Sissy Dress Up (1,834)

Astolfo Takes a Pounding - Cosplay

Astolfo Takes a Pounding - Cosplay

XHamster 2 months ago

Sissy Terms and Conditions

Sissy Terms and Conditions

XHamster 3 months ago

Sissy Slut Examination by a Surprise Latex Doctor

69% HD 0:10 / 25:33

Sissy Slut Examination by a Surprise Latex Doctor

LoyalFans 7 months ago

Ultimate Sissy Transformation Nikki

65% HD 0:20 / 17:24

Ultimate Sissy Transformation Nikki

IWantClips 2 years ago

I Dressed up as a Woman, Put on Makeup, How Do You Like It?

I Dressed up as a Woman, Put on Makeup, How Do You Like It?

XHamster 3 months ago

Extreme Boot Slut Stage 1

HD 0:10 / 10:02

Extreme Boot Slut Stage 1

LoyalFans 1 week ago

You're Such a Sexy Sissy Slut for Me

You're Such a Sexy Sissy Slut for Me

XHamster 3 weeks ago

Fucking Crossdressers is GAY!

61% HD 0:10 / 11:37

Fucking Crossdressers is GAY!

LoyalFans 3 years ago

Nylon Trans Slut fucks BBC, surrenders Huge Cum load

59% HD 0:10 / 14:47

Nylon Trans Slut fucks BBC, surrenders Huge Cum load

LoyalFans 3 months ago

Crossdressing Sissy Fag Slut Wants a Daddy

Crossdressing Sissy Fag Slut Wants a Daddy

XHamster 5 months ago

Feminizing and Face Fucking a Sissy || TS Karabella

67% HD 0:10 / 23:48

Feminizing and Face Fucking a Sissy || TS Karabella

LoyalFans 5 months ago

COCK FILLED WHORE (1080p)

67% HD 0:22 / 12:23

COCK FILLED WHORE (1080p)

Clips4sale 1 year ago

Bisexual Sissy Domination

56% HD 0:10 / 19:46

Bisexual Sissy Domination

LoyalFans 2 months ago

I Dressed up as a Woman, Put on Makeup, How Do You Like It?

I Dressed up as a Woman, Put on Makeup, How Do You Like It?

XHamster 2 months ago

- Rubbing My Feet

- Rubbing My Feet

XHamster 5 months ago

Sissy Humiliation Dare Game

Sissy Humiliation Dare Game

XHamster 8 months ago

Young Feminine Boy Drssed up a Woman Dress off White Big Booty Smooth Feminine Skin

Young Feminine Boy Drssed up a Woman Dress off White Big Booty Smooth Feminine Skin

FapHouse 7 months ago

Sissy Dreams (9 inches of uncut dreams) audio only Encouragement

55% 0:30 / 5:53

Sissy Dreams (9 inches of uncut dreams) audio only Encouragement

Clips4sale 1 year ago

You're Such a Sexy Sissy Slut for Me

You're Such a Sexy Sissy Slut for Me

XHamster 3 weeks ago

The Gay Awakening Podcast Episode #35

71% HD 0:20 / 10:49

The Gay Awakening Podcast Episode #35

Clips4sale 3 years ago

Sissy Hubby in Chastity Trained to Suck Cock (WL1759)

68% HD 0:10 / 17:41

Sissy Hubby in Chastity Trained to Suck Cock (WL1759)

LoyalFans 3 months ago

Sissy Slut For Goddess Mandy

62% HD 0:29 / 13:36

Sissy Slut For Goddess Mandy

Clips4sale 2 years ago

You're a Sissy Faggot Whore

You're a Sissy Faggot Whore

Clips4sale 4 years ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

XHamster 2 years ago

Sissy JOI Gooning in Chastity

HD 0:30 / 12:10

Sissy JOI Gooning in Chastity

Clips4sale 2 years ago

You Can't Stop Your Sissy Urges

66% 0:11 / 7:11

You Can't Stop Your Sissy Urges

Clips4sale 3 years ago

Inhale & Let Step-Mommy & Her Boyfriend Use You

HD 0:30 / 23:43

Inhale & Let Step-Mommy & Her Boyfriend Use You

Clips4sale 9 months ago

Dressed Up And Bullied

46% HD 0:10 / 13:38

Dressed Up And Bullied

LoyalFans 2 years ago

Naughty patient Katja (diaper pee, milking and cumshot)

