Training Videos - Trans (50,371)

2 huge hands free cumshots in a row

2 huge hands free cumshots in a row

XHamster 2 years ago

Ruined orgasm torture for my bondaged cd whore HD

Ruined orgasm torture for my bondaged cd whore HD

XHamster 5 years ago

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

XHamster 5 months ago

Chinese shelady In Public instruct

Chinese shelady In Public instruct

TrannyGem 6 years ago

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

XHamster 2 years ago

When your sissy is missing parent's rod

When your sissy is missing parent's rod

TrannyGem 2 years ago

becomingfemme - jennifer lunden cumming this way feels so good porn video

becomingfemme - jennifer lunden cumming this way feels so good porn video

TransDoe 1 year ago

Caged Sissy Cums with Inverted Chastity Still On

Caged Sissy Cums with Inverted Chastity Still On

XHamster 7 months ago

Sarah and Lucy Feminize You and Breezy You Out

Sarah and Lucy Feminize You and Breezy You Out

TrannyGem 3 years ago

sissypov - bunny summers working on it porn video

sissypov - bunny summers working on it porn video

TransDoe 1 year ago

U Wish Tgirl Jock Bi Confusion

U Wish Tgirl Jock Bi Confusion

FreePorn8 4 years ago

Horny Tgirl jerking her big stiff cock

Horny Tgirl jerking her big stiff cock

VikiPorn 1 year ago

Sophia Loreen Private Show

HD 2:00 / 14:34

Sophia Loreen Private Show

Camster 1 month ago

onlyfans - yasmine lee insert your girl cock now porn video

onlyfans - yasmine lee insert your girl cock now porn video

TransDoe 1 year ago

TS Yasmin Lee Rules Her Palace And Servant With Her Throbbing Hard Cock And Demands

TS Yasmin Lee Rules Her Palace And Servant With Her Throbbing Hard Cock And Demands

Eporner 6 months ago

Oriana Ross Private Show

Oriana Ross Private Show

Camster 2 years ago

Ftm Pegging

XHamster 6 months ago

Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.

Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.

XHamster 2 years ago

Shemale Natty Femboy Fucking

Shemale Natty Femboy Fucking

XHamster 12 years ago

Trixie Mills Private Show

HD 2:00 / 23:23

Trixie Mills Private Show

Camster 2 years ago

Lika Kai Private Show

56% 4K 2:00 / 5:34

Lika Kai Private Show

Camster 4 weeks ago

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

ShemaleSin 11 months ago

Bonnie Boombelle Private Show

4K 2:00 / 17:14

Bonnie Boombelle Private Show

Camster 1 month ago

Sissy very first anal masturbation video

Sissy very first anal masturbation video

XHamster 3 years ago

sissypov - ararity look how stiff i get when taking it up the ass porn video

sissypov - ararity look how stiff i get when taking it up the ass porn video

TransDoe 1 year ago

Emery Lune Anal Solo Play Vol Ii

Emery Lune Anal Solo Play Vol Ii

XHamster 2 months ago

Humiliation, strap-on and deep fisting

Humiliation, strap-on and deep fisting

XHamster 6 months ago

Indian Crossdresser Gaurisissy Feeling Horny in Purple Saree Looking and Fucking Like a Housewife

Indian Crossdresser Gaurisissy Feeling Horny in Purple Saree Looking and Fucking Like a Housewife

XHamster 1 year ago

My Big Ass Rides Huge BBC Toy

My Big Ass Rides Huge BBC Toy

XHamster 2 years ago

a Slow Tease You Won’t Forget.

a Slow Tease You Won’t Forget.

