Step-slut

59% 0:39 / 19:11

Futa Punishes Her Step-slut

FapHouse 7 months ago

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

61% HD 1:01 / 28:08

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

FapHouse 6 months ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

XHamster 7 months ago

Lika Kai Party on Jul 16, 2026 - Part 2

55% 4K 2:00 / 15:57

Lika Kai Party on Jul 16, 2026 - Part 2

Flirt4Free 1 month ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

52% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 7 months ago

Black Tgirls: Mistress Venom's Amazing Cumshot

58% HD 0:39 / 18:23

Black Tgirls: Mistress Venom's Amazing Cumshot

FapHouse 6 months ago

Teaching My Trans Stepsister How To Fuck - TGIRLS HOUSE

Teaching My Trans Stepsister How To Fuck - TGIRLS HOUSE

XHamster 1 month ago

Paulo & Jose & Sander Private Show

57% HD 2:00 / 15:24

Paulo & Jose & Sander Private Show

Flirt4Free 2 months ago

Lily Demure Deepthroats

Lily Demure Deepthroats

XHamster 7 months ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Jhordy & Maxx Private Show

54% HD 2:00 / 24:38

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

The Papi Chulo BBC Fisted Me Deep Until I Came

The Papi Chulo BBC Fisted Me Deep Until I Came

XHamster 5 months ago

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

XHamster 2 years ago

Leggy tranny domina punishing a dude to creampie

Leggy tranny domina punishing a dude to creampie

AShemaleTube 2 weeks ago

Naughty Neighbor Gets Busted

Naughty Neighbor Gets Busted

Some.Porn 11 months ago

Black Man With Huge Penis Punishes Internal Ejaculation

Black Man With Huge Penis Punishes Internal Ejaculation

ShemaleSex 3 weeks ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 3 years ago

Busty TS chick dominates a hogtied submissive masked man

Busty TS chick dominates a hogtied submissive masked man

Tranny.one 4 years ago

Sophia Loreen Private Show

52% HD 2:00 / 18:41

Sophia Loreen Private Show

Flirt4Free 2 months ago

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

ShemaleSex 1 month ago

Dani Saenz Private Show

59% HD 2:00 / 33:18

Dani Saenz Private Show

Flirt4Free 4 years ago

Lisan & Mine Private Show

66% 4K 2:00 / 23:47

Lisan & Mine Private Show

Camster 2 weeks ago

Lily Demure Deepthroats

Lily Demure Deepthroats

XHamster 6 months ago

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

XHamster 4 months 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 1 year ago

Colombian Boys Private Show

48% HD 2:00 / 7:59

Colombian Boys Private Show

Flirt4Free 2 years ago

Sophie Fantasy Private Show

HD 2:00 / 22:02

Sophie Fantasy Private Show

Flirt4Free 1 month ago

This cute asian ladyboy needs a real hard punishement

This cute asian ladyboy needs a real hard punishement

Sheshaft 6 years ago

Sophia Loreen Private Show

4K 2:00 / 11:45

Sophia Loreen Private Show

Camster 3 weeks ago

Sophia Loreen Party on Sep 7, 2026 - Part 3

Sophia Loreen Party on Sep 7, 2026 - Part 3

Flirt4Free 3 days ago

Patric & Simon & Frederick Private Show

54% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

Four shemale punishers in black leather outfits manhandle a

Four shemale punishers in black leather outfits manhandle a

XHamster 2 years ago

Hot Early Footage of Pornstar Holly Parker

Hot Early Footage of Pornstar Holly Parker

XHamster 3 weeks ago

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

Flirt4Free 2 years ago

Sophia Loreen Private Show

4K 2:00 / 10:50

Sophia Loreen Private Show

Camster 3 days ago

Leather outfit ts domina punishes her slave s ass and m

Leather outfit ts domina punishes her slave s ass and m

FetishShrine 2 months ago

Sophia Loreen Party on Aug 22, 2026 - Part 3

64% 4K 2:00 / 1:33:22

Sophia Loreen Party on Aug 22, 2026 - Part 3

Flirt4Free 2 weeks ago

Sophia Loreen Private Show - Part 3

66% 4K 2:00 / 6:09

Sophia Loreen Private Show - Part 3

Flirt4Free 1 year ago

Wearing to cross dress

Wearing to cross dress

XHamster 1 year ago

Jenna Reid Spanks Her French Maid Cross Dressing Cuckold

61% HD 1:01 / 33:29

Jenna Reid Spanks Her French Maid Cross Dressing Cuckold

FapHouse 3 years ago

Why I Should Be Punished

Why I Should Be Punished

XHamster 1 week ago

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

XHamster 10 months ago

sissy college girls get back at their mean coach

69% HD 1:01 / 38:51

sissy college girls get back at their mean coach

FapHouse 4 years ago

Lika Kai Private Show

4K 2:00 / 27:22

Lika Kai Private Show

Flirt4Free 1 week ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 1 year ago

