Chastity Videos - Trans (48,276)

Blonde Trans Fisting Silicone Pussy

Blonde Trans Fisting Silicone Pussy

xHamster 6 months ago

Hankey's XL Beefcake pounds my brains to mush

Hankey's XL Beefcake pounds my brains to mush

ShemaleSin 2 years ago

Vladasexytrans Training Asshole

Vladasexytrans Training Asshole

xHamster 3 months ago

Reward for the Chastity slave! Humiliating fuck with a rubber doll!

Reward for the Chastity slave! Humiliating fuck with a rubber doll!

xHamster 1 year ago

onlyfans - natalie stone sensual date

onlyfans - natalie stone sensual date

TransDoe 2 years ago

My Ass is My Pussy

My Ass is My Pussy

xHamster 7 months ago

Rainbow Nyxi Leon Strips to Entice Stud Stepdaddy

44% HD 1:01 / 5:54

Rainbow Nyxi Leon Strips to Entice Stud Stepdaddy

FapHouse 1 year ago

Sissy Maid V-card Ejaculation

Sissy Maid V-card Ejaculation

4Gay 5 months ago

Sissy Foot Fetish Job Interview Video - Footjob And Blowjob Training Chastity Slut Jessica Bloom

Premium HD 20:22

Sissy Foot Fetish Job Interview Video - Footjob And Blowjob Training Chastity Slut Jessica Bloom

xnxxGold 1 year ago

Ta nouvelle sexualité comme Sissy : EP5 Transformer un Branleur en Esclave - Maitresse Julia Female Dominance

Ta nouvelle sexualité comme Sissy : EP5 Transformer un Branleur en Esclave - Maitresse Julia Female Dominance

TrannyGem 1 year ago

Oriental Sissy Nun Jenny Wei Gets Large White Schlong Anal Training

Oriental Sissy Nun Jenny Wei Gets Large White Schlong Anal Training

ShemaleSin 3 years ago

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

56% HD 0:10 / 14:01

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

LoyalFans 4 months ago

Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf

67% HD 0:39 / 27:42

Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf

FapHouse 4 months ago

Nicco & Patric & Santiago Private Show

Nicco & Patric & Santiago Private Show

Flirt4Free 2 years ago

Leggy tranny with caged cock rides big dildo - Amateur Solo

Leggy tranny with caged cock rides big dildo - Amateur Solo

AnySex 1 year ago

-LOCKTOBER URETHRAL PLAY-

-LOCKTOBER URETHRAL PLAY-

xHamster 2 years ago

Locked Sissy Bound up and Taunted by Electro-Hitachi

Locked Sissy Bound up and Taunted by Electro-Hitachi

GayCK 4 years ago

Jessica Bloom's Large Knob Throbs From Anal - Caged and Released Hands-Free Squirting Orgasms

Jessica Bloom's Large Knob Throbs From Anal - Caged and Released Hands-Free Squirting Orgasms

Lesbian8 1 month ago

An Unexpected Christmas Gift: Sissy's Penetration - Mistress Julia

HD 1:01 / 16:56

An Unexpected Christmas Gift: Sissy's Penetration - Mistress Julia

FapHouse 1 year ago

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

xHamster 2 years ago

Fat NB unlocks inverted chastity cage for cleaning and plays with dick and foreskin

Fat NB unlocks inverted chastity cage for cleaning and plays with dick and foreskin

