Training Videos - Trans (89,378)

Sissy crossdresser gets double stuffed part two

Sissy crossdresser gets double stuffed part two

SortPorn 4 years ago

Hooded sissy gets his ass paddled, spanked, rimmed and penetrated before fem dom girlfriend allows h

Hooded sissy gets his ass paddled, spanked, rimmed and penetrated before fem dom girlfriend allows h

Fapcat 3 years ago

Furry trap slave training

Furry trap slave training

Tranny.one 4 years ago

Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks Off to Big Black Cock

Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks Off to Big Black Cock

xHamster 5 months ago

Waifu Cristal Private Show

61% 4K 2:00 / 16:09

Waifu Cristal Private Show

Flirt4Free 1 month ago

Serge3dx Training Tsunade Legendary Episode Creampie Inside the Sweet and Tight Pussy Dripping Cum Intense Pleasure, Buttocks

Serge3dx Training Tsunade Legendary Episode Creampie Inside the Sweet and Tight Pussy Dripping Cum Intense Pleasure, Buttocks

xHamster 1 year ago

Insatiable Sissy Melody Sluts Out with a Huge Dildo

Insatiable Sissy Melody Sluts Out with a Huge Dildo

xHamster 1 year ago

Charlie Cano Private Show

61% HD 2:00 / 25:10

Charlie Cano Private Show

Flirt4Free 3 years ago

FROM OUTDOOR TO DAYBED!! WILD SEX OF NYMPHOMANIACS!

FROM OUTDOOR TO DAYBED!! WILD SEX OF NYMPHOMANIACS!

ShemaleSin 1 year ago

You Never Fuck a Woman! Just a Sexy Pillow! Lol!!! JOI for Real Losers! German

You Never Fuck a Woman! Just a Sexy Pillow! Lol!!! JOI for Real Losers! German

FapHouse 2 months ago

Stretching my Ass - Sissy Training

Stretching my Ass - Sissy Training

Tranny.one 1 year ago

Scott Carterr & Michael Magno Private Show

46% HD 2:00 / 4:59

Scott Carterr & Michael Magno Private Show

Flirt4Free 2 years ago

Deep Anal Training Sissy Caged Cumshot - Sohimi Monster Dildo Vs Jessica Bloom

Premium HD 16:44

Deep Anal Training Sissy Caged Cumshot - Sohimi Monster Dildo Vs Jessica Bloom

XVideosRed 1 year ago

Hot Trans Secretary Discipline Meeting With The Boss

Hot Trans Secretary Discipline Meeting With The Boss

xHamster 3 months ago

SISSY LATEXDOLL GETTING OFF #2

SISSY LATEXDOLL GETTING OFF #2

TrannyGem 11 months ago

Helena Miles Private Show

HD 2:00 / 14:59

Helena Miles Private Show

Flirt4Free 4 years ago

Sophia Loreen Private Show

HD 2:00 / 13:35

Sophia Loreen Private Show

Flirt4Free 14 hours ago

I Cumming From Hard Strap on Fuck

I Cumming From Hard Strap on Fuck

xHamster 2 years ago

Carmen Masterz & Patravontesse tag team Jock bottom in hot BBW threesome

Carmen Masterz & Patravontesse tag team Jock bottom in hot BBW threesome

TrannyMovs 6 months ago

The dominatrix wife dressed up her sissy husband and had fuck with him on Halloween.

The dominatrix wife dressed up her sissy husband and had fuck with him on Halloween.

Pornzona 1 week ago

Trashy Gamers (Every Gamers Fantasy)

Trashy Gamers (Every Gamers Fantasy)

Pornzona 2 weeks ago

Sissys Pussy Clit Teased N Dildo Destroyed Gushing Cum

Sissys Pussy Clit Teased N Dildo Destroyed Gushing Cum

JuicyTrans 1 week ago

Playing with My Big Boobs

Playing with My Big Boobs

Flirt4Free 4 years ago

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

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

ShemaleSin 2 months ago

Sissy crossdresser anal training PART 1

Sissy crossdresser anal training PART 1

xHamster 1 year ago

Brazilian cuck instructed to play with dildo and vibrator

Brazilian cuck instructed to play with dildo and vibrator

xHamster 2 years ago

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

FapHouse 2 months ago

Guts climax Forearms free-for-all jism Trans woman

Guts climax Forearms free-for-all jism Trans woman

TrannyGem 3 years ago

Femboy Has an Accident While Training and Seduced the Straight Trainer and Ate His Ass

