Training Videos - Trans (87,293)

Beauty Shemale Anal Training Using Cucumber

Beauty Shemale Anal Training Using Cucumber

xHamster 4 years ago

Mindless Ruined Faggot Jes Brinch from Denmark

Mindless Ruined Faggot Jes Brinch from Denmark

xHamster 3 months ago

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

xHamster 3 weeks ago

In Silence, Stepsisters make Cum Slut Earn Her Keep

In Silence, Stepsisters make Cum Slut Earn Her Keep

Clips4sale 2 months ago

Sissy Forearms Free-For-All two Jizm dual climax Fuckmachine

Sissy Forearms Free-For-All two Jizm dual climax Fuckmachine

TrannyGem 3 years ago

Anal gape complications

Anal gape complications

xHamster 2 months ago

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

xHamster 5 months ago

Viktor Renaldi Private Show

HD 2:00 / 58:54

Viktor Renaldi Private Show

Flirt4Free 3 years ago

Zayra Ross Private Show

Zayra Ross Private Show

Flirt4Free 1 week ago

Sissy In Diaper Punished With Strict Pegging

Sissy In Diaper Punished With Strict Pegging

BallsAndBoobs 5 months ago

Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR

Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR

xHamster 1 year ago

Alexander & Patric & Alfonso Private Show

61% HD 2:00 / 1:33:17

Alexander & Patric & Alfonso Private Show

Flirt4Free 3 years ago

Feminization Sissication Sissy instructing - Glad Idiot - Innocence Jizz

Feminization Sissication Sissy instructing - Glad Idiot - Innocence Jizz

TrannyGem 7 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Hotel Pegging with Sissy Sophie and My Big Black Cock

63% HD 1:01 / 25:17

Hotel Pegging with Sissy Sophie and My Big Black Cock

FapHouse 3 weeks ago

Feminized and Fucked by My Strapon

50% HD 0:10 / 9:53

Feminized and Fucked by My Strapon

LoyalFans 2 years ago

Four Friends with Four Sexy Cocks Orgy Show

HD 2:00 / 39:43

Four Friends with Four Sexy Cocks Orgy Show

Flirt4Free 8 years ago

Sissy Kara Opens Up Her Crevice With Xxl Faux-Cock

Sissy Kara Opens Up Her Crevice With Xxl Faux-Cock

TrannyGem 6 months ago

Alejandra Fox Private Show

HD 2:00 / 19:14

Alejandra Fox Private Show

Flirt4Free 2 years ago

Sissy Transgirl in Handcuffs Anal Fucked by Big Black Dildo in her Girly Fat Ass until her Asshole Gapes

Sissy Transgirl in Handcuffs Anal Fucked by Big Black Dildo in her Girly Fat Ass until her Asshole Gapes

xHamster 5 months ago

Shemale Fucked Her Personal Trainer

HD 1:01 / 27:00

Shemale Fucked Her Personal Trainer

FapHouse 2 weeks ago

Now Her Life Has Purpose

Now Her Life Has Purpose

xHamster 4 months ago

Compliant trans redhead gives a sloppy oral sex her dommy redhead trans girlfriend

Compliant trans redhead gives a sloppy oral sex her dommy redhead trans girlfriend

