Crossdressing (5,754)

More Than a Sissy Fantasy

More Than a Sissy Fantasy

Clips4sale 2 years ago

Nothing Quite Like Cock

Nothing Quite Like Cock

Clips4sale 2 years ago

Dancing CD Mindfuck PMV

Dancing CD Mindfuck PMV

Clips4sale 2 years ago

SUPER SEXY Blonde Crossdresser Jerking Off

SUPER SEXY Blonde Crossdresser Jerking Off

xHamster 2 years ago

Layered SFX Sissy Crossdressing Video

Layered SFX Sissy Crossdressing Video

Clips4sale 3 years ago

Sexy Mexican Crossdresser Luna Sol Sucking Huge Cock

Sexy Mexican Crossdresser Luna Sol Sucking Huge Cock

xHamster 2 years ago

TRANSFORMATION TIME

HD 0:10 / 22:33

TRANSFORMATION TIME

LoyalFans 4 years ago

12 DAYS OF GAY-MAS! DAY 5

HD 0:10 / 10:34

12 DAYS OF GAY-MAS! DAY 5

LoyalFans 3 years ago

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KeekAss 2 years ago

Sissy Solo CD Compilation

Sissy Solo CD Compilation

Clips4sale 2 years ago

Total Sissy Slut

Total Sissy Slut

Clips4sale 2 years ago

Dominatrix Makes Roommate Wear Sissy Dress

Dominatrix Makes Roommate Wear Sissy Dress

xHamster 2 years ago

Heteroflexible K solo V53: thin fit muscular hung older twunk uninhibited solo fun

Heteroflexible K solo V53: thin fit muscular hung older twunk uninhibited solo fun

Clips4sale 4 years ago

Whispers Late Night At The Office: Risky JOI, Crossdressing & Cum Eating Countdown

HD 0:29 / 15:52

Whispers Late Night At The Office: Risky JOI, Crossdressing & Cum Eating Countdown

Clips4sale 4 years ago

vein fetish 2 - arms, stomach and cock

vein fetish 2 - arms, stomach and cock

Clips4sale 3 years ago

Heteroflexible K solo V112: thin fit muscular hung older twunk hairy nether region

Heteroflexible K solo V112: thin fit muscular hung older twunk hairy nether region

Clips4sale 3 years ago

Heteroflexible K solo V137: thin slim fit muscular vascular hung older exercise ball ab flexing and masturbation

Heteroflexible K solo V137: thin slim fit muscular vascular hung older exercise ball ab flexing and masturbation

Clips4sale 3 years ago

Heteroflexible K solo V179: thin slim fit muscular vascular hung older uninhibited exhibitionist

Heteroflexible K solo V179: thin slim fit muscular vascular hung older uninhibited exhibitionist

Clips4sale 3 years ago

Just Another Sunday Cowboy Breakfast with @KAROLDIESEL, OnlyFans Flick Domina

Just Another Sunday Cowboy Breakfast with @KAROLDIESEL, OnlyFans Flick Domina

KeekAss 2 years ago

Get Fucked Faggot JOI Cum Countdown

Get Fucked Faggot JOI Cum Countdown

Clips4sale 2 years ago

Solo Man CD MindFuck Comp

Solo Man CD MindFuck Comp

Clips4sale 2 years ago

Hot Blonde Crossdresser Jerks Off in Car

Hot Blonde Crossdresser Jerks Off in Car

xHamster 2 years ago

Loser Faggot Pump JOI Cum Countdown

Loser Faggot Pump JOI Cum Countdown

Clips4sale 2 years ago

Sissy Valentines Day Challenge

HD 0:23 / 10:04

Sissy Valentines Day Challenge

Clips4sale 2 years ago

Dress Up Dealer

Dress Up Dealer

LoyalFans 3 years ago

Sissy Conditioning: Class 8

Sissy Conditioning: Class 8

LoyalFans 3 years ago

STROKE TO BULGES

57% HD 0:10 / 9:50

STROKE TO BULGES

LoyalFans 3 years ago

ELLIE'S SISSY TRAINING 4 720P

ELLIE'S SISSY TRAINING 4 720P

LoyalFans 2 years ago

FEMDOM HOTWIFE TRANSFORMED YOU INTO A CUCKOLD SLAVE - Cuckold Slave Fantasy Training BETA Mesmerize

