Crossdressing (7,072)

Mistress Baton’s Sissy Finishing School Part 1 - The Inspection

HD 0:10 / 13:16

Mistress Baton’s Sissy Finishing School Part 1 - The Inspection

LoyalFans 2 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde Compilation 1

Mistress Pixie Pegging Crossdresser Bailey Wilde Compilation 1

Clips4sale 4 months ago

Rim chair

APClips 1 month ago

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 2

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 2

Clips4sale 4 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde Compilation 17

Mistress Pixie Pegging Crossdresser Bailey Wilde Compilation 17

Clips4sale 4 months ago

Asian Crossdresser Secretary Drools & Cums

Premium 4K 5:54

Asian Crossdresser Secretary Drools & Cums

Clips4sale 2 months ago

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage]

HD 0:30 / 17:10

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage]

Clips4sale 1 month ago

This sissy's toes were made to be used

This sissy's toes were made to be used

XHamster 1 month ago

Hottie Trans Woman Sucking Huge Cock Compilation

Premium 4K 16:36

Hottie Trans Woman Sucking Huge Cock Compilation

Clips4sale 2 months ago

Trans Chloe T Star Anal Blowjob Compilation

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Trans Chloe T Star Anal Blowjob Compilation

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Goth Crossdresser Fucked POV

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Goth Crossdresser Fucked POV

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Trans Swallows and Jerking Off Compilation

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Trans Swallows and Jerking Off Compilation

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Shrink Your Clitty Even More

Premium HD 6:17

Shrink Your Clitty Even More

Clips4sale 1 month ago

Horny sissy plays with themself

4K 0:20 / 17:24

Horny sissy plays with themself

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TS Cassandra LoveLox Takes Jake Grand’s Cock

Premium 4K 43:21

TS Cassandra LoveLox Takes Jake Grand’s Cock

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Trans Cassandra LoveLox Anal Fucked by Jake Grand

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Trans Cassandra LoveLox Anal Fucked by Jake Grand

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Goth Sissy Jade Madison Sucking Dick Compilation 1

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Goth Sissy Jade Madison Sucking Dick Compilation 1

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Pink Haired Trans Woman Fucked and Blowjob Compilation

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Pink Haired Trans Woman Fucked and Blowjob Compilation

Clips4sale 2 months ago

Gorgeous Goth Sissy Jade Madison Anal Vertical Compilation

Premium 4K 13:52

Gorgeous Goth Sissy Jade Madison Anal Vertical Compilation

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Crossdresser and Trans Woman Using Fucking Machine - Compilation 8

