Chastity Videos - Trans (37,183)

Chastity Slave Trans Takes BBC

Chastity Slave Trans Takes BBC

Eporner 1 week ago

White Sissy Trans With Chastity Creampied

White Sissy Trans With Chastity Creampied

AShemaleTube 1 week ago

Chastity TS Vs BBC

Chastity TS Vs BBC

BeMyHole 2 years ago

Pigtailed Trans Cutie With Chastity

Pigtailed Trans Cutie With Chastity

Eporner 2 weeks ago

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

GayCK 4 years ago

AB106 Conpletely domesticated kinky sissy slave- face sitting cum shot edging (Asian and English su

AB106 Conpletely domesticated kinky sissy slave- face sitting cum shot edging (Asian and English su

MyTransfix 1 week ago

Sissy CD in Chastity, Deep Fuck,Huge Dildos, Epic Handsfree Sissygasms, Cleanup.

Sissy CD in Chastity, Deep Fuck,Huge Dildos, Epic Handsfree Sissygasms, Cleanup.

Itsrealamateurs 1 month ago

Who's the Real stepdaddy with Jenny Flowers

Who's the Real stepdaddy with Jenny Flowers

ShemaleSin 2 weeks ago

Caged Femboy Brings Himself to Cum with a Magic Wand

Caged Femboy Brings Himself to Cum with a Magic Wand

XHamster 2 years ago

DOING A TRIP OF MY FIGURE WHILE I EJACULATION WITH A FUCKTOY YOU MANAGE - ACCOMPLISH IN CRIMSON - ARYA SANTANA

DOING A TRIP OF MY FIGURE WHILE I EJACULATION WITH A FUCKTOY YOU MANAGE - ACCOMPLISH IN CRIMSON - ARYA SANTANA

TrannyGem 1 week ago

Itty Bitty Sissy Breeding

Itty Bitty Sissy Breeding

Eporner 2 months ago

DAP in grey PU dress

DAP in grey PU dress

AShemaleTube 1 week ago

Sissy Milking

XHamster 3 months ago

Trans Pool Soiree Turns Into Ass fucking Intercourse With Tons of Jizm

Trans Pool Soiree Turns Into Ass fucking Intercourse With Tons of Jizm

KeekAss 6 months ago

Rectal TGirl Gang Lovemaking Pool Soiree Fuck-a-thon With Ria Bentley

Rectal TGirl Gang Lovemaking Pool Soiree Fuck-a-thon With Ria Bentley

Transvids.tv 1 year ago

Sissy girl drips cum in chastity

Sissy girl drips cum in chastity

XHamster 5 years ago

Chastity Fuckdoll - Nyxi Leon

Chastity Fuckdoll - Nyxi Leon

AShemaleTube 1 week ago

DustiBunni Evelyns Chastity Training - Update One

DustiBunni Evelyns Chastity Training - Update One

Nuvid 1 week ago

Toying in chastity cage sissy tranny

Toying in chastity cage sissy tranny

Lesbian8 1 year ago

Pigtailed Trans Cutie With Chastity

Pigtailed Trans Cutie With Chastity

AShemaleTube 1 week ago

45 Minutes of Sissy Ass Fuck Machine Pounding

45 Minutes of Sissy Ass Fuck Machine Pounding

XHamster 3 months ago

Crazy duo invited a trans chick for a 3some - accomplish in crimson - Alice Hael

Crazy duo invited a trans chick for a 3some - accomplish in crimson - Alice Hael

Tranny.one 3 months ago

Hot Sissy Locked In Chastity

Hot Sissy Locked In Chastity

Eporner 2 months ago

Kylie Maria in kylies chastity slave

Kylie Maria in kylies chastity slave

DrTuber 2 years ago

Sissy In Chastity Fucked Doggystyle

Sissy In Chastity Fucked Doggystyle

Eporner 3 weeks ago

21yo stepson barebacked in taboo 3some by daddy

21yo stepson barebacked in taboo 3some by daddy

Some.Porn 1 year ago

Chastity Fuckdoll Reverse Gangbang

Chastity Fuckdoll Reverse Gangbang

Eporner 10 months ago

Boot Licking Sissy Maid

Boot Licking Sissy Maid

XHamster 4 days ago

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

AShemaleTube 1 year ago

[SISSY] I had him finish off in my jaws in a park in the daytime.

[SISSY] I had him finish off in my jaws in a park in the daytime.

