Chastity Videos - Trans (48,940)

Pink Chastity

HD 0:39 / 35:22

FapHouse 5 months ago

HOTTEST Crossdresser Bailey Wilde in Pink Chastity Fucked Missionary

HOTTEST Crossdresser Bailey Wilde in Pink Chastity Fucked Missionary

XVideos 8 months ago

Pride of My Work: Drooling Blowjob

62% HD 0:39 / 7:32

Pride of My Work: Drooling Blowjob

FapHouse 8 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 7 months ago

Artist Fucks Transgender in Chastity

Artist Fucks Transgender in Chastity

XVideos 1 year ago

Spongebob Fucks Trans in Chastity

Spongebob Fucks Trans in Chastity

XVideos 1 year ago

Model Fucks Hot Trans Woman in Chastity

Model Fucks Hot Trans Woman in Chastity

XVideos 1 year ago

Guy Transformed into Hot Woman as Punishment by Roommate

Guy Transformed into Hot Woman as Punishment by Roommate

XVideos 1 year ago

beautiful milf shemale with big juicy ass getting ready for real cock soon

beautiful milf shemale with big juicy ass getting ready for real cock soon

XVideos 2 years ago

Oiled up Sissy Buns Slam Up Against the Window Riding Her Big Toy

Oiled up Sissy Buns Slam Up Against the Window Riding Her Big Toy

XVideos 1 year ago

jennstarts webcam show - sissy slut, big ass, tranny milf

jennstarts webcam show - sissy slut, big ass, tranny milf

XVideos 2 years ago

big ass tranny milf fucking her ass with big dildos &amp_ cum

big ass tranny milf fucking her ass with big dildos &amp_ cum

XVideos 2 years ago

shemale anal extreme

shemale anal extreme

XVideos 9 months ago

Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom

Sissy Chastity Sissygasm Drinking - Trans Cumslut Jessica Bloom

XVideos 2 years ago

Shulatraaa trany pide que le vean las nalguitas

Shulatraaa trany pide que le vean las nalguitas

XVideos 1 year ago

Police Officer Fucks Tgirl in Chastity

Police Officer Fucks Tgirl in Chastity

XVideos 1 year ago

Celebrity Fucks Tgirl in Chastity

Celebrity Fucks Tgirl in Chastity

XVideos 1 year ago

destroying my big sissy ass with a fuck machine and huge dildos

destroying my big sissy ass with a fuck machine and huge dildos

XVideos 2 years ago

GIRLFRIENDS IN THE ROOM DECIDED TO FUCK IN ANAL. BLONDE FUCKING HER ASS FOR BIG BBS.

GIRLFRIENDS IN THE ROOM DECIDED TO FUCK IN ANAL. BLONDE FUCKING HER ASS FOR BIG BBS.

XVideos 3 years ago

Why are you leaking sissy boi? ?

Why are you leaking sissy boi? ?

XVideos 3 years ago

Want some boipussi-chocolate??

Want some boipussi-chocolate??

XVideos 3 years ago

Slamming a Clippd Trans Girls Prostate Till She Squirts

Slamming a Clippd Trans Girls Prostate Till She Squirts

XVideos 6 months ago

Desire Sweet Private Show

HD 2:00 / 34:33

Desire Sweet Private Show

Flirt4Free 6 months ago

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Eporner 6 months ago

Jaw-dropping moment from "Session in the pillory with Latex Catsuit, PA Chastity, Giant Didildo and Estim"

Jaw-dropping moment from "Session in the pillory with Latex Catsuit, PA Chastity, Giant Didildo and Estim"

xHamster 6 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 5 months ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 7

