Encouragement Videos - Trans (1,618)

Mommy Encourages You to Worship Her Cock

Mommy Encourages You to Worship Her Cock

xHamster 2 months 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 4 years ago

Be our gym sissy cuck in purity BELLA BLU - LUCY HART

Be our gym sissy cuck in purity BELLA BLU - LUCY HART

TrannyGem 1 year ago

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

TrannyGem 3 years ago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

KeekAss 2 years ago

LONELY SISSY ENCOURAGEMENT GET YOUR MAN!

LONELY SISSY ENCOURAGEMENT GET YOUR MAN!

Tranny.one 3 years ago

Trans lady gives Jerk Off Instructions jilling instructions for her girlfriend

Trans lady gives Jerk Off Instructions jilling instructions for her girlfriend

TransTube.tv 9 months ago

TS PMV - Physical � Dua Lipa Encourages You to Jerk Off

TS PMV - Physical � Dua Lipa Encourages You to Jerk Off

Tranny.one 3 years ago

Crossing your wires: Ambisexual encouragemenet Jerk Off Instructions

Crossing your wires: Ambisexual encouragemenet Jerk Off Instructions

TrannyGem 3 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

ts girls masturbation and cumshot compilation

ts girls masturbation and cumshot compilation

Shemale TS 9 months ago

Vagina Virgins

Kojka 1 year ago

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

Fapnado 9 months ago

Gay Encouragement and Cumdump Fantasies - Worship Holland Of Chicago

Gay Encouragement and Cumdump Fantasies - Worship Holland Of Chicago

xHamster 2 years ago

Skinny Cutie

aShemaleTube 2 years ago

Sissy Encouragement by Broken Sissy Joyce

66% HD 1:01 / 10:09

Sissy Encouragement by Broken Sissy Joyce

FapHouse 10 months ago

You Love Men

aShemaleTube 10 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 3 weeks ago

Trans Femdom Large Penis Sissy Encouragement - Jessica Bloom

Trans Femdom Large Penis Sissy Encouragement - Jessica Bloom

ShemaleSin 1 year ago

Big cock trans girl giving bisexual encouragement

Big cock trans girl giving bisexual encouragement

xHamster 2 years ago

Locked Down and Loving It Hoe 2

Locked Down and Loving It Hoe 2

Hoes.tube 1 month ago

ts tsvegasvalentine your first load

ts tsvegasvalentine your first load

Shemale TS 1 year ago

Sissy dick Suck Encouragement p

Sissy dick Suck Encouragement p

Katestube 2 years ago

Sissy Get Your Man

Sissy Get Your Man

aShemaleTube 6 years ago

Femdom's Cock-hungry Sissy Fetish Exposed

Femdom's Cock-hungry Sissy Fetish Exposed

Jizzberry 3 years ago

Observe Me Witness u - Personal POINT OF VIEW Onanism

Observe Me Witness u - Personal POINT OF VIEW Onanism

TrannyGem 4 years ago

GFE RP JOI - you first Time Wearing Underwear - FULL SCENE

GFE RP JOI - you first Time Wearing Underwear - FULL SCENE

4KPorn 3 years ago

Gorgeous blonde teasingly strokes her cock

Gorgeous blonde teasingly strokes her cock

Pornicom 4 months ago

Sissy dick Suck Encouragement p

Sissy dick Suck Encouragement p

FetishShrine 9 months ago

Cum ride with me

Cum ride with me

xHamster 1 year ago

GFE RP JOI - you first Time Wearing Underwear - FULL CLIP

GFE RP JOI - you first Time Wearing Underwear - FULL CLIP

CrazyPorn 3 years ago

Spray & Splay My Cheeks

Spray & Splay My Cheeks

Hoes.tube 1 year ago

Limp Sissy Maker

Limp Sissy Maker

Eporner 5 years ago

Sissy Encouragement

Sissy Encouragement

ShemaleSin 4 years ago

Gingerhead Tranny Faps Her Cock To Sissygasm

Gingerhead Tranny Faps Her Cock To Sissygasm

CrazyPorn 7 months ago

Sissy Instructing - Sissygasm Encouragement Jessica Bloom Compilation

Sissy Instructing - Sissygasm Encouragement Jessica Bloom Compilation

KeekAss 3 years ago

Giving In With My StepSister - S28:E5

Giving In With My StepSister - S28:E5

Hoes.tube 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 2 months 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

