Training Videos - Trans (87,347)

Kira caught during self-bondage

Kira caught during self-bondage

xHamster 5 months ago

”Ruined Orgasms By Goddess Bare Feet”

”Ruined Orgasms By Goddess Bare Feet”

Zatube 1 year ago

Bulge and Strip Tease Show

HD 2:00 / 3:33:54

Bulge and Strip Tease Show

Flirt4Free 8 years ago

Cosplay Sissification KDA Evelynn Akali Leauge of Legends TEASER OmankoVivi

Cosplay Sissification KDA Evelynn Akali Leauge of Legends TEASER OmankoVivi

Pornfact 1 week ago

Roommate turns sissy crossdresser into her bitch

Roommate turns sissy crossdresser into her bitch

BigButtHoles 6 months ago

Bisexual Sluts with TS Kim Wagner

66% 4K 0:26 / 34:47

Bisexual Sluts with TS Kim Wagner

Clips4sale 1 year ago

I love fucking my husband in the ass

I love fucking my husband in the ass

xHamster 7 months ago

Jasmine Dlight & Hairy Kink Stepmother & Roxxie Sweetheart - Outdoor Fisting Gangbang - the Warmup

69% HD 1:01 / 10:44

Jasmine Dlight & Hairy Kink Stepmother & Roxxie Sweetheart - Outdoor Fisting Gangbang - the Warmup

FapHouse 6 months ago

Mrhankeys CLIP-CLOP 4XL first time

Mrhankeys CLIP-CLOP 4XL first time

xHamster 2 years ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

xHamster 1 month ago

Eat Cum Because You're Gay Jizz Tonguing Commands CEI ft Trans Female dominance

Eat Cum Because You're Gay Jizz Tonguing Commands CEI ft Trans Female dominance

TransTube.tv 1 year ago

Florance Wants to Be Loved

Florance Wants to Be Loved

FapHouse 1 year ago

Transgender in high heels and lingerie does anal beads

Transgender in high heels and lingerie does anal beads

xHamster 1 year ago

Re:Zero Rem Anal training and Blowjob part.2

Re:Zero Rem Anal training and Blowjob part.2

xHamster 3 years ago

Punished tiny dick by a Futanari Goddess - CBT, FUTA

57% 0:14 / 9:23

Punished tiny dick by a Futanari Goddess - CBT, FUTA

Clips4sale 8 months ago

Anal Training Night

Anal Training Night

xHamster 9 months ago

Jaw-dropping moment from "Crossdresser with fake tits gets worried by the sex machine"

Jaw-dropping moment from "Crossdresser with fake tits gets worried by the sex machine"

xHamster 6 months ago

Sabrina Smiith Private Show

63% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Aphrodite Adams Trains You The Foolish Basics

Aphrodite Adams Trains You The Foolish Basics

TrannyGem 4 months ago

My husband with a small cock fucks me

My husband with a small cock fucks me

xHamster 9 months ago

Straight Guys Love to be Called Faggots Goddess Vivien Make Me Bi Fantasy with futanari and cuckold talk for pussy free straight guys who crave cock!

4K 0:30 / 11:15

Straight Guys Love to be Called Faggots Goddess Vivien Make Me Bi Fantasy with futanari and cuckold talk for pussy free straight guys who crave cock!

Clips4sale 3 months ago

Training For Cock Worship Boys

Training For Cock Worship Boys

ShemaleSex 3 months ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

Ash Wish to Heal Real Quick to Have Sex with His Boy Friend Blake

Ash Wish to Heal Real Quick to Have Sex with His Boy Friend Blake

FapHouse 11 months ago

Obedient Puppy Gets Taunted and Pulverized

Obedient Puppy Gets Taunted and Pulverized

TrannyGem 1 year ago

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 3 months ago

squirt show

Flirt4Free 3 years ago

Crossdresser Trains with a Butt Plug

Crossdresser Trains with a Butt Plug

MenGem 10 months ago

”Nana : Fat Cock Bareback and Frottage”

”Nana : Fat Cock Bareback and Frottage”

