Chastity Videos - Trans (43,326)

Working from home as a Chastity Sissy Secretary is so much joy

Working from home as a Chastity Sissy Secretary is so much joy

ShemaleSin 3 years ago

BBC Sissygasm

xHamster 1 month ago

Sissy Chastity Trainer

Sissy Chastity Trainer

aShemaleTube 1 year ago

Jhon & Derek & Chris Private Show

44% HD 2:00 / 31:06

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Sissy left alone

Sissy left alone

SexTubeSpot 8 years ago

Master & Ithan & Aleex Private Show

40% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 1 month ago

Sissy slut fucked in chastity cage cums hands free 234

Sissy slut fucked in chastity cage cums hands free 234

MenGem 3 years ago

DESTROYING BAMBI HART

59% HD 0:10 / 22:32

DESTROYING BAMBI HART

LoyalFans 11 months ago

Nettles chastity torture

Nettles chastity torture

xHamster 2 years ago

Patric & Marc & Thiago Private Show

50% HD 2:00 / 15:34

Patric & Marc & Thiago Private Show

Flirt4Free 2 years ago

Sissy String-on Spitroast in Chastity Pegged by Splendid doll dom Duo by Mistress Mercer

Sissy String-on Spitroast in Chastity Pegged by Splendid doll dom Duo by Mistress Mercer

TransTube.tv 9 months ago

travesti do pauzao arrombando cu da travesti magrinha

53% HD 0:30 / 15:16

travesti do pauzao arrombando cu da travesti magrinha

PornBox 1 year ago

Jhon & Derek & Chris Private Show

43% HD 2:00 / 32:48

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

chastity t-girl, natalie mars, dap, double anal fisting, wrecked ass, almost rose, creampie, swallow btg051

chastity t-girl, natalie mars, dap, double anal fisting, wrecked ass, almost rose, creampie, swallow btg051

SukaPorn 1 year ago

Fuck Me Sideways, I Flooded Aline Tavares' Ass Like a Fucking Geyser

Fuck Me Sideways, I Flooded Aline Tavares' Ass Like a Fucking Geyser

XXXShake 4 months ago

Castity Sissy gets intens fuck by machine

Castity Sissy gets intens fuck by machine

xHamster 6 months ago

POV micro chastity cage release cum shot

POV micro chastity cage release cum shot

xHamster 2 years ago

Sissbeq Is Preparing Her Gaping Boypussy In Adult Theater

Sissbeq Is Preparing Her Gaping Boypussy In Adult Theater

xHamster 3 years ago

sissy in chastity with CBT

sissy in chastity with CBT

xHamster 2 years ago

Crossdresser gets machine fucked with XXL Monster Dildos #2

Crossdresser gets machine fucked with XXL Monster Dildos #2

xHamster 1 year ago

duas travesti do pau grande fizeram uma suruba com as suas amigas enquanto o macho delas nao dava conta

duas travesti do pau grande fizeram uma suruba com as suas amigas enquanto o macho delas nao dava conta

PissVids 1 year ago

Ashtray Pig - Rough Pegging for Miss Piggy

Ashtray Pig - Rough Pegging for Miss Piggy

aShemaleTube 2 years ago

Useless and Impaled

58% 0:21 / 1:11:14

Useless and Impaled

Clips4sale 7 months ago

AB093 Camera Operator feminized drizzling-pegging (Asian and English subtitles)

AB093 Camera Operator feminized drizzling-pegging (Asian and English subtitles)

TrannyGem 1 month ago

Luccas & Jhordy Private Show

HD 2:00 / 12:20

Luccas & Jhordy Private Show

Flirt4Free 3 days ago

Thick Bad Dragon Busts my Boy Hole Wide Open pt 1 FULL VIDEO ON LAYNELOVEE MANYVIDS

Thick Bad Dragon Busts my Boy Hole Wide Open pt 1 FULL VIDEO ON LAYNELOVEE MANYVIDS

xHamster 1 year ago

Nick & Diego & Liam Private Show

47% HD 2:00 / 1:06:19

Nick & Diego & Liam Private Show

Flirt4Free 2 years ago

chastity office bitch spitroasted and quadruple creampied - full video on Veggiebabyy Manyvids

chastity office bitch spitroasted and quadruple creampied - full video on Veggiebabyy Manyvids

xHamster 1 year ago

Edging Lana to Multiple Ruined Orgasms after 4 weeks in a Chastity Cage

Edging Lana to Multiple Ruined Orgasms after 4 weeks in a Chastity Cage

Tranny.one 2 years ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

ShemaleSin 11 months ago

Taking My Chaste Sissy Bimbo Dolls Pegging Virginity with My Ding-Dong in Servitude by Mistresse Mercer

