Sissy Dress Up (5,881)

The best and newest sissy dress up videos

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

70% HD 1:01 / 5:45

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

FapHouse 5 months ago

Sissy Spanked and Caged by MILF Boss

Sissy Spanked and Caged by MILF Boss

XHamster 1 month ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 3 months ago

NEW - Training You to Suck Cock So I Can Whore You Out, Phillip

71% HD 0:10 / 9:20

NEW - Training You to Suck Cock So I Can Whore You Out, Phillip

LoyalFans 2 months ago

NEW - Witch Reads Your Mind and Discovers You're a Secret Sissy

61% HD 0:10 / 8:56

NEW - Witch Reads Your Mind and Discovers You're a Secret Sissy

LoyalFans 6 months ago

SISSY DRESS UP

64% 0:30 / 9:04

Clips4sale 1 year ago

I want to make you my satin slut sissy

55% 0:19 / 22:49

I want to make you my satin slut sissy

Clips4sale 1 year ago

Humiliating Tasks for Diaper Sissies! POV Instructions

73% HD 0:51 / 16:14

Humiliating Tasks for Diaper Sissies! POV Instructions

Clips4sale 11 months ago

Sissified and pegged - Ebony Goddess Luna Law humiliates, teases and turns this chastity slave into a sissy slut, takes pictures of her and gives her a hot pegging ounding against the window, Female Domination, Sissy Slut training, Strap-on

HD 0:17 / 13:16

Sissified and pegged - Ebony Goddess Luna Law humiliates, teases and turns this chastity slave into a sissy slut, takes pictures of her and gives her a hot pegging ounding against the window, Female Domination, Sissy Slut training, Strap-on

Clips4sale 4 weeks ago

Sissy Date Night

53% 1:01 / 19:30

Sissy Date Night

FapHouse 3 months ago

INEEDAMOMMY IPOD Gentle GF Sushii turns you into slutty diaper girl

INEEDAMOMMY IPOD Gentle GF Sushii turns you into slutty diaper girl

Clips4sale 4 years ago

From Ugly Boy to Pretty Girl: A Total Sissy Transformation

54% HD 0:10 / 34:44

From Ugly Boy to Pretty Girl: A Total Sissy Transformation

LoyalFans 3 months ago

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

XHamster 7 months ago

The Mean Mistress

66% HD 0:10 / 5:40

The Mean Mistress

LoyalFans 1 year ago

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

Lesbian8 1 year ago

Femboy and Vilu Vidish Compilation

51% HD 0:39 / 1:05:58

Femboy and Vilu Vidish Compilation

FapHouse 4 months ago

Sissy husbands part 1 with Lady Phoenix

63% 0:29 / 15:45

Sissy husbands part 1 with Lady Phoenix

Clips4sale 3 years ago

Prissy sissy dolly - Maid to be used

62% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years ago

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

54% 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

POV Cuckold volume 60

POV Cuckold volume 60

XHamster 3 months ago

Rosies Sissification

60% HD 1:01 / 11:09

Rosies Sissification

FapHouse 1 year ago

You are going to be my new sissy boy slut

You are going to be my new sissy boy slut

XHamster 11 years ago

Lily’s Sissy - Feminization Training & Deepthroat Session

HD 0:39 / 11:18

Lily’s Sissy - Feminization Training & Deepthroat Session

Clips4sale 4 months ago

OTK for the Sissy Maid (WL1790)

64% HD 0:10 / 22:23

OTK for the Sissy Maid (WL1790)

LoyalFans 5 months ago

Sissified by Step-Mommy

66% HD 0:15 / 13:28

Sissified by Step-Mommy

IWantClips 4 months ago

Sissy Caption Story: Only the 1st round

Sissy Caption Story: Only the 1st round

Eporner 1 year ago

Gender Transformation Wish Granted Turned into a Woman- MtF - Magic - Fairy - Wish - Male to Female - Tied Up - Gender Bender

63% HD 0:25 / 23:53

Gender Transformation Wish Granted Turned into a Woman- MtF - Magic - Fairy - Wish - Male to Female - Tied Up - Gender Bender

