Training Videos - Trans (85,646)

SISSYGASM WITH STEPMOMMY by Phoenix Studio

SISSYGASM WITH STEPMOMMY by Phoenix Studio

ShemaleSin 3 days ago

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

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

aShemaleTube 1 month ago

Training Cum Eating

Training Cum Eating

aShemaleTube 1 year ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube 2 months ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 8 months 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 10 months ago

Ryu Nymph Stretches her Arse with a Monster can

Ryu Nymph Stretches her Arse with a Monster can

TrannyGem 4 years ago

Sissy Cum Swallow Training

Sissy Cum Swallow Training

Tranny.one 3 years ago

”Teaching Teen How to Suck”

”Teaching Teen How to Suck”

TransHero 1 month ago

Cum eating trainer video for the greedy sissy faggot whores

Cum eating trainer video for the greedy sissy faggot whores

Tranny.one 3 years ago

get on your knees sissy

get on your knees sissy

Transvids.tv 6 months ago

how to use a fufu pinch

how to use a fufu pinch

TrannyGem 2 years ago

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 7 months ago

Sissy training

Eporner 9 months ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

SortPorn 2 weeks ago

OMG !!! Joi Legend humiliation training 🔥

OMG !!! Joi Legend humiliation training 🔥

aShemaleTube 1 year ago

G066 - Cum Swallow Compilation 2

57% 1:01 / 15:24

G066 - Cum Swallow Compilation 2

FapHouse 7 months ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 8 months ago

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

xHamster 2 months ago

Corporate Training - Episode 2

Corporate Training - Episode 2

xHamster 1 year ago

Furry trap slave training

Furry trap slave training

aShemaleTube 6 years ago

Fisting Double Sissygasm Cumshots

Fisting Double Sissygasm Cumshots

xHamster 5 months ago

Slutty Tranny Emily Adaire Is Fisted & DPed Anally in IR Gangbang 4K

Slutty Tranny Emily Adaire Is Fisted & DPed Anally in IR Gangbang 4K

AnySex 11 months ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

Lesbian8 2 months ago

Would Your Parents Be Proud?

Would Your Parents Be Proud?

xHamster 8 months ago

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin 3 years ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 3 years ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

xHamster 1 year ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

SortPorn 1 month ago

tutored By Big black cock

tutored By Big black cock

TransTube.tv 11 months ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 3 years ago

Sissygasm Training 2

Sissygasm Training 2

xHamster 5 months ago

Sissy Dreams - 3 (eng)

Sissy Dreams - 3 (eng)

XXXShemalePorn 10 years ago

All that mouth training pays off : facefucking marvelous transwife Melody

All that mouth training pays off : facefucking marvelous transwife Melody

ShemaleSin 1 year ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 1 year ago

Sissy Fuck Training

Sissy Fuck Training

aShemaleTube 3 years ago

Mature Mistress teaches two sissies how to be good cocksuckers

Mature Mistress teaches two sissies how to be good cocksuckers

Tranny.one 8 years ago

30 mins no break fellate spitroast contest!

30 mins no break fellate spitroast contest!

TrannyGem 3 months ago

What you looking for? A feminization Musical - Sissy Victoria

What you looking for? A feminization Musical - Sissy Victoria

xHamster 2 years ago

Sissy Whore Training

Sissy Whore Training

xHamster 1 year ago

Living His Best Life as a Girl

Living His Best Life as a Girl

xHamster 6 months ago

I masturbated and came in public in the car after the training

I masturbated and came in public in the car after the training

xHamster 2 years ago

Trans Anal Training Cumming Twice From Monster Sex-toy Hard And Caged

Trans Anal Training Cumming Twice From Monster Sex-toy Hard And Caged

ShemaleSin 3 weeks ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner 2 years ago

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

59% HD 0:10 / 31:04

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

LoyalFans 5 months ago

Ella Hollywood (Training Arc)

Ella Hollywood (Training Arc)

aShemaleTube 3 months ago

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

xHamster 2 years ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

SAY “I AM A FAGGOT MISTRESS RAVEN”

66% HD 0:10 / 23:45

SAY “I AM A FAGGOT MISTRESS RAVEN”

LoyalFans 3 years ago

Sissy blows a load inwards undies

Sissy blows a load inwards undies

TrannyGem 2 months ago

2032 - the Bwno Future

55% 1:01 / 15:06

2032 - the Bwno Future

FapHouse 4 months ago

Sissy Hot Anal Butt Plug Stretch Session

Sissy Hot Anal Butt Plug Stretch Session

xHamster 1 month ago

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube 3 years ago

Sissy training 5

Sissy training 5

xHamster 10 months ago

Sissy Training

xHamster 2 years ago

Gorgeous tgirl Angel dildo training 💋

Gorgeous tgirl Angel dildo training 💋

aShemaleTube 1 year ago

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one 3 years ago

Training myself for real Cocks

Training myself for real Cocks

2BGay 8 months ago

Sissy Stories Ep 3: Feminized by My Wife

63% HD 1:01 / 16:27

Sissy Stories Ep 3: Feminized by My Wife

FapHouse 11 months ago

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

Tranny.one 4 years ago

Ts Isabella sissy passions for his English Mistress

62% HD 1:01 / 24:03

Ts Isabella sissy passions for his English Mistress

FapHouse 3 years ago

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one 3 years ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 5 months ago

