Encouragement Videos - Trans (6,789)

Guided Sissy JOI - Cock Sucking, Spit & CEI

Guided Sissy JOI - Cock Sucking, Spit & CEI

xHamster 1 month ago

”Hot tbabe Korra Del Rio stretching her asshole & masturbating”

”Hot tbabe Korra Del Rio stretching her asshole & masturbating”

4Wank 2 years ago

Cum Tasting Encouragement with Zae

Cum Tasting Encouragement with Zae

xHamster 4 months ago

Swallow My Cum

xHamster 5 months ago

Just Outta Curiosity

65% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 2 years ago

You dont want to be heterosexual anymore

You dont want to be heterosexual anymore

Transvids.tv 7 months ago

Fucked a hole in the dressing room !

Fucked a hole in the dressing room !

xHamster 1 year ago

Dressed Up And Bullied

49% HD 0:10 / 13:38

Dressed Up And Bullied

LoyalFans 2 years ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

VikiPorn 4 months ago

”Hot tbabe Korra Del Rio stretching her asshole & masturbating”

”Hot tbabe Korra Del Rio stretching her asshole & masturbating”

Faptor 2 years ago

It's Not Gay If It's A Girl

68% HD 0:10 / 12:43

It's Not Gay If It's A Girl

LoyalFans 1 year ago

Naughty FTM Jaq Quicksilver Rubs Massive Dick On Cam

Naughty FTM Jaq Quicksilver Rubs Massive Dick On Cam

Wankoz 4 months ago

Busty shemale in a hot bikini faps her thick cock

Busty shemale in a hot bikini faps her thick cock

Katestube 1 year ago

Swallow My Cum

HD 0:39 / 15:15

FapHouse 5 months ago

How to become a slutty Sissy Bitch *4K*

How to become a slutty Sissy Bitch *4K*

Clips4sale 1 year ago

Watch this if you're GAY

57% 1:01 / 11:14

Watch this if you're GAY

FapHouse 3 years ago

Kimber Haven Fag encouragement

Kimber Haven Fag encouragement

Nuvid 2 years ago

Futa In The Goon Lagoon

64% HD 0:10 / 19:23

Futa In The Goon Lagoon

LoyalFans 5 months ago

Ts babe reach orgasm by jerking her stiff dick

Ts babe reach orgasm by jerking her stiff dick

Sheshaft 4 months ago

Mommy Encourages You to Worship Her Cock

Mommy Encourages You to Worship Her Cock

xHamster 11 months ago

Futanari Mistress Shows you How to Use a Chastity Cage!

Futanari Mistress Shows you How to Use a Chastity Cage!

