Training Videos - Trans (87,412)

Latina with Cockring and Lush

HD 2:00 / 57:47

Latina with Cockring and Lush

Flirt4Free 7 years ago

Sissy Fag Tranny Training Self Help

Sissy Fag Tranny Training Self Help

Eporner 5 years ago

Petra,s Valentine date ❤️

Petra,s Valentine date ❤️

xHamster 1 year ago

ohww... Blake is Loving Me So Much - The Lust of Sissy Boy Saga

ohww... Blake is Loving Me So Much - The Lust of Sissy Boy Saga

xHamster 1 year ago

misr4 - Riding anal dildo in black stockings

misr4 - Riding anal dildo in black stockings

xHamster 6 months ago

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Premium HD 8:05

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Sheer 3 years ago

Pissy Sissy

65% HD 0:25 / 18:02

Clips4sale 6 months ago

Slut Training the Dragon dildo

Slut Training the Dragon dildo

xHamster 2 months ago

Patricia Wolford - Machine self anal training

Patricia Wolford - Machine self anal training

ShemaleSin 7 months ago

StacXXXs & TsLaylaDollBbw Night Of Fun

52% HD 0:10 / 24:03

StacXXXs & TsLaylaDollBbw Night Of Fun

LoyalFans 2 years ago

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

TransTube.tv 1 year ago

Sissy training

xHamster 3 years ago

Trannies in training - (Episode #07)

HD 0:39 / 31:30

Trannies in training - (Episode #07)

FapHouse 4 years ago

Charlie Cano Private Show

HD 2:00 / 15:20

Charlie Cano Private Show

Flirt4Free 3 years ago

Anal training for Sissy Blaire_18. Dominatrix Nika inserts anal beads into her Sissy's little ass.

Anal training for Sissy Blaire_18. Dominatrix Nika inserts anal beads into her Sissy's little ass.

xHamster 1 year ago

Crhistian & Dereckk & Friends Party on Jul 20, 2019

HD 2:00 / 43:40

Crhistian & Dereckk & Friends Party on Jul 20, 2019

Flirt4Free 6 years ago

Lingerie Sissy Candy Is Locked on Her Dildo Stand in Bondage and Cums with Vibrator

Lingerie Sissy Candy Is Locked on Her Dildo Stand in Bondage and Cums with Vibrator

aShemaleTube 2 months ago

Naughty num worshipping the church of cock

65% 0:39 / 5:28

Naughty num worshipping the church of cock

FapHouse 1 year ago

Diego Phoenix Private Show

4K 2:00 / 13:55

Diego Phoenix Private Show

Flirt4Free 4 months ago

You Love My Leather Pants [Femdom Chastity Trans Sissy]

You Love My Leather Pants [Femdom Chastity Trans Sissy]

LoyalFans 4 months ago

Sissy Bride Riding Her Doll

Sissy Bride Riding Her Doll

xHamster 6 months ago

Brazilian tgirl slut training💋💘

Brazilian tgirl slut training💋💘

aShemaleTube 1 year ago

Training to become a sissy cuckold

Training to become a sissy cuckold

xHamster 2 years ago

Roy is a the Best Bottom

50% HD 2:00 / 9:57

Roy is a the Best Bottom

Flirt4Free 3 years ago

Trans Anal Training Cumming Twice From Monster Sex tool Hard And Caged

Trans Anal Training Cumming Twice From Monster Sex tool Hard And Caged

Lesbian8 1 month ago

Photographer Dana Delvey Dominates Her Model

HD 0:10 / 18:40

Photographer Dana Delvey Dominates Her Model

LoyalFans 2 months ago

I caught you crossdressed at the mall now you will enjoyment my male friends JOI CEI ANAL PLAY

I caught you crossdressed at the mall now you will enjoyment my male friends JOI CEI ANAL PLAY

Dafreeporn 2 years ago

Hawt Angels Pumping Boys with Strapons FEMDOM PEGGING HOSE ANAL

Hawt Angels Pumping Boys with Strapons FEMDOM PEGGING HOSE ANAL

SortPorn 5 years ago

Totk-002 Training And Massive Swallowing! Transsexual-loving Pervert Maniac Orgy Circle Aise Mei

Totk-002 Training And Massive Swallowing! Transsexual-loving Pervert Maniac Orgy Circle Aise Mei

getTranny 1 year ago

Mikes Hanon Private Show

55% HD 2:00 / 26:39

Mikes Hanon Private Show

Flirt4Free 3 years ago

As they say... "Practice makes perfect"