TransTube.tv 5 months ago

Gingerhead Tranny Faps Her Cock To Sissygasm

Gingerhead Tranny Faps Her Cock To Sissygasm

SukaPorn 9 months ago

May 2022 Fantasy Of The Month - S3:E4

May 2022 Fantasy Of The Month - S3:E4

Hoes.tube 2 years ago

Sissy licks Alpha's schlong And Takes A Messy Facial While Dominatrix Whispers Encouragement

Sissy licks Alpha's schlong And Takes A Messy Facial While Dominatrix Whispers Encouragement

DeegX 1 year ago

Disposable Holes

Disposable Holes

xHamster 2 months ago

She caught him in pantyhose and they both got turned on

She caught him in pantyhose and they both got turned on

xHamster 1 year ago

Pierce Paris Pranks Lily Demure: A NSFW Twist & Unexpected Outcome

Pierce Paris Pranks Lily Demure: A NSFW Twist & Unexpected Outcome

4Wank 1 year ago

Mommy Encourages You to Worship Her Cock

Mommy Encourages You to Worship Her Cock

FapHouse 2 months ago

All You Need - S37:E21

All You Need - S37:E21

Hoes.tube 2 years ago

Hottie In The Kitchen - S12:E2

Hottie In The Kitchen - S12:E2

Hoes.tube 1 year ago

Big tits jerk off encouragement JOI

Big tits jerk off encouragement JOI

IcePorn 5 years ago

Cum On Me Before Your Fiance Gets Back

Cum On Me Before Your Fiance Gets Back

Love4Porn 4 years ago

Play time with Rabeche

Play time with Rabeche

aShemaleTube 7 months ago

Ac/dc Knob Deep-sucking Encouragement ft Trans Femdominance

Ac/dc Knob Deep-sucking Encouragement ft Trans Femdominance

TransTube.tv 8 months ago

Sissy tasks - Gay Encouragement - FemDom

Sissy tasks - Gay Encouragement - FemDom

DaNude 11 months ago

Compelling CEI

Eporner 1 year ago

Chain Smoking Goth Slut Jack off until she Cums

Chain Smoking Goth Slut Jack off until she Cums

TrannyGem 6 years ago

Blow My Sissy's Penis While I Boink You

Blow My Sissy's Penis While I Boink You

MenGem 1 year ago

Stepbro, Your Cock is BIGGER Than You Think! S37E2

Stepbro, Your Cock is BIGGER Than You Think! S37E2

Hoes.tube 3 months ago

Sissy johnson Suck Encouragement p

Sissy johnson Suck Encouragement p

Sheshaft 2 years ago

Counselor dream- encouraged ambidextrous

Counselor dream- encouraged ambidextrous

TrannyGem 6 months ago

Busty Trans Showing Her Shecock and Big Boobs

Busty Trans Showing Her Shecock and Big Boobs

Katestube 1 year ago

Encouraged into Sissyhood

Encouraged into Sissyhood

BeMyHole 4 years ago

Pierce Paris Pranks Lily Demure: A NSFW Twist & Unexpected Outcome

Pierce Paris Pranks Lily Demure: A NSFW Twist & Unexpected Outcome

Rainblow 11 months ago

CEI Damsel Man Rod Idolize

CEI Damsel Man Rod Idolize

TrannyGem 1 year ago

Halloween Party Dress up: Cross Dressing & Bi Encouragement From Your Girlfriend

Halloween Party Dress up: Cross Dressing & Bi Encouragement From Your Girlfriend

xHamster 1 year ago

SISSY POV - Grab the PINK PILL!! Feminization Encouragement

SISSY POV - Grab the PINK PILL!! Feminization Encouragement

Kams.com 6 months ago

Kimber Haven Fag encouragement

Kimber Haven Fag encouragement

Nuvid 1 year ago

Mesmerize for Ass-Fuck Bottoms

Mesmerize for Ass-Fuck Bottoms

TrannyGem 3 years ago

Pretty femboy gives you bisexual encouragement

Pretty femboy gives you bisexual encouragement

ZBPorn 11 years ago

DILF Encouraged To Do Gay Porn By His Girlfriend

DILF Encouraged To Do Gay Porn By His Girlfriend

