Training Videos - Trans (29,248)

Trying New Fist Dildo and Get Fucked and Fisted

Trying New Fist Dildo and Get Fucked and Fisted

xHamster 1 year ago

Sissy slut crossdresser gets dominated in sexy dress

Sissy slut crossdresser gets dominated in sexy dress

FapNFuck 1 year ago

I Love Playing, General Rehersal for More

HD 0:39 / 16:21

I Love Playing, General Rehersal for More

FapHouse 3 days ago

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

Faptor 2 years ago

BLACKED Hot Blond Ash Hollywood Cheats with Her BBC Tutor

BLACKED Hot Blond Ash Hollywood Cheats with Her BBC Tutor

Dafreeporn 6 years ago

sissypov - bunny summers transgirl beta bedtime fantasy

sissypov - bunny summers transgirl beta bedtime fantasy

TransDoe 2 years ago

trans zariah and Victoria and Jade and female Charlotte lesbo in training 3 trans hotties and one female have joy foursome

trans zariah and Victoria and Jade and female Charlotte lesbo in training 3 trans hotties and one female have joy foursome

ShemaleSin 3 months ago

He fucks me like a bitch... I love being trained by Master - @Sasha_de_Sade & @AxelReigns

He fucks me like a bitch... I love being trained by Master - @Sasha_de_Sade & @AxelReigns

aShemaleTube 1 year ago

Sissy Faux-cock Buttfuck Teaching

Sissy Faux-cock Buttfuck Teaching

TrannyGem 1 week ago

Reina Hanno Anal Kegel Training Trailer

Reina Hanno Anal Kegel Training Trailer

xHamster 3 years ago

Sissys Breast Pumping Session Enlarging my boobs

Sissys Breast Pumping Session Enlarging my boobs

xHamster 3 months ago

Sissy Crossdresser gets BIG facial cumshot from Grindr Parent

Sissy Crossdresser gets BIG facial cumshot from Grindr Parent

TransTube.tv 1 year ago

Mistress Trains Her Sissy Gurls

Mistress Trains Her Sissy Gurls

BeMyHole 5 years ago

Be My Bride's Maid of Honor

Be My Bride's Maid of Honor

PornSigma 2 years ago

Mistress Wearing Latex Gloves Milks Sissy

Mistress Wearing Latex Gloves Milks Sissy

xHamster 2 years ago

”Cock Training At The Gym With PAWG Kiara Edwards”

”Cock Training At The Gym With PAWG Kiara Edwards”

TransHero 3 months ago

Super Depreciate Couple

Super Depreciate Couple

FapHouse 2 years ago

Relent to Your Trans Mistress

Relent to Your Trans Mistress

xHamster 1 month ago

Crystal's Stripping Practice Session 1

Crystal's Stripping Practice Session 1

PornFreeNow 1 week ago

QOS Sissy Lola Crystals gets 2nd internal cumshot from SUPREME-SIZED BIG BLACK COCK Fuckbuddy

QOS Sissy Lola Crystals gets 2nd internal cumshot from SUPREME-SIZED BIG BLACK COCK Fuckbuddy

TransTube.tv 1 year ago

Sucking Training with Ada Wong - Taker POV Futa 3D Hentai Animation

Sucking Training with Ada Wong - Taker POV Futa 3D Hentai Animation

HentaiGem 1 year ago

Feminization - Sissyfication - Sissy teaching - Support for the sissy

Feminization - Sissyfication - Sissy teaching - Support for the sissy

TrannyGem 1 year ago

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

Gayhub 5 months ago

Jadan puts the hot in yoga

Jadan puts the hot in yoga

Some.Porn 1 year ago

Staying Plugged for a Long Time After Ruining My Pussy for 10 Hours

Staying Plugged for a Long Time After Ruining My Pussy for 10 Hours

xHamster 3 months ago

pretty Step Sissters Toying With Eachother while mummy Gone, salacious cleft Slurping, Fuck-fest

pretty Step Sissters Toying With Eachother while mummy Gone, salacious cleft Slurping, Fuck-fest