xHamster 6 months ago

Fucking my CAGED little tranny toy and CUMMING on her ass

Fucking my CAGED little tranny toy and CUMMING on her ass

aShemaleTube 10 months ago

The Night Before Freshmas 7 - The North Hole

Premium HD 30:00

The Night Before Freshmas 7 - The North Hole

xnxxGold 3 months ago

Man-Sized fuck machine dildo knocking off locked in chastity

Man-Sized fuck machine dildo knocking off locked in chastity

SexTubeSpot 4 years ago

Sissy at Gloryhole Gets Rimmed by Stranger

Sissy at Gloryhole Gets Rimmed by Stranger

ShemaleSin 3 years ago

Sophia Loreen Party on Apr 18, 2026 - Part 3

HD 2:00 / 33:08

Sophia Loreen Party on Apr 18, 2026 - Part 3

Flirt4Free 4 days ago

Sissy Maid Armbinder Self Bondage in new Maid Dress and Ballet Boots

Sissy Maid Armbinder Self Bondage in new Maid Dress and Ballet Boots

xHamster 3 years ago

Sissy Bride in Chastity

61% 0:39 / 14:03

Sissy Bride in Chastity

FapHouse 4 months ago

Shemale sissy slave ball busting

Shemale sissy slave ball busting

xHamster 3 months ago

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

62% HD 0:35 / 20:42

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

PissVids 1 year ago

Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy

HD 1:01 / 12:30

Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy

FapHouse 9 months ago

Patric & Oliver Private Show

61% HD 2:00 / 4:09

Patric & Oliver Private Show

Flirt4Free 3 years ago

How to Destroy Your Man’s Masculinity

How to Destroy Your Man’s Masculinity

Amateur8 5 years ago

Medfet shaving genitals after locktober

59% HD 0:10 / 19:04

Medfet shaving genitals after locktober

LoyalFans 2 years ago

Vladasexytrans Extreme Play Ptolapse Fisting and Gape

Vladasexytrans Extreme Play Ptolapse Fisting and Gape

FapHouse 11 months ago

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

PissVids 1 year ago

GRAVEI MINHA PRIMEIRA VEZ COM UMA TRANS, FIZEMOS UM TROCA TROCA E DEPOIS ELA COMEU MEU CU - EVEZZINI

Premium HD 46:49

GRAVEI MINHA PRIMEIRA VEZ COM UMA TRANS, FIZEMOS UM TROCA TROCA E DEPOIS ELA COMEU MEU CU - EVEZZINI

XVideosRed 1 month ago

Chastity Sissy Slut Sissygasms Gushing in Satin Lingerie Dildo Ride

Chastity Sissy Slut Sissygasms Gushing in Satin Lingerie Dildo Ride

JuicyTrans 2 weeks ago

Sara & Elver Private Show

63% HD 2:00 / 5:36

Sara & Elver Private Show

Flirt4Free 2 months ago

Trans Female Takes BIG BLACK COCK From Boink Machine ROCK HARD!!!! Encaged Boner Jism!!!!

Trans Female Takes BIG BLACK COCK From Boink Machine ROCK HARD!!!! Encaged Boner Jism!!!!

TrannyGem 8 months ago

Bodystocking, box, ass-plug and peeing

Bodystocking, box, ass-plug and peeing

GayCK 3 years ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 4 days ago

Ele colocou uma gaiola de castidade em mim, algemas e gag ball. Transamos muito e ainda levei porra na cara

Premium HD 24:45

Ele colocou uma gaiola de castidade em mim, algemas e gag ball. Transamos muito e ainda levei porra na cara

xnxxGold 2 years ago

The Chastity Rabbit Hole

72% HD 1:01 / 9:03

The Chastity Rabbit Hole

FapHouse 1 year ago

Sissy Chastity Training Cock Worship

HD 0:10 / 10:15

Sissy Chastity Training Cock Worship

LoyalFans 2 years ago

Encontrei com o f&atilde_ em Copacabana n&atilde_o resistiu o pau dele super duro sentei gostosa

Premium HD 6:08

Encontrei com o f&atilde_ em Copacabana n&atilde_o resistiu o pau dele super duro sentei gostosa

XVideosRed 2 months ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Flirt4Free 1 week ago

Sophia Loreen Party on Sep 10, 2025 - Part 2

54% 4K 2:00 / 7:22

Sophia Loreen Party on Sep 10, 2025 - Part 2

Flirt4Free 7 months ago

Ruined Orgasm in Chastity and CBT for Lana Trap

Ruined Orgasm in Chastity and CBT for Lana Trap

Tranny.one 4 years ago

Sissy coming home from work

Sissy coming home from work

2BGay 8 months ago

BTG goes Wet, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Pee Drink, Creampie, Cum in Mouth BTG117

Premium 1:02:43

BTG goes Wet, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Pee Drink, Creampie, Cum in Mouth BTG117

xnxxGold 2 years ago

Oiled Sissy in Flat Chastity Riding Massive Dildos

72% HD 0:39 / 4:11

Oiled Sissy in Flat Chastity Riding Massive Dildos

FapHouse 1 year ago

Trans Cutie groans as her nuts get boiled~

Trans Cutie groans as her nuts get boiled~

Amateur8 4 months ago

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

xHamster 1 year ago

Sissy Games: When My Cuckold Husband Meets My Lover - Part 1 - Maitresse Julia

57% 0:39 / 10:51

Sissy Games: When My Cuckold Husband Meets My Lover - Part 1 - Maitresse Julia

FapHouse 2 years ago

F-Machine Fucked While Sucking Dick Jessica Bloom Gets Spitroasted With Julia Edge

