Training Videos - Trans (119,489)

BONDAGE & DISCIPLINE sissy with strapped soles showcases her GAPE and spunk on couch from massager

BONDAGE & DISCIPLINE sissy with strapped soles showcases her GAPE and spunk on couch from massager

TrannyGem 3 years ago

YOU’RE GAY & THAT’S OK

55% 4K 0:25 / 7:56

YOU’RE GAY & THAT’S OK

Clips4sale 3 years ago

Sui Mizumori Riku Mukai,A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Sui Mizumori Riku Mukai,A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Tranny.one 1 year ago

Turning Him Into A Sissy Slut

Turning Him Into A Sissy Slut

Tranny.one 2 years ago

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

KAMS 1 year ago

Two Asses for Your Cock

59% 4K 2:00 / 5:05

Two Asses for Your Cock

Flirt4Free 1 year ago

23 year old fat sissy attempts first sissygasm

23 year old fat sissy attempts first sissygasm

XHamster 1 year ago

Sissy Compiliation

Sissy Compiliation

XHamster 11 months ago

Full Crossdressing Transformation

Full Crossdressing Transformation

XHamster 4 years ago

Preying on your weakness for nylons

66% HD 0:10 / 15:17

Preying on your weakness for nylons

LoyalFans 1 year ago

XXL Kong toy training part 1 anal insertion

XXL Kong toy training part 1 anal insertion

XHamster 4 days ago

”A Priceless Memento - Seth Gamble, Gal Ritchie”

”A Priceless Memento - Seth Gamble, Gal Ritchie”

TransHero 7 months ago

Cindy slut in red gagged and fucked

Cindy slut in red gagged and fucked

XHamster 4 months ago

Foot Fucking, Fisting, Double Fisting Shoulder Deep, Prolapse and Gaped - Jasmine_dlight & Adelina Noir

HD 0:39 / 13:19

Foot Fucking, Fisting, Double Fisting Shoulder Deep, Prolapse and Gaped - Jasmine_dlight & Adelina Noir

FapHouse 10 months ago

Cbt with Black Stockings, a Bitsph

56% HD 2:00 / 6:30

Cbt with Black Stockings, a Bitsph

Camster 4 years ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

XHamster 4 months ago

Sissy for Whitney_wmv__

43% 0:23 / 8:23

Sissy for Whitney_wmv__

Clips4sale 1 year ago

Artesca Private Show

52% HD 2:00 / 4:15

Artesca Private Show

Flirt4Free 5 months ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Camster 1 year ago

Long Machine Fuck for Bi Slut with Huge Fake Tits

HD 1:01 / 19:05

Long Machine Fuck for Bi Slut with Huge Fake Tits

FapHouse 2 years 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

Sex-er-cise

XHamster 1 year ago

Asmr: Sissy, Accept Yourself! You Are Loved. Psychology. Gloves. Arya Grander

Asmr: Sissy, Accept Yourself! You Are Loved. Psychology. Gloves. Arya Grander

XHamster 1 year ago

Sophia Loreen Party on Aug 11, 2026 - Part 3

4K 2:00 / 26:43

Sophia Loreen Party on Aug 11, 2026 - Part 3

Camster 1 day ago

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! A Perverted Circle Of Trans Lovers.

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! A Perverted Circle Of Trans Lovers.

XHamster 9 months ago

CEI Sissy Training - Hentai Tranced JOI

CEI Sissy Training - Hentai Tranced JOI

HentaiGem 1 year ago

Sophia Loreen Private Show

66% HD 2:00 / 35:48

Sophia Loreen Private Show

Camster 1 month ago

Femdom Ts Pool Party Fuck Fest wmv

51% HD 0:11 / 26:16

Femdom Ts Pool Party Fuck Fest wmv

Clips4sale 4 years ago

Hot sissy XDemon Dildo ride solo

Hot sissy XDemon Dildo ride solo

XHamster 1 week ago

Foursome Group Sex Fuckfest

45% HD 0:39 / 40:56

Foursome Group Sex Fuckfest

FapHouse 5 months ago

Hole Training

Eporner 1 year ago

Sissy Throat Fuck Cum Swallow Training

Sissy Throat Fuck Cum Swallow Training

Tranny.one 4 years ago

Extreme Anal Gape: Fat Ass Cute Goth Trans Girl in Raven Cosplay Inserting the Testicles of a Dildo Into Her Anus

Extreme Anal Gape: Fat Ass Cute Goth Trans Girl in Raven Cosplay Inserting the Testicles of a Dildo Into Her Anus

XHamster 6 days ago

Casting of Anal Slave Nikita

56% HD 0:39 / 12:53

Casting of Anal Slave Nikita

FapHouse 8 months ago

Sissy Crossdresser POV Machine Fucking huge Anal orgasm

Sissy Crossdresser POV Machine Fucking huge Anal orgasm

XHamster 2 years ago

I Caught Stepdaddy Jerking Off in His Room – Oops!