Camster 2 weeks ago

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

XHamster 3 months ago

AB144 Busty Cheongsam Beauty - Sweet Yuri Training 爆乳旗袍美女的秘密繩縛遊戲-甜蜜的百合調教

AB144 Busty Cheongsam Beauty - Sweet Yuri Training 爆乳旗袍美女的秘密繩縛遊戲-甜蜜的百合調教

AShemaleTube 7 months ago

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and

PornoXO 1 year ago

Winter Rae's Busty Sex Training

Winter Rae's Busty Sex Training

Some.Porn 1 year ago

”Sissy Dick Slut Training (Audio Erotica)”

”Sissy Dick Slut Training (Audio Erotica)”

IFuckedYourGF 1 year ago

Trixie Mills Private Show

Trixie Mills Private Show

Camster 2 years ago

Femboy vs Penetrate-machine

Femboy vs Penetrate-machine

4Gay 5 months ago

Trixie Mills Private Show

Trixie Mills Private Show

Camster 2 years ago

I Cumming on the Top!!!! Free Hands Sissygasm

I Cumming on the Top!!!! Free Hands Sissygasm

XHamster 1 month ago

Alisa Fresh Private Show

4K 2:00 / 14:43

Alisa Fresh Private Show

Camster 1 month ago

Lewd Stepdaughter Rides Massive 13 Inch Sex tool And Cums From Anal Screw Machine

Lewd Stepdaughter Rides Massive 13 Inch Sex tool And Cums From Anal Screw Machine

ShemaleSin 7 months ago

The bondage and feminization of a slave by a blonde queen

The bondage and feminization of a slave by a blonde queen

XHamster 2 years ago

horny skinny mistress JOI and CEI make u my sissy fuck hole

horny skinny mistress JOI and CEI make u my sissy fuck hole

XHamster 1 year ago

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

HentaiGem 4 years ago

Redhead Sissy's desires for anal encouragement Part 1

Redhead Sissy's desires for anal encouragement Part 1

XHamster 2 years ago

Pissing on my cute femboy GF Hayley

Pissing on my cute femboy GF Hayley

XHamster 10 months ago

BUBBLZexe dominates with his big cock & gives a steamy solo session

BUBBLZexe dominates with his big cock & gives a steamy solo session

GayVD 2 months ago

Special makeup for him

Special makeup for him

XHamster 1 week ago

Bunny-butler Reina Hanno Sucking Two Dildos

Bunny-butler Reina Hanno Sucking Two Dildos

XHamster 10 months ago

Sissy Doll's ass gets extreme insertion by a Monster can & more!

Sissy Doll's ass gets extreme insertion by a Monster can & more!

TrannyMovs 11 months ago

Little slut bottom getting trained to take girl dick. Part: 2

Little slut bottom getting trained to take girl dick. Part: 2

XHamster 5 months ago

my homework six

my homework six

TrannyGem 4 years ago

YOU Crave T-girl Dong Bi Confusion

YOU Crave T-girl Dong Bi Confusion

Dafreeporn 4 years ago

DIaper Pup Pissing , AbiYinger

DIaper Pup Pissing , AbiYinger

XHamster 3 years ago

Independent Training No67 Tampon Insertion, Wearing Bloomers, Tucking Chain Crossing

Independent Training No67 Tampon Insertion, Wearing Bloomers, Tucking Chain Crossing

XHamster 7 months ago

Sissy coming home from work

Sissy coming home from work

XHamster 1 year ago

Sissy Maid Ass to mouth and Self Facial

Sissy Maid Ass to mouth and Self Facial

XHamster 1 year ago

You failed the exam, teacher wants to punish you by feminizing and fucking your sissy hole(FEMINIZATION ROLEPLAY - AI GENERATED)

You failed the exam, teacher wants to punish you by feminizing and fucking your sissy hole(FEMINIZATION ROLEPLAY - AI GENERATED)

XHamster 1 year ago

Alisa Fresh Private Show

60% 4K 2:00 / 17:59

Alisa Fresh Private Show

Camster 1 month ago

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

XHamster 1 year ago

Light Training With a Sith Lad.

Light Training With a Sith Lad.