Taking My Chaste Sissy Bimbo Dolls Pegging Virginity with My Ding-Dong in Servitude by Mistresse Mercer

ShemaleSin 1 year ago

Unleash the chastity belt

Unleash the chastity belt

Trashreality 1 year ago

Sissy Humiliation with Thought Captions - College Boy has become Tranny Cocksucker Whore :'(

Sissy Humiliation with Thought Captions - College Boy has become Tranny Cocksucker Whore :'(

Tranny.one 2 years ago

Icy Hot Wooden Pony Self Bondage Torture

Icy Hot Wooden Pony Self Bondage Torture

xHamster 2 years ago

Matt & Oliver & Andres Private Show

64% HD 2:00 / 4:56

Matt & Oliver & Andres Private Show

Flirt4Free 2 years ago

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

53% HD 2:00 / 4:52

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

Flirt4Free 3 years ago

Step-mommy's yoga class sissy MP4

70% HD 0:24 / 7:10

Step-mommy's yoga class sissy MP4

Clips4sale 5 months ago

Chubby Ts Teen Stroking Cock

Chubby Ts Teen Stroking Cock

aShemaleTube 1 year ago

going out in public with my lovense remote control vibrator

60% 0:11 / 5:21

going out in public with my lovense remote control vibrator

veggiebabyy – feminization chastity and thick cock

veggiebabyy – feminization chastity and thick cock

VivaTube 10 months ago

Nicco & Patric & Santiago Have Amazing Threesome

61% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 1 year ago

Fuck Machine Ruined Anal Orgasm in Pink Chastity Cage

Fuck Machine Ruined Anal Orgasm in Pink Chastity Cage

xHamster 1 year ago

Im Pinch and Pull My Nipples

Im Pinch and Pull My Nipples

Flirt4Free 8 months ago

Colombian Boys Private Show

Colombian Boys Private Show

Flirt4Free 2 months ago

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

ShemaleSin 3 years ago

Master & Chris & Jepsen Private Show

46% HD 2:00 / 32:02

Master & Chris & Jepsen Private Show

Flirt4Free 2 years ago

MAKING LUNA A SLUT FOR OUR STRAPON COCKS 1080P - ELLIE IDOL, CHASTITY LYNN & LUNA LAIKA

64% HD 0:11 / 21:24

MAKING LUNA A SLUT FOR OUR STRAPON COCKS 1080P - ELLIE IDOL, CHASTITY LYNN & LUNA LAIKA

Clips4sale 2 years ago

Weekly train for crossdresser slut with nipple pumps

Weekly train for crossdresser slut with nipple pumps

xHamster 1 year ago

Trans Sissy Spunks in V-card

Trans Sissy Spunks in V-card

TransTube.tv 1 year ago

Proper punching and doubles

Proper punching and doubles

SexTubeSpot 3 years ago

Cock and ball bound extremely tight with pink rope until they turn dark purple and go numb and cold

Cock and ball bound extremely tight with pink rope until they turn dark purple and go numb and cold

xHamster 2 years ago

aquela gozada farta no cuzinho pra comecar o dia bem !!!

64% 0:26 / 8:45

aquela gozada farta no cuzinho pra comecar o dia bem !!!

PissVids 1 month ago

Just Be a Sissy

HD 1:01 / 15:45

Just Be a Sissy

FapHouse 6 months ago

Stella Locke Glasses Cute Ass Barebacking

Stella Locke Glasses Cute Ass Barebacking

aShemaleTube 5 years ago

Master & Ithan & Aleex Private Show

50% HD 2:00 / 28:59

Master & Ithan & Aleex Private Show

Flirt4Free 2 months ago

BG pegging - fucking and breeding my locked CD sissy bf

BG pegging - fucking and breeding my locked CD sissy bf

LoyalFans 1 year ago

Odd And Her Astolfo Romp Marionette

Odd And Her Astolfo Romp Marionette

TrannyGem 3 years ago

beautiful femboy rides big black cock on couch making herself moan with pleasure !

74% HD 0:50 / 50:16

beautiful femboy rides big black cock on couch making herself moan with pleasure !

