Training Videos - Trans (88,395)

Sissy Female Supremacist

HD 0:29 / 10:02

Sissy Female Supremacist

Clips4sale 2 years ago

Camelia Intense Anal Training With Anal Destruction

Camelia Intense Anal Training With Anal Destruction

getTranny 1 year ago

Big enema for vinyl maid (wmv)

Big enema for vinyl maid (wmv)

Clips4sale 4 years ago

Dreamscape Sissy training

Dreamscape Sissy training

FetishShrine 2 years ago

Zayra Ross Private Show

4K 2:00 / 12:22

Zayra Ross Private Show

Flirt4Free 2 months ago

Brutus Flexes,jerks,shows Ass,balls on Sofa,standing Up,full Worship

HD 2:00 / 20:57

Brutus Flexes,jerks,shows Ass,balls on Sofa,standing Up,full Worship

Flirt4Free 8 years ago

Sissy Training Compilation

43% 0:20 / 25:12

Sissy Training Compilation

Clips4sale 3 years ago

Domme Tgirl rides BBC till he nuts then makes him eat it

Domme Tgirl rides BBC till he nuts then makes him eat it

Clips4sale 1 year ago

Closet Sissy, gets Caged & Tag Teamed With My Trans BFF (1080 MP4)

HD 0:29 / 10:38

Closet Sissy, gets Caged & Tag Teamed With My Trans BFF (1080 MP4)

Clips4sale 2 years ago

The Power of My COCK

67% HD 0:29 / 9:22

The Power of My COCK

Clips4sale 1 year ago

Cd gets fucked until anal orgasm and cumshot

Cd gets fucked until anal orgasm and cumshot

xHamster 11 months ago

Destiny Spencer Private Show

Destiny Spencer Private Show

Flirt4Free 3 years ago

Solo have fun from the thicc Jordyn Jett

Solo have fun from the thicc Jordyn Jett

TrannyGem 2 years ago

Sissy in Burqa: Height Humiliation and Domination - Candid Session with Goddess Marcy

56% HD 0:25 / 10:57

Sissy in Burqa: Height Humiliation and Domination - Candid Session with Goddess Marcy

Clips4sale 1 year ago

Auctioned Slaves fresh Home

Auctioned Slaves fresh Home

ShemaleSin 4 years ago

huge fucking session and cum like a sissy slut - sissy captions

huge fucking session and cum like a sissy slut - sissy captions

aShemaleTube 9 months ago

Keisy Royce Private Show

HD 2:00 / 11:37

Keisy Royce Private Show

Flirt4Free 2 years ago

Margaux Fox Private Show

Margaux Fox Private Show

Flirt4Free 8 months ago

Kendra James and Dixie Lynn: Batwoman begs for Harleys massive cock! 720 mp4

Premium HD 34:28

Kendra James and Dixie Lynn: Batwoman begs for Harleys massive cock! 720 mp4

Clips4sale 3 years ago

SUBMISSIVE TRANS LADYBOY ANAL CASTING, FISTING & SLAVE TRAINING

62% HD 0:24 / 45:15

SUBMISSIVE TRANS LADYBOY ANAL CASTING, FISTING & SLAVE TRAINING

Clips4sale 10 months ago

Hanna Ven Private Show

HD 2:00 / 14:41

Hanna Ven Private Show

Flirt4Free 1 year ago

Training to Getting Comfort With Butt Touch

Training to Getting Comfort With Butt Touch

xHamster 11 months ago

THE RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE

59% 4K 0:58 / 40:01

THE RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE

Clips4sale 6 months ago

Cumming with a vibe closeup in my fullups

55% HD 0:29 / 9:10

Cumming with a vibe closeup in my fullups

Clips4sale 1 year ago

Self-training No. 96: Exhibitionist Walk with Visible Used Sanitary Napkin

HD 0:39 / 25:14

Self-training No. 96: Exhibitionist Walk with Visible Used Sanitary Napkin

FapHouse 1 month ago

Sissy's Surprise Double Feature: An Audio Fantasy of Submission

44% 0:30 / 17:07

Sissy's Surprise Double Feature: An Audio Fantasy of Submission

Clips4sale 1 year ago

Locked, Gagged, and Ball Slapped to Orgasm

HD 0:10 / 22:18

Locked, Gagged, and Ball Slapped to Orgasm

Clips4sale 4 years ago

My husband became a sissy in a chastity cage

My husband became a sissy in a chastity cage

xHamster 2 years ago

Amannda Skye Party on Dec 15, 2025 - Part 3

4K 2:00 / 54:48

Amannda Skye Party on Dec 15, 2025 - Part 3

Flirt4Free 3 months ago

AB099 Became Femdom's Masturbation Cup -training instructions -成为女王的飞机杯-调教指令言语羞辱-射精

