Chastity Videos - Trans (65,707)

Sharing a Massive Trans BBC with My Wife While She Watched Me Take a Huge Creampie in My Blonde Ass

HD 0:39 / 15:41

Sharing a Massive Trans BBC with My Wife While She Watched Me Take a Huge Creampie in My Blonde Ass

FapHouse 3 days ago

Cock in a cage and dildo in the ass, this shemale made a perfect solo

Cock in a cage and dildo in the ass, this shemale made a perfect solo

XGroovy 2 years ago

The Bride has a Cock!

The Bride has a Cock!

XHamster 3 years ago

tart stuck in her v-card box leaks precum from porking her guts

tart stuck in her v-card box leaks precum from porking her guts

TrannyGem 3 years ago

Sophia Loreen Private Show

HD 2:00 / 15:34

Sophia Loreen Private Show

Camster 1 week ago

Humiliated Sissy Custom #2

57% HD 0:10 / 14:23

Humiliated Sissy Custom #2

LoyalFans 1 year ago

First Anal Sissygasm

71% HD 1:01 / 9:36

First Anal Sissygasm

FapHouse 1 year ago

Too Tempting to Look Away.

Too Tempting to Look Away.

Camster 1 week ago

Sissy Hope During an Anal Prolapse Training Session

HD 1:01 / 14:23

Sissy Hope During an Anal Prolapse Training Session

FapHouse 3 months ago

Big Tits Stepmom Part 2

64% VR 0:08 / 3:08

Big Tits Stepmom Part 2

FapHouse 2 weeks ago

Hotel Sex Fantasy

65% HD 1:01 / 20:50

Hotel Sex Fantasy

FapHouse 4 months ago

trans maid with braces shoots a load from grubby ass fucking - w0llip wollip

trans maid with braces shoots a load from grubby ass fucking - w0llip wollip

Transvids.tv 1 year ago

Bonnie Boombelle Private Show

4K 2:00 / 26:27

Bonnie Boombelle Private Show

Camster 2 weeks ago

transgender princess Makes You Learn To Love BIG BLACK COCK

transgender princess Makes You Learn To Love BIG BLACK COCK

TrannyGem 2 years ago

Good sluts must remain in chastity

55% HD 0:10 / 44:33

Good sluts must remain in chastity

LoyalFans 1 month ago

Stepdaughter Skipping College to Get Fucked by Machine and Squirt Cum Like a Sissy Slut

HD 0:39 / 20:49

Stepdaughter Skipping College to Get Fucked by Machine and Squirt Cum Like a Sissy Slut

FapHouse 10 months ago

Chastity T-Girl goes wet, Claire Tenebrarum, 5on1, Anal Fisting, DAP, Gapes, Pee Drink, Swallow BTG063

Premium 63% 1:01:51

Chastity T-Girl goes wet, Claire Tenebrarum, 5on1, Anal Fisting, DAP, Gapes, Pee Drink, Swallow BTG063

XVideosRed 4 years ago

Cute Sissy Kitty

66% 0:39 / 1:08

Cute Sissy Kitty

FapHouse 1 month ago

Down Low Guy Fucks Sissy For First Time

HD 0:10 / 22:13

Down Low Guy Fucks Sissy For First Time

LoyalFans 3 weeks ago

Sissy Kanisa Put on Cute Fluffy Dress

63% 1:01 / 14:22

Sissy Kanisa Put on Cute Fluffy Dress

FapHouse 1 year ago

She Accidentally Shoots A Load Rock Hard In Her Box While Edging

She Accidentally Shoots A Load Rock Hard In Her Box While Edging

TrannyGem 1 year ago

Cuck Confessions - the Sissy Cuck: She Needed a Real Man

66% HD 0:39 / 35:33

Cuck Confessions - the Sissy Cuck: She Needed a Real Man

FapHouse 7 months ago

Cute tranny fucked in tiny chastity bareback

Cute tranny fucked in tiny chastity bareback

XHamster 9 months ago

Sophia Loreen Party on Jul 18, 2026 - Part 3

HD 2:00 / 48:02

Sophia Loreen Party on Jul 18, 2026 - Part 3

Camster 1 week ago

TRANSFIXED - Newlywed Emma Magnolia Caught by Bridesmaid September Reign & Wife Emma Rose! DP SURPRISE

TRANSFIXED - Newlywed Emma Magnolia Caught by Bridesmaid September Reign & Wife Emma Rose! DP SURPRISE