F-Machine Fucked While Sucking Dick Jessica Bloom Gets Spitroasted With Julia Edge

xHamster 1 year ago

IT IS MORE DELICIOUS AS A FAMILY LLE019

Premium HD 29:51

IT IS MORE DELICIOUS AS A FAMILY LLE019

Sheer 5 years ago

Kitty vs Bunny

Premium HD 45:10

XVideosRed 1 year ago

Twinkerbell Pegging the Lost Femboi in Chastity

Twinkerbell Pegging the Lost Femboi in Chastity

xHamster 1 year ago

Cute Caged Sissy Cums Like A Girl

Cute Caged Sissy Cums Like A Girl

xHamster 2 years ago

SISSY Buttfuck Instructing by SPANDEX Domme

SISSY Buttfuck Instructing by SPANDEX Domme

TrannyGem 4 months ago

Colombian Boys Private Show

65% HD 2:00 / 33:09

Colombian Boys Private Show

Flirt4Free 7 months ago

Fist My Slutty Sissy Hole and Prolapse My Juicy Red Anal Rosebud Clip 1

Fist My Slutty Sissy Hole and Prolapse My Juicy Red Anal Rosebud Clip 1

xHamster 4 months ago

Talking a little about sex and hookups with men - pegging

Talking a little about sex and hookups with men - pegging

xHamster 2 months ago

New Steel Urethra Chastity Cage

New Steel Urethra Chastity Cage

FapHouse 1 year ago

Massive Cumshot Chastity Cage and Tights

Massive Cumshot Chastity Cage and Tights

FapHouse 3 days ago

Seduced By Silk - Star Nine

58% HD 0:10 / 13:41

Seduced By Silk - Star Nine

LoyalFans 2 years ago

Orianna Dunn Private Show

44% HD 2:00 / 6:57

Orianna Dunn Private Show

Flirt4Free 2 years ago

Dump sissy bimbo bitch squirts hands free in chastity and eats cum

Dump sissy bimbo bitch squirts hands free in chastity and eats cum

xHamster 1 year ago

beta fucktoy part 2: free use office bitch in panties and chastity for futa boss

beta fucktoy part 2: free use office bitch in panties and chastity for futa boss

LoyalFans 2 years ago

Sissy BatGirl with Hit Girl and Batman Cosplay Parody

Sissy BatGirl with Hit Girl and Batman Cosplay Parody

xHamster 5 years ago

Even More Chilling Out with Some Porn..

Even More Chilling Out with Some Porn..

xHamster 11 months ago

3 Trans Honeys Have A Kinky Bang-out

3 Trans Honeys Have A Kinky Bang-out

Transvids.tv 9 months ago

Spectacular TRANSSEXUAL Kitty Lucia Maya Leaks Spunk in Purity While Banging Her Backside Then Unlocks Box & Jizzes Firm

Spectacular TRANSSEXUAL Kitty Lucia Maya Leaks Spunk in Purity While Banging Her Backside Then Unlocks Box & Jizzes Firm

TrannyGem 1 year ago

I turn my husband into a sissy in a chastity cage

I turn my husband into a sissy in a chastity cage

xHamster 2 years ago

Black TGirls Hardcore - Chastity Kane

Black TGirls Hardcore - Chastity Kane

Tranny.one 3 years ago

AB081 Gentle Unstoppable dumping - Big fake penis (Japanese and English subtitles)

AB081 Gentle Unstoppable dumping - Big fake penis (Japanese and English subtitles)

TrannyGem 3 years ago

Tgirl Diversity Itsol faps dressed in fufu pin

Tgirl Diversity Itsol faps dressed in fufu pin

TrannyGem 1 year ago

NOVINHA BRANQUINHA TRANSANDO COM NEG&Atilde_O NA HIDROMASSAGEM - LUANA PRADO

NOVINHA BRANQUINHA TRANSANDO COM NEG&Atilde_O NA HIDROMASSAGEM - LUANA PRADO

XVideosRed 4 months ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 10 months ago

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

TrannyGem 11 months ago

2032 - the Bwno Future

55% 0:39 / 15:06

2032 - the Bwno Future

FapHouse 7 months ago

Estim and CBT Compilation 3 - from estim to beating off to crossdresser... Mostly HFO

Estim and CBT Compilation 3 - from estim to beating off to crossdresser... Mostly HFO