xHamster 3 years ago

Surrender to Your Sissy Desires, Worshipped by Femdom & Fetish Queens

Surrender to Your Sissy Desires, Worshipped by Femdom & Fetish Queens

Jizzberry 3 years ago

Gorgeous blonde teasingly strokes her cock

Gorgeous blonde teasingly strokes her cock

Eporner 4 months ago

Deepthroat Seduction Blonde Bombshell Devours Shemale Love Stick

Deepthroat Seduction Blonde Bombshell Devours Shemale Love Stick

4KPorn 3 months ago

Woman Encourages Guy Transformation Makeover into Woman

Woman Encourages Guy Transformation Makeover into Woman

xHamster 5 months ago

beCUM our GIRLfriend

beCUM our GIRLfriend

aShemaleTube 9 months ago

Relaxing Scenes

Relaxing Scenes

aShemaleTube 7 months ago

I play with my cock, you will enjoy watching my videos

I play with my cock, you will enjoy watching my videos

xHamster 7 months ago

[Audio] Parent's Bad Trans Stud

[Audio] Parent's Bad Trans Stud

5Gays 2 months ago

Newest Bisexual Encouragement Seductive

57% 0:39 / 3:53

Newest Bisexual Encouragement Seductive

FapHouse 10 months ago

Sissy Victim's Very First Bad Dragon Spreading Sesh with E-stim Encouragement by Domme Mercer

Sissy Victim's Very First Bad Dragon Spreading Sesh with E-stim Encouragement by Domme Mercer

TrannyGem 2 years ago

Femdom Sextoy Encouragement Suck my Jock Sissy POV Rollplay

Femdom Sextoy Encouragement Suck my Jock Sissy POV Rollplay

ShemaleSin 2 years ago

Glamorous TS In Fishnet Outfit

Glamorous TS In Fishnet Outfit

Sheshaft 5 years ago

Fucked a hole in the dressing room !

Fucked a hole in the dressing room !

xHamster 1 year ago

Trans Foot Fetish - Cum Eating Instructions Jessica Bloom JoI CEI

Trans Foot Fetish - Cum Eating Instructions Jessica Bloom JoI CEI

xHamster 3 years ago

Stockings granny encouraging bisexual 3some MMF

Stockings granny encouraging bisexual 3some MMF

PornGem 1 year ago

Chubby Laura Louise experiences a mouth and rough fucking

Chubby Laura Louise experiences a mouth and rough fucking

VikiPorn 1 month ago

Transgender Surprise Dream Come True

Transgender Surprise Dream Come True

TrannyGem 4 months ago

Girlcock for Boyfriend Bi Encouragement with Kimberly K

Girlcock for Boyfriend Bi Encouragement with Kimberly K

FetishShrine 10 months ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

Tranny.one 3 years ago

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

xHamster 1 year ago

Ladyboy jack off encouragement

Ladyboy jack off encouragement

TrannyGem 2 years ago

Fingering at Hole

54% HD 1:01 / 6:38

Fingering at Hole

FapHouse 4 months ago

Jessica Dynamic - FemDom Simp Encouragement to Trans Porn

Jessica Dynamic - FemDom Simp Encouragement to Trans Porn

IcePorn 4 weeks ago

The sissy otter munches his cummies for me

The sissy otter munches his cummies for me

TrannyGem 3 years ago

BLACK TGIRLS - Kayla Biggs Wants You To Desire Her Booty

BLACK TGIRLS - Kayla Biggs Wants You To Desire Her Booty

Trashreality 7 months ago

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

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

ShemaleSin 3 years ago

I Was Bullied By A Group Of Girls In My Class And Got An Erection, And Rima Arai's Weak Dick Encouragement Fellatio With The Kansai Dialect Of The Transfer Student Rima Arai.

