Encouragement Videos - Trans (4,391)

SO, YOU WANNA BE MY SISSY? *HD 1080*

HD 0:29 / 13:35

SO, YOU WANNA BE MY SISSY? *HD 1080*

Clips4sale 1 year ago

meu amigo da faculdade tinha a rola bem grossa

meu amigo da faculdade tinha a rola bem grossa

PornBox 1 month ago

So You Want To Be a Girl?

HD 0:10 / 11:05

So You Want To Be a Girl?

LoyalFans 3 months ago

Homewrecked By Shemale (1080p)

56% HD 0:42 / 10:35

Homewrecked By Shemale (1080p)

Clips4sale 4 months ago

Cock Whore Begs For More

4K 0:30 / 40:34

Cock Whore Begs For More

Clips4sale 2 years ago

Good Girl Sissy Pegging Audio

HD 0:11 / 10:10

Good Girl Sissy Pegging Audio

Clips4sale 1 year ago

Meditative Futanari JOI - gay, make me bi, futa, ASMR

Meditative Futanari JOI - gay, make me bi, futa, ASMR

Clips4sale 1 week ago

Sissy to Cock Sucker Pipeline

HD 0:25 / 10:14

Sissy to Cock Sucker Pipeline

Clips4sale 8 months ago

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Premium HD 12:28

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Clips4sale 11 months ago

Shemale Fucktoy *HD*

Shemale Fucktoy *HD*

Clips4sale 2 weeks ago

Strap On GF and CEI Punishment

56% HD 0:11 / 11:59

Strap On GF and CEI Punishment

Clips4sale 3 years ago

Sweet Surprise: Your App Hookup is Secretly a Trans Guy! - 1080p

Sweet Surprise: Your App Hookup is Secretly a Trans Guy! - 1080p

Clips4sale 1 year ago

Cock Sucking Return to Cock (MOV)

Cock Sucking Return to Cock (MOV)

Clips4sale 2 years ago

Your Girlfriend Will Pay For Your First Shemale Experience

Your Girlfriend Will Pay For Your First Shemale Experience

C4S 2 years ago

Striaght boy curious fuckign latina transexuel big boob and big dick hot

Premium HD 26:54

Striaght boy curious fuckign latina transexuel big boob and big dick hot

Sheer 1 year ago

this guy will not live me alone

this guy will not live me alone

AnalVids 2 weeks ago

Futa Pegging POV Vol 1

HD 0:28 / 58:21

Futa Pegging POV Vol 1

TURNING SISSY SLUT INTO MY PET

64% 4K 0:27 / 18:01

TURNING SISSY SLUT INTO MY PET

Clips4sale 1 year ago

Faggot Ravished by BBC JOI Cum Countdown

Faggot Ravished by BBC JOI Cum Countdown

Clips4sale 1 year ago

Tranny lover

Clips4sale 6 months ago

this guy will not live me alone

this guy will not live me alone

PornBox 1 week ago

Taking it to the Next Level 1080p mp4

Taking it to the Next Level 1080p mp4

Clips4sale 1 year ago

THE GAY AWAKENING 2 PODCAST: EPISODE #20: SISSY HALEN FOR BBC CO-WORKER

56% 4K 0:25 / 13:31

THE GAY AWAKENING 2 PODCAST: EPISODE #20: SISSY HALEN FOR BBC CO-WORKER

Clips4sale 2 years ago

TINY BIMBOS PAID NIGHTMARE - TITS EXPANDED & USED BY GIANT FUTAS

HD 0:10 / 25:11

TINY BIMBOS PAID NIGHTMARE - TITS EXPANDED & USED BY GIANT FUTAS

LoyalFans 1 month ago

Suck Your First Trans Cock at the Gloryhole

75% 0:30 / 8:25

Suck Your First Trans Cock at the Gloryhole

Clips4sale 1 year ago

Sissy Slut Swallows Sissygasm - CEI JOI Cum Eating Instructions by Goddess Nikki Kit

