Crossdress (3,730)

Sissy Training

56% HD 0:10 / 8:03

LoyalFans 1 year ago

Crossdressing Stepsons need to be punished in chastity and humiliated by their Step Mother (short)

Crossdressing Stepsons need to be punished in chastity and humiliated by their Step Mother (short)

Clips4sale 1 year ago

Your Sissy Uniform - Classic French Maid

Your Sissy Uniform - Classic French Maid

Clips4sale 1 year ago

crossdress VID_20240927_235056

crossdress VID_20240927_235056

aShemaleTube 1 year ago

Crossdressing Blonde Babe Pegged

Crossdressing Blonde Babe Pegged

xHamster 1 year ago

Hot Crossdresser in Public Bathroom

Hot Crossdresser in Public Bathroom

xHamster 2 years ago

Don't Pick Up Hitchhikers Written by Victoria Vaughn Narrated by Shayla Aspasia

HD 0:30 / 43:37

Don't Pick Up Hitchhikers Written by Victoria Vaughn Narrated by Shayla Aspasia

Clips4sale 9 months ago

Sissy training task July 25

Sissy training task July 25

Clips4sale 1 year ago

POV: Laying Eggs while You're INSIDE my Ass

POV: Laying Eggs while You're INSIDE my Ass

xHamster 11 months ago

Chairtied Crossdresser Struggles for Freedom 1080p

Chairtied Crossdresser Struggles for Freedom 1080p

Clips4sale 10 months ago

Inspecting The New Sissy Maid (MP4)

69% 0:12 / 12:22

Inspecting The New Sissy Maid (MP4)

Clips4sale 1 year ago

Sex with a stranger.. sissy living

Sex with a stranger.. sissy living

Tranny.one 2 years ago

PART 1 FRENCH MAID CROSSDRESSER SLUT SEXSLAVE SCHOOL LESSON 1 DEEPTHROAT BY FETISHTRANSEXUAL

HD 0:20 / 10:14

PART 1 FRENCH MAID CROSSDRESSER SLUT SEXSLAVE SCHOOL LESSON 1 DEEPTHROAT BY FETISHTRANSEXUAL

Clips4sale 6 months ago

Sissy Sleepover: Part 2

HD 0:21 / 13:47

Sissy Sleepover: Part 2

Clips4sale 2 years ago

Compelled Into Crossdressing - Made To Crossdress By A Bully, Crossdressing Mind Melt

Compelled Into Crossdressing - Made To Crossdress By A Bully, Crossdressing Mind Melt

Clips4sale 1 year ago

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation]

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation]

Clips4sale 1 year ago

Bambis Sissy Transformation

Bambis Sissy Transformation

Clips4sale 3 years ago

Crossdresser eats an orange with her feet - F007

Crossdresser eats an orange with her feet - F007

Clips4sale 2 years ago

crossdress VID_20250418_191950

crossdress VID_20250418_191950

aShemaleTube 3 months ago

Step-mommies vacation sissy MP4

Step-mommies vacation sissy MP4

Clips4sale 7 months ago

Frat Pantyhose Tasks - Kobe Lee Pantyhose Submissive Made To Crossdress and Masturbate in Silky Nylons as Slave Task 1080

HD 0:23 / 13:52

Frat Pantyhose Tasks - Kobe Lee Pantyhose Submissive Made To Crossdress and Masturbate in Silky Nylons as Slave Task 1080

Clips4sale 3 weeks ago

Hotwife dominatrix humiliates fucks chastity cuckold sissy slut! Onlyfans Femdom pegging humiliatrix

Hotwife dominatrix humiliates fucks chastity cuckold sissy slut! Onlyfans Femdom pegging humiliatrix

