Crossdressing Compilation Videos (4,814)

Crossdressers and the Fucking Machine - Compilation 2

61% HD 0:39 / 20:07

Crossdressers and the Fucking Machine - Compilation 2

FapHouse 11 months ago

Gina Outfits Ii

Gina Outfits Ii

FapHouse 11 months ago

Femboy Cums on Stockings

Femboy Cums on Stockings

xHamster 9 months ago

Crossdressers and the Fucking Machine - Compilation 4

Crossdressers and the Fucking Machine - Compilation 4

xHamster 1 year ago

Huge Ass Shemale Twerk Compilation

Huge Ass Shemale Twerk Compilation

FapHouse 1 year ago

Dick Worship and Crossdressing Encouragement Mindfuck

Dick Worship and Crossdressing Encouragement Mindfuck

Clips4sale 2 years ago

Crossdressers and the Fucking Machine - Compilation 6

Crossdressers and the Fucking Machine - Compilation 6

xHamster 1 year ago

Special Effects Solo Male CD Mind Fuck

Special Effects Solo Male CD Mind Fuck

Clips4sale 2 years ago

I enjoy being handled like a lil sissy whore

I enjoy being handled like a lil sissy whore

KeekAss 5 years ago

Guts ejaculations cumpilation. Personalsin bevy vol. 58

Guts ejaculations cumpilation. Personalsin bevy vol. 58

KeekAss 5 years ago

Guts climaxes cumpilation. Personalsin bevy vol. 39

Guts climaxes cumpilation. Personalsin bevy vol. 39

KeekAss 5 years ago

Shemale Anal Sex

Shemale Anal Sex

xHamster 3 years ago

Fledgling teenager femboy blows a load and plumbing compilation

Fledgling teenager femboy blows a load and plumbing compilation

KeekAss 3 years ago

Juggsy Ho Doll Z Cup Collection II

Juggsy Ho Doll Z Cup Collection II

xHamster 3 years ago

Juggsy X Cup Doll Collection #2

Juggsy X Cup Doll Collection #2

xHamster 3 years ago

Crossdresser Self Facial Compilation

Crossdresser Self Facial Compilation

ProPorn 6 years ago

Slutty crossdressing shemales wanking while toying their tight ass compilation

Slutty crossdressing shemales wanking while toying their tight ass compilation

Tranny.one 8 years ago

crossdresser missionary compilation - part one

crossdresser missionary compilation - part one

DrTuber 6 years ago

When Pai-chan was having Joy in the Apartment

When Pai-chan was having Joy in the Apartment

KeekAss 3 years ago

Juggsy Z Bowl Nymph Bevy #3

Juggsy Z Bowl Nymph Bevy #3

KeekAss 3 years ago

Crossdressing in underwear, periwig and stilettos hard-core

Crossdressing in underwear, periwig and stilettos hard-core

KeekAss 4 years ago

Hottest Moments Shag Compilation!

Hottest Moments Shag Compilation!

KeekAss 4 years ago

Bit of taunting in my fresh cutoffs

Bit of taunting in my fresh cutoffs

KeekAss 4 years ago

Ladyboy Arse Slammed #1

Ladyboy Arse Slammed #1

KeekAss 4 years ago

Crossdressing Shemale Gina Photo Sessions Compilation

Crossdressing Shemale Gina Photo Sessions Compilation

ShemaleSin 4 years ago

crossdresser missionary compilation - part one

crossdresser missionary compilation - part one

WinPorn 6 years ago

My sexy feet and high heels collections

My sexy feet and high heels collections

xHamster 3 years ago

Compilation mingle of sequences

Compilation mingle of sequences

KeekAss 3 years ago

RachelSexyMaid eighteen Dungeon Space Compilation No 1

RachelSexyMaid eighteen Dungeon Space Compilation No 1

KeekAss 5 years ago

Sissy Alexandra photos compilation

Sissy Alexandra photos compilation

KeekAss 4 years ago

Emotional moment from "Tranny Gina on Public Bench Playing"

Emotional moment from "Tranny Gina on Public Bench Playing"

xHamster 8 months ago

Hattabi4ik Sissy Femboy Trap Jizz Compilation

Hattabi4ik Sissy Femboy Trap Jizz Compilation

TrannyGem 7 months ago

Pretty in Pink: Adorable Crossdressing Styles to Swoon Over!