TransTube.tv 1 year ago

Femboy Moans From Getting Railed

Femboy Moans From Getting Railed

XHamster 3 weeks ago

Bianca Black Destroys Worst Beta Male Sydney Summers Chokes On Strapon

Bianca Black Destroys Worst Beta Male Sydney Summers Chokes On Strapon

JuicyTrans 2 weeks ago

Sassyjirin - Locked In My Chastity Cage And Teasing With My Anal Toy

Sassyjirin - Locked In My Chastity Cage And Teasing With My Anal Toy

AbTranny 10 months ago

Chastity TS thanks daddy for the fur coat

Chastity TS thanks daddy for the fur coat

Eporner 1 year ago

Feminization: Your fresh life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

Feminization: Your fresh life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

MyTransfix 1 week ago

Anal Adventures - Fill Me Up, Dad

Anal Adventures - Fill Me Up, Dad

ShemaleSin 1 week ago

Crossdresser in Chastity Fucked Raw

Crossdresser in Chastity Fucked Raw

AShemaleTube 4 days ago

Crossdresser Gets Strapon by Femdom

Crossdresser Gets Strapon by Femdom

Eporner 6 years ago

Femslut cums in cage

Femslut cums in cage

AShemaleTube 2 months ago

Putting big dick in flat chastity cage with penis plug

Putting big dick in flat chastity cage with penis plug

XHamster 1 month ago

Trans Angels - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

Trans Angels - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

Pornzona 2 weeks ago

Femdom owns Sissies

Femdom owns Sissies

Eporner 11 months ago

Femboy Chastity Fuckdoll

Femboy Chastity Fuckdoll

Eporner 4 months ago

Father bonks Natasha Magenta

Father bonks Natasha Magenta

Transvids.tv 9 months ago

Locked in My Chastity

Locked in My Chastity

XHamster 2 months ago

Trans girls look the best with chastity on and BBC up her ass

Trans girls look the best with chastity on and BBC up her ass

Eporner 2 months ago

sissy wench performs trans dreams with toys

sissy wench performs trans dreams with toys

ShemaleSin 5 days ago

Chastity TS Vs BBC

Chastity TS Vs BBC

Eporner 1 year ago

Cute Sissy In Chastity Compilation

Cute Sissy In Chastity Compilation

Eporner 2 months ago

Sabina Steele Aj Fresh Chastity Angel Anal Creampie Bbc Dgs

Sabina Steele Aj Fresh Chastity Angel Anal Creampie Bbc Dgs

Eporner 2 years ago

How I became a bbc addict

How I became a bbc addict

AShemaleTube 1 year ago

Chastity Whore doggy style Pounding (Chastity Charli)

Chastity Whore doggy style Pounding (Chastity Charli)

ShemaleSin 1 week ago

Femdom bangs bimbo sissy cd doxy in booty w/ unicorn sex-toy in chastity makes femboy ride BBC part 2/5

Femdom bangs bimbo sissy cd doxy in booty w/ unicorn sex-toy in chastity makes femboy ride BBC part 2/5

ShemaleSin 3 years ago

Chastity Fuckdoll

Chastity Fuckdoll

BeMyHole 1 month ago

Emily Rose Ts teaches his sissy maid how to pleasure himself with a French maid's help

Emily Rose Ts teaches his sissy maid how to pleasure himself with a French maid's help

GayX 2 months ago

Damn! Shelby is a Desperate, Horny Sissy Maid!

Damn! Shelby is a Desperate, Horny Sissy Maid!

XHamster 1 day ago

Sissy Crossdresser Locked in Chastity POV

Sissy Crossdresser Locked in Chastity POV

Eporner 4 days ago

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

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

XHamster 6 months ago

Hot Shemale In Chastity Tori Ray Gets Her Yumy Ass Railed Deep

Hot Shemale In Chastity Tori Ray Gets Her Yumy Ass Railed Deep

GetTranny 2 years ago

Forbidden thrills in chastity-fastened solo riding

Forbidden thrills in chastity-fastened solo riding

ShemaleSin 1 week ago

Sissylucylove t-model ball enjoy testicle tonic And Slurp My ball enjoy testicle tonic Innocence S

Sissylucylove t-model ball enjoy testicle tonic And Slurp My ball enjoy testicle tonic Innocence S