AnalVids 9 months ago

JessieBbwSissy - Plapgasm 3 (Plapgasm Sissygasm is at 3:48)

JessieBbwSissy - Plapgasm 3 (Plapgasm Sissygasm is at 3:48)

xHamster 8 months ago

"Transsexual Domination - Big Dick Trans Whips Petite Blonde Slave"

"Transsexual Domination - Big Dick Trans Whips Petite Blonde Slave"

4KPorn 2 months ago

Sissy Anal invasion Super-bitch Locked Down on Giant Fake penis One Pub Jail Trussed & Taunted in Innocence Box by Dominatrix

Sissy Anal invasion Super-bitch Locked Down on Giant Fake penis One Pub Jail Trussed & Taunted in Innocence Box by Dominatrix

TransTube.tv 3 months ago

duas travesti foram malhar com as suas amigas e no final ate o professor entrou na suruba

duas travesti foram malhar com as suas amigas e no final ate o professor entrou na suruba

PissVids 1 year ago

Master & Ithan Private Show

Master & Ithan Private Show

Flirt4Free 1 month ago

Fem Chub Gay Big Ass

Fem Chub Gay Big Ass

xHamster 3 years ago

Sophia Loreen Private Show

50% 4K 2:00 / 22:25

Sophia Loreen Private Show

Flirt4Free 3 months ago

Sissy Oksana_ Assfuck training_sc.66

Sissy Oksana_ Assfuck training_sc.66

GayCK 3 years ago

squirt

Flirt4Free 3 months ago

Sperm shot ruined by chastity lockup

Sperm shot ruined by chastity lockup

SexTubeSpot 2 years ago

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

72% 0:16 / 5:26

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

PornBox 1 month ago

Hot Sissy in Chastity Squirts

Hot Sissy in Chastity Squirts

aShemaleTube 8 years ago

Trans Girl Tied and Teased

Trans Girl Tied and Teased

xHamster 1 year ago

Orianna Dunn Private Show

HD 2:00 / 23:58

Orianna Dunn Private Show

Flirt4Free 1 year ago

Harris Morrison Private Show

Harris Morrison Private Show

Flirt4Free 2 years ago

Sissy Aurelyy - Prostate Orgasms, Chastity and Pegging - Mistress Julia

66% HD 1:01 / 12:10

Sissy Aurelyy - Prostate Orgasms, Chastity and Pegging - Mistress Julia

FapHouse 3 weeks ago

Rachael Belle Exposed Sissy Slut Humiliation 3

Rachael Belle Exposed Sissy Slut Humiliation 3

aShemaleTube 2 months ago

Pledge and get spot for my group show..start now!!

63% HD 2:00 / 19:52

Pledge and get spot for my group show..start now!!

Flirt4Free 6 years ago

BNWO Sissy Bride Gooning

43% HD 0:29 / 12:01

BNWO Sissy Bride Gooning

Clips4sale 1 month ago

Master & Ithan Private Show

41% HD 2:00 / 31:39

Master & Ithan Private Show

Flirt4Free 3 months ago

Slobbery Suck Fingers

Slobbery Suck Fingers

Flirt4Free 5 months ago

Shemale Ass to mouth and Sissygasm in chastity Anal Squirt

Shemale Ass to mouth and Sissygasm in chastity Anal Squirt

xHamster 1 month ago

fizemos um menage bem gostoso com a vizinha da minha amiga

54% HD 0:22 / 7:34

fizemos um menage bem gostoso com a vizinha da minha amiga

PornBox 2 years ago

Sophia Loreen Party on May 8, 2025 - Part 2

59% 4K 2:00 / 1:03:20

Sophia Loreen Party on May 8, 2025 - Part 2

Flirt4Free 4 months ago

Ela tentando d.o.r.m.i.r e eu cheio de tesão, não deixei ela em paz enquanto eu não gozei várias vezes.

Premium HD 16:10

Ela tentando d.o.r.m.i.r e eu cheio de tesão, não deixei ela em paz enquanto eu não gozei várias vezes.

Sheer 6 months ago

Master & Christian & Nicco Private Show

45% HD 2:00 / 14:59

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

TGIRLSHOOKUP - HAVE A FUN 2 BOOTY OPEN BY THE SCREWING MACHINE

TGIRLSHOOKUP - HAVE A FUN 2 BOOTY OPEN BY THE SCREWING MACHINE

ShemaleSin 1 year ago

spooky goth succubus assfuck

spooky goth succubus assfuck

TransTube.tv 8 months ago

Warm sissy secretary drives BBC within chastity cage and latex gloves

Warm sissy secretary drives BBC within chastity cage and latex gloves

Kams.com 9 months ago

Cutie Reina Hanno Swinging Nipple Suction and Rubbing Chastity Precum

Cutie Reina Hanno Swinging Nipple Suction and Rubbing Chastity Precum

xHamster 1 year ago

Chubby Sub Sluts - Busty MILF Fucked Hard & Deep in Rough Anal Sex

Chubby Sub Sluts - Busty MILF Fucked Hard & Deep in Rough Anal Sex

Hoes.tube 2 months ago

Cute Trans Fucks Caged Tgirl!

Cute Trans Fucks Caged Tgirl!