xHamster 4 months ago

JOI CEI

HD 0:10 / 12:14

LoyalFans 1 month ago

Sissy Encouragement by Broken Sissy Joyce

67% HD 1:01 / 10:09

Sissy Encouragement by Broken Sissy Joyce

FapHouse 1 year ago

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

Fapnado 1 year ago

Special Creamed Chocolate Chip Cookies Treat

53% HD 1:01 / 18:34

Special Creamed Chocolate Chip Cookies Treat

FapHouse 4 months ago

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

xHamster 3 months ago

I Will Bang Your Gay Bum

I Will Bang Your Gay Bum

TransTube.tv 1 year ago

Seduced By Silk - Star Nine

58% HD 0:10 / 13:41

Seduced By Silk - Star Nine

LoyalFans 2 years ago

Sissy dick Suck Encouragement p

Sissy dick Suck Encouragement p

Katestube 3 years ago

Big cock trans girl giving bisexual encouragement

Big cock trans girl giving bisexual encouragement

xHamster 2 years ago

You Love Shemales

57% HD 0:39 / 8:45

You Love Shemales

FapHouse 5 months ago

Sissy johnson Suck Encouragement p

Sissy johnson Suck Encouragement p

Sheshaft 3 years ago

Cum ride with me

Cum ride with me

xHamster 1 year ago

Relax your Mind

Relax your Mind

aShemaleTube 1 year ago

SHEMALES MAKE YOU JERK OFF

60% HD 0:10 / 9:31

SHEMALES MAKE YOU JERK OFF

LoyalFans 4 months ago

CobraCummander - Bisexual Encouragement Mild Humiliation

CobraCummander - Bisexual Encouragement Mild Humiliation

DrTuber 1 month ago

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

aShemaleTube 4 months ago

Gentle Femdom Sph & Thong Try on

Gentle Femdom Sph & Thong Try on

xHamster 10 months ago

Big tits jerk off encouragement JOI

Big tits jerk off encouragement JOI

WinPorn 5 years ago

You Love Men

aShemaleTube 1 year ago

You're Coming Home with Me; Glamour Admiration & Topping Role Have Fun

You're Coming Home with Me; Glamour Admiration & Topping Role Have Fun

TrannyGem 5 years ago

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

TrannyGem 4 years ago

Switch Places Sissy

59% HD 0:10 / 9:50

Switch Places Sissy

LoyalFans 1 year ago

Sissy Encouragement

Sissy Encouragement

ShemaleSin 4 years ago

Plumber adventure

Plumber adventure

TwinksNHunks 1 year ago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

KeekAss 3 years ago

Gingerhead Tranny Faps Her Cock To Sissygasm

Gingerhead Tranny Faps Her Cock To Sissygasm

Xfeed 1 year ago

Girl encourages sissy play 7

Girl encourages sissy play 7

GayCK 2 years ago

Flirty Redhead Tgirl Beauty Oily Jerk-Off Tease

Flirty Redhead Tgirl Beauty Oily Jerk-Off Tease

Sheshaft 1 month ago

Jackie Israeli sissy encouraging you to become a slut

Jackie Israeli sissy encouraging you to become a slut

xHamster 3 years ago

Swallow My Cum

57% HD 1:01 / 15:15

FapHouse 5 months ago

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

xHamster 2 years ago

Andre Stone decides to start masturbating beside Leah Hayes

Andre Stone decides to start masturbating beside Leah Hayes

Katestube 1 month ago

CEI Chick Dick Adore

CEI Chick Dick Adore

TransTube.tv 1 year ago

Sissy In The Ladies Class

Sissy In The Ladies Class

LoyalFans 3 months ago

SISSYGASM ENCOURAGEMENT

65% HD 0:10 / 7:26

SISSYGASM ENCOURAGEMENT

LoyalFans 1 year ago

Public Bathroom Pegging

55% HD 0:10 / 15:32

Public Bathroom Pegging

LoyalFans 4 months ago

Trans nymph want you to spunk

Trans nymph want you to spunk

TrannyGem 5 months ago

Trainee sissy

xHamster 1 month ago

LONELY SISSY ENCOURAGEMENT GET YOUR MAN!

LONELY SISSY ENCOURAGEMENT GET YOUR MAN!

Tranny.one 4 years ago

GOONING FOR SHEMALES

59% HD 0:10 / 32:17

GOONING FOR SHEMALES

LoyalFans 3 months ago

[Audio] Parent's Bad Trans Stud

[Audio] Parent's Bad Trans Stud

5Gays 10 months ago

So You Want To Be a Girl?

61% HD 0:10 / 11:05

So You Want To Be a Girl?