58% HD 0:25 / 9:39

Sissy Slut Swallows Sissygasm - CEI JOI Cum Eating Instructions by Goddess Nikki Kit

Clips4sale 5 months ago

Futa Pegging POV Vol 1

HD 0:28 / 58:21

Futa Pegging POV Vol 1

Clips4sale 2 years ago

filling sexy with my niga

filling sexy with my niga

PornBox 4 days ago

Luke Hudson and Jack Bailey | Chapter 7

HD 0:59 / 23:49

Luke Hudson and Jack Bailey | Chapter 7

JockPussy 1 year ago

Slut Training PT2 - lets make use the teeth for a reason! -

Slut Training PT2 - lets make use the teeth for a reason! -

Clips4sale 1 year ago

so hot on me

AnalVids 2 weeks ago

Part 1: sissy sleepover and encouraged bi cock sucking humiliation for sissy bitch with Mistress L Hush

45% 0:11 / 10:38

Part 1: sissy sleepover and encouraged bi cock sucking humiliation for sissy bitch with Mistress L Hush

Clips4sale 2 years ago

Trans-Mommy Natalie Carnot's Panty Sniffing Puppy Boy

56% HD 0:13 / 14:10

Trans-Mommy Natalie Carnot's Panty Sniffing Puppy Boy

Clips4sale 8 months ago

Sissy Anal JOI + CEI

45% HD 0:28 / 12:44

Sissy Anal JOI + CEI

Clips4sale 1 year ago

Pimped in the gay club

56% HD 0:15 / 13:42

Pimped in the gay club

Clips4sale 3 years ago

Estrogen Encouragement

Estrogen Encouragement

Clips4sale 2 months ago

Sissy Task for Sissies

56% HD 0:20 / 6:11

Sissy Task for Sissies

Clips4sale 9 months ago

the two muclar guys got me in my friends place fucking hot

the two muclar guys got me in my friends place fucking hot

PornBox 2 weeks ago

Gay Boy Counseling

Gay Boy Counseling

Clips4sale 2 years ago

My 7 Inch Dick Owns You

My 7 Inch Dick Owns You

Clips4sale 2 years ago

FemDom Simp Encouragement to Trans Porn - Jessica Dynamic JessicaDynamic Jessica_Dynamic

FemDom Simp Encouragement to Trans Porn - Jessica Dynamic JessicaDynamic Jessica_Dynamic

Clips4sale 2 years ago

Sissy dicklet rating & training

Sissy dicklet rating & training

Clips4sale 2 years ago

Become My Femme Bestie Fill-In To Date Me

Become My Femme Bestie Fill-In To Date Me

Clips4sale 1 year ago

Pay the small cock tax to the Futanari

Pay the small cock tax to the Futanari

Clips4sale 2 years ago

Homewrecked by Trans Tits Mindfuck

61% 0:30 / 11:23

Homewrecked by Trans Tits Mindfuck

Clips4sale 1 year ago

Be Our Cheerleader

58% 0:06 / 6:02

Be Our Cheerleader

Clips4sale 2 months ago

White Boy Ruin - Mindfucked by BBC WMV

White Boy Ruin - Mindfucked by BBC WMV

Clips4sale 1 year ago

Sexy TS Succubus Demands Your Cum JOI - HD wmv

HD 0:30 / 15:35

Sexy TS Succubus Demands Your Cum JOI - HD wmv

Clips4sale 3 years ago

sissy gooner therapy-fantasy - cock sucking practice (part 2)

56% HD 0:11 / 31:38

sissy gooner therapy-fantasy - cock sucking practice (part 2)

Clips4sale 2 years ago

Accept it Sissy Encouragement Clip

Accept it Sissy Encouragement Clip

Clips4sale 2 years ago

piss and prolapse: cam crest s dirty shower session

piss and prolapse: cam crest s dirty shower session

AnalVids 2 weeks ago

Submit Sissy Boy

Submit Sissy Boy

Clips4sale 1 year ago

I Know Your Secret (Custom Clip)

