Chastity Videos - Trans (48,649)

”Tranny is pissing over her prolapped booty”

”Tranny is pissing over her prolapped booty”

Faptor 4 months ago

TS Ana All Taped Up and Smoothly Tape Gagged

69% 0:33 / 11:54

TS Ana All Taped Up and Smoothly Tape Gagged

Clips4sale 1 year ago

Petite dong locked in chastity and leaking juicy pants

Petite dong locked in chastity and leaking juicy pants

ShemaleSin 1 year ago

Soon to be Neutered Chastised Sissy Worships Pussy

Soon to be Neutered Chastised Sissy Worships Pussy

TrannyGem 7 years ago

BIG BLACK COCK vs Sissy dick comparison & oral pleasure - Parent abased me! @ Sasha_de_Sade on all sites

BIG BLACK COCK vs Sissy dick comparison & oral pleasure - Parent abased me! @ Sasha_de_Sade on all sites

TransTube.tv 11 months ago

Young Sissy Femboy rails a humungous jizz-shotgun and jizzes sans forearms

Young Sissy Femboy rails a humungous jizz-shotgun and jizzes sans forearms

TrannyGem 3 years ago

Enjoy my nude body and my round ass bouncing in a good dildo! lets cum together! - Part 2

Enjoy my nude body and my round ass bouncing in a good dildo! lets cum together! - Part 2

Flirt4Free 9 months ago

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

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

xHamster 1 month ago

Mommy Holy - Feminization - Time For Your First Chastity

Mommy Holy - Feminization - Time For Your First Chastity

xHamster 1 year ago

slim American brunette transgirl in stockings toys ass on webcam

slim American brunette transgirl in stockings toys ass on webcam

aShemaleTube 3 years ago

Fuck Machine Threesome

Fuck Machine Threesome

XVideos 6 months ago

Harris Morrison Private Show

HD 2:00 / 1:08:29

Harris Morrison Private Show

Flirt4Free 2 years ago

2024.08.23 crossdresser machine fuck

2024.08.23 crossdresser machine fuck

xHamster 1 year ago

Sissy Femboy in Pinkish Wool Coat liquidates their Innocence Box

Sissy Femboy in Pinkish Wool Coat liquidates their Innocence Box

TrannyGem 1 year ago

Milk or Tea?

69% HD 1:01 / 9:43

FapHouse 4 months ago

TGIRLSHOOKUP: Serena Bubbles Is A Masochist Freak!

TGIRLSHOOKUP: Serena Bubbles Is A Masochist Freak!

ShemaleSin 2 years ago

Tiny Dick Futa StepSister 2

Tiny Dick Futa StepSister 2

Pornzona 1 month ago

Sophia Loreen Private Show

HD 2:00 / 16:54

Sophia Loreen Private Show

Flirt4Free 4 years ago

Trans Chastity Slut Dusti Bunni Gets Leashed & Used By Stud

Trans Chastity Slut Dusti Bunni Gets Leashed & Used By Stud

PornUse 1 year ago

ESSA POSIÇÃO É FATAL... Faço meu namorado gozar muito rápido e me dar muito leite delirando de prazer

Premium HD 5:26

ESSA POSIÇÃO É FATAL... Faço meu namorado gozar muito rápido e me dar muito leite delirando de prazer

Sheer 8 months ago

Leaking Jizm As She's Plumbed On All 4S

Leaking Jizm As She's Plumbed On All 4S

TrannyGem 3 years ago

Mommy Holy - JOI CEI - My Special Juices Are For Baby Boy - in Chastity

Mommy Holy - JOI CEI - My Special Juices Are For Baby Boy - in Chastity

xHamster 1 year ago

Chastity She Wans Me In Chastity Aftr Almos 2 Weeks Of Not Cumming She Allow My Masturbate Big Cum My Vicious Transgirl

Chastity She Wans Me In Chastity Aftr Almos 2 Weeks Of Not Cumming She Allow My Masturbate Big Cum My Vicious Transgirl

xHamster 3 years ago

Big tits milf Veronica Avluv fucked deep

Big tits milf Veronica Avluv fucked deep

xHamster 7 years ago

Stepdad Fucks his Petite TS Stepdaughter Raw Until he Squirts a Creamy Load (free)