LoyalFans 11 months ago

Gender Transformation Encouragement

42% HD 0:39 / 12:54

Gender Transformation Encouragement

FapHouse 1 year ago

cock sucking encouragement

cock sucking encouragement

Eporner 6 days ago

Tranny jerk off encouragement

Tranny jerk off encouragement

xHamster 2 years ago

Cum Lover Compilation 2

43% HD 0:10 / 11:46

Cum Lover Compilation 2

LoyalFans 1 year ago

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

TURNING YOU IN A SLUTTY SISSY READY FOR A HOT PARTY

xHamster 10 months ago

You Love Shemales

56% HD 0:39 / 8:45

You Love Shemales

FapHouse 5 months ago

Cock Conditioning For The Closeted Faggot

Cock Conditioning For The Closeted Faggot

xHamster 2 years ago

Mature guy seduced by a cute young twink into blowjobs and fucking

Mature guy seduced by a cute young twink into blowjobs and fucking

AllBoner 3 years ago

Bi Encouragement for secret sissy - FemDom

Bi Encouragement for secret sissy - FemDom

xHamster 4 months ago

Goth Transgirl Sucks Her Cock and Moans in Close-Up Cam Session

Goth Transgirl Sucks Her Cock and Moans in Close-Up Cam Session

Katestube 4 months ago

yui_kitano Summer Anal masturbation 2025

yui_kitano Summer Anal masturbation 2025

xHamster 6 months ago

YOU LOVE SHEMALES

56% HD 0:10 / 18:43

YOU LOVE SHEMALES

LoyalFans 5 months ago

Relaxing Scenes

Relaxing Scenes

aShemaleTube 1 year ago

ASMR: sissy, accept yourself! you are luved. Psychology. Mittens. Arya Grander

ASMR: sissy, accept yourself! you are luved. Psychology. Mittens. Arya Grander

4Gay 7 months ago

Innocence Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Innocence Sissygasm Compilation Encouragement - Sissy Jessica Bloom

KeekAss 1 year ago

Femdom's Cock-hungry Sissy Fetish Exposed

Femdom's Cock-hungry Sissy Fetish Exposed

Jizzberry 4 years ago

Ladyboy jack off encouragement

Ladyboy jack off encouragement

TrannyGem 2 years ago

Gingerhead Tranny Faps Her Dick To Sissygasm

Gingerhead Tranny Faps Her Dick To Sissygasm

Pornwhite 1 year ago

Carnal Domination & Oral-Sex Fixation CEI; Kiss Me from Head to Uncut Rod

Carnal Domination & Oral-Sex Fixation CEI; Kiss Me from Head to Uncut Rod

ShemaleSin 4 years ago

Positive Feminization - Wifey finds out crossdresser spouse and encourages. crossdressing ENG Audio

Positive Feminization - Wifey finds out crossdresser spouse and encourages. crossdressing ENG Audio

TrannyGem 6 months ago

Counselor dream- encouraged ambidextrous

Counselor dream- encouraged ambidextrous

TrannyGem 1 year ago

Hot BF worships by sucking and licking trans cock deep

Hot BF worships by sucking and licking trans cock deep

Pervclips 6 days ago

Gorgeous blonde teasingly strokes her cock

Gorgeous blonde teasingly strokes her cock

Fapcat 1 year ago

YOU WANT TO INHALE THE STIFF-ONS OF THE SHE-MASCULINES (eng) (preview- link on movie)

YOU WANT TO INHALE THE STIFF-ONS OF THE SHE-MASCULINES (eng) (preview- link on movie)

TransTube.tv 1 year ago

U R NOT TRANS- UR a SISSY - Positive Female dominance Sissification Feminization Autogynephillia POINT OF VIEW

U R NOT TRANS- UR a SISSY - Positive Female dominance Sissification Feminization Autogynephillia POINT OF VIEW

Transvids.tv 7 months ago

Petite Slim Blonde Trap Strokes her Cute Pink Boy Clit

Petite Slim Blonde Trap Strokes her Cute Pink Boy Clit

Sheshaft 2 years ago

Jerk off Whilst I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

Jerk off Whilst I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

ShemaleSin 2 years ago

SAY “I AM A FAGGOT MISTRESS RAVEN”

68% HD 0:10 / 23:45

SAY “I AM A FAGGOT MISTRESS RAVEN”

LoyalFans 3 years ago

Sissy Crossdresser Boyfriend Found Out and Pegged with Biggest Ding-cock by Hawt FemDom Girlfriend

Sissy Crossdresser Boyfriend Found Out and Pegged with Biggest Ding-cock by Hawt FemDom Girlfriend

