Crossdressers (7,582)

PERMANENT CHASTITY. CUM IN CHASTITY. HUGE CUMSHOT.

Premium HD 13:40

PERMANENT CHASTITY. CUM IN CHASTITY. HUGE CUMSHOT.

Sheer 3 years ago

Webcam Continuation! Sissy Stretching Workout

Webcam Continuation! Sissy Stretching Workout

XHamster 1 year ago

Sissy Spit Roast

Sissy Spit Roast

LoyalFans 1 year ago

Faux Fur and Leather: Daddy’s Hidden Desire

55% 0:12 / 13:13

Faux Fur and Leather: Daddy’s Hidden Desire

Clips4sale 1 year ago

Seductive Feminization with MistressVictoria (TOPLESS) (CROSSDRESSING) (SENSUAL DOMINATION)

HD 0:10 / 21:22

Seductive Feminization with MistressVictoria (TOPLESS) (CROSSDRESSING) (SENSUAL DOMINATION)

LoyalFans 1 year ago

Young Mistress Dominant Blowjob 55

Young Mistress Dominant Blowjob 55

Clips4sale 1 year ago

GET READY TO GET RAILED! Sissy Makeup POV

GET READY TO GET RAILED! Sissy Makeup POV

Clips4sale 1 year ago

Aroma Transformation: Total Sissy Initiation PART 1

Aroma Transformation: Total Sissy Initiation PART 1

Clips4sale 11 months ago

"THE STRAP"

68% HD 0:10 / 1:15

LoyalFans 11 months ago

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1440p)

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1440p)

Clips4sale 1 year ago

Princess Dress Up Part 2 with MistressVictoria (STRAP ON) (SISSY TRAINING) (CROSSDRESSING)

HD 0:10 / 10:12

Princess Dress Up Part 2 with MistressVictoria (STRAP ON) (SISSY TRAINING) (CROSSDRESSING)