Pornzona 1 month ago

Girlfriend finds out you're a sissy MP4

Girlfriend finds out you're a sissy MP4

Clips4sale 1 month ago

It's time to get summer ready, sissy! MP4

HD 0:26 / 13:37

It's time to get summer ready, sissy! MP4

Clips4sale 1 week ago

Coaching You into M-to-F Transition

66% 4K 0:29 / 18:54

Coaching You into M-to-F Transition

Clips4sale 1 year ago

Ladysilva crossdress na praia de calcinha que bunda gostosa

Ladysilva crossdress na praia de calcinha que bunda gostosa

Clips4sale 8 months ago

Girlfriend Discovers You re a Crossdresser 4K

Girlfriend Discovers You re a Crossdresser 4K

Clips4sale 8 months ago

Sexy Crossdresser kellycd2022 in sexy black catsuit and heels Clip 1

Sexy Crossdresser kellycd2022 in sexy black catsuit and heels Clip 1

xHamster 10 months ago

crossdress VID_20250418_222921

crossdress VID_20250418_222921

aShemaleTube 1 month ago

Sissified blowjob training WMV

HD 0:25 / 13:15

Sissified blowjob training WMV

Clips4sale 2 months ago

12 steps to PigmasTox

12 steps to PigmasTox

Clips4sale 5 months ago

Pathetic New Hire Sissified by Barbaric Boss! - Part 2

HD 0:30 / 12:54

Pathetic New Hire Sissified by Barbaric Boss! - Part 2

Clips4sale 6 months ago

Anal Toys with Creampie Needy Girl Overdose Shemale Cosplay Clip 2

Anal Toys with Creampie Needy Girl Overdose Shemale Cosplay Clip 2

xHamster 6 months ago

Outlaw in: Bound Shoeplay 1080p

Outlaw in: Bound Shoeplay 1080p

Clips4sale 1 year ago

Change Your Wardrobe - Encouraged Bi

Change Your Wardrobe - Encouraged Bi

Clips4sale 3 years ago

Toe Tongue Bath 4 mp4

Toe Tongue Bath 4 mp4

Clips4sale 2 years ago

How To Be A Sissy Slut

How To Be A Sissy Slut

Clips4sale 2 years ago

EMBRACE YOUR FEMININE ENERGY MIND FUCK - Feminization Beta [En Femme] [Femme Training] [Feminine Energy] [Feminine Mesmerize] [FemBoy] [Female Energy]

EMBRACE YOUR FEMININE ENERGY MIND FUCK - Feminization Beta [En Femme] [Femme Training] [Feminine Energy] [Feminine Mesmerize] [FemBoy] [Female Energy]

Clips4sale 1 year ago

crossdress VID_20250213_222730

crossdress VID_20250213_222730

aShemaleTube 6 months ago

Sissy Lingerie Training

HD 0:10 / 13:04

Sissy Lingerie Training

LoyalFans 6 months ago

crossdress VID_20250226_201931

crossdress VID_20250226_201931

aShemaleTube 5 months ago

Sissy gets snow bunny training from step-sis MP4

HD 0:27 / 16:01

Sissy gets snow bunny training from step-sis MP4

Clips4sale 5 months ago

Cock Blowjob Atago Cosplay CD shemale 20 (re-upload) Clip 1

Cock Blowjob Atago Cosplay CD shemale 20 (re-upload) Clip 1

xHamster 6 months ago

Creampie with Choten-chan Shemale Cosplayer Clip 1

Creampie with Choten-chan Shemale Cosplayer Clip 1

xHamster 6 months ago

Ladysilva crossdress big ass in public 04

Ladysilva crossdress big ass in public 04

Clips4sale 5 months ago

Frilly Prissy Sissy Maid Shelby Alternate Trailer

Frilly Prissy Sissy Maid Shelby Alternate Trailer

xHamster 4 months ago

Bum Bum Lust Shakes My Soul

Bum Bum Lust Shakes My Soul

FapHouse 4 months 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

Glamour Girls Houseslave 51 wmv

Glamour Girls Houseslave 51 wmv

Clips4sale 7 months ago

crossdress VID_20250213_212135

crossdress VID_20250213_212135

aShemaleTube 6 months ago

Sissy Maid Training With Zara Durose Stage 1 (WMV)

Sissy Maid Training With Zara Durose Stage 1 (WMV)

Clips4sale 6 months ago

POV Fuck Cute Shemale Cosplay "Needy Girl Overdose" 10 Clip 1

POV Fuck Cute Shemale Cosplay "Needy Girl Overdose" 10 Clip 1

xHamster 6 months ago

Cock Blowjob Atago Cosplay CD shemale 20 (re-upload) Clip 2

Cock Blowjob Atago Cosplay CD shemale 20 (re-upload) Clip 2

xHamster 6 months ago

Milking Dick Hololive Gawr Gura Cosplay Clip 1

Milking Dick Hololive Gawr Gura Cosplay Clip 1

xHamster 6 months ago

FGO Shielder (Mashu) Japanese Shemale Cosplay 12 Clip 1

FGO Shielder (Mashu) Japanese Shemale Cosplay 12 Clip 1

xHamster 6 months ago

crossdress VID_20250418_193917

crossdress VID_20250418_193917

aShemaleTube 2 months ago

Sissy gets snow bunny training from step-sis WMV

HD 0:27 / 16:01

Sissy gets snow bunny training from step-sis WMV

Clips4sale 5 months ago

crossdress VID_20250220_220537

crossdress VID_20250220_220537

aShemaleTube 5 months ago

Lola femboy Footjob 2 - F008

Lola femboy Footjob 2 - F008

Clips4sale 2 years ago

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation] Mind Fuck

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation] Mind Fuck

Clips4sale 1 year ago

Four Said Feminization (SD MP4)

