Crossdressing (2,490)

Enter The Facesitter

Enter The Facesitter

xHamster 4 years ago

Sissy Maid Counseling

Sissy Maid Counseling

LoyalFans 1 year ago

Kinky German Mature Anal Threesome

Kinky German Mature Anal Threesome

xHamster 9 years ago

CFNM pegging domina fists sub in balls squeezing lesson

CFNM pegging domina fists sub in balls squeezing lesson

Some.Porn 1 year ago

A Disgrace to Our Town Part 2

A Disgrace to Our Town Part 2

xHamster 11 months ago

Daily Sissy Training

62% HD 0:10 / 13:47

Daily Sissy Training

LoyalFans 2 years ago

A Disgrace to Our Town Part 2

53% 1:01 / 11:07

A Disgrace to Our Town Part 2

FapHouse 11 months ago

A Disgrace to Our Town Part 2

A Disgrace to Our Town Part 2

xHamster 11 months 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 1 year ago

Double dom with Lady Valeska: Spitroasting whimping sissy

54% HD 0:10 / 5:25

Double dom with Lady Valeska: Spitroasting whimping sissy

LoyalFans 1 year ago

Fishnets dominatrix kicks guys balls

Fishnets dominatrix kicks guys balls

Some.Porn 1 year ago

Big Ass Phone, Tiny Dick: Watch Him Struggle

Big Ass Phone, Tiny Dick: Watch Him Struggle

XXXShake 1 year ago

Strong trio of thick mistresses reverse gangbang one sissy boy

Strong trio of thick mistresses reverse gangbang one sissy boy

Fapality 8 years ago

Hibiki Ootsuki takes on multiple partners in steamy group session

62% HD 5:00 / 1:00:14

Hibiki Ootsuki takes on multiple partners in steamy group session

JavHD 5 months ago

Queen Melanin Pegging Returns Part 2

Queen Melanin Pegging Returns Part 2

LoyalFans 1 year ago

Fuck Me Hard

Some.Porn 9 months ago

Sissy Games : When my Cuckold Husband Meets my Lover - Maitresse Julia Femdom

Sissy Games : When my Cuckold Husband Meets my Lover - Maitresse Julia Femdom

xHamster 2 years ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

Dafreeporn 1 year ago

Misha Cross Goes to British Swinger Party

Misha Cross Goes to British Swinger Party

Some.Porn 1 year ago

GILF 3WAY

Some.Porn 1 year ago

20 Mins Sissy Get Ready Make up with Me

20 Mins Sissy Get Ready Make up with Me

xHamster 1 month ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

FreePorn8 1 year ago

Your Most Humiliating Orgasm Yet

49% HD 0:10 / 37:33

Your Most Humiliating Orgasm Yet

LoyalFans 2 years ago

Your Most Humiliating Orgasm Yet (FULL HD)

56% HD 1:00 / 37:33

Your Most Humiliating Orgasm Yet (FULL HD)

Clips4sale 2 years ago

So you like to wear girls clothes? (Sissy Training Protocol)

HD 0:10 / 10:37

So you like to wear girls clothes? (Sissy Training Protocol)

LoyalFans 1 week ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

SortPorn 2 years ago

Vintage Crossdressing - Part 1

Vintage Crossdressing - Part 1

BigTitsLust 2 years ago

Maitresse Julia - When i Give a Long Footjob in Pantyhose and Socks ! Reward for my slave !

Maitresse Julia - When i Give a Long Footjob in Pantyhose and Socks ! Reward for my slave !

xHamster 3 years ago

Crossdressers Group Hot Threesome Sex

59% HD 0:39 / 16:31

Crossdressers Group Hot Threesome Sex

FapHouse 6 months ago

mother I'd like to fuck corporalist bangs jerking off trannys taut butt with large ding-dong

mother I'd like to fuck corporalist bangs jerking off trannys taut butt with large ding-dong

