Training Videos - Trans (50,389)

Fuck Us Both Billy

Fuck Us Both Billy

XHamster 10 months ago

Femdom's Cock-hungry Sissy Fetish Exposed

Femdom's Cock-hungry Sissy Fetish Exposed

Jizzberry 4 years ago

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

XHamster 3 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 4 months ago

Becoming Her

XHamster 3 months ago

Sissy Street Walk, Hiking Trail in Panties, Slutty Workout Shorts in Public

Sissy Street Walk, Hiking Trail in Panties, Slutty Workout Shorts in Public

XHamster 4 days ago

Mommy Domme Wakes Her Sissy Step-Son (Preview)

Mommy Domme Wakes Her Sissy Step-Son (Preview)

MyTransfix 4 days ago

Sophia Loreen Party on Jul 7, 2026 - Part 4

54% HD 2:00 / 12:22

Sophia Loreen Party on Jul 7, 2026 - Part 4

Camster 1 month ago

Kept by Jessica Blake Part 4

Kept by Jessica Blake Part 4

XHamster 5 months ago

Ema Devine Private Show

63% 4K 2:00 / 38:07

Ema Devine Private Show

Camster 1 year ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

MyTransfix 2 months ago

Time to Submit Sissy

Time to Submit Sissy

XHamster 1 month ago

The Hot Rabbit 🐰

The Hot Rabbit 🐰

WebcamBros 10 months ago

Tied Up Sissy Gets Wanked Off

Tied Up Sissy Gets Wanked Off

XHamster 3 years ago

TANGENTOD - Stretching and Filling Fuckpet Holes With Strap

TANGENTOD - Stretching and Filling Fuckpet Holes With Strap

Pervclips 1 week ago

Sexy Shemale in Corset does Ass to mouth

Sexy Shemale in Corset does Ass to mouth

XHamster 11 months ago

becomingfemme - bambii mercedes sissy maids job is never done until he cums down her throat of course

becomingfemme - bambii mercedes sissy maids job is never done until he cums down her throat of course

TransDoe 2 years ago

Painful ruined orgasm cbt for my bondaged sub sissy whore

Painful ruined orgasm cbt for my bondaged sub sissy whore

XHamster 5 years ago

Hairy Bear sucks black dick so good

Hairy Bear sucks black dick so good

XHamster 2 months ago

Sophia Loreen Private Show

53% HD 2:00 / 8:40

Sophia Loreen Private Show

Camster 1 month ago

I'm Man in Nice Lady's Figure 💌

I'm Man in Nice Lady's Figure 💌

WebcamBros 10 months ago

Insatiable Sissy Melody Sluts Out with a Huge Dildo

Insatiable Sissy Melody Sluts Out with a Huge Dildo

XHamster 2 years ago

Sissyboy Cuckold Slave Training Pegging First Time

Sissyboy Cuckold Slave Training Pegging First Time

XHamster 5 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 1 week ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 5 days ago

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

PissVids 1 year ago

I make a pact

XHamster 3 months ago

Trans Sissy Whore tutored by Mastix Murmur compilation

Trans Sissy Whore tutored by Mastix Murmur compilation

Amateur8 7 months ago

Petra,s 8th training

Petra,s 8th training

XHamster 1 year ago

Black BBW TRANSSEXUAL Threesome With TRANSSEXUAL Carmen Masters & TRANSSEXUAL Patra.. Uncircumcised BIG BLACK DICK Dual Internal cum shot!

Black BBW TRANSSEXUAL Threesome With TRANSSEXUAL Carmen Masters & TRANSSEXUAL Patra.. Uncircumcised BIG BLACK DICK Dual Internal cum shot!

MyTransfix 4 days ago

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

TrannyGem 4 years ago

Sophia Loreen Party on Jun 18, 2026 - Part 4

54% HD 2:00 / 58:05

Sophia Loreen Party on Jun 18, 2026 - Part 4

Camster 1 month ago

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

XHamster 3 years ago

Lika Kai Private Show

Lika Kai Private Show

Camster 1 week ago

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

4Gay 1 year ago

Having a Hard Time - Shemale Jane Jerks off to Larissa's Ass in Classroom

Having a Hard Time - Shemale Jane Jerks off to Larissa's Ass in Classroom

XHamster 1 month ago

Sissy Sadie trains his crossdresser to be a sissy with his upskirt practice

Sissy Sadie trains his crossdresser to be a sissy with his upskirt practice

GayVD 1 day ago

Pet Amber Shock gets her tight ass destroyed by Ciren Verde & Lora Cross in wild anal sex tape

Pet Amber Shock gets her tight ass destroyed by Ciren Verde & Lora Cross in wild anal sex tape

