Sissy Humiliation Videos (3,662)

Dark cuckolding day with an amazing TRANS Goddess and my slut noun wife Maisa Pravo

74% 4K 0:55 / 25:41

Dark cuckolding day with an amazing TRANS Goddess and my slut noun wife Maisa Pravo

Clips4sale 1 year ago

dominant trans gives cuck bf SPH and makes him cum in cage

63% 4K 0:40 / 14:14

dominant trans gives cuck bf SPH and makes him cum in cage

Clips4sale 11 months 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

Feminized In France (HD MP4)

56% 4K 0:29 / 16:00

Feminized In France (HD MP4)

Clips4sale 2 years ago

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 years ago

SHEMALE TENTACLE INVASION

53% HD 0:15 / 13:25

SHEMALE TENTACLE INVASION

Clips4sale 1 year ago

Giantess Farts on You!

58% 0:29 / 8:09

Giantess Farts on You!

Clips4sale 1 year ago

Sissies Belong In Chastity (SD MP4)

60% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 2 years ago

Sissy Humiliation Diaper Dreams

HD 0:54 / 23:20

Sissy Humiliation Diaper Dreams

Clips4sale 2 months ago

Dressed Up And Bullied

46% HD 0:10 / 13:38

Dressed Up And Bullied

LoyalFans 2 years ago

Dirty Fucking Sissy Faggot

70% HD 0:10 / 36:35

Dirty Fucking Sissy Faggot

LoyalFans 7 months ago

Femdom Stories #10B: My Latex Domme Toy Trials (Animated)

HD 0:25 / 20:12

Femdom Stories #10B: My Latex Domme Toy Trials (Animated)

from cheater to sissy: punishment pegging from futa step-mommy - HD

57% HD 0:28 / 13:08

from cheater to sissy: punishment pegging from futa step-mommy - HD

Clips4sale 3 years ago

Go Gay For My Popularity

45% 0:24 / 7:42

Go Gay For My Popularity

Clips4sale 3 years ago

Boy Dressed like girl Trampled By Blonde Girl

68% 0:30 / 10:43

Boy Dressed like girl Trampled By Blonde Girl

Clips4sale 1 year ago

Fucking Crossdressers is GAY!

61% HD 0:10 / 11:37

Fucking Crossdressers is GAY!

LoyalFans 3 years ago

Closet Faggot Dirty Talk

49% HD 0:11 / 6:35

Closet Faggot Dirty Talk

Clips4sale 4 years ago

SHEMALE SNAKE INVASION

54% HD 0:10 / 13:25

SHEMALE SNAKE INVASION

LoyalFans 1 year ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

LoyalFans 1 year ago

Sarah Gregory Ball Busts Sissy Sabrina Valentine (4K MP4)

Premium 4K 12:40

Sarah Gregory Ball Busts Sissy Sabrina Valentine (4K MP4)

Clips4sale 8 months ago

Sissy Christmas Tree

Sissy Christmas Tree

Clips4sale 9 months ago

TSDemoness Lilith Fucking and Getting Fucked by Guy

HD 0:10 / 24:15

TSDemoness Lilith Fucking and Getting Fucked by Guy

LoyalFans 2 months ago

Sissy Roommate Girly JOI

42% 0:14 / 10:33

Sissy Roommate Girly JOI

Clips4sale 2 years ago

sissy cheerleader fucked by futa domme & the basketball team + ass worship!

60% HD 0:10 / 16:01

sissy cheerleader fucked by futa domme & the basketball team + ass worship!

LoyalFans 1 year ago

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

64% 4K 0:25 / 16:22

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

Clips4sale 11 months ago

Pissy Sissy

65% HD 0:25 / 18:02

Clips4sale 1 year ago

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

57% HD 0:30 / 6:34

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

Clips4sale 3 years ago

Feminizing and Pissing on a Sissy Slut MOV

HD 0:13 / 14:57

Feminizing and Pissing on a Sissy Slut MOV

Clips4sale 4 months ago

femdom tgirl gives SPH and busts whiteboi balls with BBC

67% 0:30 / 17:33

femdom tgirl gives SPH and busts whiteboi balls with BBC

Clips4sale 1 year ago

GLORYHOLE LUNCH BREAK

52% HD 0:10 / 24:59

GLORYHOLE LUNCH BREAK

LoyalFans 3 years ago

Dress Up Sissy Costume Tasks

HD 0:29 / 10:44

Dress Up Sissy Costume Tasks

Clips4sale 11 months ago

No More Masculinity

55% 0:18 / 11:11

No More Masculinity

Clips4sale 2 years ago

Diaper Sissy Circus Freak

HD 0:51 / 16:30

Diaper Sissy Circus Freak

Clips4sale 2 weeks ago

30 Days to Become a Barbie - Sissy Transformation

60% HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation

Clips4sale 2 months ago

Interactive Sissy Quiz - How Big of a Sissy Slut Are You?