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Tranny.one 4 years ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

CBT Genital Rubber Band Torture and Ruined Orgasm of Trans Slut

CBT Genital Rubber Band Torture and Ruined Orgasm of Trans Slut

XHamster 2 years ago

”Assfucking Punishment for Submissive Sluts on the Upper Floor”

”Assfucking Punishment for Submissive Sluts on the Upper Floor”

TransHero 9 months ago

Sophia Loreen Party on Aug 21, 2026 - Part 6

61% 4K 2:00 / 54:49

Sophia Loreen Party on Aug 21, 2026 - Part 6

Camster 2 weeks ago

Unbelievable double dildo punishment Fuck

Unbelievable double dildo punishment Fuck

AShemaleTube 2 weeks ago

Ride for a Ride

Ride for a Ride

Some.Porn 10 months ago

Sophia Loreen Party on Aug 21, 2026 - Part 6

4K 2:00 / 54:49

Sophia Loreen Party on Aug 21, 2026 - Part 6

Flirt4Free 2 weeks ago

Slave rental

XHamster 1 year ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Sophia Loreen Shows Her Wonderful Body and That Beautiful Backside

Sophia Loreen Shows Her Wonderful Body and That Beautiful Backside

Flirt4Free 4 years ago

Big-titted MILF pounded by stunningTS

Big-titted MILF pounded by stunningTS

Some.Porn 1 year ago

Viky & Master Private Show

66% HD 2:00 / 10:29

Viky & Master Private Show

Camster 9 months ago

Sophia Loreen Party on Jul 17, 2026 - Part 4

HD 2:00 / 1:01:12

Sophia Loreen Party on Jul 17, 2026 - Part 4

Flirt4Free 1 month ago

Mistress Trap Punishment

Mistress Trap Punishment

AShemaleTube 1 year ago

Harris Morrison Private Show

66% 4K 2:00 / 6:17

Harris Morrison Private Show

Flirt4Free 1 week ago

Punished In Place 2: featuring Livi Doll

Premium HD 27:39

Punished In Place 2: featuring Livi Doll

XVideosRed 2 years ago

Crossdressed twink fucked bareback by straight curious Arab

Crossdressed twink fucked bareback by straight curious Arab

Tranny.one 3 years ago

Sophia Loreen Party on Sep 4, 2026 - Part 2

4K 2:00 / 54:21

Sophia Loreen Party on Sep 4, 2026 - Part 2

Camster 5 days ago

3some with Two Shemale Tops

3some with Two Shemale Tops

Pervclips 1 week ago

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

XHamster 2 weeks ago

Skinny ts punished by BBC

Skinny ts punished by BBC

KeekAss 3 months ago

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

55% HD 0:39 / 39:21

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

FapHouse 5 months ago

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Tranny.one 4 years ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Camster 2 months ago

Hot White Dress

Hot White Dress

Flirt4Free 5 months ago

Getting Punished for Braking in the Apartments

54% 1:01 / 32:23

Getting Punished for Braking in the Apartments

FapHouse 5 months ago

Spanked while chained up in the Mrs Playroom

Spanked while chained up in the Mrs Playroom

Tranny.one 4 years ago

Cute Trans Elastic Mommy Tit Slap and Lactating after Pumping her Tits with Vacuum Milking Machine

Cute Trans Elastic Mommy Tit Slap and Lactating after Pumping her Tits with Vacuum Milking Machine

XHamster 3 weeks ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 9 months ago