HD 0:10 / 26:06

Crossdresser and Trans Woman Using Fucking Machine - Compilation 8

LoyalFans 1 month ago

Sissy Daisy Sucking and Getting Fucked - Compilation 2

HD 0:10 / 29:54

Sissy Daisy Sucking and Getting Fucked - Compilation 2

LoyalFans 1 month ago

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 11

HD 0:10 / 20:10

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 11

LoyalFans 1 month ago

REALLY HOT Trans Woman Riding Strap On *EXCLUSIVE*

REALLY HOT Trans Woman Riding Strap On *EXCLUSIVE*

LoyalFans 1 month ago

Sissy BDSM Dominating Petite Trans Woman - Compilation 6

HD 0:10 / 24:04

Sissy BDSM Dominating Petite Trans Woman - Compilation 6

LoyalFans 1 month ago

Sissy Bailey Wilde and Petite Trans Woman - Compilation 3

HD 0:10 / 20:00

Sissy Bailey Wilde and Petite Trans Woman - Compilation 3

LoyalFans 1 month ago

4K - Holy Femboy Cum Cow Vol 2 -The Cum Shower- SECOND CUM MILKING

4K - Holy Femboy Cum Cow Vol 2 -The Cum Shower- SECOND CUM MILKING

Clips4sale 1 month ago

Petite Trans Woman Sucking TS Bailey Wilde's Dick - Compilation 4

HD 0:10 / 20:15

Petite Trans Woman Sucking TS Bailey Wilde's Dick - Compilation 4

LoyalFans 1 month ago

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 4

HD 0:10 / 20:03

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 4

LoyalFans 1 month ago

Fucking Big Ass Sissy in Chastity - Compilation 2

HD 0:10 / 20:07

Fucking Big Ass Sissy in Chastity - Compilation 2

LoyalFans 2 months ago

POUND TOWN - TS Becki Bottomz & Jake Grand

HD 0:10 / 28:04

POUND TOWN - TS Becki Bottomz & Jake Grand

LoyalFans 2 months ago

Down Low Guy Fucks Trans Woman For First Time

HD 0:10 / 18:03

Down Low Guy Fucks Trans Woman For First Time

LoyalFans 2 months ago

Pizza Man Fucking Mature Crossdresser

Premium 4K 28:01

Pizza Man Fucking Mature Crossdresser

Clips4sale 2 months ago

Just me enjoying myself...

Just me enjoying myself...

LoyalFans 2 months ago

Trans Kala Moon Saved & Fucked in Brussels, Belgium *EXCLUSIVE*

HD 0:10 / 12:46

Trans Kala Moon Saved & Fucked in Brussels, Belgium *EXCLUSIVE*

LoyalFans 2 months ago

Fucking Petite Trans - Compilation 17

63% HD 0:10 / 20:04

Fucking Petite Trans - Compilation 17

LoyalFans 2 months ago

Sissy Pegging Feminization SPH Strap-On II Ellie Rowyn

Sissy Pegging Feminization SPH Strap-On II Ellie Rowyn

Clips4sale 7 months ago

Fucking Petite Trans - Compilation 3

HD 0:10 / 20:05

Fucking Petite Trans - Compilation 3

LoyalFans 2 months ago

Crossdresser BDSM Dominating Petite Trans Teen Compilation 3

Crossdresser BDSM Dominating Petite Trans Teen Compilation 3

Clips4sale 4 months ago

femboy luigi caught jorkin & tied up by bowser!!

Premium HD 8:14

femboy luigi caught jorkin & tied up by bowser!!

Clips4sale 2 months ago

Sissygasm of a Sissy Femboy Slut Riding Toy as a Good Anal Slut

Sissygasm of a Sissy Femboy Slut Riding Toy as a Good Anal Slut

XHamster 3 months ago

4K - Secret Flight Attendant Service: A Realistic ASMR POV

61% 4K 0:11 / 27:54

4K - Secret Flight Attendant Service: A Realistic ASMR POV

Clips4sale 2 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 16

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 16

APClips 2 months ago

Your Sissy Hole

HD 0:21 / 12:04

Your Sissy Hole

IWantClips 2 months ago

Halloween Maid Dress Up And Pegging: Crossdressing Encouragement and POV-Strapon

HD 0:29 / 11:33

Halloween Maid Dress Up And Pegging: Crossdressing Encouragement and POV-Strapon

IWantClips 2 months ago

Bimbo Sniffing Induction - Become My Brainless Fuckdoll

Bimbo Sniffing Induction - Become My Brainless Fuckdoll

Clips4sale 2 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 30

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 30

APClips 2 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

APClips 2 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 38

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 38

APClips 2 months ago

ULTIMATE EXTREME SISSIFICATION - Sissy Training [Sissified] [Sissy Mesmerize] [Sissymaid] [Sissy]

HD 0:30 / 53:58

ULTIMATE EXTREME SISSIFICATION - Sissy Training [Sissified] [Sissy Mesmerize] [Sissymaid] [Sissy]

Clips4sale 1 month ago

Petite Trans Woman Deepthroating Bailey Wilde's Cock and BDSM Compilation

Petite Trans Woman Deepthroating Bailey Wilde's Cock and BDSM Compilation

Clips4sale 4 months ago

Psychic Turns Guy Into Woman For Fortune

Psychic Turns Guy Into Woman For Fortune

Clips4sale 4 months ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde Compilation 1