LoyalFans 10 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 9 months ago

Sissy Wardrobe Obedience

HD 0:10 / 19:38

Sissy Wardrobe Obedience

LoyalFans 10 months ago

Come dance with me baby

Come dance with me baby

Gayhub 9 months ago

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 9 Clip 1

Mature Crossdresser Fucked and Deepthroating Dick - Compilation 9 Clip 1

XHamster 9 months ago

Petite Trans Woman Sucking Crossdresser's Cock - Compilation 1

Petite Trans Woman Sucking Crossdresser's Cock - Compilation 1

APClips 4 months ago

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 8

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 8

APClips 4 months ago

Femboy Fucking Petite Trans Teen - Compilation 2

Femboy Fucking Petite Trans Teen - Compilation 2

APClips 4 months ago

Mirror And Balloon 2

HD 0:25 / 32:03

Mirror And Balloon 2

Clips4sale 3 weeks ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 9

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 9

APClips 4 months ago

Super Sexy Sissy Fucking TS Kelsey Masters - Compilation 4

Super Sexy Sissy Fucking TS Kelsey Masters - Compilation 4

APClips 4 months ago

Femboy Fucks Petite Tgirl

Femboy Fucks Petite Tgirl

APClips 4 months ago

Super Hot BBW Sissy Sucking TS Bailey Wilde's Dick

Super Hot BBW Sissy Sucking TS Bailey Wilde's Dick

APClips 4 months ago

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 1

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 1

APClips 4 months ago

Super Sexy Blonde Crossdresser Bailey Wilde Fucked - Compilation 1

Super Sexy Blonde Crossdresser Bailey Wilde Fucked - Compilation 1

APClips 4 months ago

Sissy Daisy Blowjob with Bailey Wilde - Compilation 1

Sissy Daisy Blowjob with Bailey Wilde - Compilation 1

APClips 4 months ago

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 4

Femboy Jade Madison Fucking Crossdresser Bailey Wilde Compilation 4

APClips 4 months ago

Petite Trans Teen and Crossdresser Bailey Wilde Fucking - Compilation 6

Petite Trans Teen and Crossdresser Bailey Wilde Fucking - Compilation 6

APClips 4 months ago

Petite Trans Teen Blowjob - Compilation 1

Petite Trans Teen Blowjob - Compilation 1

APClips 4 months ago

Post Op Trans Woman Masturbation - Compilation 2

Post Op Trans Woman Masturbation - Compilation 2

APClips 4 months ago

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 2

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 2

APClips 4 months ago

Super Sexy Sissy Fucking TS Kelsey Masters - Compilation 5

Super Sexy Sissy Fucking TS Kelsey Masters - Compilation 5

APClips 4 months ago

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 14

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 14

APClips 4 months ago

Femboys and The Fucking Machine - Compilation 4

Femboys and The Fucking Machine - Compilation 4

APClips 4 months ago

Crossdresser Fucking Redhead Tgirl Raw - Compilation 2

Crossdresser Fucking Redhead Tgirl Raw - Compilation 2

APClips 4 months ago

Crossdressers and The Fucking Machine - Compilation 6

Crossdressers and The Fucking Machine - Compilation 6

APClips 4 months ago

Femboy Bailey Wilde Compilation

Femboy Bailey Wilde Compilation

APClips 4 months ago

Femboy Bailey Wilde Sucking Sissy Jasmyne Jaye - Compilation 8

Femboy Bailey Wilde Sucking Sissy Jasmyne Jaye - Compilation 8

APClips 4 months ago

Very Hot Sissy Fucked - Compilation 6

Very Hot Sissy Fucked - Compilation 6

APClips 4 months ago

Two Angles Sissy Crossdresser Slut With Butt Plug in Fishnet Stockings Dildo Fucking Till Cumshot

4K 0:11 / 15:45

Two Angles Sissy Crossdresser Slut With Butt Plug in Fishnet Stockings Dildo Fucking Till Cumshot

Clips4sale 1 week ago

MISS AMMALIA: The sexologist cures you foot and cock obsession - 4K

4K 0:25 / 11:19

MISS AMMALIA: The sexologist cures you foot and cock obsession - 4K

Clips4sale 1 week 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 7 months ago

Crossdressing Thief BF made to wear & cum in GF panties kink feminization

Crossdressing Thief BF made to wear & cum in GF panties kink feminization

Clips4sale 7 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

Wish you were here

Wish you were here

XHamster 9 months ago

Becoming A Princess

Becoming A Princess

Clips4sale 8 months ago

Virgin Beta Sissy Training – Crossdressing and Ass Worship - virgin humiliation pov - chastity cage - tease and denial - faggot training - sissy slut

HD 0:10 / 10:32

Virgin Beta Sissy Training – Crossdressing and Ass Worship - virgin humiliation pov - chastity cage - tease and denial - faggot training - sissy slut

LoyalFans 7 months ago

Hungry Crossdresser Ass Gets a Hard Dick

Hungry Crossdresser Ass Gets a Hard Dick

XHamster 7 months ago

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

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

Clips4sale 2 years ago

MAKEUP TRANSFORMATION DEPENDENCY: Makeup Dependency Mesmerize [Power of Makeup] [Makeup] [Makeup Tutorial] [Makeup Transformation] [Transformation Fantasy]

MAKEUP TRANSFORMATION DEPENDENCY: Makeup Dependency Mesmerize [Power of Makeup] [Makeup] [Makeup Tutorial] [Makeup Transformation] [Transformation Fantasy]

Clips4sale 2 years ago

Horny trans secretary

Horny trans secretary

Clips4sale 10 months ago

Sissy Makeover: Goddess Dresses You in Pink Panties & Stuffs Your Hole Full for Your Date

Sissy Makeover: Goddess Dresses You in Pink Panties & Stuffs Your Hole Full for Your Date

Clips4sale 9 months ago

Oops, everyone knows you're a sissy now WMV

HD 0:27 / 10:08

Oops, everyone knows you're a sissy now WMV

Clips4sale 9 months ago

Nightgown and Flower-y Seamless Thong Try On

Nightgown and Flower-y Seamless Thong Try On

Clips4sale 8 months ago

mindless submissive

mindless submissive

Clips4sale 1 year ago

Inflatable Plug Use

Inflatable Plug Use

Clips4sale 2 years ago

A PAINFUL PLEASURE - An Erotic BDSM Mind Melting Series

A PAINFUL PLEASURE - An Erotic BDSM Mind Melting Series

Clips4sale 2 years ago

CROSSDRESSED AND CUCKOLDING TRAINING - Erotic Fantasy Mind Melt

CROSSDRESSED AND CUCKOLDING TRAINING - Erotic Fantasy Mind Melt

Clips4sale 2 years ago

SISSY SLUT CHASTITY TRAINING - Compelled Chastity Mind Fuck [Chastity] [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage]

SISSY SLUT CHASTITY TRAINING - Compelled Chastity Mind Fuck [Chastity] [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage]

Clips4sale 2 years 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 2 years 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 2 years 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 2 years 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

Humiliation, spitting, smoking fetish: Domdeluxury and Countess Olivia humiliate tinder beta, Role Play

