Training Videos - Trans (126,562)

Sissy Femboy Bondage Feminization Training

Sissy Femboy Bondage Feminization Training

XHamster 1 year ago

Sex Slaves with Lucy

68% 0:30 / 10:17

Sex Slaves with Lucy

Clips4sale 1 year ago

Training with My Trans Stepsister Ends with a Facial

64% HD 1:01 / 15:34

Training with My Trans Stepsister Ends with a Facial

FapHouse 3 weeks ago

doggy besamt!!! trans girl im fitnessstudio aufgerissen!

53% HD 0:30 / 15:28

doggy besamt!!! trans girl im fitnessstudio aufgerissen!

PornBox 2 years ago

Toga Convinces You to Cross Dress

Toga Convinces You to Cross Dress

XHamster 9 months ago

Sissy Candy Playing with Dildos Part 3

Sissy Candy Playing with Dildos Part 3

AShemaleTube 5 months ago

Amateur MILF gets a double dose of kinky training with a shemale twist

Amateur MILF gets a double dose of kinky training with a shemale twist

TrannyMovs 1 month ago

Sissified By My Recent Roomate (Sissy Caption Story)

Sissified By My Recent Roomate (Sissy Caption Story)

ShemaleSin 2 months ago

Nightshade Defeats Superman

57% 0:39 / 13:31

Nightshade Defeats Superman

FapHouse 9 months ago

Hugeload Bigdick

69% HD 1:01 / 14:25

Hugeload Bigdick

FapHouse 6 months ago

Sissy Wench Lola Crystals getting impaled on a Monster Ebony Ramrod

Sissy Wench Lola Crystals getting impaled on a Monster Ebony Ramrod

ShemaleSin 4 years ago

Romantic BDSM Lesbians Date Night Pussy Worship ft River Enza - 4K MP4

4K 0:32 / 12:12

Romantic BDSM Lesbians Date Night Pussy Worship ft River Enza - 4K MP4

Clips4sale 2 years ago

Tiny Sissy Fucked by Daddy Dong King Part 2

Tiny Sissy Fucked by Daddy Dong King Part 2

FapHouse 5 months ago

Widely Opened Brown Sphincter Internal Cumshot from uber-cute ladyboy

Widely Opened Brown Sphincter Internal Cumshot from uber-cute ladyboy

TrannyGem 1 year ago

Lilit Hot Private Show

64% HD 2:00 / 44:28

Lilit Hot Private Show

Flirt4Free 1 month ago

Sissy Slut Humiliation

Premium HD 7:27

Sissy Slut Humiliation

Sheer 1 week ago

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

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

AbTranny 3 years ago

In For the Evening: Ryley and Ava Holt

65% HD 0:29 / 25:02

In For the Evening: Ryley and Ava Holt

Clips4sale 4 years ago

Cock stroking Asian Am takes a cock before a sensual shave

Cock stroking Asian Am takes a cock before a sensual shave

ShemalesTube 7 years ago

FISTING PISSING CUM PRECUM HOTSHOTS COMPILATION

Premium HD 5:12

FISTING PISSING CUM PRECUM HOTSHOTS COMPILATION

Sheer 1 year ago

Step-Son Bullied into Becoming Neighborhood Sissy Maid

HD 0:30 / 12:00

Step-Son Bullied into Becoming Neighborhood Sissy Maid

Clips4sale 1 year ago

SAY - I DESERVE TO BE FUCKED BY BBC!

4K 0:25 / 14:06

SAY - I DESERVE TO BE FUCKED BY BBC!

