Chastity Videos - Trans (71,146)

bang machine session XXL shlong

bang machine session XXL shlong

ShemaleSin 1 year ago

Cuckold, sph, degrading, hot wife!

Cuckold, sph, degrading, hot wife!

XHamster 9 months ago

JessieBbwSissy - Plapgasm Compilation

JessieBbwSissy - Plapgasm Compilation

XHamster 8 months ago

Lisa and t-girl Lucy anal training and chastity

Lisa and t-girl Lucy anal training and chastity

MatureTubeHere 4 years ago

Sissy Ruined Orgasm, Edging And Sounding Hard Cock - Chastity Punishment

Sissy Ruined Orgasm, Edging And Sounding Hard Cock - Chastity Punishment

XHamster 1 year ago

Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat

Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat

XHamster 10 months ago

MylaRose69's BBC POV Blowjob: A Blonde Trans Girl's Sweet Surrender

MylaRose69's BBC POV Blowjob: A Blonde Trans Girl's Sweet Surrender

BallsAndBoobs 2 months ago

caged sissy slut ride big dildo in public toilet jessie sissy adventures

caged sissy slut ride big dildo in public toilet jessie sissy adventures

XHamster 8 months ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

ThePornstar 1 year ago

WHAT FINER TIGHTS TO WEAR ON a SISSY BLACK SPEAR TRYST

WHAT FINER TIGHTS TO WEAR ON a SISSY BLACK SPEAR TRYST

TrannyGem 5 years ago

2025 Trans Anal & Cum Compilation Pt 1

4K 0:41 / 52:42

2025 Trans Anal & Cum Compilation Pt 1

Clips4sale 10 months ago

Sissy at Gloryhole Gets Rimmed by Stranger

Sissy at Gloryhole Gets Rimmed by Stranger

ShemaleSin 3 years ago

Variety Itsol gets her tight ass drilled by a massive BBC and takes a hot creampie

Variety Itsol gets her tight ass drilled by a massive BBC and takes a hot creampie

TrannyMovs 4 months ago

[720p] Femboy slave pegged by his mistress

[720p] Femboy slave pegged by his mistress

Clips4sale 1 month ago

Hot Sissy in Chastity Squirts

Hot Sissy in Chastity Squirts

AShemaleTube 9 years ago

Screwing Mtf Chastity Charlie

Screwing Mtf Chastity Charlie

ShemaleSin 5 months ago

Jessica Doll's Every single week Fuckmachine Therepy two

Jessica Doll's Every single week Fuckmachine Therepy two

ShemaleSin 2 months ago

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

55% HD 0:11 / 34:44

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

Clips4sale 4 years ago

Femdom bangs bimbo sissy cd doxy in booty w/ unicorn sex-toy in chastity makes femboy ride BBC part 2/5

Femdom bangs bimbo sissy cd doxy in booty w/ unicorn sex-toy in chastity makes femboy ride BBC part 2/5

ShemaleSin 3 years ago

Luna Rides a Biggest BBC Sex tool in Chastity

Luna Rides a Biggest BBC Sex tool in Chastity

ShemaleSin 7 months ago

OnlyForEmma - Emma's Sissy Chastity Orgasm - Hands-Free Cum Show

OnlyForEmma - Emma's Sissy Chastity Orgasm - Hands-Free Cum Show

BallsAndBoobs 2 months ago

My anal riding compilation

My anal riding compilation

XHamster 2 years ago

Sissy Crossdresser Lucy Torn Up by ten Inch Black BIG BLACK COCK whilst in Virginity at She-World Bang-Out Pub

Sissy Crossdresser Lucy Torn Up by ten Inch Black BIG BLACK COCK whilst in Virginity at She-World Bang-Out Pub

TrannyGem 5 years ago

Alexander Batista Private Show

58% HD 2:00 / 11:35

Alexander Batista Private Show

Flirt4Free 4 years ago

Sissy Maid Self Bondage frog tie with armbinder

Sissy Maid Self Bondage frog tie with armbinder

XHamster 5 years ago

SPH: me Tiny is Bigger than u Hard

SPH: me Tiny is Bigger than u Hard

ShemaleSin 5 years ago

Lanas Weekly Anal Invasion Lesson

Lanas Weekly Anal Invasion Lesson

TrannyGem 5 years ago

I SAID I WAS BACK TO FILMING... You all asked for it so much in the comments that I got Gabriel to give me a supreme suck off and I munched his taut rump unmerciful - read the flick comments.

I SAID I WAS BACK TO FILMING... You all asked for it so much in the comments that I got Gabriel to give me a supreme suck off and I munched his taut rump unmerciful - read the flick comments.

