Training Videos - Trans (87,658)

Sissy Slut Submission: BBC-Lovin' Asshole Stretched by Big, Thick, Veiny Cock

Sissy Slut Submission: BBC-Lovin' Asshole Stretched by Big, Thick, Veiny Cock

XXXShake 1 year ago

sadistic sissy boy Lucy with his bound slave

sadistic sissy boy Lucy with his bound slave

xHamster 1 month ago

Ball pulling, pegging, humiliation & degradation off my pretty sissy bitch Clip 1

Ball pulling, pegging, humiliation & degradation off my pretty sissy bitch Clip 1

xHamster 2 weeks ago

Princess Donna Snatches Good Girls Up In Cages (1 HR With PEE)

Premium HD 1:03:16

Princess Donna Snatches Good Girls Up In Cages (1 HR With PEE)

XVideosRed 1 year ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

HD 0:39 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

Owen & Ronaldo & Patric Private Show

HD 2:00 / 12:16

Owen & Ronaldo & Patric Private Show

Flirt4Free 3 years ago

Amannda Skye Party on Jan 15, 2026

4K 2:00 / 54:59

Amannda Skye Party on Jan 15, 2026

Flirt4Free 1 month ago

Marily Daniela Private Show

HD 2:00 / 22:40

Marily Daniela Private Show

Flirt4Free 2 years ago

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

TrannyGem 4 months ago

Satin Sissy in Chastity Rides Her New Huge Dildo

Satin Sissy in Chastity Rides Her New Huge Dildo

xHamster 1 year ago

Dollars Transexual Adventures - Vignette 1

Dollars Transexual Adventures - Vignette 1

TrannyGem 5 years ago

Trans Girl Tied and Teased

59% HD 1:01 / 13:07

Trans Girl Tied and Teased

FapHouse 1 year ago

Chastity cage play

Chastity cage play

FapHouse 5 years ago

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

BigTitsLust 2 months ago

Greek Cd hubby pegged to assgasm

Greek Cd hubby pegged to assgasm

ShemaleSin 3 years ago

Angela Lelli Private Show

HD 2:00 / 52:49

Angela Lelli Private Show

Flirt4Free 2 years ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 7 years ago

Birthday Bi Party - Part Five - 2 - HD

Birthday Bi Party - Part Five - 2 - HD

Clips4sale 2 years 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

ts vanessa rafaella - cum - exclusive for subscribers

ts vanessa rafaella - cum - exclusive for subscribers

PornBox 4 years ago

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

46% HD 0:10 / 14:09

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

LoyalFans 11 months ago

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

xHamster 1 year ago

Sissy Bride Wedding Day Part 2 Mistress Prepares Her Slut

73% 0:11 / 8:16

Sissy Bride Wedding Day Part 2 Mistress Prepares Her Slut

Clips4sale 2 years ago

Straight Guys Love to be Called Faggots Goddess Vivien Make Me Bi Fantasy with futanari and cuckold talk for pussy free straight guys who crave cock!

4K 0:30 / 11:15

Straight Guys Love to be Called Faggots Goddess Vivien Make Me Bi Fantasy with futanari and cuckold talk for pussy free straight guys who crave cock!

Clips4sale 3 months ago

Extra skinny ladyboy teen trained on BWC

Extra skinny ladyboy teen trained on BWC

DrTuber 1 week ago

Hermaphrodite chick fucks her cis bestie

Hermaphrodite chick fucks her cis bestie

XGroovy 11 months ago

Lady Fyre's School for Boys and Good Sissies

Lady Fyre's School for Boys and Good Sissies

xHamster 1 year ago

”GROOBYGIRLS: Rah Rah Amber Analeise”

”GROOBYGIRLS: Rah Rah Amber Analeise”

