Crossdressing Compilation Videos (4,639)

Gay & Trans - Ladyboy Tries It with Old Guy for the First Time

55% HD 0:39 / 9:41

Gay & Trans - Ladyboy Tries It with Old Guy for the First Time

FapHouse 5 months ago

More Oil and Posing

More Oil and Posing

xHamster 5 months ago

Crossdresser, Sissy Cums 112 - Self Suck Compilation

Crossdresser, Sissy Cums 112 - Self Suck Compilation

AbTranny 6 years ago

Undressing for You

Undressing for You

xHamster 4 months ago

Fucking Mature Crossdresser and Blowjob - Compilation 6

Fucking Mature Crossdresser and Blowjob - Compilation 6

xHamster 5 months ago

Sissy Handsfree Cum on BBC

Sissy Handsfree Cum on BBC

FapHouse 4 months ago

Compilation of New Outfits

Compilation of New Outfits

xHamster 9 months ago

Petite Sexy Asian French Maid Ladyboy Rozebell Gets Fucked Hard & Sucks Cock Part2

Petite Sexy Asian French Maid Ladyboy Rozebell Gets Fucked Hard & Sucks Cock Part2

xHamster 9 months ago

Mesmeriza

HD 0:39 / 32:06

FapHouse 8 months ago

Panty Tease with Cumshot

Panty Tease with Cumshot

FapHouse 8 months ago

Femboy Cums on Stockings

Femboy Cums on Stockings

FapHouse 8 months ago

Crossdresser Krissy Sweets Sexy Dirty Talk Compilation

Crossdresser Krissy Sweets Sexy Dirty Talk Compilation

FapHouse 8 months ago

French Tannys escort Compilation

French Tannys escort Compilation

AbTranny 7 years ago

Sissy Shelby Kiss's New Year's Resolutions for 2026 Clip 1

Sissy Shelby Kiss's New Year's Resolutions for 2026 Clip 1

xHamster 1 month ago

TS Kandi Sexy Shemale Compilation Pmv

HD 0:39 / 10:45

TS Kandi Sexy Shemale Compilation Pmv

FapHouse 4 months ago

Wet Tan Pantyhose in the Shower

Wet Tan Pantyhose in the Shower

FapHouse 4 months ago

Gay & Trans - Tranny Hooker Is Mercilessly Taken by the Young Craftsman

Gay & Trans - Tranny Hooker Is Mercilessly Taken by the Young Craftsman

xHamster 4 months ago

Fucking Mature Crossdresser and Blowjob - Compilation 10

Fucking Mature Crossdresser and Blowjob - Compilation 10

xHamster 4 months ago

Hot Cum Compilations July 2025 Sissy Femboy Vs Daddy! Exclusive

Hot Cum Compilations July 2025 Sissy Femboy Vs Daddy! Exclusive

xHamster 4 months ago

A Trav Student Masturbates💦12:30 in her Illuminati Fishnet Mini-Skirt and Small Bow Heels. VaneSsaBiTCHx Clip 2

A Trav Student Masturbates💦12:30 in her Illuminati Fishnet Mini-Skirt and Small Bow Heels. VaneSsaBiTCHx Clip 2

xHamster 4 months ago

Must-share moment from "CHAPTER: sit on my COCK whore"

Must-share moment from "CHAPTER: sit on my COCK whore"

xHamster 5 months ago

Must-share moment from "Smooth & Shiny Silk Slides Over Nylon Stockings"

Must-share moment from "Smooth & Shiny Silk Slides Over Nylon Stockings"

xHamster 4 months ago

A Fountain of Cum on a Friend From Huge Cocks, Wash Yourself with Cum!

