Training Videos - Trans (87,928)

Danna Wright Private Show

HD 2:00 / 14:56

Danna Wright Private Show

Flirt4Free 1 year ago

Sissies Need Rules and Discipline

Sissies Need Rules and Discipline

ShemaleSin 2 months ago

Kasnicole 317 黑丝包裹排精雌堕

Kasnicole 317 黑丝包裹排精雌堕

TrannyGem 1 year ago

Femboy compilation

Femboy compilation

4Gay 1 year ago

Renatha Vega Private Show

Renatha Vega Private Show

Flirt4Free 1 week ago

Manila Tuzon Private Show

Manila Tuzon Private Show

Flirt4Free 5 years ago

Andrea & Taty Private Show

HD 2:00 / 13:00

Andrea & Taty Private Show

Flirt4Free 2 months ago

Sissy in high stilettos and v-card heads outdoors with a vibing hitachi in the donk, falls to the floor

Sissy in high stilettos and v-card heads outdoors with a vibing hitachi in the donk, falls to the floor

TrannyGem 4 months ago

My First Handjob to a Stranger - Sissy Dream

46% HD 1:01 / 9:23

My First Handjob to a Stranger - Sissy Dream

FapHouse 11 months ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 1 year ago

Submissive Ladyboy Anal Casting & Slave Training

65% HD 1:01 / 32:06

Submissive Ladyboy Anal Casting & Slave Training

FapHouse 2 months ago

Tantaly : Frustration and Ejaculation for this Useless Sissy - Mistress Julia

Tantaly : Frustration and Ejaculation for this Useless Sissy - Mistress Julia

xHamster 11 months ago

This Guy Made It Rain a Lot of Cum on My White Boy Face

63% HD 0:39 / 9:25

This Guy Made It Rain a Lot of Cum on My White Boy Face

FapHouse 1 year ago

Sissy maid training

Sissy maid training

ShemaleSin 5 years ago

Cindy take 18 inch sextoy all the way in chastity

Cindy take 18 inch sextoy all the way in chastity

XXXShemalePorn 2 years ago

Ripped Yoga Panties T-girl Anal Stretching Training and Jerking Off until Cumming

Ripped Yoga Panties T-girl Anal Stretching Training and Jerking Off until Cumming

Lesbian8 2 weeks ago

Playful Prison Guard Shemale Gia Darling Likes to Spank Sissy While He Is Sucking Her Cock

Playful Prison Guard Shemale Gia Darling Likes to Spank Sissy While He Is Sucking Her Cock

FapHouse 7 months ago

”Tranny Natalie Mars trains Dr Pierce Paris how to be used like a hoe”

”Tranny Natalie Mars trains Dr Pierce Paris how to be used like a hoe”

ThePornstar 9 months ago

Locked Into Faggotry Forever. Pussy Repulsion Installation

69% 0:43 / 18:34

Locked Into Faggotry Forever. Pussy Repulsion Installation

Clips4sale 1 month ago

Captivating moment from "Dominatrix Mistress April - Slave Rosie gets vacuumed"

Captivating moment from "Dominatrix Mistress April - Slave Rosie gets vacuumed"

xHamster 6 months ago

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

HD 0:39 / 15:39

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

FapHouse 2 months ago

Big Balls Sissy in Chastity Cage Huge Ejaculation and Masturbating her Petite Penis like a Hotty

Big Balls Sissy in Chastity Cage Huge Ejaculation and Masturbating her Petite Penis like a Hotty

PornFreeNow 3 months ago

Servilejerome trying/training, failing to 'fight' a transman

Servilejerome trying/training, failing to 'fight' a transman

ShemaleSin 5 years ago

Trans Girl Eating Cum and Inflation Fetish After Dildo Blowjob

61% HD 0:39 / 8:39

Trans Girl Eating Cum and Inflation Fetish After Dildo Blowjob

FapHouse 3 months ago

Manila Tuzon Private Show

Manila Tuzon Private Show

Flirt4Free 6 years ago

Jasmine_Dlight - Oiled up shemale extreme anal training, giant dildos with belly bulge, gapes and prolapse

HD 0:10 / 26:24

Jasmine_Dlight - Oiled up shemale extreme anal training, giant dildos with belly bulge, gapes and prolapse

LoyalFans 10 months ago

Sissy Play

xHamster 5 months ago

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

xHamster 6 months ago

LATEX BONDAGE SHEMALE DEEPTHROAT SUB CROSSDRESSER IN RED HAIR P1

84% HD 0:22 / 10:19

LATEX BONDAGE SHEMALE DEEPTHROAT SUB CROSSDRESSER IN RED HAIR P1

Clips4sale 2 years ago

Summer Raine In Summer Training

Summer Raine In Summer Training

PornUse 5 months ago

Femdom spread that ass

Femdom spread that ass

FapHouse 3 years ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 5 days ago

