Crossdressing Videos - Trans (13,557)

Getting Wet For My Date

66% HD 0:30 / 11:41

Getting Wet For My Date

Clips4sale 1 year ago

50 FREE HANDS CUMSHOTS FREE HANDS COMPILATION

50 FREE HANDS CUMSHOTS FREE HANDS COMPILATION

Clips4sale 1 year ago

I crave sex Nymphomaniac 2

I crave sex Nymphomaniac 2

Clips4sale 1 year ago

Little Silky, Sissy Whore

Little Silky, Sissy Whore

Clips4sale 1 year ago

Athena's Latex Slut

71% 0:30 / 44:39

Athena's Latex Slut

Clips4sale 1 year ago

Sissy boy fucked by older step-daddy bear raw footage

HD 0:30 / 18:20

Sissy boy fucked by older step-daddy bear raw footage

Clips4sale 1 year ago

Daddy Gives Head to His Beautiful Sissy Step Daughter

54% HD 0:30 / 15:07

Daddy Gives Head to His Beautiful Sissy Step Daughter

Clips4sale 1 year ago

Milking The Maid

70% HD 0:10 / 39:52

Milking The Maid

LoyalFans 1 year ago

smoking wearing catsuit

smoking wearing catsuit

Clips4sale 1 year ago

Rubber Drone Edging and Anal Training

Rubber Drone Edging and Anal Training

Clips4sale 1 year ago

Sissy training tutorial

HD 0:30 / 10:17

Sissy training tutorial

Clips4sale 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

Cumshot 💦

LoyalFans 1 year ago

1234 I'm your Pussless Anal Whore

1234 I'm your Pussless Anal Whore

Clips4sale 1 year ago

Misty 120s Seduction - SFL323

Misty 120s Seduction - SFL323

Clips4sale 1 year ago

Borgia's Sissy Tasks - Gender Bender Slut! (720p)

Borgia's Sissy Tasks - Gender Bender Slut! (720p)

Clips4sale 1 year ago

BOSSY British TS - SPH & JOI

BOSSY British TS - SPH & JOI

Clips4sale 1 year ago

Helpless Goth Crossdress Public Hanging Wedgie

Helpless Goth Crossdress Public Hanging Wedgie

Clips4sale 1 year ago

You Soft Sissy Bi Bitch!

You Soft Sissy Bi Bitch!

Clips4sale 1 year ago

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Clips4sale 1 year ago

Fisting for Sissy Holes

Fisting for Sissy Holes

Clips4sale 1 year ago

Sissy Crossdresser Moaning Riding Huge Dildo & Multiple Anal Orgasms Hands Free Sissygasm & Cumplay

55% 0:30 / 9:41

Sissy Crossdresser Moaning Riding Huge Dildo & Multiple Anal Orgasms Hands Free Sissygasm & Cumplay

Clips4sale 1 year ago

SISSYGASM CUM COMPILATION

57% 0:30 / 6:20

SISSYGASM CUM COMPILATION

Clips4sale 1 year ago

Pantied Sissy JOI

72% HD 0:10 / 11:55

Pantied Sissy JOI

LoyalFans 1 year ago

Glamour Girls Kicking 86

Glamour Girls Kicking 86

Clips4sale 1 year ago

Sissy 50

Clips4sale 1 year ago

Sexy Sling & Micro Bikinis ~ TheBikini Try on & Show

61% 0:30 / 7:29

Sexy Sling & Micro Bikinis ~ TheBikini Try on & Show

Clips4sale 1 year ago

Tooth Fairy Caught

Tooth Fairy Caught

LoyalFans 1 year ago

cute canadian gurl

cute canadian gurl

Clips4sale 1 year ago

Sissy Crossdresser Moaning & Masturbating in High Heels & Stockings Cums Multiple Sissygasms #2

65% 0:30 / 7:31

Sissy Crossdresser Moaning & Masturbating in High Heels & Stockings Cums Multiple Sissygasms #2

Clips4sale 1 year ago

Sissy or crossdresser?

Sissy or crossdresser?

