Training Videos - Trans (92,907)

Slutty CD anal training & orgasm💋🍆💦💦

Slutty CD anal training & orgasm💋🍆💦💦

aShemaleTube 1 year ago

becomingfemme - natty is a beautiful blonde sissy

becomingfemme - natty is a beautiful blonde sissy

TransDoe 2 years ago

this kitty get's played with and ruined with oral cumshot

this kitty get's played with and ruined with oral cumshot

Tranny.one 4 years ago

becomingfemme - natty is queen of the sissy university

becomingfemme - natty is queen of the sissy university

TransDoe 2 years ago

Charlotte Sins Lesbian In Training

Charlotte Sins Lesbian In Training

Eporner 2 months ago

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one 4 years ago

Big Compilation Of Anal Orgasms And Solo Cumshots Collection sissygasm ( trap milking )

Big Compilation Of Anal Orgasms And Solo Cumshots Collection sissygasm ( trap milking )

Pornzona 2 months ago

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

AbTranny 8 years ago

Sissy Ladyboy Training

Sissy Ladyboy Training

Tranny.one 4 years ago

Sissy Dolly Basement Have Fun Time Pegged by Giant Bad Dragon Strap Dildo and Abased by Domina Mercer

Sissy Dolly Basement Have Fun Time Pegged by Giant Bad Dragon Strap Dildo and Abased by Domina Mercer

TrannyGem 3 years ago

Public GOING KNUCKLE DEEP sissy ARSE

Public GOING KNUCKLE DEEP sissy ARSE

TrannyGem 3 years ago

Kymmy Harper goes wild for cum and cock in hot threesome action

Kymmy Harper goes wild for cum and cock in hot threesome action

TrannyMovs 7 months ago

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube 2 years ago

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

aShemaleTube 5 years ago

Cum eating trainer video for the greedy sissy faggot whores

Cum eating trainer video for the greedy sissy faggot whores

Tranny.one 3 years ago

Training myself for real Cocks

Training myself for real Cocks

2BGay 1 year ago

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

PornoXO 7 months ago

Femboy instructing part 1: The Back Bend

Femboy instructing part 1: The Back Bend

Gay4Porn 2 years ago

Sissy Fuck Training

Sissy Fuck Training

aShemaleTube 4 years ago

Anal Training Compilation

Anal Training Compilation

BeMyHole 3 years ago

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

xHamster 3 years ago

Fucked by Old Man Behind the Scenes

60% 1:01 / 28:00

Fucked by Old Man Behind the Scenes

FapHouse 1 year ago

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

Axel Reigns _Anal-Training-amp-Creampie-for-Pup-Sasha-De-Sade

aShemaleTube 1 year ago

BBC TRAINING WITH CERJOY

BBC TRAINING WITH CERJOY

xHamster 8 months ago

My Sissy Anal Training

My Sissy Anal Training

Pornzona 1 month ago

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem 1 year ago

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

xHamster 7 months ago

Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage

Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage

xHamster 8 months ago

All that mouth training pays off : facefucking marvelous transwife Melody

All that mouth training pays off : facefucking marvelous transwife Melody

ShemaleSin 2 years ago

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

xHamster 4 months ago

Fun with a toy in the bathroom, homemade

Fun with a toy in the bathroom, homemade

Pornzona 1 month ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

Latex Doll Milking Training Chapter 2

42% HD 1:01 / 13:58

Latex Doll Milking Training Chapter 2

FapHouse 5 months ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 1 year ago