Petite Trans Woman Fucked and Sucking by Bailey Wilde Compilation 1

Clips4sale 4 months ago

Femboy Bailey Wilde Fucking Huge Ass TS Kelsey Masters Compilation 1

Femboy Bailey Wilde Fucking Huge Ass TS Kelsey Masters Compilation 1

Clips4sale 4 months ago

Struggling with blowing a Yellow Balloon

HD 0:25 / 10:57

Struggling with blowing a Yellow Balloon

Clips4sale 1 month ago

Goth Sissy Jade Madison Sucking Dick Compilation 3

Premium HD 20:03

Goth Sissy Jade Madison Sucking Dick Compilation 3

Clips4sale 2 months ago

4K - Cute Maid Got A Huge Hard Cock Part 1

4K 0:09 / 19:27

4K - Cute Maid Got A Huge Hard Cock Part 1

Clips4sale 5 months ago

HOT Blonde Crossdresser in Las Vegas Jerking Off to Completion

HOT Blonde Crossdresser in Las Vegas Jerking Off to Completion

Clips4sale 5 months ago

Nylon Foot Worship 1044

Nylon Foot Worship 1044

Clips4sale 4 months ago

Prepare For Your New Preference

HD 0:19 / 13:02

Prepare For Your New Preference

IWantClips 1 year ago

Girls found out i stole their clothes and punished me with pegging

Girls found out i stole their clothes and punished me with pegging

Clips4sale 4 months ago

Sissy Goes on All Girls Bachelorette Trip

Sissy Goes on All Girls Bachelorette Trip

Clips4sale 6 months ago

Sissified blowjob training WMV

HD 0:25 / 13:15

Sissified blowjob training WMV

Clips4sale 6 months ago

A Diaper Sissy for the Summer

A Diaper Sissy for the Summer

Clips4sale 6 months ago

Sissy Training - Relax, Its Just A Little Dress Up - Mari Merlowe

Sissy Training - Relax, Its Just A Little Dress Up - Mari Merlowe

Clips4sale 6 months ago

Sissy Encouragement Praise Kink JOI

Sissy Encouragement Praise Kink JOI

IWantClips 3 years ago

You Be The Maid Now

You Be The Maid Now

IWantClips 2 years ago

Nylon Bitchs Ruined Orgasm

Nylon Bitchs Ruined Orgasm

IWantClips 1 year ago

Controlled Burn- Face Only

HD 0:05 / 23:26

Controlled Burn- Face Only

IWantClips 1 year ago

Feminized Sissy Slut

HD 0:20 / 13:27

Feminized Sissy Slut

IWantClips 2 years ago

Pantied And Plugged

HD 0:21 / 11:39

Pantied And Plugged

IWantClips 3 years 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 4 months ago

Me And Wifey Are Cucking You

HD 0:15 / 12:32

Me And Wifey Are Cucking You

IWantClips 6 years ago

Planned Unstoppable Game

HD 0:21 / 12:38

Planned Unstoppable Game

IWantClips 2 years ago

Sissy Mila CBT FULL MP4

Sissy Mila CBT FULL MP4

Clips4sale 4 months ago

No Longer A Man! It's Time To Be A Sissy!!

Premium 4K 9:01

No Longer A Man! It's Time To Be A Sissy!!