Pretty in Pink: Adorable Crossdressing Styles to Swoon Over!

FapHouse 7 months ago

Me and Lena on the Living Room

Me and Lena on the Living Room

FapHouse 8 months ago

Mega Compilation of Didlo Riding and Cumshots

Mega Compilation of Didlo Riding and Cumshots

aShemaleTube 8 months ago

Lady in Pink

xHamster 7 months ago

Sexy Crossdresser Kellycd2022 Pee Compilation

HD 0:39 / 15:00

Sexy Crossdresser Kellycd2022 Pee Compilation

FapHouse 8 months ago

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

xHamster 8 months ago

Viper Fierce Insane 70 Cumshot Complication

46% HD 0:30 / 13:08

Viper Fierce Insane 70 Cumshot Complication

Clips4sale 7 months ago

Memorable moment from "Ass Squirting Tranny Compilation"

Memorable moment from "Ass Squirting Tranny Compilation"

xHamster 8 months ago

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

HD 1:01 / 11:48

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

FapHouse 8 months ago

Worship My Feet

Worship My Feet

FapHouse 7 months ago

Must-see moment from "Cumpilation Wearing Sexy Stockings Heels Lingerie and Panties"

Must-see moment from "Cumpilation Wearing Sexy Stockings Heels Lingerie and Panties"

xHamster 9 months ago

Emotional moment from "MistressxXx mistress in lingerie jerking off"

Emotional moment from "MistressxXx mistress in lingerie jerking off"

xHamster 8 months ago

Slaying the Fashion Game: Crossdressing Style Secrets

Slaying the Fashion Game: Crossdressing Style Secrets

FapHouse 8 months ago

Iconic moment from "The Best Of A Wanking Office Gurl - compilation of the best sequences and cumshots"

Iconic moment from "The Best Of A Wanking Office Gurl - compilation of the best sequences and cumshots"

xHamster 8 months ago

Twink Iranian Femboy

Twink Iranian Femboy

FapHouse 10 months ago

Compilation of some of last year's scenes and new clip outside dressed in my tutu and black pantys

Compilation of some of last year's scenes and new clip outside dressed in my tutu and black pantys

xHamster 10 months ago

Scarlett's Ocean Tail REDEMPTION PMV five

Scarlett's Ocean Tail REDEMPTION PMV five

KeekAss 2 years ago

Hot Twinks Get Wild: Bathroom Fucking, Handjobs, and Crossdressing Fun!

Hot Twinks Get Wild: Bathroom Fucking, Handjobs, and Crossdressing Fun!

