Training Videos - Trans (89,070)

Drag Queen and Woman Makeover Transformation - Foundation and Eye Shadow

Drag Queen and Woman Makeover Transformation - Foundation and Eye Shadow

xHamster 1 year ago

Bambi Sissy Transformation (Sissy Caption Story)

Bambi Sissy Transformation (Sissy Caption Story)

SortPorn 4 years ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 1 year ago

Sissy Transition CLINIC - Obedience Training

Sissy Transition CLINIC - Obedience Training

xHamster 1 year ago

parris jake daniel jake daniel gets trained again

parris jake daniel jake daniel gets trained again

PornOne 1 year ago

How Badly You Want to Worship My Phat Ass?

70% HD 2:00 / 13:31

How Badly You Want to Worship My Phat Ass?

Flirt4Free 1 year ago

Tranny girl gives sock footjob after sport! Cumshot on her hot leggings ass!

Tranny girl gives sock footjob after sport! Cumshot on her hot leggings ass!

xHamster 2 years ago

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

TrannyGem 3 years ago

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

xHamster 4 months ago

charlotte sins jade venus zariah aura victoria grant lesbian in training

charlotte sins jade venus zariah aura victoria grant lesbian in training

PornOne 4 months ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

ShemaleSin 5 months ago

Talia Hot Private Show

Talia Hot Private Show

Flirt4Free 1 week ago

Confused sissy boys transformed by big black cock feminization trainer (bbc) with captions

Confused sissy boys transformed by big black cock feminization trainer (bbc) with captions

XXXShemalePorn 1 year ago

Femboy vs Penetrate-machine

Femboy vs Penetrate-machine

4Gay 1 month ago

BlacKate Gets Slut Training

BlacKate Gets Slut Training

Nuvid 2 months ago

Sissy Candy locked onto her faux-cock stand compilation

Sissy Candy locked onto her faux-cock stand compilation

TrannyGem 1 year ago

Jhordy & Maxx Private Show

46% HD 2:00 / 1:47:48

Jhordy & Maxx Private Show

Flirt4Free 8 months ago

Thippy Top Training

Thippy Top Training

PornUse 6 months ago

A Little Femboy Destroys His Ass with a Hard Anal, Swallows Piss and Swallows Cum

A Little Femboy Destroys His Ass with a Hard Anal, Swallows Piss and Swallows Cum

xHamster 1 month ago

loser training chastity spreading

loser training chastity spreading

Nuvid 2 weeks ago

Dimitri Caruso Private Show

57% HD 2:00 / 9:59

Dimitri Caruso Private Show

Flirt4Free 4 years ago

Jhordy & Maxx Private Show

42% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 8 months ago

angry conservative wife discovers your sissy secret!

55% HD 0:36 / 8:55

angry conservative wife discovers your sissy secret!

PornBox 6 days ago

becomingfemme - harlee chanel workplace distraction with sissy training

becomingfemme - harlee chanel workplace distraction with sissy training

TransDoe 2 years ago

Chastity Sissy Maid Service Training With Ria Bentley

Chastity Sissy Maid Service Training With Ria Bentley

ShemaleSin 5 months ago

Sisk Fuck Her Ass Wiht Pinky Dildo

Sisk Fuck Her Ass Wiht Pinky Dildo

xHamster 1 year ago

This Pathetic Slut Loves Can NOT Stop Cumming & Eating It After!

