Crossdressing (2,719)

Louboutins, Standing CBT & Heavy Weights

63% HD 0:39 / 8:53

Louboutins, Standing CBT & Heavy Weights

FapHouse 7 months ago

the best ruined orgasm compilation

the best ruined orgasm compilation

BDSMDoe 1 year ago

if a guy lets me use his ass on the first date he is my type

if a guy lets me use his ass on the first date he is my type

BDSMDoe 1 year ago

You Bet Your Ass

52% HD 0:10 / 29:22

You Bet Your Ass

LoyalFans 8 months ago

Sissy Pantyhose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Sissy Pantyhose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

PornFreeNow 1 month ago

Jenna Fucks Big Bottomed Sissy Maid Tiffany Deep in the Ass... She's Such a Slut!

Jenna Fucks Big Bottomed Sissy Maid Tiffany Deep in the Ass... She's Such a Slut!

FapHouse 4 months ago

Let's Change Gender Roles and Spice Up Our Play

55% HD 0:10 / 18:24

Let's Change Gender Roles and Spice Up Our Play

LoyalFans 6 months ago

Enter The Facesitter

Enter The Facesitter

xHamster 3 years ago

LaBella Slays dick on Crossdressing Big Dick Sissy

57% 0:39 / 16:03

LaBella Slays dick on Crossdressing Big Dick Sissy

LaBellaDX 1 year ago

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porn reality show with lesbian anal sex, strap-on, foot fetish, crossdressing and more!

XVideosRed 2 years ago

Fuck Me Hard

Some.Porn 6 months ago

Double dom with Lady Valeska: Spitroasting whimping sissy

54% HD 0:10 / 5:25

Double dom with Lady Valeska: Spitroasting whimping sissy

LoyalFans 11 months ago

femdom babe crossdresses guy into a girlfriend, part 2

femdom babe crossdresses guy into a girlfriend, part 2

PornWorld 10 years ago

feminization process

feminization process

BDSMDoe 1 year ago

STEPBROTHER TURNED SISSY AT OUR SLUMBER PARTY 1080P - ELLIE IDOL

64% HD 0:10 / 21:05

STEPBROTHER TURNED SISSY AT OUR SLUMBER PARTY 1080P - ELLIE IDOL

APClips 10 months ago

Maitresse Julia - Klelia my Sissy Slave in Chastity is Frustrated (Tease and Denial). For me ? An incredible Facesitting

Maitresse Julia - Klelia my Sissy Slave in Chastity is Frustrated (Tease and Denial). For me ? An incredible Facesitting

xHamster 2 years ago

Hibiki Ootsuki takes on multiple partners in steamy group session

HD 5:00 / 1:00:14

Hibiki Ootsuki takes on multiple partners in steamy group session

JavHD 3 months ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

Amateur8 2 years ago

The Feminization Room - with Remy D and Megan Daw

49% HD 0:10 / 58:28

The Feminization Room - with Remy D and Megan Daw

LoyalFans 1 year ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

BigTitsLust 2 years ago

Hospital Anal 3 – The Billing

61% 0:10 / 9:46

Hospital Anal 3 – The Billing

APClips 10 months ago

Crossdressers In Lingerie

HD 0:30 / 2:14:00

Crossdressers In Lingerie

AEBN 4 years ago

Maitresse Julia - What right to a slave who is no longer useful ? My smells! Humiliation !

Maitresse Julia - What right to a slave who is no longer useful ? My smells! Humiliation !

xHamster 3 years ago

Juicy Lucy British Booty Bitch

Premium HD 0:44

Juicy Lucy British Booty Bitch

XVideosRed 3 years ago

Plapping' machine makes my Sissy squirt in her cage

60% HD 0:10 / 8:26

Plapping' machine makes my Sissy squirt in her cage

LoyalFans 5 months ago

Sissy Slut Caught and Humiliated

Premium VR 34:09

Sissy Slut Caught and Humiliated

SexLikeReal 9 months ago

Queen Melanin Takes the Strapon to Hoodbitch

61% HD 0:10 / 10:11

Queen Melanin Takes the Strapon to Hoodbitch

LoyalFans 2 months ago

Submissives enjoy BDSM orgy 4K

Submissives enjoy BDSM orgy 4K

Some.Porn 1 year ago

dominatrix pegging her sissy slave in wedding dress

dominatrix pegging her sissy slave in wedding dress

BDSMDoe 1 year ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

SortPorn 2 years ago

Femdom Latex Hottie Anissa Kate Crossdresses Boyfrie

Femdom Latex Hottie Anissa Kate Crossdresses Boyfrie

AbXXX 2 years ago

Witch gender transformation sissification (1080p mp4)

