Training Videos - Trans (92,885)

Living His Best Life as a Girl

64% 0:39 / 27:47

Living His Best Life as a Girl

FapHouse 10 months ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube 6 months ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

63% HD 0:39 / 31:09

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

FapHouse 1 month ago

G066 - Cum Swallow Compilation 2

60% 1:01 / 15:24

G066 - Cum Swallow Compilation 2

FapHouse 11 months ago

Angel Reina Hanno Stimulates Cream with Golden Butt Plug

HD 0:39 / 27:31

Angel Reina Hanno Stimulates Cream with Golden Butt Plug

FapHouse 5 months ago

Claire Tenebrarum & Natalie Mars - Training

Claire Tenebrarum & Natalie Mars - Training

Eporner 3 years ago

Sophia Loreen Private Show

61% HD 2:00 / 12:52

Sophia Loreen Private Show

Flirt4Free 10 months ago

The Legend of Gerudo: Zelda Futanari Training [Futa, NTR, Threesome, Romance, Mind Destruction] [Public]

The Legend of Gerudo: Zelda Futanari Training [Futa, NTR, Threesome, Romance, Mind Destruction] [Public]

Eporner 1 year ago

Day 9 of Sissy Training - Makeup Melts Your Masculinity

52% HD 1:01 / 21:08

Day 9 of Sissy Training - Makeup Melts Your Masculinity

FapHouse 4 months ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 3 years ago

Petra in virgin white,s

Petra in virgin white,s

xHamster 2 months ago

Look My Skirt in Jean's on a Parking Lot in the Forest of Sénart. Vanessabitchx Parischiennetrvprod

63% HD 0:39 / 6:59

Look My Skirt in Jean's on a Parking Lot in the Forest of Sénart. Vanessabitchx Parischiennetrvprod

FapHouse 1 month ago

Jerk off Whilst I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

Jerk off Whilst I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

ShemaleSin 2 years ago

High Class Sissy Training

High Class Sissy Training

AbTranny 4 years ago

The English Mansion - Mistress Sophia - Secret Sissy Boyfriend Pt2 - Complete Movie

The English Mansion - Mistress Sophia - Secret Sissy Boyfriend Pt2 - Complete Movie

Tranny.one 2 years ago

Ultimate Sissy Fuck Doll Trainer

Ultimate Sissy Fuck Doll Trainer

xHamster 2 months ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 9 months ago

Anal Alien Eggs Insemination Femdom

60% HD 1:01 / 10:55

Anal Alien Eggs Insemination Femdom

FapHouse 1 week ago

Gym Tips for Sluts Feminization Motivation

65% HD 1:01 / 11:57

Gym Tips for Sluts Feminization Motivation

FapHouse 8 months ago

Deep Sissy Fisting

Deep Sissy Fisting

FapHouse 1 year ago

Getting Ready with Sissy Maid Candy!

Getting Ready with Sissy Maid Candy!

xHamster 2 months ago

hot livi doll gets bbc trained

hot livi doll gets bbc trained

PornOne 2 years ago

Nyxi Leon: Sissy Bunny Strips to Tease in Hot Anal Masturbation

64% HD 1:01 / 6:01

Nyxi Leon: Sissy Bunny Strips to Tease in Hot Anal Masturbation

FapHouse 1 year ago

Submissive Asian Ladyboy Anal Casting & Slave Training

54% HD 1:01 / 39:45

Submissive Asian Ladyboy Anal Casting & Slave Training

FapHouse 7 months ago

Private Sex-tape

59% HD 1:01 / 11:43

Private Sex-tape

FapHouse 2 years ago

Addiction to Cum

Addiction to Cum

xHamster 7 months ago

Shemale Training Her Sissy Friend.. Who May Become One Of Them

Shemale Training Her Sissy Friend.. Who May Become One Of Them

getTranny 3 years ago

Shemale and sex slave celebrates Chinese New Year with anal toying and blowjob

Shemale and sex slave celebrates Chinese New Year with anal toying and blowjob

XGroovy 3 years ago

Sissy Fuckdoll

xHamster 1 year ago

The Last Virgin of 2025

66% 0:29 / 28:53

The Last Virgin of 2025

Clips4sale 4 months ago

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one 4 years ago

sissy Cumslut Teaching

sissy Cumslut Teaching

TrannyGem 4 years ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

xHamster 1 year ago

Beauties of Anal Delights for the Female Superiority Society (part 2).