A Fountain of Cum on a Friend From Huge Cocks, Wash Yourself with Cum!

xHamster 4 months ago

Gay & Trans - Ladyboy Session

Gay & Trans - Ladyboy Session

xHamster 4 months ago

A Trav Student Masturbates💦12:30 in her Illuminati Fishnet Mini-Skirt and Small Bow Heels. VaneSsaBiTCHx Clip 3

A Trav Student Masturbates💦12:30 in her Illuminati Fishnet Mini-Skirt and Small Bow Heels. VaneSsaBiTCHx Clip 3

xHamster 4 months ago

Asian Femboy Lola Bunny Uses a Dildo & a Fuck-machine To Please His Needy Big Ass - Compilation

Asian Femboy Lola Bunny Uses a Dildo & a Fuck-machine To Please His Needy Big Ass - Compilation

XGroovy 1 year ago

Unforgettable moment from "The Best Of A Wanking Sissy"

Unforgettable moment from "The Best Of A Wanking Sissy"

xHamster 6 months ago

Powerful moment from "twink iranian femboy"

Powerful moment from "twink iranian femboy"

xHamster 6 months ago

Fuck in the Ass

Fuck in the Ass

xHamster 4 months ago

Wet Tan Pantyhose in the Shower

Wet Tan Pantyhose in the Shower

xHamster 4 months ago

The Syn Thetic Compilation 1.0 ...

The Syn Thetic Compilation 1.0 ...

KeekAss 3 years ago

Super-Steamy Transgender Princess Cdbobbiejoejoe Slideshow

Super-Steamy Transgender Princess Cdbobbiejoejoe Slideshow

KeekAss 3 years ago

CDAdalyn - Assorted Toy Play Compliation

CDAdalyn - Assorted Toy Play Compliation

xHamster 3 years ago

TOTAL Sissy Mara Jade's Railing Compilation

TOTAL Sissy Mara Jade's Railing Compilation

TrannyGem 3 years ago

Warning : Sissyfication is real - Sissy Joyce's warning

Warning : Sissyfication is real - Sissy Joyce's warning

KeekAss 3 years ago

TRANS and CHICK TORRID POP-SHOTS

TRANS and CHICK TORRID POP-SHOTS

KeekAss 3 years ago

Pic Compilation two

Pic Compilation two

KeekAss 3 years ago

Solo Compilation of a Young French Sissy Femboy - Nolyneoz

Solo Compilation of a Young French Sissy Femboy - Nolyneoz

xHamster 3 years ago

SHE-MALE SOLO MONEY-SHOTS AND BUTTFUCK COMPILATION

SHE-MALE SOLO MONEY-SHOTS AND BUTTFUCK COMPILATION

TrannyGem 3 years ago

I need a Weirdo

I need a Weirdo

KeekAss 3 years ago

Jizzing forearms free-for-all from rigid boinking

Jizzing forearms free-for-all from rigid boinking

TrannyGem 3 years ago

Daddy Search 2024

Daddy Search 2024

xHamster 1 year ago

Luzia_Tv, My Hot Cumshots 2 Compilation

Luzia_Tv, My Hot Cumshots 2 Compilation

xHamster 1 year ago

Mind Fuck Crossdressing Encouragement

Mind Fuck Crossdressing Encouragement

Clips4sale 2 years ago

Deep Assfuck Fake Penis makes Big Jizz Flow

Deep Assfuck Fake Penis makes Big Jizz Flow

KeekAss 4 years ago

Matures do it finer two

Matures do it finer two

KeekAss 4 years ago

Compilation of Suzie 1

Compilation of Suzie 1

TrannyGem 4 years ago

Paulina's Summer of 69 (Anal)

Paulina's Summer of 69 (Anal)

Tranny.one 4 years ago

Transgender Princess jacking her gurl man rod, jizzing and peeing

Transgender Princess jacking her gurl man rod, jizzing and peeing

KeekAss 4 years ago

My Cumming Compilation

My Cumming Compilation

Tranny.one 4 years ago

PMV Sissy Lili anal invasion medley #1- slapping, taunting, oral pleasure, inhale, assfucking

PMV Sissy Lili anal invasion medley #1- slapping, taunting, oral pleasure, inhale, assfucking

KeekAss 3 years ago

Crossdresser Alaina Sanchez May June July August 24'

Crossdresser Alaina Sanchez May June July August 24'

xHamster 1 year ago

Sexy Sissy Lucy Compilation

Premium HD 10:27

Sexy Sissy Lucy Compilation

XVideosRed 5 years ago

Vintage Leasha 2016-2018 X

Vintage Leasha 2016-2018 X

KeekAss 1 year ago

Anal Bareback Fucked Tgirls and Crossdressers

Anal Bareback Fucked Tgirls and Crossdressers

XXXShemalePorn 9 years ago

Many men in sissies moments

Many men in sissies moments

AbTranny 7 years ago

Slut play

aShemaleTube 9 years ago

sissyCD Tonia 2016 oral best of

sissyCD Tonia 2016 oral best of

aShemaleTube 9 years ago

Compilation removing my retro pants and removing my sexy black lace pants to do some stretching and bending with no panties