SexTubeSpot 3 years ago

Skinny Sissy Rozebell First Casting -tranny Love to Blow BBC

Skinny Sissy Rozebell First Casting -tranny Love to Blow BBC

FapHouse 1 year ago

Sissy New CumShot Compilation

Sissy New CumShot Compilation

xHamster 2 years ago

A edible compilation by trans Emma Ink

A edible compilation by trans Emma Ink

KeekAss 2 years ago

Hot sissy in bed

Hot sissy in bed

xHamster 2 years ago

Push a slip inside Ass and push it out

Push a slip inside Ass and push it out

xHamster 2 years ago

4K - FULL CREAM COMPILATION NEO 3

59% 4K 0:08 / 44:51

4K - FULL CREAM COMPILATION NEO 3

Clips4sale 2 years ago

Mouth-Watering

KeekAss 4 years ago

Squirting sissy cumpilation

Squirting sissy cumpilation

Tranny.one 4 years ago

I Desire of Jizm Part2

I Desire of Jizm Part2

TrannyGem 4 years ago

T-Model Beef Whistle in Close Up

T-Model Beef Whistle in Close Up

KeekAss 4 years ago

Shemale Booty Jammed #2

Shemale Booty Jammed #2

KeekAss 4 years ago

Shemale anatomy

Shemale anatomy

KeekAss 2 years ago

Compliation of Masturbating in Panties

Compliation of Masturbating in Panties

xHamster 2 years ago

Turn Me on

FapHouse 2 years ago

Cane spanking and cumshot

Cane spanking and cumshot

XXXShemalePorn 2 years ago

7連おもらし動画。男の娘おしっこ。女装おしっこ。peeing compilation

7連おもらし動画。男の娘おしっこ。女装おしっこ。peeing compilation

KeekAss 2 years ago

April Bee Jizm Compilation & Neat Up 2022

April Bee Jizm Compilation & Neat Up 2022

KeekAss 2 years ago

Mitts Free-For-All Buttfuck Ejaculation Sissygasm Cumpilation ten

Mitts Free-For-All Buttfuck Ejaculation Sissygasm Cumpilation ten

KeekAss 2 years ago

Guts climaxes cumpilation. Personalsin bevy vol. 81

Guts climaxes cumpilation. Personalsin bevy vol. 81

KeekAss 5 years ago

The Analcurve Diaries Vol. 8

The Analcurve Diaries Vol. 8

KeekAss 5 years ago

Mature Crossdresser penetrates and shoots a load

Mature Crossdresser penetrates and shoots a load

KeekAss 5 years ago

Monica

TrannyGem 4 years ago

Cumshot on Fantaisy Pantyhose, Glass Heels

Cumshot on Fantaisy Pantyhose, Glass Heels

xHamster 7 months ago

Krissy Sweets Compilation

Krissy Sweets Compilation

FapHouse 7 months ago

Jerking off Thinking of Fucking You in the Ass

Jerking off Thinking of Fucking You in the Ass

FapHouse 2 months ago

Crossdressers and the Fucking Machine - Compilation 2

Crossdressers and the Fucking Machine - Compilation 2

xHamster 2 months ago

Lady in Pink

xHamster 8 months ago

Chapter: Sit on My Cock Whore

HD 0:39 / 49:10

Chapter: Sit on My Cock Whore

FapHouse 7 months ago

Elegantly Edgy: Mixing Sexy and Cute in Crossdressing Fashion!

Elegantly Edgy: Mixing Sexy and Cute in Crossdressing Fashion!

FapHouse 7 months ago

Shemale World Gameplay Part 17

Shemale World Gameplay Part 17

FapHouse 2 months ago

Sky Resort Season 2 Gameplay 1

Sky Resort Season 2 Gameplay 1

FapHouse 2 months ago

Hillbilly Twink ( Possible Redneck Femboy) - With Bonus Sneak Peeks at Upcoming Content!

Hillbilly Twink ( Possible Redneck Femboy) - With Bonus Sneak Peeks at Upcoming Content!

Pornzona 1 month ago

Crossdressers Fucked by Fucking Machine - Compilation 3

Crossdressers Fucked by Fucking Machine - Compilation 3

xHamster 2 months ago

Crossdresser PMV

Crossdresser PMV

Clips4sale 2 years ago

Forbidden Fantasies: Indulging in Pure Seduction

Forbidden Fantasies: Indulging in Pure Seduction

xHamster 2 years ago

Smoking Lighting Up Collection

Smoking Lighting Up Collection

xHamster 1 year ago

SFX Crossdressing MindFuck Compilation

SFX Crossdressing MindFuck Compilation

Clips4sale 2 years ago

Femboy Dani Moves Around Curvy Legs in Tan Pantyhose

Femboy Dani Moves Around Curvy Legs in Tan Pantyhose

xHamster 1 year ago

Compilation

xHamster 2 years ago

Letting Out My Inward Diva: Confessions of a Crossdressing Ultra-Cutie

Letting Out My Inward Diva: Confessions of a Crossdressing Ultra-Cutie

TrannyGem 2 years ago

Sissy crossdressing guy being a blessed hoe

Sissy crossdressing guy being a blessed hoe

TrannyGem 2 years ago

little anal session in colrfull outfits

little anal session in colrfull outfits

xHamster 2 years ago

Sissy NAT0NYA, a.k.a. Treyluv's Anal Compilation

Sissy NAT0NYA, a.k.a. Treyluv's Anal Compilation

xHamster 3 years ago

Crossdressed cumshot compilation

Crossdressed cumshot compilation

MenGem 4 years ago

Joanie - My Cumpilation II (Money-Shots for Cheri)

Joanie - My Cumpilation II (Money-Shots for Cheri)

KeekAss 3 years ago

Had a demand for a tweak to down under expect you like mr otter

Had a demand for a tweak to down under expect you like mr otter

KeekAss 3 years ago

Lady Alice compilation 02 fucking session with large dildo and standing doggy style. hard, gape, pantyhose, high heels