I Caught Stepdaddy Jerking Off in His Room – Oops!

XXXShake 2 years ago

Black latex sissy slave doll gets stuck in selfbondage

Black latex sissy slave doll gets stuck in selfbondage

XHamster 2 years ago

Multiformity Itsol HFO training mindfuck

Multiformity Itsol HFO training mindfuck

PornFreeNow 8 months ago

good girls always get a reward

58% 1:01 / 26:35

good girls always get a reward

FapHouse 3 years ago

Female Dom Gf Won’t let me take out speculum till she’s creampied trans jism bi-racial big black cock femboy

Female Dom Gf Won’t let me take out speculum till she’s creampied trans jism bi-racial big black cock femboy

TrannyGem 3 years ago

I'm a woman, who wants to open me up

I'm a woman, who wants to open me up

XHamster 6 months ago

Double Stuffed Bimbo

Double Stuffed Bimbo

XHamster 1 year ago

Lika Kai Private Show

Lika Kai Private Show

Camster 3 weeks ago

”Variety Itsol HFO training mindfuck”

”Variety Itsol HFO training mindfuck”

TransHero 4 months ago

Marian & Richard Private Show

63% HD 2:00 / 5:27

Marian & Richard Private Show

Flirt4Free 2 months ago

big sissy training compilation!

HD 0:30 / 52:36

big sissy training compilation!

AnalVids 1 year ago

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 3

69% HD 2:00 / 9:54

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 3

Flirt4Free 3 months ago

Petra's 8th training (incl 1st fist,massive sex toy and greater quantity)

Petra's 8th training (incl 1st fist,massive sex toy and greater quantity)

Amateur8 1 year ago

Femboy Anal Training

Femboy Anal Training

FapHouse 2 months ago

TS Jasmine Lotus Spit Roasted and trained to be a proper Anal Slut by Alexxa Von Hell & Slayer

68% 0:11 / 22:42

TS Jasmine Lotus Spit Roasted and trained to be a proper Anal Slut by Alexxa Von Hell & Slayer

