Training (94,077)

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

76% 1:01 / 6:20

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

FapHouse Hace3 mes

Private Sex-tape

61% HD 1:01 / 11:43

Private Sex-tape

FapHouse Hace 2 yaño

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

68% HD 0:39 / 7:36

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

FapHouse Hace3 mes

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem Hace 6 yaño

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one Hace 4 yaño

Stepdaddy's princess does what she is told

64% HD 1:01 / 25:50

Stepdaddy's princess does what she is told

FapHouse Hace 3 yaño

Hey Everyone, if You Love Mtof Transformation & Training the Miracle of Transforming Our Femboys or Sissybois Into Stunning Girl

79% HD 1:01 / 5:34

Hey Everyone, if You Love Mtof Transformation & Training the Miracle of Transforming Our Femboys or Sissybois Into Stunning Girl

FapHouse Hace 1 yaño

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one Hace 4 yaño

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

aShemaleTube Hace 5 yaño

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole Hace 3 yaño

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

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Training the 18 yrs boy slut from Iowa

Training the 18 yrs boy slut from Iowa

aShemaleTube Hace 4 yaño

Feminization Training - Show This To Your Wife

Feminization Training - Show This To Your Wife

xHamster Hace 1 yaño

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

xHamster Hace 1 yaño

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem Hace 1 yaño

Sissy Circuit Training

75% HD 1:01 / 15:40

Sissy Circuit Training

FapHouse Hace 1 yaño

Sasha's Morning Spitroast

Sasha's Morning Spitroast

xHamster Hace11 mes

Tranny Training

Tranny Training

Eporner Hace 1 yaño

Sissy training

Eporner Hace 1 yaño

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 Hace 1 yaño

Human Ashtray for Mistress Lilith

58% HD 1:01 / 41:36

Human Ashtray for Mistress Lilith

FapHouse Hace3 mes

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole Hace11 mes

2032 - the Bwno Future

2032 - the Bwno Future

xHamster Hace9 mes

Nyxi Leon teaches another sissy how to handle a big cock like a pro

Nyxi Leon teaches another sissy how to handle a big cock like a pro

TrannyMovs Hace1 mes

Femdom Sissy Chastity Tease

Femdom Sissy Chastity Tease

xHamster Hace1 mes

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem Hace 4 yaño

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

xHamster Hace 2 yaño

Michelly Makes It Hard

76% HD 0:39 / 9:07

Michelly Makes It Hard

FapHouse Hace1 mes

Sissy Slave Training

Sissy Slave Training

BeMyHole Hace 5 yaño

Extra Large Cock Training

Extra Large Cock Training

Eporner Hace6 mes

Sissy Training

xHamster Hace 1 yaño

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

xHamster Hace9 mes

Sissy Training by Queen Daralis Part 2

54% HD 1:01 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse Hace4 mes

Sissy Slut Training

Sissy Slut Training

xHamster Hace 1 yaño

Sissy Whore Training

Sissy Whore Training

xHamster Hace 1 yaño

Cum eating trainer video for the greedy sissy faggot whores

Cum eating trainer video for the greedy sissy faggot whores

Tranny.one Hace 3 yaño

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner Hace 2 yaño

I Dare You to Resist: Stay Gay or Become My Filthiest Cum-Slut Faggot

64% HD 0:30 / 39:31

I Dare You to Resist: Stay Gay or Become My Filthiest Cum-Slut Faggot

Clips4sale Hace4 mes

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn Hace 1 yaño

Sissy BIG BLACK COCK Agonizing Rectal Instructing

Sissy BIG BLACK COCK Agonizing Rectal Instructing

TrannyGem Hace 4 yaño

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin Hace 4 yaño

Arousing petite teacher Riu Mukai trains her students' petite asian and tranny while blowing and fucking her students' big c

Arousing petite teacher Riu Mukai trains her students' petite asian and tranny while blowing and fucking her students' big c

TrannyMovs Hace6 mes

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 Hace 1 yaño

Sissy's tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

Sissy's tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

xHamster Hace 1 yaño

my idol best ever training

my idol best ever training

Tranny.one Hace 4 yaño

Sissy Fuckdoll

xHamster Hace 1 yaño

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one Hace 2 yaño

Whife *

TrannyGem Hace 6 yaño

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 Hace3 mes

Petra's final exam (incl piss drinking, fisting and more)

Petra's final exam (incl piss drinking, fisting and more)

xHamster Hace11 mes

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one Hace 4 yaño

Russian sissy training camp

Russian sissy training camp

Eporner Hace 1 yaño

how to use a fufu pinch

how to use a fufu pinch

TrannyGem Hace 2 yaño

Anal Training Compilation

Anal Training Compilation

BeMyHole Hace 3 yaño

Petra in virgin white,s

Petra in virgin white,s

xHamster Hace2 mes

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one Hace 4 yaño

Kegel Orgasm Training

Kegel Orgasm Training

BeMyHole Hace 3 yaño

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 Hace 2 semana

Sissy Conversion Therapy - Part 1

HD 1:01 / 10:59

Sissy Conversion Therapy - Part 1

FapHouse Hace9 mes

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

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

AbTranny Hace 4 semana

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

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

getTranny Hace 3 yaño

Sissies are Made to be Servants

Sissies are Made to be Servants

ShemaleSin Hace8 mes

sissy Cumslut Teaching

sissy Cumslut Teaching

TrannyGem Hace 4 yaño

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 Hace 3 yaño

Sissy Fuckdoll 2

Sissy Fuckdoll 2

xHamster Hace6 mes

Providing a Break From the Grind

Providing a Break From the Grind

xHamster Hace 1 semana

Femboy instructing part 1: The Back Bend

Femboy instructing part 1: The Back Bend

Gay4Porn Hace 2 yaño

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 Hace 2 yaño

Fag Instructing 8

Fag Instructing 8

TransTube.tv Hace9 mes

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv Hace 1 yaño

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv Hace 1 yaño

sluttami

ShemaleSin Hace 5 yaño

Spectacular steamy T.I.L.F training toyboy

Spectacular steamy T.I.L.F training toyboy

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crossdresser anal training

crossdresser anal training

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RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

xHamster Hace 4 yaño

Inhale My Femboy's Dick (with Lina Lux)