MatureTubeHere 9 months ago

Succulent chick Gina Killmer gets seduced and fucked

Succulent chick Gina Killmer gets seduced and fucked

XVideos 6 years ago

Queen Melanin Power Pegging Returns Full Clip

Queen Melanin Power Pegging Returns Full Clip

LoyalFans 1 year ago

Rocky horror imposed crossdressing

65% HD 0:27 / 10:31

Rocky horror imposed crossdressing

FapHouse 5 years ago

Hot Tub Domination - 720HD

67% 0:14 / 8:31

Hot Tub Domination - 720HD

Clips4sale 3 years ago

Submissive Husband in Panties Deepthroats and Takes Massive Black Cock (SUB ENG 1080) BBC - ANAL - DEGRADATION

HD 0:29 / 24:13

Submissive Husband in Panties Deepthroats and Takes Massive Black Cock (SUB ENG 1080) BBC - ANAL - DEGRADATION

Clips4sale 2 months ago

Sissy Slut Session

HD 0:10 / 10:16

Sissy Slut Session

LoyalFans 3 years ago

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

44% HD 1:01 / 10:01

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

FapHouse 9 months ago

Pantyhose Domination for Milf Handjob Fetish

Pantyhose Domination for Milf Handjob Fetish

XXXShake 4 years ago

Fotowettbewerb: 1000 keusche Loser Pr&auml_sentation Video #1

Fotowettbewerb: 1000 keusche Loser Pr&auml_sentation Video #1

XVideos 6 years ago

Featuring Ksenias Crossdressing Smut

Featuring Ksenias Crossdressing Smut

01Tube 8 months ago

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

56% HD 0:10 / 9:57

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

LoyalFans 9 months ago

Femdom babe crossdresses guy into a girlfriend part 1

Femdom babe crossdresses guy into a girlfriend part 1

Cremz 4 years ago

Who needs a boyfriend when I have this?

Who needs a boyfriend when I have this?

LoyalFans 1 month ago

Like Her Body? Then, Live in It!

50% HD 0:10 / 16:59

Like Her Body? Then, Live in It!

LoyalFans 1 year ago

The Summer Of Hormones

The Summer Of Hormones

LoyalFans 2 years ago

Crossdressers Group Hot Threesome Sex

53% HD 1:01 / 16:31

Crossdressers Group Hot Threesome Sex

FapHouse 6 months ago

Pink Bow Car Washer

Pink Bow Car Washer

LoyalFans 2 years ago

You Bet Your Ass

52% HD 0:10 / 29:22

You Bet Your Ass

LoyalFans 11 months ago

8 Girl Orgy Only Slutlana Would Approve!

8 Girl Orgy Only Slutlana Would Approve!

Some.Porn 6 months ago

French Amateur Mom Humiliates Her Small Dick Stepson

French Amateur Mom Humiliates Her Small Dick Stepson

xHamster 2 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 7 months ago

POV - Handjob for femboy

66% 1:01 / 8:14

POV - Handjob for femboy

FapHouse 2 years ago

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

45% HD 0:10 / 18:15

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

LoyalFans 2 years 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

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!

xHamster 7 months ago

The Feminization Room - with Remy D and Megan Daw

46% HD 0:10 / 58:28

The Feminization Room - with Remy D and Megan Daw

LoyalFans 1 year ago

Femdom honey crossdresses chap into a girlfriend part 1

Femdom honey crossdresses chap into a girlfriend part 1

Amateur8 3 years ago

Submissives enjoy BDSM orgy 4K

Submissives enjoy BDSM orgy 4K

Some.Porn 1 year ago

pissing in the mouth. let s open your mouth i ll fill it. lick my pussy and feet in stockings.

55% HD 0:16 / 5:38

pissing in the mouth. let s open your mouth i ll fill it. lick my pussy and feet in stockings.