I Was Bullied By A Group Of Girls In My Class And Got An Erection, And Rima Arai's Weak Dick Encouragement Fellatio With The Kansai Dialect Of The Transfer Student Rima Arai.

Eporner 8 months ago

Innocence Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Innocence Sissygasm Compilation Encouragement - Sissy Jessica Bloom

KeekAss 3 months ago

Nurse Nikki Handles your Buttfuck Female Domination Dream and Tops you nicer

Nurse Nikki Handles your Buttfuck Female Domination Dream and Tops you nicer

TrannyGem 3 years ago

Ts Rianna James – Bimbo Encouragement. Mommy Is Going To

Ts Rianna James – Bimbo Encouragement. Mommy Is Going To

DrTuber 2 years ago

Ashton Blake: Dirty Talking Instructor

Ashton Blake: Dirty Talking Instructor

Some.Porn 5 months ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 7 months ago

Gentle feminization: taking the first step towards becoming a woman 1/7

Gentle feminization: taking the first step towards becoming a woman 1/7

XXXShemalePorn 1 year ago

Crossdressing gay anal with Danny Jones and Johny Walsh

Crossdressing gay anal with Danny Jones and Johny Walsh

HOMO.XXX 4 years ago

Tranny jerk off encouragement

Tranny jerk off encouragement

xHamster 2 years ago

Sweaty Squats and Insatiable Lust

Sweaty Squats and Insatiable Lust

Hoes.tube 2 months ago

Crossdressing Pervert's Return - Part 2

Crossdressing Pervert's Return - Part 2

xHamster 1 year ago

Femboy with blonde hair and black lipstick

Femboy with blonde hair and black lipstick

xHamster 7 months ago

Cute TRANS BEAUTY gives u INSTRUCTIONS to JERK OFF

Cute TRANS BEAUTY gives u INSTRUCTIONS to JERK OFF

ShemaleSin 10 months ago

Bi Weenie Sucking Encouragement ft Trans Femdom

Bi Weenie Sucking Encouragement ft Trans Femdom

ShemaleSin 1 year ago

Large tits Angel Ducati showcases her dong

Large tits Angel Ducati showcases her dong

TransHero 3 years ago

Nude To The Neighborhood

Nude To The Neighborhood

Kojka 2 years ago

Goddess Yata - Cum Slut Encouragement

Goddess Yata - Cum Slut Encouragement

IcePorn 1 month ago

Your Sissy Destiny - Sissification Encouragement Affirmation FULL VID on LayneLovee Manyvids

Your Sissy Destiny - Sissification Encouragement Affirmation FULL VID on LayneLovee Manyvids

BallsAndBoobs 6 months ago

Bossy T-girl Lena Moon dominates guy and makes him eat cum

Bossy T-girl Lena Moon dominates guy and makes him eat cum

XGroovy 1 year ago

Trial Separation

Trial Separation

PornOne 9 months ago

stroking encouragement

stroking encouragement

Sheshaft 5 years ago

Hot tbabe Korra Del Rio stretching her asshole & masturbating

Hot tbabe Korra Del Rio stretching her asshole & masturbating

StarWank 1 year ago

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

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

TransG 1 year ago

Hot trans Venus Lux fucks Military guy in tight ass

Hot trans Venus Lux fucks Military guy in tight ass

MyLust 2 years ago

Fabri ka sissy ta cherie et toi sissy

Fabri ka sissy ta cherie et toi sissy

AbTranny 7 years ago

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