Inhale My Femboy's Dick (with Lina Lux)

TrannyGem Hace6 mes

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

TrannyGem Hace 4 yaño

wet bitch femboy loves light BDSM and cum with pleasure ( sissy training )

wet bitch femboy loves light BDSM and cum with pleasure ( sissy training )

Itsrealamateurs Hace 6 día

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

ShemaleSin Hace 1 yaño

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube Hace 4 yaño

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

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mistress training kinky sissy bitch

mistress training kinky sissy bitch

Itsrealamateurs Hace 6 día

2 Mommies Training a Slut LUCY HART PENNY BARBER MIRA M

2 Mommies Training a Slut LUCY HART PENNY BARBER MIRA M

FetishShrine Hace5 mes

Big ass Latina gets facial after anal fuck - Amateur Porn

Big ass Latina gets facial after anal fuck - Amateur Porn

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Transsexual training - bukkake gokkun! Shemale anal fuck orgy

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

xHamster Hace 1 yaño

BBC TRAINING WITH CERJOY

BBC TRAINING WITH CERJOY

xHamster Hace8 mes

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

xHamster Hace7 mes

Cuckold Training Part 2

Cuckold Training Part 2

3DPornDude Hace10 mes

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

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

ShemaleSin Hace11 mes

Addiction to Cum

Addiction to Cum

xHamster Hace7 mes

Shemale Pussy Denial

68% HD 0:20 / 13:02

Shemale Pussy Denial

IWantClips Hace 1 yaño

Big Ass Trans Raven Anal Creampie and Fucked Doggystyle by Inflatable Dildo

Big Ass Trans Raven Anal Creampie and Fucked Doggystyle by Inflatable Dildo

xHamster Hace 2 semana

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one Hace 4 yaño

It’s Just Curiosity, Right? Confused? Not Anymore

53% 0:38 / 14:00

It’s Just Curiosity, Right? Confused? Not Anymore

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The Last Virgin of 2025

66% 0:29 / 28:53

The Last Virgin of 2025

Clips4sale Hace4 mes

Trannies in training - (Episode #08)

Trannies in training - (Episode #08)

xHamster Hace2 mes

Dirty Tranny Extra Large Cock Training

Dirty Tranny Extra Large Cock Training

BeMyHole Hace1 mes

Good Girl Training: Transfemme Anal JOI

45% HD 1:01 / 17:10

Good Girl Training: Transfemme Anal JOI

FapHouse Hace2 mes

Sissy Anal Orgasm After College

Sissy Anal Orgasm After College

xHamster Hace4 mes

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 Hace2 mes

Living His Best Life as a Girl

Living His Best Life as a Girl

xHamster Hace10 mes

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 Hace 3 yaño

Worship Superior Foreskin

Worship Superior Foreskin

xHamster Hace5 mes

feminisation training

feminisation training

xHamster Hace5 mes

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube Hace 7 yaño

”TS Jade Venus & Lexi Lore mouth & snatch training session”

”TS Jade Venus & Lexi Lore mouth & snatch training session”

LesbianBliss Hace3 mes

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

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

Tranny.one Hace 2 yaño

Shemale Slave Torn Open by Anal - Trained for Pain

Shemale Slave Torn Open by Anal - Trained for Pain

JpMilfs Hace 2 yaño

TRANNY Girls First Asshole Training Before Her Lover Shows Up

TRANNY Girls First Asshole Training Before Her Lover Shows Up

Eporner Hace2 mes

Long Sissy Training With Anal Dick Riding

Long Sissy Training With Anal Dick Riding

AbTranny Hace 4 semana

Corporate Training 2 (Rikolo

Corporate Training 2 (Rikolo

Eporner Hace5 mes

If he does these 5 things it says a lot about him

If he does these 5 things it says a lot about him

xHamster Hace4 mes

Your sissy maid

Your sissy maid

TrannyGem Hace 2 yaño

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

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

aShemaleTube Hace6 mes

Jobless Man Resorts to Feminization to Get Hired

Jobless Man Resorts to Feminization to Get Hired

xHamster Hace 1 semana

Natalie Mars Training the baby Gimp two

Natalie Mars Training the baby Gimp two

ShemaleSin Hace 5 yaño

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 Hace 1 yaño

You're Just a Drooling Faggot Slut – Worship My Cock

66% HD 0:30 / 42:55

You're Just a Drooling Faggot Slut – Worship My Cock

Clips4sale Hace3 mes

Kymmy Harper goes wild for cum and cock in hot threesome action

Kymmy Harper goes wild for cum and cock in hot threesome action

TrannyMovs Hace8 mes

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

BeMyHole Hace11 mes

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