TransHero 6 years ago

Leather Crossdresser Sissy trains his hole to the max

Leather Crossdresser Sissy trains his hole to the max

xHamster 7 months ago

TRANSFIXED - Interracial Trans And CIS Lesbian Nurses Have INSANE BAREBACK ORGY To Complete Training

TRANSFIXED - Interracial Trans And CIS Lesbian Nurses Have INSANE BAREBACK ORGY To Complete Training

xHamster 3 years ago

korean slim femboy drilled (utter movie on fansly)

korean slim femboy drilled (utter movie on fansly)

Gayhub 1 year ago

Sissygasm Tutorial - Sissification with the Lady of Feminization

Sissygasm Tutorial - Sissification with the Lady of Feminization

MatureTubeHere 3 years ago

Gabriella Bruni Private Show

60% 4K 2:00 / 6:17

Gabriella Bruni Private Show

Flirt4Free 4 months ago

Crossdresser in shiny skirt and stocking rides huge dildos to warm up his anal pussy

Crossdresser in shiny skirt and stocking rides huge dildos to warm up his anal pussy

xHamster 2 years ago

Transexual Ol Training Secrets for Ultimate Beauty Transformation Revealed!

Transexual Ol Training Secrets for Ultimate Beauty Transformation Revealed!

JAVHDTube 1 month ago

Sisk's Hand Made Anal Bead

Sisk's Hand Made Anal Bead

xHamster 10 months ago

AB097 Slutty nun degraded Sexual transformation -Edging,squeeze

AB097 Slutty nun degraded Sexual transformation -Edging,squeeze

xHamster 2 years ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 1 week ago

Cardi B Dazed by MASSSIVE 11” BIG BLACK COCK Trans Fuckpole So YAM-SIZED!!!!

Cardi B Dazed by MASSSIVE 11” BIG BLACK COCK Trans Fuckpole So YAM-SIZED!!!!

TransTube.tv 1 year ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 2 years ago

Key moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

Key moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

xHamster 4 months ago

MaureenNadh - Hijab Asian Skinny Squirting On Chastity While Dildo Ride.

MaureenNadh - Hijab Asian Skinny Squirting On Chastity While Dildo Ride.

xHamster 3 years ago

Sissy molly and her bbc daddy

Sissy molly and her bbc daddy

AbTranny 7 years ago

Scott Carterr & Michael Magno Private Show

HD 2:00 / 37:52

Scott Carterr & Michael Magno Private Show

Flirt4Free 2 years ago

Ohmibod Play

Flirt4Free 7 years ago

I Masturbated and Came in the Car After the Training

HD 0:39 / 14:40

I Masturbated and Came in the Car After the Training

FapHouse 5 months ago

Super Full Show

56% HD 2:00 / 22:12

Super Full Show

Flirt4Free 1 year ago

The Contract Fucker Part 1 (MP4 HD)

57% HD 0:30 / 8:18

The Contract Fucker Part 1 (MP4 HD)

Clips4sale 8 months ago

Kristy Butty Private Show

Kristy Butty Private Show

Flirt4Free 1 month ago

Jenny enjoying a fat cucumber 2

Jenny enjoying a fat cucumber 2

xHamster 5 months ago

Pussy Slamming!!

Pussy Slamming!!

xHamster 11 months ago

Elvis & Patric & Santiago Private Show

HD 2:00 / 15:49

Elvis & Patric & Santiago Private Show

Flirt4Free 1 year ago

”Summer Rayne - Summer Training”

”Summer Rayne - Summer Training”

TransHero 4 years ago

hot dominant goth gives you SPH whilst stroking BBC JOI

77% 0:20 / 5:38

hot dominant goth gives you SPH whilst stroking BBC JOI

Clips4sale 1 year ago

Bi MMF Anal trains c0mp

Bi MMF Anal trains c0mp

Eporner 1 year ago

Alizzz Storm Private Show

Alizzz Storm Private Show

Flirt4Free 11 months ago

Femmes Pub Gig six: A Sissy Feminization Series

Femmes Pub Gig six: A Sissy Feminization Series

TrannyGem 5 years ago

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

65% HD 1:01 / 11:20

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

FapHouse 2 years ago

Anal foams over machine for sexy crossdresser

Anal foams over machine for sexy crossdresser

xHamster 5 months ago

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

TrannyGem 9 months ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 2 years ago

