Training Videos - Trans (124,124)

Adorable Yam-Sized Culo Trans Doll Assfuck Gaped Open

Adorable Yam-Sized Culo Trans Doll Assfuck Gaped Open

TrannyGem 4 years ago

Slut Training With Queenie Steph POV

Slut Training With Queenie Steph POV

IcePorn 8 months ago

Mesmeriza Compilation 11 Island of Desires

Mesmeriza Compilation 11 Island of Desires

XHamster 1 year ago

Raine Ryder bareback fucked by Flare Wolfsbane FULL VID

Raine Ryder bareback fucked by Flare Wolfsbane FULL VID

XHamster 8 months ago

Sissy Faggot Life (Deepthroat Training)

Sissy Faggot Life (Deepthroat Training)

Tranny.one 4 years ago

Cum Training for Faggots

Cum Training for Faggots

TrannyGem 7 years ago

Latina Sissy Crossdresser Sexed By Dark Daddy

Latina Sissy Crossdresser Sexed By Dark Daddy

DeegX 3 years ago

Crhistian & Dereckk & Friends Private Show - Part 2

HD 2:00 / 13:01

Crhistian & Dereckk & Friends Private Show - Part 2

Flirt4Free 7 years ago

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

TrannyGem 3 years ago

Slut makeover and anal training

49% HD 0:24 / 9:27

Slut makeover and anal training

Clips4sale 1 year ago

I Love Sissygasm, While I Fuck My Sissy Ass

I Love Sissygasm, While I Fuck My Sissy Ass

XHamster 3 weeks ago

Sissy Slave Fed Spit And Cum

Sissy Slave Fed Spit And Cum

XHamster 1 year ago

Gorgeous Femboy Sissy Anal Invasion Comp

Gorgeous Femboy Sissy Anal Invasion Comp

TrannyGem 5 years ago

Sissy trainer: become slut like her

Sissy trainer: become slut like her

XHamster 4 years ago

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

61% HD 0:39 / 9:38

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

FapHouse 1 year ago

Dizzys dildo oral training in the mirror

Dizzys dildo oral training in the mirror

AShemaleTube 2 years ago

EXTREME COMPELLING CROSSDRESSING MENTAL CONDITIONING - Female Domination Demands You Crossdress

EXTREME COMPELLING CROSSDRESSING MENTAL CONDITIONING - Female Domination Demands You Crossdress

Clips4sale 1 year ago

4K - Bound by Black Magic Slime - Corrupted Elf Femboy gf Cummed Twice and Drained - Strawberry Wonderland EP 5 (Mini Version)

4K - Bound by Black Magic Slime - Corrupted Elf Femboy gf Cummed Twice and Drained - Strawberry Wonderland EP 5 (Mini Version)

Clips4sale 1 week ago

Satin Lingerie & Estim Ruined Orgasm (4k)

4K 0:30 / 12:09

Satin Lingerie & Estim Ruined Orgasm (4k)

Clips4sale 1 year ago

Sissy Gets Caught

64% 0:30 / 9:26

Sissy Gets Caught

Clips4sale 1 year ago

hot trans in fishnets takes multiple BBC creampies and cums

58% HD 0:14 / 8:07

hot trans in fishnets takes multiple BBC creampies and cums

Clips4sale 1 year ago

Amateur sissy stretches and pounds her cummy drenched aperture until this babe sissygasms

Amateur sissy stretches and pounds her cummy drenched aperture until this babe sissygasms

BigTitsLust 2 weeks ago

Gutless sissy clitty dildoing her bootie on the open door while vans pass by

Gutless sissy clitty dildoing her bootie on the open door while vans pass by

TrannyGem 3 years ago

Tv Isabella's Compilation Y-Training Scheme

Tv Isabella's Compilation Y-Training Scheme

AShemaleTube 11 months ago

I Turn My Slave Into a Sissy Slut and Make Him Suck a Dildo, Mf

54% HD 1:01 / 11:06

I Turn My Slave Into a Sissy Slut and Make Him Suck a Dildo, Mf

FapHouse 1 month ago

Monster Mega butt plug. larissa1sexdoll sexy trans. Extreme insertions. Unique ass piercings.

Monster Mega butt plug. larissa1sexdoll sexy trans. Extreme insertions. Unique ass piercings.