Clips4sale 4 months ago

Cucky Limo

HD 0:24 / 15:05

IWantClips 4 months ago

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

67% HD 0:29 / 6:13

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

IWantClips 4 months ago

Brand Recent World Order

PornFreeNow 3 weeks ago

Cum Like a Girl - Feminized for a Girls Only JOI

52% 4K 0:29 / 20:17

Cum Like a Girl - Feminized for a Girls Only JOI

Clips4sale 1 year ago

Katie Morgan cuckold hardcore

Katie Morgan cuckold hardcore

XHamster 1 month ago

Spanksgiving With The Family

69% 4K 1:56 / 36:00

Spanksgiving With The Family

TeamSkeet 9 years ago

Sissy choked pink cum drenched by femdom goddess

Sissy choked pink cum drenched by femdom goddess

AveXXX 1 month ago

Vivienne L'amour - Transforming You Into My Perfect Sissy Slut

Vivienne L'amour - Transforming You Into My Perfect Sissy Slut

XHamster 1 month ago

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

XHamster 9 months ago

Boyfriend to Girlfriend Pt. 2: Sissified

54% HD 1:01 / 13:47

Boyfriend to Girlfriend Pt. 2: Sissified

FapHouse 5 years ago

Mistress Sophia Sahara & Obey Angelina: Part 2 Strap on Party - slaves get fucked!

64% 0:25 / 41:30

Mistress Sophia Sahara & Obey Angelina: Part 2 Strap on Party - slaves get fucked!

Clips4sale 4 years ago

Mature MILF Try On Haul From Demure to Red Hot Dresses

Mature MILF Try On Haul From Demure to Red Hot Dresses

XHamster 1 year ago

No More Man! - Goddess Amber

69% HD 0:10 / 11:50

No More Man! - Goddess Amber

LoyalFans 1 year ago

Making You My Sissy Fem Boi! (1080p)

56% HD 0:11 / 11:19

Making You My Sissy Fem Boi! (1080p)

Clips4sale 2 years ago

Sissy bride chastity- Wedding night tease

65% HD 0:15 / 12:31

Sissy bride chastity- Wedding night tease

IWantClips 2 years ago

Lingerie Lover - Sissy Pegging POV

51% HD 0:39 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 1 year ago

Your Bully Bimbotized Us

56% 4K 1:00 / 25:12

Your Bully Bimbotized Us

Clips4sale 2 years ago

Nurse Ruby's Monthly Milking: Chastity Patient Drained, & Locked in Inverted Cage

58% HD 0:39 / 12:34

Nurse Ruby's Monthly Milking: Chastity Patient Drained, & Locked in Inverted Cage

FapHouse 1 month ago

Misty Sissy

Some.Porn 1 year ago

Sissy Faggot Feminization Mega Pack!

59% HD 0:25 / 1:37:32

Sissy Faggot Feminization Mega Pack!

IWantClips 2 years ago

Cum play in my garden

Cum play in my garden

Some.Porn 2 years ago

Mistresse craves to suit u up like her fucktoy and assist u educate with a belt-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistresse craves to suit u up like her fucktoy and assist u educate with a belt-on (FEMINIZATION ROLEPLAY - AI GENERATED)

SortPorn 1 year ago

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

64% HD 0:10 / 9:57

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

LoyalFans 1 year ago

Male to Feminized Sissy Bondage Transformation

59% 0:12 / 12:32

Male to Feminized Sissy Bondage Transformation

Clips4sale 2 years ago

Romantic Evening Nylon Sex in White Lingerie

Romantic Evening Nylon Sex in White Lingerie

XHamster 4 years ago

NYMPHO GIRL TEASE AND DENIAL HANDJOB FOOTJOB - smartphone version

76% HD 1:00 / 18:25

NYMPHO GIRL TEASE AND DENIAL HANDJOB FOOTJOB - smartphone version

Clips4sale 2 years ago

Pbp 2 Blue Balls - CBT and Dildo Sucking by Mistress Jennifer

Pbp 2 Blue Balls - CBT and Dildo Sucking by Mistress Jennifer

XHamster 1 week ago

JOI Echo With My Big Black Dick - Luna Doll

JOI Echo With My Big Black Dick - Luna Doll

XHamster 1 year ago

Dress Up With Step-Mommy-4K

4K 0:29 / 13:58

Dress Up With Step-Mommy-4K

Clips4sale 3 years ago

Shirt and jeans removal sex with with hand tied up and hot fuck with desi step sister

Shirt and jeans removal sex with with hand tied up and hot fuck with desi step sister

