Chastity Videos - Trans (48,648)

Hawt Punk Playgirl Gets Banged on Pool Table

Hawt Punk Playgirl Gets Banged on Pool Table

ShemaleSin 4 weeks ago

Greek Sissy Wants to Cum in Chastity

Greek Sissy Wants to Cum in Chastity

xHamster 2 weeks ago

Flat Chastity Belt and Huge Anal Dildo

Flat Chastity Belt and Huge Anal Dildo

FapHouse 4 months ago

Rainbow Kitty Scarlet Sky Drizzles Female Cum!

Rainbow Kitty Scarlet Sky Drizzles Female Cum!

TransTube.tv 1 year ago

Sarait Gil Private Show

Sarait Gil Private Show

Flirt4Free 6 months ago

Delicious Cheeks Plays Deltarune (part two) [with Mutt Faux-Cock!]

Delicious Cheeks Plays Deltarune (part two) [with Mutt Faux-Cock!]

TrannyGem 5 years ago

Podcast Ep13: Sissy, Chastity and Lust

Podcast Ep13: Sissy, Chastity and Lust

xHamster 5 years ago

Fucking machine makes the locked clit of this sissy leak in no time!

Fucking machine makes the locked clit of this sissy leak in no time!

XGroovy 1 year ago

Go Gay For My Girl-Cock (SD MP4)

62% 4K 0:32 / 15:55

Go Gay For My Girl-Cock (SD MP4)

Clips4sale 1 year ago

Femboy Cleans Your Apartment and Then Sprays His Stockings with Cum

59% HD 1:01 / 8:33

Femboy Cleans Your Apartment and Then Sprays His Stockings with Cum

FapHouse 7 months ago

Jackie Israeli Sissy Learns (slowly) How To Cum With Her Chastity On

Jackie Israeli Sissy Learns (slowly) How To Cum With Her Chastity On

AbTranny 3 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 month ago

dei gostoso pro meu patrao na banheira - luana prado

63% 0:30 / 12:47

dei gostoso pro meu patrao na banheira - luana prado

PornBox 1 month ago

Purity Box Challange - Day two/ten

Purity Box Challange - Day two/ten

Gayhub 8 months ago

Locked Pink Latex Bimbo Slut Shaking Sissygasm on Huge Dildo - full video on LayneLovee Manyvids

Locked Pink Latex Bimbo Slut Shaking Sissygasm on Huge Dildo - full video on LayneLovee Manyvids

xHamster 2 years ago

Chastity and Anal Training

72% 0:30 / 20:51

Chastity and Anal Training

Clips4sale 1 year ago

Ball busting with bbc

Ball busting with bbc

xHamster 1 year ago

The Reward for the Locked-up Sissy

45% HD 1:01 / 12:56

The Reward for the Locked-up Sissy

FapHouse 5 months ago

Fucking blonde sissy slut in chastity

Fucking blonde sissy slut in chastity

xHamster 10 months ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 3 years ago

Sandy Nell Private Show

HD 2:00 / 39:18

Sandy Nell Private Show

Flirt4Free 2 years ago

”Locktober Chastity Suck Whore for Dommes Bambi Bliss & Brittany Andrews”

”Locktober Chastity Suck Whore for Dommes Bambi Bliss & Brittany Andrews”

Faptor 2 years ago

Sophia Loreen Private Show

HD 2:00 / 22:20

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Feet and ass for a slutty sissy fagot wifey

Feet and ass for a slutty sissy fagot wifey

xHamster 2 years ago

Mistress Cums in Chastity Caged Hubby's Lips

Mistress Cums in Chastity Caged Hubby's Lips

MomXL 1 year ago

”black dick transgender anal fucks white date”

”black dick transgender anal fucks white date”

Trashreality 1 year ago

Desire Sweet Private Show

HD 2:00 / 24:59

Desire Sweet Private Show

Flirt4Free 7 months ago

Premature Handsfree Sissygasm - Cum shot in 30 Seconds!

Premature Handsfree Sissygasm - Cum shot in 30 Seconds!

WebcamBros 1 month ago

Thick chubby Femboy needs a BBC

Thick chubby Femboy needs a BBC

xHamster 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

OverWatch HENTAI DOUBLE ANAL. SISSY CUMMS IN THE CHASTITY CAGE ON HER STOCKINGS

Premium HD 9:13

OverWatch HENTAI DOUBLE ANAL. SISSY CUMMS IN THE CHASTITY CAGE ON HER STOCKINGS

Sheer 2 years ago

Femboy in virginity cage gets knotted by Fat Bad Dragon Bishop on his pummel machine.

