Training Videos - Trans (87,305)

Isabella Pearson Private Show

HD 2:00 / 37:56

Isabella Pearson Private Show

Flirt4Free 2 years ago

Sissy Play

xHamster 5 months ago

Ultra-Cute Chinese Crossdresser 25, looks so great with the fake penis in my anal invasion

Ultra-Cute Chinese Crossdresser 25, looks so great with the fake penis in my anal invasion

TrannyGem 3 years ago

Cute Ts Using Dildo Machine

Cute Ts Using Dildo Machine

Sheshaft 1 month ago

Tsumugi Narita - Masochistic Cosplayers, Training Photoshoot 2

Tsumugi Narita - Masochistic Cosplayers, Training Photoshoot 2

PornFreeNow 6 months ago

Sissy Listens as I Take His Marriage by Findom Goaldigger

Sissy Listens as I Take His Marriage by Findom Goaldigger

xHamster 4 months ago

Trans doll TSAVIVA self fulfillment ass fucking & cum shot teaser

Trans doll TSAVIVA self fulfillment ass fucking & cum shot teaser

Transvids.tv 8 months ago

sissy horse cock training

sissy horse cock training

aShemaleTube 5 years ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

xHamster 2 months ago

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

66% HD 0:39 / 8:31

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

FapHouse 10 months ago

Pumping Crimson Good-Sized Long Dragon Snake Faux-Cock Deep in my Demolished Booty

Pumping Crimson Good-Sized Long Dragon Snake Faux-Cock Deep in my Demolished Booty

GayCK 4 years ago

Crossdresser Anal Dildo Fun Sissy Anal Training Huge Dildo in Ass

Crossdresser Anal Dildo Fun Sissy Anal Training Huge Dildo in Ass

xHamster 2 years ago

Sissy Dani training her gap with BBC

Sissy Dani training her gap with BBC

ShemaleSin 1 year ago

20 Inches Deep! Sissy Maid Extreme Deep Anal Training Jessica Bloom

20 Inches Deep! Sissy Maid Extreme Deep Anal Training Jessica Bloom

BallsAndBoobs 10 months ago

Florance Wants to Be Loved

55% HD 0:39 / 8:46

Florance Wants to Be Loved

FapHouse 1 year ago

sissies don't need to breed: beg futa step-mommy to castrate you - full video on Veggiebabyy Manyvids

sissies don't need to breed: beg futa step-mommy to castrate you - full video on Veggiebabyy Manyvids

xHamster 2 months ago

sissy sonya on gynochair banged by banging machine

sissy sonya on gynochair banged by banging machine

ShemaleSin 2 years ago

Janet Discloses Her True Raunchy Identity

Janet Discloses Her True Raunchy Identity

ShemaleSin 11 months ago

SISSY Buttfuck Instructing by SPANDEX Domme

SISSY Buttfuck Instructing by SPANDEX Domme

TrannyGem 2 months ago

A super-sexy fun time

A super-sexy fun time

TransTube.tv 1 year ago

Rise of the Queen : Unveiling the Path to Drag Domination

58% HD 0:10 / 15:32

Rise of the Queen : Unveiling the Path to Drag Domination

LoyalFans 11 months ago

Trans Girl *** Orgasm

61% HD 1:01 / 19:44

Trans Girl *** Orgasm

FapHouse 1 year ago

Your Sissy fantasy come True - Woman POINT OF VIEW blowage - Roleplay

Your Sissy fantasy come True - Woman POINT OF VIEW blowage - Roleplay

TrannyGem 1 year ago

Plugged and Vexed

61% HD 1:01 / 10:50

Plugged and Vexed

FapHouse 3 years ago

Reina Hanno Stretches Anal with Jelly Dildo and Cums

HD 0:39 / 24:49

Reina Hanno Stretches Anal with Jelly Dildo and Cums

FapHouse 1 month ago

Donk donk-butt-plug training Pt1 Trying 3 sizes of plugs for the very first time. My twat is slobbering.

Donk donk-butt-plug training Pt1 Trying 3 sizes of plugs for the very first time. My twat is slobbering.

TransTube.tv 1 year ago

Sexy Shemale Rayssa Pereira Porn Pov Trains in Hardcore Anal Action

Sexy Shemale Rayssa Pereira Porn Pov Trains in Hardcore Anal Action

TrannyMovs 2 weeks ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

xHamster 4 years ago

Smoke Sub to a Shemale

Smoke Sub to a Shemale

TrannyGem 1 year ago

Painful ruined orgasm cbt for my bondaged sub sissy whore

Painful ruined orgasm cbt for my bondaged sub sissy whore

Tranny.one 4 years ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 16:34

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 week ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3

xHamster 2 months ago

HANKEYs TOYS COMPILATION!!

