Chastity Videos - Trans (32,658)

Jacob Malik Private Show

57% HD 2:00 / 8:46

Jacob Malik Private Show

Flirt4Free 7 months ago

Sissy White Boi and His Wife: Strippers for Big Black Daddy - Chapter 1: the Fantasy

53% HD 1:01 / 5:51

Sissy White Boi and His Wife: Strippers for Big Black Daddy - Chapter 1: the Fantasy

FapHouse 3 months ago

He so Wants to Cum, but His Hands and Head Are Shackled!

63% HD 0:39 / 2:18

He so Wants to Cum, but His Hands and Head Are Shackled!

FapHouse 2 years ago

Monica Farell Private Show

Monica Farell Private Show

Flirt4Free 3 years ago

How would I date my Femboy - STORY, VLOG , POV

How would I date my Femboy - STORY, VLOG , POV

Clips4sale 4 days ago

fucking my big sissy ass with massive dildos and a fuckmachine

fucking my big sissy ass with massive dildos and a fuckmachine

AnalVids 2 years ago

Rebeccah Gibson Private Show

HD 2:00 / 27:50

Rebeccah Gibson Private Show

Flirt4Free 2 weeks ago

Princess Chastity Fuckdoll - Three Way Domination of a Submissive Piss Drinking Trans Girl

55% 0:39 / 32:50

Princess Chastity Fuckdoll - Three Way Domination of a Submissive Piss Drinking Trans Girl

FapHouse 3 weeks ago

Milk or Tea?

69% HD 1:01 / 9:43

FapHouse 10 months ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Flirt4Free 1 year ago

Jhordy & Maxx Private Show

51% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Squeeze Me Where?

51% HD 2:00 / 4:08

Squeeze Me Where?

Flirt4Free 6 years ago

Nicco & Michael & Santiago Private Show

53% HD 2:00 / 6:03

Nicco & Michael & Santiago Private Show

Flirt4Free 2 years ago

Trans Pool Party Turns Into All Out Anal Orgy

Premium HD 31:26

Trans Pool Party Turns Into All Out Anal Orgy

XVideosRed 9 months ago

Jessica Bloom's Big Cock Throbs From Anal - Caged and Released Hands-free Squirting Orgasms

HD 1:01 / 22:19

Jessica Bloom's Big Cock Throbs From Anal - Caged and Released Hands-free Squirting Orgasms

FapHouse 7 months ago

Bella Nightwish Party on Jan 10, 2026

Bella Nightwish Party on Jan 10, 2026

Flirt4Free 8 months ago

Sophia Loreen Private Show

53% HD 2:00 / 15:11

Sophia Loreen Private Show

Flirt4Free 5 months ago

Deep Ass-fucking - My Feet Curling in Orgasm

Deep Ass-fucking - My Feet Curling in Orgasm

FapHouse 1 month ago

Premium Galaxy Slave Reina Serves Her Milky Way Sperm

60% HD 1:01 / 34:20

Premium Galaxy Slave Reina Serves Her Milky Way Sperm

FapHouse 8 months ago

Brides Hands-free BBC Cumshots

64% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 4 months ago

Maximo Ston Private Show

Maximo Ston Private Show

Flirt4Free 5 months ago

Desire Sweet Private Show

HD 2:00 / 19:40

Desire Sweet Private Show

Flirt4Free 11 months ago

Roy & Hercules & Jamer Private Show

47% HD 2:00 / 4:09

Roy & Hercules & Jamer Private Show

Flirt4Free 4 years ago

Paul Walkers Private Show

HD 2:00 / 11:18

Paul Walkers Private Show

Flirt4Free 3 months ago

futa dominatrix’s permanent sissification: transforming you into the perfect cockwhore sissy bitch - SD wmv

futa dominatrix’s permanent sissification: transforming you into the perfect cockwhore sissy bitch - SD wmv

Clips4sale 5 days ago

Sissykanisa Ride on a Monster Dildo Part2

Sissykanisa Ride on a Monster Dildo Part2

FapHouse 1 year ago

Asian Cute Twink Femboy Double Cumshot

64% HD 1:01 / 6:28

Asian Cute Twink Femboy Double Cumshot

FapHouse 5 months ago

She Gets Chastity Release Instead Of You

55% HD 0:10 / 8:23

She Gets Chastity Release Instead Of You

LoyalFans 5 months ago

Sophia Loreen Party on May 13, 2026 - Part 3

56% HD 2:00 / 34:53

Sophia Loreen Party on May 13, 2026 - Part 3

Flirt4Free 4 months ago

Patric & Alexander & Lian Private Show

49% HD 2:00 / 1:09:57

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Lance & Christian & Master Private Show

