Training Videos - Trans (88,156)

Rage vs Bea | 75kg vs 110kg |mp4|HD|

HD 0:55 / 17:48

Rage vs Bea | 75kg vs 110kg |mp4|HD|

Clips4sale 4 years ago

Be a Sissy Wench *jaymie Jameson Sissy Caption*

Be a Sissy Wench *jaymie Jameson Sissy Caption*

ShemaleSin 4 years ago

sissypov - aliza breeze sissy slut loves dick

sissypov - aliza breeze sissy slut loves dick

TransDoe 2 years ago

Sub Torment 6

Clips4sale 2 years ago

milfycalla – red dressed toy queen plays with pussy & throat masturbators - fetish solo play 293

HD 0:30 / 14:52

milfycalla – red dressed toy queen plays with pussy & throat masturbators - fetish solo play 293

PornBox 7 months ago

Dripping Sissy Slut

43% 0:24 / 16:20

Dripping Sissy Slut

Clips4sale 3 years ago

Step-Mom Turns Step-Son into Step-Daughter

40% 0:41 / 3:54

Step-Mom Turns Step-Son into Step-Daughter

Clips4sale 3 years ago

4K - Lusty Shower Vol 21 - Golden Strawberry Month # 6

66% 4K 0:09 / 43:48

4K - Lusty Shower Vol 21 - Golden Strawberry Month # 6

Clips4sale 4 months ago

Milena Lynn Private Show

HD 2:00 / 31:48

Milena Lynn Private Show

Flirt4Free 2 years ago

Public humiliation for sissy bitch - Miss Eva Ray - MP4 HD

Public humiliation for sissy bitch - Miss Eva Ray - MP4 HD

Clips4sale 1 year ago

Browser History - Alexa Hoyt and Sorceress Morgana Soles Trans Woman Handjob With Religious Humiliation

61% HD 0:10 / 5:59

Browser History - Alexa Hoyt and Sorceress Morgana Soles Trans Woman Handjob With Religious Humiliation

LoyalFans 2 months ago

anal casting of the submissive thai ladyboy

65% 0:44 / 24:39

anal casting of the submissive thai ladyboy

AnalVids 1 year ago

Hanna Ven Private Show

Hanna Ven Private Show

Flirt4Free 2 years ago

Your first Sissygasm

46% 0:15 / 9:04

Your first Sissygasm

Clips4sale 2 years ago

Three tops and two subs on a wicked anal orgy (1080 EN-sub)

HD 0:26 / 21:19

Three tops and two subs on a wicked anal orgy (1080 EN-sub)

Clips4sale 2 years ago

Addonis Smith & Huber Nicols Private Show

HD 2:00 / 11:18

Addonis Smith & Huber Nicols Private Show

Flirt4Free 1 year ago

Stoner Girl

TrannyGem 4 months ago

”Redhead ebony trainee ass pumping plugged”

”Redhead ebony trainee ass pumping plugged”

TransHero 2 months ago

Army Sergeant Dommes Tied Recruit With Lady Cock Fucking And Face Sitting Training

Army Sergeant Dommes Tied Recruit With Lady Cock Fucking And Face Sitting Training

Eporner 2 months ago

Anal foams over machine for sexy crossdresser

Anal foams over machine for sexy crossdresser

xHamster 5 months ago

HRT: Hormone Reduction Transformation

65% 0:33 / 15:00

HRT: Hormone Reduction Transformation

Clips4sale 6 months ago

Welcome to the Cock Worship Cult

HD 0:30 / 35:05

Welcome to the Cock Worship Cult

Clips4sale 1 month ago

Trans Goddess Pummeling Machine

Trans Goddess Pummeling Machine

TrannyGem 3 months ago

Isabella Pearson Private Show

HD 2:00 / 37:56

Isabella Pearson Private Show

Flirt4Free 2 years ago

Lanna Rouse Private Show

Lanna Rouse Private Show

Flirt4Free 2 years ago

SissyOlsen get Feminized by her Verbal Top Dom BBC

SissyOlsen get Feminized by her Verbal Top Dom BBC

aShemaleTube 2 years ago

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

TrannyGem 1 year ago

Face Slapping Bundle

63% 0:26 / 13:38

Face Slapping Bundle

Clips4sale 1 year ago

PRETEND YOU'RE STRAIGHT

PRETEND YOU'RE STRAIGHT

Clips4sale 2 years ago

A hotwife on the beach

A hotwife on the beach

xHamster 1 year ago

Anal Pumped Sissy Ass Feels so Good

Anal Pumped Sissy Ass Feels so Good

xHamster 5 months ago

Sissy Medical Exam (Part 1)

