Training Videos - Trans (87,436)

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

TrannyGem 4 years ago

Jizzing for Diddy in Amsterdam

Jizzing for Diddy in Amsterdam

TrannyGem 5 months ago

busty sissy does the whore at the bus stop

busty sissy does the whore at the bus stop

xHamster 2 years ago

nude pathetic white thrall during outdoor party entertain guests, got enema, ejaculation, sex toy in homosexual booty, CMNM

nude pathetic white thrall during outdoor party entertain guests, got enema, ejaculation, sex toy in homosexual booty, CMNM

SortPorn 2 months ago

Agustus & Alan & Master & Santiago Private Show - Part 2

58% HD 2:00 / 29:23

Agustus & Alan & Master & Santiago Private Show - Part 2

Flirt4Free 1 year ago

Winterxxdoll Slut Training With Blowjob

Winterxxdoll Slut Training With Blowjob

YepTube 1 month ago

Get ready to be feminized and dominated by a big dicked stud in POV

Get ready to be feminized and dominated by a big dicked stud in POV

TrannyMovs 2 months ago

becomingfemme - linda moon much sexier than most women

becomingfemme - linda moon much sexier than most women

TransDoe 2 years ago

Sensual Teasing and Pillow Riding

56% HD 2:00 / 7:10

Sensual Teasing and Pillow Riding

Flirt4Free 2 years ago

Sensual fuck and masturbation POV scenes compilation

Sensual fuck and masturbation POV scenes compilation

XGroovy 5 years ago

Sissy Hope, Naughty Play Online with Naughty Daddy

Sissy Hope, Naughty Play Online with Naughty Daddy

xHamster 1 year ago

Kendal Smithx Private Show

Kendal Smithx Private Show

Flirt4Free 3 days ago

Sissy Femboy Bondage Feminization Training

Sissy Femboy Bondage Feminization Training

xHamster 10 months ago

FEM SCHEDULE: A WEEKEND 1080P

FEM SCHEDULE: A WEEKEND 1080P

LoyalFans 2 months ago

Bedtime for Sissy Taylor

Bedtime for Sissy Taylor

xHamster 3 weeks ago

Upskirt, takes her mini-skirt off

Upskirt, takes her mini-skirt off

TrannyGem 1 year ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 2 weeks ago

Trans Aspen Brooks trains Mickey OBriens tight ass with her fat cock

Trans Aspen Brooks trains Mickey OBriens tight ass with her fat cock

MenGem 2 months ago

Sophia Loreen Private Show - Part 3

66% 4K 2:00 / 6:09

Sophia Loreen Private Show - Part 3

Flirt4Free 9 months ago

Dominant Blk Trans w/ 11” inches BIG BLACK COCK Bully Dallas Vixen Controlling The Tramps

Dominant Blk Trans w/ 11” inches BIG BLACK COCK Bully Dallas Vixen Controlling The Tramps

TransTube.tv 1 year ago

Public walk like a real sissy whore

Public walk like a real sissy whore

xHamster 5 days ago

”TGIRLS XXX - STEPMOM Eris Jolie On Her Kitchen Masturbates”

”TGIRLS XXX - STEPMOM Eris Jolie On Her Kitchen Masturbates”

ThePornstar 1 year ago

Sissy Francis Malice Hismith Sex Machine Speed Video

63% HD 0:39 / 5:16

Sissy Francis Malice Hismith Sex Machine Speed Video

FapHouse 1 year ago

”Personal Trainer Fucks The Hell Out Of A T-Hottie”

”Personal Trainer Fucks The Hell Out Of A T-Hottie”

Rainblow 1 year ago

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

59% HD 1:01 / 26:04

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

FapHouse 1 year ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

xHamster 2 months ago

Humiliation! Lipstick on my BIG Fake Lips

Humiliation! Lipstick on my BIG Fake Lips

xHamster 7 months ago

squirt... - Part 3

squirt... - Part 3

Flirt4Free 6 days ago

in the butt, I like it fat, I rail to ejaculation

in the butt, I like it fat, I rail to ejaculation

TrannyGem 6 months ago

Biotch Teaching Jism Licking 1

Biotch Teaching Jism Licking 1

TrannyGem 4 years ago

Sissy Slut Clit Milked

Sissy Slut Clit Milked

xHamster 4 months ago

Sophia Loreen Party on Feb 25, 2026 - Part 3

4K 2:00 / 34:17

Sophia Loreen Party on Feb 25, 2026 - Part 3

Flirt4Free 6 days ago

Kim & Sammy Private Show

HD 2:00 / 27:24

Kim & Sammy Private Show

Flirt4Free 5 years ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 1 day ago