Claire Tenebrarum & Natalie Mars - Training

Claire Tenebrarum & Natalie Mars - Training

Eporner 3 years ago

Crossdresser gets machine fucked with XXL Monster Dildos #4

Crossdresser gets machine fucked with XXL Monster Dildos #4

xHamster 1 year ago

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

78% HD 1:01 / 19:53

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

FapHouse 1 year ago

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem 8 months ago

Is this an ass-fuck toy or a traffic cone? Emily Adaire's ass-fuck-bootcamp - day 8

Is this an ass-fuck toy or a traffic cone? Emily Adaire's ass-fuck-bootcamp - day 8

TransTube.tv 1 year ago

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

49% HD 1:01 / 9:38

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

FapHouse 1 year ago

I am a Sissy

TrannyGem 5 years ago

TS Anna Katt Prepares Lily's Ass for Cock

TS Anna Katt Prepares Lily's Ass for Cock

TrannyGem 6 years ago

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem 7 months ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years ago

Cum Dumpster Training

Cum Dumpster Training

aShemaleTube 11 months ago

Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage

Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage

xHamster 4 months 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

Tranny.one 3 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

Horny Sissy Slut Training

Horny Sissy Slut Training

xHamster 4 years ago

Dee Williams' lustful doodling and kissing after panty tease

Dee Williams' lustful doodling and kissing after panty tease

UrGayPorn 4 months ago

White Guy University Lesson two

White Guy University Lesson two

UiPorn 6 months ago

the gift - futa femboy pt 2

the gift - futa femboy pt 2

HentaiGem 3 years ago

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

aShemaleTube 8 months ago

Trans Damsel takes Immense Trunk like a mega-cockslut.

Trans Damsel takes Immense Trunk like a mega-cockslut.

TransTube.tv 1 year ago

Turning My Husband Into Transgirl superslut, Nymph first-ever time with Transgender Princess

Turning My Husband Into Transgirl superslut, Nymph first-ever time with Transgender Princess

TrannyGem 1 year ago

STROKE FOR DICK FAGGOT

56% HD 0:10 / 8:55

STROKE FOR DICK FAGGOT

LoyalFans 2 years ago

Living His Best Life as a Girl

68% 0:39 / 27:47

Living His Best Life as a Girl

FapHouse 6 months ago

How far can I inflate this spandex fuck stick? Emily Adaire's ass fucking-bootcamp - day 7

How far can I inflate this spandex fuck stick? Emily Adaire's ass fucking-bootcamp - day 7

TrannyGem 3 years ago

Diminutive Top Trans Goth Woman Pulverizes Male Masturbator Fucky-fucky Plaything Till Yam-sized Pop-shot and Ahegao Eye Spin

Diminutive Top Trans Goth Woman Pulverizes Male Masturbator Fucky-fucky Plaything Till Yam-sized Pop-shot and Ahegao Eye Spin

TransTube.tv 1 year ago

Submissive Asian Ladyboy Anal Casting & Slave Training

54% HD 1:01 / 39:45

Submissive Asian Ladyboy Anal Casting & Slave Training

FapHouse 3 months ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

xHamster 3 months ago

Natalie Mars In Training The Little-gimp#2

Natalie Mars In Training The Little-gimp#2

AbTranny 2 years ago

Femboy Assfucking Spreading With A Phat Node Fake penis

Femboy Assfucking Spreading With A Phat Node Fake penis

4Gay 1 month ago

PuppyGirl Itsol heads for a walk and gets pegged

PuppyGirl Itsol heads for a walk and gets pegged

Transvids.tv 7 months ago

Chatty crossdresser tries out new depth - 2023-02-23 - part 1 - known territory

Chatty crossdresser tries out new depth - 2023-02-23 - part 1 - known territory

xHamster 2 years ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Sissification and Rope Bondage for Nosey Stepbrother

58% HD 1:01 / 27:02

Sissification and Rope Bondage for Nosey Stepbrother

FapHouse 1 year ago

Hot Trans Girl Fucked in Every Room of the House by TS Babe - Hot Trans Lesbian Sex

Hot Trans Girl Fucked in Every Room of the House by TS Babe - Hot Trans Lesbian Sex

xHamster 4 months ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

Girls playing before going out

Girls playing before going out

xHamster 1 year ago

Caged Sissy Begs for Release � Magic Wand Tease Until She Cums Hard

Caged Sissy Begs for Release � Magic Wand Tease Until She Cums Hard

XXXXCum 5 months ago

Whife *

TrannyGem 6 years ago

BONDAGE & DISCIPLINE Sissy blow training with enema!

BONDAGE & DISCIPLINE Sissy blow training with enema!

Transvids.tv 1 year ago

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

xHamster 9 months ago

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TrannyGem 5 years ago

Brazilian tgirl slut training💋💘

Brazilian tgirl slut training💋💘

aShemaleTube 1 year ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

xHamster 3 weeks ago

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

TransTube.tv 8 months ago

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

aShemaleTube 5 years ago

Young goth femboy anal training 🍆💋

Young goth femboy anal training 🍆💋

aShemaleTube 1 year ago

Experienced Shemale Trains A Chap

Experienced Shemale Trains A Chap

aShemaleTube 14 years ago

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube 7 years ago

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube 2 years ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 5 months ago

Mom Domina Wakes Her Sissy Step-Stepson (Preview)

Mom Domina Wakes Her Sissy Step-Stepson (Preview)

Transvids.tv 6 months ago

2 transsexual sissy bitch training here throat

2 transsexual sissy bitch training here throat

Amateur8 1 month ago

Natalie Mars Training the baby Gimp 1

Natalie Mars Training the baby Gimp 1

ShemaleSin 4 years ago

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

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

xHamster 7 months ago

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