Some.Porn 1 year ago

Cockslut Released From Chastity

Cockslut Released From Chastity

Tranny.one 4 years ago

Shiny ass riding a pink toy

71% HD 0:39 / 18:06

Shiny ass riding a pink toy

FapHouse 3 years ago

Rough Anal with Huge Dildo Makes Sissy Squirt

70% 0:39 / 16:29

Rough Anal with Huge Dildo Makes Sissy Squirt

FapHouse 1 month ago

Nicco & Patric & Santiago Have Amazing Threesome

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

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

Latex Chastity Cage Sissy on Sex Machine Pillory, Dildo and Estim Part 3

Latex Chastity Cage Sissy on Sex Machine Pillory, Dildo and Estim Part 3

FapHouse 1 year ago

Sophia Loreen Party on Jul 25, 2026 - Part 3

HD 2:00 / 41:09

Sophia Loreen Party on Jul 25, 2026 - Part 3

Camster 1 day ago

Chastity Slave with Catheter

55% HD 0:39 / 18:53

Chastity Slave with Catheter

FapHouse 5 months ago

BBC creampies white cd

BBC creampies white cd

AShemaleTube 3 years ago

emily adaire daped and fisted

70% HD 1:36 / 1:04:44

emily adaire daped and fisted

AnalVids 4 years ago

Sissy Lockdown - Whispers and Wallet Ruin in My Glasses Clip by Findom Goaldigger

Sissy Lockdown - Whispers and Wallet Ruin in My Glasses Clip by Findom Goaldigger

FapHouse 8 months ago

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

XHamster 4 months ago

Sophia Loreen Party on Jul 7, 2026 - Part 4

HD 2:00 / 12:22

Sophia Loreen Party on Jul 7, 2026 - Part 4

Camster 2 weeks ago

He so Wants to Cum, but His Hands and Head Are Shackled!

57% HD 0:39 / 2:18

He so Wants to Cum, but His Hands and Head Are Shackled!

FapHouse 2 years ago

Chaste Guy Has to Fuck Sweet Tranny Girl with Strapon

59% HD 0:39 / 10:48

Chaste Guy Has to Fuck Sweet Tranny Girl with Strapon

FapHouse 6 months ago

IT IS MORE DELICIOUS AS A FAMILY LLE019

Premium HD 29:50

IT IS MORE DELICIOUS AS A FAMILY LLE019

XVideosRed 5 years ago

Healthy Ballbusting Session

Healthy Ballbusting Session

XHamster 3 weeks ago

Chubby alt femboy in stockings got BBC into her ass compilation

Chubby alt femboy in stockings got BBC into her ass compilation

MyLust 1 year ago

Tiny Chastity Belt Licking - Emily & Justin

55% 1:01 / 6:49

Tiny Chastity Belt Licking - Emily & Justin

FapHouse 3 years ago

sissygasm caged Compilation

sissygasm caged Compilation

XHamster 3 years ago

Anal Bash

FapHouse 1 month ago

Lily Demure: Please Suck on Me

Lily Demure: Please Suck on Me

FapHouse 1 year ago

Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass

Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass

XHamster 3 years ago

Sissy Cow Maddy Loves Tasting Her Own Ass

Sissy Cow Maddy Loves Tasting Her Own Ass

XHamster 5 months ago

Sissy crossdresser plays with chastity device

61% HD 0:39 / 5:52

Sissy crossdresser plays with chastity device

FapHouse 8 years ago

Femdom Humiliation Sissy Training My Maid

54% HD 1:01 / 12:37

Femdom Humiliation Sissy Training My Maid

FapHouse 3 months ago

Locked in Permanent Chastity - Sissy Bitch Begs for BBC Part 2

55% HD 0:39 / 4:16

Locked in Permanent Chastity - Sissy Bitch Begs for BBC Part 2

FapHouse 6 months ago

Crossdresser in Chastity Gets Dressed and Dildo Fucked

Crossdresser in Chastity Gets Dressed and Dildo Fucked

XHamster 1 month ago

Hardcore Trans Slut Wanking Until She Cums - No Mercy, Just Pleasure

Hardcore Trans Slut Wanking Until She Cums - No Mercy, Just Pleasure

XHamster 1 month ago

Feet & Cock in Chastity

66% HD 1:01 / 15:07

Feet & Cock in Chastity

FapHouse 1 year ago

Femme Sandy - Bare in the Bushes: Exposure Walk & Swallowing

Femme Sandy - Bare in the Bushes: Exposure Walk & Swallowing

XHamster 5 months ago

Fucking with Hammer Drill Machine

53% HD 0:39 / 8:06

Fucking with Hammer Drill Machine

FapHouse 2 months ago

The Chastity Rabbit Hole

47% HD 0:39 / 9:03

The Chastity Rabbit Hole

FapHouse 1 year ago

Do You Like My Outfit?