Transvids.tv 6 months ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

70% HD 1:01 / 10:12

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

FapHouse 1 year ago

Train

xHamster 8 years ago

Bikini Sissy Femboy Jerks Cock Till Gushing Cum Destroyed Mess

Bikini Sissy Femboy Jerks Cock Till Gushing Cum Destroyed Mess

JuicyTrans 6 days ago

Anal Slut Training With Clarice Boaventura

Anal Slut Training With Clarice Boaventura

DrTuber 2 months ago

Self-Directed Training No64 Rope Tied Exposed Walk at Night

Self-Directed Training No64 Rope Tied Exposed Walk at Night

xHamster 3 months ago

Self-training No.71 Punishment Training Chair

Self-training No.71 Punishment Training Chair

xHamster 2 months ago

Hattabi4ik super-steamy massive booty phat gold rain and cum-shot steaming ginormous compilation

Hattabi4ik super-steamy massive booty phat gold rain and cum-shot steaming ginormous compilation

TrannyGem 1 year ago

My femboy stepbrother learns to suck dicks

My femboy stepbrother learns to suck dicks

xHamster 11 months ago

POV Hard Pegging Jasmine Dlight From Mistress

POV Hard Pegging Jasmine Dlight From Mistress

xHamster 5 months ago

”Arm Wrestling Prick For A Piece Of Booty - Whitney Wright, Roman Todd, Jade Venus”

”Arm Wrestling Prick For A Piece Of Booty - Whitney Wright, Roman Todd, Jade Venus”

Zatube 1 year ago

Navy dude nude queer and tranny army romping hardcore A kinky instructing day ends with

Navy dude nude queer and tranny army romping hardcore A kinky instructing day ends with

GayCK 7 years ago

Feminized Plow Fucktoy four Life

Feminized Plow Fucktoy four Life

TrannyGem 4 years ago

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

TransTube.tv 1 year ago

Slut Training Part 1

Slut Training Part 1

xHamster 2 years ago

Anal Trany

xHamster 6 days ago

The Ultimate Chastity Cage Review and Guide Video

63% HD 1:01 / 37:26

The Ultimate Chastity Cage Review and Guide Video

FapHouse 2 years ago

My Ultimate Fantasy, Pegging Step Brother.

My Ultimate Fantasy, Pegging Step Brother.

Pornzona 2 days ago

Sissy bitch crossdresser get screwed

Sissy bitch crossdresser get screwed

2BGay 2 years ago

Uber-uber-cute Transgirl Assets-suit Try-On - Trans Figure Positivity Butt Full salute Gorgeous

Uber-uber-cute Transgirl Assets-suit Try-On - Trans Figure Positivity Butt Full salute Gorgeous

TransTube.tv 1 year ago

Trans spunk profusely after a ravage in the urethra

Trans spunk profusely after a ravage in the urethra

TrannyGem 9 months ago

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Eporner 1 year ago

AB080 新春特辑-玉兔淫春(中英字幕)女王.深喉.假阳具.开高叉.手淫.射精.丝袜.高跟

AB080 新春特辑-玉兔淫春(中英字幕)女王.深喉.假阳具.开高叉.手淫.射精.丝袜.高跟

TransTube.tv 1 year ago

Sissy Blowjob Cumslut Anal Fantasy - Lick and Fuck

Sissy Blowjob Cumslut Anal Fantasy - Lick and Fuck

TrannyGem 7 years ago

Uk crossdresser in training 3

Uk crossdresser in training 3

GayCK 2 years ago

TRANSSEXUAL Dominatrix predominates Jerk Off Instructions

TRANSSEXUAL Dominatrix predominates Jerk Off Instructions

TrannyGem 11 months ago

Ashley V swallows huge dildo up her ass and rubs her tiny caged clitAshley V se traga un enorme consolador

Ashley V swallows huge dildo up her ass and rubs her tiny caged clitAshley V se traga un enorme consolador

xHamster 2 years ago

Kendall Penny Sissy Training Wih Cumshot Reward

Kendall Penny Sissy Training Wih Cumshot Reward

Nuvid 2 months ago

Hard Sissy Training Use and Cum

Hard Sissy Training Use and Cum

xHamster 5 months ago

Sissy latexdoll pissing and anal training

Sissy latexdoll pissing and anal training

xHamster 4 years ago

Destroy My Asshole Huge Inflatable Anal Dildo Sissy Training - Full Video on LayneLovee Manyvids

Destroy My Asshole Huge Inflatable Anal Dildo Sissy Training - Full Video on LayneLovee Manyvids

xHamster 2 years ago

Mistress Reina with Her Slave Sissy Kanisa Part1: Anal Training

Mistress Reina with Her Slave Sissy Kanisa Part1: Anal Training

xHamster 1 year ago

TS Training

xHamster 1 year ago

Let’s do workout jointly! I'll teach my booty, u teach your knob! JOI by Tgirl beauty GERMAN