Lady Alice compilation 02 fucking session with large dildo and standing doggy style. hard, gape, pantyhose, high heels

xHamster 3 years ago

Lady Alice Compilation 09 Endless Wild Passion (mesmerize Version)

Lady Alice Compilation 09 Endless Wild Passion (mesmerize Version)

xHamster 1 year ago

Overview of All My High Heels

HD 0:39 / 18:30

Overview of All My High Heels

FapHouse 1 year ago

Chinese delicious CD ZHAO

Chinese delicious CD ZHAO

aShemaleTube 8 years ago

Crossdressed cumshot compilation

Crossdressed cumshot compilation

aShemaleTube 8 years ago

Fabulous Sissy Hoes

Fabulous Sissy Hoes

KeekAss 4 years ago

immense compilation from MY FAUX-COCKS

immense compilation from MY FAUX-COCKS

TrannyGem 4 years ago

Waving compilation in two six x speed

Waving compilation in two six x speed

KeekAss 4 years ago

Gina Milk Spraying Slideshow

Gina Milk Spraying Slideshow

KeekAss 4 years ago

White femboy covering himself in his own cum, ruined orgasm

White femboy covering himself in his own cum, ruined orgasm

xHamster 4 years ago

Nymph Masker Unclothe Pub Compilation #2

Nymph Masker Unclothe Pub Compilation #2

KeekAss 2 years ago

Dani Leg Fountain Cum on Tan Pantyhose

Dani Leg Fountain Cum on Tan Pantyhose

FapHouse 3 weeks ago

Too Quickly Cumshot and Punished After Orgasm

Too Quickly Cumshot and Punished After Orgasm

xHamster 2 weeks ago

Check out the hottest homemade crossdressing compilation with small-titted mature babes

Check out the hottest homemade crossdressing compilation with small-titted mature babes

TrannyMovs 1 month ago

Naughty Cutie Cutie Pie Love Cum and Fuck

HD 0:39 / 11:13

Naughty Cutie Cutie Pie Love Cum and Fuck

FapHouse 1 month ago

Stepdaddy Big Hugs Dick Was Rimmed and Ass Got Fucked

Stepdaddy Big Hugs Dick Was Rimmed and Ass Got Fucked

FapHouse 1 month ago

Fishnets and Heels

Fishnets and Heels

FapHouse 1 month ago

Who Doesn't Luv Their Sissies Who Thoroughly Enjoy a Huge BBC in Their Tight Hot Boypussy 2

Who Doesn't Luv Their Sissies Who Thoroughly Enjoy a Huge BBC in Their Tight Hot Boypussy 2

xHamster 5 months ago

Sissy Crossdresser In The Garage, While No One Is Observing, We Determined To Fastly Drain The Pearl Juice! Its Steaming! Off The Hook! Huge Boners! Lots Of Spunk!

Sissy Crossdresser In The Garage, While No One Is Observing, We Determined To Fastly Drain The Pearl Juice! Its Steaming! Off The Hook! Huge Boners! Lots Of Spunk!

PePorn 4 months ago

A Wild Orgy, Tons of Cum, Compilation Collection! Hot Cumshots Exclusive!

A Wild Orgy, Tons of Cum, Compilation Collection! Hot Cumshots Exclusive!

xHamster 5 months ago

Desi sissy boy breakable ass, ready for breed ,

Desi sissy boy breakable ass, ready for breed ,

xHamster 4 months ago

Ropes of Cum Compilations, Hot Exclusive of Multiple Cum Orgasms From Femboy and Stepdaddy!

HD 1:01 / 11:09

Ropes of Cum Compilations, Hot Exclusive of Multiple Cum Orgasms From Femboy and Stepdaddy!

FapHouse 5 months ago

Compilation on Twink Fuck in His Smooth Narrow Hole! Jerk and Cum! Exclusive

Compilation on Twink Fuck in His Smooth Narrow Hole! Jerk and Cum! Exclusive

xHamster 5 months ago

(650) Sissy Compilation #2: Crossdresser, Sissification, Sissygasm - Zoulette (4K)

4K 0:10 / 10:00

(650) Sissy Compilation #2: Crossdresser, Sissification, Sissygasm - Zoulette (4K)

LoyalFans 2 months ago

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