Sissy Humiliation Videos (3,670)

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

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

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

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

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

The Gay Awakening Podcast Episode #58 - Sissy Asshole Completely Owned

41% HD 0:20 / 29:43

The Gay Awakening Podcast Episode #58 - Sissy Asshole Completely Owned

Clips4sale 2 years 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)

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57% HD 0:28 / 13:08

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

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

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

Sissy Roommate Girly JOI

42% 0:14 / 10:33

Sissy Roommate Girly JOI

Clips4sale 2 years ago

GLORYHOLE CONFESSIONS

64% HD 0:10 / 8:42

GLORYHOLE CONFESSIONS

LoyalFans 3 years ago

STROKE FOR DICK FAGGOT

49% HD 0:10 / 8:55

STROKE FOR DICK FAGGOT

LoyalFans 3 years ago

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60% HD 0:10 / 16:01

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

LoyalFans 1 year ago

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64% 4K 0:25 / 16:22

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Clips4sale 11 months ago

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67% 0:30 / 17:33

femdom tgirl gives SPH and busts whiteboi balls with BBC

Clips4sale 1 year ago

Diaper Sissy Circus Freak

HD 0:51 / 16:30

Diaper Sissy Circus Freak

Clips4sale 2 weeks 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

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

Pissy Sissy

65% HD 0:25 / 18:02

Clips4sale 1 year 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

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

GLORYHOLE LUNCH BREAK

52% HD 0:10 / 24:59

GLORYHOLE LUNCH BREAK

LoyalFans 3 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

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

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 years ago

Slut makeover and anal training

49% HD 0:24 / 9:27

Slut makeover and anal training

Clips4sale 1 year ago

Feminized In France (HD MP4)

56% 4K 0:29 / 16:00

Feminized In France (HD MP4)

Clips4sale 2 years ago

Sucking Dick is Good for You

Sucking Dick is Good for You

Clips4sale 3 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

LADY YUNA FOOTSTOOL

LADY YUNA FOOTSTOOL

Clips4sale 4 years 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

Ruined By SheMales

44% HD 0:15 / 7:58

Ruined By SheMales

Clips4sale 2 years 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

PANTYHOSE WEARING SISSY SLUT TRANCE

63% 4K 0:25 / 20:47

PANTYHOSE WEARING SISSY SLUT TRANCE

Clips4sale 3 years ago

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63% HD 0:30 / 19:59

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Clips4sale 1 year ago

Sissy Slave Interview

52% HD 0:24 / 9:32

Sissy Slave Interview

Clips4sale 3 years ago

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50% 4K 0:23 / 11:38

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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

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

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Clips4sale 11 months 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

Good Girl Fucked, Bad Girl Cucked

69% HD 1:00 / 29:25

Good Girl Fucked, Bad Girl Cucked

Clips4sale 3 years ago

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Clips4sale 8 months 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 in Chastity Fucked Compilation

56% HD 0:10 / 25:35

Sissy in Chastity Fucked Compilation

LoyalFans 1 month 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

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 3 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

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

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

Bully Turns You Into A SISSY!

HD 0:10 / 10:07

Bully Turns You Into A SISSY!

LoyalFans 3 months ago

Sissy Gets Caught

64% 0:30 / 9:26

Sissy Gets Caught

Clips4sale 1 year 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

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

SISSYGASM ENCOURAGEMENT

55% 4K 0:30 / 7:25

SISSYGASM ENCOURAGEMENT

Clips4sale 2 years 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

NUN SUPERVISED MASTURBATION

56% 4K 0:25 / 13:59

NUN SUPERVISED MASTURBATION

Clips4sale 2 years 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

Total Sissy Amnesia

61% HD 0:30 / 13:15

Total Sissy Amnesia

Clips4sale 10 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

Cross dresser of the month

56% HD 0:10 / 12:42

Cross dresser of the month

LoyalFans 1 month ago

Sissy’s Magical Transformation

57% HD 0:10 / 13:13

Sissy’s Magical Transformation

LoyalFans 4 weeks ago

THE POWER TO TURN YOU GAY

45% HD 0:10 / 22:51

THE POWER TO TURN YOU GAY

LoyalFans 3 years 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

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

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

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

COCK FILLED WHORE (1080p)