Let’s do workout jointly! I'll teach my booty, u teach your knob! JOI by Tgirl beauty GERMAN

FreePorn8 2 weeks 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

Humiliating Cock Sucking Training for Sissy

Humiliating Cock Sucking Training for Sissy

Tranny.one 4 years ago

Chastity Sissy Slut Anal Training Dice Game Jessica Blo

Chastity Sissy Slut Anal Training Dice Game Jessica Blo

Eporner 4 months ago

Strapon sloppy throat training slave earns cum facial

Strapon sloppy throat training slave earns cum facial

Pornzona 1 week ago

Hot Girls Fucking Guys with Strapons FEMDOM PEGGING PANTYHOSE ANAL

Hot Girls Fucking Guys with Strapons FEMDOM PEGGING PANTYHOSE ANAL

FreePorn8 6 years ago

Test XXL butt-plug ass-pipe , ass-fuck dilatation instructing

Test XXL butt-plug ass-pipe , ass-fuck dilatation instructing

TrannyGem 4 months ago

Independent Training No72 Punishment Training Chair Part 2

Independent Training No72 Punishment Training Chair Part 2

xHamster 3 months ago

Trash Bottom Anal Training Starter NoAudio

Trash Bottom Anal Training Starter NoAudio

xHamster 4 weeks ago

Sexy sissy Ponyboy Showing his nude body and high heels

Sexy sissy Ponyboy Showing his nude body and high heels

xHamster 4 years ago

Sissy Riding Two Different Dildos

Sissy Riding Two Different Dildos

xHamster 1 year ago

Try not to cum with this sexy transvestite from Italy.

Try not to cum with this sexy transvestite from Italy.

Fapality 2 years ago

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

PePorn 3 months ago

vagina training

vagina training

ShemaleSin 3 days ago

Subscribers take turns getting dominated by Dominus Rider in hot homemade video

Subscribers take turns getting dominated by Dominus Rider in hot homemade video

GayVD 1 month ago

Sph and Sissification for Slut! Arya Grander and Mistress Priest

Sph and Sissification for Slut! Arya Grander and Mistress Priest

xHamster 1 year ago

BNWO Sissy Bride Gooning

BNWO Sissy Bride Gooning

xHamster 6 months ago

sissy fucks herself with a dildo in a chastity belt using her cum as a lubricant

sissy fucks herself with a dildo in a chastity belt using her cum as a lubricant

Pornzona 1 month ago

On the beach I turn my husband's cock into pussy

On the beach I turn my husband's cock into pussy

xHamster 2 years ago

Claire Tenebrarum & Natalie Mars take turns training each other with toys

Claire Tenebrarum & Natalie Mars take turns training each other with toys

TrannyMovs 4 months ago

Best Post Orgasm Torture of All Time! - Luxie Pink

Best Post Orgasm Torture of All Time! - Luxie Pink

xHamster 4 years ago

Preping my Puppy Loona for her stroking

Preping my Puppy Loona for her stroking

TrannyGem 1 year ago

Sissy Crossdresser Cuckhold Spanked, Fastened, Gagged, And Chastised By Hawt Femdom Mistresse

Sissy Crossdresser Cuckhold Spanked, Fastened, Gagged, And Chastised By Hawt Femdom Mistresse

BigTitsLust 5 years ago

Spectacular moment from "Crossdresser Rough anal fuck with rock hard red monster dildo"

Spectacular moment from "Crossdresser Rough anal fuck with rock hard red monster dildo"

xHamster 8 months ago

Mistress Kara pegging her sissy bitch boi - check out my links for full video

Mistress Kara pegging her sissy bitch boi - check out my links for full video

Pornzona 1 day ago

Chastity JOI From Tranny Girl for Small Penis Loser! Ruined Orgasm! German Deutsch

63% HD 1:01 / 7:11

Chastity JOI From Tranny Girl for Small Penis Loser! Ruined Orgasm! German Deutsch

FapHouse 2 months ago

Extreme sissy training

Extreme sissy training

aShemaleTube 2 years ago

Public walk like a real sissy whore

Public walk like a real sissy whore

xHamster 1 month ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Lesbian8 9 months ago

Sissy Fisting

HD 1:01 / 14:20

FapHouse 6 months ago

”TGIRLJAPAN HARDCORE: Julia Winston & Rone”

”TGIRLJAPAN HARDCORE: Julia Winston & Rone”

Trashreality 1 year ago

On Your Knees Dickblower

On Your Knees Dickblower

TrannyGem 4 years ago

Walking Street Freelancer

Walking Street Freelancer

Some.Porn 1 year ago

Training Tgirl sex fetish Ronnie to dress slutty for BBCs.