TransTube.tv 3 days ago

Rachael Belle Exposed Chastity Sissy Slut Humiliation 5

Rachael Belle Exposed Chastity Sissy Slut Humiliation 5

AShemaleTube 1 year ago

Pluged and Chastity Large Melons TS Outdoor Walk

Pluged and Chastity Large Melons TS Outdoor Walk

SortPorn 2 weeks ago

Cute Emo Femboy Luna Moonbound Chastity for BBC

Cute Emo Femboy Luna Moonbound Chastity for BBC

Eporner 6 months ago

Sissy Sandra-Kim outdoor Heelswalk mit S-cup Titten

Sissy Sandra-Kim outdoor Heelswalk mit S-cup Titten

XHamster 5 days ago

Jenny Wei in Gape Horse

Jenny Wei in Gape Horse

Eporner 5 months ago

Chinese ladyboy cums in front of photographer during photo shoot

Chinese ladyboy cums in front of photographer during photo shoot

Pornzona 2 weeks ago

Mistress and bbc train sissy in chastity

Mistress and bbc train sissy in chastity

AShemaleTube 1 year ago

Chastity Compilation Trans and Sissy Girls Locked and Fucked

Chastity Compilation Trans and Sissy Girls Locked and Fucked

TrannyGem 4 years ago

analvids - emily adaire chastity caged trans girl got her naughty mode on turned porn video

analvids - emily adaire chastity caged trans girl got her naughty mode on turned porn video

TransDoe 1 year ago

NATALIE MARS PONY HAVE FUN

NATALIE MARS PONY HAVE FUN

TrannyGem 7 years ago

Chastity Slut Destroyed By DoggyStyle Pounding

Chastity Slut Destroyed By DoggyStyle Pounding

JuicyTrans 5 days ago

POV Fuck my sissy boy in chastity

POV Fuck my sissy boy in chastity

Pornzona 2 weeks ago

Sissy Sasha cums free hands big dildo

Sissy Sasha cums free hands big dildo

AShemaleTube 1 week ago

First-ever Time Handballing Vid with Cagedjock Part two Conversation and Handballing, Nip Have fun Booty Speculum, Rubdown Machine and Pegging

First-ever Time Handballing Vid with Cagedjock Part two Conversation and Handballing, Nip Have fun Booty Speculum, Rubdown Machine and Pegging

4Gay 3 weeks ago

She's all alone with her dildo

She's all alone with her dildo

AShemaleTube 1 year ago

slutty small tits blonde ts in chastity fucked by bbc

slutty small tits blonde ts in chastity fucked by bbc

PornOne 1 year ago

Hot Rough Shemale Threesome With Bbc Chastity And Alex

Hot Rough Shemale Threesome With Bbc Chastity And Alex

AbTranny 8 months ago

Sissy shemale piss walking while in chastity cage and butt plug

Sissy shemale piss walking while in chastity cage and butt plug

Itsrealamateurs 1 week ago

Caged Sissy Knows Her Place In Front Of BBC

Caged Sissy Knows Her Place In Front Of BBC

AShemaleTube 11 months ago

Girls

Eporner 3 years ago

Anal Sex Toy Chastity Cage Came Off - Natalie Mars

Anal Sex Toy Chastity Cage Came Off - Natalie Mars

BeMyHole 3 weeks ago

BBC Destroys Chastity & Breds Her Hot Russian Ass In Wild BBC Sex

BBC Destroys Chastity & Breds Her Hot Russian Ass In Wild BBC Sex

TrannyMovs 3 months ago

Brazil lost the World Bowl, but the duo didn't lose their lunchbox. I had superb hump with them - Finish on Crimson - Arya Santana

Brazil lost the World Bowl, but the duo didn't lose their lunchbox. I had superb hump with them - Finish on Crimson - Arya Santana

TrannyGem 1 week ago

She Is His Property Now Chastity Slave Trans Takes Bbc

She Is His Property Now Chastity Slave Trans Takes Bbc

AbTranny 3 days ago

Breeding a caged sissy's pussy to celebrate Pride

Breeding a caged sissy's pussy to celebrate Pride

XHamster 1 month ago

my fav

AShemaleTube 1 year ago

Chastity Cage Came Off

Chastity Cage Came Off

Eporner 2 years ago

Crossdresser in Chastity Fucked Raw

Crossdresser in Chastity Fucked Raw

XHamster 1 month ago

Sissy faggot sex machine stuffed with thick creampie

Sissy faggot sex machine stuffed with thick creampie

GayPornWatch 1 week ago

I tied up and creampied a sissy sub

I tied up and creampied a sissy sub

XHamster 1 week ago

Sissy maid Lianna Lawson fucked in chastity

Sissy maid Lianna Lawson fucked in chastity

AShemaleTube 1 year ago

Tgirl in flat cage rides BBC Fuck machine until her brain melts

Tgirl in flat cage rides BBC Fuck machine until her brain melts

Dafreeporn 1 month ago

Guy with a tiny chastity cock! Teased and fucked by cute tranny girl! POV

Guy with a tiny chastity cock! Teased and fucked by cute tranny girl! POV

XHamster 1 week ago

Femboy about to caught while exposure in public men's toilet with metal chastity cage and microskirt on.

Femboy about to caught while exposure in public men's toilet with metal chastity cage and microskirt on.

