Training Videos - Trans (27,387)

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

OMG !!! Joi Legend humiliation training 🔥

OMG !!! Joi Legend humiliation training 🔥

aShemaleTube 1 year ago

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

4Gay 6 days ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 1 year ago

What you looking for? A feminization Musical - Sissy Victoria

What you looking for? A feminization Musical - Sissy Victoria

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 6 days 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

Sissy Whore Training

Sissy Whore Training

xHamster 1 year ago

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

xHamster 11 months ago

G066 - Cum Swallow Compilation 2

56% 1:01 / 15:24

G066 - Cum Swallow Compilation 2

FapHouse 6 months ago

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

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

xHamster 6 months ago

sissy training for bimbo sluts

sissy training for bimbo sluts

aShemaleTube 3 years ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv 7 months ago

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

TrannyGem 3 years ago

The perfect anal training Part 3

The perfect anal training Part 3

W1mp 4 months ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 8 months ago

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one 3 years ago

Gag Slut Training

Gag Slut Training

BeMyHole 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

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

30 mins no break fellate spitroast contest!

30 mins no break fellate spitroast contest!

TrannyGem 2 months ago

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

xHamster 4 months ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 5 months ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

xHamster 1 year 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

Sissygasm Training 2

Sissygasm Training 2

xHamster 4 months ago

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

PornoXO 2 months ago

Claire Tenebrarum & Natalie Mars - Training

Claire Tenebrarum & Natalie Mars - Training

Eporner 3 years ago

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

aShemaleTube 2 months ago

Sissy Fuck Training

Sissy Fuck Training

aShemaleTube 3 years ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 4 months ago

I WANT YOU BABY!!

I WANT YOU BABY!!

xHamster 2 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 7 months ago

Sissys Breast Pumping Session Enlarging my boobs

Sissys Breast Pumping Session Enlarging my boobs

xHamster 2 weeks ago

Assfucking Pummeling Machine - Compil 15

Assfucking Pummeling Machine - Compil 15

TrannyGem 2 years ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 3 years ago

Whife *

TrannyGem 6 years ago

Goddess Rosie: Serve My Every Desire so Sweetly

Goddess Rosie: Serve My Every Desire so Sweetly

xHamster 1 month ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

Lesbian8 1 month 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

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Sissy training

Eporner 8 months ago

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 6 months ago

tutored By Big black cock

tutored By Big black cock

TransTube.tv 11 months ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 3 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

xHamster 2 months ago

2032 - the Bwno Future

56% 1:01 / 15:06

2032 - the Bwno Future

FapHouse 4 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

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

xHamster 2 months ago

Fuck Us Both Billy

Fuck Us Both Billy

xHamster 3 months ago

Gorgeous Puppygirl Nyxi Leon Trained & Fucked by Daddy Doggystyle and Reverse Cowgirl

Gorgeous Puppygirl Nyxi Leon Trained & Fucked by Daddy Doggystyle and Reverse Cowgirl

FapHouse 1 month ago

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole 6 months ago

Kendall Penny New Orleans Gay Training

Kendall Penny New Orleans Gay Training

BeMyHole 1 year ago

Living His Best Life as a Girl

68% 0:39 / 27:47

Living His Best Life as a Girl

FapHouse 6 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

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

aShemaleTube 6 months ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

Femboy sissy training rides BBC dildo

Femboy sissy training rides BBC dildo

aShemaleTube 1 year ago

Shemale Porn Video Lucas's Bi Slave Training

Shemale Porn Video Lucas's Bi Slave Training

Tranny.one 1 year ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

aShemaleTube 11 months ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube 7 years ago

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

77% HD 1:01 / 19:53

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

FapHouse 1 year ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years 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 10 months ago

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

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

FapHouse 1 year ago

Sasha's Morning Spitroast

Sasha's Morning Spitroast

xHamster 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

Sissy Cum Swallow Training

Sissy Cum Swallow Training

Tranny.one 3 years ago

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

55% HD 1:01 / 23:39

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

FapHouse 1 month ago

Training Sissy Throat and Pussy 3

Training Sissy Throat and Pussy 3

BoyFriendTV 4 months ago

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one 3 years ago

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube 3 years ago

Crossdressing Sissy Husband gets pegged & humiliated

Crossdressing Sissy Husband gets pegged & humiliated

xHamster 1 year ago

White Guy University Lesson two

White Guy University Lesson two

UiPorn 6 months ago

REAL TGIRLS: Cream Pie From The Space Guy (FULL)

