Crossdressing (1,661)

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

55% HD 0:10 / 15:31

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

LoyalFans 1 year ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

70% HD 0:29 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

IWantClips 2 months ago

Making of Sissy Sasha

45% HD 0:25 / 33:34

Making of Sissy Sasha

IWantClips 2 months ago

"Ultimate co- erced Bi BBC sissy cuck humiliation training" [18.49 minutes]

66% HD 0:10 / 18:49

"Ultimate co- erced Bi BBC sissy cuck humiliation training" [18.49 minutes]

LoyalFans 3 weeks ago

Your Most Humiliating Orgasm Yet

53% HD 0:10 / 37:33

Your Most Humiliating Orgasm Yet

LoyalFans 2 years ago

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PissVids 3 years ago

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

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PissVids 3 years ago

Our Little Secret - Full Movie - The Lost Files

62% HD 0:10 / 46:49

Our Little Secret - Full Movie - The Lost Files

LoyalFans 5 months ago

🌺 Sissy Training - Learn to suck dick! 🌺

56% HD 0:10 / 7:33

🌺 Sissy Training - Learn to suck dick! 🌺

LoyalFans 11 months ago

fansly - ruby onyx sissy whore ready to be pegged porn video

fansly - ruby onyx sissy whore ready to be pegged porn video

BDSMShip 2 years ago

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

64% HD 0:10 / 18:20

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

LoyalFans 5 months ago

Sissy Girl Training Cum Countdown

61% HD 0:20 / 22:14

Sissy Girl Training Cum Countdown

IWantClips 2 months ago

Mistress Lady Renee - Making you dress - mp4

72% 0:16 / 14:03

Mistress Lady Renee - Making you dress - mp4

Clips4sale 1 year ago

GFE Feminization Encouragement - Your First Satin Lingerie

65% HD 0:30 / 23:13

GFE Feminization Encouragement - Your First Satin Lingerie

IWantClips 2 months ago

Pantyhose Aerobics Class For Sissies

61% HD 0:10 / 15:12

Pantyhose Aerobics Class For Sissies

LoyalFans 1 year ago

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

HD 0:30 / 1:23:42

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

PornBox 2 years ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

51% HD 0:10 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

LoyalFans 4 months ago

Sissy Slut Session

HD 0:10 / 10:16

Sissy Slut Session

LoyalFans 3 years ago

HOW TO MAKE A BISEXUAL CUCKOLD OUT OF A HUSBAND CHASTITY BELT! ONLY ANAL FUCK!

Premium HD 18:18

HOW TO MAKE A BISEXUAL CUCKOLD OUT OF A HUSBAND CHASTITY BELT! ONLY ANAL FUCK!

Sheer 3 years ago

Sissy Bimbo For Men

57% HD 0:15 / 5:26

Sissy Bimbo For Men

Clips4sale 3 weeks ago

Getting My Sissy Ready for Cock

58% HD 0:10 / 11:07

Getting My Sissy Ready for Cock

LoyalFans 3 years ago

Sissy Faggot Feminization Mega Pack!

56% HD 0:25 / 1:37:32

Sissy Faggot Feminization Mega Pack!

IWantClips 2 years ago

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

62% HD 0:10 / 16:00

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

LoyalFans 2 months 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

Discovering My Sissy Step-Nephew 4K

63% 4K 0:30 / 11:33

Discovering My Sissy Step-Nephew 4K

Clips4sale 1 year ago

Humbled Sissy Gets a 72 Stroke Caning from Nikki Whiplash (WL1779)

57% HD 0:10 / 19:11

Humbled Sissy Gets a 72 Stroke Caning from Nikki Whiplash (WL1779)

LoyalFans 8 months ago

Leaky Little Step-Sissy

HD 0:25 / 15:15

Leaky Little Step-Sissy

IWantClips 2 months ago

Sissy Makeover

HD 0:22 / 11:09

IWantClips 2 months ago

Sissies Have To Swallow

65% HD 0:10 / 10:22

Sissies Have To Swallow

LoyalFans 3 years 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 6 months ago

sissy training and feminisation: Matriarch Ezada Sinn and Mistress Kennya transform him into Their sissy bitch

HD 0:10 / 15:33

sissy training and feminisation: Matriarch Ezada Sinn and Mistress Kennya transform him into Their sissy bitch