Premium HD 20:08

HANKEYs TOYS COMPILATION!!

XVideosRed 1 year ago

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

xHamster 5 months ago

Master & Ithan & Aleex Private Show

62% HD 2:00 / 4:00:00+

Master & Ithan & Aleex Private Show

Flirt4Free 8 months ago

sissy serah being pimped out by wordy dom big black cock part 1

sissy serah being pimped out by wordy dom big black cock part 1

TrannyGem 2 years ago

”Sexy Transgender Venus Lux trains newcomer Javier LoveTongue with her raw meat”

”Sexy Transgender Venus Lux trains newcomer Javier LoveTongue with her raw meat”

LesbianBliss 1 month 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

AdelphaPerri teaching her cock-squeezing pinky rectum with anal invasion beads

AdelphaPerri teaching her cock-squeezing pinky rectum with anal invasion beads

TrannyGem 8 months 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

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

Nylon whore Dagmar321 jerks off and squirts

Nylon whore Dagmar321 jerks off and squirts

xHamster 3 years ago

Brazilian cuck instructed to play with dildo and vibrator

Brazilian cuck instructed to play with dildo and vibrator

xHamster 2 years ago

AB110 Fresh Yr Furniture: Human Table deep throat,cum shot,dumping (Asian and English subtitles)

AB110 Fresh Yr Furniture: Human Table deep throat,cum shot,dumping (Asian and English subtitles)

TrannyGem 2 years ago

Dollars Transexual Adventures - Vignette 1

Dollars Transexual Adventures - Vignette 1

TrannyGem 5 years ago

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

Marily Daniela Private Show

HD 2:00 / 22:40

Marily Daniela Private Show

Flirt4Free 2 years ago

Satin Sissy in Chastity Rides Her New Huge Dildo

Satin Sissy in Chastity Rides Her New Huge Dildo

xHamster 1 year ago

Amannda Skye Party on Jan 15, 2026

4K 2:00 / 54:59

Amannda Skye Party on Jan 15, 2026

Flirt4Free 1 month 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

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

FapHouse 2 years ago

Chastity cage play

Chastity cage play

FapHouse 5 years ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 7 years ago

Training a cute twink how to get fuck

Training a cute twink how to get fuck

Tranny.one 4 years ago

Greek Cd hubby pegged to assgasm

Greek Cd hubby pegged to assgasm

ShemaleSin 3 years ago

ts vanessa rafaella - cum - exclusive for subscribers

ts vanessa rafaella - cum - exclusive for subscribers

PornBox 4 years ago

Birthday Bi Party - Part Five - 2 - HD

Birthday Bi Party - Part Five - 2 - HD

Clips4sale 2 years ago

Corporate Training - 3D Tranny Manga Animation

Corporate Training - 3D Tranny Manga Animation

Dafreeporn 2 years ago

Tffany Sturban Anal Training With Big Dildo

Tffany Sturban Anal Training With Big Dildo

VipTube 1 month ago

Lady Fyre's School for Boys and Good Sissies

Lady Fyre's School for Boys and Good Sissies

xHamster 1 year ago

”Safety First - Roman Todd, Jade Venus”

”Safety First - Roman Todd, Jade Venus”

TransHero 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

Instructional Sissy Slut Training On How To Find and SuckMore Guys

64% 4K 0:27 / 21:54

Instructional Sissy Slut Training On How To Find and SuckMore Guys

Clips4sale 1 year 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

Hermaphrodite chick fucks her cis bestie

Hermaphrodite chick fucks her cis bestie

XGroovy 11 months ago

Extra skinny ladyboy teen trained on BWC

Extra skinny ladyboy teen trained on BWC

DrTuber 1 week 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

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

Lillith xoxo Anal Training With Dildo

Lillith xoxo Anal Training With Dildo

IcePorn 5 days 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

Sissy Deepthroat Training Time!