Femboy in virginity cage gets knotted by Fat Bad Dragon Bishop on his pummel machine.

4Gay 6 months ago

Troy & Kiros Private Show

Troy & Kiros Private Show

Flirt4Free 2 years ago

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

xHamster 2 months ago

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

Flirt4Free 3 years ago

Sissy purity (part 1)

Sissy purity (part 1)

TrannyGem 3 years ago

NOVINHA TRANS CASADA ME CHAMOU PRO MOTEL ESCONDIDO E ELA ME COMEU E EU COMI ELA - EVEZZINI

Premium HD 14:42

NOVINHA TRANS CASADA ME CHAMOU PRO MOTEL ESCONDIDO E ELA ME COMEU E EU COMI ELA - EVEZZINI

xnxxGold 2 months ago

fuck sex chinese trans bitch erxiaojie

fuck sex chinese trans bitch erxiaojie

aShemaleTube 7 years ago

walking down a country road in high heels

walking down a country road in high heels

xHamster 2 years ago

trans in chastity extreme gape with inflateable butt plug

74% 0:13 / 7:16

trans in chastity extreme gape with inflateable butt plug

Clips4sale 1 year ago

Tranny girly locked by daddy! Bad girl cheats until cumshot!

Tranny girly locked by daddy! Bad girl cheats until cumshot!

Clips4sale 11 months ago

Kitty vs Bunny

Premium HD 45:10

Sheer 1 year ago

Troy Khalil Private Show

74% HD 2:00 / 18:38

Troy Khalil Private Show

Flirt4Free 2 years ago

sissy sonya on gynochair nailed by screwing machine

sissy sonya on gynochair nailed by screwing machine

TrannyGem 2 years ago

Big-Tits ebony heshe fucking man

Big-Tits ebony heshe fucking man

Sheshaft 4 years ago

Sissy Lucy Anal Training in Chastity with Massive Dildos and Getting Pegged by Lisa

Sissy Lucy Anal Training in Chastity with Massive Dildos and Getting Pegged by Lisa

MatureTubeHere 4 years ago

Bambi Christa Reverse Striptease

Bambi Christa Reverse Striptease

aShemaleTube 4 years ago

Skyler Banx Can't Resist Trans Rachael Belle

Premium HD 28:23

Skyler Banx Can't Resist Trans Rachael Belle

Sheer 1 year ago

2 futas discover u alone in the park

2 futas discover u alone in the park

ShemaleSin 7 months ago

24/7 Sissy Slavery

24/7 Sissy Slavery

LoyalFans 1 year ago

Glazing Donuts

66% HD 0:29 / 32:49

Clips4sale 1 year ago

Astrid Apathy Public Exhibition in Chastity 1

Astrid Apathy Public Exhibition in Chastity 1

ShemaleSin 3 years ago

SHOW TIME! Sexy body tour and the best ASS bouncing and riding till explode! Wanna be part of this orgasm? JOIN JOIN JOIN ! - Part 4

SHOW TIME! Sexy body tour and the best ASS bouncing and riding till explode! Wanna be part of this orgasm? JOIN JOIN JOIN ! - Part 4

Flirt4Free 1 week ago

You&rsquo_ve gone too far, beta...There&rsquo_s no turning back, your manhood is gone, and you&rsquo_re nothing but a pretty little sissy now. Might as well embrace it and seal your fate !

Premium HD 34:28

You&rsquo_ve gone too far, beta...There&rsquo_s no turning back, your manhood is gone, and you&rsquo_re nothing but a pretty little sissy now. Might as well embrace it and seal your fate !

XVideosRed 1 year ago

Sissy selfbondage extrem breath control

Sissy selfbondage extrem breath control

xHamster 1 year ago

Ride Dildo Challenges 2

Ride Dildo Challenges 2

xHamster 8 months ago

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

Premium HD 12:58

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

xnxxGold 2 weeks ago

Neon Rave Harlots

Neon Rave Harlots

ShemaleSin 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 year ago

TS Female domination Fake-sausage Encouragement Deep-throat my Penis Sissy POINT OF VIEW Rollplay

TS Female domination Fake-sausage Encouragement Deep-throat my Penis Sissy POINT OF VIEW Rollplay