61% HD 0:08 / 1:02

Do You Like My Outfit?

FapHouse 1 year 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

Femboy Cumshot

FapHouse 5 days ago

Femboy Piss and Flash Her Hot Feminized Body Outdoor Piss While in Chastity Cage and Rub Her Small Flaccid Cock

55% HD 0:39 / 13:00

Femboy Piss and Flash Her Hot Feminized Body Outdoor Piss While in Chastity Cage and Rub Her Small Flaccid Cock

FapHouse 1 year ago

Serious Chastity

54% 0:39 / 1:52

Serious Chastity

FapHouse 3 weeks ago

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

XHamster 9 months ago

Trans Chastity Bang Doll - unfathomable and coarse anal banging

Trans Chastity Bang Doll - unfathomable and coarse anal banging

Lesbian8 6 months ago

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

XVideosRed 2 years ago

TS Becki Bottomz Deepthroating and Riding

HD 0:10 / 12:16

TS Becki Bottomz Deepthroating and Riding

LoyalFans 3 weeks ago

The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)

54% 0:30 / 58:28

The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)

Clips4sale 1 year ago

3 Min Machine Fuck --- Dildo Too Small to Feel

3 Min Machine Fuck --- Dildo Too Small to Feel

FapHouse 1 year ago

Sissyfication 2

67% HD 0:39 / 9:48

Sissyfication 2

FapHouse 1 year ago

Sweetie assistant public remote manage

Sweetie assistant public remote manage

TrannyGem 4 years ago

Little whit nylon panty public walk in chastity cage.

Little whit nylon panty public walk in chastity cage.

XHamster 2 years ago

Very Sexy Sissy Bounces on Big Cock Until She Squirts

Very Sexy Sissy Bounces on Big Cock Until She Squirts

FapHouse 1 week ago

Cutie Reina Hanno Swinging Nipple Suction and Rubbing Chastity Precum

Cutie Reina Hanno Swinging Nipple Suction and Rubbing Chastity Precum

FapHouse 1 year ago

Naughty Mrs. Clause

57% HD 1:01 / 10:56

Naughty Mrs. Clause

FapHouse 1 year 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

Dominant shemale screwing another one very hard

Dominant shemale screwing another one very hard

AShemaleTube 2 years ago

The Reward for the Locked-up Sissy

The Reward for the Locked-up Sissy

XHamster 8 months ago

Sissy Training

XHamster 1 year ago

Sophia Loreen Private Show

55% 4K 2:00 / 58:12

Sophia Loreen Private Show

Flirt4Free 1 year ago

Sophia Loreen Party on Jul 17, 2026 - Part 4

HD 2:00 / 43:44

Sophia Loreen Party on Jul 17, 2026 - Part 4

Camster 1 week ago

Sissy Joyce fucked by a Big Black Cock

57% HD 1:01 / 10:04

Sissy Joyce fucked by a Big Black Cock

FapHouse 3 years ago

Sweet Chastity 11

Sweet Chastity 11

AShemaleTube 7 months ago

Lucy Torn gets dominated & pounded by a BBC at She-World Bang-Out Pub

Lucy Torn gets dominated & pounded by a BBC at She-World Bang-Out Pub

TrannyMovs 1 month ago

Rachael Found Your Key

78% HD 1:01 / 13:18

Rachael Found Your Key

FapHouse 1 year ago

Perverted in My Car

Perverted in My Car

FapHouse 1 year ago

Fucking Trans Woman in Chastity - Compilation 5

Fucking Trans Woman in Chastity - Compilation 5

XHamster 5 months ago

Sexy secretary talks about small in meeting room

Sexy secretary talks about small in meeting room

Some.Porn 2 years ago

Aron & Elvis & Stivens Private Show

71% HD 2:00 / 5:06

Aron & Elvis & Stivens Private Show

Flirt4Free 3 years ago

Cutie assistant public remote manage

Cutie assistant public remote manage

TrannyGem 5 years ago

SISSY MONIQUE - The partywhore (Part 1)

SISSY MONIQUE - The partywhore (Part 1)