Dafreeporn 3 months ago

You Jerk off Your Dick for the Cocks of Muscular Transsexuals Ita

You Jerk off Your Dick for the Cocks of Muscular Transsexuals Ita

xHamster 3 months ago

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

TransTube.tv 9 months ago

Blow My Sissy's Penis While I Boink You

Blow My Sissy's Penis While I Boink You

MenGem 2 years ago

Tranny Love Encouragement For Sissies

Tranny Love Encouragement For Sissies

aShemaleTube 3 months ago

transmidnight - ghost park petite asian tranny handles bbc bare

transmidnight - ghost park petite asian tranny handles bbc bare

TransDoe 1 year ago

Futa mommy wants to cuddle up close and fuck your tight little asshole with her big hard cock (FEMINIZATION ROLEPLAY - AI)

Futa mommy wants to cuddle up close and fuck your tight little asshole with her big hard cock (FEMINIZATION ROLEPLAY - AI)

xHamster 8 months ago

beCUM our GIRLfriend

beCUM our GIRLfriend

aShemaleTube 1 year ago

Swallow Your Cum Sissy CEI Encouragement Compilation Je

Swallow Your Cum Sissy CEI Encouragement Compilation Je

Eporner 2 months ago

TRANSFIXED - Christy Love Encourages Trans Clients To Fuck During Nude Massage

TRANSFIXED - Christy Love Encourages Trans Clients To Fuck During Nude Massage

aShemaleTube 4 years ago

SHEMALES MADE YOUR BRAIN POP - GOONING FOR SHEMALE

63% HD 0:10 / 39:27

SHEMALES MADE YOUR BRAIN POP - GOONING FOR SHEMALE

LoyalFans 6 months ago

Sissy Stupid Deep throats Alpha Jizz-shotgun for Domme

Sissy Stupid Deep throats Alpha Jizz-shotgun for Domme

TransTube.tv 8 months ago

U're Coming Home With Me - Topping Encouragement & Role Play

U're Coming Home With Me - Topping Encouragement & Role Play

ShemaleSin 4 years ago

Big tits jerk off encouragement JOI

Big tits jerk off encouragement JOI

IcePorn 6 years ago

Put A Ring On It & Lick Your Bride's man gravy: Wedding Night CEI fantasy

Put A Ring On It & Lick Your Bride's man gravy: Wedding Night CEI fantasy

Transvids.tv 4 months ago

Trans Positive JOI - KELLI FROST MENTAL ENCOURAGEMENT

Trans Positive JOI - KELLI FROST MENTAL ENCOURAGEMENT

Amateur8 3 years ago

Leah Hayes gets more instructions from Andre Stone while he gives her a wild anal ride

Leah Hayes gets more instructions from Andre Stone while he gives her a wild anal ride

Yeswegays 2 months ago

Hot boyfriend eagerly sucks and licks trans woman's big dick

Hot boyfriend eagerly sucks and licks trans woman's big dick

Katestube 1 month ago

Compelling CEI

Eporner 2 years ago

Pan porn with Kyle, Zariah Aura, and others

Pan porn with Kyle, Zariah Aura, and others

HOMO.XXX 1 year ago

I Heard You Might be Gay

I Heard You Might be Gay

xHamster 1 year ago

Smokin' mistresse Shelly

Smokin' mistresse Shelly

ShemaleSin 1 year ago

Tranny jerk off encouragement

Tranny jerk off encouragement

aShemaleTube 2 years ago

onlyfans - tslucylux tranny cumming while receiving an anal creampie

onlyfans - tslucylux tranny cumming while receiving an anal creampie

TransDoe 2 years ago

Girlcock for Boyfriend Bi Encouragement with Kimberly K

Girlcock for Boyfriend Bi Encouragement with Kimberly K

FetishShrine 1 year ago

Mandy Madison – Cross Dressing CEI Encouragement

Mandy Madison – Cross Dressing CEI Encouragement

IcePorn 1 year ago

Oiled-Up Redhead Trans Babe Edges for You

Oiled-Up Redhead Trans Babe Edges for You

FetishShrine 1 week ago

Eva Nova - First Time CEI Encouragement JOI

Eva Nova - First Time CEI Encouragement JOI

Nuvid 3 weeks ago

Tiny alt trans Mom Femdom-goddess gooner encouragement

Tiny alt trans Mom Femdom-goddess gooner encouragement

BigTitsLust 4 months ago

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