Clips4sale 3 months ago

Sissy Release

Premium HD 3:48

Clips4sale 3 months ago

My Slutty Little Lesbian Girlfriend

My Slutty Little Lesbian Girlfriend

Clips4sale 1 year ago

You're Trash

Clips4sale 2 years ago

Penetrate my cream-colored moist poon fuckhole onlyfans alexiakessel1

Penetrate my cream-colored moist poon fuckhole onlyfans alexiakessel1

KeekAss 2 years ago

Straight Fucked Out of You

Straight Fucked Out of You

Clips4sale 2 years ago

Fading Masculinity - With Effects

HD 0:10 / 15:32

Fading Masculinity - With Effects

LoyalFans 2 years ago

Slave girl worship Mistress Milana’s boots

HD 0:10 / 13:54

Slave girl worship Mistress Milana’s boots

LoyalFans 3 months ago

Sissy Girls’ Day After Dark: Pegging Crystal

Premium 4K 10:02

Sissy Girls’ Day After Dark: Pegging Crystal

Clips4sale 2 months ago

Gooning in my pink underwear - 4K UHD MP4

Premium 4K 24:39

Gooning in my pink underwear - 4K UHD MP4

APClips 1 week ago

Watch me tie up and beat this caged sissy's balls before I turn his asshole into a caping pussy

HD 0:25 / 24:41

Watch me tie up and beat this caged sissy's balls before I turn his asshole into a caping pussy

Clips4sale 2 weeks ago

Be A Doll, I Know You Want To

HD 0:25 / 13:35

Be A Doll, I Know You Want To

Clips4sale 3 months ago

Hot Femboy Fucked Mega Compilation

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Hot Femboy Fucked Mega Compilation

Clips4sale 2 months ago

Very Sexy Goth Femboy Jade Madison Anal Compilation 1

Premium 4K 20:02

Very Sexy Goth Femboy Jade Madison Anal Compilation 1

Clips4sale 2 months ago

SPRING FEMDOM PARTY - Hard Ballbusting CBT: 4 Mistresses vs Two Slaves..

SPRING FEMDOM PARTY - Hard Ballbusting CBT: 4 Mistresses vs Two Slaves..

LoyalFans 4 months ago

Straight Guy Pouding Sissy for First Time

Premium 4K 30:52

Straight Guy Pouding Sissy for First Time

Clips4sale 2 months ago

Step-mommies vacation sissy MP4

Step-mommies vacation sissy MP4

Clips4sale 11 months ago

Princess Anitta Pegging

Princess Anitta Pegging

Clips4sale 10 months ago

POV TS Cock Worship Sessions – 3-Video HD Bundle

Premium HD 21:00

POV TS Cock Worship Sessions – 3-Video HD Bundle

Clips4sale 10 months ago

Hot Crossdresser Sucks Blonde Femboy's Huge Dick

Hot Crossdresser Sucks Blonde Femboy's Huge Dick

XHamster 11 months ago

Fabulous Crossdressing Slideshow 10 Minutes Of Sexyness

Fabulous Crossdressing Slideshow 10 Minutes Of Sexyness

AllBoner 2 years ago

1080WMV Sissy Shopping List (Public Humiliation, Sissification, Feminization and Bimbofication)

1080WMV Sissy Shopping List (Public Humiliation, Sissification, Feminization and Bimbofication)

Clips4sale 1 year ago

Young Mistress Foot Worship 1044 wmv

Young Mistress Foot Worship 1044 wmv

Clips4sale 1 year ago

Rubber Slut in Ropes Series Part 3 - Glove Puppet - Gas Masked, Fisted & Shocked to Orgasm

Rubber Slut in Ropes Series Part 3 - Glove Puppet - Gas Masked, Fisted & Shocked to Orgasm

Clips4sale 11 months ago

Creating A New Feminized Doll Stage 1 (WMV)

Creating A New Feminized Doll Stage 1 (WMV)

Clips4sale 1 year ago

SISSY CUCKOLD COCK SUCKING TRAINING - Cuckold Training, Erotic Mind Fuck

SISSY CUCKOLD COCK SUCKING TRAINING - Cuckold Training, Erotic Mind Fuck

Clips4sale 1 year ago

EXTREMELY FAST FEMININE BODY TRANSFORMATION - Feminization Training Mind Fuck [Femme Training] [Female Body] [Feminity] [Femboy] Femme Fatale