Training Tgirl sex fetish Ronnie to dress slutty for BBCs.

AbGay 1 year ago

Sissy PLUMB in the WOODS

Sissy PLUMB in the WOODS

TrannyGem 3 years ago

Caged Sissy Begs for Release - Magic Wand Tease Until She Cums Hard

Caged Sissy Begs for Release - Magic Wand Tease Until She Cums Hard

xHamster 8 months ago

TRAINING SISSY ANAL SLUT FOR GODDESS VD JOI

TRAINING SISSY ANAL SLUT FOR GODDESS VD JOI

BeMyHole 5 years ago

Femboy music movie - sissy dance in pink panty

Femboy music movie - sissy dance in pink panty

ShemaleSin 2 years ago

Milk Your Transgirl EPISODE

Milk Your Transgirl EPISODE

ShemaleSin 4 years ago

Becoming A Sissy (JOI) w/ Raven Gray

Becoming A Sissy (JOI) w/ Raven Gray

Amateur8 3 years ago

Sissy Conversion Therapy - Part 1

HD 1:01 / 10:59

Sissy Conversion Therapy - Part 1

FapHouse 7 months ago

Onanism perceives too superb.I can't stand it...♡ chinese crossdresser

Onanism perceives too superb.I can't stand it...♡ chinese crossdresser

TrannyGem 3 years ago

BBC Huge Sissygasm

BBC Huge Sissygasm

xHamster 6 months ago

Lily Starlet Clitty gets her tight ass drilled against the box in kinky BDSM session

Lily Starlet Clitty gets her tight ass drilled against the box in kinky BDSM session

TrannyMovs 4 weeks ago

Anal Gape Training My Greedy Femboy Sissy Cum Dump

Anal Gape Training My Greedy Femboy Sissy Cum Dump

xHamster 2 years ago

Sissy Crossdresser TRAINING

Sissy Crossdresser TRAINING

Pornzona 1 month ago

Mind Cracking PPS Jerk Off Instructions with Spirals - Sadism & masochism Marionette Teaching

Mind Cracking PPS Jerk Off Instructions with Spirals - Sadism & masochism Marionette Teaching

Gayhub 10 months ago

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Transvids.tv 9 months ago

Natalie Mars Training the baby Gimp xhfqin

Natalie Mars Training the baby Gimp xhfqin

FetishShrine 2 years ago

Junker Queen Bent Mei Over the Gym Equipment - Personal Training, Junker Style

Junker Queen Bent Mei Over the Gym Equipment - Personal Training, Junker Style

xHamster 1 week ago

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

61% HD 1:01 / 23:31

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

FapHouse 2 months ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

Amateur8 3 months ago

Plapping Cumshot And Cum Swallow Locktober Sissy Slut Jessica Bloom

Plapping Cumshot And Cum Swallow Locktober Sissy Slut Jessica Bloom

xHamster 5 months ago

Huge 9in Dildo Fucking Compilation Vol.4

Huge 9in Dildo Fucking Compilation Vol.4

xHamster 8 months ago

3rd training session of 13 02 2026 - 30 minutes

3rd training session of 13 02 2026 - 30 minutes

xHamster 2 months ago

2 huge hands free cumshots in a row

2 huge hands free cumshots in a row

xHamster 1 year ago

Spanking and anal dildo training for sissy shemale from her femdom mistress

Spanking and anal dildo training for sissy shemale from her femdom mistress

XCafe 2 years ago

WVM - PART 36 - SUCK MY THUMB By MissKitty2K

WVM - PART 36 - SUCK MY THUMB By MissKitty2K

xHamster 1 year ago

My Hermaphroditism Tennis Schoolteacher Instructs Me Rigid Everyday

My Hermaphroditism Tennis Schoolteacher Instructs Me Rigid Everyday

HentaiGem 2 months ago

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

xHamster 1 year ago

Finale: Rectal fuck stick plumb with spandex socks 20210801-six

Finale: Rectal fuck stick plumb with spandex socks 20210801-six

TrannyGem 4 years ago

Kira caught during self-bondage

Kira caught during self-bondage

xHamster 6 months ago

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