70% HD 0:11 / 25:59

Naughty patient Katja (diaper pee, milking and cumshot)

Clips4sale 4 years ago

You failed as man now look at you loser sissy white extinction (1080HD)

HD 0:28 / 14:59

You failed as man now look at you loser sissy white extinction (1080HD)

Clips4sale 4 years ago

Bella's Femboy Confession (Big Cumshot)

59% HD 0:10 / 8:55

Bella's Femboy Confession (Big Cumshot)

Clips4sale 4 years ago

Sissy MTF Sexy Wench 2 Lewd Dresses Performing White Twink Princess Crossdresser Kitty

Sissy MTF Sexy Wench 2 Lewd Dresses Performing White Twink Princess Crossdresser Kitty

ShemaleSin 1 year ago

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

50% HD 0:30 / 27:46

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

Clips4sale 1 year ago

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

72% HD 0:30 / 5:40

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

Clips4sale 2 years ago

Auntie's Summer Sissy

Auntie's Summer Sissy

XHamster 5 months ago

sexy femboi gets an injection of Americana

60% 0:30 / 23:08

sexy femboi gets an injection of Americana

Clips4sale 1 year ago

Dress Up Group Breeding

61% HD 0:27 / 17:53

Dress Up Group Breeding

Clips4sale 11 months ago

First Time Feminization With A New Pegging Slut

48% HD 0:10 / 25:18

First Time Feminization With A New Pegging Slut

LoyalFans 3 years ago

I'll Make You My Perfect Sissy Girlfriend

I'll Make You My Perfect Sissy Girlfriend

Clips4sale 2 years ago

Teasing Sissy Hard

Teasing Sissy Hard

Clips4sale 2 years ago

Husband dressed up like a sissy bitch & pegged in his tight ass hole

Husband dressed up like a sissy bitch & pegged in his tight ass hole

XHamster 3 years ago

Ts Isa Oliveira dominates Hex in a BDSM Sissification Session (720p ENG-sub) Trans Woman - Trans Dominatrix - Trans Fucking - Trans Blowjob - Trans Cock Sucker - Trans Anal Domination

HD 0:28 / 25:13

Ts Isa Oliveira dominates Hex in a BDSM Sissification Session (720p ENG-sub) Trans Woman - Trans Dominatrix - Trans Fucking - Trans Blowjob - Trans Cock Sucker - Trans Anal Domination

Clips4sale 7 months ago

Trapped as a Sissy Stripper

Trapped as a Sissy Stripper

XHamster 7 months ago

My Sissy Best Friend

My Sissy Best Friend

Clips4sale 3 years ago

Secret Video Call with Satin Secretary

Secret Video Call with Satin Secretary

Clips4sale 1 year ago

Sissy bride chastity - Wedding night tease

50% 0:11 / 12:31

Sissy bride chastity - Wedding night tease

Clips4sale 2 years ago

Sissy Wife Panty Wearing CEI JOI

HD 0:10 / 14:35

Sissy Wife Panty Wearing CEI JOI

LoyalFans 3 months ago

My Dress-Up Darling, Rizu-kyun cosplayer get fucked with sex toy, anime cosplay Clip 1

My Dress-Up Darling, Rizu-kyun cosplayer get fucked with sex toy, anime cosplay Clip 1

XHamster 10 months ago

Crazy Futa Clown Posse

63% 0:30 / 10:00

Crazy Futa Clown Posse

Clips4sale 10 months ago

Sissy Slut Examination by a Surprise Latex Doctor

44% HD 0:10 / 25:33

Sissy Slut Examination by a Surprise Latex Doctor

LoyalFans 7 months ago

Sexy Succubus cosplayer Blowjob and get fucked, My Dress-Up Darling Rizu-kyun blowjob part.8

Sexy Succubus cosplayer Blowjob and get fucked, My Dress-Up Darling Rizu-kyun blowjob part.8