Sissy Deepthroat Training Time!

xHamster 3 years ago

Wild Sabrina Members-Only Show

HD 2:00 / 17:25

Wild Sabrina Members-Only Show

Flirt4Free 3 years ago

Extended Cut of Bubble but Trans Girl in Dva Cosplay Blacked by BBC Creampie and Cum Farts

Extended Cut of Bubble but Trans Girl in Dva Cosplay Blacked by BBC Creampie and Cum Farts

xHamster 5 months 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

”GROOBYGIRLS: Rah Rah Amber Analeise”

”GROOBYGIRLS: Rah Rah Amber Analeise”

429Men 2 weeks ago

Panty Sissy big toy anal gaping prolapse loose hole rosebud

Panty Sissy big toy anal gaping prolapse loose hole rosebud

xHamster 4 years ago

Public Assfucking Fake Penis 1 (My Homework)

Public Assfucking Fake Penis 1 (My Homework)

TrannyGem 1 year ago

TS Carmen Masters Dominants & Gullet Bangs White Servant Twunk…

TS Carmen Masters Dominants & Gullet Bangs White Servant Twunk…

TransTube.tv 1 year ago

”Ruined Orgasms By Goddess Bare Feet”

”Ruined Orgasms By Goddess Bare Feet”

Zatube 1 year ago

Permanent Chastity Humiliation - Obedience Training

Permanent Chastity Humiliation - Obedience Training

xHamster 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 week ago

Sissy anal training and tight hole gaping so hoooot

Sissy anal training and tight hole gaping so hoooot

xHamster 1 year ago

Instruction from the trainer No 27 Exposure walk

Instruction from the trainer No 27 Exposure walk

xHamster 3 months ago

FemGape Creamy Big Anal Training With Dildo

FemGape Creamy Big Anal Training With Dildo

TubeOn 1 month ago

Cute Blonde Trans Girl Cum Farting Anal Sex

Cute Blonde Trans Girl Cum Farting Anal Sex

xHamster 4 days ago

submissive tgirl suffers mindfuck electric shock timer game

57% HD 0:28 / 24:56

submissive tgirl suffers mindfuck electric shock timer game

PornBox 11 months 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

Sissy Maid Is Taught Proper Manners

Sissy Maid Is Taught Proper Manners

FapHouse 3 months ago

Trans humps herself in cooter

Trans humps herself in cooter

TrannyGem 3 years ago

Huge ass tranny gaping

Huge ass tranny gaping

xHamster 1 year ago

Preping my Puppy Loona for her stroking

Preping my Puppy Loona for her stroking

TrannyGem 1 year ago

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

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

ThePornstar 1 year 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

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

Lilly Benz transforms you into a hot and horny girl and fucks you hard in sissification POV

Lilly Benz transforms you into a hot and horny girl and fucks you hard in sissification POV

TrannyMovs 4 months ago

Jhordy & Cody & Archie Private Show

56% HD 2:00 / 9:32

Jhordy & Cody & Archie Private Show

Flirt4Free 3 weeks ago

Roommate turns sissy crossdresser into her bitch

Roommate turns sissy crossdresser into her bitch

BigButtHoles 6 months ago

Bisexual Sluts with TS Kim Wagner

66% 4K 0:26 / 34:47

Bisexual Sluts with TS Kim Wagner

Clips4sale 1 year 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

Troy Khalil Private Show

HD 2:00 / 28:06

Troy Khalil Private Show

Flirt4Free 2 years ago

I teach my sissy to suck cock

I teach my sissy to suck cock

xHamster 2 months ago

Amateur couple in search for second to fuck her pussy

Amateur couple in search for second to fuck her pussy

xHamster 3 years ago

Cosplay Sissification KDA Evelynn Akali Leauge of Legends TEASER OmankoVivi

Cosplay Sissification KDA Evelynn Akali Leauge of Legends TEASER OmankoVivi

Pornfact 1 week 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

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

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

Protection Sissy

Protection Sissy

TrannyGem 4 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

Florance Wants to Be Loved

Florance Wants to Be Loved

FapHouse 1 year ago

Ohmibod Play

Flirt4Free 7 years ago

Strapon Gag Into Sissy Mouth Asmr Captivating

Strapon Gag Into Sissy Mouth Asmr Captivating

xHamster 4 months 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

Femboy trap bangs herself against a wall and orgasms twice

Femboy trap bangs herself against a wall and orgasms twice

ShemaleSin 3 years ago

Sabrina Smiith Private Show

63% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Kira caught during self-bondage

Kira caught during self-bondage

xHamster 5 months ago

Mrhankeys CLIP-CLOP 4XL first time

Mrhankeys CLIP-CLOP 4XL first time

xHamster 2 years ago

Rosita Jimenez & Nikki Martinz Private Show

61% HD 2:00 / 21:50

Rosita Jimenez & Nikki Martinz Private Show

Flirt4Free 1 year ago

Aphrodite Adams Trains You The Foolish Basics

Aphrodite Adams Trains You The Foolish Basics

TrannyGem 4 months 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”

Fapnow 2 months ago

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 3 months ago

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