This Pathetic Slut Loves Can NOT Stop Cumming & Eating It After!

xHamster 1 year ago

Brunette Sissy in Chastity and Fishnets Rides Dildo

Brunette Sissy in Chastity and Fishnets Rides Dildo

xHamster 1 year ago

Shemale sex slave cums from prostate massage and fingering

Shemale sex slave cums from prostate massage and fingering

XGroovy 1 year ago

Jhordy & Maxx Private Show

54% HD 2:00 / 24:57

Jhordy & Maxx Private Show

Flirt4Free 8 months ago

FUTA LESBIANS CONVERT YOU shemales hunt and convert you

57% HD 0:10 / 38:18

FUTA LESBIANS CONVERT YOU shemales hunt and convert you

LoyalFans 3 months ago

Luccas & Jhordy Private Show

43% HD 2:00 / 18:11

Luccas & Jhordy Private Show

Flirt4Free 11 months ago

cropping high high-heeled slippers cock ball torture sissy teaching

cropping high high-heeled slippers cock ball torture sissy teaching

TrannyGem 2 years ago

[metavulgar] - sissy training, exposing, sissy humiliation, panty, collar, collar and leash - full version on my patreon page - sissy, joi, cuckold, findom

[metavulgar] - sissy training, exposing, sissy humiliation, panty, collar, collar and leash - full version on my patreon page - sissy, joi, cuckold, findom

ShemaleSin 8 months ago

Chubby Mistress bends Him over to grab His balls and gives a rough Handjob

Chubby Mistress bends Him over to grab His balls and gives a rough Handjob

xHamster 1 year 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 1 year ago

The Mistress Fucks in the Ass with a Strap-on

The Mistress Fucks in the Ass with a Strap-on

xHamster 3 months ago

Troy Khalil Private Show

HD 2:00 / 18:10

Troy Khalil Private Show

Flirt4Free 2 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

Squirt Like a Girl

54% 0:11 / 5:27

Squirt Like a Girl

Clips4sale 2 years ago

Sissy Assfucking Instructing and Jizm Guzzling

Sissy Assfucking Instructing and Jizm Guzzling

TrannyGem 4 years ago

Master & Christian & Nicco Private Show

46% HD 2:00 / 14:59

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

The sirs piss makes me jism and unload urinate at the same time. Customized by worshippers

The sirs piss makes me jism and unload urinate at the same time. Customized by worshippers

Gayhub 9 months ago

Hairy Tranny Fucked Hard

Hairy Tranny Fucked Hard

Eporner 1 year ago

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

xHamster 1 year ago

Sluts Academy - Newest Student - Dee Angels - So Happy to Please You!!!

Sluts Academy - Newest Student - Dee Angels - So Happy to Please You!!!

xHamster 1 year ago

Learning How to Be a Good Sissy

Learning How to Be a Good Sissy

xHamster 9 months ago

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

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

TransHero 3 years ago

So hot cumming after 7 days in chastity and anal training

So hot cumming after 7 days in chastity and anal training

xHamster 1 year ago

Trinity CUMSLUT

Trinity CUMSLUT

xHamster 3 weeks ago

INTOLERABLE EDGING

INTOLERABLE EDGING

WebcamBros 3 months ago

Carlo Bicci Private Show

Carlo Bicci Private Show

Flirt4Free 2 years ago

Tranny camgirl training her butt and throat

Tranny camgirl training her butt and throat

XXXShemalePorn 4 years ago

Bashful Lara plays with 2 PLAYTHINGS and CRAMS FUCKHOLE with UNDIES

Bashful Lara plays with 2 PLAYTHINGS and CRAMS FUCKHOLE with UNDIES

5Gays 6 months ago

Cum twice while riding huge corn

Cum twice while riding huge corn

xHamster 4 months ago

Trans Girl Fucks a Pumpkin

Trans Girl Fucks a Pumpkin

xHamster 1 week ago

Ken Prince Gets His Ass Smashed With A 25CM Thick Cucumber

Ken Prince Gets His Ass Smashed With A 25CM Thick Cucumber

xHamster 2 months ago

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

TrannyGem 4 years ago

SometimesNiki dildos in crotchless panties

SometimesNiki dildos in crotchless panties

xHamster 1 year ago

FemGape Creamy Big Anal Training With Dildo

FemGape Creamy Big Anal Training With Dildo

TubeOn 2 months ago

Fucked by Old Man Behind the Scenes

60% 1:01 / 28:00

Fucked by Old Man Behind the Scenes

FapHouse 1 year ago

Sissy Maid Dildo Training Part: 1

Sissy Maid Dildo Training Part: 1

xHamster 2 years ago

Trap ride big dildo deep anal 4k ( sissy femboy anal training doggystyle )

