Training Videos - Trans (87,412)

BBC & Lingerie Fuckmachine - Huge Orgasm

BBC & Lingerie Fuckmachine - Huge Orgasm

xHamster 8 months ago

Blowjob service for my Dominatrix.

Blowjob service for my Dominatrix.

TransTube.tv 1 year ago

The Mistress's Punishment for the Cross-dressing Masochistic Man Is Strapon Deepthroating, Hot Wax, and Whipping

The Mistress's Punishment for the Cross-dressing Masochistic Man Is Strapon Deepthroating, Hot Wax, and Whipping

xHamster 1 month ago

Alejandra Fox Party on Mar 1, 2026 - Part 2

HD 2:00 / 19:42

Alejandra Fox Party on Mar 1, 2026 - Part 2

Flirt4Free 1 day ago

Submissive Crossdresser's Blowjob Training

Submissive Crossdresser's Blowjob Training

Eporner 1 month ago

boinking with a stranger my sissy bi-atch

boinking with a stranger my sissy bi-atch

TrannyGem 2 years ago

Ts Isabella likes sissy training for English Mistresses

Ts Isabella likes sissy training for English Mistresses

ShemaleSin 3 years ago

Teasing Our Slut - Brat Perversions

Teasing Our Slut - Brat Perversions

Some.Porn 1 year ago

ROCK-HARD SISSY TRAINNING OUTDOOR BY ENORMOUS BELT COCK

ROCK-HARD SISSY TRAINNING OUTDOOR BY ENORMOUS BELT COCK

TrannyGem 1 year ago

Veronica Taboo's ultimate guide to sissy training with kinky toys

Veronica Taboo's ultimate guide to sissy training with kinky toys

TrannyMovs 5 months ago

Big Toys Make Big Cumshots

Big Toys Make Big Cumshots

xHamster 1 month ago

Sophia Loreen Private Show

4K 2:00 / 15:12

Sophia Loreen Private Show

Flirt4Free 1 week ago

get on your knees sissy

get on your knees sissy

ShemaleSin 1 year ago

Hot girlz big booty ai hotties steaming up your screen

Hot girlz big booty ai hotties steaming up your screen

xHamster 2 years ago

Trans Eva Joi Gets Dominated by TS Ria Bentley With Double Anal Toy

Trans Eva Joi Gets Dominated by TS Ria Bentley With Double Anal Toy

ShemaleSin 2 years ago

Cd Sissies Cds Version Femboy Teaching Xhwfoj

Cd Sissies Cds Version Femboy Teaching Xhwfoj

TransTube.tv 8 months ago

Sissy Instructing Part two

Sissy Instructing Part two

TrannyGem 5 years ago

Ekaterina Jazmine Private Show

Ekaterina Jazmine Private Show

Flirt4Free 2 months ago

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

68% HD 1:01 / 10:16

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

FapHouse 1 month ago

Brunette Shemale In Crotchless Fishnet Pantyhose Surrenders Her Asshole To a Merciless Fuck-machine

Brunette Shemale In Crotchless Fishnet Pantyhose Surrenders Her Asshole To a Merciless Fuck-machine

XGroovy 2 years ago

GIANTESS SHEMALES DESTROY THE CITY

61% HD 0:10 / 10:13

GIANTESS SHEMALES DESTROY THE CITY

LoyalFans 7 months ago

two Dommes and their trans floozy! Drubbing, FemDom, Humiliation

two Dommes and their trans floozy! Drubbing, FemDom, Humiliation

ShemaleSin 7 months ago

Supreme North Anal Training In The Hotel Room

Supreme North Anal Training In The Hotel Room

DrTuber 1 month ago

Sexy Mistress pegging Sissy cowboy slut

Sexy Mistress pegging Sissy cowboy slut

xHamster 1 year ago

Sissy boi gets his cock & balls pulled whilst his ass being pounded

Sissy boi gets his cock & balls pulled whilst his ass being pounded

xHamster 1 year ago

Instructions From the Trainer No17 Bread Enema Walking Part1

HD 0:39 / 12:22

Instructions From the Trainer No17 Bread Enema Walking Part1

FapHouse 5 days ago

Femdom Mistress Pegging Sissy

Femdom Mistress Pegging Sissy

TrannyGem 7 years ago

Submissive Skinny Ladyboy Homemade First Anal

Submissive Skinny Ladyboy Homemade First Anal

xHamster 3 weeks ago

CHASTITY TRAINING // Transgirl Plugs her Booty and Cums during the time that Caged // Milky Lynn

