Chastity Videos - Trans (50,661)

My Trans Step-sister Destroyed My Ass in Black Fishnet - Rough Lycra Creampie

HD 0:39 / 16:18

My Trans Step-sister Destroyed My Ass in Black Fishnet - Rough Lycra Creampie

FapHouse 4 days ago

Consequences for Breaking Out of Chastity

61% HD 1:01 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 1 week ago

Brides Hands-free BBC Cumshots

65% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 2 weeks ago

Caged Trans Rachael Belle Takes BBC with Joy

78% 1:01 / 29:01

Caged Trans Rachael Belle Takes BBC with Joy

FapHouse 1 year ago

Disappointed Sissy plugged and in chastity

Disappointed Sissy plugged and in chastity

ShemaleSin 1 week ago

Itty Bitty Sissy Breeding

Itty Bitty Sissy Breeding

Eporner 1 week ago

Bend Over Anal Pound in Chastity Lock!

58% 1:01 / 7:22

Bend Over Anal Pound in Chastity Lock!

FapHouse 1 month ago

Sissy Slut Fucked Raw Then Swallows Huge Creampie and Her Own Sissygasm

Sissy Slut Fucked Raw Then Swallows Huge Creampie and Her Own Sissygasm

xHamster 1 week ago

Size Queen Christina Sapphire Wants Creampie for Cucky Hubby to Lick up

52% HD 1:01 / 30:34

Size Queen Christina Sapphire Wants Creampie for Cucky Hubby to Lick up

FapHouse 1 month ago

howling delight

HD 0:30 / 43:14

howling delight

PornBox 1 week ago

Anal Hotty - Gaping TS Gray Perrier's Taut Butt with AJ's biggest rod

Anal Hotty - Gaping TS Gray Perrier's Taut Butt with AJ's biggest rod

ShemaleSin 3 months ago

Blonde Bimbo Sissy Rides Dildo Like a Good Little Slut

Blonde Bimbo Sissy Rides Dildo Like a Good Little Slut

xHamster 1 week ago

Trans girls look the best with chastity on and BBC up her ass

Trans girls look the best with chastity on and BBC up her ass

Eporner 2 weeks ago

howling delight

64% HD 0:30 / 43:14

howling delight

AnalVids 1 week ago

Turning My Boyfriend Into A Sissy

Turning My Boyfriend Into A Sissy

xHamster 6 days ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

getTranny 1 week ago

Emo Femboy gets bred by BIG BLACK DICK

Emo Femboy gets bred by BIG BLACK DICK

MyTransfix 1 week ago

BBC Vs. Tgirl In Chastity

BBC Vs. Tgirl In Chastity

aShemaleTube 6 months ago

Russian Sissy in a Chastity Cage Cums

Russian Sissy in a Chastity Cage Cums

xHamster 2 weeks ago

Submissive slut writhes in torment as crossdresser pounds his in chastity cage

Submissive slut writhes in torment as crossdresser pounds his in chastity cage

GayVD 4 days ago

Learn how to properly milk your submissive hottie in kinky latex & strapon play

Learn how to properly milk your submissive hottie in kinky latex & strapon play

GayVD 2 weeks ago

SISSY T-GIRL IN CHASTITY GETS ASS FUCKED

SISSY T-GIRL IN CHASTITY GETS ASS FUCKED

Eporner 2 weeks ago

Chastity Cutie

Eporner 5 months ago

AB081 Sensitive Unstoppable squirting - Thick faux penis (Asian and English subtitles)

AB081 Sensitive Unstoppable squirting - Thick faux penis (Asian and English subtitles)

MyTransfix 6 days ago

Brides Hands-free BBC Cumshots

65% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 2 weeks ago

TS Bruna Rides Dildo In Chastity Lock

TS Bruna Rides Dildo In Chastity Lock

Nuvid 4 months ago

I lost my chastity in my bum with my bf, I had never done it before - Luana Prado

I lost my chastity in my bum with my bf, I had never done it before - Luana Prado