XHamster 1 year ago

Pbp 2 Blue Balls - CBT and Dildo Sucking by Mistress Jennifer

HD 0:39 / 10:06

Pbp 2 Blue Balls - CBT and Dildo Sucking by Mistress Jennifer

FapHouse 1 month ago

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

68% HD 1:01 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 4 months ago

Long Minet and Creampie In Black Nylon Lingerie

Long Minet and Creampie In Black Nylon Lingerie

XHamster 4 years ago

Horny redhead tempts driver with sex for taxi fare

Horny redhead tempts driver with sex for taxi fare

Some.Porn 2 years ago

Blonde Teen and Black Bull

Blonde Teen and Black Bull

Some.Porn 2 years ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 3 years ago

Girls Night Out

Girls Night Out

XHamster 7 months ago

Cheerleader Try Out

HD 1:01 / 20:52

Cheerleader Try Out

FapHouse 1 month ago

Slutty Bitch - Anal Treatment

HD 1:01 / 12:51

Slutty Bitch - Anal Treatment

FapHouse 2 weeks ago

Borrow My Sissy Boyfriend

67% 0:12 / 25:44

Borrow My Sissy Boyfriend

AdultPrime 8 years ago

FULL SERVICE FROM SISSY BITCH: Milking, Pegging & Mouth Fucking 4k MahoganyQen

4K 0:10 / 34:02

FULL SERVICE FROM SISSY BITCH: Milking, Pegging & Mouth Fucking 4k MahoganyQen

LoyalFans 1 month ago

Milking the Sissy

Milking the Sissy

XHamster 7 months ago

Simply Sensual Evening Sex in Vintage Lingerie Ended with Bukkake

Simply Sensual Evening Sex in Vintage Lingerie Ended with Bukkake

XHamster 3 years ago

amber blank - bi cuck sissy

amber blank - bi cuck sissy

PornOne 6 years ago

Dressing up Sissy

54% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Becoming a sissy

Becoming a sissy

FreePorn8 6 years ago

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

50% HD 1:01 / 22:02

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

FapHouse 2 years ago

Sissy cuckold in chastity sharing his wife. Cuckold confession with Adreena Winters

63% HD 0:31 / 35:47

Sissy cuckold in chastity sharing his wife. Cuckold confession with Adreena Winters

IWantClips 4 months ago

You Bet Your Ass

52% HD 0:10 / 29:22

You Bet Your Ass

LoyalFans 1 year ago

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

50% HD 0:10 / 6:13

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

LoyalFans 5 months ago

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

XHamster 2 years ago

Petite Ma'am fucking her pink sissy maid in chastity

Petite Ma'am fucking her pink sissy maid in chastity

XHamster 3 years ago

Best of Sissy Slut Pegging: Strapon Fucking Compilation

Best of Sissy Slut Pegging: Strapon Fucking Compilation

XHamster 2 years ago

Your Sissy Dream

Your Sissy Dream

FapHouse 10 months ago

Made into My Sissy Maid

57% 4K 0:25 / 14:51

Made into My Sissy Maid

Clips4sale 3 weeks ago

Sissy Gamer Gurl: Femdom Pegging & Deep Fisting Full-length (1080p)

HD 0:39 / 36:39

Sissy Gamer Gurl: Femdom Pegging & Deep Fisting Full-length (1080p)

FapHouse 2 months ago

BBW PAWG Paige Turnah British pornstar femdom sissy slave play dress up

BBW PAWG Paige Turnah British pornstar femdom sissy slave play dress up

XHamster 2 years ago

SISSY COCKSUCKING LESSONS feat ASTRODOMINA

HD 0:17 / 11:17

SISSY COCKSUCKING LESSONS feat ASTRODOMINA

IWantClips 2 years ago

Fist and shout fisting my man fast

Fist and shout fisting my man fast

XHamster 2 years ago

Horny Thief Gets Pumped

Horny Thief Gets Pumped

Some.Porn 10 months ago

you in My nightgown

56% HD 0:15 / 8:54

you in My nightgown

IWantClips 4 months ago

Sissy Spanked and Caged by MILF Boss

Sissy Spanked and Caged by MILF Boss

XHamster 1 month ago

Making Him My Sissy Slut! Caged and Fucked

Making Him My Sissy Slut! Caged and Fucked

XHamster 3 weeks ago

Sissy Phoenix Marie fills Aubrey Kate's mouth with cum

Sissy Phoenix Marie fills Aubrey Kate's mouth with cum

MegaTube 5 years ago

Making My Husband into a Cuckold Sissy!

50% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 3 years ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

XHamster 3 months ago

Panties and Orgasm for My Good Little Sissy

57% 0:30 / 9:08

Panties and Orgasm for My Good Little Sissy

Clips 1 month ago

WIFE'S REALISTIC CONFESSION PART 10 feat ASTRODOMINA

65% HD 0:15 / 22:09

WIFE'S REALISTIC CONFESSION PART 10 feat ASTRODOMINA

IWantClips 5 years ago

Sissy French Maid Ria Bentley Gives Service To BBC Hotel Guest

52% HD 0:10 / 18:13

Sissy French Maid Ria Bentley Gives Service To BBC Hotel Guest

LoyalFans 1 year ago

Compilation of tied up man getting fisted and pegged

Compilation of tied up man getting fisted and pegged

XGroovy 2 years ago

Sissy Date Night

47% HD 0:10 / 9:35

Sissy Date Night

LoyalFans 10 months ago

Sissy Boyfriend Found Out and Pegged

60% HD 0:10 / 18:38

Sissy Boyfriend Found Out and Pegged

LoyalFans 3 years ago

Chubby Mistress bends Him over to grab His balls and gives a rough Handjob

Chubby Mistress bends Him over to grab His balls and gives a rough Handjob

PornFreeNow 1 year ago

NEW CONTENT! The Training Of Sissy Cum Bucket By Ruby Onyx

72% 4K 0:38 / 13:23

NEW CONTENT! The Training Of Sissy Cum Bucket By Ruby Onyx

Clips4sale 1 year ago

Humiliating the sissy slut

56% HD 0:10 / 21:30

Humiliating the sissy slut

LoyalFans 4 months ago

Sissy slut exposed by aunt | Evilwoman

HD 0:10 / 13:05

Sissy slut exposed by aunt | Evilwoman

LoyalFans 1 week ago

POV Cuckold volume 60

POV Cuckold volume 60

SortPorn 3 months ago

POV: Caught Watching Like a Pathetic Cuck, Now Take Your Strap-on Humiliation

65% 0:39 / 12:07

POV: Caught Watching Like a Pathetic Cuck, Now Take Your Strap-on Humiliation

FapHouse 3 weeks ago

Making My Yard Man Sissy Slave Part 2

Making My Yard Man Sissy Slave Part 2

XHamster 6 months ago

Full Sissy Transformation - Cage, Dress & Daily Rules

57% 0:29 / 7:06

Full Sissy Transformation - Cage, Dress & Daily Rules

Clips4sale 6 months ago

The making of sissy Sally

61% HD 0:19 / 12:29

The making of sissy Sally

QueensOfKink 1 year ago

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

66% HD 1:01 / 10:53

Cucked & Feminized by a Hot Alpha Couple Sissy Humiliation Fantasy

FapHouse 7 months ago

CLOSETED SISSY HUSBAND - HIS SECRET IS OUT! - PART 2 - ANAL PLAY & FIRST PEGGING

HD 0:10 / 21:57

CLOSETED SISSY HUSBAND - HIS SECRET IS OUT! - PART 2 - ANAL PLAY & FIRST PEGGING

LoyalFans 5 days ago

Slutty Bitch - Anal Treatment

Slutty Bitch - Anal Treatment

XHamster 1 week ago

Inhale and Take It Deep: Step-Mommy's Sissy Training

HD 0:10 / 34:45

Inhale and Take It Deep: Step-Mommy's Sissy Training

LoyalFans 1 week ago

Closeted Sissy Husband — His Secret Is Out! - PART 1 - Spanking & Submission - 4K

4K 0:10 / 16:32

Closeted Sissy Husband — His Secret Is Out! - PART 1 - Spanking & Submission - 4K

LoyalFans 1 week ago

1st Sissy Experience With Miss Shell

56% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 6 months ago

Turning You Into My Sissy Slut

Turning You Into My Sissy Slut

XHamster 2 months ago

Cum lipgloss

HD 0:39 / 10:30

FapHouse 5 years ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

59% HD 0:39 / 16:47

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

FapHouse 3 months ago

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

67% HD 0:38 / 15:41

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

Clips4sale 1 year ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

65% HD 1:01 / 16:47

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

FapHouse 3 months ago

Dildo Dolly 2

53% HD 1:01 / 15:31

FapHouse 3 years ago

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