Humiliation, spitting, smoking fetish: Domdeluxury and Countess Olivia humiliate tinder beta, Role Play

Clips4sale 9 months ago

Home Spa for my Feet, soap, your cock as a bath sponge and hot water

HD 0:10 / 25:35

Home Spa for my Feet, soap, your cock as a bath sponge and hot water

LoyalFans 8 months ago

Slut Prison - Made to Crossdress

HD 0:10 / 10:51

Slut Prison - Made to Crossdress

LoyalFans 1 year ago

Deep Throat, Strap-On & Feminisation: Mistress Lexy Noir Trains Her Sissies

Deep Throat, Strap-On & Feminisation: Mistress Lexy Noir Trains Her Sissies

LoyalFans 3 months ago

DIVINE FEMININITY FOR CROSSDRESSERS AND SISSIES - Feminization Training, Sissification

HD 0:30 / 30:45

DIVINE FEMININITY FOR CROSSDRESSERS AND SISSIES - Feminization Training, Sissification

Clips4sale 3 months ago

Transgirl Cock Milking & Drinking Cum

Transgirl Cock Milking & Drinking Cum

Clips4sale 4 months ago

HOT Trans Cassandra LoveLox POV Blowjob

4K 0:25 / 10:32

HOT Trans Cassandra LoveLox POV Blowjob

Clips4sale 4 months ago

Red Wubble Blowing in the Backyard

HD 0:26 / 14:32

Red Wubble Blowing in the Backyard

Clips4sale 4 months ago

Incredibly Sexy Sissy Solo

Incredibly Sexy Sissy Solo

Clips4sale 6 months ago

Crossdresser Bailey Wilde Fucking Petite Trans Teen Compilation 4

Crossdresser Bailey Wilde Fucking Petite Trans Teen Compilation 4

Clips4sale 6 months ago

HOTTEST Femboy Fucked Mega Compilation

HOTTEST Femboy Fucked Mega Compilation

Clips4sale 6 months ago

Petite Trans Teen and Crossdresser Bailey Wilde Fucking Compilation 1

Petite Trans Teen and Crossdresser Bailey Wilde Fucking Compilation 1

Clips4sale 6 months ago

Sexy Tatted Trans Chloe T Star Sucking Cock Compilation 1

4K 0:25 / 20:00

Sexy Tatted Trans Chloe T Star Sucking Cock Compilation 1

Clips4sale 4 months ago

Feminizing the Jock

Feminizing the Jock

XHamster 3 months ago

Table Top - Trans Becki Bottomz and Jake Grand

4K 0:25 / 36:45

Table Top - Trans Becki Bottomz and Jake Grand

Clips4sale 4 months ago

Sissy Jerking Anal Solo Compilation

70% HD 0:10 / 20:10

Sissy Jerking Anal Solo Compilation

LoyalFans 3 months ago

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 2

HD 0:10 / 20:01

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 2

LoyalFans 3 months ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 17

HD 0:10 / 20:01

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 17

LoyalFans 3 months ago

Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

LoyalFans 3 months ago

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 13

HD 0:10 / 20:25

Very Pretty Crossdresser Fucking and Sucking Redhead Tgirl Raw - Compilation 13

LoyalFans 3 months ago

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 4

HD 0:10 / 20:00

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 4

LoyalFans 3 months ago

Sissy Daisy Sucking and Getting Fucked by Bailey Wilde - Compilation 4

HD 0:10 / 36:14

Sissy Daisy Sucking and Getting Fucked by Bailey Wilde - Compilation 4

LoyalFans 3 months ago

Mistress Strapon Fucking Sissy Bailey Wilde - Compilation 50

HD 0:10 / 29:20

Mistress Strapon Fucking Sissy Bailey Wilde - Compilation 50

LoyalFans 3 months ago

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 7

HD 0:10 / 20:02

Sexy Crossdressing Goddess Fucking Trans Kelsey Masters - Compilation 7

LoyalFans 3 months ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 15

HD 0:10 / 20:07

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 15

LoyalFans 3 months ago

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 12

HD 0:10 / 20:06

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 12

LoyalFans 3 months ago

Petite Trans Woman Deepthroating TS Bailey Wilde's Cock - Compilation 4

HD 0:10 / 20:13

Petite Trans Woman Deepthroating TS Bailey Wilde's Cock - Compilation 4

LoyalFans 3 months ago

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 10

HD 0:10 / 20:07

