Training Videos - Trans (123,960)

Transsexual Slaves 3 Mistress Vida Trains a Submissive

Transsexual Slaves 3 Mistress Vida Trains a Submissive

XHamster 1 week ago

Sissygasm Training 2

Sissygasm Training 2

XHamster 1 year ago

Huge BBC Anal Strap on - Anal Training

Huge BBC Anal Strap on - Anal Training

XHamster 2 weeks ago

Bambilita's on-the-job Training - Video two Serving at the Diner

Bambilita's on-the-job Training - Video two Serving at the Diner

SortPorn 2 weeks ago

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

XHamster 2 months ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 1 year ago

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

XHamster 2 years ago

2 huge hands free cumshots in a row

2 huge hands free cumshots in a row

XHamster 2 years ago

Sissygasm Training

Sissygasm Training

XHamster 2 years ago

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 2 years ago

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole 1 year ago

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 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 4 years ago

Femboy instructing part 1: The Back Bend

Femboy instructing part 1: The Back Bend

Gay4Porn 2 years ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year 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

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one 4 years ago

Green-haired trans beauty solo fills anal with a long dildo

Green-haired trans beauty solo fills anal with a long dildo

Fapality 2 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

XHamster 11 months ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

Sissy Charlotte learns to suck meaty schlong

Sissy Charlotte learns to suck meaty schlong

TrannyGem 4 years ago

Lucas's Bi Slave Training

Lucas's Bi Slave Training

BeMyHole 2 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 1 year ago

A Day in the Sissy Life

70% HD 0:39 / 15:11

A Day in the Sissy Life

FapHouse 1 year ago

(1080p) Hole Training for a Future Fuckslut - Your Last Chance to Cum! Vivienne L'amour Trains You to Have Useful Holes for Her

57% HD 1:01 / 7:41

(1080p) Hole Training for a Future Fuckslut - Your Last Chance to Cum! Vivienne L'amour Trains You to Have Useful Holes for Her

FapHouse 2 weeks ago

Sissy Cumslut Training - Teaching You How to Suck and Swallow

54% HD 1:01 / 14:46

Sissy Cumslut Training - Teaching You How to Suck and Swallow

FapHouse 1 year ago

Fucked by Old Man Behind the Scenes

59% 1:01 / 28:00

Fucked by Old Man Behind the Scenes

FapHouse 1 year ago

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

56% HD 1:01 / 5:38

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

FapHouse 9 months ago

Video of Young TS Nicki at the Sissy Institute with a Bit of Bondage

Video of Young TS Nicki at the Sissy Institute with a Bit of Bondage

FapHouse 3 days ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

Caged TS Gray Perrier Submits to Sadistic Sir

68% HD 1:01 / 36:19

Caged TS Gray Perrier Submits to Sadistic Sir

FapHouse 1 month ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

69% 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

Pegging Hardcore Part 1

62% HD 1:01 / 25:58

Pegging Hardcore Part 1

FapHouse 6 months ago

POV Sissy Deep Throat and Cum Eat Humiliation Domination Striptease While Sucking

66% HD 1:01 / 23:05

POV Sissy Deep Throat and Cum Eat Humiliation Domination Striptease While Sucking

FapHouse 10 months ago

Foursome Group Sex Fuckfest

61% HD 1:01 / 40:56

Foursome Group Sex Fuckfest

FapHouse 6 months ago

WANNA BE A SISSY?

WANNA BE A SISSY?

XHamster 2 weeks ago

Sissification Appointment

Sissification Appointment

XHamster 3 months ago

All that mouth training pays off : facefucking pretty transwife Melody

All that mouth training pays off : facefucking pretty transwife Melody

Amateur8 1 year 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

Latex Maid Oral Training

Latex Maid Oral Training

BeMyHole 3 years ago

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 9 months ago

Cd Sissies Cds Version Femboy Teaching Xhwfoj

Cd Sissies Cds Version Femboy Teaching Xhwfoj

TransTube.tv 1 year ago

Instructing Your Sissy

Instructing Your Sissy

TransTube.tv 2 months ago

Actual Training at the Sissy Institute

63% HD 1:01 / 27:04

Actual Training at the Sissy Institute

FapHouse 6 months ago

Ultimate Sissy Fuck Doll Trainer

Ultimate Sissy Fuck Doll Trainer

XHamster 6 months ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TrannyGem 5 years ago

Sissy Shiera Full Goon, Sissy Training Session - Stream

Sissy Shiera Full Goon, Sissy Training Session - Stream

XHamster 2 weeks ago

Kity Slave Training

Kity Slave Training

AShemaleTube 6 years ago

Advanced Slut Training

66% HD 1:01 / 10:46

Advanced Slut Training

FapHouse 5 months ago

All that mouth training pays off : facefucking marvelous transwife Melody

All that mouth training pays off : facefucking marvelous transwife Melody

ShemaleSin 2 years ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 2 years ago

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

AShemaleTube 1 year ago

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

AShemaleTube 5 years ago

Cock Worship Boy Training

Cock Worship Boy Training

AShemaleTube 4 years ago

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin 4 years ago

Sissy Trans Analfisting

77% HD 1:01 / 6:06

Sissy Trans Analfisting

FapHouse 1 year ago

Chastity and Small Penis Humiation SPH with Hot Trans Teenager

Chastity and Small Penis Humiation SPH with Hot Trans Teenager

MyTransfix 3 weeks ago

scum Instructing jizz guzzling 2

scum Instructing jizz guzzling 2

TransTube.tv 1 year ago

Guy Feminized and Fucked by Roommate (full Movie)