REAL TGIRLS: Cream Pie From The Space Guy (FULL)

xHamster 2 years ago

BBC TRAINING WITH CERJOY

BBC TRAINING WITH CERJOY

xHamster 3 months ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

xHamster 1 year ago

His Personal Fucktoy

70% 1:01 / 23:00

His Personal Fucktoy

FapHouse 2 months ago

Horny Sissy Slut Training

Horny Sissy Slut Training

xHamster 4 years ago

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 7 months ago

PuppyGirl Itsol heads for a walk and gets pegged

PuppyGirl Itsol heads for a walk and gets pegged

Transvids.tv 6 months ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 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

Sissy Affirmations

Sissy Affirmations

ShemaleSin 2 months ago

New Girl in the Sissy Harem

New Girl in the Sissy Harem

xHamster 2 months ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 3 years ago

All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody

All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody

xHamster 9 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 2 years ago

Miniskirt Puppy

Miniskirt Puppy

GayCK 5 years ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 7 months ago

Feminization Sissification Sissy Threesome Training Blowjob

Feminization Sissification Sissy Threesome Training Blowjob

BeMyHole 1 year ago

TS Training

xHamster 1 year ago

Corporate Training - Episode 2

Corporate Training - Episode 2

xHamster 1 year ago

I Caught Stepdaddy Jerking Off in His Room – Oops!

I Caught Stepdaddy Jerking Off in His Room – Oops!

XXXShake 1 year ago

Kity Slave Training

Kity Slave Training

aShemaleTube 5 years ago

Cock Worship Boy Training

Cock Worship Boy Training

Eporner 1 year ago

Kimber Haven BBC Sissy Training

Kimber Haven BBC Sissy Training

aShemaleTube 4 years ago

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

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

Fapnado 2 years 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 4 months ago

Katie Fox Huge Anal Dildo Compilation

61% HD 1:01 / 1:15:07

Katie Fox Huge Anal Dildo Compilation

FapHouse 2 weeks ago

Trans Damsel takes Immense Trunk like a mega-cockslut.

Trans Damsel takes Immense Trunk like a mega-cockslut.

TransTube.tv 1 year ago

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube 2 years ago

dame-domineering Teaches Her shelady damsels

dame-domineering Teaches Her shelady damsels

TrannyGem 5 years ago

Training day 04 - 2023-02-21 - quite the fulfilled day

Training day 04 - 2023-02-21 - quite the fulfilled day

xHamster 2 years ago

Sissy Fuckdoll

xHamster 1 year ago

Sissy tarts take hormones and tear up

Sissy tarts take hormones and tear up

TrannyGem 3 years ago

Denim Girl

xHamster 7 months ago

Double Fuck for Sissy Hole

Double Fuck for Sissy Hole

xHamster 3 weeks ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Eporner 1 year ago

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

ShemaleSin 3 years ago

transgender princess Makes You Learn To Love BIG BLACK COCK

transgender princess Makes You Learn To Love BIG BLACK COCK

TrannyGem 2 years ago

Nylon whore Dagmar321 jerks off and squirts

Nylon whore Dagmar321 jerks off and squirts

xHamster 3 years ago

Mistress wants to dress you up like her fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress wants to dress you up like her fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 8 months ago

Sissy Slut Training 3

Sissy Slut Training 3

xHamster 9 months ago

Petra,s ninth training (incl double penetration and giant sex-toy)

Petra,s ninth training (incl double penetration and giant sex-toy)

ShemaleSin 5 months ago

Sissy trainer: become slut like her

Sissy trainer: become slut like her

xHamster 4 years ago

Bi Encouragement for secret sissy - FemDom

Bi Encouragement for secret sissy - FemDom

xHamster 2 months ago

Rah Teach

TrannyGem 4 years ago

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