PornBox 3 years ago

Flat chest , Cameltoe, SwimsuitBodysuit horny skinny Goddess

53% HD 0:10 / 5:05

Flat chest , Cameltoe, SwimsuitBodysuit horny skinny Goddess

LoyalFans 2 weeks ago

Rocky horror imposed crossdressing

61% HD 1:01 / 10:31

Rocky horror imposed crossdressing

FapHouse 5 years ago

Sabrina-Jade: Damsel in dress

Sabrina-Jade: Damsel in dress

Some.Porn 1 year ago

Melissa Seeks Kissing Advice From Miss Hendrix

61% HD 0:39 / 6:57

Melissa Seeks Kissing Advice From Miss Hendrix

FapHouse 6 months ago

LaBella Slays dick on Crossdressing Big Dick Sissy

58% 0:39 / 16:03

LaBella Slays dick on Crossdressing Big Dick Sissy

LaBellaDX 1 year ago

Melissa Seeks Kissing Advice From Miss Hendrix

69% HD 0:39 / 6:57

Melissa Seeks Kissing Advice From Miss Hendrix

FapHouse 6 months 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

milf fickt das gemuese beim Ausflug mit den kolleginnen

milf fickt das gemuese beim Ausflug mit den kolleginnen

xHamster 3 years ago

BBC Worship Pantyhose Fetish

55% 4K 1:01 / 24:01

BBC Worship Pantyhose Fetish

FapHouse 3 months ago

Nauli yoga practice Cum on my BELLY button

65% HD 0:10 / 4:44

Nauli yoga practice Cum on my BELLY button

LoyalFans 2 weeks ago

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

PissVids 3 years ago

You Bet Your Ass

57% HD 0:10 / 29:22

You Bet Your Ass

LoyalFans 1 year ago

Deep Submission: Pleasure Trigger Installed

Deep Submission: Pleasure Trigger Installed

LoyalFans 1 day ago

Our Little Secret - Full Movie - The Lost Files

HD 0:10 / 46:49

Our Little Secret - Full Movie - The Lost Files

LoyalFans 2 days ago

Various Changing Scenes July 2025

66% HD 1:01 / 8:35

Various Changing Scenes July 2025

FapHouse 7 months ago

Cruel Collar Party

55% HD 0:10 / 9:20

Cruel Collar Party

LoyalFans 3 years ago

Contractually dedicated to feet

Contractually dedicated to feet

LoyalFans 1 year ago

Do You Really Want to Fuck Your Mother?

59% HD 0:10 / 7:19

Do You Really Want to Fuck Your Mother?

LoyalFans 1 year 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 3 years ago

Special Sissy Friends Part II (WL1704)

HD 0:10 / 15:50

Special Sissy Friends Part II (WL1704)

LoyalFans 1 week ago

Crossdressing Damsel Gets Fully Feminized And Tied Up By Mistress Stella Liberty

Crossdressing Damsel Gets Fully Feminized And Tied Up By Mistress Stella Liberty

AbXXX 1 year ago

Pegging Sissy Slave With Gloved Handjob - Sorceress Morgana Soles Black Nitrile Gloves HJ And Strapon Fucking Sissy Slut 1080

HD 0:10 / 10:00

Pegging Sissy Slave With Gloved Handjob - Sorceress Morgana Soles Black Nitrile Gloves HJ And Strapon Fucking Sissy Slut 1080

