Training Videos - Trans (94,320)

Pegging femboy with massive strapon!

Pegging femboy with massive strapon!

EpicGFs 2 years ago

Tv Isabella's Compilation Y-Training Scheme

Tv Isabella's Compilation Y-Training Scheme

aShemaleTube 8 months ago

Training myself for real Cocks

Training myself for real Cocks

2BGay 1 year ago

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem 1 year ago

Anal Orgasm - Hard Sissy Training And Sissygasm Compilation

Anal Orgasm - Hard Sissy Training And Sissygasm Compilation

AbTranny 2 weeks ago

Sissy training

Eporner 1 year ago

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one 4 years ago

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one 4 years ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Gym Tips for Sluts Feminization Motivation

57% HD 1:01 / 11:57

Gym Tips for Sluts Feminization Motivation

FapHouse 8 months ago

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one 4 years ago

Sissy Affirmations

Sissy Affirmations

ShemaleSin 7 months ago

Cum Dumpster Training

Cum Dumpster Training

aShemaleTube 1 year ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 4 years ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years ago

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube 2 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

xHamster 8 months ago

Training Cum Eating

Training Cum Eating

aShemaleTube 2 years ago

Training the 18 yrs boy slut from Iowa

Training the 18 yrs boy slut from Iowa

aShemaleTube 4 years ago

Slutty CD anal training & orgasm💋🍆💦💦

Slutty CD anal training & orgasm💋🍆💦💦

aShemaleTube 1 year ago

becomingfemme - natty is a beautiful blonde sissy

becomingfemme - natty is a beautiful blonde sissy

TransDoe 2 years ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

Eporner 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 1 year ago

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

AbTranny 8 years ago

Skinny trans girl with pig tails has butt sex in locker room

Skinny trans girl with pig tails has butt sex in locker room

xHamster 3 months ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 1 year ago

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 8 months ago

becomingfemme - natty is queen of the sissy university

becomingfemme - natty is queen of the sissy university

TransDoe 2 years ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 4 years ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Tranny.one 4 years ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 2 years ago

Stepdaddy's princess does what she is told

64% HD 1:01 / 25:50

Stepdaddy's princess does what she is told

FapHouse 3 years ago

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

77% 1:01 / 6:20

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

FapHouse 3 months 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

Sissy Training by Queen Daralis Part 2

54% HD 1:01 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse 4 months ago

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 2 months ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole 11 months ago

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

71% HD 0:39 / 13:39

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

FapHouse 1 year 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

Whife *

TrannyGem 6 years ago

Femboy instructing part 1: The Back Bend

Femboy instructing part 1: The Back Bend

Gay4Porn 2 years ago

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

70% 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

Addiction to Cum

Addiction to Cum

xHamster 7 months ago

Michelly Makes It Hard

76% HD 0:39 / 9:07

Michelly Makes It Hard

FapHouse 1 month 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

Kendall Penny New Orleans Gay Training

Kendall Penny New Orleans Gay Training

BeMyHole 1 year ago

Sissy Training

xHamster 1 year ago

Human Ashtray for Mistress Lilith

58% HD 1:01 / 41:36

Human Ashtray for Mistress Lilith

FapHouse 4 months ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

Sui Mizumori Riku Mukai, A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Sui Mizumori Riku Mukai, A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Eporner 1 year 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

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

Spectacular steamy T.I.L.F training toyboy

Spectacular steamy T.I.L.F training toyboy

KeekAss 5 years ago

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube 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 7 months ago

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube 8 years ago

Shemale Pussy Denial

68% HD 0:20 / 13:02

Shemale Pussy Denial

IWantClips 1 year ago

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 1 year ago

Extra Large Cock Training

Extra Large Cock Training

Eporner 6 months ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 9 months ago

Good Girl Training: Transfemme Anal JOI

45% HD 1:01 / 17:10

Good Girl Training: Transfemme Anal JOI

FapHouse 2 months ago

[Trans] Eva Maxim Breaks You In!

61% VR 1:30 / 34:20

[Trans] Eva Maxim Breaks You In!

VRPorn 1 year ago

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

TransTube.tv 1 year ago

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

TrannyGem 3 years ago

mistress training kinky sissy bitch

mistress training kinky sissy bitch

Itsrealamateurs 1 week ago

Petra in virgin white,s

Petra in virgin white,s

xHamster 2 months ago

Feminization Training - Show This To Your Wife

Feminization Training - Show This To Your Wife

xHamster 1 year ago

Getting Ready with Sissy Maid Candy!