xHamster 2 years ago

Sissy Fisting Ass Hard in Chastity

Sissy Fisting Ass Hard in Chastity

xHamster 3 years ago

Routine Inspection Pt 1

67% HD 0:10 / 11:43

Routine Inspection Pt 1

LoyalFans 1 year ago

Castity Sissy gets intens fuck by machine

Castity Sissy gets intens fuck by machine

xHamster 1 year ago

Hooters Sissy in Chastity

Hooters Sissy in Chastity

xHamster 2 weeks ago

wrecked sissy's ejaculation after pussyjob

wrecked sissy's ejaculation after pussyjob

TrannyGem 1 year ago

Work that ass

aShemaleTube 2 months ago

Numerous Guts Climaxes in Innocence Jessica Bloom the Spunk Cow

Numerous Guts Climaxes in Innocence Jessica Bloom the Spunk Cow

TrannyGem 1 year ago

Sissy in a innocence cell drills herself with a plow machine after the beach

Sissy in a innocence cell drills herself with a plow machine after the beach

TrannyGem 4 months ago

Becoming a Woman - Sissyfication - Ultimate Sissy Transformation

Becoming a Woman - Sissyfication - Ultimate Sissy Transformation

xHamster 2 months ago

极品TSCD女装大佬贱奴被3人调教 sex chinese shemale sex with 3guys

极品TSCD女装大佬贱奴被3人调教 sex chinese shemale sex with 3guys

aShemaleTube 6 years ago

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

xHamster 1 year ago

Rough Pegging in Latex

Rough Pegging in Latex

Pornzona 1 month ago

Granny tranny Holly riding a BBC dildo and cums in her chastity cage

Granny tranny Holly riding a BBC dildo and cums in her chastity cage

xHamster 8 months ago

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

Premium HD 17:38

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

xnxxGold 4 months ago

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

xHamster 1 year ago

To take my chastity in an deserted health center, we were caught

To take my chastity in an deserted health center, we were caught

4Gay 5 months ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 3 years ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 2 months ago

The final transformation - Mistress Tatjana

The final transformation - Mistress Tatjana

xHamster 2 years ago

Pizza Delivery Guy Fucks Hot Trans Woman in Chastity

Pizza Delivery Guy Fucks Hot Trans Woman in Chastity

xHamster 2 years ago

Just Outta Curiosity

65% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 2 years ago

eu nao acredito que deixei meu namorado gozar na minha boca - pela primeira vez deixei alguem gozar na minha cara e registrei tudo - completo no red

eu nao acredito que deixei meu namorado gozar na minha boca - pela primeira vez deixei alguem gozar na minha cara e registrei tudo - completo no red

PissVids 8 months ago

TS Natalie Mars fisted and stretched by MILF Penny Barber

TS Natalie Mars fisted and stretched by MILF Penny Barber

UrGayPorn 9 months ago

dei meu cuzinho pela primeira vez para duas novinhas trans dotadas elas fizeram ate dp - evezzini

58% 0:30 / 17:21

dei meu cuzinho pela primeira vez para duas novinhas trans dotadas elas fizeram ate dp - evezzini

PornBox 1 month ago

Watch Wollip's tight ass take a massive load after being uncensored & wearing chastity cage

Watch Wollip's tight ass take a massive load after being uncensored & wearing chastity cage

TrannyMovs 7 months ago

Simon & Juseph & Alejandro Private Show

57% HD 2:00 / 1:02:40

Simon & Juseph & Alejandro Private Show

Flirt4Free 2 years ago

Maskedloki9's gothic crossdresser gets bred by BBC in fishnet stockings

Maskedloki9's gothic crossdresser gets bred by BBC in fishnet stockings

TrannyMovs 6 months ago

Cumming in Chastity-Self Slavery Gasmask Suspension Harness

Cumming in Chastity-Self Slavery Gasmask Suspension Harness

ShemaleSin 3 years ago

Blond foolish mounds sissy tramp unsheathed as public parking plenty of tramp demonstrates everything part trio

Blond foolish mounds sissy tramp unsheathed as public parking plenty of tramp demonstrates everything part trio

TrannyGem 2 years ago

[SISSY] I got bare in the park in the daytime

[SISSY] I got bare in the park in the daytime

TrannyGem 8 months ago

blonde sissy fucks herself with a dildo in a chastity belt

blonde sissy fucks herself with a dildo in a chastity belt

xHamster 1 year ago

Isabelly Ferreira &egrave_ a Festa de Putaria com muita Safadeza

Premium HD 25:08

Isabelly Ferreira &egrave_ a Festa de Putaria com muita Safadeza

XVideosRed 5 months ago

Jacob Malik Private Show

58% HD 2:00 / 11:23

Jacob Malik Private Show

Flirt4Free 2 months ago

Plugged, Padded, Locked, and Stoned!

Plugged, Padded, Locked, and Stoned!

SortPorn 2 months ago

AB104 Sex toy tester surrender (English subtitles)

AB104 Sex toy tester surrender (English subtitles)

xHamster 2 years ago

Sissy Grandma holly cums in her cage while riding a BBC dildo

Sissy Grandma holly cums in her cage while riding a BBC dildo

aShemaleTube 8 months ago

MINHA AMIGA ME GRAVOU ENQUANTO EU TRANSAVA COM MARIDO DELA - LUANA PRADO

MINHA AMIGA ME GRAVOU ENQUANTO EU TRANSAVA COM MARIDO DELA - LUANA PRADO

xnxxGold 7 months ago

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