As they say... "Practice makes perfect"

xHamster 3 years ago

Hot Fuck After Training On The Beach

Hot Fuck After Training On The Beach

BeMyHole 3 years ago

Doggy Training Part 2

Doggy Training Part 2

xHamster 1 year ago

Edging with oil

HD 0:39 / 23:58

Edging with oil

FapHouse 5 years ago

AB023 Beautiful femboy training by sexy Mistress 艾爷被女王调教用粗黑屌抽插爽翻

AB023 Beautiful femboy training by sexy Mistress 艾爷被女王调教用粗黑屌抽插爽翻

aShemaleTube 5 years ago

Alexxa A Private Show

66% HD 2:00 / 5:09

Alexxa A Private Show

Flirt4Free 2 weeks ago

Self-Training No94 Wearing Sanitary Napkins and Tampons and Taking an Exposed Walk Part 1

Self-Training No94 Wearing Sanitary Napkins and Tampons and Taking an Exposed Walk Part 1

xHamster 1 month ago

Instruction From the Trainer No6 Exposure Masturbation in the Parking Lot in Front of the Store

HD 0:39 / 13:01

Instruction From the Trainer No6 Exposure Masturbation in the Parking Lot in Front of the Store

FapHouse 1 week ago

Instructions From the Trainer No. 25 Outdoor Anal Play 2

55% HD 1:01 / 11:17

Instructions From the Trainer No. 25 Outdoor Anal Play 2

FapHouse 2 months ago

Sissy In Tartan Outfit Trying Several Dildos

Sissy In Tartan Outfit Trying Several Dildos

xHamster 9 months ago

Her Place Is Wherever He Wants Her to Be

Her Place Is Wherever He Wants Her to Be

FapHouse 1 month ago

shemale/female lesbian ass Training With Mandy Mitchell And Bianca Stone

shemale/female lesbian ass Training With Mandy Mitchell And Bianca Stone

AbTranny 6 years ago

Yasmin training session

Yasmin training session

KeekAss 2 years ago

Cameltoe or rubber pussy? - Sissification & Feminization with Lady Julina

Cameltoe or rubber pussy? - Sissification & Feminization with Lady Julina

Pornzona 1 week ago

Sissy Kanisa Maid Service Ep1: Lock Dick Before Start Work

Sissy Kanisa Maid Service Ep1: Lock Dick Before Start Work

FapHouse 4 months ago

Submissive ass preparation

Submissive ass preparation

xHamster 7 months ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 12 hours ago

FUCKERMAN - Cumpussy By MissKitty2K

FUCKERMAN - Cumpussy By MissKitty2K

xHamster 1 year ago

Helicopter Duo

Flirt4Free 1 year ago

Kaled & Lian Private Show

66% HD 2:00 / 17:56

Kaled & Lian Private Show

Flirt4Free 3 years ago

INTOLERABLE EDGING

INTOLERABLE EDGING

Gayhub 3 months ago

FetishEmmanuella video 4 - Garbage Prostitute - part 3

FetishEmmanuella video 4 - Garbage Prostitute - part 3

xHamster 6 months ago

Sissy Hoe Lola Crystals worshipping monster fat black spear

Sissy Hoe Lola Crystals worshipping monster fat black spear

TrannyGem 3 years ago

Buttfuck climax forearms-free-for-all getting ravaged by a door

Buttfuck climax forearms-free-for-all getting ravaged by a door

Gayhaus 3 months ago

Diosa trans dominante te habla sucio, te usa y controla tu mente de sumiso

Diosa trans dominante te habla sucio, te usa y controla tu mente de sumiso

ShemaleSin 1 week ago

Nicole Enjoys Spitroast Machine Training

Nicole Enjoys Spitroast Machine Training

PornUse 4 months ago

Elix & Elias & Paulo Private Show

54% HD 2:00 / 6:45

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Charlie Cano Private Show

Charlie Cano Private Show

Flirt4Free 3 years ago

Jessica Liam Private Show

HD 2:00 / 43:27

Jessica Liam Private Show

Flirt4Free 2 months ago

Panties CEI - Masturbation Instructions Wearing Panties, Pre-Cum Licking & Self-Facial - Loser Position Cum Eating Instruction - White Lingerie, Stockings & Garter Belt - A Femdom POV Clip by Leda von Thrill - HD Video MP4 1920 x 1080p

40% HD 0:25 / 14:05

Panties CEI - Masturbation Instructions Wearing Panties, Pre-Cum Licking & Self-Facial - Loser Position Cum Eating Instruction - White Lingerie, Stockings & Garter Belt - A Femdom POV Clip by Leda von Thrill - HD Video MP4 1920 x 1080p

Clips4sale 2 years ago

Gagging Trans Beauty Melody Gets Throat Rammed in Intense Face Fuck

Gagging Trans Beauty Melody Gets Throat Rammed in Intense Face Fuck

Jizzberry 1 year ago

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

xHamster 9 months ago

Sissy Intense Anal Fucking with Rockhard Monstercock

Sissy Intense Anal Fucking with Rockhard Monstercock

xHamster 1 month ago

”Those are five nasty creampies!”