CHASTITY TRAINING // Transgirl Plugs her Booty and Cums during the time that Caged // Milky Lynn

BigTitsLust 4 months ago

Fur sissy deepthroat for master

Fur sissy deepthroat for master

xHamster 1 year ago

Anal Orgasm in Chastity

Anal Orgasm in Chastity

xHamster 1 week ago

BDSM Sissy Slut get punish and hits

BDSM Sissy Slut get punish and hits

xHamster 1 year ago

Thippy Top Training

Thippy Top Training

PornUse 4 months ago

Sissy Booty Bitch Pt2 Preview

Sissy Booty Bitch Pt2 Preview

ShemaleSin 2 years ago

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking

52% HD 0:10 / 32:41

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking

LoyalFans 5 months ago

Viky & Master Private Show

61% HD 2:00 / 9:03

Viky & Master Private Show

Flirt4Free 1 month ago

Independent Training No20 Exposure Walk with a Chastity Belt

Independent Training No20 Exposure Walk with a Chastity Belt

FapHouse 3 months ago

Master & Christian & Nicco Private Show

63% HD 2:00 / 6:22

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

Little slut bottom getting trained to take girl dick

Little slut bottom getting trained to take girl dick

xHamster 2 weeks ago

Fag slave humiliation compilation part 8

Fag slave humiliation compilation part 8

xHamster 1 month ago

shebari training

shebari training

xHamster 3 months ago

Frisky night into the parking lot

Frisky night into the parking lot

xHamster 1 year ago

this babemale Ariel trains guy Mmm

this babemale Ariel trains guy Mmm

TrannyGem 6 years ago

Multiformity Itsol HFO training mindfuck

Multiformity Itsol HFO training mindfuck

FreePorn8 1 month ago

Patiently Expecting for Her Alpha

Patiently Expecting for Her Alpha

ShemaleSin 2 months ago

Alexxa A Private Show

HD 2:00 / 11:05

Alexxa A Private Show

Flirt4Free 1 week ago

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

xHamster 2 years ago

Youngster catboy fellates plaything and imagines it humping his face

Youngster catboy fellates plaything and imagines it humping his face

TrannyGem 2 years ago

ideal booty and taut aperture of a charming femboy gets drilled hard by a sex machine and cums

ideal booty and taut aperture of a charming femboy gets drilled hard by a sex machine and cums

ShemaleSin 9 months ago

Small penis sissy hubby gets pegged & humiliated

Small penis sissy hubby gets pegged & humiliated

xHamster 6 months ago

Machine Fuck Purple Lingerie

Machine Fuck Purple Lingerie

xHamster 1 year ago

Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.

Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.

xHamster 11 months ago

Stars Of Salvation - Ep.19 - End Update By MissKitty2K

Stars Of Salvation - Ep.19 - End Update By MissKitty2K

xHamster 1 year ago

Riding dildo in slow motion

Riding dildo in slow motion

xHamster 10 months ago

Sissy's asshole is filled up to a meter deep

Sissy's asshole is filled up to a meter deep

xHamster 1 year ago

Lovely she-male gives the most sloppiest strong oral to a gamer with a fat man rod

Lovely she-male gives the most sloppiest strong oral to a gamer with a fat man rod