Clips4sale 3 years ago

Sister Jenny Goes Back To Training With Big White Cock - Jenny Wei

Sister Jenny Goes Back To Training With Big White Cock - Jenny Wei

AbTranny 3 years ago

THE TRAINING OF MY TS SLAVEGIRL *HD 1080*

63% HD 0:10 / 19:19

THE TRAINING OF MY TS SLAVEGIRL *HD 1080*

LoyalFans 2 years ago

Routine Inspection Pt 1

67% HD 0:10 / 11:43

Routine Inspection Pt 1

LoyalFans 1 year ago

Breezy Girl being drilled by big cock

Breezy Girl being drilled by big cock

XHamster 5 months ago

Transgirl in Chastity Humps Her Pillows

Transgirl in Chastity Humps Her Pillows

ShemaleSin 9 months ago

Sissy Training with Mistress

Sissy Training with Mistress

TrannyGem 7 years ago

Muscular Sasha with Huge Cock! Muscle and Futa Fetish

55% 0:57 / 10:04

Muscular Sasha with Huge Cock! Muscle and Futa Fetish

Clips4sale 3 years ago

Boobs, caged cock in a corset with dildo

Boobs, caged cock in a corset with dildo

XHamster 2 years ago

Trans on a Fuckmachine for Her Neighbor

Trans on a Fuckmachine for Her Neighbor

XHamster 1 year ago

Working My trannies Tight Hole

Working My trannies Tight Hole

Clips4sale 1 month ago

Futa Oral Worship: Demon Goddess

Futa Oral Worship: Demon Goddess

Clips4sale 1 year ago

Slut Training Of Rana Katana

Slut Training Of Rana Katana

DrTuber 8 months ago

Come on, honey.. I&#039;ll fuck your ass. Stepmom testing stepsons anal hole.

Come on, honey.. I&#039;ll fuck your ass. Stepmom testing stepsons anal hole.

XHamster 1 year ago

Jasmine_dlight & Pixie Vanora - Gaped Booty Used as a Crapper Woman Pee's in Butt, Then a Prolapse

Jasmine_dlight & Pixie Vanora - Gaped Booty Used as a Crapper Woman Pee's in Butt, Then a Prolapse

ShemaleSin 1 month ago

Marian & Richard Private Show

55% HD 2:00 / 5:27

Marian & Richard Private Show

Camster 4 months ago

Watch this kinky brunette give a sloppy deep-throat handjob and blowjob with toys

Watch this kinky brunette give a sloppy deep-throat handjob and blowjob with toys

TrannyMovs 4 days ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 2 years ago

Bi Mmf Anal Trains Compilation

Bi Mmf Anal Trains Compilation

GetTranny 3 years ago

Extreme Puppy Endurance Hell While Wearing a Flat Chastity Cage and 55mm Gag

Premium 1:04:53

Extreme Puppy Endurance Hell While Wearing a Flat Chastity Cage and 55mm Gag

Clips4sale 10 months ago

Anal Training 101

HD 0:39 / 34:30

Anal Training 101

FapHouse 3 weeks ago

Sara & Elver Private Show

66% HD 2:00 / 8:25

Sara & Elver Private Show

Camster 10 months ago

TS Sucker For Ebony Feet Gets Tease & Ballbusting MOV | MahoganyQen with Julia Masakova

4K 0:25 / 14:12

TS Sucker For Ebony Feet Gets Tease & Ballbusting MOV | MahoganyQen with Julia Masakova

Clips4sale 5 days ago

Morning routine with chinese t-girl LEITAOXIV

Morning routine with chinese t-girl LEITAOXIV

Gayhub 1 year ago

Transformation Feminized Build-A-Slut: My Fuckhole

Transformation Feminized Build-A-Slut: My Fuckhole

ShemaleSin 1 month ago

Grace Keller Private Show

HD 2:00 / 12:52

Grace Keller Private Show

Flirt4Free 2 years ago

Sissygasm Slut U2019s Caged Training Massive Cumshots A

Sissygasm Slut U2019s Caged Training Massive Cumshots A

Eporner 1 year ago

Bukkake Training for Sissy Strumpets

Bukkake Training for Sissy Strumpets

ShemaleSin 5 years ago

Japanese Femdom, Reiko Butler's Slave Domestication Training

Japanese Femdom, Reiko Butler's Slave Domestication Training

XHamster 6 years ago

It's My Birthday, so I Get What I Want

63% HD 0:39 / 21:21

It's My Birthday, so I Get What I Want

FapHouse 1 month ago

Vanessa Blue Strap On Toilet Training POV VBBC

Vanessa Blue Strap On Toilet Training POV VBBC

AbTranny 7 years ago

Watch two naughty damsels-in-training get their tight holes drilled by a hot young stud

Watch two naughty damsels-in-training get their tight holes drilled by a hot young stud

TrannyMovs 6 months ago

Sissy Tutor Encouragement Crossdresser BBC Interracial Fiona Fortune

Sissy Tutor Encouragement Crossdresser BBC Interracial Fiona Fortune

ShemaleSin 11 months ago

Sissies Cum In Their Panties

58% HD 0:10 / 9:50

Sissies Cum In Their Panties

LoyalFans 3 years ago

The Reformatory Part 3

The Reformatory Part 3

Clips4sale 1 year ago

Twerk Scene / Pink Lingerie Set

Twerk Scene / Pink Lingerie Set

Camster 2 weeks ago

Million Or Makeover Episode 1

Premium HD 15:13

Million Or Makeover Episode 1

Clips4sale 1 month ago

Ts Daniela Marks turns Hex into her Sissy Slut (720p ENG-sub) Trans Woman - Sissy Slut - Sissy Fucking - Trans Blowjob - Trans Cock

62% HD 0:22 / 18:08

Ts Daniela Marks turns Hex into her Sissy Slut (720p ENG-sub) Trans Woman - Sissy Slut - Sissy Fucking - Trans Blowjob - Trans Cock

Clips4sale 1 year ago

Sissy Doesn't Go Toilet. Sissy Pisses in Panties.