XHamster 3 years ago

Sissy Homewrecking JOI

HD 0:25 / 11:10

Sissy Homewrecking JOI

IWantClips 5 years ago

Stepmother in lingerie Trims Horny hairy cock of Kneeling Crossdresser in Stockings - Humiliation Conversations a Slut, Amateur Couple Home Video, Bisexual Encouragement, Close Female Naked Male, Femdom, Gentle Discipline

50% 4K 0:23 / 11:38

Stepmother in lingerie Trims Horny hairy cock of Kneeling Crossdresser in Stockings - Humiliation Conversations a Slut, Amateur Couple Home Video, Bisexual Encouragement, Close Female Naked Male, Femdom, Gentle Discipline

Clips4sale 7 months ago

Rub Your Sissy Clitty for Mistress

63% 0:11 / 7:44

Rub Your Sissy Clitty for Mistress

Clips4sale 3 years ago

Convincing You To Become A Controlled Sissy-Girl (4KUHD MP4)

53% HD 0:31 / 14:50

Convincing You To Become A Controlled Sissy-Girl (4KUHD MP4)

Clips4sale 2 years ago

Crossdressing Sissy Humiliation with Katie Katt - MP4 (HD 1080p)

58% HD 0:23 / 6:04

Crossdressing Sissy Humiliation with Katie Katt - MP4 (HD 1080p)

Clips4sale 1 year ago

Horny Sissy For Halloween - Extended Preview

Horny Sissy For Halloween - Extended Preview

XHamster 2 years ago

Bimbo Training with Maya Sinstress: Slut Maxxxing

HD 0:10 / 16:37

Bimbo Training with Maya Sinstress: Slut Maxxxing

LoyalFans 2 days ago

You're a snow sissy now

You're a snow sissy now

IWantClips 4 years ago

Neon Pink Sissy Slut Dress Up

Neon Pink Sissy Slut Dress Up

Clips4sale 1 year ago

A Very Sissy Valentine's

65% HD 0:29 / 14:53

A Very Sissy Valentine's

Clips4sale 3 years ago

Latex Femboy Cums While Gagged and Masked

53% HD 0:13 / 10:13

Latex Femboy Cums While Gagged and Masked

Clips4sale 4 years ago

Transforming you into my girlfriend - Miss Honour May - MP4 HD

55% HD 0:16 / 13:24

Transforming you into my girlfriend - Miss Honour May - MP4 HD

Clips4sale 2 years ago

Nylon Sissy Slave - Candle Boxxx HDMP4

39% 0:14 / 13:03

Nylon Sissy Slave - Candle Boxxx HDMP4

Clips4sale 2 years ago

Jessica Kat's Private Lesson

50% 0:33 / 18:48

Jessica Kat's Private Lesson

Clips4sale 5 years ago

Fuckmachine and Strapon DP for Sissy

65% HD 0:10 / 5:25

Fuckmachine and Strapon DP for Sissy

LoyalFans 3 years ago

Sissy Play Time - Dressing You Up To Look Your Sissy Best, Then Making You Practice Sucking Cock on a Dildo

70% 0:30 / 7:48

Sissy Play Time - Dressing You Up To Look Your Sissy Best, Then Making You Practice Sucking Cock on a Dildo

Clips4sale 1 year ago

Sissy Wife Eats My Bull's Cum Out of My Panties

HD 0:10 / 11:29

Sissy Wife Eats My Bull's Cum Out of My Panties

LoyalFans 2 months ago

Sissy cuck caught in hotel

53% 0:30 / 34:20

Sissy cuck caught in hotel

Clips4sale 1 year ago

Just Another Incredibly Hot Day

Just Another Incredibly Hot Day

XHamster 3 weeks ago

Bitch boi dressed in fishnets & his pathetic ass hole fucked by his mistress

Bitch boi dressed in fishnets & his pathetic ass hole fucked by his mistress

XHamster 3 years ago

PREMATURE EJACULATION TO CLEAVAGE FOR A SISSY CROSSDRESSER 1080P

65% HD 0:10 / 7:46

PREMATURE EJACULATION TO CLEAVAGE FOR A SISSY CROSSDRESSER 1080P

LoyalFans 9 months ago

Dressed Up And Bullied

39% 0:35 / 13:37

Dressed Up And Bullied

Clips4sale 2 years ago

Permanent Punisher

66% 0:06 / 8:14

Permanent Punisher

Clips4sale 9 months ago

Femboy Craves CBT Punishment

69% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

LADY SCARLET - NYLON TRAP hd

Premium HD 25:42

LADY SCARLET - NYLON TRAP hd

Clips4sale 2 years ago

Gang Bang Sissy Spit Roast (720p)