I Know Your Secret (Custom Clip)

Clips4sale 1 year ago

Slut training blow job Encouraging PT1 - Real time session recording 480p

Slut training blow job Encouraging PT1 - Real time session recording 480p

Clips4sale 2 years ago

accepting your pride

accepting your pride

Clips4sale 2 weeks ago

GLORY HOLE WHORE 2 *HD 720*

HD 0:35 / 12:45

GLORY HOLE WHORE 2 *HD 720*

Clips4sale 2 years ago

Z To The ZZZ Cup

Z To The ZZZ Cup

Clips4sale 2 years ago

Faggot For Booty

Faggot For Booty

Clips4sale 2 years ago

DENIED MY SISSY COCK!

DENIED MY SISSY COCK!

Clips4sale 1 month ago

My Sissy Best Friend

My Sissy Best Friend

Clips4sale 2 years ago

GLORYHOLE CONFESSIONS

GLORYHOLE CONFESSIONS

Clips4sale 2 years ago

Tasks From Us Cuckolding

HD 0:25 / 11:23

Tasks From Us Cuckolding

Clips4sale 3 years ago

Suck My Cock Lover

Suck My Cock Lover

Clips4sale 1 year ago

Bros Switch: Jaq Quicksilver converts you to a cocksucker - POV flip fuck roleplay - 1080p

HD 0:29 / 13:17

Bros Switch: Jaq Quicksilver converts you to a cocksucker - POV flip fuck roleplay - 1080p

Clips4sale 2 years ago

secret sissy escalation encouragement (1080 WMV)

HD 0:30 / 12:57

secret sissy escalation encouragement (1080 WMV)

Clips4sale 1 year ago

Taking it to the Next Level 720p wmv

55% HD 0:30 / 7:15

Taking it to the Next Level 720p wmv

Clips4sale 1 year ago

Interracial BBC Cum eating cuckold Sissy BBC encouraged bisexual cock sucking creampie eating strapon fucking with Leya Falcon and her sissy slave in chastity 1

Interracial BBC Cum eating cuckold Sissy BBC encouraged bisexual cock sucking creampie eating strapon fucking with Leya Falcon and her sissy slave in chastity 1

Clips4sale 3 years ago

BISEXUAL ENCOURAGEMENT BONDAGE It’s no longer a performance—it’s submission Two big-cocked subs in spit and lust, driven to the brink by ruthless, whispered encouragement and the overwhelming

HD 0:20 / 10:03

BISEXUAL ENCOURAGEMENT BONDAGE It’s no longer a performance—it’s submission Two big-cocked subs in spit and lust, driven to the brink by ruthless, whispered encouragement and the overwhelming

Clips4sale 2 months ago

Locked, Loaded & Ready to be Fucked (4K)

45% 4K 0:18 / 20:01

Locked, Loaded & Ready to be Fucked (4K)

Clips4sale 2 years ago

Slavena ENCOURAGEMENT RIMMING shemale Lusinta

62% 4K 0:11 / 5:58

Slavena ENCOURAGEMENT RIMMING shemale Lusinta

Clips4sale 3 years ago

Go Gay For My Girl-Cock (HD MP4)

4K 0:32 / 15:55

Go Gay For My Girl-Cock (HD MP4)

Clips4sale 4 months ago

Making The Gimp Gag [Bisexual Slave Training]

Making The Gimp Gag [Bisexual Slave Training]

Clips4sale 1 year ago

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu MOBILE

4K 0:20 / 12:03

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu MOBILE

Clips4sale 6 months ago

Sissy cock sucking competition - Miss Honour May - MP4 SD

Premium HD 8:25

Sissy cock sucking competition - Miss Honour May - MP4 SD

Clips4sale 3 years ago

You will goon for dick ONLY

You will goon for dick ONLY

C4S 1 month ago

Your Wife Wants To Fuck Other Men ASMR 18 minute Audio Cuckold Cuck

Premium HD 18:46

Your Wife Wants To Fuck Other Men ASMR 18 minute Audio Cuckold Cuck

Clips4sale 2 months ago

Bad Pup! Jaq Learns to Obey with Fxck Buck - leashes, electro play, and kinky toys - 1080p