”Those are five nasty creampies!”

TransHero 2 months ago

AB073 Abby instructing gimp and jizz shot (Restrain Bondage ,wire,anal invasion hook,manmeat instructing edging )

AB073 Abby instructing gimp and jizz shot (Restrain Bondage ,wire,anal invasion hook,manmeat instructing edging )

TrannyGem 3 years ago

Training A TS Stewardess

56% HD 0:30 / 36:00

Training A TS Stewardess

AEBN 4 years ago

Girl Love Fuck Crossdresser

Girl Love Fuck Crossdresser

FapHouse 1 week ago

Big Model Muscled Bodybuilder Flexing Show

52% HD 2:00 / 10:24

Big Model Muscled Bodybuilder Flexing Show

Flirt4Free 9 years ago

My husband became a sissy in a chastity cage

My husband became a sissy in a chastity cage

xHamster 2 years ago

Young Allie North CD wet molten teenager

Young Allie North CD wet molten teenager

TrannyGem 9 months ago

Self-Training No19 Exposure Home from the Park

Self-Training No19 Exposure Home from the Park

xHamster 3 months ago

Trans on a Fuckmachine for Her Neighbor

Trans on a Fuckmachine for Her Neighbor

xHamster 5 months ago

Feelipe & Adara Private Show

62% HD 2:00 / 5:01

Feelipe & Adara Private Show

Flirt4Free 7 months ago

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

xHamster 1 year ago

[Trans POINT OF VIEW] Val Drains Herself Until She Jizzes On Camera, Blows a Adorable Goopy Femboy Load

[Trans POINT OF VIEW] Val Drains Herself Until She Jizzes On Camera, Blows a Adorable Goopy Femboy Load

TransTube.tv 1 year ago

Sissy Slut Fucked And Drained Stage 1 (WMV)

Sissy Slut Fucked And Drained Stage 1 (WMV)

Clips4sale 2 months ago

Reina Hanno Stretches Anal with Jelly Dildo and Cums

HD 0:39 / 24:49

Reina Hanno Stretches Anal with Jelly Dildo and Cums

FapHouse 1 month ago

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

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

LesbianBliss 3 days ago

SHEMALE MIND PROGRAM - Phase 1

HD 0:10 / 11:02

SHEMALE MIND PROGRAM - Phase 1

LoyalFans 1 week ago

Danie Priet & Jho Grisal Private Show

HD 2:00 / 15:39

Danie Priet & Jho Grisal Private Show

Flirt4Free 3 years ago

Emo Sissy Smoking Fetish & Solo Dance — POINT OF VIEW Crossdresser in Pantyhose

Emo Sissy Smoking Fetish & Solo Dance — POINT OF VIEW Crossdresser in Pantyhose

Gayhub 3 months ago

nun trains sissy to orgasm without hands!!

50% 0:06 / 2:19

nun trains sissy to orgasm without hands!!

PornBox 1 year ago

Sophia Loreen Party on Sep 19, 2025 - Part 3

68% 4K 2:00 / 58:36

Sophia Loreen Party on Sep 19, 2025 - Part 3

Flirt4Free 5 months ago

Nicco & Patric & Santiago Have Amazing Threesome

64% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 1 year ago

Halloween Killer Angel Sissy Superslut Lola getting mouth penetrated by big black cock

Halloween Killer Angel Sissy Superslut Lola getting mouth penetrated by big black cock