XHamster 2 years ago

SWALLOW SHEMALE CUM FOR GODDESS FAITH - PART 2

56% 0:30 / 7:05

SWALLOW SHEMALE CUM FOR GODDESS FAITH - PART 2

Clips4sale 10 months ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 3 years ago

Sissy cums in chastity and licks it all up

Sissy cums in chastity and licks it all up

XHamster 1 year ago

Undercover Crossdresser Bi-raunchy Sissy Humiliation Exposure Encouragement Mesmerizing Erotic Audio

Undercover Crossdresser Bi-raunchy Sissy Humiliation Exposure Encouragement Mesmerizing Erotic Audio

PornFreeNow 1 month ago

Petra,s 10th training

Petra,s 10th training

AShemaleTube 1 year 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 5 months ago

Girl Love Fuck Crossdresser

Girl Love Fuck Crossdresser

XHamster 1 month ago

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

60% HD 0:29 / 23:10

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

Clips4sale 8 months ago

All that mouth training pays off : facefucking charming transwife Melody

All that mouth training pays off : facefucking charming transwife Melody

Amateur8 1 year ago

transgender princess Makes You Learn To Love BIG BLACK COCK

transgender princess Makes You Learn To Love BIG BLACK COCK

TrannyGem 2 years ago

Marian & Richard Private Show

61% HD 2:00 / 9:13

Marian & Richard Private Show

Camster 6 days ago

Charlie Cano Private Show

62% HD 2:00 / 5:11

Charlie Cano Private Show

Flirt4Free 3 years ago

Scene 1 - Sissy Dreamland - Punk rock dominates & makes feminized femboy suck BBC strapon dildo

Scene 1 - Sissy Dreamland - Punk rock dominates & makes feminized femboy suck BBC strapon dildo

XHamster 2 years ago

transfixed - jade venus transgirl fuck her workplace safety officer roman todd

transfixed - jade venus transgirl fuck her workplace safety officer roman todd

TransDoe 2 years ago

Sophie Fantasy Private Show

62% HD 2:00 / 8:14

Sophie Fantasy Private Show

Flirt4Free 2 weeks ago

Milk Your Transgirl EPISODE

Milk Your Transgirl EPISODE

ShemaleSin 4 years ago

Trans gets Cuffed and Stuffed by Large Dick

Trans gets Cuffed and Stuffed by Large Dick

Amateur8 4 years ago

I'll Turn You Into My Sissy Slut!

I'll Turn You Into My Sissy Slut!

XHamster 9 months ago

Pathetic Sissy Slut Vlada Is Humiliated And Stretched - Bottle Comes In Completely

Pathetic Sissy Slut Vlada Is Humiliated And Stretched - Bottle Comes In Completely

XHamster 2 months ago

CROSSDRESSING CUMSLUT

CROSSDRESSING CUMSLUT

TrannyGem 3 years ago

1 Hour Special: Huge Ass Femboy Samus Wedgie, Spanks, Creampie and Anal Fucking with Multiple Dildos

1 Hour Special: Huge Ass Femboy Samus Wedgie, Spanks, Creampie and Anal Fucking with Multiple Dildos

XHamster 6 months ago

The new gardener is being trained 4K

57% 4K 0:11 / 22:53

The new gardener is being trained 4K

Clips4sale 3 years ago

Three Different Videos and One Happy Ending

Three Different Videos and One Happy Ending

XHamster 2 weeks ago

TS Slut milking

72% 0:30 / 14:31

TS Slut milking

Clips4sale 1 year ago

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

TrannyGem 3 years ago

Sissy training: how to cum in chastity? Ride ever bigger dildos to sissygasm

Sissy training: how to cum in chastity? Ride ever bigger dildos to sissygasm

Itsrealamateurs 3 months ago

FemdomRAW: The Hottest Dominant Bitches

FemdomRAW: The Hottest Dominant Bitches

Eporner 1 year ago

Feelipe & Adara Private Show

66% HD 2:00 / 7:06

Feelipe & Adara Private Show

Flirt4Free 1 year ago

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

ShemaleSin 4 years ago

Sissy #two: Becoming A Dick Whore

Sissy #two: Becoming A Dick Whore

SortPorn 1 year ago

SometimesNiki sissy maid anal training

SometimesNiki sissy maid anal training

XHamster 2 years ago

My anal training

My anal training

ShemaleSin 1 week ago

sloppy queer pig servenaked manacled and corded up at his nuts with fake penis in bum

sloppy queer pig servenaked manacled and corded up at his nuts with fake penis in bum