Clips4sale 3 years ago

Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum

67% HD 1:00 / 28:24

Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum

Clips4sale 1 year ago

Feet Worship 1044

Feet Worship 1044

Clips4sale 1 year ago

Fat Ass CD Sissy blows and gets fucked by a Monster BBC Fiona Fortune

54% 0:30 / 16:43

Fat Ass CD Sissy blows and gets fucked by a Monster BBC Fiona Fortune

Clips4sale 1 year ago

bedroom sissy

Clips4sale 1 year ago

smoking fetish nun

smoking fetish nun

Clips4sale 1 year ago

Smothering while tied to the dentist chair MP4 (480p) starring Mistress Biancabound

57% HD 0:30 / 12:47

Smothering while tied to the dentist chair MP4 (480p) starring Mistress Biancabound

Clips4sale 1 year ago

THE BALLERINA GIRL (mp4) PART 2

THE BALLERINA GIRL (mp4) PART 2

Clips4sale 1 year ago

Never Touching Pussy Again - Craving Only BBC Mind Remolding 20 min (MaleDom)

Never Touching Pussy Again - Craving Only BBC Mind Remolding 20 min (MaleDom)

Clips4sale 1 year ago

Huge mess on my see through top

Huge mess on my see through top

Clips4sale 1 year ago

sissy makeover 2 - sissification, feminisation, encouraged bi, exposure, slave task trainning, verbal humiliation

sissy makeover 2 - sissification, feminisation, encouraged bi, exposure, slave task trainning, verbal humiliation

Clips4sale 1 year ago

Coaching You into M-to-F Transition

66% 4K 0:29 / 18:54

Coaching You into M-to-F Transition

Clips4sale 1 year ago

Latex Maid Drone Bound Programming

Latex Maid Drone Bound Programming

Clips4sale 1 year ago

Day 37 Sissy Training Programme: Tips for the curvy sissy

HD 0:30 / 10:02

Day 37 Sissy Training Programme: Tips for the curvy sissy

Clips4sale 1 year ago

Accept The Household Humiliation

Accept The Household Humiliation

LoyalFans 1 year ago

Chastity Cage Spit Roasting (WMV HD)

HD 0:30 / 10:17

Chastity Cage Spit Roasting (WMV HD)

Clips4sale 1 year ago

The Sissy Slut - WMV - 1920

The Sissy Slut - WMV - 1920

Clips4sale 2 years ago

Your leather sissy slut Feminization training starts now

47% HD 0:20 / 10:23

Your leather sissy slut Feminization training starts now

Clips4sale 1 year ago

A STRAP ON FOR A GOOD SISSY

A STRAP ON FOR A GOOD SISSY

Clips4sale 1 year ago

Cuckolding 223

Clips4sale 1 year ago

Kicking 86

Clips4sale 1 year ago

Backyard Bondage

56% HD 0:10 / 6:27

Backyard Bondage

LoyalFans 1 year ago

Dominant Handjob 211 mp-4

Dominant Handjob 211 mp-4

Clips4sale 1 year ago

Crossdressing Slave Orally and Anally Submitted - Part 2

HD 0:30 / 10:46

Crossdressing Slave Orally and Anally Submitted - Part 2

Clips4sale 1 year ago

his personal fucktoy

his personal fucktoy

Clips4sale 1 year ago

YOU ARE ONE SEXY BITCH by Domina Paulina

HD 0:11 / 12:59

YOU ARE ONE SEXY BITCH by Domina Paulina

Clips4sale 5 years ago

Visual CD MindFuck

Visual CD MindFuck

Clips4sale 2 years ago

Dressing Up My Slutty Sissy (mp4)

Dressing Up My Slutty Sissy (mp4)

Clips4sale 1 year ago

Cumming on white toes in fishnet socks

Cumming on white toes in fishnet socks

Clips4sale 1 year ago

Everyone Knows I Owned You

60% HD 0:10 / 8:18

Everyone Knows I Owned You

LoyalFans 1 year ago

Hot Ashes & Harder Desires - SFL330

Hot Ashes & Harder Desires - SFL330

Clips4sale 1 year ago

Futa GF Pegging Session: Stress Relief with My Monster Toy and Endless Assgasms - FHD

64% 0:29 / 12:07

Futa GF Pegging Session: Stress Relief with My Monster Toy and Endless Assgasms - FHD

Clips4sale 1 year ago

How To Crossdress Like A Real Whore

How To Crossdress Like A Real Whore

Clips4sale 1 year ago

Cigarette Kisses and Lipstick - SFL333

Cigarette Kisses and Lipstick - SFL333

Clips4sale 1 year ago

Lola Bathroom Play - S037

HD 0:10 / 20:53

Lola Bathroom Play - S037

Clips4sale 1 year ago

Femboy ass spreading, fingering, and wearing sexy outfits!

Femboy ass spreading, fingering, and wearing sexy outfits!