Sissy Doesn't Go Toilet. Sissy Pisses in Panties.

XHamster 11 months ago

Chastity and Small Penis Humiation SPH with Hot Trans Teenager

Chastity and Small Penis Humiation SPH with Hot Trans Teenager

MyTransfix 1 month ago

Perfect Sissy Slut Training

Perfect Sissy Slut Training

Clips4sale 2 years ago

Felicia Anderson Private Show

Felicia Anderson Private Show

Flirt4Free 2 years ago

Naughty Therapist helps guide you to your New Sissy Life

Naughty Therapist helps guide you to your New Sissy Life

XHamster 2 months ago

extreme Nipple Play

extreme Nipple Play

XHamster 4 years ago

Sissy Slut Toy Training

HD 0:20 / 11:22

Sissy Slut Toy Training

IWantClips 4 months ago

Latex slave ass stretching (720p)

Latex slave ass stretching (720p)

Clips4sale 4 years ago

Shemale Julie Rouch Ends up with a Creampie After Anal Train Threeway

Shemale Julie Rouch Ends up with a Creampie After Anal Train Threeway

XHamster 3 years ago

Prison or a Sissy Diaper Ballerina

52% 0:30 / 16:26

Prison or a Sissy Diaper Ballerina

Clips4sale 1 year ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 2

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 2

ShemaleSex 8 months ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Girl

45% 1:01 / 37:48

Petite Trans Kawaii Fiona Fucks a Submissive Trans Girl

FapHouse 2 years ago

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Gayhub 10 months ago

ORAL-JOB EDUCTION: Large Ass Fem Male Shows How to Suck Large Schlong and Deepthroat - Sissy Training

ORAL-JOB EDUCTION: Large Ass Fem Male Shows How to Suck Large Schlong and Deepthroat - Sissy Training

ShemaleSin 3 years ago

Training Ebony Sissy Aliza to serve a Large Weenie White Dad Spitroasting Cum in Throat Humiliation Unfathomable Mouth BWC

Training Ebony Sissy Aliza to serve a Large Weenie White Dad Spitroasting Cum in Throat Humiliation Unfathomable Mouth BWC

ShemaleSin 1 month ago

SISSY INSPECTORS #1: MAID TO PERFORM

HD 0:30 / 11:12

SISSY INSPECTORS #1: MAID TO PERFORM

Clips4sale 4 years ago

sissy sonya on gynochair nailed by screwing machine

sissy sonya on gynochair nailed by screwing machine

TrannyGem 3 years ago

Crhistian & Dereckk & Friends Private Show

66% HD 2:00 / 6:56

Crhistian & Dereckk & Friends Private Show

Flirt4Free 8 years ago

She Her JOI For TransWomen - JOI - Female Pronouns - Masturbation Encouragement

60% 4K 0:54 / 9:46

She Her JOI For TransWomen - JOI - Female Pronouns - Masturbation Encouragement

Clips4sale 2 years ago

Training Season Ft Slutty Stepdaddy Pt.1

HD 0:39 / 12:05

Training Season Ft Slutty Stepdaddy Pt.1

FapHouse 2 years ago

Alexxa A Private Show

64% HD 2:00 / 3:48

Alexxa A Private Show

Camster 1 month ago

How I’d really FEMINIZE you to the max

63% HD 0:28 / 9:33

How I’d really FEMINIZE you to the max

Clips4sale 5 months ago

Sissy trainer - Give your ass

Sissy trainer - Give your ass

Fapcat 4 years ago

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

XHamster 1 year ago

Ava Venom Fucked and Pegged with Strapon Ft Daddy Dahlia Xene

64% 0:30 / 10:50

Ava Venom Fucked and Pegged with Strapon Ft Daddy Dahlia Xene

Clips4sale 1 year ago

Workout in underware! T-girl cutie is so lascivious, this babe has to cum!

Workout in underware! T-girl cutie is so lascivious, this babe has to cum!