429Men 2 weeks ago

Wild Sabrina Members-Only Show

HD 2:00 / 17:25

Wild Sabrina Members-Only Show

Flirt4Free 3 years ago

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

TrannyGem 7 months ago

Damsel SUPREMACY in NAPPIES and PURITY with a hefty ASSFUCKING cork and URINATE

Damsel SUPREMACY in NAPPIES and PURITY with a hefty ASSFUCKING cork and URINATE

TrannyGem 2 years ago

Colombian Boys Private Show

55% HD 2:00 / 11:48

Colombian Boys Private Show

Flirt4Free 6 months ago

Sissy anal training and tight hole gaping so hoooot

Sissy anal training and tight hole gaping so hoooot

xHamster 1 year ago

HOLY COCKMMUNION: Sister Exaltia’s MASSIVE COCK Gospel

HD 0:36 / 10:52

HOLY COCKMMUNION: Sister Exaltia’s MASSIVE COCK Gospel

Clips4sale 1 month ago

Permanent Chastity Humiliation - Obedience Training

Permanent Chastity Humiliation - Obedience Training

xHamster 1 year ago

big fuck-stick BRAZILIAN she-creature TOPS gang-fuck MASS EJACULATION spunk train

big fuck-stick BRAZILIAN she-creature TOPS gang-fuck MASS EJACULATION spunk train

TransTube.tv 7 months ago

TS Carmen Masters Dominants & Gullet Bangs White Servant Twunk…

TS Carmen Masters Dominants & Gullet Bangs White Servant Twunk…

TransTube.tv 1 year ago

Sissy Slut Jessica Bloom Tied up and Used in the Woods

Sissy Slut Jessica Bloom Tied up and Used in the Woods

FapHouse 1 year ago

”Ruined Orgasms By Goddess Bare Feet”

”Ruined Orgasms By Goddess Bare Feet”

Zatube 1 year ago

Must-share moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

Must-share moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

xHamster 4 months ago

Preping my Puppy Loona for her stroking

Preping my Puppy Loona for her stroking

TrannyGem 1 year ago

Gtavanessabitchx the Beautiful Little Whore of the Neighborhood. She Loves Licking the Guys' Cock. Sperm Discharge

Gtavanessabitchx the Beautiful Little Whore of the Neighborhood. She Loves Licking the Guys' Cock. Sperm Discharge

xHamster 3 months ago

Trans humps herself in cooter

Trans humps herself in cooter

TrannyGem 3 years ago

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

xHamster 4 months ago

[metavulgar] - sadomasochism, tractable sissy, diaper torture, diaper lover, medical fetish, sissy training - full version on my patreon page - sissy, joi, cuckold, findom

[metavulgar] - sadomasochism, tractable sissy, diaper torture, diaper lover, medical fetish, sissy training - full version on my patreon page - sissy, joi, cuckold, findom

ShemaleSin 8 months ago

”TS Stunning Aubrey Kate's Seductive Training & Passionate Pleasure”

”TS Stunning Aubrey Kate's Seductive Training & Passionate Pleasure”

ThePornstar 1 year ago

Cute machine fuck for crossdressers with big fake tits and latex mask

Cute machine fuck for crossdressers with big fake tits and latex mask

xHamster 1 year ago

Roommate turns sissy crossdresser into her bitch

Roommate turns sissy crossdresser into her bitch

BigButtHoles 6 months ago

Jhordy & Cody & Archie Private Show

56% HD 2:00 / 9:32

Jhordy & Cody & Archie Private Show

Flirt4Free 3 weeks ago

Bisexual Sluts with TS Kim Wagner

66% 4K 0:26 / 34:47

Bisexual Sluts with TS Kim Wagner

Clips4sale 1 year ago

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Long 29 Min

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Long 29 Min

AbTranny 2 years ago

Florance Wants to Be Loved

Florance Wants to Be Loved

FapHouse 1 year ago

Protection Sissy

Protection Sissy

TrannyGem 4 years ago

I teach my sissy to suck cock

I teach my sissy to suck cock

xHamster 2 months ago

AB021 Three Mistress Extreme Training sissy - BDSM 三女王极限调教人妖艾爷-爆操滴蜡鞭打

AB021 Three Mistress Extreme Training sissy - BDSM 三女王极限调教人妖艾爷-爆操滴蜡鞭打

aShemaleTube 5 years ago

Punished tiny dick by a Futanari Goddess - CBT, FUTA

57% 0:14 / 9:23

Punished tiny dick by a Futanari Goddess - CBT, FUTA

Clips4sale 8 months ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

xHamster 4 years ago

sissypov - becky barr how many times are you going to fuck me everyday porn video

sissypov - becky barr how many times are you going to fuck me everyday porn video