Guy Feminized and Fucked by Roommate (full Movie)

XHamster 2 months ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv 1 year ago

Providing a Break From the Grind

Providing a Break From the Grind

XHamster 3 months ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 4 years ago

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem 1 year ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 1 year ago

Sophia Loreen Strip

67% HD 2:00 / 4:00

Sophia Loreen Strip

Camster 3 years ago

Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroast Cum in Mouth Humiliation Blowjob train

Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroast Cum in Mouth Humiliation Blowjob train

Itsrealamateurs 3 days ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years 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

Sissification Appointment

Sissification Appointment

XHamster 4 months ago

Femboy Assfucking Spreading With A Phat Node Fake penis

Femboy Assfucking Spreading With A Phat Node Fake penis

4Gay 9 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 3 years ago

Corporate Training - Episode 2

Corporate Training - Episode 2

XHamster 1 year ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Mature Mistress teaches two sissies how to be good cocksuckers

Mature Mistress teaches two sissies how to be good cocksuckers

Tranny.one 9 years ago

2032 - the Bwno Future

2032 - the Bwno Future

XHamster 11 months ago

Dressed in Drag for Girls Night Out

Dressed in Drag for Girls Night Out

XHamster 2 months ago

Experienced shemale training her Sissy friend @ BeautizOnCam

Experienced shemale training her Sissy friend @ BeautizOnCam

AShemaleTube 4 years ago

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

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

XHamster 5 months ago

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

XHamster 2 years 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 1 year ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 1 year ago

AB108 BadGirl FoxBae Training - Drink,screwing machine,Shemale hentai,Femdom

AB108 BadGirl FoxBae Training - Drink,screwing machine,Shemale hentai,Femdom

ShemaleSin 1 year ago

sissy Cumslut Teaching

sissy Cumslut Teaching

TrannyGem 4 years ago

G066 - Cum Swallow Compilation 2

59% 1:01 / 15:24

G066 - Cum Swallow Compilation 2

FapHouse 1 year ago

TANGENTOD - Shaped by Vanity and Lovely Temptation Episode

TANGENTOD - Shaped by Vanity and Lovely Temptation Episode

PornFreeNow 4 months ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Sissy Training Day 2. My Transformation Continues

Sissy Training Day 2. My Transformation Continues

XHamster 3 months ago

Sissy Training Compilation

Sissy Training Compilation

AShemaleTube 8 years ago

Gag Slut Training

Gag Slut Training

BeMyHole 4 years ago

Sasha's Morning Spitroast

Sasha's Morning Spitroast

XHamster 1 year ago

Sissy training

Eporner 1 year ago

Having a Hard Time - Anna Sucks Shemale Jane's Huge Cock & Swallows Cum

43% HD 0:39 / 9:34

Having a Hard Time - Anna Sucks Shemale Jane's Huge Cock & Swallows Cum

FapHouse 1 month ago

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one 4 years 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 10 months ago

Sissy Super-Bitch gets Torn Up by BIG BLACK COCK

Sissy Super-Bitch gets Torn Up by BIG BLACK COCK

TrannyGem 3 years ago

Sissy Training - guide to became sissy - (No_2)

Sissy Training - guide to became sissy - (No_2)

Itsrealamateurs 1 month ago

Experienced Shemale Trains A Chap

Experienced Shemale Trains A Chap

AShemaleTube 15 years ago

Furry trap slave training

Furry trap slave training

AShemaleTube 7 years ago

My Butt Is Made for Anal and Creampies

My Butt Is Made for Anal and Creampies

XHamster 2 years ago

Addiction to Cum

Addiction to Cum

XHamster 11 months 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

Sissy Slut Training

Sissy Slut Training

XHamster 2 years ago

Boom-Boom In VIP Room

Boom-Boom In VIP Room

Some.Porn 1 year ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 4 years ago

Obedient Sissy Crossdresser Whore Gets Guy Treated

Obedient Sissy Crossdresser Whore Gets Guy Treated

TrannyGem 4 years ago

Sissy Femboy teaching

Sissy Femboy teaching

TransTube.tv 1 month ago

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

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

Tranny.one 2 years ago

Femboy Viii tutored

Femboy Viii tutored

TransTube.tv 11 months ago

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 11 months ago

TRANNY Girls First Asshole Training Before Her Lover Shows Up

TRANNY Girls First Asshole Training Before Her Lover Shows Up

Eporner 5 months ago

Furry trap slave training

Furry trap slave training

Tranny.one 4 years ago

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem 1 year ago

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

XHamster 10 months ago

Kendall Penny Sissy Training Wih Cumshot Reward

Kendall Penny Sissy Training Wih Cumshot Reward

IcePorn 6 months ago

Humiliating Cock Sucking Training for Sissy

Humiliating Cock Sucking Training for Sissy

Tranny.one 4 years ago

Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroasting Cum in Mouth Humiliation Deep Throat BWC

Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroasting Cum in Mouth Humiliation Deep Throat BWC

XHamster 1 week ago

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

TransTube.tv 1 year ago

High Class Sissy Training

High Class Sissy Training

AbTranny 4 years ago

Ojobless Man Resorts to Sex Change to Get Hired (full Movie)

Ojobless Man Resorts to Sex Change to Get Hired (full Movie)

XHamster 2 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 11 months ago

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