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

TrannyGem 4 months ago

Sissy Training Her Holes

Sissy Training Her Holes

xHamster 1 year ago

Sophia Loreen Private Show

4K 2:00 / 24:23

Sophia Loreen Private Show

Flirt4Free 2 months ago

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

ShemaleSin 3 years ago

Sissy Femboy In Crimson Running In Rivulets Precum - Railing Massive Black Fucktoy

Sissy Femboy In Crimson Running In Rivulets Precum - Railing Massive Black Fucktoy

TrannyGem 3 years ago

Ass Worship and Anal Expression Sissy Class

Ass Worship and Anal Expression Sissy Class

xHamster 8 months ago

Marily Daniela Private Show

Marily Daniela Private Show

Flirt4Free 2 years ago

Floozy to the club in Amsterdam

Floozy to the club in Amsterdam

ShemaleSin 7 months ago

Traffic Light Gooner Training

HD 0:10 / 12:12

Traffic Light Gooner Training

LoyalFans 3 years ago

Sissygasm for Domina

Sissygasm for Domina

xHamster 7 months ago

Sissy trans get boink my a turkish stud

Sissy trans get boink my a turkish stud

TransTube.tv 9 months ago

貞操帯つけてディルドでアナル調教 ♡ chinese crossdresser getting off 女装子男の娘

貞操帯つけてディルドでアナル調教 ♡ chinese crossdresser getting off 女装子男の娘

TrannyGem 3 years ago

Breasty Trans Maid Gets Her Booty and Titties Drilled by Hung Housewife

Breasty Trans Maid Gets Her Booty and Titties Drilled by Hung Housewife

ShemaleSin 6 months ago

Sissy Compilation Outside drinking and pussy fuck in Public

Sissy Compilation Outside drinking and pussy fuck in Public

xHamster 7 months ago

New Violet Dildo for My Sissy Bitch

New Violet Dildo for My Sissy Bitch

xHamster 1 year ago

Sophia Loreen Party on Jan 24, 2026 - Part 2

4K 2:00 / 22:20

Sophia Loreen Party on Jan 24, 2026 - Part 2

Flirt4Free 1 month ago

Self-training No. 87 Fucking Car Drive

Self-training No. 87 Fucking Car Drive

FapHouse 1 month ago

Trained to Be Completely Subservient to Him

Trained to Be Completely Subservient to Him

xHamster 7 months ago

TS Slut milking

73% 0:30 / 14:31

TS Slut milking

Clips4sale 1 year ago

Sophia Loreen Party on Jul 1, 2025 - Part 2

50% HD 2:00 / 30:11

Sophia Loreen Party on Jul 1, 2025 - Part 2

Flirt4Free 8 months ago

Margaux Fox Private Show

HD 2:00 / 32:13

Margaux Fox Private Show

Flirt4Free 4 years ago

The Hostess Trains her Cross Dress Pegging Anal Spunk Fountain-Chinese Femdom

The Hostess Trains her Cross Dress Pegging Anal Spunk Fountain-Chinese Femdom

Dafreeporn 5 years ago

Sissy Asshole Destroyed by Massive Dragon Dildo

HD 1:01 / 11:52

Sissy Asshole Destroyed by Massive Dragon Dildo

FapHouse 3 days ago

The Last Virgin of 2025

The Last Virgin of 2025

Clips4sale 1 month ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 1 week ago

Ladyboy jack off encouragement

Ladyboy jack off encouragement

TrannyGem 2 years ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

Rainblow 1 year ago

Paul Ear & Tatiana Private Show

61% HD 2:00 / 16:37

Paul Ear & Tatiana Private Show

Flirt4Free 5 months ago

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

xHamster 6 months ago

I woke up aroused with the fantasy for shaft

I woke up aroused with the fantasy for shaft

TrannyGem 6 months ago

Piss slut for domina crossdressers mistresses

Piss slut for domina crossdressers mistresses

aShemaleTube 2 years ago

Aya Anderson Private Show

HD 2:00 / 13:29

Aya Anderson Private Show

Flirt4Free 9 months ago

Slut Training Part 1

62% HD 1:01 / 6:18

Slut Training Part 1

FapHouse 2 years ago

Cock Whore Sissy's Training Night (Audio Erotica)