LoyalFans 1 month ago

Bullied Beta

55% HD 0:10 / 6:43

LoyalFans 2 years ago

Little Dick Sissy Faggot Reject Bimbo Cumdumpsters Deserve Chastity

50% HD 0:25 / 12:16

Little Dick Sissy Faggot Reject Bimbo Cumdumpsters Deserve Chastity

IWantClips 2 years ago

SISSY PRISON 002

51% 4K 0:30 / 14:02

SISSY PRISON 002

Clips4sale 10 months ago

My Plugged Sissy

53% HD 0:10 / 6:18

My Plugged Sissy

LoyalFans 5 months ago

SISSY PRISON Part 1 *MOV*

65% 4K 0:31 / 15:11

SISSY PRISON Part 1 *MOV*

Clips4sale 10 months ago

Queen Melanin Power Pegging Returns Part 1

Queen Melanin Power Pegging Returns Part 1

Clips4sale 1 year ago

What Will You Do to Have Sex with Me?

63% HD 0:10 / 13:02

What Will You Do to Have Sex with Me?

LoyalFans 2 months ago

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

73% HD 0:30 / 19:21

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

Clips4sale 2 years ago

Permanent Punisher

Permanent Punisher

IWantClips 9 months ago

Double Locked Sissy - Star Nine

38% 0:13 / 21:59

Double Locked Sissy - Star Nine

Clips4sale 3 years ago

cum in chastity. step mommy footjob in stockings. your stuffed balls.

60% HD 0:23 / 7:40

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PornBox 3 years ago

crazy anal fuck. fisting and pegging hubby in chastity belt

63% HD 0:16 / 5:25

crazy anal fuck. fisting and pegging hubby in chastity belt

PornBox 3 years ago

You Heard Wrong

66% HD 0:10 / 10:29

You Heard Wrong

LoyalFans 2 years ago

Cruel Collar Party

47% HD 0:10 / 9:20

Cruel Collar Party

LoyalFans 3 years ago

compilation turning stepbrother into a sissy bitch. magic feminization. syssification

HD 0:30 / 12:00

compilation turning stepbrother into a sissy bitch. magic feminization. syssification

PornBox 3 years ago

Tinkle Boy Nylon Sniffer

HD 0:10 / 24:43

Tinkle Boy Nylon Sniffer

LoyalFans 2 years ago

52% HD 0:10 / 3:21

Brand New Harsh Humiliation Video With Spitting

LoyalFans 5 months ago

Our Little Secret

62% HD 0:10 / 5:56

Our Little Secret

LoyalFans 2 years ago

Discovering My Sissy Step-Nephew

59% 0:30 / 11:33

Discovering My Sissy Step-Nephew

Clips4sale 1 year ago

Small Penis Pictures

Small Penis Pictures

LoyalFans 2 years ago

Everything You Crave: Tits, Pussy & Pure Pleasure🥵

Everything You Crave: Tits, Pussy & Pure Pleasure🥵

LoyalFans 5 months ago

Claudia

HD 0:10 / 10:07

LoyalFans 3 years 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

Your Most Humiliating Orgasm Yet (FULL HD)

57% HD 1:00 / 37:33

Your Most Humiliating Orgasm Yet (FULL HD)

Clips4sale 2 years ago

Queen Melanin Power Pegging Returns Full Clip

Queen Melanin Power Pegging Returns Full Clip

Clips4sale 1 year ago

7 Mini Skirts

65% HD 0:10 / 8:32

LoyalFans 3 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 1 year ago

Let's Change Gender Roles and Spice Up Our Play

49% HD 0:10 / 18:24

Let's Change Gender Roles and Spice Up Our Play

LoyalFans 1 year ago

Good Morning Hormone Tits

57% HD 0:10 / 6:59

Good Morning Hormone Tits

LoyalFans 3 years ago

Nylon Sissy Slave - Candle Boxxx

50% HD 0:10 / 13:03

Nylon Sissy Slave - Candle Boxxx

LoyalFans 2 years ago

Becoming My Sissy Slave

HD 0:26 / 1:01:26

Becoming My Sissy Slave

IWantClips 2 months ago

Empress CatastroV and Mistress Baton - Sissy make-over and bare-handed spanking

HD 0:10 / 16:24

Empress CatastroV and Mistress Baton - Sissy make-over and bare-handed spanking

LoyalFans 1 year ago

The Feminization Room - with Remy D and Megan Daw

47% HD 0:10 / 58:28

The Feminization Room - with Remy D and Megan Daw

LoyalFans 1 year ago

Step-Mommy's Naughty Sissy

HD 0:10 / 11:16

Step-Mommy's Naughty Sissy

LoyalFans 2 years ago

Premature Sissy Squirt Cuck EXXXTENDED VERSION

HD 0:10 / 15:31

Premature Sissy Squirt Cuck EXXXTENDED VERSION

LoyalFans 2 years ago

Witch gender transformation sissification (1080p wmv)