XXXShemalePorn 1 year ago

Transformed husband into a slut and four more cocks and two dominatrixes

Transformed husband into a slut and four more cocks and two dominatrixes

xHamster 1 year ago

gang bang in sauna with stratgh and transexuel

Premium HD 13:35

gang bang in sauna with stratgh and transexuel

XVideosRed 1 year ago

Angela Lelli Private Show

58% HD 2:00 / 9:20

Angela Lelli Private Show

Flirt4Free 1 year ago

trans maid with braces cums from ribald anal - w0llip wollip

trans maid with braces cums from ribald anal - w0llip wollip

SortPorn 9 months ago

anime expo turns into anime orgy w/ 4 stunning asian baddies

70% HD 0:30 / 30:47

anime expo turns into anime orgy w/ 4 stunning asian baddies

PornBox 2 years ago

duas travesti do pau grande fizeram uma suruba com as suas amigas enquanto o macho delas nao dava conta

63% 0:27 / 9:19

duas travesti do pau grande fizeram uma suruba com as suas amigas enquanto o macho delas nao dava conta

PornBox 1 year ago

sissy spirit

aShemaleTube 5 years ago

Mmm My Thong is So Wet

Mmm My Thong is So Wet

Flirt4Free 3 months ago

23 year old fat sissy attempts first sissygasm

23 year old fat sissy attempts first sissygasm

xHamster 1 month ago

Hot Locked Sissy with Nano Chastity, craves to be Screwed

Hot Locked Sissy with Nano Chastity, craves to be Screwed

ShemaleSin 4 years ago

Adorable Sissy Virginity Gimp Let Out to be Taunted Denied Abased and Locked up by Domme Mercer

Adorable Sissy Virginity Gimp Let Out to be Taunted Denied Abased and Locked up by Domme Mercer

TrannyGem 3 years ago

suruba gostosa entre amigos duas bucetudas pra duas travesti do pauzao e o macho delas junto arrombar elas

63% HD 0:27 / 9:17

suruba gostosa entre amigos duas bucetudas pra duas travesti do pauzao e o macho delas junto arrombar elas

PornBox 1 year ago

Sissy slut rides

Sissy slut rides

xHamster 2 years ago

Chastity Prisoner Anal Hooked and Vibed

57% 0:23 / 48:28

Chastity Prisoner Anal Hooked and Vibed

Clips4sale 6 months ago

Sophia Loreen Private Show

59% HD 2:00 / 12:52

Sophia Loreen Private Show

Flirt4Free 1 month ago

Fucked into Sissy Slavery

43% HD 0:10 / 24:29

Fucked into Sissy Slavery

LoyalFans 2 years ago

amigas se pegando no ano novo

amigas se pegando no ano novo

PornBox 8 months ago

Fizemos um menage bem gostoso com a vizinha da minha amiga

Premium HD 7:34

Fizemos um menage bem gostoso com a vizinha da minha amiga

xnxxGold 2 years ago

Wild Sabrina Members-Only Show

63% HD 2:00 / 20:53

Wild Sabrina Members-Only Show

Flirt4Free 4 years ago

Priscila Araújo gave the black boy super-hot and then wooed him to lose his chastity by providing his butt for the very first time

Priscila Araújo gave the black boy super-hot and then wooed him to lose his chastity by providing his butt for the very first time

KeekAss 3 years ago

Feelipe & Adara Private Show

64% HD 2:00 / 4:26

Feelipe & Adara Private Show

Flirt4Free 2 months ago

Emily Leah Private Show

4K 2:00 / 10:29

Emily Leah Private Show

Flirt4Free 2 months ago

dickgirl detention 2 - sammi

58% HD 0:30 / 25:45

dickgirl detention 2 - sammi

PornBox 1 year ago

Sissy femboy 19years old boy INDIGO WHITE FEMBOY HOOTERS STRIP TEASE!

Sissy femboy 19years old boy INDIGO WHITE FEMBOY HOOTERS STRIP TEASE!

xHamster 1 year ago

Latex Rubber Doll Anal Training in Chastity MollyEra 72

Latex Rubber Doll Anal Training in Chastity MollyEra 72

Eporner 1 year ago

T Chick Lena Vesper Takes Monster Fuck Sticks On Her Bang Machine

T Chick Lena Vesper Takes Monster Fuck Sticks On Her Bang Machine

TrannyGem 9 months ago

Sissy Princess getting fucked by big black King

Sissy Princess getting fucked by big black King

xHamster 2 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 2 years ago

Jhordy & Maxx Private Show

63% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 1 month ago

Ballbusting handsfree

Ballbusting handsfree

ShemaleSin 5 months ago

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