TransTube.tv 1 year ago

Sophia Loreen Party on May 7, 2022

HD 2:00 / 1:12:03

Sophia Loreen Party on May 7, 2022

Flirt4Free 3 years ago

Pony Man rod + Ravage Machine +- Getting Smashed with BIG BLACK COCK

Pony Man rod + Ravage Machine +- Getting Smashed with BIG BLACK COCK

4Gay 11 months ago

After training

xHamster 1 year ago

Luke Hardy & Cristian Ford Private Show

67% 4K 2:00 / 20:35

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 month ago

SisK Feminization Training with Cutie Pinky Seifuku EP3: Anal Play

SisK Feminization Training with Cutie Pinky Seifuku EP3: Anal Play

xHamster 2 years ago

Bend over the sofa and fuck your brain out KellyAErick DianaMILF

Bend over the sofa and fuck your brain out KellyAErick DianaMILF

Tranny.one 3 years ago

Large Schlongs in my litle BOOTY

Large Schlongs in my litle BOOTY

ShemaleSin 4 years ago

I Came to the BDSM Room in the Hope That You Will Spank Me Here

I Came to the BDSM Room in the Hope That You Will Spank Me Here

Flirt4Free 1 year ago

$Hey guys, let\'s have fun today, send 50cr and you\'ll receive a surprise ❤️❤️ LUHS ON, play with me😊 - Part 10$ HD 2:00 / 9:53

Hey guys, let\'s have fun today, send 50cr and you\'ll receive a surprise ❤️❤️ LUHS ON, play with me😊 - Part 10

Flirt4Free 9 months ago

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

xHamster 1 year ago

Full: Femboy in Yoga Pants Fucking Her Fat Ass with BBC Dildo and Gets an Anal Creampie

HD 0:39 / 12:19

Full: Femboy in Yoga Pants Fucking Her Fat Ass with BBC Dildo and Gets an Anal Creampie

FapHouse 3 weeks ago

Clyster for sissy

Clyster for sissy

TrannyGem 7 months ago

Solve The Riddle - Pt 1 - The Riddle By MissKitty2K

Solve The Riddle - Pt 1 - The Riddle By MissKitty2K

xHamster 1 year ago

Hard Femdom SISSY TRAINING COMPILATION! Cumshots

Hard Femdom SISSY TRAINING COMPILATION! Cumshots

ShemaleSin 5 years ago

”Trans Sergeant Jessy Dubai Trains Her New Recruits”

”Trans Sergeant Jessy Dubai Trains Her New Recruits”

LesbianBliss 1 week ago

Fpov - Goddess Amy Being a Shemale to Suck Cock - Cumshot

Fpov - Goddess Amy Being a Shemale to Suck Cock - Cumshot

xHamster 1 year ago

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TrannyGem 4 months ago

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

HD 0:39 / 15:09

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

FapHouse 6 months ago

Training My Sissy Bitch Gagging Her On 9 Inch Dick & Chockin

Training My Sissy Bitch Gagging Her On 9 Inch Dick & Chockin

xHamster 5 years ago

Sissy husband dressed up, bent over and pegged in his worthless ass

Sissy husband dressed up, bent over and pegged in his worthless ass

xHamster 2 years ago

”Sissy Hoe Spanking Discipline #FemdomRAW”

”Sissy Hoe Spanking Discipline #FemdomRAW”

TransHero 1 week ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 2 months ago

sissy ravages herself with a faux-cock in a v-card belt using her spunk as a lube

sissy ravages herself with a faux-cock in a v-card belt using her spunk as a lube

TrannyGem 4 months ago

Smoke Sub to a Shemale

Smoke Sub to a Shemale

TrannyGem 1 year ago

Andrea & Taty Private Show

Andrea & Taty Private Show

Flirt4Free 2 months ago

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

xHamster 7 months ago

How's the Cumshot From Your Angle Zack?

40% HD 0:39 / 6:30

How's the Cumshot From Your Angle Zack?

FapHouse 6 months ago

Luke Hardy & Cristian Ford Private Show - Part 7

57% 4K 2:00 / 5:05

Luke Hardy & Cristian Ford Private Show - Part 7

Flirt4Free 7 months ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

Amateur8 1 month ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 10:57

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 week ago

A Latex Fuck Doll Gets Strapped on by Femdom Women

61% HD 1:01 / 21:27

A Latex Fuck Doll Gets Strapped on by Femdom Women

FapHouse 3 months ago

FROM ALPHA TO BARBIE BIMBO

HD 0:10 / 13:06

FROM ALPHA TO BARBIE BIMBO

LoyalFans 1 year ago

Petra,s 10th training

Petra,s 10th training

aShemaleTube 7 months ago

Trans Slut Gets Fucked in the Hard Ass - Intense Deep Anal

Trans Slut Gets Fucked in the Hard Ass - Intense Deep Anal

xHamster 2 weeks ago

Amber Burnt Private Show

Amber Burnt Private Show

Flirt4Free 2 years ago

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