Femboy Has an Accident While Training and Seduced the Straight Trainer and Ate His Ass

xHamster 3 weeks ago

You SISSY Slut Training Video :CAROLYNFOREST

You SISSY Slut Training Video :CAROLYNFOREST

TrannyGem 7 years ago

Latex Doll Training - JessicaXD

Latex Doll Training - JessicaXD

xHamster 3 years ago

SISSY ANAL & CHASTITY training by LATEX Mistress

SISSY ANAL & CHASTITY training by LATEX Mistress

xHamster 2 years ago

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Eporner 1 year ago

Katty Anderson Private Show

50% 4K 2:00 / 10:07

Katty Anderson Private Show

Flirt4Free 5 months ago

Sissy Strap-on Fucked by Asian Mistress Dominafire

Sissy Strap-on Fucked by Asian Mistress Dominafire

xHamster 1 month ago

Charlie Cano Private Show

HD 2:00 / 27:25

Charlie Cano Private Show

Flirt4Free 3 years ago

Luna Florez Private Show

4K 2:00 / 26:55

Luna Florez Private Show

Flirt4Free 2 weeks ago

-Censored- cd anus training jessica bloom anus instructio

-Censored- cd anus training jessica bloom anus instructio

FetishShrine 2 months ago

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

PePorn 4 months ago

Analful of cum and good blowjob by Latina tranny Emma Ink

Analful of cum and good blowjob by Latina tranny Emma Ink

XGroovy 2 years ago

Trans Big Tit Transformation

51% HD 0:39 / 44:49

Trans Big Tit Transformation

FapHouse 6 months ago

Kity Slave Training

Kity Slave Training

aShemaleTube 6 years ago

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 10 months ago

Reina Hanno Anal Kegel Training Trailer

Reina Hanno Anal Kegel Training Trailer

xHamster 3 years ago

New Task:i Piss in transparent Nylonskirt with harness bodyand big boobs

New Task:i Piss in transparent Nylonskirt with harness bodyand big boobs

xHamster 1 year ago

Trans innocence ejaculation

Trans innocence ejaculation

TrannyGem 2 years ago

Stretching and Wrecking My Hole with My Fist Toy Cuming Like a Little Sissy Slut

HD 0:39 / 15:00

Stretching and Wrecking My Hole with My Fist Toy Cuming Like a Little Sissy Slut

FapHouse 1 year ago

Monica Farell Private Show

HD 2:00 / 12:30

Monica Farell Private Show

Flirt4Free 2 years ago

”Drivers class ends with a hard assfucking - Finn Harding , Amanda Riley”

”Drivers class ends with a hard assfucking - Finn Harding , Amanda Riley”

4Wank 2 years ago

$Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen$ 69% HD 2:00 / 27:28

Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen

Flirt4Free 8 months ago

Jacob Malik Private Show

46% HD 2:00 / 16:32

Jacob Malik Private Show

Flirt4Free 6 months ago

Brazilian Hottie Sabrina Prezotte Gets Her Ass Warmed Up by Stud Breno Dias in Intense Training Fuck

Brazilian Hottie Sabrina Prezotte Gets Her Ass Warmed Up by Stud Breno Dias in Intense Training Fuck

XXXShake 1 year ago

Blowjob after workout! Great tranny number in the gym!

Blowjob after workout! Great tranny number in the gym!

xHamster 4 years ago

Sissy HypnoSlaveBoy crossdresses & trains his ass in doggystyle

Sissy HypnoSlaveBoy crossdresses & trains his ass in doggystyle

GayVD 4 weeks ago

femboy gets pummeled by tentacle plaything

femboy gets pummeled by tentacle plaything

TrannyGem 1 year ago

Blonde mistress humiliating with balls kicking her slave boy

Blonde mistress humiliating with balls kicking her slave boy

Tranny.one 4 years ago

sasha de sade bbc gangbang training with my daddy [1080p]

sasha de sade bbc gangbang training with my daddy [1080p]

PornOne 4 years ago

Sissy solo play

Sissy solo play

aShemaleTube 2 days ago

TRANSSEXUAL Willow Hammerz - Sissy PMV

TRANSSEXUAL Willow Hammerz - Sissy PMV

TrannyGem 7 months ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Flirt4Free 1 year ago

Rectal Screw with Pound Machine 1

Rectal Screw with Pound Machine 1

TrannyGem 2 years ago

Sissygasm from ass-fuck getting off in sissy mega-bitch with closed love button in chastity_sc.32

Sissygasm from ass-fuck getting off in sissy mega-bitch with closed love button in chastity_sc.32