Julieta Shayk Private Show

HD 2:00 / 26:54

Julieta Shayk Private Show

Flirt4Free 2 months ago

CHINESE TRANSGIRL LEITAOXIV DANCING UNTIL SHE SPUNK

CHINESE TRANSGIRL LEITAOXIV DANCING UNTIL SHE SPUNK

TrannyGem 1 year ago

Shemale moaning while fucking herself with a huge vibrator dildo

Shemale moaning while fucking herself with a huge vibrator dildo

xHamster 2 years ago

English Trans Slut With a Cute Cock and a Dirty Mouth Relieved From Chastity

English Trans Slut With a Cute Cock and a Dirty Mouth Relieved From Chastity

xHamster 3 years ago

Big ass latina shemale Nicolly Navarro has hot solo show

Big ass latina shemale Nicolly Navarro has hot solo show

Tranny.one 9 years ago

Sissy Training Her Holes

Sissy Training Her Holes

xHamster 1 year ago

Super-Sexy teenage tranny plays with her humungous fake penises

Super-Sexy teenage tranny plays with her humungous fake penises

TrannyGem 1 year ago

Mean Shemale Does your Sissy Makeup

Mean Shemale Does your Sissy Makeup

ShemaleSin 2 months ago

Cucked in Panties at Thanksgiving

Premium HD 8:20

Cucked in Panties at Thanksgiving

xnxxGold 3 years ago

The guy fucks himself in the ass with sex toys and jerks off the dick

The guy fucks himself in the ass with sex toys and jerks off the dick

XVideos 4 years ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 2 weeks ago

My little swatter cock too soft for the wanker

My little swatter cock too soft for the wanker

xHamster 2 months ago

Stunning moment from "Mesmeriza compilation 13 Dream Island"

Stunning moment from "Mesmeriza compilation 13 Dream Island"

xHamster 5 months ago

Training My Ass with a Black Huge Dildo

Training My Ass with a Black Huge Dildo

xHamster 2 months ago

My Butt Is Made for Anal and Creampies

63% HD 0:39 / 22:24

My Butt Is Made for Anal and Creampies

FapHouse 1 year ago

Grab Me the Hose

Grab Me the Hose

Flirt4Free 2 years ago

Sissy Slut Pegging Compilation Vol.1

Sissy Slut Pegging Compilation Vol.1

BallsAndBoobs 7 months ago

Elix & Elias & Paulo Private Show

61% HD 2:00 / 5:20

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

I was doing Anal Training and I became a Whore and Masturbated

I was doing Anal Training and I became a Whore and Masturbated

ShemaleSin 4 years ago

Extremes Sissy ANAL Training

Extremes Sissy ANAL Training

xHamster 1 year ago

Sissy Kanisa Lube Metal Anal Plug with Her Cum

Sissy Kanisa Lube Metal Anal Plug with Her Cum

FapHouse 1 week ago

Trans Cutie Rika Fox Coarse Interracial POV

Trans Cutie Rika Fox Coarse Interracial POV

ShemaleSin 1 year ago

Endless cum spray

Endless cum spray

FapHouse 3 years ago

Inflating my Dick with 1.5 Liters

Inflating my Dick with 1.5 Liters

xHamster 9 months ago

My homie toyed with me with a bang-out plaything

My homie toyed with me with a bang-out plaything

TrannyGem 4 months ago

Hercules & Matt & Lance Private Show

Hercules & Matt & Lance Private Show

Flirt4Free 3 years ago

Super-Steamy Sissy in Glorious Undergarments Fap!

Super-Steamy Sissy in Glorious Undergarments Fap!

TrannyGem 4 years ago

My Desire - A.B.C. = Always Be Cumming - Dee Angels Cums for You!!!

My Desire - A.B.C. = Always Be Cumming - Dee Angels Cums for You!!!

xHamster 3 years ago

Paul Walkers Private Show

Paul Walkers Private Show

Flirt4Free 5 days ago

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Transvids.tv 8 months ago

Scorching femboy self facial cumshot splooging ejaculation fuckslut

Scorching femboy self facial cumshot splooging ejaculation fuckslut

TrannyGem 1 year ago

BBC dildo training

BBC dildo training

aShemaleTube 1 year ago

Sissy Fisting

65% HD 0:39 / 14:20

FapHouse 5 months ago

Russian Tgirl Very Deep Anal

Russian Tgirl Very Deep Anal

xHamster 4 months ago

Owned Sissy wench streams & screws herself raw during the time that Hotwife femdom female-dominator is away! 4/5 Full vid in a short time