ShemaleSin 1 month ago

Lian & Christian & Layan Private Show

HD 2:00 / 10:05

Lian & Christian & Layan Private Show

Flirt4Free 3 years ago

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

56% HD 0:39 / 12:50

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

FapHouse 5 months ago

Making My Cock Explode

62% HD 1:01 / 8:10

Making My Cock Explode

FapHouse 4 months ago

Latino Twinks Show Off Athleticism in Hardcore Action

HD 2:00 / 1:07:33

Latino Twinks Show Off Athleticism in Hardcore Action

Flirt4Free 8 years ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

60% HD 1:01 / 11:01

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

FapHouse 1 year ago

Wife Makes You Her Mtf Sissy Slut Camwhore & Lesbian Lover

HD 0:39 / 17:35

Wife Makes You Her Mtf Sissy Slut Camwhore & Lesbian Lover

FapHouse 1 month ago

MY NEIGHBOR DEEPTHROATS MY MAN SAUSAGE IN THE KITCHEN AND THEN GETS NAILED

MY NEIGHBOR DEEPTHROATS MY MAN SAUSAGE IN THE KITCHEN AND THEN GETS NAILED

4Gay 3 months ago

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

67% HD 0:30 / 17:40

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

Clips4sale 1 year ago

spouse sissification

spouse sissification

ShemaleSin 3 years ago

Ryley Rails Dominates You

61% HD 1:01 / 13:17

Ryley Rails Dominates You

FapHouse 4 months ago

fodendo a gostosa da luiza devil na cachoeira em taubate

fodendo a gostosa da luiza devil na cachoeira em taubate

PornBox 1 month ago

Master & Ithan Private Show

56% HD 2:00 / 5:59

Master & Ithan Private Show

Flirt4Free 7 months ago

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

xHamster 1 year ago

BLOWBANG 2 fag dirty talk 33

BLOWBANG 2 fag dirty talk 33

Eporner 5 years ago

PP's Slave Training - SUBMIT. GOON. REPEAT

PP's Slave Training - SUBMIT. GOON. REPEAT

xHamster 2 years 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

XVideosRed 3 years ago

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

xHamster 4 years ago

Crhistian & Dereckk & Friends Private Show

Crhistian & Dereckk & Friends Private Show

Flirt4Free 7 years ago

Foolish Sissy Feminization Captions

Foolish Sissy Feminization Captions

TrannyGem 3 months ago

Submissive femboy is feminized and fucked

Submissive femboy is feminized and fucked

xHamster 1 year ago

Sissy's Dream 3

55% HD 1:01 / 7:13

Sissy's Dream 3

FapHouse 7 months ago

Extended Cut Destroying My Sissy Fat Ass with a Huge Inflatable Dildo and an Anal Butt Plug

HD 1:01 / 11:59

Extended Cut Destroying My Sissy Fat Ass with a Huge Inflatable Dildo and an Anal Butt Plug

FapHouse 3 months ago

Emo Sissy Femboy Struggling to Take a Huge Anal Dildo with No Warmup

Emo Sissy Femboy Struggling to Take a Huge Anal Dildo with No Warmup

xHamster 6 months ago

Worship Superior Foreskin

Worship Superior Foreskin

xHamster 1 month ago

rubber slave training ass on fucking machine

rubber slave training ass on fucking machine

xHamster 3 weeks ago

Nicolle Monroe Private Show

Nicolle Monroe Private Show

Flirt4Free 5 years ago

Edging My Girl Cock with My Clear Fleshlight

66% 1:01 / 24:43

Edging My Girl Cock with My Clear Fleshlight

FapHouse 1 year ago

Sissy Outdoor Play/ride faux-cock in woods puny pearl

Sissy Outdoor Play/ride faux-cock in woods puny pearl

TrannyGem 7 months ago

EXPOSING SLUT MICHELLE

63% HD 0:10 / 10:41

EXPOSING SLUT MICHELLE

LoyalFans 2 years ago

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

xHamster 1 year ago

Friends with benefits - Jake Power&Kimberlee. Bj, Feeding, throat training

Friends with benefits - Jake Power&Kimberlee. Bj, Feeding, throat training

FapHouse 2 years ago

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

66% HD 1:01 / 1:00:31

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

FapHouse 4 years ago

Elias & Elix Private Show

43% HD 2:00 / 13:09

Elias & Elix Private Show

Flirt4Free 6 months ago

Sophia Loreen Private Show

4K 2:00 / 16:47

Sophia Loreen Private Show

Flirt4Free 2 months ago

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

EpicGFs 1 year ago

Sissy Intense Anal Fucking with Rockhard Monstercock

Sissy Intense Anal Fucking with Rockhard Monstercock

xHamster 1 month ago

POV Asshole Close and Doggy

POV Asshole Close and Doggy

xHamster 1 month ago

Female Dom Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Fucksluts

Female Dom Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Fucksluts

TrannyGem 5 years ago

Femboy Gape Compilation

Femboy Gape Compilation

FapHouse 1 month ago

Rigid a-hole Teaching Of t-model

Rigid a-hole Teaching Of t-model

TrannyGem 6 years ago

Jasmine Dlight Extreme Anal Fisting with Valentina Rosa Part Two Elbow Deep Gaping Shemale Play

68% HD 0:39 / 7:41

Jasmine Dlight Extreme Anal Fisting with Valentina Rosa Part Two Elbow Deep Gaping Shemale Play

FapHouse 1 year ago

Im intend to turn u into a cock-sucker and put u on the street sissy boi TGIRL PIMP VERSION