TrannyGem 5 days ago

Rachael Belle Justice

Rachael Belle Justice

aShemaleTube 11 months ago

Sissy Spreads Her Hole

Sissy Spreads Her Hole

xHamster 1 month ago

I shag my roomy and packs my fuck hole total of jizz in purity

I shag my roomy and packs my fuck hole total of jizz in purity

Gayhub 2 months ago

Locked in chastity and BBC fucking

Locked in chastity and BBC fucking

Eporner 3 weeks ago

Cum Eating Chastity Slave

Cum Eating Chastity Slave

Eporner 6 months ago

Gwen Rides and Cums

Gwen Rides and Cums

xHamster 9 months ago

Trans Chastity Princess Takes BBC

Trans Chastity Princess Takes BBC

aShemaleTube 1 month ago

Violet Chastity Teaser

Violet Chastity Teaser

AbTranny 2 weeks ago

HOTTEST Crossdresser Bailey Wilde in Chastity Banged Reverse Cowgirl

HOTTEST Crossdresser Bailey Wilde in Chastity Banged Reverse Cowgirl

Tranny.one 7 months ago

divergence studios - goddess tangent natalie mars training the little gimp porn video

divergence studios - goddess tangent natalie mars training the little gimp porn video

TransDoe 1 week ago

Femboy In Chastity Gets His Hole Rammed By His Stud Lover

Femboy In Chastity Gets His Hole Rammed By His Stud Lover

Eporner 2 years ago

BTG goes Wet, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Pee Drink, Creampie, Cum in Mouth BTG117

Premium 1:02:43

BTG goes Wet, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Pee Drink, Creampie, Cum in Mouth BTG117

XVideosRed 2 years ago

Two Sissies Share A BBC

Two Sissies Share A BBC

Eporner 1 week ago

Chastity Fuckdoll Reverse Gangbang

Chastity Fuckdoll Reverse Gangbang

Eporner 8 months ago

Pink Sissy

aShemaleTube 3 years ago

Chastity Princess

Chastity Princess

Eporner 1 month ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

xHamster 2 weeks ago

Putting Restraints on Ginger-haired Trans Doll

Putting Restraints on Ginger-haired Trans Doll

TrannyGem 1 week ago

Chastity Fuckdoll

Chastity Fuckdoll

aShemaleTube 3 months ago

Sissy crossdresser cumming twice and swallowing her own cum

Sissy crossdresser cumming twice and swallowing her own cum

xHamster 3 days ago

Rubbing my inverted cage cock like a pussy clit and cumming 4 times

Rubbing my inverted cage cock like a pussy clit and cumming 4 times

xHamster 3 years ago

Trans Chastity Beauties Tease With Toys

Trans Chastity Beauties Tease With Toys

xHamster 9 months ago

Chastity Breeding PMV2

Chastity Breeding PMV2

Eporner 1 week ago

Cute CD in chastity 3

Cute CD in chastity 3

Eporner 6 years ago

EXCLUSIVE B-DAY SEQUENCE HAVING ROMP WITH MY BF - FINISH ON CRIMSON - LUANA PRADO

EXCLUSIVE B-DAY SEQUENCE HAVING ROMP WITH MY BF - FINISH ON CRIMSON - LUANA PRADO

TrannyGem 4 weeks ago

Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll

Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll

xHamster 7 months ago

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

HD 0:23 / 41:59

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

AnalVids 1 week ago

Axel Reigns _TS-Bride-Spitroasted-amp-Creampied.mov

Axel Reigns _TS-Bride-Spitroasted-amp-Creampied.mov

aShemaleTube 1 year ago

Sissy Kenzie Star Hands-free cumming in my lil pink cage

Sissy Kenzie Star Hands-free cumming in my lil pink cage

aShemaleTube 3 days ago

Taskmaster Sissy Screws Chastity Femboy

Taskmaster Sissy Screws Chastity Femboy

ShemaleSin 5 days ago

Cumpilation: Chastity Sissygasms, Ruined Orgasms, & Crossdressing Cumshots Of A Desperate Sissy