Owned Sissy wench streams & screws herself raw during the time that Hotwife femdom female-dominator is away! 4/5 Full vid in a short time

ShemaleSin 2 years ago

Petra 1e training

Petra 1e training

ShemaleSin 1 year ago

Trio of Hot Latinos Having Fun

Trio of Hot Latinos Having Fun

Flirt4Free 8 years ago

Step Bro Spies On Me Peeing Turned Sissy JOI

Step Bro Spies On Me Peeing Turned Sissy JOI

Fapcat 3 years ago

Super-Sexy Sissy Fuckslut Opens Up Gams And Takes Knob Deep

Super-Sexy Sissy Fuckslut Opens Up Gams And Takes Knob Deep

GayCK 3 years ago

Permanent Chastity Sissy has a sissygasm

Permanent Chastity Sissy has a sissygasm

ShemaleSin 7 months ago

Gaping Hardcore Sissy Doxy in Latex Sissygasm from My Biggest Bad Dragon Rod and Latex Fisting by Mastix Mercer

Gaping Hardcore Sissy Doxy in Latex Sissygasm from My Biggest Bad Dragon Rod and Latex Fisting by Mastix Mercer

ShemaleSin 3 months ago

Spidergwen sucking on a BBC dildo

Spidergwen sucking on a BBC dildo

xHamster 2 years ago

Raspberry Anal Training With Big Dildo On Live Cam

Raspberry Anal Training With Big Dildo On Live Cam

Nuvid 1 month ago

Overloaded Gaping Creampie, How Delphi Can't Get Preganant After This?

HD 0:39 / 12:43

Overloaded Gaping Creampie, How Delphi Can't Get Preganant After This?

FapHouse 8 months ago

Fag slave humiliation compilation 3

Fag slave humiliation compilation 3

xHamster 2 months ago

TRANNY AFTER GYM MASTURBATION

TRANNY AFTER GYM MASTURBATION

xHamster 3 years ago

Goddess Rosie Reed Sissification Feminization Femdom POV Transformation

Goddess Rosie Reed Sissification Feminization Femdom POV Transformation

Pornfact 1 week ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Goddess Rosie: Serve My Every Desire so Sweetly

Goddess Rosie: Serve My Every Desire so Sweetly

xHamster 3 months ago

Sissy Training "wear Tights & High Heels", Sissygasm in Chastity Strap by Dominatrix-Bitch Veronica Taboo

Sissy Training "wear Tights & High Heels", Sissygasm in Chastity Strap by Dominatrix-Bitch Veronica Taboo

ShemaleSin 4 years ago

Holly Princess Private Show

HD 2:00 / 10:56

Holly Princess Private Show

Flirt4Free 2 years ago

POV: Teen horny femboy trains his ass in front of the camera

POV: Teen horny femboy trains his ass in front of the camera

RedTube Unknown

Shemale Fucked Her Personal Trainer

Shemale Fucked Her Personal Trainer

xHamster 1 month ago

Maid Asspussy Training with Sissygasm

Maid Asspussy Training with Sissygasm

xHamster 6 months ago

Guitar, Sissy, Faux-Cock! POINT OF VIEW! Slender CD takes no-mitt cum-shot with XXL rectal fucktoy!

Guitar, Sissy, Faux-Cock! POINT OF VIEW! Slender CD takes no-mitt cum-shot with XXL rectal fucktoy!

TrannyGem 4 years ago

Pegging My Good Girl: Made to Cross Dress, Chastity, Rope, Femdom and Strapon-pov

Pegging My Good Girl: Made to Cross Dress, Chastity, Rope, Femdom and Strapon-pov

xHamster 11 months ago

Sissy BBC addiction BBC submission BBC domination Sissy mindset Sissy possitive affirmation tranny transsexual transsexual trans

Sissy BBC addiction BBC submission BBC domination Sissy mindset Sissy possitive affirmation tranny transsexual transsexual trans

ShemaleSin 3 years ago

Waifu Cristal Private Show

4K 2:00 / 16:09

Waifu Cristal Private Show

Flirt4Free 3 days ago

Gas Mask Role-play

Gas Mask Role-play

Flirt4Free 5 years ago

Mastix Murmur Trains me to Screw her Sissy Doxies - Sasha_de_Sade & MistressMurmur on OF

Mastix Murmur Trains me to Screw her Sissy Doxies - Sasha_de_Sade & MistressMurmur on OF

ShemaleSin 4 years ago

Sarah Reyess Private Show

Sarah Reyess Private Show

Flirt4Free 1 year ago

Sissy Dolly Dungeon space Have fun Time Pegged by Giant Bad Dragon Wire on fake penis and Abased by Mistress Mercer

