Encouragement Videos - Trans (6,614)

Trans goddess encourages you to explore your bisexual fantasies

Trans goddess encourages you to explore your bisexual fantasies

Clips4sale 1 week ago

Tranny jerk off encouragement

Tranny jerk off encouragement

xHamster 2 years ago

Woman Encourages Guy Transformation Makeover into Woman

Woman Encourages Guy Transformation Makeover into Woman

xHamster 8 months ago

Femdom's Cock-hungry Sissy Fetish Exposed

Femdom's Cock-hungry Sissy Fetish Exposed

Jizzberry 3 years ago

Kimber Haven Fag encouragement

Kimber Haven Fag encouragement

Nuvid 1 year ago

Busty shemale encourages her audience to masturbate more

Busty shemale encourages her audience to masturbate more

aShemaleTube 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

Falcon Studios: Pale athletic gymnast cumshot

Falcon Studios: Pale athletic gymnast cumshot

GayMenSexTube 3 years ago

Woman Encourages Guy Transformation Makeover into Woman

Woman Encourages Guy Transformation Makeover into Woman

PornoXO 8 months ago

** Am I Gay For Being Horny For Shemales? **

HD 0:35 / 24:03

** Am I Gay For Being Horny For Shemales? **

Clips4sale 1 month ago

Go Gay For My Girl-Cock (4KUHD MP4)

67% HD 0:32 / 15:55

Go Gay For My Girl-Cock (4KUHD MP4)

Clips4sale 6 months ago

I Will Fuck Your Faggot Ass

48% 0:27 / 7:16

I Will Fuck Your Faggot Ass

Clips4sale 2 years ago

Trans Porn Addiction Encouragement JOI

60% HD 0:30 / 14:11

Trans Porn Addiction Encouragement JOI

Clips4sale 9 months ago

YOU ARE GAY

65% HD 0:21 / 13:35

Clips4sale 1 year ago

Are you GAY? Or do you just like COCK?

47% 0:11 / 3:07

Are you GAY? Or do you just like COCK?

C4S 2 years ago

Trans Femboy Solo Masturbation Asshole Girlcock Ass Spreading Sunlight

Trans Femboy Solo Masturbation Asshole Girlcock Ass Spreading Sunlight

xHamster 2 months ago

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

LONELY SISSY ENCOURAGEMENT GET YOUR STUD!

TrannyGem 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 1 month ago

Faggot Fantasies

41% HD 0:11 / 8:12

Faggot Fantasies

Clips4sale 3 years ago

Hung trans girl giving bisexual encouragement

Hung trans girl giving bisexual encouragement

xHamster 9 months ago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

Homosexual Encouragement and Cumdump Cravings - Adore Holland Of Chicago

KeekAss 3 years ago

Sissy Encouragement

Sissy Encouragement

ShemaleSin 4 years ago

when you bring her home and turns out that she has a cock bigger than yours

when you bring her home and turns out that she has a cock bigger than yours

Hupoz 2 weeks 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

Big tits jerk off encouragement JOI

Big tits jerk off encouragement JOI

IcePorn 5 years ago

Counselor dream- encouraged ambidextrous

Counselor dream- encouraged ambidextrous

TrannyGem 8 months ago

Tranny Ain't Even Pull Over And Was Sucking Cock While Driving LOL

Tranny Ain't Even Pull Over And Was Sucking Cock While Driving LOL

PublicSextube 1 month ago

Entranced and Encouraged by a Feminizing Lady

Entranced and Encouraged by a Feminizing Lady

YouPorn Unknown

Suck My Sissy&#039_s Cock While I Fuck You

Suck My Sissy&#039_s Cock While I Fuck You

XVideos 7 years ago

bisexual compilation take it

bisexual compilation take it

3xcg 1 year ago

Suck Your First Trans Cock at the Gloryhole

76% 0:30 / 8:25

Suck Your First Trans Cock at the Gloryhole

Clips4sale 1 year ago

Conversion Mistress

74% 0:29 / 15:02

Conversion Mistress

Clips4sale 2 years ago

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

xHamster 3 years ago

Fucking Slave with Ladyboy Friend ft Mari Ayanami

76% 0:19 / 17:39

Fucking Slave with Ladyboy Friend ft Mari Ayanami

Clips4sale 1 year ago

Cock Conditioning For The Closeted Faggot

Cock Conditioning For The Closeted Faggot

xHamster 1 year ago

Compelling CEI

Eporner 1 year ago

Sissy CEI

48% 0:11 / 9:41

Clips4sale 2 years ago

Swallow My Cum

HD 0:39 / 15:15

FapHouse 3 days ago

Your Gay Affair Training Tasks

66% HD 0:29 / 10:42

Your Gay Affair Training Tasks

Clips4sale 2 months ago

Fucked a hole in the dressing room !