Bad Pup! Jaq Learns to Obey with Fxck Buck - leashes, electro play, and kinky toys - 1080p

Clips4sale 1 year ago

Juwanna Man

Clips4sale 1 year ago

STROKE FOR DICK FAGGOT

60% 4K 0:25 / 8:55

STROKE FOR DICK FAGGOT

Clips4sale 2 years ago

2550 JESS ROYAn fuck draw by ESTELLE and AARON

Premium HD 26:08

2550 JESS ROYAn fuck draw by ESTELLE and AARON

xnxxGold 11 months ago

Futa Steals Wife and Fucks You

HD 0:22 / 11:30

Futa Steals Wife and Fucks You

Clips4sale 1 day ago

Witch Turns You Into A Sissy Maid To Pay Off Your Debt

Witch Turns You Into A Sissy Maid To Pay Off Your Debt

Clips4sale 1 year ago

Coaxed bi Cock 720

HD 0:46 / 12:11

Coaxed bi Cock 720

Clips4sale 4 months ago

Addicted To My Pantyhose Feet

Addicted To My Pantyhose Feet

Clips4sale 7 months ago

You Are GAY for Big Balls

Premium HD 7:38

You Are GAY for Big Balls

Clips4sale 1 year ago

Part 2 - Ava's Wet Dream Cum True [4K] (Lesbian, Strap On) | Lady Vi, Goddess Lilith and Ava Venom

58% 4K 0:29 / 24:28

Part 2 - Ava's Wet Dream Cum True [4K] (Lesbian, Strap On) | Lady Vi, Goddess Lilith and Ava Venom

Clips4sale 5 months ago

Obedient Crossdresser Sissy Slut For Blonde Princess June 2025

Obedient Crossdresser Sissy Slut For Blonde Princess June 2025

Clips4sale 2 weeks ago

Sissy Store Sales Girl

Sissy Store Sales Girl

Clips4sale 8 months ago

This Video is a Trap

4K 0:30 / 10:17

This Video is a Trap

Clips4sale 3 years ago

Sissy Used Bi Santa

55% 0:30 / 10:13

Sissy Used Bi Santa

Clips4sale 7 months ago

Pussy Free Sissy Pillow Humping JOI

56% HD 0:21 / 10:14

Pussy Free Sissy Pillow Humping JOI

Clips4sale 1 year ago

THE GAY AWAKENING 2 PODCAST: EPISODE #27: SISSY SLUT SCOTTY UPDATE

4K 0:25 / 12:48

THE GAY AWAKENING 2 PODCAST: EPISODE #27: SISSY SLUT SCOTTY UPDATE

Clips4sale 1 year ago

You're Bullied, He's Rewarded (1080-HD)

HD 0:06 / 10:03

You're Bullied, He's Rewarded (1080-HD)

Clips4sale 4 years ago

You will Goon for DICK only.

66% HD 0:10 / 13:40

You will Goon for DICK only.