TransTube.tv 1 year ago

Hawt Golden-haired Sissy Bailey Wilde in Chastity Drilled

Hawt Golden-haired Sissy Bailey Wilde in Chastity Drilled

ShemaleSin 1 month ago

Femboy in a chastity cage gets creampied and gaped by fuck machine

Femboy in a chastity cage gets creampied and gaped by fuck machine

GayJaVu 7 months ago

trans in chastity gets ass destroyed by BBC fuck machine

Premium 4K 9:14

trans in chastity gets ass destroyed by BBC fuck machine

Clips4sale 7 months ago

Caged Sissy Fucks Her Gaping Pulsing Asspussy With A Big Dildo

Caged Sissy Fucks Her Gaping Pulsing Asspussy With A Big Dildo

xHamster 3 years 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

Big boobs black TS anal fucks man

Big boobs black TS anal fucks man

Eporner 5 years ago

New Electro Slut Called by Field Telephone Pain

60% HD 0:30 / 10:52

New Electro Slut Called by Field Telephone Pain

Clips4sale 1 year ago

Innocence Cell Challange - Day 1/ten

Innocence Cell Challange - Day 1/ten

Gayhub 8 months ago

hot trans QoS gets hole destroyed by BBC and spills her cum

64% 0:14 / 17:17

hot trans QoS gets hole destroyed by BBC and spills her cum

Clips4sale 2 years ago

Jessica Chen in Her School Uniform Gets Help with Self Bondage

Jessica Chen in Her School Uniform Gets Help with Self Bondage

Clips4sale 1 month ago

advance sissy fucking machine bbc sex rob piper

advance sissy fucking machine bbc sex rob piper

aShemaleTube 3 years ago

Rubbing Lips Shaped Chastity till Cum

HD 0:10 / 28:03

Rubbing Lips Shaped Chastity till Cum

LoyalFans 1 month ago

Douche With Femboy Tgirl T-Model Chrissy the Encaged Sissy Crossdresser Trans

Douche With Femboy Tgirl T-Model Chrissy the Encaged Sissy Crossdresser Trans

TrannyGem 3 years ago

”Tranny is pissing over her prolapped booty”

”Tranny is pissing over her prolapped booty”

Rainblow 2 months ago

Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum

Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum

Dafreeporn 9 months ago

Fucking My Fat Delicious Ass

4K 2:00 / 17:50

Fucking My Fat Delicious Ass

Flirt4Free 1 month ago

Sophia Loreen Party on Feb 7, 2026 - Part 2

4K 2:00 / 26:13

Sophia Loreen Party on Feb 7, 2026 - Part 2

Flirt4Free 2 months ago

Do You Know How My Soles and Toes Feel?

66% HD 2:00 / 17:49

Do You Know How My Soles and Toes Feel?

Flirt4Free 3 years ago

Sissy Motel bedroom 1

Sissy Motel bedroom 1

TrannyGem 1 year ago

Surprise blindfold fuck with two tranny hotties

Surprise blindfold fuck with two tranny hotties

xHamster 3 years ago

Femboy Enjoy II

Femboy Enjoy II

TrannyGem 6 years ago

GF Catches You Wearing Her Panties - Sissy Humiliation Cuckold

GF Catches You Wearing Her Panties - Sissy Humiliation Cuckold

Juicexxx 1 month ago

Headmaster straps and torments shemale student

Headmaster straps and torments shemale student

Xozilla 7 months ago

Punch Me - PMV by HoloPMV

Punch Me - PMV by HoloPMV

aShemaleTube 1 year ago

Trans Beauty August Harper plays with her girlcock

Trans Beauty August Harper plays with her girlcock

ShemaleSin 8 months ago

Hot Niqabi Crossdresser: Unleashing Desire and Bold Fashion"

Hot Niqabi Crossdresser: Unleashing Desire and Bold Fashion"

xHamster 1 year ago

Bodystocking, box, ass-plug and peeing

Bodystocking, box, ass-plug and peeing

GayCK 3 years ago

chastity fuckdoll 7 - lilly

44% HD 0:30 / 19:29

chastity fuckdoll 7 - lilly

PornBox 1 month ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Testing a new THE THUG DILDO from Greedycluster

Testing a new THE THUG DILDO from Greedycluster

xHamster 2 years ago

Transgirl with a biggest ramrod trying to put on a chastity cage

Transgirl with a biggest ramrod trying to put on a chastity cage

Amateur8 3 years ago

Step-Sister in law Saskia Pounded my Sissy Coochie @Saskia_and_Sasha

Step-Sister in law Saskia Pounded my Sissy Coochie @Saskia_and_Sasha

Transvids.tv 10 months ago

sissy sonya on gyno chair in chastity banged by screwing machine dragon vibrator

sissy sonya on gyno chair in chastity banged by screwing machine dragon vibrator

ShemaleSin 2 years ago

Footjob with Short White Ankle Socks

61% HD 2:00 / 7:51

Footjob with Short White Ankle Socks

Flirt4Free 4 years ago

Practice Makes Perfect (sissy Slut Fills Her Holes)