TransDoe 1 year ago

Jasmine Dlight & Hairy Kink Stepmother & Roxxie Sweetheart - Outdoor Fisting Gangbang - the Warmup

69% HD 1:01 / 10:44

Jasmine Dlight & Hairy Kink Stepmother & Roxxie Sweetheart - Outdoor Fisting Gangbang - the Warmup

FapHouse 6 months ago

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

xHamster 1 year ago

Sabrina Smiith Private Show

63% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 6 years ago

Aphrodite Adams Trains You The Foolish Basics

Aphrodite Adams Trains You The Foolish Basics

TrannyGem 4 months ago

Femboy trap bangs herself against a wall and orgasms twice

Femboy trap bangs herself against a wall and orgasms twice

ShemaleSin 3 years ago

Gabriella Bruni Private Show

60% 4K 2:00 / 6:17

Gabriella Bruni Private Show

Flirt4Free 4 months ago

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 3 months ago

Strapon Gag Into Sissy Mouth Asmr Captivating

Strapon Gag Into Sissy Mouth Asmr Captivating

xHamster 4 months ago

Lick Cummies Movie

Lick Cummies Movie

TransTube.tv 1 year ago

Ash Wish to Heal Real Quick to Have Sex with His Boy Friend Blake

Ash Wish to Heal Real Quick to Have Sex with His Boy Friend Blake

FapHouse 11 months ago

Caroline Bella Private Show

Caroline Bella Private Show

Flirt4Free 2 years ago

Jaw-dropping moment from "Crossdresser with fake tits gets worried by the sex machine"

Jaw-dropping moment from "Crossdresser with fake tits gets worried by the sex machine"

xHamster 6 months ago

Sissy femboy is attempting on fresh sumptuous stuff

Sissy femboy is attempting on fresh sumptuous stuff

Gayhub 3 days ago

squirt show

Flirt4Free 3 years ago

Re:Zero Rem Anal training and Blowjob part.2

Re:Zero Rem Anal training and Blowjob part.2

xHamster 3 years ago

I love fucking my husband in the ass

I love fucking my husband in the ass

xHamster 7 months ago

Caroline Bella Private Show

Caroline Bella Private Show

Flirt4Free 2 years ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

Troy Khalil Private Show

66% HD 2:00 / 5:04

Troy Khalil Private Show

Flirt4Free 2 years ago

Sissy Training Doll RyuDoll goes wild with her machine's hard fucking

Sissy Training Doll RyuDoll goes wild with her machine's hard fucking

TrannyMovs 6 months ago

Obedient Puppy Gets Taunted and Pulverized

Obedient Puppy Gets Taunted and Pulverized

TrannyGem 1 year ago

TS Slut milking

73% 0:30 / 14:31

TS Slut milking

Clips4sale 1 year ago

My husband with a small cock fucks me

My husband with a small cock fucks me

xHamster 9 months ago

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

4K 0:11 / 33:28

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

Clips4sale 1 month ago

FemGape Creamy Big Anal Training With Dildo

FemGape Creamy Big Anal Training With Dildo

TubeOn 1 month ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

xHamster 1 month ago

Eat Cum Because You're Gay Jizz Tonguing Commands CEI ft Trans Female dominance

Eat Cum Because You're Gay Jizz Tonguing Commands CEI ft Trans Female dominance

TransTube.tv 1 year ago

Transgender in high heels and lingerie does anal beads

Transgender in high heels and lingerie does anal beads

xHamster 1 year ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 2 years ago

Sophia Loreen Slaps Butt with Enthusiasm

Sophia Loreen Slaps Butt with Enthusiasm

Flirt4Free 4 years ago

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and Transgender Identity

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and Transgender Identity

SortPorn 7 months ago

Sissygasm Tutorial - Sissification with the Lady of Feminization

Sissygasm Tutorial - Sissification with the Lady of Feminization

MatureTubeHere 3 years ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 1 week ago

Breaking Bunni - Goth FemDom trans Gangbang | OverlordJupiter, Lady Vi, Mistress Celene, Dusti Bunni

Premium HD 30:10

Breaking Bunni - Goth FemDom trans Gangbang | OverlordJupiter, Lady Vi, Mistress Celene, Dusti Bunni