TrannyGem 3 months ago

HannaTransa Chastity Crossdresser outdoors at train station. 4

HannaTransa Chastity Crossdresser outdoors at train station. 4

GayCK 2 years ago

raven vice strap on top compilation

HD 0:20 / 32:18

raven vice strap on top compilation

PornBox 3 months ago

JOKER'S XXX ENJOYMENT: Dirty Makeup Bang With Tranny Harley ABRIDGED

JOKER'S XXX ENJOYMENT: Dirty Makeup Bang With Tranny Harley ABRIDGED

Lesbian8 8 months ago

Sissy locked in purity gets porked by her machine to satisfy her Parent

Sissy locked in purity gets porked by her machine to satisfy her Parent

TrannyGem 3 years 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 5 months ago

Trans Dance PMV

Trans Dance PMV

Tranny.one 2 years ago

Sissy CEI Suck your Panties Clean SLUT

52% HD 0:28 / 8:48

Sissy CEI Suck your Panties Clean SLUT

Clips4sale 2 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 4 years ago

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Xshemale 9 months ago

Hot TS Kitty Lucia Maya Drips Cum in Chastity Whilst Screwing Her Booty Then Unlocks Cage & Cums Hard

Hot TS Kitty Lucia Maya Drips Cum in Chastity Whilst Screwing Her Booty Then Unlocks Cage & Cums Hard

ShemaleSin 2 years ago

Chastity Fuckdolls Reverse Gangbang Kaela Luna Thea Daze Luci Belle Meddle Blooms Chastity Char

Chastity Fuckdolls Reverse Gangbang Kaela Luna Thea Daze Luci Belle Meddle Blooms Chastity Char

GetTranny 10 months ago

Crossdresser Astolfo can finnaly open his box after railing good-sized fucktoys for hours

Crossdresser Astolfo can finnaly open his box after railing good-sized fucktoys for hours

TrannyGem 3 years ago

No. 161: a Dildo in a Chastity Belt

No. 161: a Dildo in a Chastity Belt

XHamster 4 months ago

Rikki as Mickey Mouse Latex Suit, Foot Tickling Machine & Unique Tools Experiment

43% HD 0:39 / 25:53

Rikki as Mickey Mouse Latex Suit, Foot Tickling Machine & Unique Tools Experiment

FapHouse 5 months ago

Sophia Loreen Party on Aug 14, 2026 - Part 5

4K 2:00 / 49:16

Sophia Loreen Party on Aug 14, 2026 - Part 5

Camster 4 weeks ago

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

TrannyGem 4 years ago

How to Put on a Chastity Cage and Train Your Ass with a BBC

How to Put on a Chastity Cage and Train Your Ass with a BBC

XHamster 2 years ago

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up Sissification

43% HD 0:33 / 16:20

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up Sissification

Clips4sale 2 years ago

Sissy slut fucked in chastity cage cums hands free

Sissy slut fucked in chastity cage cums hands free

MenGem 4 years ago

Sissy wife put into chastity and diaper after self facial

Premium 4K 6:46

Sissy wife put into chastity and diaper after self facial

Clips4sale 1 month ago

Lesbian Anal Sissy Milking & Fisting Polieana And Jessica Bloom

Lesbian Anal Sissy Milking & Fisting Polieana And Jessica Bloom

XHamster 3 years ago

Slut Academy Pegging and Strap-on blowjob with TS girl - 4K | Demoness Luna, JuliaTS

63% 4K 0:30 / 17:46

Slut Academy Pegging and Strap-on blowjob with TS girl - 4K | Demoness Luna, JuliaTS

Clips4sale 10 months ago

Story of when daddy pimped me out. First week. Anal toy.

Story of when daddy pimped me out. First week. Anal toy.

XHamster 11 months ago

Abby Kitty's Chinese New Year Sissy Training: Cumshots & Edging

Abby Kitty's Chinese New Year Sissy Training: Cumshots & Edging

BallsAndBoobs 2 months ago

Breaking in the Bimbo (pt 2)

HD 0:13 / 22:33

Breaking in the Bimbo (pt 2)

IWantClips 2 months ago

Trans babe sucked by Asian femdom

Trans babe sucked by Asian femdom

Some.Porn 1 year ago

HotPinkNymph's first time with StarDust Dragon Amarok: Shaking, moaning, and getting a hot creampie

HotPinkNymph's first time with StarDust Dragon Amarok: Shaking, moaning, and getting a hot creampie