4Gay 2 weeks ago

Daimond Cooper Private Show

4K 2:00 / 10:56

Daimond Cooper Private Show

Flirt4Free 3 months ago

Feelipe & Adara Private Show

58% HD 2:00 / 4:26

Feelipe & Adara Private Show

Camster 1 year ago

Sasha Earth femboy cum hands free on a sex machine homemade amateur

Sasha Earth femboy cum hands free on a sex machine homemade amateur

XHamster 3 months ago

AB138 Bitch Sissy Cumshot and Edging training (Chinese and English subtitles)

AB138 Bitch Sissy Cumshot and Edging training (Chinese and English subtitles)

XHamster 1 year ago

Joi My mistress spits on me, trains me like a

Joi My mistress spits on me, trains me like a

XHamster 2 months ago

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

SortPorn 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

$Let\'s start a little game My hard cock in your face and and my balls in your mouth!(jerk)(yummy)(rasp)(squirt)$ HD 2:00 / 5:34

Let\'s start a little game My hard cock in your face and and my balls in your mouth!(jerk)(yummy)(rasp)(squirt)

Flirt4Free 5 years ago

Jeanne Coxxx teaches and guzzles her way to a hot sissy ass

Jeanne Coxxx teaches and guzzles her way to a hot sissy ass

TrannyMovs 4 days ago

Ria Bentley gets her tight ass drilled and cum covered in this wild TS video

Ria Bentley gets her tight ass drilled and cum covered in this wild TS video

TrannyMovs 4 months ago

Hanna Ven Private Show

64% HD 2:00 / 10:55

Hanna Ven Private Show

Flirt4Free 2 years ago

Sissy Boyfriend Found Out and Pegged

Sissy Boyfriend Found Out and Pegged

Clips4sale 3 years ago

Sissygasm cum sissy balls in chastity with vibrator

Sissygasm cum sissy balls in chastity with vibrator

XHamster 1 year ago

Wanking Gutless Female Pink Cigar To BIG BLACK COCK PMV

Wanking Gutless Female Pink Cigar To BIG BLACK COCK PMV

TrannyGem 1 year ago

Latino Anal in Knee High Socks

57% HD 2:00 / 4:28

Latino Anal in Knee High Socks

Flirt4Free 9 years ago

White Femboy Ejaculates HandsFree In Cell Love Glove - 60 Sec Destroyed Climax

White Femboy Ejaculates HandsFree In Cell Love Glove - 60 Sec Destroyed Climax

TrannyGem 1 year ago

Sophia Loreen Private Show

49% HD 2:00 / 8:40

Sophia Loreen Private Show

Camster 3 months ago

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

XHamster 9 months ago

brazilian trans slave training & anal fisting

brazilian trans slave training & anal fisting

AnalVids 8 months ago

Daimond Cooper Private Show

Daimond Cooper Private Show

Flirt4Free 3 months ago

UwU disabled transgender zoe jarvis solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

UwU disabled transgender zoe jarvis solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

XHamster 1 month ago

Mike Swift & David Golden Private Show

54% HD 2:00 / 11:49

Mike Swift & David Golden Private Show

Flirt4Free 1 month ago

Pushing SISSY's PROSTATE until he leaks for me!

Pushing SISSY's PROSTATE until he leaks for me!

XHamster 1 year ago

Turned Out Sissy Interactive Toy Experience

Turned Out Sissy Interactive Toy Experience

XHamster 2 years ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

64% HD 1:01 / 11:01

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

FapHouse 1 year ago

Femboy crossdresser leaks jizz two times on stomach full salute while ass-fuck fapping with long fuck stick

Femboy crossdresser leaks jizz two times on stomach full salute while ass-fuck fapping with long fuck stick

TrannyGem 1 year ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 1

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 1

XHamster 7 months ago

Petra,s 5th training incl creampie dp and big dildo

Petra,s 5th training incl creampie dp and big dildo

XHamster 1 year ago

Its NOT GAY if its SHEMALES

44% HD 0:15 / 32:34

Its NOT GAY if its SHEMALES

Clips4sale 1 year ago

Sissy gives str8 military chap a lapdance then sucks his dong

Sissy gives str8 military chap a lapdance then sucks his dong

ShemaleSin 5 years ago

Pinky X Receives Anal Training (free)