Cumpilation: Chastity Sissygasms, Ruined Orgasms, & Crossdressing Cumshots Of A Desperate Sissy

AbTranny 1 week ago

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onlyfans - variety itsol rodrigo amor how many times would you smash porn video

TransDoe 1 year ago

Extreme Orgasm

70% HD 1:01 / 9:23

FapHouse 2 weeks ago

Femdom owns Sissies

Femdom owns Sissies

Eporner 10 months ago

Sissy Pussy - PMV by PrimeBBC

Sissy Pussy - PMV by PrimeBBC

aShemaleTube 1 year ago

Sissy crossdresser cowgirl ride

Sissy crossdresser cowgirl ride

FreePorn8 3 days ago

Sissy Slut School Lesson 2 of 4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

Premium HD 14:56

Sissy Slut School Lesson 2 of 4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

Clips4sale 1 week ago

FELLOW TO HOMO SISSY CONCLUDE PROCESS AND GUIDE

FELLOW TO HOMO SISSY CONCLUDE PROCESS AND GUIDE

GayCK 3 months ago

A Forbidden Night: A Hot Party With Trans & Crossdressers

A Forbidden Night: A Hot Party With Trans & Crossdressers

getTranny 1 week ago

best pegging moments

best pegging moments

Pornzona 1 week ago

Sissy Nyxi Leon bashed In Virginity

Sissy Nyxi Leon bashed In Virginity

TransTube.tv 10 months ago

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pure-ts - sophia calypso bigger dick tops porn video

TransDoe 1 year ago

Total Sissy Amnesia

Total Sissy Amnesia

xHamster 6 months ago

The Vice Mach 2 chastity cage (prototype) product review!!

The Vice Mach 2 chastity cage (prototype) product review!!

xHamster 6 months ago

nikola ophan sissy in chastity slut worships bbc facefuck anal facial

nikola ophan sissy in chastity slut worships bbc facefuck anal facial

PornOne 1 year ago

two slim brunette trans ladies have a good time on webcam

two slim brunette trans ladies have a good time on webcam

aShemaleTube 4 years ago

Intens caught in public

Intens caught in public

Pornzona 2 weeks ago

Sissy Nipples in Training

Sissy Nipples in Training

xHamster 7 months ago

Transgirl Fucktoy Is A True QOS And BBC Only

Transgirl Fucktoy Is A True QOS And BBC Only

Eporner 1 month ago

Put on her heels and started riding her much loved sex tool

Put on her heels and started riding her much loved sex tool

Lesbian8 4 days ago

Femboy Screwing Compilation

Femboy Screwing Compilation

ShemaleSin 3 months ago

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TransDoe 1 year ago

Ava Sexy Anal Play Time

Ava Sexy Anal Play Time

aShemaleTube 3 weeks ago

Pretty Femboy in Chastity Fucked Raw

Pretty Femboy in Chastity Fucked Raw

aShemaleTube 1 week ago

Flat Chastity Sissy

Flat Chastity Sissy

xHamster 1 year ago

Sissy in chastity fucked by different people

Sissy in chastity fucked by different people

xHamster 3 years ago

Crossdresser Puts Red-haired Trans Doll in Restrain bondage DOMINATION & SUBMISSION

Crossdresser Puts Red-haired Trans Doll in Restrain bondage DOMINATION & SUBMISSION

TrannyGem 3 days ago

Stiletto Sissy Slaves First Anal Stretching With Electrics And Chastity By Mistress Mercer

Stiletto Sissy Slaves First Anal Stretching With Electrics And Chastity By Mistress Mercer

AbTranny 1 week ago

sissy in chastity gets fucked by bbc creampie

sissy in chastity gets fucked by bbc creampie

PornOne 1 year ago

BBC Roomie Wrecks Chastity Hole Cum Flood Gush

BBC Roomie Wrecks Chastity Hole Cum Flood Gush

GayPornWatch 2 months ago

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onlyfans - bambifyme mreasydeck which asset you wanna play with first porn video