TrannyMovs 1 year ago

Riding some BBC ... well my sextoy at least

Riding some BBC ... well my sextoy at least

ShemaleSin 1 year ago

LOCKTOBER DAY 31 RELEASE DAY

LOCKTOBER DAY 31 RELEASE DAY

XHamster 1 year ago

Femization Lesson POV Femdom with Madame Juliette

53% 0:12 / 10:04

Femization Lesson POV Femdom with Madame Juliette

Clips4sale 3 years ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 1 day ago

”GROOBYGIRLS - Nuzzle’s Fetishes”

”GROOBYGIRLS - Nuzzle’s Fetishes”

ThePornstar 4 months ago

Total Sissy Amnesia

Total Sissy Amnesia

ShemaleSin 10 months ago

Step-mommy's yoga class sissy WMV

46% HD 0:24 / 7:10

Step-mommy's yoga class sissy WMV

Clips4sale 1 year ago

Tiny Sissy Fucked by Daddy Dong King Part 2

Tiny Sissy Fucked by Daddy Dong King Part 2

FapHouse 4 months ago

Chastity cage and bang machine makes flawless cum

Chastity cage and bang machine makes flawless cum

ShemaleSin 8 months ago

T-girl plays with her flexible balls and cock in pole solo - Chastity Belt

T-girl plays with her flexible balls and cock in pole solo - Chastity Belt

AnySex 1 year ago

Fucking Machine Sissy Anal Orgasm And Cum Play

Fucking Machine Sissy Anal Orgasm And Cum Play

XHamster 1 year ago

SPH IR domina fucked in front of man with cock cage

SPH IR domina fucked in front of man with cock cage

Some.Porn 2 years ago

Trans Angel Rides Sex tool in Chastity

Trans Angel Rides Sex tool in Chastity

FreePorn8 6 months ago

Lime sissygasms whilst riding on horsecock

Lime sissygasms whilst riding on horsecock

ShemaleSin 6 months ago

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

TrannyGem 1 year ago

Wholesome Twosome

Wholesome Twosome

ShemaleSin 1 year ago

Sissy Foot Fetish Job Interview Episode - Footjob And Oral-sex Training Chastity Doxy Jessica Bloom

Sissy Foot Fetish Job Interview Episode - Footjob And Oral-sex Training Chastity Doxy Jessica Bloom

ShemaleSin 1 year ago

Double Female-dominator Wheelbarrow Fisting

Double Female-dominator Wheelbarrow Fisting

SortPorn 2 months ago

wrecked sissy's ejaculation after pussyjob

wrecked sissy's ejaculation after pussyjob

TrannyGem 2 years ago

Goddess Allegra and fuck machine take turns on Trans Girl August Harper

65% 0:11 / 7:23

Goddess Allegra and fuck machine take turns on Trans Girl August Harper

Clips4sale 2 years ago

Tall and sexy gf

Tall and sexy gf

XHamster 1 year ago

rubber slave in chastity being fucked by fucking machine

rubber slave in chastity being fucked by fucking machine

XHamster 7 months ago

Goth Princess Whore Tiffany Minx - Male Voice Over Story Slow Motion Blow Job

Goth Princess Whore Tiffany Minx - Male Voice Over Story Slow Motion Blow Job

AShemaleTube 1 year ago

Sissy Public Humiliation Assignment Sissy Maid buys a gulp

Sissy Public Humiliation Assignment Sissy Maid buys a gulp

ShemaleSin 2 years ago

Sissy Candy's Dildo Post Compilation!

Sissy Candy's Dildo Post Compilation!

XHamster 1 year ago

So hot cumming after 7 days in chastity and anal training

So hot cumming after 7 days in chastity and anal training

XHamster 2 years ago

Sissy Rides Strapon After Sissygasm Part 2

Sissy Rides Strapon After Sissygasm Part 2

XHamster 1 week ago

Erica's Punishment Paddling

Erica's Punishment Paddling

Clips4sale 3 years ago

Chastity Rex Word Een Sissy

58% HD 0:39 / 5:32

Chastity Rex Word Een Sissy

FapHouse 7 months ago

Lily Starlet Takes knuckle and ass inside-out for highly very first time!

Lily Starlet Takes knuckle and ass inside-out for highly very first time!