2BGay 3 years ago

Subby Gets Ass Punished by TS Sasha Blue

Subby Gets Ass Punished by TS Sasha Blue

XHamster 1 month ago

My ass eating ribbed dildo

My ass eating ribbed dildo

XHamster 1 month ago

Alexxa A Private Show

HD 2:00 / 21:22

Alexxa A Private Show

Camster 1 week ago

Sissy cockslut Is What you Will Always Be

Sissy cockslut Is What you Will Always Be

Transvids.tv 10 months ago

kawaii sissy teaching trap can't get enough of her fresh fucktoy

kawaii sissy teaching trap can't get enough of her fresh fucktoy

TrannyGem 4 years ago

Three big balls sunk in the ass

Three big balls sunk in the ass

XHamster 3 months ago

My little beta boy is a femmeboy

My little beta boy is a femmeboy

XHamster 1 year ago

Perseo & Dafne Private Show

HD 2:00 / 11:54

Perseo & Dafne Private Show

Camster 1 year ago

Training a football played to take beauty wang

Training a football played to take beauty wang

ShemaleSin 4 months ago

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY

XHamster 1 year ago

Kira Crash, Lena Jade - smashing The Sport Trainer

Kira Crash, Lena Jade - smashing The Sport Trainer

TransTube.tv 4 weeks ago

Stellar sissy Ponyboy Displaying his bare bod and high stilettos

Stellar sissy Ponyboy Displaying his bare bod and high stilettos

TrannyGem 4 years ago

Cum twice while riding huge corn

Cum twice while riding huge corn

XHamster 8 months ago

Rot Couch

XHamster 3 months ago

Obedient Tgirl Follows Orders

Obedient Tgirl Follows Orders

XHamster 3 months ago

Your Goddess Desires Ass Worship. A sure way to Earn your Place!

Your Goddess Desires Ass Worship. A sure way to Earn your Place!

TrannyGem 5 years ago

Anal Training By Felicia POV

Anal Training By Felicia POV

IcePorn 2 months ago

Sissy in Office

Sissy in Office

XHamster 8 months ago

Phat donk femboy bum fuck stick compilation

Phat donk femboy bum fuck stick compilation

TrannyGem 1 year ago

Hard-core Culo to Throat Sissy Hoe Pegging with Humungous Dark-hued Fake-rod by female dominance Goddess Domme Mercer

Hard-core Culo to Throat Sissy Hoe Pegging with Humungous Dark-hued Fake-rod by female dominance Goddess Domme Mercer

TransTube.tv 1 year ago

SFM VR 3D LATEX MISTRESS TESSA MILKS SLAVE THROUGH PROSTATE/SLAVE TRAINING

SFM VR 3D LATEX MISTRESS TESSA MILKS SLAVE THROUGH PROSTATE/SLAVE TRAINING

Eporner 6 years ago

Sissy bitch dressed up like a worthless slave and pegged by his dominating mistress

Sissy bitch dressed up like a worthless slave and pegged by his dominating mistress

XHamster 3 years ago

Alizzz Storm Private Show

Alizzz Storm Private Show

Camster 1 year ago

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

XHamster 4 years ago

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

XHamster 1 year ago

Cumslut Training Session 3A

Cumslut Training Session 3A

ShemaleSin 5 years ago

Ladyboy Natty Pink Femboy Pajamas

Ladyboy Natty Pink Femboy Pajamas

XHamster 12 years ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

Woman Encourages Guy Transformation Makeover into Woman

Woman Encourages Guy Transformation Makeover into Woman

XHamster 1 year ago

becomingfemme - aliza breeze black transgirl trained to be subservient

becomingfemme - aliza breeze black transgirl trained to be subservient

TransDoe 2 years ago

”TS Goddess Korra Del Rio training for pornlymics”

”TS Goddess Korra Del Rio training for pornlymics”

ThePornstar 1 year ago

Sissy Academy, Lesson#1 student Presentation

Sissy Academy, Lesson#1 student Presentation

XHamster 6 months ago

Abby Kitty - Ab094 Lustful Teacher Extreme Trained -milking 65cm Dildo (chinese And English Subtitles)

Abby Kitty - Ab094 Lustful Teacher Extreme Trained -milking 65cm Dildo (chinese And English Subtitles)

AbTranny 2 months ago

Pequeña Travesti jóven se vuelve toda una Sissy y se deja follar por Maduro

Pequeña Travesti jóven se vuelve toda una Sissy y se deja follar por Maduro

TrannyGem 1 year ago

Extreme Games in Hot Clothes!