Im intend to turn u into a cock-sucker and put u on the street sissy boi TGIRL PIMP VERSION

Amateur8 3 years ago

Mouth fucking a deepthroated sissy bitch while watching porn

Mouth fucking a deepthroated sissy bitch while watching porn

xHamster 4 years ago

banging the hawt Luiza Devil at the waterfall in Taubaté

banging the hawt Luiza Devil at the waterfall in Taubaté

ShemaleSin 2 weeks ago

Sophia Loreen Private Show

58% 4K 2:00 / 4:47

Sophia Loreen Private Show

Flirt4Free 5 months ago

reward pegging for latex futa mommy's trained chastity submissive - full video on Veggiebabyy Manyvids

reward pegging for latex futa mommy's trained chastity submissive - full video on Veggiebabyy Manyvids

xHamster 5 months ago

I'll Turn You Into My Sissy Slut!

I'll Turn You Into My Sissy Slut!

xHamster 2 months ago

Full 2025 Cumpilation

55% HD 0:39 / 26:50

Full 2025 Cumpilation

FapHouse 1 month ago

2 huge hands free cumshots in a row

2 huge hands free cumshots in a row

xHamster 1 year ago

becoming femme - gwen how could you look at this and want a pussy after porn video

becoming femme - gwen how could you look at this and want a pussy after porn video

TransDoe 8 months ago

tiatizzianni - nyxi leon shemale commits to be sex slave

tiatizzianni - nyxi leon shemale commits to be sex slave

TransDoe 2 years ago

Take off Your Panties and Take Them All in Your Mouth.

HD 1:01 / 16:51

Take off Your Panties and Take Them All in Your Mouth.

FapHouse 3 months ago

Slut Slave Training

HD 0:39 / 18:09

Slut Slave Training

FapHouse 2 weeks ago

Bella Nightwish Private Show

65% 2:00 / 4:02

Bella Nightwish Private Show

Flirt4Free 1 month ago

No hands cumshot solo compilation from an amateur crossdresser

No hands cumshot solo compilation from an amateur crossdresser

XGroovy 2 years ago

Feminized Large Butt Sissy Giant Anal Creampie Farts and Booty Stretching Training

Feminized Large Butt Sissy Giant Anal Creampie Farts and Booty Stretching Training

ShemaleSin 1 week ago

Alice Summertale Private Show

Alice Summertale Private Show

Flirt4Free 1 week ago

Hot Blonde Sucks Cock Before Anal Pounding

Hot Blonde Sucks Cock Before Anal Pounding

xHamster 4 months ago

Ken Trains Candy to Ride BBC Reverse Cowgirl with Verbal Domination Then Fucks My Pussy Missionary - Candy Ass Sissy

Ken Trains Candy to Ride BBC Reverse Cowgirl with Verbal Domination Then Fucks My Pussy Missionary - Candy Ass Sissy

xHamster 2 years ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

Woman DOMINANCE in DIAPERS and PURITY with a thick ASS-FUCK bootie-speculum and URINATE

Woman DOMINANCE in DIAPERS and PURITY with a thick ASS-FUCK bootie-speculum and URINATE

TransTube.tv 1 year ago

Sissy Maddy Blonde CD Anal Training

Sissy Maddy Blonde CD Anal Training

xHamster 3 months ago

Sissy in ebony vinyl

Sissy in ebony vinyl

Gayhaus 2 months ago

Dimitri Caruso Private Show

HD 2:00 / 14:59

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

FapHouse 1 week ago

Indian Gay Bottom Crossdresser Gaurisissy Pressing and Playing with Her Big Boobs in Black Saree Hard XXX Sex

63% HD 0:39 / 5:36

Indian Gay Bottom Crossdresser Gaurisissy Pressing and Playing with Her Big Boobs in Black Saree Hard XXX Sex

FapHouse 4 months ago

Mistress Rebecca Diamante Sends You to Transsexuals, You Queer Ita

Mistress Rebecca Diamante Sends You to Transsexuals, You Queer Ita

FapHouse 3 weeks ago

Bimbo Cockslut Takes Facial cumshot For Mistress

Bimbo Cockslut Takes Facial cumshot For Mistress

TransTube.tv 1 year ago

Crhistian & Dereckk & Friends Private Show - Part 2

Crhistian & Dereckk & Friends Private Show - Part 2

Flirt4Free 7 years ago

Jaw-dropping moment from "Crossdresser gets machined and gaped by huge dildo on fuckingmachine, leaking cock."