67% HD 0:22 / 12:23

COCK FILLED WHORE (1080p)

Clips4sale 1 year 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

(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

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

SHEMALE SNAKE INVASION

54% HD 0:10 / 13:25

SHEMALE SNAKE INVASION

LoyalFans 1 year ago

Sissy Faggot Cocksucker JOI

56% HD 0:25 / 18:16

Sissy Faggot Cocksucker JOI

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

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

HD 0:16 / 13:17

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

Clips4sale 2 weeks ago

Psychoanalysis with a Trans Goddess ends up in humiliation

70% 4K 0:50 / 19:27

Psychoanalysis with a Trans Goddess ends up in humiliation

Clips4sale 10 months 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

BBC MAKING WHITE BOYS EXTINCT

47% HD 0:10 / 7:09

BBC MAKING WHITE BOYS EXTINCT

LoyalFans 3 years ago

Futa Step-Mom Feminizes You

62% 4K 0:28 / 25:42

Futa Step-Mom Feminizes You

Clips4sale 1 year ago

Bailey Wilde Fucking Trans Becki Bottomz

65% HD 0:10 / 17:18

Bailey Wilde Fucking Trans Becki Bottomz

LoyalFans 1 month ago

Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

Blonde Trans Beauty Sucking BBC *EXCLUSIVE*

LoyalFans 1 month ago

Scots Sissy Sluts Makeup Part 1

Scots Sissy Sluts Makeup Part 1

Clips4sale 4 years 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

Sissy Whore Transformation

66% 0:30 / 8:43

Sissy Whore Transformation

Clips4sale 1 year ago

Fucked In Every Room: Barbie's Wet Dream House Part 3 (WMV)

4K 0:48 / 15:11

Fucked In Every Room: Barbie's Wet Dream House Part 3 (WMV)

Clips4sale 4 years ago

Shemale Champagne Strapon in Bath

Shemale Champagne Strapon in Bath

Clips4sale 4 years ago

I've been putting estrogen in your coffee: loving feminization and futa fucking

62% HD 0:10 / 14:31

I've been putting estrogen in your coffee: loving feminization and futa fucking

LoyalFans 1 year 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

Maid Fluffer for Shecock

55% HD 0:10 / 6:54

Maid Fluffer for Shecock

LoyalFans 4 years ago

Spoiled Sissy Princess

51% HD 0:10 / 16:25

Spoiled Sissy Princess

LoyalFans 7 months ago

Sissy Jerking Anal Solo Compilation

66% HD 0:10 / 20:10

Sissy Jerking Anal Solo Compilation

LoyalFans 1 month ago

Femboy Craves CBT Punishment

69% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

SISSYBB EXPOSED AGAIN

61% HD 0:10 / 20:55

SISSYBB EXPOSED AGAIN

LoyalFans 3 years ago

You Get A Whore Makeover

You Get A Whore Makeover

LoyalFans 2 years 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

Humiliation 280

HD 0:25 / 17:27

Humiliation 280

Clips4sale 1 week ago

Boss Wife Sluts You Out *

Boss Wife Sluts You Out *

Clips4sale 2 days ago

Mommy's Holiday Sissy Inspection

Mommy's Holiday Sissy Inspection

Clips4sale 9 months ago

Chastity release milking - tease and denial

Chastity release milking - tease and denial

Clips4sale 2 years ago

Gay 4 Pay Fantasy

Premium HD 9:11

Gay 4 Pay Fantasy

Clips4sale 6 days ago

POV Blonde Crossdresser in Chastity Fucked *EXCLUSUVE*

POV Blonde Crossdresser in Chastity Fucked *EXCLUSUVE*

LoyalFans 1 month 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

Ai Salon Sucker

Ai Salon Sucker

Clips4sale 3 years 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

Solo Sissy Trannny Wife Cuckold BBC Tease

Solo Sissy Trannny Wife Cuckold BBC Tease

Clips4sale 1 month ago

GLORYHOLE LUNCH BREAK

52% 4K 0:25 / 24:59

GLORYHOLE LUNCH BREAK

Clips4sale 3 years 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

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

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