59% HD 0:30 / 10:37

Gang Bang Sissy Spit Roast (720p)

Clips4sale 1 year ago

Mistress in latex Gloves Shaving Hairy Cock of Submissive Sissy Slut in nylon Stockings - Feminization of the Straight Man, Sissy Slut Doggystyle with Hairy Ass, Mistress Tease Horny Dick, Home Barbershop 4k

4K 0:23 / 11:38

Mistress in latex Gloves Shaving Hairy Cock of Submissive Sissy Slut in nylon Stockings - Feminization of the Straight Man, Sissy Slut Doggystyle with Hairy Ass, Mistress Tease Horny Dick, Home Barbershop 4k

Clips4sale 7 months ago

Tranny has cumshot with vibro toy in public! Full load of sperm in her pants!

63% HD 0:23 / 6:05

Tranny has cumshot with vibro toy in public! Full load of sperm in her pants!

Clips4sale 2 years ago

Pathetic Sissy Faggot

61% 0:11 / 14:17

Pathetic Sissy Faggot

Clips4sale 3 years ago

Sissification Fashion Show After Party Makeover by Bellatrix Bandit

59% 0:15 / 23:33

Sissification Fashion Show After Party Makeover by Bellatrix Bandit

Clips4sale 5 years ago

horny elegant skinny lady milf with big dick jerk off and cum huge load

horny elegant skinny lady milf with big dick jerk off and cum huge load

XHamster 3 years ago

I'm so good he cums twice

80% HD 0:43 / 6:24

I'm so good he cums twice

Clips4sale 1 year ago

Trucker step-Daddy Loves Diaper Sissy

51% HD 0:10 / 27:41

Trucker step-Daddy Loves Diaper Sissy

LoyalFans 10 months ago

Femization Lesson POV Femdom with Madame Juliette

53% 0:12 / 10:04

Femization Lesson POV Femdom with Madame Juliette

Clips4sale 3 years ago

Sissified at the mall MP4

HD 0:26 / 11:59

Sissified at the mall MP4

Clips4sale 1 year ago

LADY SCARLET - NYLON, ROPES AND FILM FOR MY SISSIES mobile

63% HD 0:41 / 26:52

LADY SCARLET - NYLON, ROPES AND FILM FOR MY SISSIES mobile

Clips4sale 1 year ago

How to become a slutty Sissy Bitch *HD*

How to become a slutty Sissy Bitch *HD*

Clips4sale 1 year ago

Sissy Can Play While Wifeys Away

56% HD 0:29 / 10:42

Sissy Can Play While Wifeys Away

Clips4sale 4 years ago

Sissy Slut Dress up and Pegging Playtime

Premium 4K 24:22

Sissy Slut Dress up and Pegging Playtime

Clips4sale 2 weeks ago

Sissy Porn Warped Your Brain

Sissy Porn Warped Your Brain

Clips4sale 2 years ago

Tranny Helenas new fucking machine! First test with mega Cumshot!

HD 0:30 / 11:17

Tranny Helenas new fucking machine! First test with mega Cumshot!

Clips4sale 3 years ago

LEATHER DADDIES 1

68% 0:30 / 5:51

LEATHER DADDIES 1

Clips4sale 4 years ago

Drip In Your Panties

Drip In Your Panties

IWantClips 2 months ago

Step-Mommys Surgical Secret- From SPH to Sissification

HD 0:10 / 10:52

Step-Mommys Surgical Secret- From SPH to Sissification

LoyalFans 2 weeks ago

Sissy Pride: Bitch in Heat, Pride in Knees -SISSIFICATION, TASK

68% HD 0:10 / 10:21

Sissy Pride: Bitch in Heat, Pride in Knees -SISSIFICATION, TASK

LoyalFans 1 year ago

Cummy Classroom Sissy Slut Tgirl Panty Loads

58% 0:11 / 14:08

Cummy Classroom Sissy Slut Tgirl Panty Loads

Clips4sale 3 years ago

making you my bf's fucktoy - sissification, anal, imposed bi - full video on Veggiebabyy Manyvids

making you my bf's fucktoy - sissification, anal, imposed bi - full video on Veggiebabyy Manyvids