Sissy Dolly Dungeon space Have fun Time Pegged by Giant Bad Dragon Wire on fake penis and Abased by Mistress Mercer

TransTube.tv 1 year ago

Vends-ta-culotte - Sissy dressed as a soubrette cleaing the hous of his dominatrix

Vends-ta-culotte - Sissy dressed as a soubrette cleaing the hous of his dominatrix

xHamster 2 years ago

Self Quickie in Nude Lingerie and Relaxation in the Bath

Self Quickie in Nude Lingerie and Relaxation in the Bath

xHamster 2 years ago

I Cumming From Hard Strap on Fuck

I Cumming From Hard Strap on Fuck

xHamster 2 years ago

Сute t-model plays with her files and faux-cock

Сute t-model plays with her files and faux-cock

TrannyGem 2 years ago

Michel Andrade & Steven Andersson Private Show

65% HD 2:00 / 23:46

Michel Andrade & Steven Andersson Private Show

Flirt4Free 2 years ago

Colombian Boys Private Show

61% HD 2:00 / 33:09

Colombian Boys Private Show

Flirt4Free 5 months ago

First-Ever SissyGasm by BIG BLACK COCK - From Today this Sissy became a BIG BLACK COCK Gimp

First-Ever SissyGasm by BIG BLACK COCK - From Today this Sissy became a BIG BLACK COCK Gimp

TrannyGem 2 years ago

Her Place Is Wherever He Wants Her to Be

Her Place Is Wherever He Wants Her to Be

xHamster 1 month ago

self pee anal pumped swollen ass hole

self pee anal pumped swollen ass hole

xHamster 2 years ago

Feminization Affirmations

54% HD 0:10 / 9:30

Feminization Affirmations

LoyalFans 1 year ago

”Hogtied in the air slave cunt fisted”

”Hogtied in the air slave cunt fisted”

TransHero 3 months ago

Sophia Loreen Private Show

4K 2:00 / 14:03

Sophia Loreen Private Show

Flirt4Free 4 months ago

Allie North being nice and wide open

Allie North being nice and wide open

TrannyGem 3 years ago

イヤァ〰❗そこダメぇ〰❗マシンに犯さてつつもお潮を吹いて喜ぶ制服女子

イヤァ〰❗そこダメぇ〰❗マシンに犯さてつつもお潮を吹いて喜ぶ制服女子

TrannyGem 2 years ago

Nastya Blue Private Show

HD 2:00 / 11:03

Nastya Blue Private Show

Flirt4Free 2 years ago

Ohmibod and Cumshot

HD 2:00 / 46:13

Ohmibod and Cumshot

Flirt4Free 7 years ago

Advanced Anal Stretching with Jasmine-Dlight: Part 2 - Standing Position

61% HD 0:10 / 9:53

Advanced Anal Stretching with Jasmine-Dlight: Part 2 - Standing Position

LoyalFans 5 months ago

Thank You for Smoking

59% HD 2:00 / 25:46

Thank You for Smoking

Flirt4Free 6 years ago

Sophia Loreen Party on Oct 24, 2025 - Part 5

4K 2:00 / 27:09

Sophia Loreen Party on Oct 24, 2025 - Part 5

Flirt4Free 4 months ago

BEST ROUND ASS BOUNCING! Enjoy my body naked a hot twerk in your face and a ride dildo without stop! - Part 3

BEST ROUND ASS BOUNCING! Enjoy my body naked a hot twerk in your face and a ride dildo without stop! - Part 3

Flirt4Free 6 months ago

Latin babe Sissy Floozy Femboy Groans like a Little Whore

Latin babe Sissy Floozy Femboy Groans like a Little Whore

ShemaleSin 1 day ago

Full: Big Balls Sissy in Chastity Cage Massive Cumshot and Masturbating Her Small Dick Like a Girl

HD 0:39 / 26:51

Full: Big Balls Sissy in Chastity Cage Massive Cumshot and Masturbating Her Small Dick Like a Girl

FapHouse 3 months ago

$Solve a Cube of Rubik\'s with Me in the Shower$ 63% 4K 2:00 / 2:38

Solve a Cube of Rubik\'s with Me in the Shower

Flirt4Free 5 months ago

Pony & Sybian

FapHouse 2 years ago

An Unexpected Christmas Gift: Sissy's Penetration - Mistress Julia

HD 0:39 / 16:56

An Unexpected Christmas Gift: Sissy's Penetration - Mistress Julia

FapHouse 1 year ago

Piss Pump Evolution 04 - Dildo Edition

Piss Pump Evolution 04 - Dildo Edition

FapHouse 1 year ago

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