Trap ride big dildo deep anal 4k ( sissy femboy anal training doggystyle )

Pornzona 3 weeks ago

Feelipe & Adara Private Show

62% HD 2:00 / 12:01

Feelipe & Adara Private Show

Flirt4Free 9 months ago

Adele & Eccatelina Private Show

61% HD 2:00 / 4:57

Adele & Eccatelina Private Show

Flirt4Free 3 years ago

Watch two naughty damsels-in-training get their tight holes drilled by a hot young stud

Watch two naughty damsels-in-training get their tight holes drilled by a hot young stud

TrannyMovs 1 week ago

Sweet sissy ass tries two strapon cocks

Sweet sissy ass tries two strapon cocks

xHamster 1 year ago

Your sexy girly boy takes dildo deep in his pink hole

Your sexy girly boy takes dildo deep in his pink hole

xHamster 2 years ago

Trouble-free servant slut slave works his holes with a straight fuck master!

Trouble-free servant slut slave works his holes with a straight fuck master!

xHamster 2 years ago

Destroy My Hole

Destroy My Hole

xHamster 1 month ago

Sissy in black pvc

Sissy in black pvc

GayJack 8 months ago

Monica Farell Private Show

Monica Farell Private Show

Flirt4Free 2 years ago

Anal Orgasm in Chastity

Anal Orgasm in Chastity

xHamster 1 month ago

Liam & Jacob Private Show

63% HD 2:00 / 5:51

Liam & Jacob Private Show

Flirt4Free 1 year ago

Ghost Manifests whilst three Bbc Screw my Tranny Overweight Booty Until I Get an Anal Creampie and Pee on my little Rod

Ghost Manifests whilst three Bbc Screw my Tranny Overweight Booty Until I Get an Anal Creampie and Pee on my little Rod

SortPorn 1 week ago

Daphne Trans Shaking the Ass of a Naughty Femboy on the Male's Cock - Ai Arte

57% HD 0:39 / 2:06

Daphne Trans Shaking the Ass of a Naughty Femboy on the Male's Cock - Ai Arte

FapHouse 3 months ago

Why is she scared of femboy sissy's cumshot?

Why is she scared of femboy sissy's cumshot?

xHamster 3 years ago

Paul Walkers Private Show

61% 4K 2:00 / 5:36

Paul Walkers Private Show

Flirt4Free 8 months ago

trans sissy fleshlight fucking multiple orgasm compilation (preview!)

trans sissy fleshlight fucking multiple orgasm compilation (preview!)

Pornzona 3 weeks ago

Anime Uniform Femboy Jizzing in V-Card Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in V-Card Cell ~Oscar20xxx~