Cock Whore Sissy's Training Night (Audio Erotica)

xHamster 3 years ago

Jhon & Derek & Chris Private Show - Part 2

66% HD 2:00 / 5:56

Jhon & Derek & Chris Private Show - Part 2

Flirt4Free 3 years ago

Rebeccah Gibson Private Show

HD 2:00 / 46:05

Rebeccah Gibson Private Show

Flirt4Free 11 hours ago

add me on snapchat-surfer.69

add me on snapchat-surfer.69

Eporner 6 years ago

Alexander & Master & Patric Private Show

55% HD 2:00 / 1:39:58

Alexander & Master & Patric Private Show

Flirt4Free 3 years ago

Sexy Transgirl intercourse with dominatrix, Ladyboy Nutting Cowgirl Railing Gigantic bone, Sissy spunk

Sexy Transgirl intercourse with dominatrix, Ladyboy Nutting Cowgirl Railing Gigantic bone, Sissy spunk

TrannyGem 1 year ago

Submissive Training III

42% HD 0:10 / 10:29

Submissive Training III

LoyalFans 6 months ago

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

4K 0:11 / 33:28

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

Clips4sale 1 month ago

Emerald & Natalya Private Show

Emerald & Natalya Private Show

Flirt4Free 2 years ago

Richii Smiith Private Show

4K 2:00 / 13:28

Richii Smiith Private Show

Flirt4Free 1 month ago

Shemale from India getting gangbanged on a train Latina Tranny

Shemale from India getting gangbanged on a train Latina Tranny

xHamster 6 months ago

Celeste & Liz Private Show

63% HD 2:00 / 4:37

Celeste & Liz Private Show

Flirt4Free 3 years ago

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

xHamster 2 years ago

Crhistian & Dereckk & Friends Party on Oct 28, 2018 - Part 4

65% HD 2:00 / 52:18

Crhistian & Dereckk & Friends Party on Oct 28, 2018 - Part 4

Flirt4Free 7 years ago

Plugged Shemale Gooning for over Half an Hour

Plugged Shemale Gooning for over Half an Hour

ShemaleSin 11 months ago

Sandra Jizz Private Show

66% 4K 2:00 / 15:51

Sandra Jizz Private Show

Flirt4Free 9 months ago

Training my sissys clitty and urethra! Exceedingly unfathomable urethral 50cm/nineteen.68 all the way with ejaculation!

Training my sissys clitty and urethra! Exceedingly unfathomable urethral 50cm/nineteen.68 all the way with ejaculation!

ShemaleSin 1 year ago

Troy Khalil Private Show

HD 2:00 / 28:06

Troy Khalil Private Show

Flirt4Free 2 years ago

Big Ass Samus Femboy Anal Pounded by Two Big Black Cocks

Big Ass Samus Femboy Anal Pounded by Two Big Black Cocks

xHamster 1 month ago

White Sissy Femboy Rides Big Dildo

White Sissy Femboy Rides Big Dildo

xHamster 10 months ago

Perseo & Dafne Private Show

64% HD 2:00 / 9:32

Perseo & Dafne Private Show

Flirt4Free 1 year ago

The banging machine is nearly tearing my butt apart, it feels so priceless

The banging machine is nearly tearing my butt apart, it feels so priceless

ShemaleSin 1 week ago

I will do a sexy dance while I nude for you AS THE HOT FIRE I AM WITH MY POLLA

I will do a sexy dance while I nude for you AS THE HOT FIRE I AM WITH MY POLLA

Flirt4Free 5 years ago

Breaking Bunni - Goth FemDom trans Gangbang | OverlordJupiter, Lady Vi, Mistress Celene, Dusti Bunni

Premium HD 30:10

Breaking Bunni - Goth FemDom trans Gangbang | OverlordJupiter, Lady Vi, Mistress Celene, Dusti Bunni

Clips4sale 1 year ago

Sandy Nell Private Show

69% HD 2:00 / 4:00

Sandy Nell Private Show

Flirt4Free 3 years ago

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