HD 1:00 / 13:23

Interactive Sissy Quiz - How Big of a Sissy Slut Are You?

Clips4sale 5 months 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

Slut makeover and anal training

49% HD 0:24 / 9:27

Slut makeover and anal training

Clips4sale 1 year ago

Loser humiliaton by Tranny Dom! Cumshot while Facesit! JOI

55% HD 0:29 / 8:10

Loser humiliaton by Tranny Dom! Cumshot while Facesit! JOI

Clips4sale 3 months ago

Sucking Dick is Good for You

Sucking Dick is Good for You

Clips4sale 3 years ago

LADY YUNA FOOTSTOOL

LADY YUNA FOOTSTOOL

Clips4sale 4 years ago

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

60% HD 0:29 / 23:10

Miss Lilly, the Lady of the Manor, along with Miss Bella Bouvier and Miss Lola Milk, the two devoted governesses, embark on a full makeover sissy transformation of the new boy in the manor. Watch as he begins his journey to become a pretty girl, collared

Clips4sale 8 months ago

Ruined By SheMales

44% HD 0:15 / 7:58

Ruined By SheMales

Clips4sale 2 years ago

Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)

64% HD 0:30 / 9:03

Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)

Clips4sale 2 years ago

PANTYHOSE WEARING SISSY SLUT TRANCE

63% 4K 0:25 / 20:47

PANTYHOSE WEARING SISSY SLUT TRANCE

Clips4sale 3 years ago

Blonde Trans Bimbo TS Natasha Magenta Blowjob and Facial

59% HD 0:27 / 9:25

Blonde Trans Bimbo TS Natasha Magenta Blowjob and Facial

Clips4sale 2 years ago

SAY “I AM A FAGGOT MISTRESS RAVEN”

60% HD 0:10 / 23:45

SAY “I AM A FAGGOT MISTRESS RAVEN”

LoyalFans 3 years ago

Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!

63% HD 0:30 / 19:59

Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!

Clips4sale 1 year ago

Sissy Slave Interview

52% HD 0:24 / 9:32

Sissy Slave Interview

Clips4sale 3 years ago

Maxi Pad Slave Humiliation: Dildo Ass Plug, Pad Gag & Vibrator Tease Through Panties

66% HD 0:30 / 22:31

Maxi Pad Slave Humiliation: Dildo Ass Plug, Pad Gag & Vibrator Tease Through Panties

Clips4sale 8 months ago

Sissy Stroke For Stockings

HD 0:10 / 10:58

Sissy Stroke For Stockings

LoyalFans 1 year ago

Castrate the Sissy

49% HD 0:16 / 9:24

Castrate the Sissy

Clips4sale 1 year ago

Good Girl Fucked, Bad Girl Cucked

69% HD 1:00 / 29:25

Good Girl Fucked, Bad Girl Cucked

Clips4sale 3 years ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

67% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 2 years ago

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Clips4sale 8 months ago

From Roomie to Sissy with Elle Eros and Clara Dee

66% 4K 0:30 / 17:36

From Roomie to Sissy with Elle Eros and Clara Dee

Clips4sale 1 year ago

Sissy in Chastity Fucked Compilation

56% HD 0:10 / 25:35

Sissy in Chastity Fucked Compilation

LoyalFans 1 month ago

Tied-Up Trans Girl Slave smells BBW Domme's Farts

Tied-Up Trans Girl Slave smells BBW Domme's Farts

Clips4sale 1 year ago

I turn my slave into a sissy slut and make him suck a dildo, MF

Premium HD 11:00

I turn my slave into a sissy slut and make him suck a dildo, MF

Clips4sale 1 month ago

hung dominant trans gives bf SPH and ball busting with BBC

73% 0:32 / 16:26

hung dominant trans gives bf SPH and ball busting with BBC

Clips4sale 2 years ago

Prettied Up as a Sissy for Your Date

65% 0:10 / 7:43

Prettied Up as a Sissy for Your Date

Clips4sale 2 years ago

Sissy Bride Wedding Day Part 1 Dressed and Locked

57% 0:11 / 6:14

Sissy Bride Wedding Day Part 1 Dressed and Locked

Clips4sale 3 years ago

Bully Turns You Into A SISSY!

HD 0:10 / 10:07

Bully Turns You Into A SISSY!