TrannyGem 3 years ago

Lana Trap gets Assfucking Teaching from Bombi for her 1 Month in Innocence Cell Part 1

Lana Trap gets Assfucking Teaching from Bombi for her 1 Month in Innocence Cell Part 1

TrannyGem 5 years ago

las barras de chocolate son ufff delicious

las barras de chocolate son ufff delicious

PornBox 1 year ago

Nun Dildo Dommed & Spanked By Priest ABRIDGED

Nun Dildo Dommed & Spanked By Priest ABRIDGED

XHamster 2 years ago

Feelipe & Adara Private Show

59% HD 2:00 / 5:01

Feelipe & Adara Private Show

Flirt4Free 1 year ago

My sissy caresses on my alpha masculine shoulders while he boinks me in purity

My sissy caresses on my alpha masculine shoulders while he boinks me in purity

TrannyGem 10 months ago

Huge Bad Dragon Opportunity for Sissy Ass-Fuck Biotch Xxx Pegging with Strap Dildo by female domination Domme Mercer

Huge Bad Dragon Opportunity for Sissy Ass-Fuck Biotch Xxx Pegging with Strap Dildo by female domination Domme Mercer

TrannyGem 10 months ago

Sissy Fucked by BBC Locked in Chastity Cage

Sissy Fucked by BBC Locked in Chastity Cage

Eporner 1 year ago

Permanent chastity belt

Permanent chastity belt

XHamster 3 years ago

Encaged sissy caught in public

Encaged sissy caught in public

GayCK 3 years ago

Training Like a Good Gurl

Training Like a Good Gurl

XHamster 6 months ago

Hot Trans Bailey Wilde Removes Chastity Then Jerks Off

Hot Trans Bailey Wilde Removes Chastity Then Jerks Off

Dafreeporn 1 month ago

Nailing my booty dressed in my purity box

Nailing my booty dressed in my purity box

TrannyGem 1 year ago

tslut: Bully ts CHEERLEADERS in heat

tslut: Bully ts CHEERLEADERS in heat

Clips4sale 1 year ago

Humiliation for Crossdresser stepson is found by Step Mom Charlie Monaco!

65% 0:13 / 9:40

Humiliation for Crossdresser stepson is found by Step Mom Charlie Monaco!

Clips4sale 1 year ago

Guzzle Your Jizz Sissy! CEI Encouragement Compilation - Jessica Bloom

Guzzle Your Jizz Sissy! CEI Encouragement Compilation - Jessica Bloom

MyTransfix 4 months ago

I'm Disabled Zoe Jarvis 39 Transgender Climax MtF Chastity cage

I'm Disabled Zoe Jarvis 39 Transgender Climax MtF Chastity cage

Amateur8 2 months ago

Femboy Love

HentaiGem 1 year ago

Jenny Wei Reamed and Creampied

Jenny Wei Reamed and Creampied

AShemaleTube 3 years ago

Femboy in v-card box gets knotted by Enormous Bad Dragon Bishop on his poke machine.

Femboy in v-card box gets knotted by Enormous Bad Dragon Bishop on his poke machine.

Gay4Porn 1 year ago

Roommate Loses Bet and Gets Locked in Chastity Clip 1

Roommate Loses Bet and Gets Locked in Chastity Clip 1

XHamster 5 months ago

Sissygasm with BBC dildo in pink dress

Sissygasm with BBC dildo in pink dress

XHamster 11 months ago

Meddle Blooms - Chastity Fuckdolls - Kaela Luna, Chastity Charli And Luci Belle

Meddle Blooms - Chastity Fuckdolls - Kaela Luna, Chastity Charli And Luci Belle

PePorn 9 months 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

Mike Swift & David Golden Private Show

60% HD 2:00 / 5:46

Mike Swift & David Golden Private Show

Flirt4Free 1 month ago

Natalie Stone - Locked in Chastity

Natalie Stone - Locked in Chastity

IcePorn 2 years ago

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

68% HD 1:01 / 39:28

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

FapHouse 7 months ago

sissy transsexual chastity poppertrainer

sissy transsexual chastity poppertrainer

ShemaleSin 5 years ago

Full vid -Biggest Horse dong Sissygasm

Full vid -Biggest Horse dong Sissygasm

ShemaleSin 1 year ago

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

68% HD 0:30 / 17:28

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

Clips4sale 1 year ago

Cutest Femboy in Chastity Spreads Legs to Be Fucked Hard

Cutest Femboy in Chastity Spreads Legs to Be Fucked Hard

MyLust 1 year ago

”T-girl is pissing over her prolapped booty”

”T-girl is pissing over her prolapped booty”

429Men 8 months ago

Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll

Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll

XHamster 7 months ago

Patric & Alexander & Lian Private Show

57% HD 2:00 / 38:07

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Squeeze Out the Last Cum

59% HD 1:01 / 11:50

Squeeze Out the Last Cum

FapHouse 2 months ago

Lisa and tranny Lucy anal training and chastity

Lisa and tranny Lucy anal training and chastity

ShemaleSin 4 years ago

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