TransDoe 1 year ago

Bbc9

aShemaleTube 1 year ago

Elf Femboy In Chastity Belt Gets Tight Ass Stretched By Bbc Cock And Fuck Machine Until Cum

Elf Femboy In Chastity Belt Gets Tight Ass Stretched By Bbc Cock And Fuck Machine Until Cum

AbTranny 4 weeks ago

the chastity maid interview

the chastity maid interview

PornOne 9 months ago

Step-Sister Saskia Bangs my Sissy Holes with Mistresse Murmur - this was so embarrassing, but I loved it

Step-Sister Saskia Bangs my Sissy Holes with Mistresse Murmur - this was so embarrassing, but I loved it

ShemaleSin 2 weeks ago

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onlyfans - bella joie and tsslayer transgirl in penis pump

TransDoe 2 years ago

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PornOne 2 years ago

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

xHamster 2 months ago

Getting Tall Heels so Step-Daddy can fuck me better

Getting Tall Heels so Step-Daddy can fuck me better

Juicexxx 1 week ago

FEMOUT - The Return of Chastity Charli

FEMOUT - The Return of Chastity Charli

Fapnado 3 days ago

10 Cumshots Compilation, Chastity With Anal Orgasm

10 Cumshots Compilation, Chastity With Anal Orgasm

AbTranny 5 days ago

Sissy maid locked in urethral cock cage training with XL horse cock

Sissy maid locked in urethral cock cage training with XL horse cock

JuicyTrans 1 week ago

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aShemaleTube 1 year ago

Reneenicolecd - update #12 - Fat chief and bj trans fucky-fucky female - May 28, 2026

Reneenicolecd - update #12 - Fat chief and bj trans fucky-fucky female - May 28, 2026

TrannyGem 3 days ago

Little Asian Sissy In Chastity Using Her Big Black Toy

Little Asian Sissy In Chastity Using Her Big Black Toy

Eporner 2 weeks ago

Chastity Fuckdoll (1080).mp4

Chastity Fuckdoll (1080).mp4

aShemaleTube 3 months ago

Wollip Tastes Her Own Cum as She Cums Into a Glass and Drinks It All After Riding a Dildo an

Wollip Tastes Her Own Cum as She Cums Into a Glass and Drinks It All After Riding a Dildo an

aShemaleTube 2 weeks ago

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aShemaleTube 1 year ago

Cute Chastity Sissy In Holographic Skirt Fucks Herself With A Dildo

Cute Chastity Sissy In Holographic Skirt Fucks Herself With A Dildo

AbTranny 4 days ago

TS Istol Fucked BBC

TS Istol Fucked BBC

aShemaleTube 7 months ago

The sissy story of Autumn Brie

The sissy story of Autumn Brie

aShemaleTube 5 months ago

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TransDoe 9 months ago

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TransDoe 3 months ago

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

FreePorn8 2 months ago

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Chained my sissy bussy to the fucking machine while gooning

xHamster 3 months ago

Sissy latexdoll chokes on big cock while masturbating in rubber trainin

Sissy latexdoll chokes on big cock while masturbating in rubber trainin

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The Naughty Blonde Trap Removes Chastity And Cums

The Naughty Blonde Trap Removes Chastity And Cums

ShemaleSex 5 months ago

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RedHead cums caged

ShemaleSin 1 year ago

Transgender sissy joyce in chastity shows hormone progress

Transgender sissy joyce in chastity shows hormone progress

xHamster 11 months ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 9 months ago

Trans Teen Chastity Anal Threesome

Trans Teen Chastity Anal Threesome

AbTranny 3 days ago

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TransDoe 4 months ago

Ash-blonde Sissy Breezy Fellates Hefty Fuck stick

Ash-blonde Sissy Breezy Fellates Hefty Fuck stick

Gayhub 2 weeks ago

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