LoyalFans 3 months ago

SISSYGASM ENCOURAGEMENT

55% 4K 0:30 / 7:25

SISSYGASM ENCOURAGEMENT

Clips4sale 2 years ago

Caught My Boyfriend Cheating With A Tranny Part 2

54% HD 0:25 / 12:11

Caught My Boyfriend Cheating With A Tranny Part 2

Clips4sale 3 years ago

Helloween filthy BDSM Party - Orgy - Full - FEMDOM - SPH - Tranny - Big Butt - Humiliation - Part 3

4K 0:55 / 17:37

Helloween filthy BDSM Party - Orgy - Full - FEMDOM - SPH - Tranny - Big Butt - Humiliation - Part 3

Clips4sale 11 months ago

Mistress in Lingerie HandJobs Submissive Crossdresser with Cock until the Last drop of Cum - Encouraging Bisexuals to Cum, Sissy Stocking Wearing Perversion, Jerking off Clitoris Sissy, Female Domination, Dick Slapping 4k

75% 4K 0:26 / 16:16

Mistress in Lingerie HandJobs Submissive Crossdresser with Cock until the Last drop of Cum - Encouraging Bisexuals to Cum, Sissy Stocking Wearing Perversion, Jerking off Clitoris Sissy, Female Domination, Dick Slapping 4k

Clips4sale 11 months ago

HOT Blonde Feminizes and Pegs Boyfriend *EXCLUSIVE*

52% HD 0:10 / 16:44

HOT Blonde Feminizes and Pegs Boyfriend *EXCLUSIVE*

LoyalFans 1 month ago

Sydney's Size-Struck Sissy: A BBC Goddess Destroys Your Manhood JOI

59% HD 0:10 / 10:30

Sydney's Size-Struck Sissy: A BBC Goddess Destroys Your Manhood JOI

LoyalFans 5 months ago

COCK FILLED WHORE (1080p)

67% HD 0:22 / 12:23

COCK FILLED WHORE (1080p)

Clips4sale 1 year ago

Sissy’s Magical Transformation

57% HD 0:10 / 13:13

Sissy’s Magical Transformation

LoyalFans 3 weeks ago

Femboy Fucking Petite Trans Woman - Compilation 11

67% HD 0:10 / 21:29

Femboy Fucking Petite Trans Woman - Compilation 11

LoyalFans 1 month ago

Female Stepmom in Latex Multiple Ruined Orgasms of Sissy Slut Big Cock in black Nylon Stockings - Control a Whore Orgasm, Humiliation of Guy Dignity, Close Female Naked Male, Amateur Couple Perverted Fantasy, Post Cum Play

67% 4K 0:26 / 16:16

Female Stepmom in Latex Multiple Ruined Orgasms of Sissy Slut Big Cock in black Nylon Stockings - Control a Whore Orgasm, Humiliation of Guy Dignity, Close Female Naked Male, Amateur Couple Perverted Fantasy, Post Cum Play

Clips4sale 11 months ago

Total Sissy Amnesia

61% HD 0:30 / 13:15

Total Sissy Amnesia

Clips4sale 10 months ago

OLIVE GREEN RAW SHEMALE FUCKING ANAL HOOK OLIVE GREEN LATEX CATSUIT

84% HD 0:22 / 10:09

OLIVE GREEN RAW SHEMALE FUCKING ANAL HOOK OLIVE GREEN LATEX CATSUIT

Clips4sale 2 years ago

THE POWER TO TURN YOU GAY

47% HD 0:10 / 22:51

THE POWER TO TURN YOU GAY

LoyalFans 3 years ago

NUN SUPERVISED MASTURBATION

56% 4K 0:25 / 13:59

NUN SUPERVISED MASTURBATION

Clips4sale 2 years ago

(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)

67% 4K 0:30 / 1:04:09

(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)

Clips4sale 2 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

House Sissy Made To Clean Filthy Feet (WMV HD)

HD 0:11 / 10:12

House Sissy Made To Clean Filthy Feet (WMV HD)

Clips4sale 3 years ago

Nikki Whiplash makes her husband into a sissy! WL1758

57% 0:12 / 35:45

Nikki Whiplash makes her husband into a sissy! WL1758

Clips4sale 1 year ago

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

52% HD 0:30 / 1:04:09

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

Clips4sale 2 years ago

Just Outta Curiosity

65% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 3 years ago

Just Outta Curiosity

58% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 3 years ago

Scots Sissy Sluts Makeup Part 1

Scots Sissy Sluts Makeup Part 1

Clips4sale 4 years ago

futa dominatrix’s permanent sissification: transforming you into the perfect cockwhore sissy bitch - SD

futa dominatrix’s permanent sissification: transforming you into the perfect cockwhore sissy bitch - SD

