Training Videos - Trans (87,854)

Big boobies Doctor Dee Williams got a lustful doodling and kissing the moment she took off her panties

Big boobies Doctor Dee Williams got a lustful doodling and kissing the moment she took off her panties

Pornwhite 1 year ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

xHamster 2 months ago

Deepthroat Training With A Double Ended Dildo. With Essex Girl Lisa And Tgirl April

Deepthroat Training With A Double Ended Dildo. With Essex Girl Lisa And Tgirl April

AbTranny 2 years ago

Bimbo Takes on BBC

Bimbo Takes on BBC

xHamster 4 months ago

Sissy Hope Slut tease and denial play time compilation

Sissy Hope Slut tease and denial play time compilation

xHamster 3 years ago

Lucas Miiller Party on Jan 1, 2026 - Part 6

HD 2:00 / 16:01

Lucas Miiller Party on Jan 1, 2026 - Part 6

Flirt4Free 2 months ago

Anouk - Muddy Deep-throat Facefuck - Sleazy Protection-free-for-all - Piss (Backside-nail and Guzzling) - Total Movie

Anouk - Muddy Deep-throat Facefuck - Sleazy Protection-free-for-all - Piss (Backside-nail and Guzzling) - Total Movie

TransTube.tv 1 year ago

BIG BLACK COCK Sissy Biotch getting mouth smashed by Ali Da Reaper for Halloween

BIG BLACK COCK Sissy Biotch getting mouth smashed by Ali Da Reaper for Halloween

TrannyGem 7 months ago

Waiting in the tunnel...

Waiting in the tunnel...

xHamster 3 years ago

Aliyah Millers Private Show

Aliyah Millers Private Show

Flirt4Free 1 week ago

SISSY TRAIN WITH BIG TOY FUCKING MACHINE

SISSY TRAIN WITH BIG TOY FUCKING MACHINE

xHamster 4 months ago

Pink Sissy Maid Candy Is Locked Onto Her Dildo Stand and Rides Her Pole

Pink Sissy Maid Candy Is Locked Onto Her Dildo Stand and Rides Her Pole

xHamster 3 months ago

LolaFrina, the sexy amateur crossdresser, enjoys an intense anal toy play in POV

LolaFrina, the sexy amateur crossdresser, enjoys an intense anal toy play in POV

TrannyMovs 6 months ago

Celeste & Liz Private Show

63% HD 2:00 / 8:47

Celeste & Liz Private Show

Flirt4Free 3 years ago

”Goddess Kyaa & River Enza in Gape Training 1”

”Goddess Kyaa & River Enza in Gape Training 1”

429Men 2 weeks ago

Sissy Slut Training 4

Sissy Slut Training 4

xHamster 4 months ago

FetishMen - Bear Connor Atlas sniffing

FetishMen - Bear Connor Atlas sniffing

GayTube.site 2 years ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 1 week ago

”REALTGIRLS - Good Chick Gone Naughty”

”REALTGIRLS - Good Chick Gone Naughty”

TransHero 1 month ago

Latex Doll thick faux penis

Latex Doll thick faux penis

WebcamBros 3 months ago

Pay your Slaver Girlfriend

Pay your Slaver Girlfriend

ShemaleSin 4 years ago

SISSY FEMBOY RECTAL HAVE FUN

SISSY FEMBOY RECTAL HAVE FUN

TrannyGem 7 months ago

Sissy Maid Instructing sissygasm

Sissy Maid Instructing sissygasm

TrannyGem 4 months ago

Alexxa A Private Show

HD 2:00 / 15:39

Alexxa A Private Show

Flirt4Free 1 week ago

Oh how stunning, exploring with Dweeb, he came to instruct me how to speak Italian and I trained him Mexican hump.

Oh how stunning, exploring with Dweeb, he came to instruct me how to speak Italian and I trained him Mexican hump.