Slut Training Maxine X Double Stuffed in All Holes

HD 1:01 / 48:11

Slut Training Maxine X Double Stuffed in All Holes

FapHouse 2 weeks ago

Extreme sissy training

Extreme sissy training

aShemaleTube 2 years ago

Instruction from the trainer No 12 Exposure walk in the sports park

Instruction from the trainer No 12 Exposure walk in the sports park

xHamster 3 months ago

Feeling Dominated by My Shemale hentai Girlfriend Evelyn

Feeling Dominated by My Shemale hentai Girlfriend Evelyn

ShemaleSin 10 months ago

Your Cock and Balls Are Mine!! Dominant CBT Jo by Trannyi! German Deutsch

HD 0:39 / 12:19

Your Cock and Balls Are Mine!! Dominant CBT Jo by Trannyi! German Deutsch

FapHouse 1 month ago

Two Amazing Girls Show Off Their Hot Bodies.

38% HD 2:00 / 7:35

Two Amazing Girls Show Off Their Hot Bodies.

Flirt4Free 3 years ago

I'm Fucking This Sissy While Her Wife Is Out Shopping

I'm Fucking This Sissy While Her Wife Is Out Shopping

xHamster 2 weeks ago

CHECKING PEGGING SISSY HOLES

CHECKING PEGGING SISSY HOLES

aShemaleTube 7 months ago

Extraordinary Sissy Bad Dragon Gaping and FemDom Gap Destruction with Speculum Show Off by Mistresse Mercer

Extraordinary Sissy Bad Dragon Gaping and FemDom Gap Destruction with Speculum Show Off by Mistresse Mercer

ShemaleSin 3 months ago

Roxanne Roulette Spank Ass Long Masturbate Anal Play

HD 2:00 / 47:43

Roxanne Roulette Spank Ass Long Masturbate Anal Play

Flirt4Free 9 years ago

Luccas & Jhordy & Master Private Show

HD 2:00 / 12:18

Luccas & Jhordy & Master Private Show

Flirt4Free 2 weeks ago

Pissing in Chastity Cage

Pissing in Chastity Cage

FapHouse 1 year ago

Trans gal TSAVIVA self fulfillment caboose-ravage & cash-shot teaser

Trans gal TSAVIVA self fulfillment caboose-ravage & cash-shot teaser

TransTube.tv 1 year ago

Hottest sissy's booty in white underware

Hottest sissy's booty in white underware

ShemaleSin 2 years ago

Yoruichi SISSY Training Part 3 Joi Cei Cbt (Dildo, Blowjob,Crossdress,CHASTITY, Orgasm Denial, RUINED ORGASM, SELF FACIAL CUM EATING)

Yoruichi SISSY Training Part 3 Joi Cei Cbt (Dildo, Blowjob,Crossdress,CHASTITY, Orgasm Denial, RUINED ORGASM, SELF FACIAL CUM EATING)

XVideos 3 years ago

Sissygasm Tutorial - Sissification with the Lady of Feminization

Sissygasm Tutorial - Sissification with the Lady of Feminization

MatureTubeHere 3 years ago

My First Stream - Deep Anal Toys Riding Squirt Inflatable Rose Giant Toys Part 2

My First Stream - Deep Anal Toys Riding Squirt Inflatable Rose Giant Toys Part 2

xHamster 10 months ago

Intern Trains On Pietra Candy's Trans Ass

Intern Trains On Pietra Candy's Trans Ass

FapHouse 3 years ago

Femdom Mistress Goddess V Humiliates & Fully Feminizes Chastity Cuckold Sissy sub Slave W/ SPH 1/3

Femdom Mistress Goddess V Humiliates & Fully Feminizes Chastity Cuckold Sissy sub Slave W/ SPH 1/3

TatBabes 1 year ago

Fitness Influencer Gets Creampied During a Training Session

57% HD 0:39 / 2:01:05

Fitness Influencer Gets Creampied During a Training Session

FapHouse 2 months ago

Training a slave

Training a slave

aShemaleTube 3 years ago

OnlyFans - Crystal Thayer - Personal Anal Training With

OnlyFans - Crystal Thayer - Personal Anal Training With

VivaTube 7 months ago

Chastity Loving Cock Slut Deep Riding Big Daddy Dildo

Chastity Loving Cock Slut Deep Riding Big Daddy Dildo

xHamster 2 years ago

Whiteboi Jes fuck BBC Dildo

Whiteboi Jes fuck BBC Dildo

xHamster 3 weeks ago

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

HD 1:01 / 27:11

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

FapHouse 3 months ago

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

ShemaleSin 2 years ago

”TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!”

”TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!”

Zatube 1 year ago

Sissy Charlotte learns to deepthroat large wang

Sissy Charlotte learns to deepthroat large wang

MatureTubeHere 4 years ago

Sissy Surrender: Cucked and Controlled in My Whispering Chambers by Findom Goaldigger

Sissy Surrender: Cucked and Controlled in My Whispering Chambers by Findom Goaldigger

xHamster 4 months ago

Sissy mega-slut snow bunny Lola getting torn up and creampied by big black cock

Sissy mega-slut snow bunny Lola getting torn up and creampied by big black cock

TrannyGem 3 years ago

See-through Shirt Pussy Tease

66% HD 2:00 / 30:02

See-through Shirt Pussy Tease

Flirt4Free 4 years ago

Brand New Ts Hotness: Introducing Sunshyne Monroe

AbTranny 9 years ago

Exploring Pleasures

72% HD 1:01 / 9:26

Exploring Pleasures

FapHouse 11 months ago

Sissy instructions for my slut!!

Sissy instructions for my slut!!

xHamster 1 year ago

Bi Slaves Bareback - Blowjobs and Arse Fucking

Bi Slaves Bareback - Blowjobs and Arse Fucking

xHamster 1 month ago

Wedgie Humiliation

Wedgie Humiliation

ShemaleSin 1 year ago

AB104 Fuck-Fest plaything tester capitulate (Asian and English subtitles)

AB104 Fuck-Fest plaything tester capitulate (Asian and English subtitles)

TrannyGem 2 years ago

becomingfemme - natty is queen of the sissy university

becomingfemme - natty is queen of the sissy university

TransDoe 1 year ago

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

Amateur8 3 months ago

blond femboy bang machine sissy training!

blond femboy bang machine sissy training!

ShemaleSin 1 year ago

Sophia Loreen Party on Feb 12, 2026 - Part 2

4K 2:00 / 1:14:25

Sophia Loreen Party on Feb 12, 2026 - Part 2

Flirt4Free 2 weeks ago

”Hot Redhead T-girl Sexy Girl Gets Assfucking Training Rachael Belle”

”Hot Redhead T-girl Sexy Girl Gets Assfucking Training Rachael Belle”

4Wank 3 years ago

Atakan Ali Private Show

69% HD 2:00 / 6:07

Atakan Ali Private Show

Flirt4Free 1 year ago

Brutus K Strips and Shows Cock

Brutus K Strips and Shows Cock

Flirt4Free 9 years ago

Jessica Bloom turning Phil into Sissy slut Philippa stepmommy roleplay

HD 0:39 / 29:34

Jessica Bloom turning Phil into Sissy slut Philippa stepmommy roleplay

FapHouse 3 years ago

SIssy Victoria standing and having ass fucking climax

SIssy Victoria standing and having ass fucking climax

TrannyGem 7 months ago

23 year old fat sissy attempts first sissygasm

23 year old fat sissy attempts first sissygasm

xHamster 7 months ago

Domina wants to sundress you up like her plaything and help you instruct with a wire-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Domina wants to sundress you up like her plaything and help you instruct with a wire-on (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 10 months ago

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

FapHouse 1 year ago

Worship Superior Foreskin

57% HD 1:01 / 13:16

Worship Superior Foreskin

FapHouse 1 month ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 days ago

Sofia Rossi Intense Training With Dildo

Sofia Rossi Intense Training With Dildo

IcePorn 2 days ago

Nude Boytoy Sissy In Ideal White High High-Heeled Shoes Showcasing Her Diminutive Beefstick And Gigantic Bum

Nude Boytoy Sissy In Ideal White High High-Heeled Shoes Showcasing Her Diminutive Beefstick And Gigantic Bum