FEMDOM HOTWIFE TRANSFORMED YOU INTO A CUCKOLD SLAVE - Cuckold Slave Fantasy Training BETA Mesmerize

Clips4sale 1 year ago

Intro To Sissification 2 - Like A Girl

Intro To Sissification 2 - Like A Girl

Clips4sale 2 years ago

Sexy Blonde Sissy Bailey Wilde Fucked While Stroking Cock

Sexy Blonde Sissy Bailey Wilde Fucked While Stroking Cock

xHamster 1 year ago

POV Cumming

aShemaleTube 6 years ago

Lets Finish Your Destruction

64% HD 0:10 / 7:29

Lets Finish Your Destruction

LoyalFans 1 year ago

Onlyfans @TsJadePerfume - Round Ladyboy Use a Good-Sized Iron Sound

Onlyfans @TsJadePerfume - Round Ladyboy Use a Good-Sized Iron Sound

TrannyGem 1 year ago

Crossdressing Blonde Babe Pegged

Crossdressing Blonde Babe Pegged

xHamster 1 year ago

Colorful and Captivating: A Compilation of Crossdressing Magic!

Colorful and Captivating: A Compilation of Crossdressing Magic!

xHamster 1 year ago

Cum eating Crossdresser Eating Alpha Cum, Crossdressing and made to do humiliating tasks for her pleasure!

Cum eating Crossdresser Eating Alpha Cum, Crossdressing and made to do humiliating tasks for her pleasure!

Clips4sale 1 year ago

Drooling, bound, caged and gagged sissy ridding dildo

HD 0:30 / 25:27

Drooling, bound, caged and gagged sissy ridding dildo

Clips4sale 1 year ago

Special Effects CD PMV

Special Effects CD PMV

Clips4sale 2 years ago

Fuck Machine Fucks Crossdresser Bailey Wilde Doggystyle

Fuck Machine Fucks Crossdresser Bailey Wilde Doggystyle

xHamster 1 year ago

Cucked with My Ass: Part IV

55% HD 0:15 / 8:42

Cucked with My Ass: Part IV

Clips4sale 1 year ago

Femboy SFX PMV

Clips4sale 2 years ago

4K - Femcock vs Vibrator Round 5

4K 0:20 / 17:53

4K - Femcock vs Vibrator Round 5

Clips4sale 1 year ago

Sissy Bride Edging in Panties Challenge

I'm going to dress you up like a slutty sissy Bride with a butt plug! You will edge in your panties for me a

HD 0:10 / 10:48

Sissy Bride Edging in Panties Challenge I'm going to dress you up like a slutty sissy Bride with a butt plug! You will edge in your panties for me a

LoyalFans 1 year ago

Anal with Dildo 4 (Cat Socks) - S023

HD 0:10 / 14:39

Anal with Dildo 4 (Cat Socks) - S023

Clips4sale 1 year ago

The New white loser Policy

66% 0:21 / 5:25

The New white loser Policy

Clips4sale 1 year ago

Big Dick blasts huge cumshot all over your face

Big Dick blasts huge cumshot all over your face

xHamster 2 years ago

Cross-dressing PMV

Cross-dressing PMV

Clips4sale 2 years ago

Hot Wife Cuckoldress Train You To Suck A Cock - Erotic Audio Mind Fuck

Hot Wife Cuckoldress Train You To Suck A Cock - Erotic Audio Mind Fuck

Clips4sale 1 year ago

Sissy trains her throat on my strap-on!

63% 0:18 / 6:20

Sissy trains her throat on my strap-on!