Clips4sale 2 years ago

Arabic Mistress Turkish Sissy Slut with Big Cock

61% 1:01 / 5:18

Arabic Mistress Turkish Sissy Slut with Big Cock

FapHouse 2 years ago

Double Anal Tranny Ass Fucked with Vibrator and Fat Dick Inserted

Double Anal Tranny Ass Fucked with Vibrator and Fat Dick Inserted

XHamster 4 months ago

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

62% HD 0:26 / 14:00

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

Clips4sale 8 months ago

Sasha Osborn Private Show

HD 2:00 / 17:51

Sasha Osborn Private Show

Camster 4 years ago

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

TrannyGem 5 years ago

Hannah and the dirty toilets

Hannah and the dirty toilets

XHamster 9 months ago

Sophia Loreen Private Show - Part 2

63% HD 2:00 / 10:36

Sophia Loreen Private Show - Part 2

Camster 3 months ago

You lose! Dominated by the gamer girl

56% HD 1:01 / 30:38

You lose! Dominated by the gamer girl

FapHouse 4 years ago

AB090 高速榨精捆绑女高校生(中英字幕) 女王调教射精丝袜网袜高跟自慰杯跳蛋

AB090 高速榨精捆绑女高校生(中英字幕) 女王调教射精丝袜网袜高跟自慰杯跳蛋

TrannyGem 1 year ago

Enormous black trouser snake plumbing sissy hoe Lola Crystals

Enormous black trouser snake plumbing sissy hoe Lola Crystals

TrannyGem 3 years ago

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

XHamster 3 weeks ago

Sissykanisa Get Fucked by Reina in Swimming Suit

48% 0:39 / 13:36

Sissykanisa Get Fucked by Reina in Swimming Suit

FapHouse 1 year ago

Femboy Close up Pussy Training with Dildo with Farting and Gaping

HD 1:01 / 31:00

Femboy Close up Pussy Training with Dildo with Farting and Gaping

FapHouse 1 year ago

Domme Feminizes Then Fucks Sissy

Domme Feminizes Then Fucks Sissy

XHamster 3 weeks ago

Ava Venom Fucks TS Kaela Luna’s Slutty Holes Until I Cum

56% 0:29 / 15:23

Ava Venom Fucks TS Kaela Luna’s Slutty Holes Until I Cum

Clips4sale 1 year ago

What If I Had A Penis

46% HD 0:10 / 12:01

What If I Had A Penis

LoyalFans 2 months ago

Compilation of Tgirls Training their Dudes with Bareback Tranny Fucks, Lingerie, and Big Asses in Compilation

Compilation of Tgirls Training their Dudes with Bareback Tranny Fucks, Lingerie, and Big Asses in Compilation

TrannyMovs 1 week ago

Threesome with Salome Salvi and Tantaly Sex Doll

Threesome with Salome Salvi and Tantaly Sex Doll

XHamster 2 months ago

OLIVE GREEN RAW SHEMALE FUCKING ANAL HOOK OLIVE GREEN LATEX CATSUIT

84% HD 0:22 / 10:09

OLIVE GREEN RAW SHEMALE FUCKING ANAL HOOK OLIVE GREEN LATEX CATSUIT

Clips4sale 2 years ago

Super Ultimate Compilation

Super Ultimate Compilation

XHamster 11 months ago

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

Camster 4 weeks ago

Tranny football slut! After training, it's time for a blowjob!

Tranny football slut! After training, it's time for a blowjob!

XHamster 1 month ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Camster 2 weeks ago

Chinese Crossdresser CD ass Training by Mistress Chines

Chinese Crossdresser CD ass Training by Mistress Chines

Sheshaft 2 years ago

Abby Kitty In Ab140 Mimi Baos Introduction To Bdsm Training -blowjob,sex (chinese And English Subtitles)

Abby Kitty In Ab140 Mimi Baos Introduction To Bdsm Training -blowjob,sex (chinese And English Subtitles)

AbTranny 2 months 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

EpicGFs 1 year ago

fuck! i m gonna cum from this!!!!

HD 0:30 / 57:13

fuck! i m gonna cum from this!!!!

AnalVids 2 weeks ago

Vibrating My Tiny Little Dick and Fucking My Sissy Ass

Vibrating My Tiny Little Dick and Fucking My Sissy Ass

FapHouse 4 days ago

Sophia Loreen Private Show

4K 2:00 / 12:00

Sophia Loreen Private Show

Camster 1 day ago

How To Self Suck Yoga Training With Jessica Bloom SFW

How To Self Suck Yoga Training With Jessica Bloom SFW

Pornwhite 5 months ago

The Ultimate Chastity Cage Review and Guide Video

45% HD 0:39 / 37:26

The Ultimate Chastity Cage Review and Guide Video

FapHouse 2 years ago

Trans Domina Instructing her Fresh Encaged Sissy and her Cock-Squeezing Fuck-Holes

Trans Domina Instructing her Fresh Encaged Sissy and her Cock-Squeezing Fuck-Holes

TrannyGem 3 years ago

Quick Anal Session

Quick Anal Session

XHamster 2 months ago

Anal dessert

XHamster 4 years ago

Prostate Milking

64% HD 0:23 / 11:09

Prostate Milking

Clips4sale 1 year ago

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

XHamster 1 year ago

Sissy attempting to get caught

Sissy attempting to get caught

TrannyGem 1 year ago

Sissy Jessica's Weekly Hole Training 1 (4k)

4K 0:39 / 22:53

Sissy Jessica's Weekly Hole Training 1 (4k)