Fucked a hole in the dressing room !

xHamster 1 year ago

Unlearning to use your Cock

65% HD 0:29 / 10:56

Unlearning to use your Cock

Clips4sale 2 weeks ago

Shemale cock worship

66% 4K 0:30 / 17:53

Shemale cock worship

Clips4sale 2 years ago

You Cant Wear That To School - S15:E8

You Cant Wear That To School - S15:E8

Hoes.tube 2 years ago

The Gay Awakening Podcast Episode #44 - Gaped By SheMales

60% HD 0:19 / 10:10

The Gay Awakening Podcast Episode #44 - Gaped By SheMales

Clips4sale 2 years ago

The Ultimate SheMale Mind Fuck

50% HD 0:28 / 27:17

The Ultimate SheMale Mind Fuck

Clips4sale 11 months ago

Sissification of Rosie - Pt1

63% HD 0:53 / 13:38

Sissification of Rosie - Pt1

Clips4sale 1 year ago

Strapon Sissy Encouragement

HD 0:39 / 10:36

Strapon Sissy Encouragement

FapHouse 6 months ago

Shemale Turns You Gay

48% 0:10 / 13:20

Shemale Turns You Gay

C4S 4 months ago

YOU LOVE TRANS PENIS - Jessica Dynamic

49% HD 0:28 / 6:55

YOU LOVE TRANS PENIS - Jessica Dynamic

Clips4sale 1 year ago

Sissy johnson Suck Encouragement p

Sissy johnson Suck Encouragement p

Sheshaft 2 years ago

The Power of My COCK

66% HD 0:29 / 9:22

The Power of My COCK

Clips4sale 7 months ago

Sissy Oral Fun Pt1

66% HD 0:27 / 10:09

Sissy Oral Fun Pt1

Clips4sale 11 months 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 1 year ago

Gay Cum Eating Reprogramming CEI

54% 0:29 / 9:32

Gay Cum Eating Reprogramming CEI

Clips4sale 2 years ago

Girlcock for Boyfriend Bi Encouragement with Kimberly K

Girlcock for Boyfriend Bi Encouragement with Kimberly K

FetishShrine 1 year ago

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 MP4

57% HD 0:22 / 11:39

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 MP4

Clips4sale 3 months ago

Girl Cock Is Not GAY - Bella Trixxx Cock Worship Encouragement - AUDIO ONLY

55% HD 0:30 / 7:01

Girl Cock Is Not GAY - Bella Trixxx Cock Worship Encouragement - AUDIO ONLY

Clips4sale 6 months ago

** Shemale Strip Club **

58% HD 0:27 / 31:32

** Shemale Strip Club **

Clips4sale 2 months ago

Nylon Bitchs Ruined Orgasm

64% 0:06 / 5:53

Nylon Bitchs Ruined Orgasm

Clips4sale 7 months ago

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

44% 0:30 / 17:59

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

Clips4sale 8 months ago

Encouraged into Sissyhood

Encouraged into Sissyhood

BeMyHole 5 years ago

Femboy with blonde hair and black lipstick

Femboy with blonde hair and black lipstick

xHamster 9 months ago

Cum ride with me

Cum ride with me

xHamster 1 year ago

You Love Men

aShemaleTube 1 year 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

Supersweaty Asshole in Yogapants/worship

62% HD 0:39 / 41:39

Supersweaty Asshole in Yogapants/worship

FapHouse 1 month ago

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

Fapnado 1 year ago

Cock & Sole The Filthy Choice

60% 0:35 / 10:43

Cock & Sole The Filthy Choice

Clips4sale 5 days ago

yui_kitano Summer Anal masturbation 2025

yui_kitano Summer Anal masturbation 2025

xHamster 1 month ago

Stockings granny encouraging bisexual 3some MMF

Stockings granny encouraging bisexual 3some MMF

PornGem 1 year 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 4 years ago

Sissy dick Suck Encouragement p

Sissy dick Suck Encouragement p

FetishShrine 1 year ago

WRAP YOUR LIPS AROUND COCK

69% HD 0:10 / 16:17

WRAP YOUR LIPS AROUND COCK

LoyalFans 2 years ago

Its NOT GAY if its SHEMALES

44% HD 0:15 / 32:34

Its NOT GAY if its SHEMALES

Clips4sale 8 months ago

Anal Ass-Fucking Frenzy #2 - Anal Sex with Transgender Model & Pornstar Eris Joli

Anal Ass-Fucking Frenzy #2 - Anal Sex with Transgender Model & Pornstar Eris Joli

4KPorn 1 month ago

All You Need - S37:E21

All You Need - S37:E21

Hoes.tube 2 years ago

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

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

Zatube 1 year ago

Thai Temptation 2: Cock And Submission - Two Holes, One Mistress

43% 0:30 / 20:02

Thai Temptation 2: Cock And Submission - Two Holes, One Mistress

Clips4sale 4 months ago

It's Not Gay If It's A Girl

62% HD 0:10 / 12:43

It's Not Gay If It's A Girl

LoyalFans 9 months 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 2 years ago

Plump Inked Tranny Encourages You To Cum With Her Whispering JOI And Wanking On Camera

Plump Inked Tranny Encourages You To Cum With Her Whispering JOI And Wanking On Camera