Stepdad Fucks his Petite TS Stepdaughter Raw Until he Squirts a Creamy Load (free)

XVideos 8 months ago

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

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

Lesbian8 5 months ago

Lime sissygasms whilst riding on horsecock

Lime sissygasms whilst riding on horsecock

ShemaleSin 2 months ago

Mommy Holy - JOI - Lock you in Chastity then Anal Milking

Mommy Holy - JOI - Lock you in Chastity then Anal Milking

xHamster 1 year ago

”Amai Liu, Chastity Lynn, Jynx Maze & Lily Labeau take turns on a huge cock in this cumshot compilation”

”Amai Liu, Chastity Lynn, Jynx Maze & Lily Labeau take turns on a huge cock in this cumshot compilation”

TransHero 4 months ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 2 weeks ago

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

44% HD 0:10 / 14:09

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

LoyalFans 1 year ago

sissy slut in pink heels fucks her ass and cums in cage

66% 0:12 / 8:33

sissy slut in pink heels fucks her ass and cums in cage

Clips4sale 2 years ago

Rock-hard and Wild Hotel Smashing!!!! Onlyfans/Manyvids Preview

Rock-hard and Wild Hotel Smashing!!!! Onlyfans/Manyvids Preview

TransTube.tv 1 year ago

trans egirl gapes with bad dragon and fists her pussy

66% 0:13 / 12:25

trans egirl gapes with bad dragon and fists her pussy

Clips4sale 2 years ago

Jessy Jones In Shemale Ass Sex Fucks Sub In Chastity

Jessy Jones In Shemale Ass Sex Fucks Sub In Chastity

PornUse 4 months ago

Latex Sissy Chokes Vibes Chastity to Gushing Self Bondage Ruin

Latex Sissy Chokes Vibes Chastity to Gushing Self Bondage Ruin

JuicyTrans 1 week ago

Sisk Cum Filled Condom Collection

Sisk Cum Filled Condom Collection

xHamster 2 years ago

MINHA SECRET&Aacute_RIA VEIO ME PEDIR UM AUMENTO E EU DEI EM TROCA DE ELA TRANSAR COMIGO E ELA ACEITOU - COMPLETO NO RED - EVEZZINI

MINHA SECRET&Aacute_RIA VEIO ME PEDIR UM AUMENTO E EU DEI EM TROCA DE ELA TRANSAR COMIGO E ELA ACEITOU - COMPLETO NO RED - EVEZZINI

XVideos 2 months ago

NOVINHA TRANS COMENDO A BUCETINHA DA GR&Aacute_VIDA ENQUANTO O CORNO ASSISTE!

NOVINHA TRANS COMENDO A BUCETINHA DA GR&Aacute_VIDA ENQUANTO O CORNO ASSISTE!

XVideos 5 months ago

Harris Morrison Private Show

HD 2:00 / 28:37

Harris Morrison Private Show

Flirt4Free 3 years ago

Don't You Love Hucow Pink and Blue Gals

71% 0:29 / 8:53

Don't You Love Hucow Pink and Blue Gals

Clips4sale 1 year ago

Chastity cage and bang machine makes ideal cum

Chastity cage and bang machine makes ideal cum

Amateur8 2 months ago

Blonde Sissy Kitten Maddy Jones Oiling Up Her Ass And Stuffing A Big Dildo In Her Holes

Blonde Sissy Kitten Maddy Jones Oiling Up Her Ass And Stuffing A Big Dildo In Her Holes

xHamster 5 months ago

Nagatoro and lilly the succubi (REWORKED)

Nagatoro and lilly the succubi (REWORKED)

XVideos 7 months ago

Sissy bitch in sexy lingerie and chastity belt rides a big dildo and fucks her asshole with her fing

Sissy bitch in sexy lingerie and chastity belt rides a big dildo and fucks her asshole with her fing

BoyFriendTV 4 months ago

Uber-Cute Sissy In lube and a innocence plows herself in the butt with a massive chisel

Uber-Cute Sissy In lube and a innocence plows herself in the butt with a massive chisel