FapHouse 1 week ago

Cummy Classroom Sissy Slut Tgirl Panty Loads

58% 0:11 / 14:08

Cummy Classroom Sissy Slut Tgirl Panty Loads

Clips4sale 3 years ago

Emery Lune Anal Solo Play Vol Ii

Emery Lune Anal Solo Play Vol Ii

XHamster 2 months ago

Sissy Juvia does some encouraging Sissyfication Training JOI

Sissy Juvia does some encouraging Sissyfication Training JOI

XHamster 3 years ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

XHamster 2 years ago

Her panties on you makes her cuck you raw femdom humiliation

Her panties on you makes her cuck you raw femdom humiliation

AveXXX 1 week ago

Black Boy Got Turn on by His Coach at the Training Section

Black Boy Got Turn on by His Coach at the Training Section

XHamster 5 months ago

Trans Slut Will Receive Anal Training From a Dominant Woman

65% HD 0:39 / 30:05

Trans Slut Will Receive Anal Training From a Dominant Woman

FapHouse 8 months ago

Relent to Your Trans Mistress

Relent to Your Trans Mistress

XHamster 4 months ago

Sissy Hope streaming online and showing how she trains her pussy boy for anal fun

Sissy Hope streaming online and showing how she trains her pussy boy for anal fun

XHamster 4 years ago

Sissy Silly Step-Sister Raunchy Drill and Gargle

Sissy Silly Step-Sister Raunchy Drill and Gargle

TrannyGem 5 years ago

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

XHamster 10 months ago

you Have to Suck Cock to Worship My Legs - Holland Of Chicago And Domina Andrea Rosu 1080

HD 0:10 / 12:41

you Have to Suck Cock to Worship My Legs - Holland Of Chicago And Domina Andrea Rosu 1080

LoyalFans 2 months ago

Dandy's New Doll - BBW mistress Princess Dandy pegs crossdresser Bailey Wilde on dungeon sex swing

Dandy's New Doll - BBW mistress Princess Dandy pegs crossdresser Bailey Wilde on dungeon sex swing

Clips4sale 2 years ago

Having a Hard Time - Shemale Jane & Seiko Sex in Ladies Toilet - Part 2

63% HD 0:39 / 18:15

Having a Hard Time - Shemale Jane & Seiko Sex in Ladies Toilet - Part 2

FapHouse 2 weeks ago

Kendall Penny Sissy Training Wih Cumshot Reward

Kendall Penny Sissy Training Wih Cumshot Reward

IcePorn 5 months ago

Insatiable Bisex Shelady Filthyty Fuck-A-Thon

Insatiable Bisex Shelady Filthyty Fuck-A-Thon

TransTube.tv 1 week ago

Sissy Maid in Bondage Sucking and Fucking Her Dildo

Sissy Maid in Bondage Sucking and Fucking Her Dildo

XHamster 8 months ago

Sissy Bunny Training

65% HD 1:01 / 13:05

Sissy Bunny Training

FapHouse 1 year ago

Ema Devine Private Show

55% 4K 2:00 / 5:03

Ema Devine Private Show

Camster 1 year ago

A Trans Captured in a Dominatrix's Dungeon Gets Her Body Slammed

HD 1:01 / 13:12

A Trans Captured in a Dominatrix's Dungeon Gets Her Body Slammed

FapHouse 3 months ago

Charlie Cano Private Show

Charlie Cano Private Show

Flirt4Free 3 years ago

JOI Dirty Talk in French Femdom Training Beautiful Ass Close-up Sissy Obeys!

JOI Dirty Talk in French Femdom Training Beautiful Ass Close-up Sissy Obeys!

FapHouse 8 months ago

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

AShemaleTube 3 months ago

WITCH RAVEN TURNS YOU INTO A BEAUTIFUL WOMAN

HD 0:10 / 12:51

WITCH RAVEN TURNS YOU INTO A BEAUTIFUL WOMAN

LoyalFans 3 years ago

Jessica Bloom Cumshot Compilation 2024

63% HD 1:01 / 19:36

Jessica Bloom Cumshot Compilation 2024

FapHouse 1 year ago

You Owe the Boss - Pay With Your Mouth

HD 0:25 / 12:56

You Owe the Boss - Pay With Your Mouth

Clips4sale 6 days ago

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

XHamster 2 months ago

LATEX BONDAGE SHEMALE DEEPTHROAT SUB CROSSDRESSER IN RED HAIR P1

85% HD 0:22 / 10:19

LATEX BONDAGE SHEMALE DEEPTHROAT SUB CROSSDRESSER IN RED HAIR P1

Clips4sale 2 years ago

Sissy Kate learns how to use the anal screwing machine with Lisa

Sissy Kate learns how to use the anal screwing machine with Lisa

ShemaleSin 1 year ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Lesbian8 1 year ago

Ruined By SheMales

44% HD 0:15 / 7:58

Ruined By SheMales

Clips4sale 2 years ago

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