KeekAss 1 year ago

TS slut Korra Del rio in blue stockings loves reverse cowgirl more than anything

TS slut Korra Del rio in blue stockings loves reverse cowgirl more than anything

AnySex 2 years ago

breasty sheladys In boning train

breasty sheladys In boning train

Transvids.tv 10 months ago

Real Futanari Friend With Big Cock Sex Trains Hot Nerdy Babe While Stuffing Her Mouth and Pussy With It

Real Futanari Friend With Big Cock Sex Trains Hot Nerdy Babe While Stuffing Her Mouth and Pussy With It

Xfeed 2 years ago

Beautiful classy tgirl trains her hole pt3

Beautiful classy tgirl trains her hole pt3

aShemaleTube 1 year ago

Bootie Plugged Ambidextrous Upskirt

Bootie Plugged Ambidextrous Upskirt

TrannyGem 8 months ago

Feminization Sissyfication Sissy training - Dong Worship - resigned sissy

Feminization Sissyfication Sissy training - Dong Worship - resigned sissy

ShemaleSin 1 year ago

Trans Girl Masturbating and Cums All Over Her Self

Trans Girl Masturbating and Cums All Over Her Self

xHamster 1 year ago

Patric & Oliver Private Show

60% HD 2:00 / 9:50

Patric & Oliver Private Show

Flirt4Free 3 years ago

Live-webcam Replay - Pegging my Marionette in V-Card ! Subsribe to observe total Vid of 1hour Domina Julia

Live-webcam Replay - Pegging my Marionette in V-Card ! Subsribe to observe total Vid of 1hour Domina Julia

TrannyGem 1 year ago

TRANSSEXUAL Willow Hammerz jerking and spunks all over herself

TRANSSEXUAL Willow Hammerz jerking and spunks all over herself

TrannyGem 9 months ago

Sissykanisa Ride on a Monster Dildo Part2

Sissykanisa Ride on a Monster Dildo Part2

FapHouse 1 year ago

Im gonna turn you into a blower and put you on the street sissy boi SHE-MALE PIMP VERSION

Im gonna turn you into a blower and put you on the street sissy boi SHE-MALE PIMP VERSION

TrannyGem 9 months ago

3rd training session of 13 02 2026 - 30 minutes

3rd training session of 13 02 2026 - 30 minutes

xHamster 3 weeks ago

Ebony sissy dick training

Ebony sissy dick training

xHamster 1 year ago

Femdom Mistress Goddess V teases sissy cuckold husband in chastity cage w her tongue and mouth! POV

Femdom Mistress Goddess V teases sissy cuckold husband in chastity cage w her tongue and mouth! POV

xHamster 1 year ago

Vlada russian teen ts fucking your ass in chastity belt

Vlada russian teen ts fucking your ass in chastity belt

FapHouse 2 years ago

My husband's balls on electricity

My husband's balls on electricity

xHamster 11 months ago

Sissy latexdoll Pissing and Anal Training

Sissy latexdoll Pissing and Anal Training

ShemaleSin 4 years ago

Kendal Smithx Private Show

Kendal Smithx Private Show

Flirt4Free 3 days ago

Sissy Hope Compilation 15

Sissy Hope Compilation 15

xHamster 3 months ago

Amateur crossdresser jerks off cock and cums on her own belly over and over again - Shemale Cumshot Compilation

Amateur crossdresser jerks off cock and cums on her own belly over and over again - Shemale Cumshot Compilation

XGroovy 2 years ago

Sissy Mantra : FemDomme Lola Ruin Indoctrinates You To Be A Good Little Slut Bitch For Her Sissy Training Slut Training FemDom Female Supremacy

HD 0:18 / 11:16

Sissy Mantra : FemDomme Lola Ruin Indoctrinates You To Be A Good Little Slut Bitch For Her Sissy Training Slut Training FemDom Female Supremacy

Clips4sale 1 year ago

My Sissy Anal Training

My Sissy Anal Training

xHamster 11 months ago

Patricia Wolford - Machine self anal training

Patricia Wolford - Machine self anal training

xHamster 7 months ago

Insane sissy taunts and enjoyment hersellf in front of a web cam

Insane sissy taunts and enjoyment hersellf in front of a web cam

TrannyGem 3 years ago

4K - HUGE GIRL SEMEN CANNON!! FIRE!! ~Your estrous Zombie pet girl~

4K 0:09 / 30:06

4K - HUGE GIRL SEMEN CANNON!! FIRE!! ~Your estrous Zombie pet girl~

Clips4sale 2 years ago

Kendal Smithx Private Show

HD 2:00 / 16:59

Kendal Smithx Private Show

Flirt4Free 3 days ago

SMM016-Bondaged sissy, self-bondaged training

SMM016-Bondaged sissy, self-bondaged training

ShemaleSin 11 months ago

My New Maid

56% HD 0:10 / 9:28

LoyalFans 11 months ago

TS Jasmine Lotus Spit Roasted and trained to be a proper Anal Slut by Alexxa Von Hell & Slayer