Clips4sale 1 year ago

Alizzz Storm Private Show

Alizzz Storm Private Show

Flirt4Free 11 months ago

Be Wendy Summers's Cockslut

69% 0:11 / 12:54

Be Wendy Summers's Cockslut

Clips4sale 2 years ago

Domina instructs you that deepthroating pink cigar isn't bummer if you're using undies - FEMINIZATION ROLEPLAY

Domina instructs you that deepthroating pink cigar isn't bummer if you're using undies - FEMINIZATION ROLEPLAY

HentaiGem 6 months ago

Sissy mega-slut snow bunny Lola getting torn up and creampied by big black cock

Sissy mega-slut snow bunny Lola getting torn up and creampied by big black cock

TrannyGem 3 years ago

Leather Crossdresser Sissy trains his hole to the max

Leather Crossdresser Sissy trains his hole to the max

xHamster 7 months ago

Scott Carterr & Michael Magno Private Show

HD 2:00 / 37:52

Scott Carterr & Michael Magno Private Show

Flirt4Free 2 years ago

Small Femboy Tgirl Fucked by a Strapon Lesbian Femdom

55% 0:39 / 11:55

Small Femboy Tgirl Fucked by a Strapon Lesbian Femdom

FapHouse 2 months ago

TRANSFIXED - Interracial Trans And CIS Lesbian Nurses Have INSANE BAREBACK ORGY To Complete Training

TRANSFIXED - Interracial Trans And CIS Lesbian Nurses Have INSANE BAREBACK ORGY To Complete Training

xHamster 3 years ago

Bi MMF Anal trains c0mp

Bi MMF Anal trains c0mp

Eporner 1 year ago

Cardi B Dazed by MASSSIVE 11” BIG BLACK COCK Trans Fuckpole So YAM-SIZED!!!!

Cardi B Dazed by MASSSIVE 11” BIG BLACK COCK Trans Fuckpole So YAM-SIZED!!!!

TransTube.tv 1 year ago

Super Full Show

56% HD 2:00 / 22:12

Super Full Show

Flirt4Free 1 year ago

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

65% HD 1:01 / 11:20

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

FapHouse 2 years ago

Crossdresser in shiny skirt and stocking rides huge dildos to warm up his anal pussy

Crossdresser in shiny skirt and stocking rides huge dildos to warm up his anal pussy

xHamster 2 years ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 2 years ago

Elvis & Patric & Santiago Private Show

HD 2:00 / 15:49

Elvis & Patric & Santiago Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

4K 2:00 / 24:23

Sophia Loreen Private Show

Flirt4Free 2 months ago

Pussy Slamming!!

Pussy Slamming!!

xHamster 11 months ago

TRANSSEXUAL Sissy BONDAGE & DISCIPLINE Xxx Box Pulverize

TRANSSEXUAL Sissy BONDAGE & DISCIPLINE Xxx Box Pulverize

TrannyGem 5 years ago

korean slim femboy drilled (utter movie on fansly)

korean slim femboy drilled (utter movie on fansly)

Gayhub 1 year ago

Transexual Ol Training Secrets for Ultimate Beauty Transformation Revealed!

Transexual Ol Training Secrets for Ultimate Beauty Transformation Revealed!

JAVHDTube 1 month ago

Sissy molly and her bbc daddy

Sissy molly and her bbc daddy

AbTranny 7 years ago

Femboy Jazii in Anal Training at The Sissy Institute

Femboy Jazii in Anal Training at The Sissy Institute

aShemaleTube 5 years ago

hot dominant goth gives you SPH whilst stroking BBC JOI

77% 0:20 / 5:38

hot dominant goth gives you SPH whilst stroking BBC JOI

Clips4sale 1 year ago

Key moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

Key moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

xHamster 4 months ago

Marily Daniela Private Show

Marily Daniela Private Show

Flirt4Free 2 years ago

Sissy trans get boink my a turkish stud

Sissy trans get boink my a turkish stud

TransTube.tv 9 months ago

My sissy bitch dressed up and pegged in his tight hole

My sissy bitch dressed up and pegged in his tight hole

xHamster 2 years ago

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