TrannyGem 7 months ago

Artesca Private Show

HD 2:00 / 12:29

Artesca Private Show

Flirt4Free 1 week ago

Sexy sissy Ponyboy Showing his nude body and high heels

Sexy sissy Ponyboy Showing his nude body and high heels

xHamster 4 years ago

Ema Devine Private Show

66% 4K 2:00 / 5:07

Ema Devine Private Show

Flirt4Free 9 months ago

Caged Femboy Jessica removes plug and rides 9inch vibrator for u

Caged Femboy Jessica removes plug and rides 9inch vibrator for u

BigTitsLust 1 month ago

Sissy PLUMB in the WOODS

Sissy PLUMB in the WOODS

TrannyGem 3 years ago

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

56% HD 1:01 / 25:43

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

FapHouse 1 year ago

Sissy receive screwed within the booty during playing Fifa

Sissy receive screwed within the booty during playing Fifa

WebcamBros 1 year ago

Sarah and Lucy Feminize You and Mega-breezy You Out

Sarah and Lucy Feminize You and Mega-breezy You Out

TransTube.tv 1 year ago

Femboy Cumshot Sissygasm from Ball-Plapping for the BNWO

Femboy Cumshot Sissygasm from Ball-Plapping for the BNWO

xHamster 7 months ago

Cumslut Training Jessica Bloom Self Suck and Cumplay Cei Cum Eating Instructions

Cumslut Training Jessica Bloom Self Suck and Cumplay Cei Cum Eating Instructions

AbTranny 3 years ago

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

ShemaleSin 10 months ago

Bimbo Air stewardess Jenby Doll anal trains in-flight fuckdoll Momo

Premium HD 5:35

Bimbo Air stewardess Jenby Doll anal trains in-flight fuckdoll Momo

xnxxGold 3 years ago

Alexxa A Private Show

HD 2:00 / 11:39

Alexxa A Private Show

Flirt4Free 2 months ago

Opening My Ass to Receive Your Cock. Luzia_tv Anal Orgasm with Milk in My Mouth

63% HD 0:39 / 6:37

Opening My Ass to Receive Your Cock. Luzia_tv Anal Orgasm with Milk in My Mouth

FapHouse 2 months ago

Luke Hardy & Cristian Ford Party on Apr 11, 2026 - Part 2

HD 2:00 / 1:20:04

Luke Hardy & Cristian Ford Party on Apr 11, 2026 - Part 2

Flirt4Free 1 week ago

Sissy fuckbox teaching four: nice ladyboy in undergarments, transforming pink pucker to snatch

Sissy fuckbox teaching four: nice ladyboy in undergarments, transforming pink pucker to snatch

TrannyGem 3 years ago

Webcam bdsm sissy doxy Alina shows how she desires to suck and deepthroat real dick

Webcam bdsm sissy doxy Alina shows how she desires to suck and deepthroat real dick

Dafreeporn 5 days ago

Sophia Loreen Party on Apr 13, 2026 - Part 8

HD 2:00 / 1:28:05

Sophia Loreen Party on Apr 13, 2026 - Part 8

Flirt4Free 6 days ago

Sucking cock before going to bed

Sucking cock before going to bed

xHamster 7 months ago

3D Muscular Mature Woman Heavy Squats & Ass Workout - Classic Gym Tease Clip 1

3D Muscular Mature Woman Heavy Squats & Ass Workout - Classic Gym Tease Clip 1

xHamster 2 weeks ago

Andrea & Taty Private Show

Andrea & Taty Private Show

Flirt4Free 6 days ago

Elix & Elias & Paulo Private Show

45% HD 2:00 / 5:24

Elix & Elias & Paulo Private Show

Flirt4Free 9 months ago

Spandex Sissy Maid Candy in Innocence and Restrain Bondage Stuck on a Smashing Machine

Spandex Sissy Maid Candy in Innocence and Restrain Bondage Stuck on a Smashing Machine

TrannyGem 1 year ago

Training with Anna

Training with Anna

aShemaleTube 2 years ago

A Girl Is Going to Get Her Ass Fisted

A Girl Is Going to Get Her Ass Fisted

xHamster 3 months ago

Sasha de Sade Anal Training On The Leash With BBC

Sasha de Sade Anal Training On The Leash With BBC

DrTuber 2 months ago

Horny Sissy Daniella in train

Horny Sissy Daniella in train

xHamster 1 year ago

90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut

90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut

xHamster 3 years ago

Anal invasion Sissy Sleepover With Trans Ria Bentley & Lola Crystals

Anal invasion Sissy Sleepover With Trans Ria Bentley & Lola Crystals

TransTube.tv 1 year ago

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

xHamster 2 months ago

Ruslana Coval Private Show

55% 4K 2:00 / 17:07

Ruslana Coval Private Show

Flirt4Free 3 weeks ago

Rock trans cutie makes u lick cum (CEI)

Rock trans cutie makes u lick cum (CEI)

ShemaleSin 4 years ago

Male Sub gets Trained by Trans Domme 2

Male Sub gets Trained by Trans Domme 2

aShemaleTube 6 days ago

My Ultimate Fantasy, Pegging Step Brother.