TrannyGem 1 year ago

FEMDOM SISSY TRAINNING COMPILATION

FEMDOM SISSY TRAINNING COMPILATION

xHamster 1 year ago

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

xHamster 4 months ago

Spandex Sissy Assfuck Ass Inside-Out

Spandex Sissy Assfuck Ass Inside-Out

TrannyGem 2 years ago

Devin and Wendy Williams

Devin and Wendy Williams

xHamster 1 year ago

Japanese Femdom, Reiko Butler's Slave Domestication Training

Japanese Femdom, Reiko Butler's Slave Domestication Training

xHamster 5 years ago

THE TRAINING OF MY TS SERF ANGEL

THE TRAINING OF MY TS SERF ANGEL

ShemaleSin 4 years ago

Dress Up Sissy Costume Tasks

Dress Up Sissy Costume Tasks

xHamster 4 months ago

Sissy Monique - Showing myself in front of a porn cinema - Part 1

Sissy Monique - Showing myself in front of a porn cinema - Part 1

xHamster 4 months ago

Women Pub Vignette five: A Sissy Feminization Series

Women Pub Vignette five: A Sissy Feminization Series

TrannyGem 5 years ago

Trainning My Sissy Ass with a Huge Dildo - Sissy Trainning - Full Movie

Trainning My Sissy Ass with a Huge Dildo - Sissy Trainning - Full Movie

xHamster 4 months ago

This Guy Made It Rain a Lot of Cum on My White Boy Face

This Guy Made It Rain a Lot of Cum on My White Boy Face

xHamster 1 year ago

Hairy Stud Ricky Larkin Trains TS Slut Rachael Belle With A Dildo!

Hairy Stud Ricky Larkin Trains TS Slut Rachael Belle With A Dildo!

XVideos 1 year ago

Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 23022023

Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 23022023

xHamster 2 years ago

Desire Sweet Private Show

HD 2:00 / 12:46

Desire Sweet Private Show

Flirt4Free 2 days ago

Builder job at work anal stimulating BDSM public

Builder job at work anal stimulating BDSM public

xHamster 7 months ago

Making My Cock Explode

55% HD 0:39 / 8:10

Making My Cock Explode

FapHouse 4 months ago

Trans joi. Intensive edge, ruin and then cum with me. Biggest load

Trans joi. Intensive edge, ruin and then cum with me. Biggest load

ShemaleSin 3 years ago

my husband turns his pathetic cock into a pretty pussy

my husband turns his pathetic cock into a pretty pussy

xHamster 2 years ago

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TrannyGem 5 years ago

Tightening To Spunk From Ass-Fuck In Her Vapid Tiny Cell

Tightening To Spunk From Ass-Fuck In Her Vapid Tiny Cell

TrannyGem 1 year ago

”GROOBYGIRLS: Rah Rah Amber Analeise”

”GROOBYGIRLS: Rah Rah Amber Analeise”

TransHero 1 year ago

BBC Sissygasm

65% 0:39 / 1:42

FapHouse 7 months ago

Sissy Cumslut Training - Teaching You How to Suck and Swallow

50% HD 0:39 / 14:46

Sissy Cumslut Training - Teaching You How to Suck and Swallow

FapHouse 11 months ago

Couple and T-model milf in the dungeon part 1

Couple and T-model milf in the dungeon part 1

TransTube.tv 1 year ago

Lesbian Shemale Making Love in Japanese School Uniform

Lesbian Shemale Making Love in Japanese School Uniform

xHamster 11 months ago

Transgender in high heels and lingerie does anal beads

Transgender in high heels and lingerie does anal beads

xHamster 1 year ago

Sophia Loreen Party on May 17, 2025 - Part 2

46% 4K 2:00 / 21:35

Sophia Loreen Party on May 17, 2025 - Part 2

Flirt4Free 9 months ago

Bunny-butler Reina Hanno Sucking Two Dildos

48% HD 1:01 / 23:41

Bunny-butler Reina Hanno Sucking Two Dildos

FapHouse 5 months ago

Cute Girl rides super huge Dildo and stretches her tiny pussy

Cute Girl rides super huge Dildo and stretches her tiny pussy

xHamster 2 years ago

Sissy Anal Games

Sissy Anal Games

xHamster 2 weeks ago

Sissy Bimbo Training

Sissy Bimbo Training

AbTranny 7 years ago

Microbikini Sissy Wearing a Girl's Chastity Belt Takes 1.2L Up Her Ass

Microbikini Sissy Wearing a Girl's Chastity Belt Takes 1.2L Up Her Ass

xHamster 2 months ago

Stepmother helps her horny sissy stepson cum hard

Stepmother helps her horny sissy stepson cum hard

xHamster 1 year ago

Aron & Elvis & Hercules Private Show

68% HD 2:00 / 8:56

Aron & Elvis & Hercules Private Show

Flirt4Free 3 years ago

Sexy Latina with Big Tits

63% HD 2:00 / 19:06

Sexy Latina with Big Tits

Flirt4Free 1 year ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 3

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 3

xHamster 1 month ago

Femdom EXTREME wet & messy ANAL training

Femdom EXTREME wet & messy ANAL training

xHamster 1 year ago

Sasha Earth – sissy slut has anal sex with Anastasia Mistress

Sasha Earth – sissy slut has anal sex with Anastasia Mistress

xHamster 3 years ago

Goddess Kyaa Books and Beatings

Goddess Kyaa Books and Beatings

its.PORN 4 years ago

Wifey makes vid of sissy hubby romping himself in the backside like a tramp.