Clips4sale 1 year ago

Trans Lady Magical Melon

Trans Lady Magical Melon

TrannyGem 1 year ago

4K - Lusty Shower Vol 18 {TEARING FEST}

4K 0:12 / 31:01

4K - Lusty Shower Vol 18 {TEARING FEST}

Clips4sale 1 year ago

4K - Glasses Girl # 7

68% 4K 0:11 / 9:43

4K - Glasses Girl # 7

Clips4sale 1 year ago

[Erotic Audio] Twilight Blush Ch II

HD 0:30 / 15:06

[Erotic Audio] Twilight Blush Ch II

Clips4sale 1 year ago

SLUT TRAINING. BIG TOYS STRETCH BISEXUAL ANAL. DOMINATRIX ANNETTE PEGGING BOYS ASS

Premium HD 8:11

SLUT TRAINING. BIG TOYS STRETCH BISEXUAL ANAL. DOMINATRIX ANNETTE PEGGING BOYS ASS

Sheer 3 years ago

FEMDOM. HARD DESTROYING HIS ASS. ROUGH PEGGING AMATEUR CHASTITY BELT FEMDOM FISTING

Premium HD 9:22

FEMDOM. HARD DESTROYING HIS ASS. ROUGH PEGGING AMATEUR CHASTITY BELT FEMDOM FISTING

Sheer 3 years ago

Gooning For Crossdressers, Bisexual Gooner Porn Addiction

Gooning For Crossdressers, Bisexual Gooner Porn Addiction

Clips4sale 1 year ago

TURNING INTO SISSY A WHORE. YOUR ROLE IS TO FUCK IN ANAL IN THE CHASTITY BELT.

Premium HD 14:49

TURNING INTO SISSY A WHORE. YOUR ROLE IS TO FUCK IN ANAL IN THE CHASTITY BELT.

Sheer 3 years ago

Sexy Crossdresser Kellycd2022 afternoon drive in the sunshine Clip 2

Sexy Crossdresser Kellycd2022 afternoon drive in the sunshine Clip 2

xHamster 1 year ago

Sensual Sissy JOI

59% HD 0:10 / 9:34

Sensual Sissy JOI

LoyalFans 1 year ago

Young Mistress Foot Smelling 1044

Young Mistress Foot Smelling 1044

Clips4sale 1 year ago

Cucked with My Ass: Part IV

Cucked with My Ass: Part IV

LoyalFans 1 year ago

Let's be pretty together with MistressVictoria (SISSY TRAINING) (CROSSDRESSING) (PRINCESS)

HD 0:10 / 10:24

Let's be pretty together with MistressVictoria (SISSY TRAINING) (CROSSDRESSING) (PRINCESS)

LoyalFans 1 year ago

submitted and shown off

submitted and shown off

Clips4sale 1 year ago

Sexy Crossdresser kellycd2022 enjoying an afternoon car ride in my leopard print dress and seamless pantyhose Clip 1

Sexy Crossdresser kellycd2022 enjoying an afternoon car ride in my leopard print dress and seamless pantyhose Clip 1

xHamster 1 year ago

Dick Worship and Crossdressing Encouragement Mind Fuck

Dick Worship and Crossdressing Encouragement Mind Fuck

Clips4sale 2 years ago

Sexy Brunette Crossdresser Sucking Femboy's Huge Cock

Sexy Brunette Crossdresser Sucking Femboy's Huge Cock

xHamster 2 years ago

Hot Blonde Crossdresser has Cock Rubbed by Guy's Feet

Hot Blonde Crossdresser has Cock Rubbed by Guy's Feet

xHamster 2 years ago

Oops Sissy On Blast

Oops Sissy On Blast

LoyalFans 2 years ago

ASMR - Found Your Panties (AUDIO ONLY)

ASMR - Found Your Panties (AUDIO ONLY)