Beauties of Anal Delights for the Female Superiority Society (part 2).

xHamster 1 year ago

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

xHamster 1 month ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner 2 years ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

this babemale Ariel trains guy Mmm

this babemale Ariel trains guy Mmm

TrannyGem 6 years ago

Latex Sissy Tutored By Chastity Fuckmachine Drubbing Cocksucking Pegging by Mistresse Mercer

Latex Sissy Tutored By Chastity Fuckmachine Drubbing Cocksucking Pegging by Mistresse Mercer

ShemaleSin 4 years ago

SISSY TRAINING - Sasha de Sade and Mistress Murmur

SISSY TRAINING - Sasha de Sade and Mistress Murmur

AbTranny 6 years ago

Luna Completes Entire Anal Training Faproulette And Destroys Her Hole!! [full]

Luna Completes Entire Anal Training Faproulette And Destroys Her Hole!! [full]

AbTranny 2 weeks ago

Training the 18 yrs boy slut from Iowa

Training the 18 yrs boy slut from Iowa

aShemaleTube 4 years ago

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

aShemaleTube 11 months ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 1 year ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

2 Mommies Training a Slut LUCY HART PENNY BARBER MIRA M

2 Mommies Training a Slut LUCY HART PENNY BARBER MIRA M

FetishShrine 4 months ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

70% HD 1:01 / 10:12

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

FapHouse 1 year ago

trans bitch with a meaty dick

trans bitch with a meaty dick

xHamster 3 months ago

tutored By Big black cock

tutored By Big black cock

TransTube.tv 1 year ago

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

74% HD 0:39 / 27:11

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

FapHouse 6 months ago

Skinny trans girl with pig tails has butt sex in locker room

Skinny trans girl with pig tails has butt sex in locker room

xHamster 2 months ago

Wreck in my cock-squeezing lil' nail-fuckhole!!

Wreck in my cock-squeezing lil' nail-fuckhole!!

GayDudesFucking 6 months ago

Foolish Sissy Feminization Captions

Foolish Sissy Feminization Captions

TrannyGem 6 months ago

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one 4 years ago

Sissy Training

xHamster 1 year ago

Sissy Victim's Very First Bad Dragon Spreading Sesh with E-stim Encouragement by Domme Mercer

Sissy Victim's Very First Bad Dragon Spreading Sesh with E-stim Encouragement by Domme Mercer

TrannyGem 3 years ago

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

TrannyGem 3 years ago

Just because I can..

Just because I can..

xHamster 2 years ago

Can Barely Stand Anymore... My Legs Are Still Shaking After That

75% 1:01 / 6:20

Can Barely Stand Anymore... My Legs Are Still Shaking After That

FapHouse 2 months ago

Shemale training her sissy friend.. who may become one of them /// BeautizOnCam.com

Shemale training her sissy friend.. who may become one of them /// BeautizOnCam.com

Tranny.one 3 years ago

Big ass goddess trains new sub

Big ass goddess trains new sub

aShemaleTube 3 years ago

The flawless anal training - Part three

The flawless anal training - Part three

ShemaleSin 10 months ago

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Pornzona 1 month ago

Brazilian Ladyboy Slave Training and Anal Casting

58% HD 1:01 / 32:58

Brazilian Ladyboy Slave Training and Anal Casting

FapHouse 6 months ago

servant missy bound for new girl suckjob training

servant missy bound for new girl suckjob training

FetishShrine 5 days ago

Sissy Hole Training

Sissy Hole Training

Xfeed 2 years 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

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

TransTube.tv 1 year ago

Human Ashtray for Mistress Lilith

58% HD 1:01 / 41:36

Human Ashtray for Mistress Lilith

FapHouse 3 months ago

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

BeMyHole 5 years ago

BBC goes deep in sexy transsexual babe Kasey Kei in doggy pose

BBC goes deep in sexy transsexual babe Kasey Kei in doggy pose

Tranny.one 2 years ago

Trans Female trains you to deep-throat dinky, beginning soft but then predominant you and humping your face

Trans Female trains you to deep-throat dinky, beginning soft but then predominant you and humping your face

TransTube.tv 1 year ago

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

BeMyHole 2 years ago

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

TrannyGem 4 years ago

You Are My Sissy Whore and Will You Out!