46% HD 0:11 / 22:37

Witch gender transformation sissification (1080p mp4)

Clips4sale 2 years ago

Hot Tub Domination - 720HD

67% 0:14 / 8:31

Hot Tub Domination - 720HD

Clips4sale 3 years ago

Learn to obey your mistress! Part 3

52% 0:10 / 8:07

Learn to obey your mistress! Part 3

APClips 10 months ago

Sissygasm Tutorial - Sissification with the Lady of Feminization

Sissygasm Tutorial - Sissification with the Lady of Feminization

xHamster 2 years ago

Slut For Chrissy Daniels w Lance Hart STRAPON PEGGING SISSY

Slut For Chrissy Daniels w Lance Hart STRAPON PEGGING SISSY

XVideos 8 years ago

Whore Stories (Volume #1, Scene #1)

Whore Stories (Volume #1, Scene #1)

XVideos 9 months ago

pretty sissy slave in pink

pretty sissy slave in pink

BDSMDoe 1 year ago

GILF 3WAY

Some.Porn 1 year ago

Anal Hooked Rubberdoll

Anal Hooked Rubberdoll

LoyalFans 4 years ago

nurse pegging her sissy patient who feminized his face with makeup

nurse pegging her sissy patient who feminized his face with makeup

BDSMDoe 1 year ago

Femdoms and crossdressers in hardcore orgy

Femdoms and crossdressers in hardcore orgy

xHamster 7 months ago

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

60% HD 0:10 / 9:57

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

LoyalFans 7 months ago

Transforming You into My Sweet, Short, Pantiless Maid

51% HD 0:10 / 22:16

Transforming You into My Sweet, Short, Pantiless Maid

LoyalFans 1 year ago

French Amateur Mom Humiliates Her Small Dick Stepson

French Amateur Mom Humiliates Her Small Dick Stepson

xHamster 2 years ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

55% HD 0:39 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 7 months ago

POV - Handjob for femboy

65% 0:39 / 8:14

POV - Handjob for femboy

FapHouse 2 years ago

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Some.Porn 1 year ago

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BDSMDoe 1 year ago

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SukaPorn 1 year ago

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sissy boy in stockings and heels testing the sex machine. anal fuck with big dildo

SukaPorn 1 year ago

Like Her Body? Then, Live in It!

51% HD 0:10 / 16:59

Like Her Body? Then, Live in It!