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 10

LoyalFans 3 months ago

Super Sexy Blonde Femboy Fucked Compilation

HD 0:10 / 28:26

Super Sexy Blonde Femboy Fucked Compilation

LoyalFans 3 months ago

Straight Guy Fucking Femboy for First Time

4K 0:55 / 29:58

Straight Guy Fucking Femboy for First Time

Clips4sale 4 months ago

Total Eclipse of the Farts MP4

HD 0:25 / 15:11

Total Eclipse of the Farts MP4

Clips4sale 3 months ago

Hottie Trans Woman Fucked Mega Compilation

4K 0:55 / 44:25

Hottie Trans Woman Fucked Mega Compilation

Clips4sale 4 months ago

Pink Haired Tgirl Deepthroating Cock Compilation

HD 0:55 / 58:25

Pink Haired Tgirl Deepthroating Cock Compilation

Clips4sale 4 months ago

Mature Sissy Fucked by Silly Character

4K 0:25 / 21:07

Mature Sissy Fucked by Silly Character

Clips4sale 4 months ago

Onion Booty Trap Queen's Temptation: Luxurious Lace & Stockinged Soles

Onion Booty Trap Queen's Temptation: Luxurious Lace & Stockinged Soles

XHamster 3 months ago

Hot Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

Hot Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

LoyalFans 3 months ago

Hottest Sissy Compilation

HD 0:10 / 22:44

Hottest Sissy Compilation

LoyalFans 3 months ago

Sissy Daisy Sucking and Getting Fucked by Bailey Wilde - Compilation 1

HD 0:10 / 20:01

Sissy Daisy Sucking and Getting Fucked by Bailey Wilde - Compilation 1

LoyalFans 3 months ago

Mistress Pegging Crossdresser Bailey Wilde - Compilation 9

HD 0:10 / 20:04

Mistress Pegging Crossdresser Bailey Wilde - Compilation 9

LoyalFans 3 months ago

Fashion Mesh Thong -Couldn't Wait- Try On

Fashion Mesh Thong -Couldn't Wait- Try On

Clips4sale 1 month ago

Gooning the fuck out! - No Audio

Gooning the fuck out! - No Audio

APClips 2 months ago

Sexy red dress and pantyhose

Sexy red dress and pantyhose

Clips4sale 7 months ago

Sissy Cumshots Compilation

Sissy Cumshots Compilation

XHamster 7 months ago

She's in the Way (Sissy Homewrecking)

HD 0:17 / 12:07

She's in the Way (Sissy Homewrecking)

IWantClips 2 years ago

Million Or Makeover Episode 1

HD 0:25 / 15:13

Million Or Makeover Episode 1

Clips4sale 1 month ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 22

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 22

APClips 4 months ago

Fucking Big Ass Sissy in Chastity - Compilation 2

HD 0:10 / 20:07

Fucking Big Ass Sissy in Chastity - Compilation 2

LoyalFans 4 months ago

18 minutes of heaven

HD 0:10 / 18:38

18 minutes of heaven

LoyalFans 4 months ago

Trans Cassandra LoveLox Fucking Guy and Getting Fucked

HD 0:10 / 40:25

Trans Cassandra LoveLox Fucking Guy and Getting Fucked

LoyalFans 4 months ago

TS Becki Bottomz and Jake Grand

HD 0:10 / 18:56

TS Becki Bottomz and Jake Grand

LoyalFans 4 months ago

Crossdresser Uses Tool to Get Boobs

Crossdresser Uses Tool to Get Boobs

SpankBang 2 years ago

Mistress Tgirl MILF Dominates Bottom Boy

55% HD 0:10 / 28:07

Mistress Tgirl MILF Dominates Bottom Boy

LoyalFans 4 months ago

Rapper Fucking Mature Crossdresser

Rapper Fucking Mature Crossdresser

Clips4sale 4 months ago

Pretty Petite Trans Fucked - Compilation 10

HD 0:10 / 20:47

Pretty Petite Trans Fucked - Compilation 10

LoyalFans 4 months ago

Crossdresser Barebacked Dildo While in Chastity

Crossdresser Barebacked Dildo While in Chastity

SpankBang 2 years ago

Rapper Fucking Hot Femboy

4K 0:25 / 1:06:59

Rapper Fucking Hot Femboy

Clips4sale 4 months ago

Scooby Fucking Hot Femboy

4K 0:25 / 11:03

Scooby Fucking Hot Femboy

Clips4sale 4 months ago

13 14 15 16 17

7,582 results found

Related searches

Narrow your search

two crossdressers

Models

Model Galore - The biggest XXX collection of the newest and the best porn videos of your favorite models. The #1 place for fans of adult content creators!

Parents

Modelgalore.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Modelgalore.com. All rights reserved.

© 2026 Modelgalore.com. All rights reserved.