TrannyGem 3 years ago

Free Use Submissive Maid Tgirl Anal Face Fuck Service Slut

Premium HD 34:16

Free Use Submissive Maid Tgirl Anal Face Fuck Service Slut

Sheer 1 year ago

Wearing a tiny chastity cage and peeing in a diaper

Wearing a tiny chastity cage and peeing in a diaper

Fapcat 3 years ago

isabelly ferreira, rosy pinheiro, fabi moranguinho e rafaella gabrielly

63% 0:30 / 15:58

isabelly ferreira, rosy pinheiro, fabi moranguinho e rafaella gabrielly

PornBox 4 months ago

Perfect sissy slave in chastity fucked by strapon Mistress

Perfect sissy slave in chastity fucked by strapon Mistress

AbTranny 6 years ago

Harris Morrison Private Show

HD 2:00 / 18:14

Harris Morrison Private Show

Flirt4Free 1 year ago

“DOES THAT PERCEIVE FINE BABYGIRL?” SIZZLING RAUNCHY FUR COVERED ORGY TOON (@berryguild @stitchiot)

“DOES THAT PERCEIVE FINE BABYGIRL?” SIZZLING RAUNCHY FUR COVERED ORGY TOON (@berryguild @stitchiot)

Transvids.tv 10 months ago

I collected 2 SISSYGASMS after PEGGING

I collected 2 SISSYGASMS after PEGGING

xHamster 1 year ago

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

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

XVideos 5 months ago

Unfathomable Anal Horse Weenie Sex-toy Screwing Machine - Jessica Bloom

Unfathomable Anal Horse Weenie Sex-toy Screwing Machine - Jessica Bloom

ShemaleSin 1 year ago

COMECEI LAMBENDO SEU PEZINHOS... depois fui para seu cuzinho at&eacute_ fazer ela gozar, coloquei a safada de quatro e empinou o rabo pra mim meter at&eacute_ encher o seu cu de leite!

COMECEI LAMBENDO SEU PEZINHOS... depois fui para seu cuzinho at&eacute_ fazer ela gozar, coloquei a safada de quatro e empinou o rabo pra mim meter at&eacute_ encher o seu cu de leite!

XVideos 11 months ago

How To Part two: Inverted Chastity :)

How To Part two: Inverted Chastity :)

ShemaleSin 1 year ago

Tropical threesome that makes him surrender

71% 4K 0:21 / 22:10

Tropical threesome that makes him surrender

Clips4sale 2 years ago

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

Premium HD 32:52

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

XVideosRed 4 months ago

Futanari threesome with femboy. 2 Futas ravage one guy

Futanari threesome with femboy. 2 Futas ravage one guy

TransTube.tv 1 year ago

Sissy BNWO castration bands its balls for headmistress 1hr goons white extinction beauty scarlett ebony

Sissy BNWO castration bands its balls for headmistress 1hr goons white extinction beauty scarlett ebony