LoyalFans 10 months ago

Your Most Humiliating Orgasm Yet

51% HD 0:10 / 37:33

Your Most Humiliating Orgasm Yet

LoyalFans 2 years ago

We're coming back n. 2

We're coming back n. 2

xHamster 1 year ago

Cum Covered Foot Licking Sissy

HD 0:10 / 18:04

Cum Covered Foot Licking Sissy

LoyalFans 10 months ago

femdom babe crossdresses guy into a girlfriend, part 2

femdom babe crossdresses guy into a girlfriend, part 2

SukaPorn 1 year ago

A Disgrace to Our Town Part 2

A Disgrace to Our Town Part 2

xHamster 8 months ago

Anissa Kate - Femdom Darling Crossdresses Guy Into A Girlfriend

Anissa Kate - Femdom Darling Crossdresses Guy Into A Girlfriend

ManySex 1 year ago

Crossdressing Her Husband

Crossdressing Her Husband

InPorn 4 years ago

Sabrina-Jade: Damsel in dress

Sabrina-Jade: Damsel in dress

Some.Porn 1 year ago

Kinky German Older Anal Trio

Kinky German Older Anal Trio

SortPorn 2 years ago

Lesbian crossdressers kissing and strapon fucking

Lesbian crossdressers kissing and strapon fucking

Pornvee 6 days ago

Get to Sucking Being Fucked Sissy Gangbang

HD 0:10 / 13:35

Get to Sucking Being Fucked Sissy Gangbang

LoyalFans 2 years ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

47% HD 1:01 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 7 months ago

Submissive Under Her Hot Booty and Boots

50% 0:10 / 14:54

Submissive Under Her Hot Booty and Boots

APClips 10 months ago

A Disgrace to Our Town Part 2

A Disgrace to Our Town Part 2

xHamster 9 months ago

2 new slaves ready for training part 1 - full fist ahead

70% 0:10 / 8:34

2 new slaves ready for training part 1 - full fist ahead

APClips 10 months ago

Sissy Anal Training with my fuck machine!

55% HD 0:10 / 6:41

Sissy Anal Training with my fuck machine!

LoyalFans 1 week ago

Misha Cross Goes to British Swinger Party

Misha Cross Goes to British Swinger Party

Some.Porn 1 year ago

So Much Cock for Faggot

HD 0:10 / 10:03

So Much Cock for Faggot

LoyalFans 1 year ago

Banged Raw by a Sexy Crossdressing Slut

Banged Raw by a Sexy Crossdressing Slut

Jizzberry 11 months ago

How Deep Is Your Love? 2/2

47% 0:10 / 11:04

How Deep Is Your Love? 2/2

APClips 10 months ago

Crossdressers Group Hot Threesome Sex

55% HD 1:01 / 16:31

Crossdressers Group Hot Threesome Sex

FapHouse 3 months ago

SISSYBRIT COLLECTION

35% 0:10 / 1:48:32

SISSYBRIT COLLECTION

APClips 10 months ago

Her chained & caged sissy slave

4K 0:49 / 10:18

Her chained & caged sissy slave

Clips4sale 2 years ago

Femdom Latex Hottie Anissa Kate Crossdresses Boyfriend For Anal Marathon Gp598

Femdom Latex Hottie Anissa Kate Crossdresses Boyfriend For Anal Marathon Gp598

AbXXX 1 year ago

Education to an Anal-Whore 1/2

53% 0:10 / 7:48

Education to an Anal-Whore 1/2

APClips 10 months ago

Locktober pegging: caged, leashed, and fucked into submission by Domme gf - HD

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Locktober pegging: caged, leashed, and fucked into submission by Domme gf - HD

Clips4sale 2 years ago

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MatureTubeHere 6 months ago

Hot stripper Nyomi Banxxx punishes a really annoying client at the club

Hot stripper Nyomi Banxxx punishes a really annoying client at the club

XVideos 5 years ago

Femdom babe crossdresses guy into a girlfriend part 1

Femdom babe crossdresses guy into a girlfriend part 1

Cremz 4 years ago

Angry prison nurse Gianna Michaels has to down dumb lockstepper who likes to v. discipline in their correctional labour institution

Angry prison nurse Gianna Michaels has to down dumb lockstepper who likes to v. discipline in their correctional labour institution

XVideos 5 years ago

Sissy fashion show

HD 0:10 / 12:10

Sissy fashion show

LoyalFans 1 year ago

Over the Knee Spanks and Milking

HD 0:10 / 22:55

Over the Knee Spanks and Milking

LoyalFans 1 month ago

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Romantic evening nylon sex in white lingerie

xHamster 2 years ago

Mad Madge gets Whipped! mp4

HD 0:57 / 12:16

Mad Madge gets Whipped! mp4

Clips4sale 2 years ago

Foxy Femboy Trap Queen - Presenting My Perfect Bussy/Butthole & Gaping It Wide With My Cute Foxtail Butt Plug With SPREADING & WINKING!!!

Foxy Femboy Trap Queen - Presenting My Perfect Bussy/Butthole & Gaping It Wide With My Cute Foxtail Butt Plug With SPREADING & WINKING!!!