Clips4sale 1 week ago

BE ASHAMED FAGGOT

61% HD 0:10 / 11:26

BE ASHAMED FAGGOT

LoyalFans 3 years ago

Chastity and Anal Training

72% 0:30 / 20:51

Chastity and Anal Training

Clips4sale 1 year ago

BBC MAKING WHITE BOYS EXTINCT

47% HD 0:10 / 7:09

BBC MAKING WHITE BOYS EXTINCT

LoyalFans 3 years ago

Boss Wife Sluts You Out *

Boss Wife Sluts You Out *

Clips4sale 1 day ago

Sissy Whore Transformation

66% 0:30 / 8:43

Sissy Whore Transformation

Clips4sale 1 year ago

Futa Step-Mom Feminizes You

62% 4K 0:28 / 25:42

Futa Step-Mom Feminizes You

Clips4sale 1 year ago

Tranny Domme and her redhead friend double fuck sissy impotent bitch - SPH - Trans Woman - Pegging - Femdom - Double Domination - Spanking - Sodomize -

63% 4K 0:49 / 23:23

Tranny Domme and her redhead friend double fuck sissy impotent bitch - SPH - Trans Woman - Pegging - Femdom - Double Domination - Spanking - Sodomize -

Clips4sale 6 months ago

Bailey Wilde Fucking Trans Becki Bottomz

65% HD 0:10 / 17:18

Bailey Wilde Fucking Trans Becki Bottomz

LoyalFans 1 month ago

Cross dresser of the month

56% HD 0:10 / 12:42

Cross dresser of the month

LoyalFans 1 month ago

She Breaks the Hooded Sissy into Her Obedient Property

She Breaks the Hooded Sissy into Her Obedient Property

Clips4sale 2 months ago

Femboy Craves CBT Punishment

69% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

Sissy Jerking Anal Solo Compilation

66% HD 0:10 / 20:10

Sissy Jerking Anal Solo Compilation

LoyalFans 1 month ago

Hotwife BBC Creampie Cleanup – Beta Cuck Eats Every Drop

58% HD 0:10 / 20:34

Hotwife BBC Creampie Cleanup – Beta Cuck Eats Every Drop

LoyalFans 7 months ago

Bullying her Sissy Balls Part 2: Humiliating Ball Weights

HD 0:10 / 10:43

Bullying her Sissy Balls Part 2: Humiliating Ball Weights

LoyalFans 1 month ago

Maid Fluffer for Shecock

55% HD 0:10 / 6:54

Maid Fluffer for Shecock

LoyalFans 4 years ago

Trans Valorie Valentina Fucked by Jake Grand

56% HD 0:10 / 22:07

Trans Valorie Valentina Fucked by Jake Grand

LoyalFans 2 months ago

ForXed Bi First experience PT1 - Blow Job school

55% HD 0:20 / 11:15

ForXed Bi First experience PT1 - Blow Job school

Clips4sale 4 years ago

Sissy Sluts Part 1

48% HD 0:10 / 12:49

Sissy Sluts Part 1

LoyalFans 5 years ago

Humiliation 280

HD 0:25 / 17:27

Humiliation 280

Clips4sale 1 week ago

Chastity release milking - tease and denial

Chastity release milking - tease and denial

Clips4sale 2 years ago

Blow Him For Me

67% 0:11 / 9:26

Blow Him For Me

Clips4sale 3 years ago

Ai Salon Sucker

Ai Salon Sucker

Clips4sale 3 years ago

Gay 4 Pay Fantasy

Premium HD 9:11

Gay 4 Pay Fantasy

Clips4sale 5 days ago

First Female Orgasm of my feminized cuckold in pussy panties

First Female Orgasm of my feminized cuckold in pussy panties

Clips4sale 3 years ago

SISSY SHAWNA IS A SLUTTY FAGGOT

69% HD 0:10 / 23:01

SISSY SHAWNA IS A SLUTTY FAGGOT

LoyalFans 3 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 8 months ago

You Get A Whore Makeover

You Get A Whore Makeover

LoyalFans 2 years ago

I will make you crossdress, sissy, and suck cock for me!

I will make you crossdress, sissy, and suck cock for me!

Clips4sale 4 years ago

Sissy "Locked" into Her New Life (1080p)

HD 0:16 / 13:17

Sissy "Locked" into Her New Life (1080p)

Clips4sale 1 week 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 8 months ago

Solo Sissy Trannny Wife Cuckold BBC Tease

Solo Sissy Trannny Wife Cuckold BBC Tease

Clips4sale 1 month ago

BBC BJ and Anal Sissy Compilation *EXCLUSIVE*

66% HD 0:10 / 27:42

BBC BJ and Anal Sissy Compilation *EXCLUSIVE*

LoyalFans 1 month ago

Sissy Faggot Cocksucker JOI

56% HD 0:25 / 18:16

Sissy Faggot Cocksucker JOI

Clips4sale 2 years ago

TS Becki Bottomz Fucking Bailey Wilde

63% HD 0:10 / 17:18

TS Becki Bottomz Fucking Bailey Wilde

LoyalFans 1 month ago

Sarah Gregory Ball Busts Sissy Sabrina Valentine (HD1080 MP4)

Sarah Gregory Ball Busts Sissy Sabrina Valentine (HD1080 MP4)

Clips4sale 8 months ago

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