AB099 Became Femdom's Masturbation Cup -training instructions -成为女王的飞机杯-调教指令言语羞辱-射精

aShemaleTube 2 years ago

My big sissy bitch get's punished

My big sissy bitch get's punished

Clips4sale 2 years ago

Goddess Rhea Thorn commands me to worship her feet, massage, kissing, sucking, licking - genital crushing and footjob

Goddess Rhea Thorn commands me to worship her feet, massage, kissing, sucking, licking - genital crushing and footjob

Clips4sale 1 year ago

Hanna Ven Private Show

HD 2:00 / 10:13

Hanna Ven Private Show

Flirt4Free 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

Kelly's Crossdressing Slut (MP4)

Kelly's Crossdressing Slut (MP4)

Clips4sale 7 months ago

Femboy opens up her lil bootie

Femboy opens up her lil bootie

TrannyGem 2 years ago

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

ShemaleSin 2 years ago

Double foot fisting with Aveena

64% HD 0:28 / 41:07

Double foot fisting with Aveena

Clips4sale 3 years ago

Thick Step Mom Does Horrible Things to Her Step Sons! Arya Grander

Thick Step Mom Does Horrible Things to Her Step Sons! Arya Grander

MomXL 1 year ago

TS Anne amateur orgy with Hex sucking cocks and getting facial cumshots (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Blowbang - Trans Gangbang - Trans Cock Sucker

HD 0:29 / 21:29

TS Anne amateur orgy with Hex sucking cocks and getting facial cumshots (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Blowbang - Trans Gangbang - Trans Cock Sucker

Clips4sale 1 month ago

Basic Rules 4 a novice slut - Mobile Version - No Puppy Chow Today 480p

65% 0:15 / 6:36

Basic Rules 4 a novice slut - Mobile Version - No Puppy Chow Today 480p

Clips4sale 1 year ago

Livestream 10.01.24 - Party with Madame Ophelia and TS Djamila

HD 0:10 / 34:13

Livestream 10.01.24 - Party with Madame Ophelia and TS Djamila

LoyalFans 2 years ago

Deep Throat Training w Nose Plug

Deep Throat Training w Nose Plug

Clips4sale 7 months ago

Ruth & Carlaa Private Show

Ruth & Carlaa Private Show

Flirt4Free 10 months ago

Jade Venus And Lexi Lore: Mouth And Pussy Training - Kink

Jade Venus And Lexi Lore: Mouth And Pussy Training - Kink

Xshemale 1 year ago

Obey, Serve, Repeat - My Sissy Maid’s New Routine POV Now Hiring!!!

68% HD 0:30 / 40:18

Obey, Serve, Repeat - My Sissy Maid’s New Routine POV Now Hiring!!!

Clips4sale 10 months ago

George Kingx Private Show

George Kingx Private Show

Flirt4Free 1 week ago

Doppelschwanz Abrichtung

57% 0:30 / 14:26

Doppelschwanz Abrichtung

Clips4sale 9 months ago

Training Comp

aShemaleTube 6 years ago

Cross Spanking

HD 0:10 / 18:36

LoyalFans 1 year ago

Tina Weeks Private Show

Tina Weeks Private Show

Flirt4Free 3 years ago

Amie Bell Private Show

Amie Bell Private Show

Flirt4Free 3 years ago

Snowbunny playgirl BBC deepthroat training

Snowbunny playgirl BBC deepthroat training

ShemaleSin 2 years ago

Sissy Pegging

61% 0:14 / 6:27

Clips4sale 9 months ago

Super Inflatable Body Bag

Super Inflatable Body Bag

Clips4sale 1 year ago

Trans Girl Stretches her tight hole with ten Huge toys

67% 0:29 / 26:44

Trans Girl Stretches her tight hole with ten Huge toys

Clips4sale 8 months ago

TRANSSEXUAL - Femboy Tripple Climax & Torturing Toes

TRANSSEXUAL - Femboy Tripple Climax & Torturing Toes

TrannyGem 3 years ago

sissy boy training video surrender to black dicks

sissy boy training video surrender to black dicks

aShemaleTube 5 years ago

Pumpkin Spice Sissies

Pumpkin Spice Sissies

Clips4sale 5 months ago

Chicks and Dicks

56% HD 0:27 / 19:31

Chicks and Dicks

Clips4sale 1 year ago

Bennie Bunny Anal Training With Dildo

Bennie Bunny Anal Training With Dildo

ProPorn 1 month ago

Desire Sweet Private Show

HD 2:00 / 25:17

Desire Sweet Private Show

Flirt4Free 1 month 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 5 months ago