XGroovy 2 years ago

Relaxing Scenes

Relaxing Scenes

aShemaleTube 10 months ago

Your first time swallowing cum

62% 0:30 / 11:59

Your first time swallowing cum

Clips4sale 2 years ago

We Like You Better as a Girl

44% HD 0:26 / 10:54

We Like You Better as a Girl

Clips4sale 1 year ago

Let Me Watch More - S33:E14

Let Me Watch More - S33:E14

Hoes.tube 2 years ago

Girl encourages sissy play 5

Girl encourages sissy play 5

GayCK 3 years ago

May 2022 Fantasy Of The Month - S3:E4

May 2022 Fantasy Of The Month - S3:E4

Hoes.tube 2 years ago

Sissy Instructing - Sissygasm Encouragement Jessica Bloom Compilation

Sissy Instructing - Sissygasm Encouragement Jessica Bloom Compilation

KeekAss 3 years ago

I KNOW YOURE NOT GAY

47% 4K 0:25 / 17:09

I KNOW YOURE NOT GAY

Clips4sale 2 years ago

Naked Busty Ts Ass Flash On Her Camshow

Naked Busty Ts Ass Flash On Her Camshow

FetishShrine 1 year ago

Worship Holland Of Chicago - Jerk Off To A Hot Lingerie and Leather Goddess and Go Gay For Me

Worship Holland Of Chicago - Jerk Off To A Hot Lingerie and Leather Goddess and Go Gay For Me

xHamster 3 years ago

Sexy shemale Korra Del Rio stretching her butthole and masturbating

Sexy shemale Korra Del Rio stretching her butthole and masturbating

Fapnado 3 years ago

[Audio] Your Sisters Bf Thinks You're Red-Hot in Chicks Clothes

[Audio] Your Sisters Bf Thinks You're Red-Hot in Chicks Clothes

4Gay 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

Sissy dick Suck Encouragement p

Sissy dick Suck Encouragement p

Katestube 2 years ago

Eat Cum for Me CEI JOI

66% HD 0:27 / 10:33

Eat Cum for Me CEI JOI

Clips4sale 2 years ago

Trap In Black Stockings Stroking Her Thick Cock

Trap In Black Stockings Stroking Her Thick Cock

FetishShrine 1 year ago

[ASMR] Positive Sissy Reinforcement - Audio Only

41% HD 0:30 / 12:03

[ASMR] Positive Sissy Reinforcement - Audio Only

Clips4sale 5 months ago

Gorgeous blonde teasingly strokes her cock

Gorgeous blonde teasingly strokes her cock

SleazyNEasy 7 months ago

Hot tbabe Korra Del Rio stretching her asshole & masturbating

Hot tbabe Korra Del Rio stretching her asshole & masturbating

Faptor 2 years ago

trans jerk off instructions with text guidelines & lots of jizm

trans jerk off instructions with text guidelines & lots of jizm

TrannyGem 1 year ago

pov squeezing your big cock inside your boyfriend`s tight submissive boy pussy gay couple anal sex raw

pov squeezing your big cock inside your boyfriend`s tight submissive boy pussy gay couple anal sex raw

PornBox 1 year ago

Spray & Splay My Cheeks

Spray & Splay My Cheeks

Hoes.tube 2 years ago

You dont want to be Straight anymore

68% 0:37 / 12:06

You dont want to be Straight anymore

Clips4sale 4 months ago

Caught My Boyfriend Cheating With A Tranny Part 1

56% HD 0:25 / 13:02

Caught My Boyfriend Cheating With A Tranny Part 1

Clips4sale 2 years ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

xHamster 3 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 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 1 month 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

You dont want to be heterosexual anymore

You dont want to be heterosexual anymore

Transvids.tv 2 months 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

Trans Femboy Solo Masturbation Asshole Girlcock Ass Spreading Sunlight

Trans Femboy Solo Masturbation Asshole Girlcock Ass Spreading Sunlight

xHamster 3 months ago

Suck Her Big Cock -Serve My Ladyboy Friend- ft Mari Ayanami

57% 0:16 / 12:47

Suck Her Big Cock -Serve My Ladyboy Friend- ft Mari Ayanami

Clips4sale 1 year ago

Gentle Femdom Sph & Thong Try on

Gentle Femdom Sph & Thong Try on

xHamster 4 months ago

i bet you would find me in shemale paradise

i bet you would find me in shemale paradise

3xcg 11 months ago

Nude To The Neighborhood

Nude To The Neighborhood

Kojka 2 years ago

Cum to Gay Porn JOI

70% HD 0:30 / 11:53

Cum to Gay Porn JOI

Clips4sale 2 years ago

Kevin's Helper

TrannyGem 3 years ago

Strokes Her Dick

Strokes Her Dick

Sheshaft 1 year ago

Aubrey Kate Finds Solace In Sodomizing Fellow Horny Widow

Aubrey Kate Finds Solace In Sodomizing Fellow Horny Widow

LoveTranSex 8 months ago

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