Amateur8 2 weeks ago

Fucking Machine Satisfies Sissy Whore with Wide Open Legs

Fucking Machine Satisfies Sissy Whore with Wide Open Legs

XHamster 1 month ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

ShemaleSin 1 year ago

Dancing ladyboy with lil' bud

Dancing ladyboy with lil' bud

TrannyGem 4 years ago

Naomi Chi in TS Training - IKillItTs

Naomi Chi in TS Training - IKillItTs

Xshemale 10 years ago

Muslim Sissy the Perfect Sissygasm

Muslim Sissy the Perfect Sissygasm

XHamster 1 month ago

Trans Ria Bentley Trains Stepdaughter Eden Espi For Anal Sex 7 Min

Trans Ria Bentley Trains Stepdaughter Eden Espi For Anal Sex 7 Min

AbTranny 11 months ago

Sarait Gil Private Show

61% HD 2:00 / 6:20

Sarait Gil Private Show

Flirt4Free 2 years ago

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

TrannyGem 4 years ago

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

FapHouse 2 months ago

8K UNMASKED - KPop Femboy Cum Swallowing Session

71% 4K 0:24 / 37:10

8K UNMASKED - KPop Femboy Cum Swallowing Session

Clips4sale 1 year ago

Anal training for Sissy Blaire_eighteen. Dominatrix-bitch Nika inserts anal beads into her Sissy's little booty.

Anal training for Sissy Blaire_eighteen. Dominatrix-bitch Nika inserts anal beads into her Sissy's little booty.

ShemaleSin 1 year ago

Sissy Zone Cycle 2

Sissy Zone Cycle 2

Clips 2 weeks ago

Sophia Loreen Party on Sep 7, 2026 - Part 3

63% 4K 2:00 / 4:07

Sophia Loreen Party on Sep 7, 2026 - Part 3

Flirt4Free 1 month ago

V-card Cell Challange - Day nine/30

V-card Cell Challange - Day nine/30

Gayhub 1 year ago

Personal selection of exciting handjob and hot endings from a sexy femboy.

Personal selection of exciting handjob and hot endings from a sexy femboy.

XCafe 2 years ago

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

PissVids 1 year 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 2 years ago

Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll

Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll

XHamster 2 years ago

Sophie Fantasy Private Show

Sophie Fantasy Private Show

Flirt4Free 2 months ago

Uncut Cock Stretches Tattooed Latin Hole Deep

Uncut Cock Stretches Tattooed Latin Hole Deep

GaysTubes 2 weeks ago

Trained to be completely subservient to him

Trained to be completely subservient to him

Clips4sale 2 days ago

Ms Minxy’s Eternal Bareback Submission

63% 4K 0:30 / 23:29

Ms Minxy’s Eternal Bareback Submission

Clips4sale 1 year ago

My Butt Is Made for Anal and Creampies

63% HD 0:39 / 22:24

My Butt Is Made for Anal and Creampies

FapHouse 2 years ago

Alejandra Fox Private Show

52% HD 2:00 / 23:50

Alejandra Fox Private Show

Flirt4Free 1 year ago

Miss Rose's Slutschool - Toilet training

Miss Rose's Slutschool - Toilet training

XHamster 3 years ago

Sissy blows a load inwards undies

Sissy blows a load inwards undies

TrannyGem 11 months ago

Tranpires, Scene 2: The Rockstar FULL SCENE

64% 4K 0:30 / 29:58

Tranpires, Scene 2: The Rockstar FULL SCENE

Clips4sale 4 years ago

Training Like a Good Gurl

Training Like a Good Gurl

XHamster 7 months ago

dual View Sexy Crossdresser in Corset and fishnet gets machine fucked

dual View Sexy Crossdresser in Corset and fishnet gets machine fucked

XHamster 2 years ago

Corrine Dittmann Private Show

4K 2:00 / 24:21

Corrine Dittmann Private Show

Camster 4 months ago

SLAVE FARM SISSY AUDITION | Vivienne l'Amour tests Sissys suitability as the new house fluffer to service The Bulls with Deep Throat & Intense PEGGING

60% HD 0:10 / 22:21

SLAVE FARM SISSY AUDITION | Vivienne l'Amour tests Sissys suitability as the new house fluffer to service The Bulls with Deep Throat & Intense PEGGING

LoyalFans 1 month ago

Go Gay For My Popularity

45% 0:24 / 7:42

Go Gay For My Popularity

Clips4sale 3 years ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

XHamster 11 months ago

Tennis Club Sissy

66% 0:39 / 16:58

Tennis Club Sissy

FapHouse 1 year ago

Duan Anal Training Topping Bareback

Duan Anal Training Topping Bareback

AbTranny 1 year ago

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