Practice Makes Perfect (sissy Slut Fills Her Holes)

xHamster 4 months ago

Julieta Shayk Private Show

Julieta Shayk Private Show

Flirt4Free 3 years ago

Ab068 Horny Sissy Bitch Cum In Chastity With Pantyhose And Heels - 淫欲人妖女m丝袜高跟贞操锁强制榨精 With Abby Kitty

Ab068 Horny Sissy Bitch Cum In Chastity With Pantyhose And Heels - 淫欲人妖女m丝袜高跟贞操锁强制榨精 With Abby Kitty

AbTranny 3 years ago

Nasty Trans Buttfuck romp and atm cum-shot coats

Nasty Trans Buttfuck romp and atm cum-shot coats

TrannyGem 3 weeks ago

Sissy Jessica Bloom Spitroast Training With Banging Machine And Dildos - Anal Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Training With Banging Machine And Dildos - Anal Sissygasms and Cumswallow

ShemaleSin 3 weeks ago

Diabla Rivers Private Show

Diabla Rivers Private Show

Flirt4Free 1 year ago

sissy in heels rides BBC ass to mouth and drinks her cum

75% 4K 0:19 / 10:51

sissy in heels rides BBC ass to mouth and drinks her cum

Clips4sale 1 year ago

Cute Asian ladyboy Lexi Faith footfetish cumshot

Premium HD 9:42

Cute Asian ladyboy Lexi Faith footfetish cumshot

XVideosRed 11 months ago

Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Poked Back in & Locked up Afresh!

Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Poked Back in & Locked up Afresh!

BigTitsLust 9 months ago

Vibing Out With A Flat Cage

Vibing Out With A Flat Cage

ShemaleSin 1 year ago

Nara have fun with Ts Roberta Cortes and Ts Janny Costa in front of her cuck husband (EN-sub)

65% HD 0:10 / 21:39

Nara have fun with Ts Roberta Cortes and Ts Janny Costa in front of her cuck husband (EN-sub)

LoyalFans 10 months ago

Milking the Sissy Maid

56% HD 1:01 / 22:25

Milking the Sissy Maid

FapHouse 4 months ago

Latex Transgirl in Chastity Spanked, Teased, and Drilled by Femdom - OnlyFans @Ms_Nacke

Latex Transgirl in Chastity Spanked, Teased, and Drilled by Femdom - OnlyFans @Ms_Nacke

Amateur8 2 years ago

chastity device and ball ring

chastity device and ball ring

xHamster 1 year ago

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

ShemaleSin 2 years ago

Trans in chastity dominated, degraded and bred by BBC

Trans in chastity dominated, degraded and bred by BBC

BigTitsLust 3 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

Tiny Caged Trans Slut Swallows BBC, Gets Her Tight Pink Asshole Stuffed, Then Her Caged Clit Cum All Over!

Premium HD 45:33

Tiny Caged Trans Slut Swallows BBC, Gets Her Tight Pink Asshole Stuffed, Then Her Caged Clit Cum All Over!

Sheer 10 months ago

Lana Page gape training - amateur crossdresser debut (part4)

Lana Page gape training - amateur crossdresser debut (part4)

xHamster 4 years ago

Lola Meow teasing in chastity

Lola Meow teasing in chastity

ShemaleSin 2 years ago

Caged Sissy Trans Gushes Sissycum in Lingerie Toy Wreck Morning

Caged Sissy Trans Gushes Sissycum in Lingerie Toy Wreck Morning

JuicyTrans 3 weeks ago

Wendy Going Down The Rabbit Hole

Wendy Going Down The Rabbit Hole

aShemaleTube 1 year ago

Sissy Hailey Doll gets her holes ruined by BBC😈

Sissy Hailey Doll gets her holes ruined by BBC😈

xHamster 2 years ago

Premature Climax Instructing

Premature Climax Instructing

Tranny.one 1 month ago

Sissygasm & Leaking BIG BLACK COCK

Sissygasm & Leaking BIG BLACK COCK

TrannyGem 1 year ago

Corno cdzinha

Premium HD 2:12

XVideosRed 1 year ago

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