Training Videos - Trans (27,963)

SISSYGASM WITH STEPMOMMY by Phoenix Studio

SISSYGASM WITH STEPMOMMY by Phoenix Studio

ShemaleSin 1 week 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

Ryu Nymph Stretches her Arse with a Monster can

Ryu Nymph Stretches her Arse with a Monster can

TrannyGem 4 years ago

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 7 months ago

how to use a fufu pinch

how to use a fufu pinch

TrannyGem 2 years ago

Corporate Training - Episode 2

Corporate Training - Episode 2

xHamster 1 year ago

Girls playing before going out

Girls playing before going out

xHamster 1 year ago

Furry trap slave training

Furry trap slave training

aShemaleTube 6 years ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

Would Your Parents Be Proud?

Would Your Parents Be Proud?

xHamster 8 months ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner 2 years ago

tutored By Big black cock

tutored By Big black cock

TransTube.tv 11 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 Cum Swallow Training

Sissy Cum Swallow Training

Tranny.one 3 years ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 9 months ago

OMG !!! Joi Legend humiliation training 🔥

OMG !!! Joi Legend humiliation training 🔥

aShemaleTube 1 year ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

Lesbian8 2 months ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 3 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 1 month ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

SortPorn 2 weeks ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 1 year ago

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

xHamster 3 months ago

Sissy Fuck Training

Sissy Fuck Training

aShemaleTube 3 years ago

get on your knees sissy

get on your knees sissy

Transvids.tv 6 months ago

Training Cum Eating

Training Cum Eating

aShemaleTube 1 year ago

”Teaching Teen How to Suck”

”Teaching Teen How to Suck”

TransHero 1 month 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

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube 2 months ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Sissy Dreams - 3 (eng)

Sissy Dreams - 3 (eng)

XXXShemalePorn 11 years ago

Living His Best Life as a Girl

Living His Best Life as a Girl

xHamster 6 months ago

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one 3 years ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 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

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 5 months ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year 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

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 instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 8 months ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

Horny Sissy Slut Training

Horny Sissy Slut Training

xHamster 4 years ago

Sissy Hope streaming online and showing how she trains her pussy boy for anal fun

Sissy Hope streaming online and showing how she trains her pussy boy for anal fun

xHamster 3 years ago

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

67% HD 1:01 / 25:41

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

FapHouse 1 year 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

Dee Williams' lustful doodling and kissing after panty tease

Dee Williams' lustful doodling and kissing after panty tease

UrGayPorn 4 months ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

xHamster 1 month ago

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube 3 years ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 4 months ago

the gift - futa femboy pt 2

the gift - futa femboy pt 2

HentaiGem 3 years ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years ago

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem 8 months ago

2032 - the Bwno Future

53% 1:01 / 15:06

2032 - the Bwno Future

FapHouse 5 months ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TrannyGem 5 years ago

femboy chastity dildo riding!!

femboy chastity dildo riding!!

xHamster 1 year ago

Experienced Shemale Trains A Chap

Experienced Shemale Trains A Chap

aShemaleTube 14 years ago

2 sissy latex nurses getting pegged in Chastity by MILF Lisa

2 sissy latex nurses getting pegged in Chastity by MILF Lisa

xHamster 2 years ago

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

Tranny.one 4 years ago

Submissive Asian Ladyboy Anal Casting & Slave Training

53% HD 1:01 / 39:45

Submissive Asian Ladyboy Anal Casting & Slave Training

FapHouse 3 months ago

Shemale Porn Video Lucas's Bi Slave Training

Shemale Porn Video Lucas's Bi Slave Training

Tranny.one 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 10 months ago

Brazilian tgirl slut training💋💘

Brazilian tgirl slut training💋💘

aShemaleTube 1 year 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 3 months ago