LoyalFans 1 month ago

Marry My Pantyhose

HD 0:09 / 16:16

Marry My Pantyhose

Clips4sale 3 years ago

ForXed bi first experience PT2 - being our slut 480p

ForXed bi first experience PT2 - being our slut 480p

Clips4sale 3 years ago

Degraded for Wanting to be a Diaper Girl

65% HD 0:30 / 11:25

Degraded for Wanting to be a Diaper Girl

Clips4sale 5 months ago

Slut Training PT2 - lets make use the teeth for a reason! - 480P

Slut Training PT2 - lets make use the teeth for a reason! - 480P

Clips4sale 1 year ago

Extreme Closeup Cumslut Encouragement

Extreme Closeup Cumslut Encouragement

FapHouse 9 months ago

5 Easy Daily Feminization Routines

4K 0:26 / 12:53

5 Easy Daily Feminization Routines

Clips4sale 4 months ago

Sissy Panty Task - Bella Trixxx - Encoraged Crossdressing & Cum Eating Tasks

Sissy Panty Task - Bella Trixxx - Encoraged Crossdressing & Cum Eating Tasks

Clips4sale 7 months ago

Bondage and feet worship (720p)

HD 0:16 / 10:49

Bondage and feet worship (720p)

Clips4sale 3 years ago

THE GAY AWAKENING 2 PODCAST: EPISODE #19: SISSY ERIC

THE GAY AWAKENING 2 PODCAST: EPISODE #19: SISSY ERIC

Clips4sale 2 years ago

Turning You Plump and Slutty Like Me - A gender transformation scene features trans woman, feminization, POV, mtf, and gentle domination - 720 MP4

HD 0:28 / 11:25

Turning You Plump and Slutty Like Me - A gender transformation scene features trans woman, feminization, POV, mtf, and gentle domination - 720 MP4

Clips4sale 2 years ago

Footjob and handjob from two nurses (wmv)

Footjob and handjob from two nurses (wmv)

Clips4sale 2 years ago

Your Skeevy Friend Humiliates You for Being a Virgin and Steals Your Date From You! - SPH, Verbal Humiliation, Virgin Humilation

Your Skeevy Friend Humiliates You for Being a Virgin and Steals Your Date From You! - SPH, Verbal Humiliation, Virgin Humilation

Clips4sale 9 months ago

** Lapdanced By A Hot SHEMALE **

** Lapdanced By A Hot SHEMALE **

Clips4sale 3 days ago

Shemale porn made you GAY!

Shemale porn made you GAY!

XVideosRed 2 years ago

She owns the scene—trans, DOMINATION Her voice coaxes every thrust, every gag, as the two thick, aching cocks collide in a blur of spit, heat, and deep, gasping surrender

HD 0:20 / 10:12

She owns the scene—trans, DOMINATION Her voice coaxes every thrust, every gag, as the two thick, aching cocks collide in a blur of spit, heat, and deep, gasping surrender

Clips4sale 2 months ago

Let's Stay Inside & Suck Cock

Let's Stay Inside & Suck Cock

Clips4sale 1 year ago

piss and prolapse: cam crest s dirty shower session

56% HD 0:27 / 9:01

piss and prolapse: cam crest s dirty shower session

PornBox 2 weeks ago

Girlcock Addiction

Girlcock Addiction

Clips4sale 9 months ago

Sissy Training Compilation

42% 0:20 / 25:12

Sissy Training Compilation

Clips4sale 2 years ago

The Complete Sissy Slut Experience

The Complete Sissy Slut Experience

Clips4sale 1 year ago

Sadie Holmes - You're A Faggot Humiliation (HD1080 MP4)

HD 0:11 / 12:08

Sadie Holmes - You're A Faggot Humiliation (HD1080 MP4)

Clips4sale 2 years ago

ladyboy Aeing first anal masturbation audition and cum - FULL SCENE HD 12 mins

HD 0:11 / 12:03

ladyboy Aeing first anal masturbation audition and cum - FULL SCENE HD 12 mins

Clips4sale 4 years ago

SLOW DOWN

HD 0:09 / 10:32

Clips4sale 3 years ago

Strip That Manhood

Strip That Manhood

Clips4sale 2 years ago

KAREN KATASTROPHE *HD 1080*

HD 0:35 / 17:56

KAREN KATASTROPHE *HD 1080*

Clips4sale 9 months ago

Jeans Fetish Condom Sissy CEI

Jeans Fetish Condom Sissy CEI

Clips4sale 3 years ago

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4,391 results found

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