63% HD 2:00 / 13:19

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

QoS sissy squirts cum in chastity while BBC rails her

55% 0:11 / 12:14

QoS sissy squirts cum in chastity while BBC rails her

Clips4sale 2 years ago

Bella Seduction Party on Sep 22, 2023

HD 2:00 / 28:29

Bella Seduction Party on Sep 22, 2023

Flirt4Free 3 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 5 years ago

BRAZILIAN TRANS SLAVE DEEPTHROAT BLOWJOB

Premium HD 10:45

BRAZILIAN TRANS SLAVE DEEPTHROAT BLOWJOB

XVideosRed 9 months ago

Caged Asian Sissy Half Naked

70% HD 0:39 / 4:40

Caged Asian Sissy Half Naked

FapHouse 1 year ago

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

44% HD 0:39 / 3:25

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

FapHouse 9 months ago

Daimond Cooper Private Show

4K 2:00 / 10:56

Daimond Cooper Private Show

Flirt4Free 4 months ago

Jhordy & Maxx Private Show

48% HD 2:00 / 1:47:48

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Colombian Boys Private Show

70% HD 2:00 / 7:02

Colombian Boys Private Show

Flirt4Free 2 years ago

Archie Blossom Private Show

74% HD 2:00 / 11:08

Archie Blossom Private Show

Flirt4Free 6 months ago

Patric & Oliver Private Show

69% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 4 years ago

Scott Carterr & Michael Magno Private Show

46% HD 2:00 / 4:59

Scott Carterr & Michael Magno Private Show

Flirt4Free 3 years ago

Sophia Loreen Private Show

4K 2:00 / 10:52

Sophia Loreen Private Show

Flirt4Free 1 week ago

mean futa Domme pegs you in your diaper - HD

mean futa Domme pegs you in your diaper - HD

Clips4sale 3 years ago

you WONT BELIEVE what this trans girl can fit inside her ASS

69% 4K 0:16 / 13:04

you WONT BELIEVE what this trans girl can fit inside her ASS

Clips4sale 11 months ago

Flat Chastity and Big Dildo

66% HD 1:01 / 18:47

Flat Chastity and Big Dildo

FapHouse 5 months ago

Tasks From Us Cuckolding

HD 0:10 / 11:24

Tasks From Us Cuckolding

LoyalFans 1 week ago

Sophia Loreen Private Show

57% HD 2:00 / 10:44

Sophia Loreen Private Show

Flirt4Free 2 years ago

Viky & Master Private Show

56% HD 2:00 / 7:04

Viky & Master Private Show

Flirt4Free 10 months ago

Triple Femdom Spin The Bottle

Triple Femdom Spin The Bottle

Clips4sale 1 year ago

Active trans Girl Celine Dijjon waiting for Get fuckeck by Me in Hotel

Premium HD 9:10

Active trans Girl Celine Dijjon waiting for Get fuckeck by Me in Hotel

Sheer 1 year ago

Convincing You To Become A Controlled Sissy-Girl (4KUHD MP4)

53% HD 0:31 / 14:50

Convincing You To Become A Controlled Sissy-Girl (4KUHD MP4)

Clips4sale 2 years ago

Dominant Overtaken

69% 0:23 / 32:56

Dominant Overtaken

Clips4sale 2 years ago

Sissy bride chastity - Wedding night tease

50% 0:11 / 12:31

Sissy bride chastity - Wedding night tease

Clips4sale 2 years ago

Marian & Richard Private Show

61% HD 2:00 / 8:10

Marian & Richard Private Show

Flirt4Free 3 weeks ago

Nicco & Patric & Santiago Private Show

55% HD 2:00 / 16:28

Nicco & Patric & Santiago Private Show

Flirt4Free 2 years ago

oiled braceface BBC anal ballbusting and chastity cum

62% 4K 0:12 / 11:12

oiled braceface BBC anal ballbusting and chastity cum

Clips4sale 1 year ago

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 years ago

essa posicao e fatal... faco meu namorado gozar muito rapido e me dar muito leite delirando de prazer

essa posicao e fatal... faco meu namorado gozar muito rapido e me dar muito leite delirando de prazer