2BGay 2 years ago

Butt Slut Sunday 2

Butt Slut Sunday 2

xHamster 2 weeks ago

Patric & Oliver Private Show

69% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 3 years ago

Sissy Crossdresser cat walk training

Sissy Crossdresser cat walk training

xHamster 10 months ago

Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

Eporner 8 months ago

Lick Smell, and Worship My Hairy Armpits

62% HD 2:00 / 9:27

Lick Smell, and Worship My Hairy Armpits

Flirt4Free 3 years ago

Long dildo masturbation at the entrance of the apartment

Long dildo masturbation at the entrance of the apartment

TrannyGem 3 years ago

Cross Dresser slut jenni needs bbc whore training

Cross Dresser slut jenni needs bbc whore training

SexTubeSpot 5 years ago

Jasmine_dlight & Mistress Luciana - Vr180 Foot Fucking & Latex Footjob

Jasmine_dlight & Mistress Luciana - Vr180 Foot Fucking & Latex Footjob

FapHouse 1 month ago

Taking My Sissy-wife's Virginity - Pegging POV with Elle Eros

Taking My Sissy-wife's Virginity - Pegging POV with Elle Eros

xHamster 1 year ago

Sir's Obedient Pet

64% 0:10 / 16:29

Sir's Obedient Pet

Clips4sale 2 years ago

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

65% HD 0:39 / 30:56

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

FapHouse 4 months ago

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Transvids.tv 9 months ago

Desire Sweet Private Show

61% HD 2:00 / 10:38

Desire Sweet Private Show

Flirt4Free 4 months ago

Hawt Trans Beauty Fucked in Every Room of the House by TS Chick - Sexy Trans Lesbian Sex

Hawt Trans Beauty Fucked in Every Room of the House by TS Chick - Sexy Trans Lesbian Sex

Dafreeporn 5 months ago

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

ShemaleSin 1 year ago

Crhistian & Dereckk & Friends Duo Show (kissing and Hardcore Fucking)

HD 2:00 / 16:37

Crhistian & Dereckk & Friends Duo Show (kissing and Hardcore Fucking)

Flirt4Free 8 years ago

Making my sissy boy Cum for being a good girl!

Making my sissy boy Cum for being a good girl!

Pornzona 3 weeks ago

Felipe Guzman Private Show

Felipe Guzman Private Show

Flirt4Free 2 years 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 month ago

This Guy Made It Rain a Lot of Cum on My White Boy Face

63% HD 0:39 / 9:25

This Guy Made It Rain a Lot of Cum on My White Boy Face

FapHouse 1 year ago

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

TransTube.tv 1 year ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 7 years ago

Master & Chris & Jepsen Private Show

HD 2:00 / 30:28

Master & Chris & Jepsen Private Show

Flirt4Free 3 years ago

BBC Faggot Forever

BBC Faggot Forever

Clips4sale 1 year ago

Angie Mendoza Private Show

HD 2:00 / 13:32

Angie Mendoza Private Show

Flirt4Free 4 years ago

Painal

xHamster 3 years ago

Adele & Eccatelina Private Show

59% HD 2:00 / 13:33

Adele & Eccatelina Private Show

Flirt4Free 3 years ago

Sissy Slips Hatian BBC Unfathomable down Floozy Mouth

Sissy Slips Hatian BBC Unfathomable down Floozy Mouth

ShemaleSin 4 years ago

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

TrannyGem 4 years ago

Elia Blaine Sissy Training With Dildo On The Wall

Elia Blaine Sissy Training With Dildo On The Wall

Nuvid 2 months ago

Najayla Adams Private Show

Najayla Adams Private Show

Flirt4Free 4 years ago

AB104 Fucky-fucky fucktoy tester give up (Japanese and English subtitles)

AB104 Fucky-fucky fucktoy tester give up (Japanese and English subtitles)

Transvids.tv 1 year ago

Neomie Thompson Private Show

61% HD 2:00 / 6:15

Neomie Thompson Private Show

Flirt4Free 3 months ago

Scarlet Barbieri Private Show

Scarlet Barbieri Private Show

Flirt4Free 2 months ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

xHamster 1 year ago

Ftm Pegging

xHamster 3 months ago

That’s What Happened in the New Slave Welcome Room

47% HD 0:39 / 8:02

That’s What Happened in the New Slave Welcome Room

FapHouse 2 years ago

Desire Sweet Private Show

HD 2:00 / 17:58

Desire Sweet Private Show

Flirt4Free 1 month ago

Intro To Sissification 1 - Dress Up

60% 0:14 / 7:24

Intro To Sissification 1 - Dress Up

Clips4sale 2 years ago

Cum in my mouth, play with your cum, and swallow it, sexy, femboy, trans, gay naughty, tongue, sloopy, six pack, fitness teen

Cum in my mouth, play with your cum, and swallow it, sexy, femboy, trans, gay naughty, tongue, sloopy, six pack, fitness teen

xHamster 1 year ago

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