Pinky X Receives Anal Training (free)

ShemaleSex 2 weeks ago

POV Hard Pegging Jasmine Dlight From Mistress

POV Hard Pegging Jasmine Dlight From Mistress

XHamster 10 months ago

Duan Anal Training Topping Bareback

Duan Anal Training Topping Bareback

AbTranny 1 year ago

Fuck Machine Session

Fuck Machine Session

XHamster 2 weeks ago

Bigger Than Your Boyfriend, Babe. Say It: You Want It

65% HD 0:25 / 10:34

Bigger Than Your Boyfriend, Babe. Say It: You Want It

Clips4sale 1 month ago

Fresh knuckle fisting, deep anal dildo riding, and massive dildo fisting for a bisexual dude

Fresh knuckle fisting, deep anal dildo riding, and massive dildo fisting for a bisexual dude

GayVD 3 months ago

cherry and i dominate our disobedient puppies nyxi and livi

cherry and i dominate our disobedient puppies nyxi and livi

PornBox 2 years ago

Sedy Ladyboy does a Thousand Ball Plappies while gooning for the BNWO

Sedy Ladyboy does a Thousand Ball Plappies while gooning for the BNWO

XHamster 2 months ago

Master & Ithan & Aleex Private Show

57% HD 2:00 / 31:36

Master & Ithan & Aleex Private Show

Flirt4Free 1 year 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

Ruined By SheMales

44% HD 0:15 / 7:58

Ruined By SheMales

Clips4sale 2 years ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-girl

XHamster 2 years ago

Bimbo Training with Maya Sinstress: Slut Maxxxing

Bimbo Training with Maya Sinstress: Slut Maxxxing

Clips 3 weeks ago

Trans couple analfucking

Trans couple analfucking

Some.Porn 1 year ago

Lisan & Mine Private Show

66% 4K 2:00 / 23:47

Lisan & Mine Private Show

Camster 3 weeks ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

XHamster 4 months ago

Leather corset sissy fucked

Leather corset sissy fucked

Clips4sale 7 months ago

Sissy Bi Training POV: Me or Cock?

54% HD 0:39 / 16:31

Sissy Bi Training POV: Me or Cock?

FapHouse 4 months ago

Recruited by Transsexual Headmistress - (Sissy caption Story)

Recruited by Transsexual Headmistress - (Sissy caption Story)

ShemaleSin 5 years ago

Sissy Secretary Seduces BBC Boss Into Blacked Rencounter

Sissy Secretary Seduces BBC Boss Into Blacked Rencounter

ShemaleSin 5 months ago

Training makes perfect

Training makes perfect

XHamster 1 year ago

Sophia Loreen Private Show

67% 4K 2:00 / 9:48

Sophia Loreen Private Show

Camster 1 month ago

TANGENTOD - Stretching and Filling Fuckpet Holes With Thong

TANGENTOD - Stretching and Filling Fuckpet Holes With Thong

BigTitsLust 1 month ago

Doggy style sissy training in a red dress and white pumps

Doggy style sissy training in a red dress and white pumps

XHamster 2 years ago

Training Ebony Sissy Aliza to serve a Large Weenie White Dad Spitroasting Cum in Throat Humiliation Unfathomable Mouth BWC

Training Ebony Sissy Aliza to serve a Large Weenie White Dad Spitroasting Cum in Throat Humiliation Unfathomable Mouth BWC

ShemaleSin 2 weeks ago

River Enza's step-sister is a filthy slut who loves to drill and gag on a hard cock

River Enza's step-sister is a filthy slut who loves to drill and gag on a hard cock

TrannyMovs 3 months ago

Dildo+lovense= Real Destroy Anal... My Two Favorite Toys Together

Dildo+lovense= Real Destroy Anal... My Two Favorite Toys Together

Flirt4Free 1 year ago

LEGAL lad attempt his assfuck to sqiurt and groaning for the very first time

LEGAL lad attempt his assfuck to sqiurt and groaning for the very first time

WebcamBros 10 months ago

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Screw Machine

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Screw Machine

PornFreeNow 10 months ago

Ema Devine Private Show

50% 4K 2:00 / 5:03

Ema Devine Private Show

Camster 1 year ago

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

AbTranny 5 years ago

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124,124 results found

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