57% 4K 0:30 / 15:34

Four Said Feminization (SD MP4)

Clips4sale 2 years ago

Panty bitch part 13 RELAPSE with MistressVictoria (EROTIC AUDIO MP3) (SISSY TRAINING) (SHOPPING) (PANTY FETISH)

Panty bitch part 13 RELAPSE with MistressVictoria (EROTIC AUDIO MP3) (SISSY TRAINING) (SHOPPING) (PANTY FETISH)

Clips4sale 1 year ago

crossdress VID_20250302_234457

crossdress VID_20250302_234457

aShemaleTube 4 months ago

Sissy bimbo clinic part 2 - Slut training aftercare

Sissy bimbo clinic part 2 - Slut training aftercare

Clips4sale 3 years ago

Making Yard Man into a Sissy Slave Part 1 m4v

Making Yard Man into a Sissy Slave Part 1 m4v

Clips4sale 2 years ago

Christmas Sissy

Christmas Sissy

Clips4sale 3 years ago

Female Only Office

Female Only Office

Clips4sale 3 years ago

Chastity Sissy Slut Training

HD 0:16 / 21:25

Chastity Sissy Slut Training

Clips4sale 1 year ago

crossdress VID_20240921_032233

crossdress VID_20240921_032233

aShemaleTube 1 year ago

crossdress VID_20240920_233311

crossdress VID_20240920_233311

aShemaleTube 1 year ago

Chastity sissy in pink satin dress gets humiliated by Mistress Nikki Whiplash: made to lapdance, suck a strap on and toy her sissy pussy! WL1750

Chastity sissy in pink satin dress gets humiliated by Mistress Nikki Whiplash: made to lapdance, suck a strap on and toy her sissy pussy! WL1750

Clips4sale 1 year ago

All Dressed Up and Nowhere to Go But Down

All Dressed Up and Nowhere to Go But Down

Clips4sale 1 year ago

Breath In Sissy

Breath In Sissy

Clips4sale 2 years ago

She wants you to crossdress POV

She wants you to crossdress POV

Clips4sale 1 year ago

Blonde Crossdresser Jerking Off

Blonde Crossdresser Jerking Off

xHamster 5 years ago

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 5

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 5

xHamster 2 months ago

Don't Pick Up Hitchhikers Part 3 written by feminization author Kylie Gable Narrated by Shayla Aspsia

HD 0:30 / 41:28

Don't Pick Up Hitchhikers Part 3 written by feminization author Kylie Gable Narrated by Shayla Aspsia

Clips4sale 4 months ago

Sweet Lovelish Kisses Dance with Fire

Sweet Lovelish Kisses Dance with Fire

FapHouse 4 months ago

Sweet Zittish Fire Melts My Core

Sweet Zittish Fire Melts My Core

FapHouse 4 months ago

Sissy Ride Time

HD 0:27 / 14:29

Sissy Ride Time

Clips4sale 4 years ago

Made to wear panties by Strict Lady!

HD 0:11 / 10:11

Made to wear panties by Strict Lady!

Clips4sale 4 years ago

SISSY FOR SLYYY & RENNADEL

Premium HD 8:32

SISSY FOR SLYYY & RENNADEL

Clips4sale 4 years ago

Heteroflexible K solo V68: thin fit muscular hung older twunk jerking to porn on laptop

Heteroflexible K solo V68: thin fit muscular hung older twunk jerking to porn on laptop

Clips4sale 3 years ago

Heteroflexible K crossdressing 97: slender fit older hung transvestite new lingerie panty and bra

Heteroflexible K crossdressing 97: slender fit older hung transvestite new lingerie panty and bra