PornBox 9 years ago

Tits in Your Face and Black Cock Jerking

HD 2:00 / 10:04

Tits in Your Face and Black Cock Jerking

Flirt4Free 5 years ago

trans in chastity extreme gape with inflateable butt plug

73% 0:13 / 7:16

trans in chastity extreme gape with inflateable butt plug

Clips4sale 1 year ago

Lola Crystals and I Having Some Fun

Lola Crystals and I Having Some Fun

FapHouse 1 week ago

Jacob Malik Private Show

54% HD 2:00 / 4:28

Jacob Malik Private Show

Flirt4Free 7 months ago

active trans girl celine dijjon waiting for get fuckeck by me in hotel

55% 0:27 / 9:10

active trans girl celine dijjon waiting for get fuckeck by me in hotel

AnalVids 1 year ago

gravei meu namorado tirando meu cabaco, ele deixou meu cuzinho todo largo - luana prado

gravei meu namorado tirando meu cabaco, ele deixou meu cuzinho todo largo - luana prado

AnalVids 1 week ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

51% HD 1:01 / 31:09

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

FapHouse 6 months ago

Sissykanisa Ride on a Monster Dildo Part1

Sissykanisa Ride on a Monster Dildo Part1

FapHouse 1 year ago

Paulo & Jose & Sander Private Show

55% HD 2:00 / 7:57

Paulo & Jose & Sander Private Show

Flirt4Free 4 months ago

Sissy Joyce fucked by a Big Black Cock

57% HD 1:01 / 10:04

Sissy Joyce fucked by a Big Black Cock

FapHouse 3 years ago

Sissy Big Black Cock Anal POV

Sissy Big Black Cock Anal POV

FapHouse 4 months ago

Femboy Cumshot

FapHouse 2 months ago

Sophia Loreen Party on Apr 27, 2026 - Part 3

48% HD 2:00 / 28:51

Sophia Loreen Party on Apr 27, 2026 - Part 3

Flirt4Free 5 months ago

The Chastity Fuck

HD 0:39 / 13:07

The Chastity Fuck

FapHouse 5 days ago

Anal Fissting Sissy Slut Deep

64% HD 0:10 / 3:12

Anal Fissting Sissy Slut Deep

LoyalFans 3 years ago

Cowmaid: Wearing Prosthetic Chastity & Creamy Extraction

57% HD 1:01 / 39:04

Cowmaid: Wearing Prosthetic Chastity & Creamy Extraction

FapHouse 2 months ago

Sissyfication 2

67% HD 1:01 / 9:48

Sissyfication 2

FapHouse 1 year ago

Fiquem com os melhores momentos da semana - 40 minutos de muita putaria sem limites

Premium HD 39:27

Fiquem com os melhores momentos da semana - 40 minutos de muita putaria sem limites