XHamster 2 weeks ago

Prison Guard

ShemaleSin 1 week ago

SISSY IN HIGH HIGH-HEELED SLIPPERS XXL STRAP ON DILDO IN THE BOOTY Pegging Extraordinary Ass Fucking Opening Up FEMALE DOM RUMP GOING KNUCKLE DEEP

SISSY IN HIGH HIGH-HEELED SLIPPERS XXL STRAP ON DILDO IN THE BOOTY Pegging Extraordinary Ass Fucking Opening Up FEMALE DOM RUMP GOING KNUCKLE DEEP

TrannyGem 4 years ago

Obedient sissy slut in chastity

Obedient sissy slut in chastity

AShemaleTube 1 week ago

TRANSFIXED - Hot Waitress Emma Rose Rekindles With Bestie Leana Lovings During After Hour

TRANSFIXED - Hot Waitress Emma Rose Rekindles With Bestie Leana Lovings During After Hour

Some.Porn 1 year ago

Rough Pegging in Latex

Rough Pegging in Latex

Pornzona 2 weeks ago

Camgirl trapped in cage getting fucked hard with girlcock anal deep moaning

Camgirl trapped in cage getting fucked hard with girlcock anal deep moaning

JuicyTrans 1 week ago

Chastity T-girl, 4on1 With Itzel Saenz

Chastity T-girl, 4on1 With Itzel Saenz

PornUse 3 days ago

onlyfans - fayefayebaby this is what every transgirl needs porn video

onlyfans - fayefayebaby this is what every transgirl needs porn video

TransDoe 1 year ago

sissyjoyce - mistress laura plays with me

sissyjoyce - mistress laura plays with me

TransDoe 2 years ago

Sissy School Education FemDom POV Video

Sissy School Education FemDom POV Video

Pornzona 5 days ago

Sexy Chastity TS Vs BBC

Sexy Chastity TS Vs BBC

BeMyHole 6 months ago

Redhead gets deepthroat sextoy hands free joy

Redhead gets deepthroat sextoy hands free joy

ShemaleSin 1 week ago

Gagged Nylon Doxy Gets Her Face Screwed and Booty Pounded Like a Cheap Cum Dump

Gagged Nylon Doxy Gets Her Face Screwed and Booty Pounded Like a Cheap Cum Dump

ShemaleSin 1 week ago

The Fresh Sissy U

The Fresh Sissy U

ShemaleSin 3 weeks ago

Rough Sex With A Ts Wearing A Chastity Belt In The Bedroom

Rough Sex With A Ts Wearing A Chastity Belt In The Bedroom

Eporner 4 days ago

Innocence real hookup starring woman

Innocence real hookup starring woman

TransTube.tv 6 days ago

Sissy Cock Humiliation: I Reframe My Slave and Mark Them with My Power - Mistress Julia

Sissy Cock Humiliation: I Reframe My Slave and Mark Them with My Power - Mistress Julia

Pornfact 6 days ago

Trans Rachael Belle Experiences a Raunchy Awakening

Trans Rachael Belle Experiences a Raunchy Awakening

ShemaleSin 2 weeks ago

White Stockinged FemDom Sissy Gets Destroyed in Anal Chastity

White Stockinged FemDom Sissy Gets Destroyed in Anal Chastity

JuicyTrans 2 weeks ago

Edging with my machine

Edging with my machine

ShemaleSin 1 week ago

Stepdaddies Little Chastity Slut - Fucking Machine Cumshot

Stepdaddies Little Chastity Slut - Fucking Machine Cumshot

Pornzona 3 weeks ago

sabina steele posh n goth date night creampie transgirl on transgirl

sabina steele posh n goth date night creampie transgirl on transgirl

TransDoe 2 years ago

Russian Trans In Chastity Demolished And Bred By BBC

Russian Trans In Chastity Demolished And Bred By BBC

AShemaleTube 3 months ago

Top 10 Sissy Ideas 2024

Top 10 Sissy Ideas 2024

Pornzona 1 month ago

Pink Sissy

AShemaleTube 3 years ago

1 2 3 4 5

37,183 results found

Related categories

Chastity Cage Dominatrix Mistress Whip Femdom Slave Humiliation Femdom Humiliation Chastity Belt Cage Slave Slave Training Bondage Pegging Spanked BDSM Slave Femdom Handjob Latex Femdom Hogtied Femdom Pegging Maledom

Narrow your search

chastity cage chastity cum sissy chastity chastity fuck flat chastity chastity bbc chastity sissygasm cum in chastity femdom chastity bbc chastity chastity bondage chastity orgasm public chastity femboy chastity 18+ chastity slave chastity fuckdoll chastity femdom permanent chastity chastity public chastity bdsm

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.