HD 0:39 / 20:06

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 7

FapHouse 5 months ago

Review: Chastity Cages for Sissies

Review: Chastity Cages for Sissies

xHamster 6 months ago

Daniela Lei locked clit big telescopic toy

Daniela Lei locked clit big telescopic toy

aShemaleTube 6 months ago

a trans gostosinha ataca novamente

a trans gostosinha ataca novamente

PornBox 6 months ago

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

55% HD 0:39 / 23:39

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

FapHouse 5 months ago

Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand

Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand

YouPorn Unknown

Ekaterina Jazmine Private Show

4K 2:00 / 18:09

Ekaterina Jazmine Private Show

Flirt4Free 6 months ago

GRANDE PARA TI

xnxxGold 1 year ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

Clips4sale 6 months ago

Nyxi Leon's Boihole Used in Chastity by Mistress Bailey Love

70% HD 0:08 / 0:40

Nyxi Leon's Boihole Used in Chastity by Mistress Bailey Love

FapHouse 5 months ago

Fucking Sexy Sissy in Chastity - Compilation 2

Fucking Sexy Sissy in Chastity - Compilation 2

FapHouse 5 months ago

Size queen femboy riding XXL tongue with belly bulge! (FemboyRaine) Clip 1

Size queen femboy riding XXL tongue with belly bulge! (FemboyRaine) Clip 1

xHamster 5 months ago

Hard training to be a good sissy slut

Hard training to be a good sissy slut

aShemaleTube 5 months ago

Metallic chastity cage is marvelous uncomfortable, but I still burst with cum due to the anal put in banging me at the same time.

Metallic chastity cage is marvelous uncomfortable, but I still burst with cum due to the anal put in banging me at the same time.

ShemaleSin 5 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 6 months ago

Big Stretch!!

xHamster 6 months ago

Oriental shemale is wearing a chastity, bangs a sex tool and cums multiple times

Oriental shemale is wearing a chastity, bangs a sex tool and cums multiple times

ShemaleSin 6 months ago

sissy t nymph in innocence smashed WET POINT OF VIEW

sissy t nymph in innocence smashed WET POINT OF VIEW

TrannyGem 6 months ago

Diego Phoenix Private Show

4K 2:00 / 13:55

Diego Phoenix Private Show

Flirt4Free 6 months ago

Pinked out chastised Sissy Kenzie Star rides a big dildo

Pinked out chastised Sissy Kenzie Star rides a big dildo

xHamster 6 months ago

Sissy Kanisa Maid Service Ep1: Lock Dick Before Start Work

Sissy Kanisa Maid Service Ep1: Lock Dick Before Start Work

FapHouse 6 months ago

Sissy Cumslut Butt to Throat In Chastity - Anal Climax Training Jess Bloom

Sissy Cumslut Butt to Throat In Chastity - Anal Climax Training Jess Bloom

ShemaleSin 6 months ago

HandsFree Premature Sissygasm - Huge Spunk fountain In Chastity Femboy Crossdressed

HandsFree Premature Sissygasm - Huge Spunk fountain In Chastity Femboy Crossdressed

ShemaleSin 6 months ago

Trans Beauty in Chastity Fucked

Trans Beauty in Chastity Fucked

XVideos 1 year ago

Trans in Chastity Fucked Raw - Compilation 3

Trans in Chastity Fucked Raw - Compilation 3

xHamster 6 months ago

Emotional moment from "Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow"

Emotional moment from "Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow"

xHamster 6 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 6 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 5 months ago

your tomboy girlfriend turns out to be a femboy

your tomboy girlfriend turns out to be a femboy

ShemaleSin 6 months ago

a trans gostosinha ataca novamente

Premium HD 13:21

a trans gostosinha ataca novamente

XVideosRed 6 months ago

Railing my enormous STALLION dressed in my fantastic high high-heeled shoes

Railing my enormous STALLION dressed in my fantastic high high-heeled shoes

TrannyGem 5 months ago

Sexy Pissing In Chastity Outdoors in the Public Park Clip 2

Sexy Pissing In Chastity Outdoors in the Public Park Clip 2

xHamster 5 months ago

Using my gfs massager while railing my large butt-plug

Using my gfs massager while railing my large butt-plug

TrannyGem 5 months ago

Fucking Mtf Chastity Charlie 2

Fucking Mtf Chastity Charlie 2

FapHouse 6 months ago

Pissing Chastity Cage

Pissing Chastity Cage

FapHouse 5 months ago

Sara & Elver Private Show

61% HD 2:00 / 14:48

Sara & Elver Private Show

Flirt4Free 5 months ago

Large Sissy Fate Compilation 1

Large Sissy Fate Compilation 1

TrannyGem 5 months ago

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

aShemaleTube 5 months ago

Home Pegging Cumming Sluts

70% 0:39 / 11:50

Home Pegging Cumming Sluts

FapHouse 5 months ago

Trans Housewife cheats with BBC Lover

HD 0:10 / 20:06

Trans Housewife cheats with BBC Lover

LoyalFans 5 months ago

POV Blowjob by step daughter who seduces you into being her cuckold bitch step dad and suck out the creampies from her pussy and locks you in chastity