LoyalFans 2 years ago

💖🌸April's Sissy Program - VIDEO 4 Blowjob Training 🌸💖

HD 0:10 / 11:14

💖🌸April's Sissy Program - VIDEO 4 Blowjob Training 🌸💖

LoyalFans 2 years ago

Black Lingerie Crossdresser Fucks Black Dress Petite Trans Woman

Black Lingerie Crossdresser Fucks Black Dress Petite Trans Woman

xHamster 1 year ago

MISTRESS NYX - THE CAPRICIOUS WHORE TIED AND SPANKING

MISTRESS NYX - THE CAPRICIOUS WHORE TIED AND SPANKING

Clips4sale 1 year ago

Sissy's Used Gash

61% HD 0:10 / 12:14

Sissy's Used Gash

LoyalFans 1 year ago

Not Cheating if it is Dick

Not Cheating if it is Dick

Clips4sale 2 years ago

SISSY TRANSFORMATION

HD 0:10 / 10:04

SISSY TRANSFORMATION

LoyalFans 2 years ago

Horny Sissy For Halloween - Extended Preview

Horny Sissy For Halloween - Extended Preview

xHamster 2 years ago

Dominatrix Makes Sissy Maid Get Cowgirl Fucked

Dominatrix Makes Sissy Maid Get Cowgirl Fucked

xHamster 2 years ago

Caged - Pantied - Plugged

HD 0:15 / 11:59

Caged - Pantied - Plugged

Clips4sale 2 years ago

Dildo Masturbation 3 - S025

HD 0:10 / 15:50

Dildo Masturbation 3 - S025

Clips4sale 1 year ago

The Sissy Spiral 720MP4

The Sissy Spiral 720MP4

Clips4sale 1 year ago

Sissy Slut gets spanked in chastity

Sissy Slut gets spanked in chastity

LoyalFans 1 year ago

SISSY LOCKTOBER - RELEASE YOUR NEW CLITTY

4K 0:29 / 14:13

SISSY LOCKTOBER - RELEASE YOUR NEW CLITTY

Clips4sale 1 year ago

4K - Santa Femboy Cum Huge to you

4K 0:19 / 26:39

4K - Santa Femboy Cum Huge to you

Clips4sale 1 year ago

She's obedient and loves to suck his cock with devotion, making her master enjoy it

She's obedient and loves to suck his cock with devotion, making her master enjoy it

xHamster 1 year ago

Crossdressing Cheerleader Fucking Crossdresser

Crossdressing Cheerleader Fucking Crossdresser

xHamster 1 year ago

Empress E Academy -Lesson no 4- Embracing your femininity

Empress E Academy -Lesson no 4- Embracing your femininity

LoyalFans 1 year ago

Barbershop - Britni Bomshel

Barbershop - Britni Bomshel

TrannyGem 1 year ago

Crossdresser skirt bulge

Crossdresser skirt bulge

aShemaleTube 1 year ago

Crossdresser skirt bulge in pink

Crossdresser skirt bulge in pink

aShemaleTube 1 year ago

Lola Double Blowjob to Facial Part 2 - G019(2)

HD 0:10 / 26:54

Lola Double Blowjob to Facial Part 2 - G019(2)

Clips4sale 1 year ago

BISEXUAL HUBBY IN CHASTITY BELT AS HE GETS FUCKED BY MISTRESS! STRAPON FEMDOM AMATEUR PORN

Premium HD 8:37

BISEXUAL HUBBY IN CHASTITY BELT AS HE GETS FUCKED BY MISTRESS! STRAPON FEMDOM AMATEUR PORN

Sheer 3 years ago

KEEP YOUR SECRETS CLOSE & YOUR PANTIES CLOSER

KEEP YOUR SECRETS CLOSE & YOUR PANTIES CLOSER

LoyalFans 1 year ago

Latex walking in the park

65% HD 0:11 / 5:41

Latex walking in the park

Clips4sale 1 year ago

Hot Blonde Crossdresser Whipped and Paddled

Hot Blonde Crossdresser Whipped and Paddled

xHamster 1 year ago

Gape My Girl

HD 0:10 / 13:30

LoyalFans 1 year ago

Supergirl and Wonder Woman Pantyhose & Foot Tease (HD1080 WMV)

Supergirl and Wonder Woman Pantyhose & Foot Tease (HD1080 WMV)

Clips4sale 2 years ago

Mistress Marley Paddles Hoodbitch

Mistress Marley Paddles Hoodbitch

Clips4sale 2 years ago

What She Doesn't Know...

What She Doesn't Know...

LoyalFans 2 years ago

Crossdressing Slave Orally and Anally Submitted - Full Version

HD 0:30 / 21:33

Crossdressing Slave Orally and Anally Submitted - Full Version

Clips4sale 1 year ago

Cucked with My Ass: Part III

Cucked with My Ass: Part III

LoyalFans 1 year ago

Sexy Skinny Trans Hands Free Sissygasm & Cumshot After Moaning & Talking Dirty Fucking Huge Dildo

Sexy Skinny Trans Hands Free Sissygasm & Cumshot After Moaning & Talking Dirty Fucking Huge Dildo