XHamster 2 years ago

SISSY SLUT BLACKED IN THE ALLEY - PART 1

57% HD 0:10 / 17:41

SISSY SLUT BLACKED IN THE ALLEY - PART 1

LoyalFans 2 years ago

Sissy Dream Date

HD 0:29 / 15:21

Sissy Dream Date

Clips4sale 4 years ago

Kinky Bitch - sissy training part 1

68% 4K 0:43 / 12:10

Kinky Bitch - sissy training part 1

Clips4sale 4 months ago

Pinky Pinky Feminisation - part 2

65% HD 0:27 / 10:18

Pinky Pinky Feminisation - part 2

Clips4sale 1 year ago

Ai Salon Sucker

55% HD 0:10 / 7:18

Ai Salon Sucker

LoyalFans 3 years ago

Wife Sissifies You - Sissy Training with Rebelle Hart

52% 0:25 / 16:59

Wife Sissifies You - Sissy Training with Rebelle Hart

Clips4sale 1 year ago

Be a pretty little sissy for Satan - SISSIFICATION, CROSS DRESSING, PUBLIC TASK

66% HD 0:10 / 9:15

Be a pretty little sissy for Satan - SISSIFICATION, CROSS DRESSING, PUBLIC TASK

LoyalFans 6 months ago

My Dress-Up Darling, Rizu-kyun cosplayer get fucked with sex toy, anime cosplay part.10

My Dress-Up Darling, Rizu-kyun cosplayer get fucked with sex toy, anime cosplay part.10

XHamster 3 years ago

Sissy Makeover by your TS StepMom

Sissy Makeover by your TS StepMom

AShemaleTube 1 year ago

Big Cock stepMommy Turns You Sissy - hd mp4

41% HD 0:30 / 13:00

Big Cock stepMommy Turns You Sissy - hd mp4

Clips4sale 4 years ago

Say Super-Gay Things Until You Sissygasm (4KUHD MP4)

63% HD 0:30 / 15:09

Say Super-Gay Things Until You Sissygasm (4KUHD MP4)

Clips4sale 2 years ago

Large White Sissy Booty Crossdresser Wench Twink Homosexual Fem Male Lady Hunk Alt Style Flowered Hawt Suit

Large White Sissy Booty Crossdresser Wench Twink Homosexual Fem Male Lady Hunk Alt Style Flowered Hawt Suit

ShemaleSin 8 months ago

GAY FOR PAY

55% 0:08 / 12:03

Clips4sale 3 years ago

horny shemale glamour red dress black gloves bick dick cumshot

horny shemale glamour red dress black gloves bick dick cumshot

XHamster 3 years ago

Sissy Humiliation Dare Game

Sissy Humiliation Dare Game

XHamster 9 months ago

Hard workout for tranny girl! With vibrating butt plug at the gym! FULL CLIP

60% HD 0:30 / 15:18

Hard workout for tranny girl! With vibrating butt plug at the gym! FULL CLIP

Clips4sale 10 months ago

Slutty SISSY CEI

50% HD 0:10 / 7:22

Slutty SISSY CEI

LoyalFans 1 year ago

SISSY SLUT BLACKED IN THE ALLEY - PART 1

4K 0:33 / 17:40

SISSY SLUT BLACKED IN THE ALLEY - PART 1

Clips4sale 2 years ago

Ass to Ass Sissies

58% HD 0:10 / 9:49

Ass to Ass Sissies

LoyalFans 5 months ago

Estrogen Encouragement

Estrogen Encouragement

Clips4sale 1 year ago

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -mobile

66% 0:15 / 19:16

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -mobile

Clips4sale 11 months ago

Transforming you into my girlfriend - Miss Honour May - MP4 SD

41% HD 0:16 / 13:24

Transforming you into my girlfriend - Miss Honour May - MP4 SD

Clips4sale 2 years ago

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1,834 results found

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