Michael is trained by Mistress Agnes and her friends. part 2

Michael is trained by Mistress Agnes and her friends. part 2

XVideos 3 years ago

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

59% HD 0:39 / 23:39

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

FapHouse 6 months ago

Pegging Hardcore Part 1

61% HD 1:01 / 25:58

Pegging Hardcore Part 1

FapHouse 3 months ago

Corporate Training - Episode 2

Corporate Training - Episode 2

xHamster 1 year ago

Good Girl Training: Transfemme Anal JOI

46% HD 1:01 / 17:10

Good Girl Training: Transfemme Anal JOI

FapHouse 1 month ago

Sissycdmish - BBC Loving Slut in Fishnets and Heels

HD 1:01 / 22:16

Sissycdmish - BBC Loving Slut in Fishnets and Heels

FapHouse 2 weeks ago

Heels up, Legs Open: Foot Fetish & Sissy Dildo Play

54% HD 0:39 / 28:02

Heels up, Legs Open: Foot Fetish & Sissy Dildo Play

FapHouse 11 months ago

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one 4 years ago

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

xHamster 9 months ago

Training a cute twink how to get fuck

Training a cute twink how to get fuck

Tranny.one 4 years ago

Humiliation, strap-on and deep fisting

Humiliation, strap-on and deep fisting

xHamster 4 months ago

Sissification, Pegging, Licking Dirty Shoes and Smelly Armpits, Humiliation

Sissification, Pegging, Licking Dirty Shoes and Smelly Armpits, Humiliation

FapHouse 3 weeks ago

Ryu Doll Gets her Insides Scrambled by BBC

Ryu Doll Gets her Insides Scrambled by BBC

ShemaleSin 4 years ago

Facefuck Training of my submissive girlfriend

Facefuck Training of my submissive girlfriend

xHamster 3 weeks ago

Sissy Fuckdoll 2

Sissy Fuckdoll 2

xHamster 6 months ago

Good Girl Training: Transfemme Anal JOI

Good Girl Training: Transfemme Anal JOI

xHamster 1 month ago

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

xHamster 4 years ago

Dressed in White and Ready to Submit

Dressed in White and Ready to Submit

xHamster 7 months ago

Sissy training for your feminization

Sissy training for your feminization

xHamster 7 months ago

Sissy Slut Dana trains her throat

Sissy Slut Dana trains her throat

xHamster 1 month ago

How I Feel About Imposed Bi - Femdom POV

56% HD 1:01 / 12:57

How I Feel About Imposed Bi - Femdom POV

FapHouse 1 month ago

Sissy Affirmations

Sissy Affirmations

ShemaleSin 6 months ago

BNWO Prisoner Orientation Video

55% 4K 0:26 / 12:53

BNWO Prisoner Orientation Video

Clips4sale 11 months ago

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem 6 years ago

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

aShemaleTube 1 year ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Tranny.one 4 years ago

Watch this sissy get trained in extreme cumshot worship & close-up view of her thick ass getting feminized

Watch this sissy get trained in extreme cumshot worship & close-up view of her thick ass getting feminized

TrannyMovs 5 months ago

Hole Training

Eporner 1 year ago

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one 2 years ago

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

TrannyGem 4 years ago

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

56% 1:01 / 14:02

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

FapHouse 2 years ago

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

HD 0:26 / 10:05

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

Clips4sale 7 months ago

AB087 Gentle demonized model college girls - pegging (Asian and English subtitles)

AB087 Gentle demonized model college girls - pegging (Asian and English subtitles)

Transvids.tv 11 months ago

Three Ways to Cum in Chastity - Plapgasm, Anal Sissygasm and Vibegasm Jessica Bloom Sissy Training

Three Ways to Cum in Chastity - Plapgasm, Anal Sissygasm and Vibegasm Jessica Bloom Sissy Training

xHamster 1 month ago

”TS Jade Venus & Lexi Lore mouth & snatch training session”

”TS Jade Venus & Lexi Lore mouth & snatch training session”

LesbianBliss 2 months ago

Inhale My Femboy's Dick (with Lina Lux)

Inhale My Femboy's Dick (with Lina Lux)

TrannyGem 5 months ago

You're Just a Drooling Faggot Slut – Worship My Cock

HD 0:30 / 42:55

You're Just a Drooling Faggot Slut – Worship My Cock

Clips4sale 3 months ago

Corporate Training 2 (Rikolo

Corporate Training 2 (Rikolo

Eporner 5 months ago

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

68% HD 0:39 / 7:36

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

FapHouse 3 months ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 1 year ago

Living His Best Life as a Girl

Living His Best Life as a Girl

xHamster 10 months ago

Feminization Training - Show This To Your Wife

Feminization Training - Show This To Your Wife

xHamster 1 year ago

Fucking My Sissy Ass with a Massive 12in Dildo

Fucking My Sissy Ass with a Massive 12in Dildo

FapHouse 1 week ago

Nyxi Leon teaches another sissy how to handle a big cock like a pro

Nyxi Leon teaches another sissy how to handle a big cock like a pro

TrannyMovs 1 month ago

Deep Anal Play & Sissygasms Creampie Jessica Bloom

Deep Anal Play & Sissygasms Creampie Jessica Bloom

xHamster 4 years ago

Big ass Latina gets facial after anal fuck - Amateur Porn

Big ass Latina gets facial after anal fuck - Amateur Porn

MyLust 2 years ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 10 months ago