ShemaleSin 3 years ago

Bondage sissy sluts using furniture and strapon in ass

Bondage sissy sluts using furniture and strapon in ass

xHamster 1 year ago

Paola Balconi Private Show

HD 2:00 / 10:41

Paola Balconi Private Show

Flirt4Free 1 year ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

XVideos 6 months ago

Chastity Prisoner Anal Hooked and Vibed

61% 0:23 / 48:28

Chastity Prisoner Anal Hooked and Vibed

Clips4sale 1 year ago

Vibrator Ruining in Nylon Catsuit

68% HD 0:10 / 14:52

Vibrator Ruining in Nylon Catsuit

Clips4sale 4 years ago

Caged Sissy Secretary Rides Thick Anal Dildo

75% HD 0:39 / 28:06

Caged Sissy Secretary Rides Thick Anal Dildo

FapHouse 11 months ago

Nylon Sissy Slave - Candle Boxxx HDMP4

42% 0:14 / 13:03

Nylon Sissy Slave - Candle Boxxx HDMP4

Clips4sale 2 years ago

Franceska Jaimes and Chastity Lynn stranlesb

Franceska Jaimes and Chastity Lynn stranlesb

AbTranny 6 years ago

Submissive trans girl Suffers Mindfuck Electric Shock Timer Game

56% HD 0:28 / 24:56

Submissive trans girl Suffers Mindfuck Electric Shock Timer Game

Clips4sale 1 year ago

laced and loaded scene #590

57% HD 1:36 / 50:01

laced and loaded scene #590

PornBox 12 years ago

2025 Trans Anal & Cum Compilation Pt 1

4K 0:41 / 52:42

2025 Trans Anal & Cum Compilation Pt 1

Clips4sale 6 months ago

ABH054 Sweet girl in chastity riding dildo and play vibrator until cum

67% HD 0:29 / 35:43

ABH054 Sweet girl in chastity riding dildo and play vibrator until cum

Clips4sale 4 years ago

FUI DAR AULA DE VIOL&Atilde_O PRA MINHA ALUNA E ELA ACABOU TRANSANDO COMIGO - EVEZZINI

FUI DAR AULA DE VIOL&Atilde_O PRA MINHA ALUNA E ELA ACABOU TRANSANDO COMIGO - EVEZZINI

XVideosRed 4 months ago

sissy sith lord fucks herself with her lightsaber dildo

sissy sith lord fucks herself with her lightsaber dildo

Clips4sale 1 year 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

PovRZ 1 year ago

Luccas & Jhordy Private Show

43% HD 2:00 / 18:11

Luccas & Jhordy Private Show

Flirt4Free 11 months ago

Sandy Lee Private Show

Sandy Lee Private Show

Flirt4Free 9 years ago

Black TS Girl Chastity Michaels Gets Her Big Cock Sucked

Black TS Girl Chastity Michaels Gets Her Big Cock Sucked

TrannyGem 1 year ago

Sissy Task for Sissies

57% HD 0:20 / 6:11

Sissy Task for Sissies

Clips4sale 1 year ago

easter snowbunny plaps in chastity cage with BBC and cums

51% 4K 0:15 / 8:38

easter snowbunny plaps in chastity cage with BBC and cums

Clips4sale 1 year ago

BBC owned sissy gapes hole and fills her ass with black seed

BBC owned sissy gapes hole and fills her ass with black seed

Clips4sale 1 year ago

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

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

Sheer 1 year ago

CHASTITY TRAINING // Transgirl Plugs her Butt and Cums whilst Caged // Milky Lynn

CHASTITY TRAINING // Transgirl Plugs her Butt and Cums whilst Caged // Milky Lynn

ShemaleSin 6 months ago

Sissy Maid Cleaning Bathroom in Steel Chastity Belt with Dildo Locked in Place

Sissy Maid Cleaning Bathroom in Steel Chastity Belt with Dildo Locked in Place

xHamster 3 years ago

Chinese sissy marionette in v-card and Leash

Chinese sissy marionette in v-card and Leash

TrannyGem 2 years ago

Premature-Ejaculation or Chastity Challenge

56% 0:28 / 10:31

Premature-Ejaculation or Chastity Challenge

Clips4sale 3 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 3 years ago

Nettle punishment for pussyfree idiot

Nettle punishment for pussyfree idiot

xHamster 1 year ago

QoS sissy squirts cum in chastity while BBC rails her

55% 0:11 / 12:14

QoS sissy squirts cum in chastity while BBC rails her

Clips4sale 1 year ago

easter bunny gets stretched out by two BBCs and cums in cage

58% HD 0:14 / 13:20

easter bunny gets stretched out by two BBCs and cums in cage

Clips4sale 1 year ago

AB2509 Locked three months Cute femboy cum in flashlight with e-plug 3个月没射可爱小男娘!电击肛塞飞机杯高潮喷发

AB2509 Locked three months Cute femboy cum in flashlight with e-plug 3个月没射可爱小男娘!电击肛塞飞机杯高潮喷发

aShemaleTube 6 months ago

Redhead Caged Trans Slut Sammi Gets BBC Creampie From Lord Panda!

Redhead Caged Trans Slut Sammi Gets BBC Creampie From Lord Panda!

XVideos 6 months ago

ENCONTREI UM NOVINHO NA PRAIA E ELE COMEU FIRME MEU CU - COMPLETO NO RED - LUANA PRADO

ENCONTREI UM NOVINHO NA PRAIA E ELE COMEU FIRME MEU CU - COMPLETO NO RED - LUANA PRADO

XVideos 4 months ago

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

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

xHamster 1 year ago

Slamming Sammi Smith&#039_s Tight Pink Transgirl Asshole Full of BBC

Slamming Sammi Smith&#039_s Tight Pink Transgirl Asshole Full of BBC

XVideos 7 months ago

active trans girl celine dijjon waiting for get fuckeck by me in hotel

60% 0:27 / 9:10

active trans girl celine dijjon waiting for get fuckeck by me in hotel

PornBox 1 year ago

Breaking In The Bimbo (full scene 4k)