Jaw-dropping moment from "Crossdresser gets machined and gaped by huge dildo on fuckingmachine, leaking cock."

xHamster 6 months ago

Becoming A Sissy (Jerk Off Instructions) w/ Raven Gray

Becoming A Sissy (Jerk Off Instructions) w/ Raven Gray

TrannyGem 3 years ago

Jhordy & Maxx Private Show

58% HD 2:00 / 7:55

Jhordy & Maxx Private Show

Flirt4Free 6 months ago

The Only Way A Sissy Should Be Instructed To Jizz

The Only Way A Sissy Should Be Instructed To Jizz

TrannyGem 2 years ago

Sissy Training Sucking Miss Shell's Futa Cock (HD MP4)

HD 0:26 / 14:00

Sissy Training Sucking Miss Shell's Futa Cock (HD MP4)

Clips4sale 1 year ago

sissy cums in pantyhose. her clit is locked in chastity for 3 days.

sissy cums in pantyhose. her clit is locked in chastity for 3 days.

PornBox 2 years ago

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

TrannyGem 4 years ago

femboy fucked by latex mistress

femboy fucked by latex mistress

Juicexxx 2 months ago

ride dildo

54% HD 2:00 / 6:53

Flirt4Free 4 years ago

Sissies Like Us (Kimber James)

Sissies Like Us (Kimber James)

ShemaleSin 2 years ago

Alexxa Von Hell converts her boytoy into a cum eating slut

64% HD 0:34 / 12:34

Alexxa Von Hell converts her boytoy into a cum eating slut

Clips4sale 1 year ago

See me take this ample nine" node, Dire Cub silver silicon fuck stick

See me take this ample nine" node, Dire Cub silver silicon fuck stick

TrannyGem 2 years ago

Felt Euphoric Bouncing on My Dildos! Sorry for the Bad Camera Angle

Felt Euphoric Bouncing on My Dildos! Sorry for the Bad Camera Angle

FapHouse 2 weeks ago

A Girl Is Going to Get Her Ass Fisted

A Girl Is Going to Get Her Ass Fisted

xHamster 1 month ago

A Girl Is Going to Get Her Ass Fisted

66% 0:39 / 12:36

A Girl Is Going to Get Her Ass Fisted

FapHouse 2 months ago

Independent Training No81 Tucking And Anal Exposure Walk on the Riverside Part 2

Independent Training No81 Tucking And Anal Exposure Walk on the Riverside Part 2

xHamster 1 month ago

Look how pretty feminized you are, your new rules are now coming to leave your masculine life even further behind

Look how pretty feminized you are, your new rules are now coming to leave your masculine life even further behind

xHamster 3 weeks ago

Sissykanisa, a Submissive Femboy Play with Her Mistress's Panties

Sissykanisa, a Submissive Femboy Play with Her Mistress's Panties

xHamster 1 year ago

Getting close to Node on Monstrous Bad Dragon Rex

Getting close to Node on Monstrous Bad Dragon Rex

4Gay 3 months ago

Sun Dress and Big Toys Camshow

65% HD 0:39 / 56:35

Sun Dress and Big Toys Camshow

FapHouse 1 year ago

Sissy Bitch's legs widen for shlong all night - Hardcore Femdom Pegging with Mastix Stellina Obscura

Sissy Bitch's legs widen for shlong all night - Hardcore Femdom Pegging with Mastix Stellina Obscura

ShemaleSin 7 months ago

Worship Daddy's Feet - Obedience Training

Worship Daddy's Feet - Obedience Training

xHamster 2 years ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 2 years ago

Jacob Malik Private Show

53% HD 2:00 / 12:33

Jacob Malik Private Show

Flirt4Free 3 months ago

I ravaged the trans girl protection-free-for-all and hoisted her off the ground with my forearm inwards her backside - Christmas Exclusive

I ravaged the trans girl protection-free-for-all and hoisted her off the ground with my forearm inwards her backside - Christmas Exclusive

Tranny.one 3 weeks ago

Angel Joseph Private Show

HD 2:00 / 21:11

Angel Joseph Private Show

Flirt4Free 1 week ago

Alexxa A Private Show

67% HD 2:00 / 4:03

Alexxa A Private Show

Flirt4Free 3 weeks ago

Mrs Loving's Trains Her Sissy

Mrs Loving's Trains Her Sissy

SexTubeSpot 8 years ago

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