EXTREMELY FAST FEMININE BODY TRANSFORMATION - Feminization Training Mind Fuck [Femme Training] [Female Body] [Feminity] [Femboy] Femme Fatale

Clips4sale 1 year ago

BREAKUP OR CUCKOLD: Cuckold Fantasy [Boyfriend] [Girlfriend] [Cuckoldry] [Cuckold Fantasy] [Cuckboy] [Cuck]

BREAKUP OR CUCKOLD: Cuckold Fantasy [Boyfriend] [Girlfriend] [Cuckoldry] [Cuckold Fantasy] [Cuckboy] [Cuck]

Clips4sale 1 year ago

EXTREME CUCKOLDRY - Cuckolding Programming [Cuckold] [Cuck] [Cuckold Training] Cuckolding Mesmerize Audio

EXTREME CUCKOLDRY - Cuckolding Programming [Cuckold] [Cuck] [Cuckold Training] Cuckolding Mesmerize Audio

Clips4sale 1 year ago

COCK DEPENDENT SISSY SLUT MIND FUCK - BIG BLACK COCK, BBC, Sissy Slut Training

COCK DEPENDENT SISSY SLUT MIND FUCK - BIG BLACK COCK, BBC, Sissy Slut Training

Clips4sale 1 year ago

SISSYMAID COMPELLED TO SUCK A BBC BULLS COCK - Femdom Mistress Made You Give Her Bull A Sloppy Blowjob

SISSYMAID COMPELLED TO SUCK A BBC BULLS COCK - Femdom Mistress Made You Give Her Bull A Sloppy Blowjob

Clips4sale 1 year ago

FUCKED BY A NIGHT PARALYSIS FUTA DEMON - Futa Fantasy, Futanari Fantasy, Futanari Cumshots

FUCKED BY A NIGHT PARALYSIS FUTA DEMON - Futa Fantasy, Futanari Fantasy, Futanari Cumshots

Clips4sale 1 year ago

Sissy Sleepover: Part 2

HD 0:21 / 13:47

Sissy Sleepover: Part 2

Clips4sale 3 years ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

LoyalFans 10 months ago

4K - Military Maid s Hard Training

4K 0:12 / 16:24

4K - Military Maid s Hard Training

Clips4sale 9 months ago

Sorority Dress Code Inspection: Bimbo Edition

Sorority Dress Code Inspection: Bimbo Edition

Clips4sale 8 months ago

12 steps to PigmasTox

12 steps to PigmasTox

Clips4sale 8 months ago

Backstage Trampling in Barcelona with Mistress Infinity 👠

HD 0:10 / 12:29

Backstage Trampling in Barcelona with Mistress Infinity 👠

LoyalFans 1 month ago

This shouldn't have been my first Try On for You...

This shouldn't have been my first Try On for You...

APClips 1 month ago

Undressing from a long Day in the office - Pink and Black little number.

Premium HD 10:22

Undressing from a long Day in the office - Pink and Black little number.

C4S 3 weeks ago

Fucking Petite Trans - Compilation 1

HD 0:10 / 20:02

Fucking Petite Trans - Compilation 1

LoyalFans 2 months ago

Hot Crossdresser Dildo Fucked in Kitchen

Hot Crossdresser Dildo Fucked in Kitchen

SpankBang 1 year ago

Mature Crossdresser POV Blowjob

Premium 4K 7:21

Mature Crossdresser POV Blowjob

Clips4sale 2 months ago

HOTTEST Crossdresser Fucked Mega Compilation

Premium 1:59:54

HOTTEST Crossdresser Fucked Mega Compilation

Clips4sale 4 months ago

Girls found out i stole their clothes and punished me with their smelly feet and pegging ?

Premium HD 24:50

Girls found out i stole their clothes and punished me with their smelly feet and pegging ?

Clips4sale 2 months ago

Green Giant Balloon and Black attire

Premium HD 15:55

Green Giant Balloon and Black attire

Clips4sale 2 months ago

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