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

TransTube.tv 1 year ago

Mistress Sounding Sissy Urethra Streching and Vibrator Fuck

Mistress Sounding Sissy Urethra Streching and Vibrator Fuck

xHamster 3 months ago

Sissy Training Compilation

Sissy Training Compilation

aShemaleTube 7 years ago

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole 11 months ago

Sissy training

Eporner 1 year ago

Boxing Trainer Gets Trained by Janny

53% HD 0:39 / 29:45

Boxing Trainer Gets Trained by Janny

FapHouse 8 months ago

Sissy Training by Queen Daralis Part 2

54% HD 1:01 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse 4 months ago

Kendall Penny New Orleans Gay Training

Kendall Penny New Orleans Gay Training

BeMyHole 1 year ago

Trannies in training - (Episode #08)

Trannies in training - (Episode #08)

xHamster 2 months ago

Confessions of a submissive sissy

Confessions of a submissive sissy

xHamster 1 year ago

Facefuck Training of my compliant girlfriend

Facefuck Training of my compliant girlfriend

Amateur8 2 weeks ago

I Dare You to Resist: Stay Gay or Become My Filthiest Cum-Slut Faggot

65% HD 0:30 / 39:31

I Dare You to Resist: Stay Gay or Become My Filthiest Cum-Slut Faggot

Clips4sale 4 months ago

Whife *

TrannyGem 6 years ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

Sissy trainer - Give your ass

Sissy trainer - Give your ass

DeegX 3 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

xHamster 7 months ago

Sissy Slave Training

Sissy Slave Training

BeMyHole 5 years ago

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

Tranny.one 4 years ago

Training Before New Year's Eve

Training Before New Year's Eve

xHamster 1 month ago

Sissy Circuit Training

75% HD 1:01 / 15:40

Sissy Circuit Training

FapHouse 1 year ago

Femdom Sissy Chastity Tease

Femdom Sissy Chastity Tease

xHamster 1 month ago

Sasha's Morning Spitroast

Sasha's Morning Spitroast

xHamster 11 months ago

Hey Everyone, if You Love Mtof Transformation & Training the Miracle of Transforming Our Femboys or Sissybois Into Stunning Girl

79% HD 1:01 / 5:34

Hey Everyone, if You Love Mtof Transformation & Training the Miracle of Transforming Our Femboys or Sissybois Into Stunning Girl

FapHouse 1 year ago

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TrannyGem 5 years ago

For Your Boy Pussy Ashley Sinclair

70% HD 1:01 / 5:13

For Your Boy Pussy Ashley Sinclair

FapHouse 1 month ago

CHICK TEARING UP SISSY IN CRIMSON

CHICK TEARING UP SISSY IN CRIMSON

TrannyGem 3 years ago

The Sissy Cunt Alina Take the Cum Her Owner Like Good Girl

72% HD 0:39 / 1:51

The Sissy Cunt Alina Take the Cum Her Owner Like Good Girl

FapHouse 11 months ago

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

xHamster 7 months ago

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin 4 years ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

Clips4sale 7 months ago

Lucas's Bi Slave Training

Lucas's Bi Slave Training

Eporner 3 years ago

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube 4 years ago

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

61% HD 1:01 / 6:49

Trainer's Training Session No. 99: Outdoor Spread-leg Tackle with Exposed Cunt

FapHouse 3 months ago

The Sissygasm

xHamster 1 year ago

Shemale Pussy Denial

68% HD 0:20 / 13:02

Shemale Pussy Denial

IWantClips 1 year ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

63% HD 0:39 / 31:09

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

FapHouse 1 month ago

Sofia Ferreira Private Show

Sofia Ferreira Private Show

Flirt4Free 11 months ago

Living His Best Life as a Girl

64% 0:39 / 27:47

Living His Best Life as a Girl

FapHouse 10 months ago

Sissies are Made to be Servants

Sissies are Made to be Servants

ShemaleSin 8 months ago

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