Sissy Mesmerize - kendra james, femdom, joi mp4

HD 0:11 / 16:20

Sissy Mesmerize - kendra james, femdom, joi mp4

Clips4sale 2 years ago

Sissygasm Training - Turning your Cock into a Sissy Clit FULL VID on LayneLovee Manyvids

Sissygasm Training - Turning your Cock into a Sissy Clit FULL VID on LayneLovee Manyvids

xHamster 1 year ago

Hanna Ven Private Show

HD 2:00 / 12:51

Hanna Ven Private Show

Flirt4Free 1 year ago

Wear This Dress Or Take A Beating

57% 0:15 / 6:54

Wear This Dress Or Take A Beating

Clips4sale 1 year ago

Hercules & Lian & Lance Private Show

Hercules & Lian & Lance Private Show

Flirt4Free 3 years ago

Aliyah Millers Private Show

HD 2:00 / 11:31

Aliyah Millers Private Show

Flirt4Free 3 months ago

The Royal Training Futanari

The Royal Training Futanari

XVideos 2 years ago

Jerking in the afternoon. Do you like my wooly gams? And cooter? And bunghole?

Jerking in the afternoon. Do you like my wooly gams? And cooter? And bunghole?

TrannyGem 3 years ago

Dreamscape Sissy training

Dreamscape Sissy training

Sheshaft 3 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 4 months ago

Crhistian & Dereckk & Friends Private Show

HD 2:00 / 19:50

Crhistian & Dereckk & Friends Private Show

Flirt4Free 6 years ago

Feminization Sissification Sissy threesome training blowjob

Feminization Sissification Sissy threesome training blowjob

YouPorn Unknown

Mistress Lady Renee - Dressed to suck - mp4

57% 0:16 / 11:09

Mistress Lady Renee - Dressed to suck - mp4

Clips4sale 1 year ago

Sissy Anime Cosplay BBC Anal Training SissyLittleLola

Sissy Anime Cosplay BBC Anal Training SissyLittleLola

xHamster 3 years ago

Goth girl trains her femboy stepbro to become a good slut (Femdom 3D animation)

Goth girl trains her femboy stepbro to become a good slut (Femdom 3D animation)

HentaiGem 3 years ago

Asian ts Venus Lux fucked blonde teen Sarahs wet cunt

Asian ts Venus Lux fucked blonde teen Sarahs wet cunt

Sheshaft 8 years ago

First time in person session- From 0 to a pain and ass slut

First time in person session- From 0 to a pain and ass slut

Clips4sale 2 years ago

(Brown Bottle)Encouraged Aroma | Sissy training | Be sexy like me!Cum like a pussy!

HD 0:20 / 13:38

(Brown Bottle)Encouraged Aroma | Sissy training | Be sexy like me!Cum like a pussy!

Clips4sale 4 years ago

SheMale Evolution

55% 4K 0:15 / 4:26

SheMale Evolution

Clips4sale 2 years ago

Trans FinDom

HD 0:10 / 10:37

LoyalFans 4 years ago

Dildo Hero Games - You get fucked at the gym after workout

Dildo Hero Games - You get fucked at the gym after workout

XVideos 3 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 5 months ago

Goddess in gloves Hard Jerks off slave big cock Controls Orgasms Post Cum Play - Close Female naked male, Uncircumcised dick, Brunette Mistress training cuckold, Orgasm destruction looser, Female Domination, Play Cum after Ejaculation, Handjob

4K 0:26 / 16:03

Goddess in gloves Hard Jerks off slave big cock Controls Orgasms Post Cum Play - Close Female naked male, Uncircumcised dick, Brunette Mistress training cuckold, Orgasm destruction looser, Female Domination, Play Cum after Ejaculation, Handjob

Clips4sale 2 months ago

Sissification Teaching "HOW to PUT PURITY ON?" Sissy Educator Veronica Taboo explains and demonstrates!

Sissification Teaching "HOW to PUT PURITY ON?" Sissy Educator Veronica Taboo explains and demonstrates!