Compilation removing my retro pants and removing my sexy black lace pants to do some stretching and bending with no panties

xHamster 1 year ago

Femboy Bunny Masturbates to Orgasm

HD 1:01 / 12:04

Femboy Bunny Masturbates to Orgasm

FapHouse 10 months ago

Crossdressers and the Fucking Machine - Compilation 3

HD 1:01 / 20:05

Crossdressers and the Fucking Machine - Compilation 3

FapHouse 10 months ago

Beauty Beyond Boundaries: Celebrating Diversity in Crossdressing!

HD 0:39 / 23:26

Beauty Beyond Boundaries: Celebrating Diversity in Crossdressing!

FapHouse 9 months ago

Crossdressers Fucked by Fucking Machine - Compilation 3

HD 0:39 / 20:07

Crossdressers Fucked by Fucking Machine - Compilation 3

FapHouse 11 months ago

Crossdressing Fem MindFuck B&W

Crossdressing Fem MindFuck B&W

Clips4sale 2 years ago

Horny Nylonjunge Collage in Pantyhose

Horny Nylonjunge Collage in Pantyhose

FapHouse 2 years ago

Hottest Ladyboy Sissy Jizz Compilation

Hottest Ladyboy Sissy Jizz Compilation

KeekAss 2 years ago

SFX Sissy Mind Fuck B&W

SFX Sissy Mind Fuck B&W

Clips4sale 2 years ago

TRANSSEXUAL Willow Hammerz - Jaw-Dropping sissy PMV

TRANSSEXUAL Willow Hammerz - Jaw-Dropping sissy PMV

TrannyGem 3 years ago

Prompt cum shots compilation

Prompt cum shots compilation

KeekAss 2 years ago

Lizzaal compilation

Lizzaal compilation

KeekAss 2 years ago

Amateur Sissy Lingerie Dance pantyhose sexy comp

Amateur Sissy Lingerie Dance pantyhose sexy comp

xHamster 2 years ago

Solo male Panties Compilation

Solo male Panties Compilation

Clips4sale 2 years ago

Don't hurt me

KeekAss 2 years ago

Fire Booty PMV B&W

Fire Booty PMV B&W

Clips4sale 2 years ago

Sissy Cassie's 2022 Greatest of Snapchat Spunk in Web Cam

Sissy Cassie's 2022 Greatest of Snapchat Spunk in Web Cam

KeekAss 2 years ago

Crossdresser Self Facial Compilation

Crossdresser Self Facial Compilation

VivaTube 5 years ago

Solo Man Crossdressing MINDFUCK

Solo Man Crossdressing MINDFUCK

Clips4sale 2 years ago

Captioned CD Encouragement

Captioned CD Encouragement

Clips4sale 2 years ago

Spun Sissy Opening Up in the Snow

Spun Sissy Opening Up in the Snow

KeekAss 2 years ago

crossdresser missionary compilation - part one

crossdresser missionary compilation - part one

VivaTube 5 years ago

Bambi Bella Compilation Vol 1

4K 0:22 / 10:18

Bambi Bella Compilation Vol 1

Clips4sale 2 years ago

Crossdressing Pop Music Video

Crossdressing Pop Music Video

Clips4sale 2 years ago

crossdresser missionary compilation - part two

crossdresser missionary compilation - part two

TubeOn 5 years ago

Crossdresser Self Facial Compilation

Crossdresser Self Facial Compilation

YepTube 5 years ago

Solo Male Fishnet Fetish PMV

Solo Male Fishnet Fetish PMV

Clips4sale 2 years ago

Esta Transgirl llegando para amar tu corazon

Esta Transgirl llegando para amar tu corazon

KeekAss 2 years ago

DeeDeeSlut69 Various Garbs

DeeDeeSlut69 Various Garbs

KeekAss 3 years ago

Trouble Maker

ShemaleSin 3 years ago

Finest sissy mega-bitch cum shot compilation with a pile of fetishes

Finest sissy mega-bitch cum shot compilation with a pile of fetishes

KeekAss 2 years ago

OFF THE HOOK Uber-Cute Crossdresser EXTREME Parts