51% HD 0:11 / 22:37

Witch gender transformation sissification (1080p wmv)

Clips4sale 3 years ago

DRYHUMP SESSION WITH HELENA PART 1

DRYHUMP SESSION WITH HELENA PART 1

Clips4sale 3 years ago

Fucked a slave after long weeks of testing

Fucked a slave after long weeks of testing

LoyalFans 4 weeks ago

Girl Transformation Complete: Sissy Breeding with Dommy Rose

57% HD 0:10 / 21:29

Girl Transformation Complete: Sissy Breeding with Dommy Rose

LoyalFans 9 months ago

Humiliated with Ugly Panties

57% HD 0:10 / 10:19

Humiliated with Ugly Panties

LoyalFans 3 years ago

Der Anal Plug für Slut Candy auf der Fickbank/ The Anal Plug for Slut Candy on the Fuckbench (english vid)

Der Anal Plug für Slut Candy auf der Fickbank/ The Anal Plug for Slut Candy on the Fuckbench (english vid)

LoyalFans 2 years ago

Sissy Boyfriend Found Out and Pegged

60% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 3 years ago

Slutty SISSY CLOWN Twin

HD 0:10 / 10:50

Slutty SISSY CLOWN Twin

LoyalFans 4 years ago

Road Head & Bred

HD 0:30 / 11:23

Road Head & Bred

Clips4sale 11 months ago

Transforming You into My Sweet, Short, Pantiless Maid

49% HD 0:10 / 22:16

Transforming You into My Sweet, Short, Pantiless Maid

LoyalFans 2 years ago

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

LoyalFans 2 months ago

Sissy Fuckingmachine Cumshot in Suspension / Sissy Fickmaschinen Cumshot fest gebunden

HD 0:10 / 10:05

Sissy Fuckingmachine Cumshot in Suspension / Sissy Fickmaschinen Cumshot fest gebunden

LoyalFans 4 years ago

Misty Turns You Into Her Pretty Little Sissy

Premium HD 19:08

Misty Turns You Into Her Pretty Little Sissy

Clips4sale 1 year ago

Contractually dedicated to feet

Contractually dedicated to feet

LoyalFans 1 year ago

An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

65% 0:30 / 16:51

An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

Clips4sale 1 year ago

SMOKING SISSY SLUT FOR BBC

62% 4K 0:42 / 18:40

SMOKING SISSY SLUT FOR BBC

Clips4sale 2 years ago

Roll Ur Eyes Like A Slut (1080 HD)

Roll Ur Eyes Like A Slut (1080 HD)

Clips4sale 4 years ago

Imposed Sissy Transformation

64% HD 0:25 / 18:50

Imposed Sissy Transformation

IWantClips 3 years ago

Sissy husband & Goddess wife

HD 0:10 / 16:12

Sissy husband & Goddess wife

LoyalFans 3 weeks ago

The Summer Of Hormones

The Summer Of Hormones

LoyalFans 3 years ago

(1080P) SISSY SLUT SPITROAST - REAL SESSION FOOTAGE - Vivienne l'Amour and Genna James subject their sissy slut to a suspended paddling, spitroast, pegging, deepthroat, anal training, spanking, and pain training in a prison cell roleplay fantasy.

Premium HD 25:01

(1080P) SISSY SLUT SPITROAST - REAL SESSION FOOTAGE - Vivienne l'Amour and Genna James subject their sissy slut to a suspended paddling, spitroast, pegging, deepthroat, anal training, spanking, and pain training in a prison cell roleplay fantasy.

Clips4sale 3 weeks ago

BEST FUCKING HUGE STRAPON SISSY ANAL. THIS SLUT IS READY TO FUCK. Sissy Fucked In Chastity

Premium HD 11:06

BEST FUCKING HUGE STRAPON SISSY ANAL. THIS SLUT IS READY TO FUCK. Sissy Fucked In Chastity

Sheer 3 years ago

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

69% HD 0:29 / 24:13

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

Clips4sale 8 months ago

Witch gender transformation sissification (1080p mp4)

39% HD 0:11 / 22:37

Witch gender transformation sissification (1080p mp4)

Clips4sale 3 years ago

Sissy Summer

60% HD 0:10 / 9:53

LoyalFans 3 months ago

Sissy Training: dressing you as a girl

HD 0:10 / 14:58

Sissy Training: dressing you as a girl

LoyalFans 3 months ago

My Sissy Boss

57% HD 0:10 / 9:21

LoyalFans 2 years ago

LeGauntlet Medical pt 1

70% HD 0:10 / 11:59

LeGauntlet Medical pt 1

LoyalFans 5 years ago

Caught In Your Wife's Lingerie! Dress Up For Me, Ride Her Dildo & Eat Your Cum To Earn My Silence Or Else!