68% 0:11 / 22:42

TS Jasmine Lotus Spit Roasted and trained to be a proper Anal Slut by Alexxa Von Hell & Slayer

Clips4sale 2 years ago

Self-training 50 Punishment Rope Crossing the Train

Self-training 50 Punishment Rope Crossing the Train

FapHouse 2 months ago

Footjob with Short White Ankle Socks

66% HD 2:00 / 7:51

Footjob with Short White Ankle Socks

Flirt4Free 4 years ago

Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time

Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time

xHamster 3 weeks ago

Sissy Training Dominatrix Pegs Goth Sissy And Makes Her

Sissy Training Dominatrix Pegs Goth Sissy And Makes Her

Eporner 1 month ago

Luna Grans Private Show

Luna Grans Private Show

Flirt4Free 4 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Blonde Sissy caged and riding dildo

Blonde Sissy caged and riding dildo

xHamster 3 years ago

Short Version of Bailey Playtime with Her Toys Getting Ready for Stepdaddy

Short Version of Bailey Playtime with Her Toys Getting Ready for Stepdaddy

FapHouse 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

Marcus Leroy Private Show

Marcus Leroy Private Show

Flirt4Free 2 years ago

Sissy boi pussy training

Sissy boi pussy training

xHamster 9 months ago

Handsfree Jizz flow Compilation - Chastity Cage and Ass Plug

Handsfree Jizz flow Compilation - Chastity Cage and Ass Plug

ShemaleSin 1 year ago

Sissy Slut in a Reverse Cowgirl Position Wearing Red High Heels and a Flat Chastity

Sissy Slut in a Reverse Cowgirl Position Wearing Red High Heels and a Flat Chastity

xHamster 9 months ago

trans female getting fucked from behind and lovin’ it

trans female getting fucked from behind and lovin’ it

TrannyGem 5 months ago

Colombian Boys Private Show

55% HD 2:00 / 11:48

Colombian Boys Private Show

Flirt4Free 6 months ago

Three Guys Having Fun Together

HD 2:00 / 24:34

Three Guys Having Fun Together

Flirt4Free 8 years ago

$Huge Titted Asian Trans Talks Dirty As She Rides Her Doll\'s Cock$ HD 2:00 / 13:18

Huge Titted Asian Trans Talks Dirty As She Rides Her Doll\'s Cock

Flirt4Free 7 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

Bambi Sissy Transformation (Sissy caption Story)

Bambi Sissy Transformation (Sissy caption Story)

ShemaleSin 4 years ago

Lee Demon Private Show

4K 2:00 / 14:49

Lee Demon Private Show

Flirt4Free 1 week ago

Ai Salon Sucker

Ai Salon Sucker

Clips4sale 2 years ago

Duct Tape over Mouths and Saran Boys

HD 2:00 / 20:07

Duct Tape over Mouths and Saran Boys

Flirt4Free 8 years ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 1 week ago

Alexxa A Private Show

66% HD 2:00 / 11:06

Alexxa A Private Show

Flirt4Free 1 month ago

Another Transgender Slut Training Herself To Suck Her Own Thicc Cock, AI Generated

Premium HD 1:23

Another Transgender Slut Training Herself To Suck Her Own Thicc Cock, AI Generated

xnxxGold 3 months ago

My Futa Tennis Coach Trains Me Hard Everyday

My Futa Tennis Coach Trains Me Hard Everyday

BigTitsLust 1 month ago

Ebony nurse Kira Noir banged by femboy Jean Hollywood

Ebony nurse Kira Noir banged by femboy Jean Hollywood

VikiPorn 1 year ago

Redhead Latina Twerk Ass While Playing with Your Thong

Redhead Latina Twerk Ass While Playing with Your Thong

xHamster 1 month ago

Petra,s 10th training

Petra,s 10th training

aShemaleTube 7 months ago

Doggy Pose Hard Spanks

Doggy Pose Hard Spanks

Flirt4Free 11 months ago

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

46% HD 0:10 / 14:09

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

LoyalFans 11 months ago

Molten trap juggling on 2 immense faux-cocks

Molten trap juggling on 2 immense faux-cocks

TrannyGem 3 years ago

Cynthia and her secret training - Animation by I-spoks

Cynthia and her secret training - Animation by I-spoks

HentaiGem 3 years ago

Mesmeriza Compilation 12 Island of Oblivion

Mesmeriza Compilation 12 Island of Oblivion

xHamster 1 year ago

My Little Basement Doggy

My Little Basement Doggy

ShemaleSin 5 months ago

PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.

PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.

xHamster 2 years ago

Angel Joseph Private Show

HD 2:00 / 28:18

Angel Joseph Private Show

Flirt4Free 2 weeks ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

TRANSSEXUAL W I L L O W - Encaged Sissy Fap

TRANSSEXUAL W I L L O W - Encaged Sissy Fap

TrannyGem 1 year ago

Feminized By Fresh Stepfather - A Sissy Caption Story ????????????

Feminized By Fresh Stepfather - A Sissy Caption Story ????????????

ShemaleSin 2 years ago

Faux penis training arms free-for-all jizz (numerous orgasms)

Faux penis training arms free-for-all jizz (numerous orgasms)

WebcamBros 3 weeks ago

Obese Booty Femboy with Ripped Leggins Noisy Cumfarts and Multiple Anal Creampies

Obese Booty Femboy with Ripped Leggins Noisy Cumfarts and Multiple Anal Creampies

ShemaleSin 4 days ago

Double Master Sissy Lapdance

66% HD 0:39 / 13:08

Double Master Sissy Lapdance

FapHouse 1 year ago

SISSY CLITTY SOCKJOB MESMERIZE - Sissy Slut, Slut Training, Pantyhose Fetish Mesmerize

SISSY CLITTY SOCKJOB MESMERIZE - Sissy Slut, Slut Training, Pantyhose Fetish Mesmerize

Clips4sale 1 year ago

Slutty cd dildo assfucked by machine

Slutty cd dildo assfucked by machine

xHamster 5 days ago

Junnior & Archie Private Show

Junnior & Archie Private Show

Flirt4Free 3 weeks ago

Goth Femboy Gets Bred by BBC

Goth Femboy Gets Bred by BBC

TatBabes 1 year ago

Domme is daydreaming about opening up your cock-squeezing shagging boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

Domme is daydreaming about opening up your cock-squeezing shagging boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 9 months ago

Just a Silly Sissy Jerking His Cock While Fuck Her Boypussy

Just a Silly Sissy Jerking His Cock While Fuck Her Boypussy

FapHouse 2 weeks ago

Sex Party with Crhristian & Dereckk

57% HD 2:00 / 32:00

Sex Party with Crhristian & Dereckk

Flirt4Free 8 years ago

Sissy Anal Slut PMV 2017

Sissy Anal Slut PMV 2017

Eporner 6 years ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 28:09

Luke Hardy & Cristian Ford Private Show

Flirt4Free 7 months ago

Humiliation, strap-on and deep fisting Clip 1

Humiliation, strap-on and deep fisting Clip 1

xHamster 1 month ago

Sissy Train, Second Suckling Test

Sissy Train, Second Suckling Test

xHamster 1 year ago

Sissy Natasha spills & urinates out of virginity encaged rod from Lovense hook-up machine screwing!

Sissy Natasha spills & urinates out of virginity encaged rod from Lovense hook-up machine screwing!

TrannyGem 2 years ago

Anny Harley Private Show

HD 2:00 / 18:05

Anny Harley Private Show

Flirt4Free 2 years ago

The Surprise

Clips4sale 3 years ago

Mi Ama me da la llave de la jaula y me corro como mujer usando un vibrador

Mi Ama me da la llave de la jaula y me corro como mujer usando un vibrador

TrannyGem 3 months ago

TRANSSEXUAL W I L L O W - BNWO SnowSissy PMV

TRANSSEXUAL W I L L O W - BNWO SnowSissy PMV

TrannyGem 3 years ago

SUBMISSIVE SKINNY LADYBOY ANAL CREAMPIE &amp_ FISTING

Premium HD 6:36

SUBMISSIVE SKINNY LADYBOY ANAL CREAMPIE &amp_ FISTING

xnxxGold 1 month ago

I eat my cum and love to get there.

I eat my cum and love to get there.

xHamster 2 years ago

Femdom ponyplay riding and training of cute pony transgirl

Femdom ponyplay riding and training of cute pony transgirl

ShemaleSin 4 years ago

Summertime Saga Part 186 - Two Milfs by MissKitty2K

Summertime Saga Part 186 - Two Milfs by MissKitty2K

xHamster 6 months ago

Sissy Let out of Purity For Her Deep Urethral Sounding

Sissy Let out of Purity For Her Deep Urethral Sounding

TrannyGem 3 years ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 1 week ago

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