Clips4sale 1 year ago

Sissy Wardrobe Obedience

HD 0:10 / 19:38

Sissy Wardrobe Obedience

LoyalFans 6 months ago

Panties Down & Bottoms Out - Mistress Need to Pound Some Boi Pussy

Panties Down & Bottoms Out - Mistress Need to Pound Some Boi Pussy

Clips4sale 3 years ago

THE HOTWIFE, THE BULL, AND THE CUCKOLD MIND FUCK - Erotic Cuckold Training [Cuckold] [Cuck] [Cuckoldry] [Cuckolding] [Bulls]

THE HOTWIFE, THE BULL, AND THE CUCKOLD MIND FUCK - Erotic Cuckold Training [Cuckold] [Cuck] [Cuckoldry] [Cuckolding] [Bulls]

Clips4sale 1 year ago

DIAPERED SISSY REVERSAL - Femdom Mistress Talks You Out Of Sissyhood, ABDL Sissy Mind Fuck

DIAPERED SISSY REVERSAL - Femdom Mistress Talks You Out Of Sissyhood, ABDL Sissy Mind Fuck

Clips4sale 1 year ago

JOI CUM IN CHASTITY SISSY, TEASE AND DENIAL - Compelled Chastity Training, Chastity Keyholder] [Locktober] [Locked In Chastity]

JOI CUM IN CHASTITY SISSY, TEASE AND DENIAL - Compelled Chastity Training, Chastity Keyholder] [Locktober] [Locked In Chastity]

Clips4sale 1 year ago

INTENSE SISSYGASM - Sissy Hands Free Orgasm [Sissification] [HFO] [Sissy Training] Sissy Sluts Mesmerize

INTENSE SISSYGASM - Sissy Hands Free Orgasm [Sissification] [HFO] [Sissy Training] Sissy Sluts Mesmerize

Clips4sale 1 year ago

First Time Anal Experience and Chastity Play : Sissy Gets Hot & Horny with Toys

HD 0:30 / 16:59

First Time Anal Experience and Chastity Play : Sissy Gets Hot & Horny with Toys

Clips4sale 1 year ago

Cute

55% HD 0:10 / 10:17

LoyalFans 6 months ago

Solo Male Visual Effects CD PMV

Solo Male Visual Effects CD PMV

Clips4sale 2 years ago

Extreme Sissy Viper Nasty 60 Cum-blast Fuckfest Part 3

HD 0:30 / 14:45

Extreme Sissy Viper Nasty 60 Cum-blast Fuckfest Part 3

Clips4sale 6 months ago

Crossdressed Sissy Play – Rimjob Before He Rides My Strapon to Explosive Cum

Crossdressed Sissy Play – Rimjob Before He Rides My Strapon to Explosive Cum

Clips4sale 4 months ago

Risk-Free Sissy Dare

HD 0:10 / 16:33

Risk-Free Sissy Dare

LoyalFans 3 months ago

New Year Of Sissy Training - Sissy Tasks, Sissy Affirmations, Crossdressing Encouragement

4K 0:17 / 13:29

New Year Of Sissy Training - Sissy Tasks, Sissy Affirmations, Crossdressing Encouragement

Clips4sale 5 months ago

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 9 Clip 1

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 9 Clip 1

xHamster 5 months ago

You Crave Crossdressing – Legging Worship

You Crave Crossdressing – Legging Worship

LoyalFans 5 months ago

SISSYMAID UNIFORM PROGRAMMING BETA - Sissymaid Training [Sissymaid] [Sissymaid Uniforms] [Sissymaid Outfit]

SISSYMAID UNIFORM PROGRAMMING BETA - Sissymaid Training [Sissymaid] [Sissymaid Uniforms] [Sissymaid Outfit]

Clips4sale 1 year ago

HOT WIFE TAKES CONTROL WITH THE STRAPON - Husband Turned Sissy Mesmerize [Sissy Mind Fuck] [Sissy Training] [Mind Melt]

HOT WIFE TAKES CONTROL WITH THE STRAPON - Husband Turned Sissy Mesmerize [Sissy Mind Fuck] [Sissy Training] [Mind Melt]

Clips4sale 1 year ago

PUPPY PET RUINED ORGASM - PET PLAY II [Puppy] [Pup Play] [Human Pup Fantasy] Mind Fuck

63% 0:30 / 22:42

PUPPY PET RUINED ORGASM - PET PLAY II [Puppy] [Pup Play] [Human Pup Fantasy] Mind Fuck

Clips4sale 1 year ago

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