TrannyGem 2 years ago

Big ass trans Crystal Phoenix fucked by BBC fuck machine

Big ass trans Crystal Phoenix fucked by BBC fuck machine

xHamster 9 months ago

Nice Fuck for sexy Crossdresser

Nice Fuck for sexy Crossdresser

xHamster 2 months ago

Using the sissy's slut holes - Part One

47% HD 0:30 / 7:53

Using the sissy's slut holes - Part One

Clips4sale 1 year ago

Sissy Slut Rest Stop

57% HD 0:11 / 8:46

Sissy Slut Rest Stop

Clips4sale 4 years ago

Tranpires, Scene 2: The Rockstar PART 1

51% 4K 0:30 / 11:19

Tranpires, Scene 2: The Rockstar PART 1

Clips4sale 4 years ago

Horus J Private Show

HD 2:00 / 22:57

Horus J Private Show

Flirt4Free 5 years ago

2nd Week of Sissy Training - Bimbofication

HD 0:39 / 2:33:47

2nd Week of Sissy Training - Bimbofication

FapHouse 1 month ago

Your Trans Dominatrix Wants You Forever

4K 0:27 / 44:25

Your Trans Dominatrix Wants You Forever

Clips4sale 2 years ago

FULL CREAM COMPILATION NEO 2

67% 4K 0:59 / 32:01

FULL CREAM COMPILATION NEO 2

Clips4sale 2 years ago

Sissy Academy - Class 2

Sissy Academy - Class 2

Clips4sale 2 years ago

Sissified and Broken Chastity’s Bitch!

57% 0:30 / 14:19

Sissified and Broken Chastity’s Bitch!

Clips4sale 11 months ago

Made suck horny straight guys cock - “ it’s not gay if I think of a girl”

Made suck horny straight guys cock - “ it’s not gay if I think of a girl”

Clips4sale 2 years ago

TRANSSEXUAL Willow Hammerz - BIG BLACK COCK / BNWO / SISSY PMV

TRANSSEXUAL Willow Hammerz - BIG BLACK COCK / BNWO / SISSY PMV

TrannyGem 3 years ago

Femization Lesson POV Femdom with Madame Juliette

53% 0:12 / 10:04

Femization Lesson POV Femdom with Madame Juliette

Clips4sale 2 years ago

Violetta Ficher Fucks Her Pussy and Squirts

HD 2:00 / 16:15

Violetta Ficher Fucks Her Pussy and Squirts

Flirt4Free 1 year ago

Ruth & Carlaa Private Show

Ruth & Carlaa Private Show

Flirt4Free 1 year ago

Chaste Femboy Gimp Suck Experience

Chaste Femboy Gimp Suck Experience

TrannyGem 3 years ago

Verona Glossi Private Show

HD 2:00 / 10:56

Verona Glossi Private Show

Flirt4Free 3 years ago

First Date Surprise Pegging

First Date Surprise Pegging

Clips4sale 8 months ago

CAGED SISSY receives ENEMA and wets DIAPER before SPANKING treatment

HD 0:32 / 17:57

CAGED SISSY receives ENEMA and wets DIAPER before SPANKING treatment

Clips4sale 1 year ago

Mey Evanson Private Show

HD 2:00 / 49:57

Mey Evanson Private Show

Flirt4Free 4 years ago

MILF Controls boy wmv

Premium 4K 18:18

MILF Controls boy wmv

Clips4sale 3 months ago

Training a Sissy Slave

Training a Sissy Slave

FapHouse 1 year ago

Tall Bodybuilder in Small Underwear Tied Up

HD 2:00 / 44:37

Tall Bodybuilder in Small Underwear Tied Up

Flirt4Free 9 years ago

Cuck, His BBC makes my Tummy Bulge - 4K

55% 4K 0:27 / 15:44

Cuck, His BBC makes my Tummy Bulge - 4K

Clips4sale 9 months ago

Spy Transformed into Submissive American House Wife Slut

Spy Transformed into Submissive American House Wife Slut

Clips4sale 2 years ago

Lora Bakers Private Show

Lora Bakers Private Show

Flirt4Free 1 year ago

Stefanias sissy bitch POV_wmv_

Stefanias sissy bitch POV_wmv_

Clips4sale 1 year ago

Just Get in the Cage

64% 4K 0:30 / 18:25

Just Get in the Cage

Clips4sale 1 year ago

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

68% HD 0:30 / 13:38

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

Clips4sale 1 year ago

Ariel Nitzche Private Show

HD 2:00 / 47:57

Ariel Nitzche Private Show

Flirt4Free 2 years ago

Dildo Dolly 4

58% 0:11 / 11:52

Clips4sale 3 years ago

Sissy Porn Will Rot Your Brain

66% HD 0:29 / 11:01

Sissy Porn Will Rot Your Brain

Clips4sale 10 months ago

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