My Ultimate Fantasy, Pegging Step Brother.

Pornzona 1 week ago

Two rubber doll hungry slutty mouths used Latex Rubber Strapon Mistress POV

Two rubber doll hungry slutty mouths used Latex Rubber Strapon Mistress POV

Pornzona 1 month ago

Amannda Skye Party on Jan 9, 2026 - Part 2

4K 2:00 / 37:46

Amannda Skye Party on Jan 9, 2026 - Part 2

Flirt4Free 3 months ago

B024 Ntr Girlfriend and Her Transgender Bestie Help Her Ex-boyfriend Train

B024 Ntr Girlfriend and Her Transgender Bestie Help Her Ex-boyfriend Train

xHamster 1 month ago

Warming up my juicy Asshole for a bigger one

Warming up my juicy Asshole for a bigger one

xHamster 2 weeks ago

lovely sissy femboy daylight slutwalk for insatiable meatpipes to gargle and jism guzzle

lovely sissy femboy daylight slutwalk for insatiable meatpipes to gargle and jism guzzle

TrannyGem 1 year ago

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

HD 0:39 / 13:57

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

FapHouse 1 year ago

TS Nadia Love Trains For A Competition And Her Coach Sucks Her Cock And Licks Her Big Tits.She Sucks His Dick And Titty Fucks It

TS Nadia Love Trains For A Competition And Her Coach Sucks Her Cock And Licks Her Big Tits.She Sucks His Dick And Titty Fucks It

BeMyHole 1 year ago

Self Sucking Sissy Rimmed And Milked By Girlfriend - (Sissy Jessica Bloom)

Self Sucking Sissy Rimmed And Milked By Girlfriend - (Sissy Jessica Bloom)

xHamster 1 year ago

女装OLアナル調教(1/4)

女装OLアナル調教(1/4)

GayCK 3 years ago

SISSY MILKING PEGGING CIMPILATION

SISSY MILKING PEGGING CIMPILATION

aShemaleTube 10 months ago

SISSY IS BROUGHT TO UNREAL ORGASMS by LARGE Hankey's Toys

SISSY IS BROUGHT TO UNREAL ORGASMS by LARGE Hankey's Toys

ShemaleSin 1 year ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

xHamster 3 weeks ago

Weak Submissive Sissy Jes Brinch Is a Attention Whore!

Weak Submissive Sissy Jes Brinch Is a Attention Whore!

xHamster 3 weeks ago

Kristy Butty Party on Dec 4, 2025 - Part 3

66% 4K 2:00 / 12:43

Kristy Butty Party on Dec 4, 2025 - Part 3

Flirt4Free 4 months ago

JUDE LYNX — OMEGA DIG SCHLONG CUMMING IN PANTS

JUDE LYNX — OMEGA DIG SCHLONG CUMMING IN PANTS

ShemaleSin 1 week ago

Sergeant Izzy Wildes Recruit Training

Sergeant Izzy Wildes Recruit Training

TrannyGem 3 months ago

AB147 Two femdom extrme training BDSM 雙女王的極限調教- strap on 征服

AB147 Two femdom extrme training BDSM 雙女王的極限調教- strap on 征服

aShemaleTube 5 months ago

Chloe Delacroix Private Show

Chloe Delacroix Private Show

Flirt4Free 1 week ago

What Chastity And Hormones Have Done To Her 4K

What Chastity And Hormones Have Done To Her 4K

ShemaleSin 1 year ago

Dilation of an anal by his wife part of a Clip 1

Dilation of an anal by his wife part of a Clip 1

xHamster 2 months ago

Sissy Training by Queen Daralis Part 2

63% HD 0:39 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse 2 months ago

Your Weird T-girl Obsession

Your Weird T-girl Obsession

ShemaleSin 5 months ago

20 Mins!!!! Ebony Mistress Pegging Sissy Crossdresser with Huge Dildo Extreme Femdom Training & Humiliation

20 Mins!!!! Ebony Mistress Pegging Sissy Crossdresser with Huge Dildo Extreme Femdom Training & Humiliation

xHamster 6 months ago

Long training with some helping device

Long training with some helping device

xHamster 4 years ago

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