Getting Ready with Sissy Maid Candy!

xHamster 2 months ago

Pussy Wrecking Vol.1

HD 1:01 / 14:02

Pussy Wrecking Vol.1

FapHouse 1 week ago

Sissy Fuckdoll 2

Sissy Fuckdoll 2

xHamster 6 months ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 10 months ago

feminisation training

feminisation training

xHamster 5 months ago

Just because I can..

Just because I can..

xHamster 2 years ago

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin 4 years ago

Femboy sissy training rides BBC dildo

Femboy sissy training rides BBC dildo

aShemaleTube 2 years ago

Sissy Conversion Therapy - Part 1

HD 1:01 / 10:59

Sissy Conversion Therapy - Part 1

FapHouse 9 months ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 1 year ago

Sissy Fuck Training

Sissy Fuck Training

aShemaleTube 4 years ago

Slut training! (strapon spitroast & double penetration)

47% HD 0:10 / 18:25

Slut training! (strapon spitroast & double penetration)

LoyalFans 11 months ago

Kitty training her ass💗

Kitty training her ass💗

aShemaleTube 1 year ago

Slutty Sissy gets hard training Blowjob and Fuck Rough

Slutty Sissy gets hard training Blowjob and Fuck Rough

aShemaleTube 4 months ago

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 4 months ago

Feminization Sissification Sissy Threesome Training Blowjob

Feminization Sissification Sissy Threesome Training Blowjob

BeMyHole 1 year ago

Sissy Dolly Basement Have Fun Time Pegged by Giant Bad Dragon Strap Dildo and Abased by Domina Mercer

Sissy Dolly Basement Have Fun Time Pegged by Giant Bad Dragon Strap Dildo and Abased by Domina Mercer

TrannyGem 3 years ago

Jobless Man Resorts to Feminization to Get Hired

Jobless Man Resorts to Feminization to Get Hired

xHamster 2 weeks ago

Sissy trainer - Give your ass

Sissy trainer - Give your ass

DeegX 3 years ago

Hole Training

Eporner 1 year ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube 7 months ago

Ultimate Sissy Fuck Doll Trainer

Ultimate Sissy Fuck Doll Trainer

xHamster 3 months ago

Female Dominance Domme tears up fuckslut sissy backside, dual jism rectal ejaculation

Female Dominance Domme tears up fuckslut sissy backside, dual jism rectal ejaculation

TrannyGem 2 years ago

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

xHamster 7 months ago

sluttami

ShemaleSin 5 years ago

Big ass Latina gets facial after anal fuck - Amateur Porn

Big ass Latina gets facial after anal fuck - Amateur Porn

MyLust 2 years ago

Public GOING KNUCKLE DEEP sissy ARSE

Public GOING KNUCKLE DEEP sissy ARSE

TrannyGem 3 years ago

Tranny Training

Tranny Training

Eporner 1 year ago

Ts dominates couple Analmal Training

Ts dominates couple Analmal Training

Eporner 4 years ago

dame-domineering Teaches Her shelady damsels

dame-domineering Teaches Her shelady damsels

TrannyGem 6 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 Fuckdoll

xHamster 1 year ago

Sissy Maid Is Taught Proper Manners

60% 1:01 / 25:25

Sissy Maid Is Taught Proper Manners

FapHouse 6 months ago

Glazing Her Lil' Inverted Pearl In Sissy Juices

Glazing Her Lil' Inverted Pearl In Sissy Juices

TrannyGem 2 years ago

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 1 year ago

Training Journal 20260408

Training Journal 20260408

xHamster 2 months ago

Sasha's Morning Spitroast

Sasha's Morning Spitroast

xHamster 11 months 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 1 year ago

9s Feminisation Training Nier Automata Futanari 3D Porn

9s Feminisation Training Nier Automata Futanari 3D Porn

Pornwhite 4 weeks ago

Slender Japanese shemale trained in bondage and submission

Slender Japanese shemale trained in bondage and submission

PornLib 4 years ago

RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

xHamster 4 years ago

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

Tranny.one 4 years ago

Trannies in Training - EPISODE #01

Trannies in Training - EPISODE #01

Tranny.one 3 years ago

My Sissy Anal Training

My Sissy Anal Training

Pornzona 1 month ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

aShemaleTube 1 year ago

Big ass goddess trains new sub

Big ass goddess trains new sub

aShemaleTube 3 years ago

Sissies are Made to be Servants

Sissies are Made to be Servants

ShemaleSin 8 months ago

Lianna Lawson - Piggy Princess Training

Lianna Lawson - Piggy Princess Training

AbTranny 4 years ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

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

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

xHamster 11 months ago

Anal Alien Eggs Insemination Femdom

60% HD 1:01 / 10:55

Anal Alien Eggs Insemination Femdom

FapHouse 4 weeks ago

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 1 week ago

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