Sissy Medical Exam (Part 1)

Clips4sale 1 year ago

Trans PAWG trains her butt for a massive sex toy

Trans PAWG trains her butt for a massive sex toy

ShemaleSin 1 year ago

Go Gay For My Girl-Cock (4KUHD MP4)

67% HD 0:32 / 15:55

Go Gay For My Girl-Cock (4KUHD MP4)

Clips4sale 1 year ago

Mommy's Pretty Dildo Sissy JOI

65% 0:15 / 14:13

Mommy's Pretty Dildo Sissy JOI

Clips4sale 3 years ago

Celeste Darell Private Show

HD 2:00 / 15:32

Celeste Darell Private Show

Flirt4Free 2 years ago

Spanks

Flirt4Free 1 year ago

Daily cross dresser training ruined climax joi with s1monreilly

Daily cross dresser training ruined climax joi with s1monreilly

ManPorn 2 years ago

Petite Allumeuse En Foret. Cumslut P U B L I C

Petite Allumeuse En Foret. Cumslut P U B L I C

xHamster 8 months ago

Slut Milking (1080p)

54% HD 0:12 / 15:15

Slut Milking (1080p)

Clips4sale 1 year ago

Sissy gets her holes stuffed in gangbang

Sissy gets her holes stuffed in gangbang

Clips4sale 1 year ago

Ali Da Reaper spreading my gullet

Ali Da Reaper spreading my gullet

TrannyGem 3 years ago

Hanna Ven Private Show

HD 2:00 / 10:44

Hanna Ven Private Show

Flirt4Free 1 year ago

Hot blue Skin Avatar anal training

xHamster 2 years ago

You dont want to be Straight anymore

68% 0:37 / 12:06

You dont want to be Straight anymore

Clips4sale 10 months ago

Extreme Boot Slut Stage 1 (MP4)

Extreme Boot Slut Stage 1 (MP4)

Clips4sale 6 months ago

Nastya Blue Private Show

63% HD 2:00 / 4:22

Nastya Blue Private Show

Flirt4Free 1 year ago

Marianna & Ian Private Show

Marianna & Ian Private Show

Flirt4Free 2 years ago

”Stepdaughter Training with Billy Glide & Kelly Surfer”

”Stepdaughter Training with Billy Glide & Kelly Surfer”

TransHero 3 months ago

BRAZILIAN TRANS SLAVE DEEPTHROAT BLOWJOB

BRAZILIAN TRANS SLAVE DEEPTHROAT BLOWJOB

XVideos 2 months ago

Lick My Futa Cum Feet

59% HD 0:11 / 6:56

Lick My Futa Cum Feet

Clips4sale 3 years ago

Shemale Cumshot Compilation: No Hands Sissy Training

Shemale Cumshot Compilation: No Hands Sissy Training

Jizzberry 3 years ago

Those tiny orgasms

Those tiny orgasms

xHamster 3 years ago

Asian femboy re:zero rem cosplay anal training and blowjob - part 8

Asian femboy re:zero rem cosplay anal training and blowjob - part 8

XXXShemalePorn 2 years ago

Customised Vod Video for a Client Book Your Show Today

Customised Vod Video for a Client Book Your Show Today

xHamster 7 months ago

Bewitched Into My Bitch (Mind Fuck, Mesmerize, JOI)

Bewitched Into My Bitch (Mind Fuck, Mesmerize, JOI)

Clips4sale 3 years ago

Smell my stinky futanari dick - POV

Smell my stinky futanari dick - POV

Clips4sale 3 years ago

Pretty Girl Feminization - Training Femme Sluts! - 4K MP4

55% 4K 0:39 / 11:34

Pretty Girl Feminization - Training Femme Sluts! - 4K MP4

Clips4sale 9 months ago

Daniela Beltran Private Show

HD 2:00 / 10:23

Daniela Beltran Private Show

Flirt4Free 3 years ago

Chloe Cruzz & Michel Taylor Private Show

Chloe Cruzz & Michel Taylor Private Show

Flirt4Free 1 year ago

THE RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE hd

4K 0:58 / 40:01

THE RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE hd

Clips4sale 5 months ago

Knotting my butt with a big blue wolf dildo~

Knotting my butt with a big blue wolf dildo~

XVideos 3 years ago

Master Trains His Sissy In Chastity He Uses Her Mouth And Her Liking Making Her A Real Whore Shemal