POV Blowjob by step daughter who seduces you into being her cuckold bitch step dad and suck out the creampies from her pussy and locks you in chastity

XVideos 6 years ago

Jess Bloom Rides Dildos And Swallows Her Own Load of Sissygasm Cum With Booty To Throat

Jess Bloom Rides Dildos And Swallows Her Own Load of Sissygasm Cum With Booty To Throat

ShemaleSin 7 months ago

Trans Woman in Chastity Fucked Hard - Compilation 5

64% HD 0:39 / 20:10

Trans Woman in Chastity Fucked Hard - Compilation 5

FapHouse 7 months ago

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

66% 1:01 / 18:20

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

FapHouse 7 months ago

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

XVideos 7 years ago

Ray Ayanashi japanese slave crossdresser chastity-belt

Ray Ayanashi japanese slave crossdresser chastity-belt

XVideos 7 years ago

White Sissy slave in steel chastity deepthroats and tongues &#039_s ass.Sissyann

White Sissy slave in steel chastity deepthroats and tongues &#039_s ass.Sissyann

XVideos 8 years ago

Sissy Laura - Cumming With A BBC In My Ass (Cumshot)

Sissy Laura - Cumming With A BBC In My Ass (Cumshot)

XVideos 10 years ago

Sissy boi rides BBC makes cummies

Sissy boi rides BBC makes cummies

XVideos 9 years ago

Mamou avec Rachelle Karol je domine une jolie soumise avant de la prendre en levrette ba2.4

Mamou avec Rachelle Karol je domine une jolie soumise avant de la prendre en levrette ba2.4

XVideos 7 months ago

Valentina Ramirezz Private Show

Valentina Ramirezz Private Show

Flirt4Free 7 months ago

Chastity Advise for Sissies

Chastity Advise for Sissies

xHamster 7 months ago

Hot Blonde Crossdresser in Chastity Fucked

Hot Blonde Crossdresser in Chastity Fucked

XVideos 7 months ago

voce nao vai acreditar quem esta por tras dessa transa

voce nao vai acreditar quem esta por tras dessa transa

PornBox 7 months ago

Asian Sissy Deepthroat in Chastity & Lingerie

Asian Sissy Deepthroat in Chastity & Lingerie

xHamster 6 months ago

Trine Larsen 2025 The tour 7 Pink in the stink & pink leather

Trine Larsen 2025 The tour 7 Pink in the stink & pink leather

aShemaleTube 6 months ago

Sissy in Chastity Take BBC Dildo Anal

Sissy in Chastity Take BBC Dildo Anal

FapHouse 6 months ago

Desire Sweet Private Show

66% HD 2:00 / 5:46

Desire Sweet Private Show

Flirt4Free 6 months ago

Trans Woman in Chastity Fucked Hard - Compilation 8

Trans Woman in Chastity Fucked Hard - Compilation 8

xHamster 7 months ago

I Cant wait To Take Your shelady Chastity

I Cant wait To Take Your shelady Chastity

TransTube.tv 6 months ago

Sissy in chastity anal training with monster dildo , massive sex toy and vibration head

Sissy in chastity anal training with monster dildo , massive sex toy and vibration head

ShemaleSin 7 months ago

Sissy Merve Chastity DoggyStyle Fucked BBC Anal Cum BDSM Cum Last Tattoo Blonde Sexy Tgirl Femboy Stockings Hells Part 5

Sissy Merve Chastity DoggyStyle Fucked BBC Anal Cum BDSM Cum Last Tattoo Blonde Sexy Tgirl Femboy Stockings Hells Part 5

xHamster 6 months ago

Luna Florez Private Show

4K 2:00 / 12:41

Luna Florez Private Show

Flirt4Free 6 months ago

Ep2 Testing My New Sissy: Cocksucker and Anal Fingering Training - Mistress Julia

Ep2 Testing My New Sissy: Cocksucker and Anal Fingering Training - Mistress Julia

FapHouse 6 months ago

Sissy femboy degrades herself and pounds herself foolish

Sissy femboy degrades herself and pounds herself foolish

TrannyGem 6 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 6 months ago

StephanieXClover desperate shemale

StephanieXClover desperate shemale

XVideos 7 years ago

M&aacute_s entrenamiento para m&iacute_ culito

M&aacute_s entrenamiento para m&iacute_ culito

XVideos 7 years ago

Sissy Oksana riding purple monster dildo Cumshot part.4

Sissy Oksana riding purple monster dildo Cumshot part.4

XVideos 8 years ago

Sissy Oksana riding dildo with a dick in a cage Cumshot

Sissy Oksana riding dildo with a dick in a cage Cumshot

XVideos 7 years ago

said good sissy slut should recycle her own piss.

said good sissy slut should recycle her own piss.