Extreme Games in Hot Clothes!

XHamster 1 month ago

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Eporner 10 months ago

Yoga Freaks: Episode 14

Yoga Freaks: Episode 14

Some.Porn 7 months ago

Sophia Loreen Private Show

56% HD 2:00 / 6:16

Sophia Loreen Private Show

Camster 4 years ago

Horse Penis + Screw Machine +- Getting Screwed alongside BBC

Horse Penis + Screw Machine +- Getting Screwed alongside BBC

WebcamBros 1 year ago

becomingfemme - quinn tesla free use pet sissy maid

becomingfemme - quinn tesla free use pet sissy maid

TransDoe 2 years ago

Femdom POV: Humiliating My Cuck Ex Ep 3

Femdom POV: Humiliating My Cuck Ex Ep 3

XHamster 2 months 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!”

Rainblow 2 years ago

Happy New Year, Now Fuck Me Harder!

Happy New Year, Now Fuck Me Harder!

XHamster 2 months ago

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

ShemaleSin 2 years ago

Sophia Loreen Private Show

4K 2:00 / 10:29

Sophia Loreen Private Show

Camster 8 months ago

Domina gonna convert you in a sissy toy and make your backside aching (FEMINIZATION ROLEPLAY - AI GENERATED)

Domina gonna convert you in a sissy toy and make your backside aching (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 1 year ago

Sophia Loreen Party on Jun 19, 2026 - Part 3

71% HD 2:00 / 47:03

Sophia Loreen Party on Jun 19, 2026 - Part 3

Camster 1 month ago

TANGENTOD - Discipline & Rewards Under Goddess Tangent

TANGENTOD - Discipline & Rewards Under Goddess Tangent

Fapnado 3 days ago

Asymmetric Bars, Wild Fuck

Asymmetric Bars, Wild Fuck

Some.Porn 5 days ago

Sophia Loreen Private Show

68% 4K 2:00 / 10:47

Sophia Loreen Private Show

Camster 4 weeks ago

Sophia Loreen Private Show

61% 4K 2:00 / 9:48

Sophia Loreen Private Show

Camster 1 week ago

Man Transformed Into Woman to Go Clubbing

Man Transformed Into Woman to Go Clubbing

XHamster 3 weeks ago

trans bitch with a meaty dick

trans bitch with a meaty dick

XHamster 5 months ago

Flip Fuck with TS Kendall Penny

Flip Fuck with TS Kendall Penny

XHamster 3 weeks ago

Sophia Loreen Private Show

52% HD 2:00 / 4:47

Sophia Loreen Private Show

Camster 4 weeks ago

Mistress Turns Her Fart-Sniffing Sissy Slave Gay: Fart Fetish, Ass Worship, Bisexual, Anal, Blowjob, Cum Eating, Foot Fetish

Mistress Turns Her Fart-Sniffing Sissy Slave Gay: Fart Fetish, Ass Worship, Bisexual, Anal, Blowjob, Cum Eating, Foot Fetish

XHamster 5 days ago

Extreme BBC Anal Dildo Ballsdeep in This Sissy's Ass with a Fucking Machine - Trailler

Extreme BBC Anal Dildo Ballsdeep in This Sissy's Ass with a Fucking Machine - Trailler

XHamster 2 months ago

Sissy Street Walk, Hiking Trail in Panties, Slutty Workout Shorts in Public

Sissy Street Walk, Hiking Trail in Panties, Slutty Workout Shorts in Public

XHamster 4 days ago

Femdom's Cock-hungry Sissy Fetish Exposed

Femdom's Cock-hungry Sissy Fetish Exposed

Jizzberry 4 years ago

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