Master Trains His Sissy In Chastity He Uses Her Mouth And Her Liking Making Her A Real Whore Shemal

aShemaleTube 1 month ago

Hot Shemale on the Fuck Yeah Machine - Red Pvc & Giant Dildo Depth Training Extreme Deep Anal

Hot Shemale on the Fuck Yeah Machine - Red Pvc & Giant Dildo Depth Training Extreme Deep Anal

xHamster 1 month ago

Humiliation 269

Humiliation 269

Clips4sale 2 weeks ago

Andrea & Taty Private Show

HD 2:00 / 20:55

Andrea & Taty Private Show

Flirt4Free 2 months ago

Hyperventilation aroma Futa worship - JOI

66% 0:13 / 9:59

Hyperventilation aroma Futa worship - JOI

Clips4sale 2 years ago

Ab067 Foot Worship - Femdom Training Two Sissy 恋足调教-女装奴化训练 - Abby Kitty

Ab067 Foot Worship - Femdom Training Two Sissy 恋足调教-女装奴化训练 - Abby Kitty

PornUse 4 months ago

Kinky Sub Girl Worships Sabrina Valentine's Feet (HD1080 MP4)

Kinky Sub Girl Worships Sabrina Valentine's Feet (HD1080 MP4)

Clips4sale 5 months ago

o mestre rasgou o cu da submissa e usou ela como mictorio

66% 5:46 / 17:34

o mestre rasgou o cu da submissa e usou ela como mictorio

PornBox 5 months ago

Beautiful 18 year old tgirl gets horny in her room when no one is home.

Beautiful 18 year old tgirl gets horny in her room when no one is home.

XVideos 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 month ago

THE MISTRESS AND HER LITTLE SLUT (wmv) FULLVERSION

THE MISTRESS AND HER LITTLE SLUT (wmv) FULLVERSION

Clips4sale 3 years ago

On the Beach Sissy Fuck

On the Beach Sissy Fuck

Clips4sale 2 years ago

Sissy training asspussy slowly on machine in chastity

Sissy training asspussy slowly on machine in chastity

xHamster 3 years ago

Dimitri Caruso Private Show

HD 2:00 / 19:38

Dimitri Caruso Private Show

Flirt4Free 3 years ago

You Want Big Black Cocks

You Want Big Black Cocks

Clips4sale 6 months ago

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

ShemaleSin 1 year ago

You've Got That Magic !!! With Dee Angels

You've Got That Magic !!! With Dee Angels

xHamster 1 year ago

Zoe Rous Private Show

57% 4K 2:00 / 12:15

Zoe Rous Private Show

Flirt4Free 7 months ago

Sissy Slut Bitch Cleaning Goddess Kitchen

HD 0:21 / 11:34

Sissy Slut Bitch Cleaning Goddess Kitchen

Clips4sale 3 years ago

8K - Dark Strawberry Bunny's Naughty Cummy Day + Bonus ~Ichigo x Strawberry Festival~

4K 0:19 / 40:16

8K - Dark Strawberry Bunny's Naughty Cummy Day + Bonus ~Ichigo x Strawberry Festival~

Clips4sale 1 month ago

Latex Spit Roast with Trans Domme

71% 0:24 / 24:22

Latex Spit Roast with Trans Domme

Clips4sale 2 years ago

Active, passive and hawt

Active, passive and hawt

ShemaleSin 9 months ago

Andrea & Taty Private Show

Andrea & Taty Private Show

Flirt4Free 3 weeks ago

you were meant to be a girl: loving feminization and pov bj - SD wmv

you were meant to be a girl: loving feminization and pov bj - SD wmv

Clips4sale 9 months ago

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - SD

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - SD

Clips4sale 1 year ago

Vanessa Blue Strap On Toilet Training POV VBBC

Vanessa Blue Strap On Toilet Training POV VBBC

AbTranny 6 years ago

NO MERCY NON STOP SHEMALE FETISHTRANSEXUAL HARDCORE ON SUB SLAVE COCKSUCKER P6

63% 0:18 / 11:47

NO MERCY NON STOP SHEMALE FETISHTRANSEXUAL HARDCORE ON SUB SLAVE COCKSUCKER P6

Clips4sale 3 years ago

Amber Burnt Private Show

HD 2:00 / 12:16

Amber Burnt Private Show

Flirt4Free 2 years ago

Ruth & Carlaa Private Show

Ruth & Carlaa Private Show

Flirt4Free 1 year ago

Aromatic shemale paradise - Task

Aromatic shemale paradise - Task

Clips4sale 3 years ago

Mistress Lady Renee - Used condoms for sissy to clean - mp4

63% 0:15 / 9:31

Mistress Lady Renee - Used condoms for sissy to clean - mp4

Clips4sale 1 year ago

What Did He Do To You Cuck (1080 HD)