Clips4sale 3 years ago

scar fetish - second post surgery masturbation withOUT bandages

scar fetish - second post surgery masturbation withOUT bandages

Clips4sale 3 years ago

Wear Lingerie To Class For Your College GF: Sisification & Role Play

Wear Lingerie To Class For Your College GF: Sisification & Role Play

Clips4sale 3 years ago

Blocking Falling Dildo From Sexy Ass

Blocking Falling Dildo From Sexy Ass

xHamster 3 years ago

Ahoy! Caress (and lick dick) Hololive Houshou Marine

Ahoy! Caress (and lick dick) Hololive Houshou Marine

xHamster 3 years ago

My Gothic Doll

Clips4sale 3 years ago

Cowgirl Hentai Asian Femboy Rizu-kyun Cosplay

Cowgirl Hentai Asian Femboy Rizu-kyun Cosplay

xHamster 3 years ago

Sissy's Full Week Caged and Pantied

Sissy's Full Week Caged and Pantied

Clips4sale 3 years ago

Trading Sexes

Clips4sale 3 years ago

Doggie style

Clips4sale 1 year ago

Self Stroke 4 (Chicky) - S036

HD 0:10 / 15:46

Self Stroke 4 (Chicky) - S036

Clips4sale 1 year ago

Blowupguy & The Skipper Toy

Blowupguy & The Skipper Toy

Clips4sale 1 year ago

Sissified prom date

45% 0:30 / 10:27

Sissified prom date

Clips4sale 1 year ago

crossdress VID_20241008_234230

crossdress VID_20241008_234230

aShemaleTube 1 year ago

The Rainbow Sucker

61% 0:30 / 15:24

The Rainbow Sucker

Clips4sale 1 year ago

Part 2 Sissy Slave training : When I see a slave who belonged to me after 6 months without any news : Mistress Julia Femdom video 101

HD 0:10 / 17:01

Part 2 Sissy Slave training : When I see a slave who belonged to me after 6 months without any news : Mistress Julia Femdom video 101

LoyalFans 2 years ago

A Sissy for Sissy 2

A Sissy for Sissy 2

Clips4sale 2 years ago

Lola Crossdresser Deepthroating White 8 Inch - G008

Lola Crossdresser Deepthroating White 8 Inch - G008

Clips4sale 2 years ago

Dave Blowjob 2 - G021

HD 0:10 / 16:43

Dave Blowjob 2 - G021

Clips4sale 2 years ago

I always wanted a girl MP4720

57% 0:31 / 11:40

I always wanted a girl MP4720

Clips4sale 2 years ago

crossdress VID_20241209_164310

crossdress VID_20241209_164310

aShemaleTube 11 months ago

crossdress VID_20241209_203734

crossdress VID_20241209_203734

aShemaleTube 10 months ago

Roommate Caught You in Their Closet

55% 0:11 / 3:52

Roommate Caught You in Their Closet

Clips4sale 1 year ago

How To Crossdress Like A Real Whore

How To Crossdress Like A Real Whore

Clips4sale 1 year ago

You Soft Sissy Bi Bitch!

You Soft Sissy Bi Bitch!

Clips4sale 1 year ago

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Clips4sale 1 year ago

crossdress VID_20241120_232508

crossdress VID_20241120_232508

aShemaleTube 11 months ago

Sissy Claire Masturbation with Chastity Belt and Garter (Preview)

Sissy Claire Masturbation with Chastity Belt and Garter (Preview)

xHamster 11 months ago

crossdress VID_20241209_192955

crossdress VID_20241209_192955

aShemaleTube 10 months ago

Crossdresser Girly-Girl Plumbed

Crossdresser Girly-Girl Plumbed

TrannyGem 10 months ago

Crossdresser Bailey Wilde Fucked by Sex Machine

Crossdresser Bailey Wilde Fucked by Sex Machine

xHamster 11 months ago

Bunny Galore 4

Clips4sale 11 months ago

Messy Cross Dress Shopping Trip Sex V2

69% 0:39 / 39:10

Messy Cross Dress Shopping Trip Sex V2

Clips4sale 11 months ago

crossdress VID_20241120_234853

crossdress VID_20241120_234853

aShemaleTube 11 months ago

crossdress VID_20241209_182442

crossdress VID_20241209_182442

aShemaleTube 11 months ago

COVERT & REAL Transgender Lesbo Duo HUMID Assfucking Lovemaking - CASSIE SQUEALS

COVERT & REAL Transgender Lesbo Duo HUMID Assfucking Lovemaking - CASSIE SQUEALS

TrannyGem 11 months ago

Little Silky, Sissy Whore

Little Silky, Sissy Whore

Clips4sale 1 year ago

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