XHamster 1 year ago

Feminized and Fucked by My Strapon

49% HD 0:10 / 9:53

Feminized and Fucked by My Strapon

LoyalFans 2 years ago

Sophia Loreen Private Show

62% HD 2:00 / 31:53

Sophia Loreen Private Show

Flirt4Free 2 months ago

QOS sissy rides BBC, bust her balls, and squirts out of cage

63% 0:11 / 11:43

QOS sissy rides BBC, bust her balls, and squirts out of cage

Clips4sale 2 years ago

Your Favorite Distraction

Your Favorite Distraction

Camster 1 month ago

Sissy Jessica Bloom Tries Out 5 Different Types of Chastity Cage

Sissy Jessica Bloom Tries Out 5 Different Types of Chastity Cage

ShemaleSin 3 months ago

Chastity belt Yellow PVC Bodysuit Sissy Sex Toy multiple Orgasm and solo cum

Chastity belt Yellow PVC Bodysuit Sissy Sex Toy multiple Orgasm and solo cum

XHamster 11 months ago

Sophia Loreen Private Show

61% HD 2:00 / 13:06

Sophia Loreen Private Show

Camster 1 month ago

SisK plug and play her anal with a purple vibrator under her white skirt.

SisK plug and play her anal with a purple vibrator under her white skirt.

XHamster 2 years ago

”big black dick tranny anal fucks white date”

”big black dick tranny anal fucks white date”

LesbianBliss 4 months ago

Educating A Bitchboy: Episode 4 "Last Chance"

Premium 46% HD 1:02:19

Educating A Bitchboy: Episode 4 "Last Chance"

Kink 15 years ago

Cute Asian Twink Femboy Estrogen Cumshot

66% HD 0:39 / 11:56

Cute Asian Twink Femboy Estrogen Cumshot

FapHouse 1 month ago

My First Cock with a Prince Albert

61% HD 0:39 / 10:56

My First Cock with a Prince Albert

FapHouse 1 month ago

An Honest Review: Cherry Keeper

61% HD 0:39 / 6:05

An Honest Review: Cherry Keeper

FapHouse 1 year ago

Pissing in an Inverted Chastity Cage Device with urethral sound

Pissing in an Inverted Chastity Cage Device with urethral sound

XHamster 3 years ago

Fucking Mtf Chastity Charlie 2

Fucking Mtf Chastity Charlie 2

XHamster 8 months ago

Caged boytoy gets Milked, Pegged and fed his own cum

66% HD 0:32 / 28:33

Caged boytoy gets Milked, Pegged and fed his own cum

Clips4sale 2 years ago

Submissive femboy is feminized and fucked

Submissive femboy is feminized and fucked

XHamster 1 year ago

Anal Sissygasms In The Woods Chastity Slut Jessica Bloom

Anal Sissygasms In The Woods Chastity Slut Jessica Bloom

XHamster 10 months ago

big dick trans girl shoots a big load after taking her chastity cage off - w0llip wollip

big dick trans girl shoots a big load after taking her chastity cage off - w0llip wollip

Itsrealamateurs 1 month ago

Femboy Sissy Strap-on Spitroast In Chastity Pegged By Sexy FemDom Duo By Mistress Mercer

Femboy Sissy Strap-on Spitroast In Chastity Pegged By Sexy FemDom Duo By Mistress Mercer

BeMyHole 2 months ago

Feeling sexy in hot nylon lingerie, frustrated in chastity ofcourse as we can't have it all can we...

Feeling sexy in hot nylon lingerie, frustrated in chastity ofcourse as we can't have it all can we...

FapHouse 1 year ago

My BF Was Late to Cum Fuck Me

61% HD 0:08 / 1:02

My BF Was Late to Cum Fuck Me

FapHouse 11 months ago

Sissy crossdresser struggles in heavy chain selfbondage

Sissy crossdresser struggles in heavy chain selfbondage

XHamster 3 months ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

Sophia Loreen Private Show

HD 2:00 / 25:41

Sophia Loreen Private Show

Camster 2 weeks ago

Sabrina Smiith Private Show

4K 2:00 / 12:17

Sabrina Smiith Private Show

Camster 4 months ago

My Ass is My Pussy

My Ass is My Pussy

XHamster 11 months ago

”T-girl is pissing over her prolapped booty”

”T-girl is pissing over her prolapped booty”

429Men 6 months ago

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

TransTube.tv 1 year ago

Nyxi Leon's Boihole Used in Chastity by Mistress Bailey Love

69% HD 1:01 / 22:10

Nyxi Leon's Boihole Used in Chastity by Mistress Bailey Love

FapHouse 2 years ago

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