Piss Pump With Enema Option

Piss Pump With Enema Option

XHamster 3 years ago

Sophia Loreen Private Show

65% HD 2:00 / 4:58

Sophia Loreen Private Show

Flirt4Free 3 months ago

3some with Two Shemale Tops

3some with Two Shemale Tops

Katestube 1 week ago

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

67% 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

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

XHamster 5 months ago

Robber gets punished with some hardcore anal pounding by the horny TS chick

Robber gets punished with some hardcore anal pounding by the horny TS chick

Tranny.one 4 years ago

Dudes caught transexual and punished him orally and anally

Dudes caught transexual and punished him orally and anally

Tranny.one 9 years ago

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

XHamster 1 year ago

futa step-sis makes you her slave - punishment painal, slapping, spitting - SD

futa step-sis makes you her slave - punishment painal, slapping, spitting - SD

Clips4sale 3 years ago

Julia ebony sex doll slave blonde bobcut

Julia ebony sex doll slave blonde bobcut

XHamster 1 week ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Mission to Orgasm

Mission to Orgasm

Some.Porn 10 months ago

Whiping It out Through My Nerdy Shirt

Whiping It out Through My Nerdy Shirt

Flirt4Free 2 years ago

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

Tranny.one 4 years ago

Sophia Loreen Private Show

67% HD 2:00 / 7:25

Sophia Loreen Private Show

Camster 1 month ago

Sensually Milking & Edging Trans Cock

63% HD 0:10 / 14:44

Sensually Milking & Edging Trans Cock

LoyalFans 2 years ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Sophia Loreen Party on Jul 29, 2026 - Part 3

54% 4K 2:00 / 1:17:55

Sophia Loreen Party on Jul 29, 2026 - Part 3

Camster 1 month ago

Pledge and get spot for my group show..start now!!

60% HD 2:00 / 19:52

Pledge and get spot for my group show..start now!!

Flirt4Free 7 years ago

Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad

Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad

Tranny.one 4 years ago

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Tranny.one 4 years ago

Sensually Milking & Edging Trans Cock

74% 0:25 / 14:43

Sensually Milking & Edging Trans Cock

Clips4sale 2 years ago

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

57% 1:01 / 17:41

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

FapHouse 3 years ago

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

XHamster 3 months ago

The teacher wants the cock of the young TS Larissa

The teacher wants the cock of the young TS Larissa

XHamster 4 years ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

XHamster 9 months ago

Shemale Punishes Her Puffy Nipples Until Lactation

65% HD 1:01 / 5:40

Shemale Punishes Her Puffy Nipples Until Lactation

FapHouse 1 year ago

Hanna Ven Private Show

64% HD 2:00 / 10:55

Hanna Ven Private Show

Flirt4Free 2 years ago

Bhabhi Punished her Shemale Cock

Bhabhi Punished her Shemale Cock

XHamster 1 month ago

Sophia Loreen Private Show

4K 2:00 / 12:04

Sophia Loreen Private Show

Camster 4 weeks ago

Hot Ebony Baddie TS 5F61 Gets Punished & Loves It

Hot Ebony Baddie TS 5F61 Gets Punished & Loves It

Eporner 8 months ago

Four shemale dominas fucks a guy with a mask and give him

Four shemale dominas fucks a guy with a mask and give him

XHamster 1 year ago

Anabel Fiofilova Private Show

Anabel Fiofilova Private Show

Camster 3 weeks ago

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Tranny.one 4 years ago

”Babe deep throat sucks in public”

”Babe deep throat sucks in public”

TransHero 8 months ago

School teenie Practices Painfull Sensation

School teenie Practices Painfull Sensation

GayDudesFucking 1 year ago

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

BeMyHole 6 years ago

Sophia Loreen Party on Sep 8, 2026 - Part 4

4K 2:00 / 49:05

Sophia Loreen Party on Sep 8, 2026 - Part 4

Camster 2 days ago

Trans All Girl Dominance. Restrain Bondage, Electro Ass Fucking and Deep-Throat Jobs.

Trans All Girl Dominance. Restrain Bondage, Electro Ass Fucking and Deep-Throat Jobs.

TrannyGem 7 years ago

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

XHamster 7 months ago

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Tranny.one 4 years ago

Gia Darling and Her Scrub Brush

Gia Darling and Her Scrub Brush

XHamster 1 year ago

1 2 3 4 5

60,806 results found

Narrow your search

stepmom punish punish teen 18+ mom punish punish mom lesbian punish stepdad punish punish stepdaughter strapon punish teen punish 18+ anal punish punish fuck punish teens 18+ teacher punish punish anal school punish punish wife victor punish step daughter punish alanah rae punish briana banks punish

Categories Pornstars

Parents

Pornmd.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.