Clips4sale 1 year ago

Preparing for Your First Girls Night Out

Preparing for Your First Girls Night Out

Clips4sale 1 year ago

MOBILE - Goddess Kiffa - Four Goddess Anal Gang Bang Crossdresser Slave - Part 2 - STRAPON - GANG BANG- FEMDOM- ASS PLAY - DILDO - ASS FUCKING - WHOLE FUCKING - CD -

MOBILE - Goddess Kiffa - Four Goddess Anal Gang Bang Crossdresser Slave - Part 2 - STRAPON - GANG BANG- FEMDOM- ASS PLAY - DILDO - ASS FUCKING - WHOLE FUCKING - CD -

Clips4sale 1 year ago

Honey Bree's ASStonishing Debut!! MOV Version

Honey Bree's ASStonishing Debut!! MOV Version

Clips4sale 1 year ago

Gentle Discipline: The Headmistress's Secret Inspection

Gentle Discipline: The Headmistress's Secret Inspection

Clips4sale 1 year ago

Young Mistress Foot Worship 1044 wmv

Young Mistress Foot Worship 1044 wmv

Clips4sale 1 year ago

pink pony club

Clips4sale 1 year ago

Ladysilva virtual handjob

Ladysilva virtual handjob

Clips4sale 1 year ago

Drilling For Ass & SmotherBox (1080p)

55% HD 0:30 / 5:28

Drilling For Ass & SmotherBox (1080p)

Clips4sale 1 year ago

39-04 Nude Fucking Machine Toy Blow Job

39-04 Nude Fucking Machine Toy Blow Job

Clips4sale 3 years ago

DVD 16 Crossdresser CD Stacey in Purple School Skirt by File Cabinets

DVD 16 Crossdresser CD Stacey in Purple School Skirt by File Cabinets

Clips4sale 1 year ago

Kinky Sub Girl Cunt Busted By Mistress Sabrina Valentine (STANDARD WMV)

Kinky Sub Girl Cunt Busted By Mistress Sabrina Valentine (STANDARD WMV)

Clips4sale 1 year ago

Princess Karlie Gives You A Sissy Makeover (720p)

Princess Karlie Gives You A Sissy Makeover (720p)

Clips4sale 1 year ago

Creating A New Feminized Doll Stage 1 (WMV)

Creating A New Feminized Doll Stage 1 (WMV)

Clips4sale 1 year ago

Beach Babe wanks her cock in her car

Beach Babe wanks her cock in her car

Clips4sale 1 year ago

Ladysilva my hot big dick, go suck me

Ladysilva my hot big dick, go suck me

Clips4sale 1 year ago

Ladysilva, why don't you come fuck my hot ass here on the beach?

Ladysilva, why don't you come fuck my hot ass here on the beach?

Clips4sale 1 year ago

Ladysilva masturbating thinking about a hot ass to put my big dick in

Ladysilva masturbating thinking about a hot ass to put my big dick in

Clips4sale 1 year ago

Ladysilva masturbating and cumming deliciously

Ladysilva masturbating and cumming deliciously

Clips4sale 1 year ago

Chilling Before My Date

Chilling Before My Date

Clips4sale 1 year ago

Ladysilva naked on the beach come fuck my hot ass

Ladysilva naked on the beach come fuck my hot ass

Clips4sale 1 year ago

Facefucking Session with Daddy and His Sissy Boi

50% HD 0:30 / 7:46

Facefucking Session with Daddy and His Sissy Boi

Clips4sale 1 year ago

Feminine Friday

Feminine Friday

LoyalFans 1 year ago

CUM SLUT TRAINING MIND FUCK - Sissy Slut Training Mind Fuck

CUM SLUT TRAINING MIND FUCK - Sissy Slut Training Mind Fuck

Clips4sale 1 year ago

sissy maids are insatiable

sissy maids are insatiable

Clips4sale 1 year ago

Panty Shame

Clips4sale 1 year ago

Sissies’ Anal Competition: Who'll Stay in the Cage? Who's in the Basement? Mistress Julia

Sissies’ Anal Competition: Who'll Stay in the Cage? Who's in the Basement? Mistress Julia

Clips4sale 1 year ago

Kelly's Crossdressing Slut (MKV)

47% 0:30 / 29:47

Kelly's Crossdressing Slut (MKV)

Clips4sale 1 year ago

Be My Pool-Bitch For Hot-Girl Summer!

Be My Pool-Bitch For Hot-Girl Summer!