TrannyMovs 1 month ago

Trinity CUMSLUT

Trinity CUMSLUT

XHamster 4 months ago

Training a Twink Femboy Noisy Ass with BBC

Training a Twink Femboy Noisy Ass with BBC

XHamster 2 weeks ago

feminisation training

feminisation training

ShemaleSin 7 months ago

Dude fucks tied-up slave

Dude fucks tied-up slave

Some.Porn 2 years ago

Korra Del Rio's workout leads to steamy hardcore session with trainer

Korra Del Rio's workout leads to steamy hardcore session with trainer

WeGotDicks 1 month ago

You

HD 0:19 / 11:34

IWantClips 1 month ago

Tatiana & Lord Private Show

56% HD 2:00 / 9:23

Tatiana & Lord Private Show

Camster 2 weeks ago

Too Tempting to Look Away.

Too Tempting to Look Away.

Camster 3 weeks ago

Slut Training with a Trans Mistress

49% HD 0:12 / 17:32

Slut Training with a Trans Mistress

IWantClips 1 month ago

The intern is trained in the office

The intern is trained in the office

XHamster 2 months ago

Mommy teasing sissy cock.

Mommy teasing sissy cock.

XHamster 3 months ago

Femdom Real Couple female domination pegging & ding-knob mastix & sissy cuck feminization FULL movie scene

Femdom Real Couple female domination pegging & ding-knob mastix & sissy cuck feminization FULL movie scene

Dafreeporn 1 year ago

Sasha De Sade Sissy Inspection Hot!

Sasha De Sade Sissy Inspection Hot!

TrannyGem 7 years ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

XHamster 2 years ago

Petra the horny little shedevil

Petra the horny little shedevil

XHamster 2 months ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 3

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 3

XHamster 1 year ago

Fun Trans Cheerleader Plays with Her Soft Cock

Fun Trans Cheerleader Plays with Her Soft Cock

XHamster 6 months ago

Corporate Futa Training

Corporate Futa Training

Tranny.one 3 years ago

Sophia Loreen Private Show

64% HD 2:00 / 15:34

Sophia Loreen Private Show

Camster 3 weeks ago

Rigid a-hole Teaching Of t-model

Rigid a-hole Teaching Of t-model

TrannyGem 6 years ago

Submitted and Shown off

Submitted and Shown off

XHamster 1 month ago

Dimitry Rolex & Liliith Private Show

66% HD 2:00 / 23:20

Dimitry Rolex & Liliith Private Show

Camster 2 years ago

Beauties of Anal Delights for the Female Superiority Society (part 2).

Beauties of Anal Delights for the Female Superiority Society (part 2).

XHamster 1 year ago

Anal Slut fisting training dildo

Anal Slut fisting training dildo

XHamster 10 months ago

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Jenny

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Jenny

XHamster 4 years ago

put two mitts in the booty of her sissy fuckslut. handballing

put two mitts in the booty of her sissy fuckslut. handballing

TrannyGem 3 years ago

Wear a Perverted Costume and Have Someone Accompany You to Training

Wear a Perverted Costume and Have Someone Accompany You to Training

XHamster 1 year ago

Compilation of Tgirls Training their Dudes with Bareback Tranny Fucks, Lingerie, and Big Asses in Compilation

Compilation of Tgirls Training their Dudes with Bareback Tranny Fucks, Lingerie, and Big Asses in Compilation

TrannyMovs 4 days ago

T-Girl tugging and screaming

T-Girl tugging and screaming

TrannyGem 3 years ago

Nicolle & Christian Private Show

63% HD 2:00 / 5:47

Nicolle & Christian Private Show

Camster 11 months ago

Sissy Super-Bitch gets Torn Up by BIG BLACK COCK

Sissy Super-Bitch gets Torn Up by BIG BLACK COCK

TrannyGem 3 years ago

Experienced Shemale Trains A Chap

Experienced Shemale Trains A Chap

AShemaleTube 15 years ago

Goddess Rosie: Serve My Every Desire so Sweetly

Goddess Rosie: Serve My Every Desire so Sweetly

XHamster 8 months ago

Arab Sissy Crossdresser MIKAH deepthroats her FATTEST BIG BLACK COCK Parent Lollipop at Motel Guest room - Uber-sexy CD BLOW-JOB

Arab Sissy Crossdresser MIKAH deepthroats her FATTEST BIG BLACK COCK Parent Lollipop at Motel Guest room - Uber-sexy CD BLOW-JOB

TransTube.tv 1 year ago

BDSM domina pissing over sub's face in kitchen after trampling

BDSM domina pissing over sub's face in kitchen after trampling

Some.Porn 2 years ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

XHamster 2 years ago

Sissy Femboy gets a Passionate Dildo Fuck from British Mistress Couple

Sissy Femboy gets a Passionate Dildo Fuck from British Mistress Couple

XHamster 5 days ago

Jenifer worships Mommy Ruby cock

Jenifer worships Mommy Ruby cock

XHamster 6 months ago

Ryu Doll Gets her Insides Scrambled by BBC

Ryu Doll Gets her Insides Scrambled by BBC

ShemaleSin 5 years ago

you are my sissy whore and will pimp you out !!!

you are my sissy whore and will pimp you out !!!