HD 0:10 / 15:38

Caught In Your Wife's Lingerie! Dress Up For Me, Ride Her Dildo & Eat Your Cum To Earn My Silence Or Else!

LoyalFans 1 month ago

She's in the Way (Sissy Homewrecking)

HD 0:17 / 12:07

She's in the Way (Sissy Homewrecking)

IWantClips 2 years ago

Ausbildung zur Nutte, danach gehst du anschaffen!

56% HD 0:25 / 9:41

Ausbildung zur Nutte, danach gehst du anschaffen!

IWantClips 4 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 1 year ago

You Asked For It Peaches

65% HD 0:10 / 8:55

You Asked For It Peaches

LoyalFans 3 years ago

To Meet The Inlaws

HD 0:33 / 15:45

To Meet The Inlaws

IWantClips 2 years ago

💖🌸April's Sissy Program - VIDEO 5 Dildo Training 🌸💖

💖🌸April's Sissy Program - VIDEO 5 Dildo Training 🌸💖

LoyalFans 2 years ago

Mistress Jewell's Bound Hooker pt 1

62% HD 0:10 / 12:50

Mistress Jewell's Bound Hooker pt 1

LoyalFans 3 years ago

SLUT PUPPET

HD 0:10 / 32:27

LoyalFans 6 months ago

Goddess Samariel feeds Her cuckold sissy hubby with Her boyfriend’s cum

Goddess Samariel feeds Her cuckold sissy hubby with Her boyfriend’s cum

Clips4sale 2 years ago

Sissy Nipple Slut Gets Used STRAPON PEGGING - 4K

4K 0:25 / 16:28

Sissy Nipple Slut Gets Used STRAPON PEGGING - 4K

Clips4sale 1 year ago

Sissy Boyfriend Found Out and Pegged - 4k

67% 4K 0:20 / 18:37

Sissy Boyfriend Found Out and Pegged - 4k

Clips4sale 3 years ago

Live With Being Bullied

54% HD 0:10 / 4:58

Live With Being Bullied

LoyalFans 2 years ago

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

66% HD 0:30 / 15:32

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

PornBox 3 years ago

Real Arab Lesbian Pussy Licking In Marseille

Real Arab Lesbian Pussy Licking In Marseille

XHamster 3 years ago

April's Sissy Program: 6 - Fucked

April's Sissy Program: 6 - Fucked

Clips4sale 2 years ago

Sissy Task: Work Slut

HD 0:10 / 10:35

Sissy Task: Work Slut

LoyalFans 11 months ago

Over the Knee Spanks and Milking

HD 0:10 / 22:55

Over the Knee Spanks and Milking

LoyalFans 9 months ago

Crossdressing Husband, Caught and Fucked! mp4

72% HD 0:49 / 11:36

Crossdressing Husband, Caught and Fucked! mp4

Clips4sale 2 years ago

Worship of the Firm Butt

57% HD 0:10 / 3:40

Worship of the Firm Butt

LoyalFans 5 months ago

Queen Melanin Power Pegging Returns Full Clip

Queen Melanin Power Pegging Returns Full Clip

LoyalFans 1 year ago

Hot Tub Domination - 720HD

67% 0:14 / 8:31

Hot Tub Domination - 720HD

Clips4sale 3 years ago

Queen Melanin Takes the Strapon to Hoodbitch

61% HD 0:10 / 10:11

Queen Melanin Takes the Strapon to Hoodbitch

LoyalFans 11 months ago

Sissy Slave For Goddess

4K 0:18 / 12:55

Sissy Slave For Goddess

Clips4sale 1 year ago

wife makes you her MTF sissy slut camwhore & lesbian lover

50% HD 0:10 / 17:29

wife makes you her MTF sissy slut camwhore & lesbian lover

LoyalFans 2 years ago

SISSY LOCKTOBER TASK #3 - Mistress Raven gives you a sissy slut task while you’re little clitty is caged up for Locktober - Sissy Training, Sissy Slut, Locktober, Chastity, Task

SISSY LOCKTOBER TASK #3 - Mistress Raven gives you a sissy slut task while you’re little clitty is caged up for Locktober - Sissy Training, Sissy Slut, Locktober, Chastity, Task

Clips4sale 1 year ago

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