TrannyGem 9 months ago

SISSY EXTREME PEGGING!!! SLUT MAST FLOW!!! PRECUM COMPILATION

SISSY EXTREME PEGGING!!! SLUT MAST FLOW!!! PRECUM COMPILATION

aShemaleTube 6 months ago

His Boy, My Throne - Rimming and Obedience Training

His Boy, My Throne - Rimming and Obedience Training

FapHouse 4 months ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 4 months ago

Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification

Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification

Pornfact 2 weeks ago

Sissy crossdresser gets double stuffed part two

Sissy crossdresser gets double stuffed part two

SortPorn 4 years ago

Sissy Crossdresser POV Machine Fucking huge Anal orgasm

Sissy Crossdresser POV Machine Fucking huge Anal orgasm

xHamster 2 years ago

Sissy slut Xaviera trained by Master Pat

Sissy slut Xaviera trained by Master Pat

Tranny.one 4 years ago

OMG i have a cock in my mouth and i posted it on the internet

OMG i have a cock in my mouth and i posted it on the internet

xHamster 3 years ago

CHASTITY TRAINING // Transgirl Plugs her Butt and Cums during the time that Caged // Milky Lynn

CHASTITY TRAINING // Transgirl Plugs her Butt and Cums during the time that Caged // Milky Lynn

SortPorn 4 months ago

mistress roleplay i fuck u hard like my little sissy toy and cum deep inside you

mistress roleplay i fuck u hard like my little sissy toy and cum deep inside you

xHamster 2 years ago

Be my Rump to Throat Whore

Be my Rump to Throat Whore

TrannyGem 4 years ago

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

GayCK 4 years ago

Pole riding and extreme giant anal depth training dildo, practicing for whole arm fisting monster toy

Pole riding and extreme giant anal depth training dildo, practicing for whole arm fisting monster toy

xHamster 3 years ago

Gorgeous French Maid is ready to service

Gorgeous French Maid is ready to service

xHamster 3 years ago

Tgirl anal play

Tgirl anal play

xHamster 4 days ago

SometimesNiki maid tries a new toy

SometimesNiki maid tries a new toy

xHamster 2 years ago

Latex Sissy Girl Sucking Daddys Big Fat Cock

Latex Sissy Girl Sucking Daddys Big Fat Cock

xHamster 1 month ago

Slut Training With Adelaide Asterix JOI

Slut Training With Adelaide Asterix JOI

VipTube 1 month ago

Susan is frolicking with Cameron's donk

Susan is frolicking with Cameron's donk

Transvids.tv 1 year ago

Female domination on sissy whore in chastity cage

Female domination on sissy whore in chastity cage

xHamster 2 years ago

Sissy Slut Michelle Web Stream Educational Ass Stretching Show

Sissy Slut Michelle Web Stream Educational Ass Stretching Show

xHamster 1 year ago

Smashing dummy and goon to self hatred angel scarlett black

Smashing dummy and goon to self hatred angel scarlett black

TrannyGem 3 years ago

Flesh light fucking

HD 0:39 / 15:09

Flesh light fucking

FapHouse 5 years ago

Superslut walk, wedgie

Superslut walk, wedgie

TrannyGem 1 year ago

This was so humiliating @MistressMurmur gave me self facial training ????????

This was so humiliating @MistressMurmur gave me self facial training ????????

ShemaleSin 4 months ago

Tranny Latex Femdom and Sissy Training with Aspen Brooks and Natalie Mars and Roxxie Moth

Tranny Latex Femdom and Sissy Training with Aspen Brooks and Natalie Mars and Roxxie Moth

Sheshaft 4 months ago

Trans Sissy and Her straight Aussie BF playing with our ramrods and giving a kiss

Trans Sissy and Her straight Aussie BF playing with our ramrods and giving a kiss

ShemaleSin 3 years ago

The Dragonlady rides her Slaves face while he's locked in Chastity

The Dragonlady rides her Slaves face while he's locked in Chastity

Tranny.one 3 years ago

Anal Training Night

Anal Training Night

xHamster 8 months 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 4 years ago

Lily Demure Transformed and Ready for Cock by Tia Tizzianni

70% HD 0:08 / 0:15

Lily Demure Transformed and Ready for Cock by Tia Tizzianni

FapHouse 1 year ago

Sissy Maid in Bondage Sucking and Fucking Her Dildo

Sissy Maid in Bondage Sucking and Fucking Her Dildo

xHamster 4 months ago

Her Place Is Wherever He Wants Her to Be

63% 1:01 / 28:02

Her Place Is Wherever He Wants Her to Be

FapHouse 1 month ago

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