APClips 10 months ago

Femdom latex hottie Anissa Kate crossdresses boyfriend for anal marathon GP598

Femdom latex hottie Anissa Kate crossdresses boyfriend for anal marathon GP598

XVideos 6 years ago

Femdom Babe Crossdresses Guy Into A Girlfriend, Part 1

Femdom Babe Crossdresses Guy Into A Girlfriend, Part 1

XVideos 10 years ago

FOOTJOB IN GREY WOOL RIBBED TIGHTS

FOOTJOB IN GREY WOOL RIBBED TIGHTS

Clips4sale 1 year ago

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milf fickt das gemuese beim Ausflug mit den kolleginnen

xHamster 3 years ago

sissy whore ready to be pegged

sissy whore ready to be pegged

BDSMDoe 1 year ago

Admission of being a Sissy - Mean girls

Admission of being a Sissy - Mean girls

xHamster 3 years ago

Rocky horror imposed crossdressing

62% HD 1:01 / 10:31

Rocky horror imposed crossdressing

FapHouse 5 years ago

Rocky horror imposed crossdressing

65% HD 0:27 / 10:31

Rocky horror imposed crossdressing

FapHouse 5 years ago

Czech babe in man's costume dominates her lover and gets fucked and jizzed

Czech babe in man's costume dominates her lover and gets fucked and jizzed

XCafe 7 months ago

Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

xHamster 2 years ago

Sissy Boyfriend Found Out and Pegged

53% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 2 years ago

Your Roommate Encourages You to Dress Up for Hot Play

51% HD 0:10 / 23:29

Your Roommate Encourages You to Dress Up for Hot Play

LoyalFans 7 months ago

Live With Being Bullied

58% HD 0:10 / 4:58

Live With Being Bullied

LoyalFans 2 years ago

Assistance With Breeding

Assistance With Breeding

Some.Porn 1 year ago

Various Changing Scenes July 2025

64% HD 1:01 / 8:35

Various Changing Scenes July 2025

FapHouse 4 months ago

I Can't Believe I'm Babysitting a 21-Year-Old Virgin

46% HD 0:10 / 18:15

I Can't Believe I'm Babysitting a 21-Year-Old Virgin

LoyalFans 2 years ago

Lena Paul's Massive Tits Weren't Enough for the Machine - S10: E8

Lena Paul's Massive Tits Weren't Enough for the Machine - S10: E8

Sexu 2 years ago

Your Roommate Encourages You to Dress Up for Hot Play

63% HD 0:10 / 23:29

Your Roommate Encourages You to Dress Up for Hot Play

LoyalFans 10 months ago

Melissa Seeks Kissing Advice From Miss Hendrix

69% HD 0:39 / 6:57

Melissa Seeks Kissing Advice From Miss Hendrix

FapHouse 3 months ago

Whoops Its Gone

59% HD 0:10 / 6:50

Whoops Its Gone

LoyalFans 1 year ago

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the feminized bitch in stockings wants to cum in his panties. sissy in the chastity belt.

PornBox 2 years ago

Cute

HD 0:10 / 10:17

LoyalFans 2 weeks ago

Strapon and Sissy Play Is My Favorite

Strapon and Sissy Play Is My Favorite

FapHouse 1 month ago

PEGGED 5 - Tiny Girl Feminizes

Premium VR 16:20

PEGGED 5 - Tiny Girl Feminizes

SexLikeReal 1 year ago

how long could the male slave last

how long could the male slave last

BDSMDoe 10 months ago

#97 Nurses Do Face Sitting to a Male

HD 0:39 / 10:39

#97 Nurses Do Face Sitting to a Male

FapHouse 1 week ago

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Lesbian8 1 month ago

Do You Really Want to Fuck Your Mother?

60% HD 0:10 / 7:19

Do You Really Want to Fuck Your Mother?

LoyalFans 1 year ago

BBC Worship Pantyhose Fetish

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FapHouse 1 week ago

Good Morning Hormone Tits

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LoyalFans 2 years ago

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SukaPorn 1 year ago

Let's Change Gender Roles and Spice Up Our Play

HD 0:10 / 18:24

Let's Change Gender Roles and Spice Up Our Play

LoyalFans 3 months ago

Two Mistress's and a Sissy Whore

Two Mistress's and a Sissy Whore

xHamster 10 months ago

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