XHamster 2 years ago

Feminization of a Bad Roommate

Feminization of a Bad Roommate

XHamster 2 weeks ago

Trans Woman trains you to gargle man rod, kicking off fragile but then predominant you and boinking your face

Trans Woman trains you to gargle man rod, kicking off fragile but then predominant you and boinking your face

Transvids.tv 1 year ago

Stepmother helps her horny sissy stepson cum hard

Stepmother helps her horny sissy stepson cum hard

XHamster 2 years ago

Sissy Secretary Maddy Riding My Big Black Dildo's And Gaping My Ass

Sissy Secretary Maddy Riding My Big Black Dildo's And Gaping My Ass

XHamster 8 months ago

Cute Shemale in Fishnets Locked in Chastity Cage BBC dildo doing Anal Training

Cute Shemale in Fishnets Locked in Chastity Cage BBC dildo doing Anal Training

XHamster 5 days ago

”Maria Kazi Trains Her Anus For Huge Cock”

”Maria Kazi Trains Her Anus For Huge Cock”

TransHero 7 months ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

XHamster 1 year ago

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

XHamster 1 year ago

At Her Mercy: Hot Trans Domme Trains You

At Her Mercy: Hot Trans Domme Trains You

XHamster 1 year ago

Sissy Slut Gangbang Training

Sissy Slut Gangbang Training

XHamster 2 days ago

Rah Teach

TrannyGem 4 years ago

Sissy going testicles deep

Sissy going testicles deep

WebcamBros 4 days ago

TS Nadia Love dominated by Goddess Tangent

TS Nadia Love dominated by Goddess Tangent

XHamster 2 months ago

Dressed in Drag for Girls Night Out

Dressed in Drag for Girls Night Out

XHamster 3 weeks ago

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

XHamster 10 months ago

XXL Anal Destruction for Crossdressers

XXL Anal Destruction for Crossdressers

XHamster 1 year ago

Diminutive Top Trans Goth Woman Pulverizes Male Masturbator Fucky-fucky Plaything Till Yam-sized Pop-shot and Ahegao Eye Spin

Diminutive Top Trans Goth Woman Pulverizes Male Masturbator Fucky-fucky Plaything Till Yam-sized Pop-shot and Ahegao Eye Spin

TransTube.tv 1 year ago

BNWO Sissy Bride Gooning

BNWO Sissy Bride Gooning

XHamster 10 months ago

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

WebcamBros 1 year ago

Sophia Loreen Private Show

HD 2:00 / 15:39

Sophia Loreen Private Show

Camster 1 week ago

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

XHamster 7 months ago

Sissy Femboy teaching

Sissy Femboy teaching

TransTube.tv 4 days ago

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

PissVids 1 year ago

Orgy and trains of the CentoXCento with the trans Sabrina Pa

Orgy and trains of the CentoXCento with the trans Sabrina Pa

XHamster 4 years ago

Asian Submissive Ladyboy First Anal Casting & Slave Training

Asian Submissive Ladyboy First Anal Casting & Slave Training

XHamster 1 month ago

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

XHamster 1 year ago

A quickie in the bathroom before datenight

A quickie in the bathroom before datenight

XHamster 4 years ago

Amateur subduing male subject

Amateur subduing male subject

Some.Porn 8 months ago

Sissy slut has monthly release: cum on the gagball, wears it eating her own cum and locks herself in chastity

Sissy slut has monthly release: cum on the gagball, wears it eating her own cum and locks herself in chastity

XHamster 6 months ago

HERMAPHRODITE ON educate

HERMAPHRODITE ON educate

TransTube.tv 1 year ago

Sophia Loreen Party on Jul 17, 2026 - Part 4

63% HD 2:00 / 43:44

Sophia Loreen Party on Jul 17, 2026 - Part 4

Camster 2 weeks ago

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

XHamster 5 months ago

Rubdown your weapons with a jizm coated sole approach

Rubdown your weapons with a jizm coated sole approach

Gayhub 11 months ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Eporner 1 year ago

Double cumshot, in my mouth and anal orgasm with all my toys

Double cumshot, in my mouth and anal orgasm with all my toys

XHamster 7 months ago

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

SortPorn 1 year ago

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

XHamster 10 months ago

Becoming Her

XHamster 4 months ago

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

FreePorn8 1 year ago

Alexxa A Private Show

Alexxa A Private Show

Camster 1 week ago

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

XHamster 7 months ago

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

XHamster 1 week ago

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