XVideos 9 years ago

white boi watching bbc vidoes caged

white boi watching bbc vidoes caged

XVideos 9 years ago

Sissy Maid Sucking and Riding Her Sex Doll with Bondage

60% HD 1:01 / 29:30

Sissy Maid Sucking and Riding Her Sex Doll with Bondage

FapHouse 7 months ago

TRANSEI GOSTOSO COM MEU CUNHADO NO SOFÁ - LUANA PRADO

Premium HD 29:04

TRANSEI GOSTOSO COM MEU CUNHADO NO SOFÁ - LUANA PRADO

Sheer 7 months ago

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

xHamster 7 months ago

mamou avec rachelle karol je domine une jolie soumise avant de la prendre en levrette partie 2

HD 0:30 / 12:53

mamou avec rachelle karol je domine une jolie soumise avant de la prendre en levrette partie 2

PornBox 7 months ago

Crossdresser Foot Worship

Crossdresser Foot Worship

XVideos 14 years ago

its incredible how that ass swallows 10 inches in such a lovely way

Premium HD 17:14

its incredible how that ass swallows 10 inches in such a lovely way

xnxxGold 1 month ago

sissy chastity begs deepthroat beneath iron restraints

sissy chastity begs deepthroat beneath iron restraints

YouPorn Unknown

Rough Pegging in Latex

HD 0:39 / 20:23

Rough Pegging in Latex

FapHouse 3 weeks ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 3 weeks ago

Hot Blonde Crossdresser in Chastity Fucked

Hot Blonde Crossdresser in Chastity Fucked

XVideos 1 month ago

Sissy pluged playing in Garage

HD 0:39 / 11:50

Sissy pluged playing in Garage

FapHouse 1 month ago

Naughty free little strip

Naughty free little strip

XVideos 1 month ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 1 month ago

Twelve daily anal destruction

Premium HD 34:38

Twelve daily anal destruction

XVideosRed 1 month ago

Sissy Dee likes to play with herself when she should be doing her duties, Mistress decides to join in Clip 1

Sissy Dee likes to play with herself when she should be doing her duties, Mistress decides to join in Clip 1

xHamster 1 month ago

Caged punk femboy puts a ass-plug in

Caged punk femboy puts a ass-plug in

ShemaleSin 1 month ago

Rebeccah Gibson Private Show

HD 2:00 / 14:47

Rebeccah Gibson Private Show

Flirt4Free 1 month ago

Astolfo Fucking his Trap Pussy

Astolfo Fucking his Trap Pussy

Pornzona 1 month ago

Sissy Femboy Sexy Solo

Sissy Femboy Sexy Solo

DeegX 2 years ago

Pornify my life: becoming your chastity maid

Pornify my life: becoming your chastity maid

ShemaleSin 1 month ago

the intense pleasure of a deep fuck fills her with an overwhelming desire for more

the intense pleasure of a deep fuck fills her with an overwhelming desire for more

PornBox 1 month ago

”Sexy Tranny Chelsea Marie locks Sherman down then pounds his booty”

”Sexy Tranny Chelsea Marie locks Sherman down then pounds his booty”

429Men 3 months ago

81 82 83 84 85

48,940 results found

Related categories

Trans Domination Strap-On Trans Transvestite Crossdressing Sissy Trans Fucks Trans Feminization Trans Fucks Girl Hermaphrodite Chastity Cage Trans Fucks Guy Ladyboy Trans Femboy 18+ Trans Solo Tgirl Trans Post-Op Trans Big Cock Self Facial Futanari

Narrow your search

chastity cage chastity bbc chastity cum femboy chastity 18+ sissy chastity bbc chastity chastity fuck permanent chastity trans chastity chastity sissy cum in chastity chastity anal chastity orgasm chastity gangbang chastity strapon ella hollywood chastity asian chastity chastity belt chastity dildo chastity training

Categories Pornstars

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.