57% 1:01 / 6:50

You Are My Sissy Whore and Will You Out!

FapHouse 1 year ago

my idol best ever training

my idol best ever training

Tranny.one 4 years ago

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem 11 months ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

xHamster 6 months ago

Lucas's Bi Slave Training

Lucas's Bi Slave Training

BeMyHole 2 years ago

Between the Lines & Between My Legs

Between the Lines & Between My Legs

xHamster 7 months ago

two Dommes and their trans floozy! Drubbing, FemDom, Humiliation

two Dommes and their trans floozy! Drubbing, FemDom, Humiliation

ShemaleSin 10 months ago

RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

xHamster 4 years ago

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

TrannyGem 3 years ago

2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven

2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven

xHamster 11 months ago

Jessica's Anal Training Series Episode 5

Jessica's Anal Training Series Episode 5

xHamster 2 weeks ago

Sissy Cumslut Training - Teaching You How to Suck and Swallow

56% HD 1:01 / 14:46

Sissy Cumslut Training - Teaching You How to Suck and Swallow

FapHouse 1 year ago

Slutty Sissy gets hard training Blowjob and Fuck Rough

Slutty Sissy gets hard training Blowjob and Fuck Rough

aShemaleTube 4 months ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

72% HD 0:39 / 13:39

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

FapHouse 1 year ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 8 months ago

Sissification feminization sissy instructing - Sissy spouse story (english voice)

Sissification feminization sissy instructing - Sissy spouse story (english voice)

TransTube.tv 1 year 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

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

xHamster 1 year ago

Sissy Slut Training 3

Sissy Slut Training 3

xHamster 1 year ago

Cum Dumpster Training

Cum Dumpster Training

aShemaleTube 1 year ago

Bad Slut needs more Training

Bad Slut needs more Training

TrannyGem 7 years ago

Finally all in with 15 inch King Cock dildo

Finally all in with 15 inch King Cock dildo

xHamster 6 months ago

how to use a fufu pinch

how to use a fufu pinch

TrannyGem 2 years ago

Krissy’s Sissy Ass Destroyed Belly Bulging Super Long Dildo Gush

Krissy’s Sissy Ass Destroyed Belly Bulging Super Long Dildo Gush

JuicyTrans 2 weeks ago

Full Collection of Dildo Play

Full Collection of Dildo Play

xHamster 3 months ago

Femboy sissy training rides BBC dildo

Femboy sissy training rides BBC dildo

aShemaleTube 1 year ago

Sissy puppet

TrannyGem 1 year ago

Female domination Mistress fucks bitch sissy butt, dual jizz assfuck orgasm

Female domination Mistress fucks bitch sissy butt, dual jizz assfuck orgasm

MyTransfix 2 weeks ago

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

TransHero 5 months ago

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 11 months ago

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

ShemaleSin 3 years ago

Sissy Silly Step-Sister Raunchy Drill and Gargle

Sissy Silly Step-Sister Raunchy Drill and Gargle

TrannyGem 5 years ago

Lady Lads gone nasty for jizz and meatpipe

Lady Lads gone nasty for jizz and meatpipe

Transvids.tv 10 months ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

xHamster 1 month ago

Sissy BIG BLACK COCK Agonizing Rectal Instructing

Sissy BIG BLACK COCK Agonizing Rectal Instructing

TrannyGem 4 years ago

Pegging femboy with massive strapon!

Pegging femboy with massive strapon!

EpicGFs 2 years ago

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

TrannyGem 4 years ago

Milk Your Transgirl EPISODE

Milk Your Transgirl EPISODE

ShemaleSin 4 years ago

All that mouth training pays off : facefucking pretty transwife Melody

All that mouth training pays off : facefucking pretty transwife Melody

Amateur8 11 months ago

Level up to Kaella

Level up to Kaella

TrannyGem 7 months ago

Charlotte Sins, Jade Venus, Zariah Aura, Victoria Grant Lesbian In Training

Charlotte Sins, Jade Venus, Zariah Aura, Victoria Grant Lesbian In Training

aShemaleTube 5 months ago

lucas bi training

lucas bi training

PornOne 2 years ago

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

TransTube.tv 1 year ago

Carmen Cruz Trains A Lesson

Carmen Cruz Trains A Lesson

TrannyGem 5 years ago

The Training Of - Olivia Robin

The Training Of - Olivia Robin

AbTranny 3 years ago

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