OFF THE HOOK Uber-Cute Crossdresser EXTREME Parts

KeekAss 2 years ago

little anal session in pinky outfit

little anal session in pinky outfit

xHamster 2 years ago

Selenahot stretching, smacking and dildoing blend

Selenahot stretching, smacking and dildoing blend

KeekAss 2 years ago

Let’s Masturbate Off Together

Let’s Masturbate Off Together

TrannyGem 2 years ago

Hot Femboy Mindfuck

57% 0:57 / 3:26

Hot Femboy Mindfuck

Clips4sale 2 years ago

Special Effects CamBoy Compilation

Special Effects CamBoy Compilation

Clips4sale 2 years ago

Crossdresser Self Facial Compilation

Crossdresser Self Facial Compilation

TubeOn 3 years ago

Sissy crossdressing Husband getting poked by wifey

Sissy crossdressing Husband getting poked by wifey

KeekAss 2 years ago

JISM COMPILATION Lots of jism in nylon stocking

JISM COMPILATION Lots of jism in nylon stocking

KeekAss 2 years ago

Layered Crossdressing Compilation

Layered Crossdressing Compilation

Clips4sale 3 years ago

White Sissy Love Black Cock Collection

White Sissy Love Black Cock Collection

AbTranny 7 years ago

Sissy SFX PMV

Clips4sale 2 years ago

Femboy Cumshot Compilation 1

Femboy Cumshot Compilation 1

UrGayPorn 1 year ago

Fashion Show With Caning And Double Cumshot

Fashion Show With Caning And Double Cumshot

xHamster 1 year ago

Pretty in Pink: Adorable Crossdressing Styles to Swoon Over!

Pretty in Pink: Adorable Crossdressing Styles to Swoon Over!

xHamster 1 year ago

Sissy Male Crossdressing

Sissy Male Crossdressing

Clips4sale 2 years ago

Sissy CD MindFuck B&W

Sissy CD MindFuck B&W

Clips4sale 2 years ago

Torrid compilation of sissy femboy cum shots - Jizm compilation #01

Torrid compilation of sissy femboy cum shots - Jizm compilation #01

KeekAss 2 years ago

Compilation of lil boner femboy

Compilation of lil boner femboy

KeekAss 2 years ago

Dare to be Different: A Crossdresser's Cut-Offs Venture Embrace Your Internal Diva The Hottest Crossdresse

Dare to be Different: A Crossdresser's Cut-Offs Venture Embrace Your Internal Diva The Hottest Crossdresse

TrannyGem 2 years ago

Pretty in Pink: Crossdressing Delight in a Purple Haze!

Pretty in Pink: Crossdressing Delight in a Purple Haze!

xHamster 2 years ago

Solo Male CD Cock Tease Mind Fuck

Solo Male CD Cock Tease Mind Fuck

Clips4sale 2 years ago

Trans foot fetish compilation

Trans foot fetish compilation

KeekAss 2 years ago

SFX Sissy Mind Fuck

SFX Sissy Mind Fuck

Clips4sale 2 years ago

Han S 315

KeekAss 4 years ago

Luisella book

KeekAss 4 years ago

Hot Orgasms

Tranny.one 4 years ago

Transgender Princess CUM-SHOT Compilation - Sorona Sissy Season 1 finest Geysers Cumpilation

Transgender Princess CUM-SHOT Compilation - Sorona Sissy Season 1 finest Geysers Cumpilation

TrannyGem 4 years ago

Bissex fetichiste travesti

Bissex fetichiste travesti

KeekAss 4 years ago

Guts climaxes cumpilation. Personalsin bevy vol. 105

Guts climaxes cumpilation. Personalsin bevy vol. 105

TrannyGem 4 years ago

Femboy Jerks Hairy Cock With Johnson Toy� - sexcamts.com

Femboy Jerks Hairy Cock With Johnson Toy� - sexcamts.com

Tranny.one 4 years ago

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