XVideosRed 1 year ago

Columbian Boys Wedgie War

57% HD 2:00 / 15:54

Columbian Boys Wedgie War

Flirt4Free 1 year ago

caged sissy rides BBC in pink heels squirts cum out of cage

52% 0:12 / 11:12

caged sissy rides BBC in pink heels squirts cum out of cage

Clips4sale 1 year ago

New Steel Urethra Chastity Cage

New Steel Urethra Chastity Cage

FapHouse 1 year ago

Anal Angels XV - Cherub Chastity

Premium HD 32:54

Anal Angels XV - Cherub Chastity

Sheer 2 years ago

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

56% HD 0:39 / 1:13:02

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

FapHouse 3 weeks ago

Extreme Orgasm

FapHouse 4 months ago

Humiliation, Degradation Ejaculation and Punishment! - Mistress Julia

56% HD 1:01 / 17:16

Humiliation, Degradation Ejaculation and Punishment! - Mistress Julia

FapHouse 1 year ago

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

Premium HD 32:52

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

XNXXGold 9 months ago

Taylor Marin Private Show

HD 2:00 / 24:43

Taylor Marin Private Show

Flirt4Free 1 year ago

Perfect Amateur Tgirl Orgy with 3 Trans Girls and 2 MILFs

53% HD 0:39 / 1:13:52

Perfect Amateur Tgirl Orgy with 3 Trans Girls and 2 MILFs

FapHouse 1 week ago

Feelipe & Adara Private Show

54% HD 2:00 / 8:50

Feelipe & Adara Private Show

Flirt4Free 1 year ago

Paulo & Jose & Sander Private Show

50% HD 2:00 / 10:44

Paulo & Jose & Sander Private Show

Flirt4Free 4 months ago

Fucking with Hammer Drill Machine

59% HD 1:01 / 8:06

Fucking with Hammer Drill Machine

FapHouse 5 months ago

Sophia Loreen Party on Apr 25, 2026 - Part 3

49% HD 2:00 / 1:59:26

Sophia Loreen Party on Apr 25, 2026 - Part 3

Flirt4Free 5 months ago

Archie Blossom Private Show

58% HD 2:00 / 5:06

Archie Blossom Private Show

Flirt4Free 6 months ago

Ambar & Lord Private Show

61% HD 2:00 / 7:24

Ambar & Lord Private Show

Flirt4Free 1 month ago

Flat Chastity Sissy

66% HD 1:01 / 21:45

Flat Chastity Sissy

FapHouse 1 year ago

Wild Sabrina Private Show

49% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 7 years ago

Nicco & Patric & Santiago Have Amazing Threesome

58% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

THE FARMHOUSE - 7 Trans Girl Reverse Gangbang BBC

Premium HD 49:50

THE FARMHOUSE - 7 Trans Girl Reverse Gangbang BBC

XVideosRed 1 month ago

Viky & Emma Private Show

65% HD 2:00 / 5:59

Viky & Emma Private Show

Flirt4Free 8 months ago

Briann & Elvis & Patric Private Show

56% HD 2:00 / 7:04

Briann & Elvis & Patric Private Show

Flirt4Free 3 years ago

Princess Chastity Fuckdoll - three way domination of a submissive piss drinking trans girl

Premium HD 32:44

Princess Chastity Fuckdoll - three way domination of a submissive piss drinking trans girl

Sheer 3 weeks ago

Sissies Belong In Chastity (SD MP4)

60% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 2 years ago

Sophia Loreen Private Show

56% HD 2:00 / 18:04

Sophia Loreen Private Show

Flirt4Free 5 months ago

Master & Ithan & Aleex Private Show

52% HD 2:00 / 38:32

Master & Ithan & Aleex Private Show

Flirt4Free 1 year ago

Sissy Jessica Bloom Spitroast Training with Fucking Machine and Dildos - Anal Sissygasms and Cumswallow

HD 0:39 / 13:03

Sissy Jessica Bloom Spitroast Training with Fucking Machine and Dildos - Anal Sissygasms and Cumswallow

FapHouse 5 months ago

Master & Christian Mckenzie & Christian Rey Private Show

57% HD 2:00 / 39:40

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

TS Nadia Love dominated by Goddess Tangent

67% HD 1:01 / 41:49

TS Nadia Love dominated by Goddess Tangent

FapHouse 5 years ago

Archie Blossom Private Show

51% HD 2:00 / 18:47

Archie Blossom Private Show

Flirt4Free 7 months ago

THE FARMHOUSE - 7 Trans Girl Reverse Gangbang BBC

Premium HD 49:49

THE FARMHOUSE - 7 Trans Girl Reverse Gangbang BBC

Sheer 1 month ago

Purity Cage Domination: Plugged and Teased in Silk Panties

56% 0:30 / 15:47

Purity Cage Domination: Plugged and Teased in Silk Panties

Clips 1 month ago

Femdom Stories #11B: Locked Beneath Your Mistress While She Rides (Animated)

Premium HD 16:54

Femdom Stories #11B: Locked Beneath Your Mistress While She Rides (Animated)

C4S 2 weeks ago

Jhordy & Maxx Private Show

43% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

ride dildo

54% HD 2:00 / 6:53

Flirt4Free 5 years ago

Annabella & Lance Private Show

58% HD 2:00 / 6:48

Annabella & Lance Private Show

Flirt4Free 3 years ago

A Bound Prostate Milking for the Sissy Slave

66% 0:20 / 17:51

A Bound Prostate Milking for the Sissy Slave

Clips4sale 2 years ago

Elvis Rey & Andres & Aron Private Show

73% HD 2:00 / 16:32

Elvis Rey & Andres & Aron Private Show

Flirt4Free 3 years ago

Elias & Elix Private Show

56% HD 2:00 / 14:12

Elias & Elix Private Show

Flirt4Free 1 year ago

Master & Ithan & Aleex Private Show

39% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 1 year ago

Sophia Loreen Party on Jun 18, 2026 - Part 4

61% HD 2:00 / 58:05

Sophia Loreen Party on Jun 18, 2026 - Part 4

Flirt4Free 3 months ago

Marian & Richard Private Show

63% HD 2:00 / 5:29

Marian & Richard Private Show

Flirt4Free 1 week ago

2 3 4 5 6

32,658 results found

Related categories

Crossdressing Strap-On Trans Transvestite Trans Domination Sissy Feminization Trans Fucks Trans Trans Fucks Girl Hermaphrodite Trans Fucks Guy Ladyboy Chastity Cage Tgirl Trans Solo Trans Femboy BBC Femboy 18+ Trans Big Cock Trans BBC (Big Black Cock) Trans Post-Op

Narrow your search

sissy chastity chastity sissygasm chastity cage chastity compilation chastity cum femboy chastity 18+ chastity gangbang chastity sissy flat chastity natalie mars chastity bbc chastity chastity bondage chastity dildo chastity strapon chastity bbc chastity fuck chastity orgasm cum in chastity public chastity bdsm chastity

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.