4K 0:21 / 41:48

Breaking In The Bimbo (full scene 4k)

IWantClips 3 years ago

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 1 wmv

56% 0:11 / 15:16

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 1 wmv

Clips4sale 3 years ago

Akatsuki Cosplay Ass Gaped Cum Gushes Chakra Drained Creampie Leak

Akatsuki Cosplay Ass Gaped Cum Gushes Chakra Drained Creampie Leak

JuicyTrans 2 weeks ago

NOVINHO CHEIO DE TES&Atilde_O COMEU MEU CUZINHO E AINDA SE MASTURBOU JUNTO COMIGO - COMPLETO NO RED - LUANA PRADO

NOVINHO CHEIO DE TES&Atilde_O COMEU MEU CUZINHO E AINDA SE MASTURBOU JUNTO COMIGO - COMPLETO NO RED - LUANA PRADO

XVideos 1 month ago

Sexy blonde transsexual fucks him hard

HD 1:01 / 18:11

Sexy blonde transsexual fucks him hard

FapHouse 6 years ago

Sissy Maid in Spiked Chastity Cage Cuffed to Couch Post

Sissy Maid in Spiked Chastity Cage Cuffed to Couch Post

ShemaleSin 2 years ago

Nelly Gale Private Show

57% 4K 2:00 / 11:36

Nelly Gale Private Show

Flirt4Free 2 weeks ago

Elias & Elix Private Show

63% HD 2:00 / 21:57

Elias & Elix Private Show

Flirt4Free 6 months ago

POV Trans Femdom, Suck My Knob During the time that in Chastity U Sissy Doxy!

POV Trans Femdom, Suck My Knob During the time that in Chastity U Sissy Doxy!

Lesbian8 4 months ago

Lily Eden Gags on a Vibrator Whilst Caged, Cuffed, and Clamped

Lily Eden Gags on a Vibrator Whilst Caged, Cuffed, and Clamped

ShemaleSin 6 months ago

A sissy in stockings, high heels and a chastity belt pees over a small penis

A sissy in stockings, high heels and a chastity belt pees over a small penis

xHamster 1 week ago

Blowjob

Flirt4Free 2 years ago

Anal depth training in chastity

Anal depth training in chastity

ShemaleSin 1 year ago

Jessica Bloom Spit-Roasted &amp_ Machine-Fucked! Throbbing Cocks DP Her Holes Massive Facial &amp_ Cum Swallow

Jessica Bloom Spit-Roasted &amp_ Machine-Fucked! Throbbing Cocks DP Her Holes Massive Facial &amp_ Cum Swallow

XVideos 1 month ago

T-Doll Nutting On Bad Dragon Opportunity

T-Doll Nutting On Bad Dragon Opportunity

TrannyGem 4 years ago

Trans Domme turns two straight boys into bi guys for a load of her cum

71% 0:09 / 36:30

Trans Domme turns two straight boys into bi guys for a load of her cum

Clips4sale 2 years ago

Redhead trans in chastity pounded and bred by BBC

Redhead trans in chastity pounded and bred by BBC

Amateur8 2 months ago

TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl

52% HD 0:54 / 24:52

TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl

Clips4sale 1 year ago

Sissy gets knotted and gives a muddy fellate

Sissy gets knotted and gives a muddy fellate

TrannyGem 1 year ago

Hardcore Anal Sissy TGirl Pool Orgy With Ria Bentley and Friends

69% HD 0:33 / 31:25

Hardcore Anal Sissy TGirl Pool Orgy With Ria Bentley and Friends

Clips4sale 1 year ago

Pathetic Chastity and Satin amateur sissy webcam whore gets used by online Daddy w/ CUMSHOT

Pathetic Chastity and Satin amateur sissy webcam whore gets used by online Daddy w/ CUMSHOT

YouPorn Unknown

Feminization punishment from teacher

53% HD 0:20 / 12:25

Feminization punishment from teacher

Clips4sale 1 year ago

Sissy slave in self bondage with shock collar

Sissy slave in self bondage with shock collar

xHamster 7 months ago

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