Training Videos - Trans (93,000)

Sissy trainer - Give your ass

Sissy trainer - Give your ass

DeegX 3 years ago

Training Before New Year's Eve

Training Before New Year's Eve

xHamster 1 month 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

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

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

xHamster 4 years ago

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

66% HD 1:01 / 6:01

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

FapHouse 1 year ago

Petra in virgin white,s

Petra in virgin white,s

xHamster 2 months ago

Private Sex-tape

59% HD 1:01 / 11:43

Private Sex-tape

FapHouse 2 years 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

For Your Boy Pussy Ashley Sinclair

70% HD 1:01 / 5:13

For Your Boy Pussy Ashley Sinclair

FapHouse 1 month 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

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

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

Sasha's Morning Spitroast

Sasha's Morning Spitroast

xHamster 11 months ago

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

xHamster 7 months ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

Clips4sale 7 months ago

Training the 18 yrs boy slut from Iowa

Training the 18 yrs boy slut from Iowa

aShemaleTube 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

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

61% HD 1:01 / 6:49

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

FapHouse 3 months ago

Big ass goddess trains new sub

Big ass goddess trains new sub

aShemaleTube 3 years ago

Addiction to Cum

Addiction to Cum

xHamster 7 months ago

Submissive Asian Ladyboy Anal Casting & Slave Training

55% HD 1:01 / 39:45

Submissive Asian Ladyboy Anal Casting & Slave Training

FapHouse 7 months ago

Extra Large Cock Training

Extra Large Cock Training

Eporner 6 months ago

Sofia Ferreira Private Show

Sofia Ferreira Private Show

Flirt4Free 11 months 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

LEGAL lad attempt his assfuck to sqiurt and groaning for the very first time

LEGAL lad attempt his assfuck to sqiurt and groaning for the very first time

WebcamBros 7 months 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

Getting Ready with Sissy Maid Candy!

Getting Ready with Sissy Maid Candy!

xHamster 2 months ago

trans bitch with a meaty dick

trans bitch with a meaty dick

xHamster 3 months ago

The Last Virgin of 2025

66% 0:29 / 28:53

The Last Virgin of 2025

Clips4sale 4 months ago

Sissies are Made to be Servants

Sissies are Made to be Servants

ShemaleSin 8 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

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

Sophia Loreen Private Show

61% HD 2:00 / 12:52

Sophia Loreen Private Show

Flirt4Free 10 months ago

my idol best ever training

my idol best ever training

Tranny.one 4 years 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

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

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

GayDudesFucking 6 months ago

The flawless anal training - Part three

The flawless anal training - Part three

ShemaleSin 10 months ago

Lucas's Bi Slave Training

Lucas's Bi Slave Training

BeMyHole 2 years ago

Deep Sissy Fisting

Deep Sissy Fisting

FapHouse 1 year 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 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

Cum Dumpster Training

Cum Dumpster Training

aShemaleTube 1 year ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years 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

hot livi doll gets bbc trained

hot livi doll gets bbc trained

PornOne 2 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 3 weeks ago

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one 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

servant missy bound for new girl suckjob training

servant missy bound for new girl suckjob training

FetishShrine 1 week 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

Sissy Fuckdoll

xHamster 1 year ago

Finally all in with 15 inch King Cock dildo

Finally all in with 15 inch King Cock dildo

xHamster 7 months ago

Just because I can..

Just because I can..

xHamster 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

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

Sissy Hole Training

Sissy Hole Training

Xfeed 2 years ago

how to use a fufu pinch

how to use a fufu pinch

TrannyGem 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

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner 2 years 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

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

Carmen Cruz Trains A Lesson

Carmen Cruz Trains A Lesson

TrannyGem 5 years ago

sissy Cumslut Teaching

sissy Cumslut Teaching

TrannyGem 4 years 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

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube 6 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

Sissy BIG BLACK COCK Agonizing Rectal Instructing

Sissy BIG BLACK COCK Agonizing Rectal Instructing

TrannyGem 4 years ago

Between the Lines & Between My Legs

Between the Lines & Between My Legs

xHamster 7 months ago

Milk Your Transgirl EPISODE

Milk Your Transgirl EPISODE

ShemaleSin 4 years ago

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

BeMyHole 3 years ago

RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

xHamster 4 years ago

Living His Best Life as a Girl

Living His Best Life as a Girl

xHamster 10 months ago

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

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

ShemaleSin 10 months ago

Full Collection of Dildo Play

Full Collection of Dildo Play

xHamster 4 months ago

tutored By Big black cock

tutored By Big black cock

TransTube.tv 1 year ago

Bad Slut needs more Training

Bad Slut needs more Training

TrannyGem 7 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

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

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

TrannyGem 3 years ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Lesbian8 1 year ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

xHamster 1 year ago

Human Ashtray for Mistress Lilith

58% HD 1:01 / 41:36

Human Ashtray for Mistress Lilith

FapHouse 3 months ago

Brazilian Ladyboy Slave Training and Anal Casting

63% HD 1:01 / 32:58

Brazilian Ladyboy Slave Training and Anal Casting

FapHouse 6 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

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 11 months ago

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

66% HD 0:10 / 14:56

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

LoyalFans 1 week ago

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

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

MyTransfix 3 weeks ago

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

57% HD 0:10 / 11:40

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

LoyalFans 2 months ago

Pegging femboy with massive strapon!

Pegging femboy with massive strapon!

EpicGFs 2 years ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 8 months ago

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem 11 months 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

Femboy sissy training rides BBC dildo

Femboy sissy training rides BBC dildo

aShemaleTube 1 year 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

All that mouth training pays off : facefucking pretty transwife Melody

All that mouth training pays off : facefucking pretty transwife Melody

Amateur8 11 months ago

The Training Of - Olivia Robin

The Training Of - Olivia Robin

AbTranny 3 years ago

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

aShemaleTube 11 months ago

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Fapnado 3 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 3 weeks ago

Glamgurlxoxo: Sissy CD gives Wet BJ and Swallow Hot Cum Load from Young Guy

Glamgurlxoxo: Sissy CD gives Wet BJ and Swallow Hot Cum Load from Young Guy

TrannyGem 5 years 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

Sissy Anal Orgasm After College

Sissy Anal Orgasm After College

xHamster 4 months ago

21yo Femboy Viii penalized

21yo Femboy Viii penalized

TransTube.tv 11 months ago

ASMR Sissy Training For Panty Femboys JOI

ASMR Sissy Training For Panty Femboys JOI

Fapcat 3 years ago

Sissy puppet

TrannyGem 1 year ago

Training Sissy Throat and Pussy 3

Training Sissy Throat and Pussy 3

BoyFriendTV 9 months ago

Completely Submitted and Feminized

Completely Submitted and Feminized

xHamster 7 months ago

Sex Training

xHamster 3 months ago

Turned Into a Good Pet

Turned Into a Good Pet

xHamster 10 months 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

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

xHamster 7 months ago

Seduced By Silk - Star Nine

58% HD 0:10 / 13:41

Seduced By Silk - Star Nine

LoyalFans 2 years ago

Period training for sissy bitches by Domina Lady Julina

Period training for sissy bitches by Domina Lady Julina

Pornzona 4 weeks ago

anal-plug vibrates whilst chastity cage makes transgirl despairing

anal-plug vibrates whilst chastity cage makes transgirl despairing

Amateur8 1 month ago

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