Clips4sale 1 year ago

Beta Boyfriend Bitch Application

Beta Boyfriend Bitch Application

Clips4sale 1 year ago

Ladysilva naked my hot ass on The beach

Ladysilva naked my hot ass on The beach

Clips4sale 1 year ago

Debit Card Clout

Debit Card Clout

Clips4sale 1 year ago

Chastity Cage Spit Roasting (MP4 HD)

HD 0:30 / 10:18

Chastity Cage Spit Roasting (MP4 HD)

Clips4sale 1 year ago

Kinky Sub Girl Cunt Busted By Mistress Sabrina Valentine (MP4)

Kinky Sub Girl Cunt Busted By Mistress Sabrina Valentine (MP4)

Clips4sale 1 year ago

Fun at the Park, Wedgie, Stuck, Panty Shots

Fun at the Park, Wedgie, Stuck, Panty Shots

Clips4sale 1 year ago

Skirts For A Sissy Secretary

HD 0:10 / 12:23

Skirts For A Sissy Secretary

LoyalFans 1 year ago

Ladysilva crosdresser de calcinha na praia que bunda gostosa

Ladysilva crosdresser de calcinha na praia que bunda gostosa

Clips4sale 1 year ago

You Can't Miss It - Daddy Gives Me a Triple Orgasm!!!!

65% HD 0:30 / 17:51

You Can't Miss It - Daddy Gives Me a Triple Orgasm!!!!

Clips4sale 1 year ago

Ladysilva crossdresser in panties and pantyhose on the bed doing a cam show 02

Ladysilva crossdresser in panties and pantyhose on the bed doing a cam show 02

Clips4sale 1 year ago

YOU ARE THE GIRL MIND FUCK - Becoming The Girl, Sissy Training, YOU ARE BECOMING A GIRL

50% 0:30 / 32:33

YOU ARE THE GIRL MIND FUCK - Becoming The Girl, Sissy Training, YOU ARE BECOMING A GIRL

Clips4sale 1 year ago

THE SISSY, THE BULL, THE CHASTITY, THE LINGERIE, AND THE KEYHOLDER MESMERIZE

63% 0:30 / 27:07

THE SISSY, THE BULL, THE CHASTITY, THE LINGERIE, AND THE KEYHOLDER MESMERIZE

Clips4sale 1 year ago

Spy on me and watch my TS dick cum heavy

Spy on me and watch my TS dick cum heavy

Clips4sale 1 year ago

Valentine's Picnic Date with Pharaoh Feet (Lemon Cake)

HD 0:10 / 12:10

Valentine's Picnic Date with Pharaoh Feet (Lemon Cake)

LoyalFans 1 year ago

Your Little Secret

67% 0:57 / 9:55

Your Little Secret

Clips4sale 2 years ago

Sissy acceptance: there's no going back

57% HD 0:30 / 5:31

Sissy acceptance: there's no going back

Clips4sale 1 year ago

Do You Like My Nylons?

Do You Like My Nylons?

Clips4sale 2 years ago

Owllete blows up and pops inflatable crocodile

Owllete blows up and pops inflatable crocodile

Clips4sale 1 year ago

Holly smoking at night - SFL228

Holly smoking at night - SFL228

Clips4sale 3 years ago

Mesmerized To Wear Panties Sissy Training Lola Minaj Trans MP4HD

55% 0:29 / 6:43

Mesmerized To Wear Panties Sissy Training Lola Minaj Trans MP4HD

Clips4sale 3 years ago

Birthday Bi Party - Part Seven - 1 - MP4

Birthday Bi Party - Part Seven - 1 - MP4

Clips4sale 3 years ago

Cum In A Glass III

HD 0:11 / 16:23

Cum In A Glass III

Clips4sale 3 years ago

The Gooner Glitch Trans Gooning Mesmerize Mind fuck MP4SD

The Gooner Glitch Trans Gooning Mesmerize Mind fuck MP4SD

Clips4sale 3 years ago

Machine Milked & Fucked T-Gurl

HD 0:10 / 10:24

Machine Milked & Fucked T-Gurl

Clips4sale 3 years ago

Switch It Up Suck A Dick Full Trans Lola Minaj Cock Sucking Ass Worship WMVSD

Switch It Up Suck A Dick Full Trans Lola Minaj Cock Sucking Ass Worship WMVSD

Clips4sale 3 years ago

Sensual Synthetic PMV

Sensual Synthetic PMV

Clips4sale 3 years ago

30 31 32 33 34

13,557 results found

Related categories

Transvestite Strap-On Trans Trans Fucks Trans Trans Fucks Girl Trans Fucks Guy Sissy Ladyboy Trans Domination Trans Tgirl Trans Solo Hermaphrodite Trans Big Cock Femboy 18+ Femboy BBC Trans BBC (Big Black Cock) Feminization Ebony Trans Trans Post-Op Trans Compilation

Narrow your search

crossdressing creampie crossdressing compilation crossdressing orgy crossdressing husband crossdressing mature crossdressing gangbang crossdressing bbc caught crossdressing crossdressing solo crossdressing teen 18+ crossdressing blowjob crossdressing threesome crossdressing asian crossdressing outdoor amateur crossdressing crossdressing webcam

Categories Pornstars

Parents

Pornmd.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 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.