Wifey makes vid of sissy hubby romping himself in the backside like a tramp.

Gayhub 5 months ago

Dimitry Rolex & Liliith Private Show

Dimitry Rolex & Liliith Private Show

Flirt4Free 2 years ago

Brihana Boll Private Show

HD 2:00 / 55:18

Brihana Boll Private Show

Flirt4Free 2 months ago

Lanna & Nefertiti Private Show

Lanna & Nefertiti Private Show

Flirt4Free 2 years ago

Super-fucking-hot sissy femboy trans deep-inhaling fuck stick

Super-fucking-hot sissy femboy trans deep-inhaling fuck stick

TransTube.tv 1 year ago

Sissy Transition CLINIC - Obedience Training

Sissy Transition CLINIC - Obedience Training

xHamster 1 year ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 10:13

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 16:28

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Wanna my pussy enjoy and get super wet! I love to be naughty...what if we dod a gangbang? NEED 4 MEN TO FUCK MY PUSSY!

Wanna my pussy enjoy and get super wet! I love to be naughty...what if we dod a gangbang? NEED 4 MEN TO FUCK MY PUSSY!

Flirt4Free 4 years ago

Naruto Sarada feet and ass play trap cosplay

63% HD 1:01 / 23:02

Naruto Sarada feet and ass play trap cosplay

FapHouse 4 years ago

Luke Hardy & Cristian Ford Private Show

48% HD 2:00 / 18:14

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

bareback fuck and hard anal acrobat punch fisting - christmas special

65% 2:35 / 28:56

bareback fuck and hard anal acrobat punch fisting - christmas special

AnalVids 2 months ago

BIG BLACK COCK T-MODEL ROLL PLOW BOY FUCK-HOLE HUMID

BIG BLACK COCK T-MODEL ROLL PLOW BOY FUCK-HOLE HUMID

TrannyGem 3 years ago

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

IFuckedYourGF 3 months ago

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

GayCK 4 years ago

Chatty crossdresser tries out new depth - 2023-02-23 - part 2 - uncharted territory

Chatty crossdresser tries out new depth - 2023-02-23 - part 2 - uncharted territory

xHamster 3 years ago

Femdom Girlfriend Won’t let me take out Plug untill She’s Creampied Trans Cum Interracial BBC Femboy

Femdom Girlfriend Won’t let me take out Plug untill She’s Creampied Trans Cum Interracial BBC Femboy

ShemaleSin 4 years ago

Candid upskirt on forest trail

Candid upskirt on forest trail

WebcamBros 1 month ago

Clitty gets Utterly Rock-Hard from Nip Paws only and then I Stroke

Clitty gets Utterly Rock-Hard from Nip Paws only and then I Stroke

TrannyGem 5 years ago

Exploring Pleasures

Exploring Pleasures

FapHouse 11 months ago

SissyWhiteboi Jes Brinch in white jeans

SissyWhiteboi Jes Brinch in white jeans

xHamster 4 days ago

Sissy Lili assfuck dilatation and wide open with inflatable ass-plug

Sissy Lili assfuck dilatation and wide open with inflatable ass-plug

TrannyGem 3 years ago

Sweat Stiff For honey Foxx's fuck-stick!

Sweat Stiff For honey Foxx's fuck-stick!

TrannyGem 6 years ago

Tranny sodomized fucks colleague at police academy

Tranny sodomized fucks colleague at police academy

Xozilla 7 years ago

Assfuck Sissy Sleepover With Trans Ria Bentley & Lola Crystals

Assfuck Sissy Sleepover With Trans Ria Bentley & Lola Crystals

TrannyGem 2 years ago

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