Sissy training

Eporner 9 months ago

Fag Teaching

Transvids.tv 4 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

Gorgeous tgirl Angel dildo training 💋

Gorgeous tgirl Angel dildo training 💋

aShemaleTube 1 year ago

At Her Mercy: Hot Trans Domme Trains You

At Her Mercy: Hot Trans Domme Trains You

xHamster 9 months ago

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one 3 years ago

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube 2 years ago

Sissy trainer: become slut like her

Sissy trainer: become slut like her

xHamster 4 years ago

My Neighbor Fisting My Ass

My Neighbor Fisting My Ass

xHamster 4 months ago

Petra's porno marathon part 1-3

Petra's porno marathon part 1-3

xHamster 8 months ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

xHamster 3 months ago

Like a Virgin, Anal Training

Like a Virgin, Anal Training

xHamster 4 weeks ago

Hole Training

Eporner 1 year ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 6 months ago

How to make a Lovely Servant Sissy 8: Grad Asst. Teaching another Sissy

How to make a Lovely Servant Sissy 8: Grad Asst. Teaching another Sissy

TrannyGem 5 years ago

tutored By Big black cock

tutored By Big black cock

Transvids.tv 11 months ago

2 transsexual sissy bitch training here throat

2 transsexual sissy bitch training here throat

Amateur8 1 month ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Sissy Whore Training

Sissy Whore Training

xHamster 1 year ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 3 years ago

Sissy Trained And Owned By Big Bull With Black Bull, Sasha Desade And Black Penis

Sissy Trained And Owned By Big Bull With Black Bull, Sasha Desade And Black Penis

PePorn 4 months ago

Training myself for real Cocks

Training myself for real Cocks

2BGay 8 months ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv 8 months ago

Natalie Mars In Training The Little-gimp#2

Natalie Mars In Training The Little-gimp#2

AbTranny 2 years ago

Crossdresser gets machine fucked with XXL Monster Dildos #4

Crossdresser gets machine fucked with XXL Monster Dildos #4

xHamster 1 year 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

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem 7 months ago

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

xHamster 10 months 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

Gag Slut Training

Gag Slut Training

BeMyHole 3 years ago

GONZO - Senso Unico Peccati Trans Italiani

GONZO - Senso Unico Peccati Trans Italiani

TrannyGem 5 years ago

my idol best ever training

my idol best ever training

Tranny.one 3 years ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 5 months ago

Fucked by Old Man Behind the Scenes

61% 1:01 / 28:00

Fucked by Old Man Behind the Scenes

FapHouse 1 year 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

Sissy in Office

Sissy in Office

xHamster 2 months ago

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

52% HD 1:01 / 9:38

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

FapHouse 1 year ago

Femboy Assfucking Spreading With A Phat Node Fake penis

Femboy Assfucking Spreading With A Phat Node Fake penis

4Gay 1 month ago

Threesome Caged Sucker Gets His Ass Destroyed and Swallows My Cum

Threesome Caged Sucker Gets His Ass Destroyed and Swallows My Cum

xHamster 7 months ago

Whife *

TrannyGem 6 years ago

Sissy Training

xHamster 2 years ago

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

TrannyGem 4 years ago

I am a Sissy

TrannyGem 5 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

Non stop PEGGING gives me 7x ANAL ORGASM, I rewarded with 1 for her SISSY dick

Non stop PEGGING gives me 7x ANAL ORGASM, I rewarded with 1 for her SISSY dick

xHamster 1 year ago

Fisting Double Sissygasm Cumshots

Fisting Double Sissygasm Cumshots

xHamster 6 months ago

Cock Worship Boy Training

Cock Worship Boy Training

Eporner 1 year ago

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube 7 years ago

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

aShemaleTube 5 years 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

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

xHamster 6 months ago

Kendall Penny New Orleans Gay Training

Kendall Penny New Orleans Gay Training

BeMyHole 1 year 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

Lexi Teaches Her Sub

Lexi Teaches Her Sub

TrannyGem 5 years 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

sissy training for bimbo sluts

sissy training for bimbo sluts

aShemaleTube 3 years ago

Young goth femboy anal training 🍆💋

Young goth femboy anal training 🍆💋

aShemaleTube 1 year ago

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