LoyalFans 1 week ago

PART 2
New Face Sitting and Ass Worship Video for Gooners

PART 2 New Face Sitting and Ass Worship Video for Gooners

LoyalFans 5 days ago

You've Lost the Bet; Now, It's Time to Carry Out Your Punishment

HD 0:10 / 18:20

You've Lost the Bet; Now, It's Time to Carry Out Your Punishment

LoyalFans 4 days ago

Admission of being a Sissy - Mean girls

Admission of being a Sissy - Mean girls

xHamster 3 years ago

Sissy Personal Trainer

66% HD 0:10 / 24:16

Sissy Personal Trainer

LoyalFans 2 weeks ago

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Lesbian8 4 months ago

Dominatrix Mistress April, transformation into a whore

HD 0:39 / 1:11:26

Dominatrix Mistress April, transformation into a whore

FapHouse 3 years ago

We're coming back n. 2

We're coming back n. 2

xHamster 2 years ago

British Femdoms Humiliate Voyeur Sissy

British Femdoms Humiliate Voyeur Sissy

Jizzberry 4 years ago

Leaky, Pantied And Slutty

HD 0:10 / 12:10

Leaky, Pantied And Slutty

LoyalFans 3 days ago

Dominatrix Mistress April - Cock into clit

Dominatrix Mistress April - Cock into clit

xHamster 1 week ago

Feminization, Crossdressing & Sissification

63% HD 0:39 / 57:20

Feminization, Crossdressing & Sissification

FapHouse 1 month ago

THICC Kinky Sissy Nurse Lucy Keeping Covid Secure For Mistress

Premium HD 6:15

THICC Kinky Sissy Nurse Lucy Keeping Covid Secure For Mistress

XVideosRed 5 years ago

7 Mini Skirts

65% HD 0:10 / 8:32

LoyalFans 3 years ago

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

56% HD 0:39 / 10:01

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

FapHouse 9 months 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 10 months ago

New Cum Eating Instructions (CEI) Video

New Cum Eating Instructions (CEI) Video

LoyalFans 5 days ago

Getting My Sissy Ready for Cock

62% HD 0:10 / 11:07

Getting My Sissy Ready for Cock

LoyalFans 3 years ago

Sissy Zone Cycle 3

60% HD 0:10 / 21:12

Sissy Zone Cycle 3

LoyalFans 1 year ago

French Amateur Stepmom Humiliates Her Small Dick Stepson

62% 1:01 / 5:45

French Amateur Stepmom Humiliates Her Small Dick Stepson

FapHouse 2 years ago

You'll Wear Panties Forever

You'll Wear Panties Forever

Pornfact 2 weeks ago

😩 Put YOUR Stockings On Too Masturbate Together 😈

HD 0:10 / 10:54

😩 Put YOUR Stockings On Too Masturbate Together 😈

LoyalFans 6 days ago

Pantyhose Aerobics Class For Sissies

61% HD 0:10 / 15:12

Pantyhose Aerobics Class For Sissies

LoyalFans 11 months ago

Live With Being Bullied

54% HD 0:10 / 4:58

Live With Being Bullied

LoyalFans 2 years ago

Dominatrix Mistress April - Cock into clit

63% HD 0:39 / 16:07

Dominatrix Mistress April - Cock into clit

FapHouse 3 years ago

Strapon and Sissy Play Is My Favorite

Strapon and Sissy Play Is My Favorite

xHamster 3 months ago

Therapy-Fantasy For Pussies

55% HD 0:10 / 15:24

Therapy-Fantasy For Pussies

LoyalFans 11 months ago

Feminization, Crossdressing & Sissification

60% HD 1:01 / 57:20

Feminization, Crossdressing & Sissification

FapHouse 1 month ago

Brand New Harsh Humiliation Video With Spitting

LoyalFans 1 day ago

Burgers set Big CHEWING experience

61% HD 0:10 / 3:40

Burgers set Big CHEWING experience

LoyalFans 1 month ago

Nhdtc-005 I Cant Break The Habit Of Being Lesbianized Every Tuesday A Sensitive Chick Falls Into The Lesbian Hairdressers Trap And Climaxes Until She Pisses Herself In The Crossdressers Clothes

Nhdtc-005 I Cant Break The Habit Of Being Lesbianized Every Tuesday A Sensitive Chick Falls Into The Lesbian Hairdressers Trap And Climaxes Until She Pisses Herself In The Crossdressers Clothes

ManySex 11 months ago

Brand New Nylons Try On Haul and Worship Video

LoyalFans 1 day ago

Two Mistress's and a Sissy Whore

Two Mistress's and a Sissy Whore

xHamster 1 year ago

Womanhood 101: Bras

HD 0:39 / 16:51

Womanhood 101: Bras

FapHouse 7 months ago

Femboi Debut

64% HD 0:10 / 11:37

LoyalFans 2 years ago

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

HD 1:01 / 10:53

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

FapHouse 2 weeks ago

Lost Another Bet?

Lost Another Bet?

LoyalFans 1 year ago

Sissy Boyfriend Found Out and Pegged

50% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 3 years ago

What’s my name part 2

What’s my name part 2

MomVids 2 years ago

Virgin Becomes My Sissy

Virgin Becomes My Sissy

LoyalFans 2 years ago

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