50% HD 0:11 / 9:48

What Did He Do To You Cuck (1080 HD)

Clips4sale 4 years ago

Charlie & Eduard Private Show

HD 2:00 / 18:05

Charlie & Eduard Private Show

Flirt4Free 3 years ago

Mey Evanson Private Show

63% HD 2:00 / 27:24

Mey Evanson Private Show

Flirt4Free 4 years ago

Trans Sissy Bitch Milks her jock in hot cow underware, Full movie on Onlyfans @britneyxxxb

Trans Sissy Bitch Milks her jock in hot cow underware, Full movie on Onlyfans @britneyxxxb

ShemaleSin 4 years ago

Jinx Make Spanks in Doggy Pose

Jinx Make Spanks in Doggy Pose

Flirt4Free 11 months ago

Amannda Skye Party on Jan 1, 2026

4K 2:00 / 35:55

Amannda Skye Party on Jan 1, 2026

Flirt4Free 2 months ago

All that throat training pays off : facefucking gorgeous transwife Melody

All that throat training pays off : facefucking gorgeous transwife Melody

XVideos 1 year ago

European Model, Brutus Plays with His Dick

HD 2:00 / 13:07

European Model, Brutus Plays with His Dick

Flirt4Free 9 years ago

Sissy Lumps

XVideos 8 years ago

Pretty Elisha Private Show

55% HD 2:00 / 5:39

Pretty Elisha Private Show

Flirt4Free 1 year ago

femboy maidboy and sissy maidgirl breeding (tough assfucking innocence plow with cassie coyote!)

femboy maidboy and sissy maidgirl breeding (tough assfucking innocence plow with cassie coyote!)

Transvids.tv 8 months ago

AB026 Mistress training abby by wooden pony ,anal plug -cum TS女优艾比绳缚拘束骑乘木马电动肛塞被Maya女王调教高潮喷发-BDSM

AB026 Mistress training abby by wooden pony ,anal plug -cum TS女优艾比绳缚拘束骑乘木马电动肛塞被Maya女王调教高潮喷发-BDSM

aShemaleTube 5 years ago

You are Diaper Sissy Step-Sisters

4K 0:30 / 16:30

You are Diaper Sissy Step-Sisters

Clips4sale 9 months ago

Hellish Aroma Trapdoor

62% 0:41 / 9:03

Hellish Aroma Trapdoor

Clips4sale 6 months ago

Ftm Soldier Receives Humiliating Pussy Discipline Training

60% HD 0:30 / 15:06

Ftm Soldier Receives Humiliating Pussy Discipline Training

Clips4sale 1 year ago

Intense Anal Training Session with Huge Toys & POV Sissygasm - SD

Intense Anal Training Session with Huge Toys & POV Sissygasm - SD

Clips4sale 1 year ago

Amannda Skye Party on Jan 14, 2026

4K 2:00 / 56:27

Amannda Skye Party on Jan 14, 2026

Flirt4Free 2 months ago

Eid Special Anal Training Day

Eid Special Anal Training Day

xHamster 11 months ago

8 Sissygams for Mistress, 1 Orgasm for Sissy

HD 0:39 / 31:06

8 Sissygams for Mistress, 1 Orgasm for Sissy

FapHouse 1 year ago

Stepmom's Panty Sissy

60% 0:11 / 13:28

Stepmom's Panty Sissy

Clips4sale 2 years ago

Sissyboy Is whipped and pegged and humiliated by goddes

63% HD 0:23 / 19:33

Sissyboy Is whipped and pegged and humiliated by goddes

Clips4sale 2 years ago

Afternoon Anal Training

Afternoon Anal Training

APClips 1 year ago

Introduction to Sissy Academy (AVI)

Introduction to Sissy Academy (AVI)

Clips4sale 2 years ago

Corina Streignard Private Show

62% HD 2:00 / 7:41

Corina Streignard Private Show

Flirt4Free 3 years ago

Your Roommate is a Sissy for Big Black Cock

37% 4K 0:28 / 12:04

Your Roommate is a Sissy for Big Black Cock

Clips4sale 1 year ago

Hanna Ven Private Show

Hanna Ven Private Show

Flirt4Free 1 year ago

New Silikon breast, cock & ball whipping and than fisting

New Silikon breast, cock & ball whipping and than fisting

xHamster 7 months ago

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