Sissy Humiliation Videos (3,674)

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

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

Honeymoon Cuckold

43% 0:30 / 19:33

Honeymoon Cuckold

Clips4sale 1 year 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)

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

Bailey Wilde Fucking Trans Becki Bottomz

65% HD 0:10 / 17:18

Bailey Wilde Fucking Trans Becki Bottomz

LoyalFans 1 month ago

Closet Faggot Dirty Talk

49% HD 0:11 / 6:35

Closet Faggot Dirty Talk

Clips4sale 4 years ago

Fetish221 - FemDom: Sissifying a Billionaire

HD 0:30 / 11:36

Fetish221 - FemDom: Sissifying a Billionaire

Clips4sale 1 year ago

THE POWER TO TURN YOU GAY

45% HD 0:10 / 22:51

THE POWER TO TURN YOU GAY

LoyalFans 3 years ago

All About Panties

All About Panties

Clips4sale 2 years 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

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

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

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

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

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

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

Slut makeover and anal training

49% HD 0:24 / 9:27

Slut makeover and anal training

Clips4sale 1 year ago

I am a Diaper Sissy Cheerleader

HD 0:46 / 16:31

I am a Diaper Sissy Cheerleader

Clips4sale 5 days ago

Sucking Dick is Good for You

Sucking Dick is Good for You

Clips4sale 3 years ago

Feminized In France (HD MP4)

56% 4K 0:29 / 16:00

Feminized In France (HD MP4)

Clips4sale 2 years ago

LADY YUNA FOOTSTOOL

LADY YUNA FOOTSTOOL

Clips4sale 4 years ago

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 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

Strap On Custom POV

HD 0:30 / 10:05

Strap On Custom POV

Clips4sale 1 year 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

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

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

Sissy Slave Interview

52% HD 0:24 / 9:32

Sissy Slave Interview

Clips4sale 3 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 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

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

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 (HD1080 MP4)

Sarah Gregory Ball Busts Sissy Sabrina Valentine (HD1080 MP4)

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

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Sarah Gregory Ball Busts Sissy Sabrina Valentine (STANDARD WMV)

Clips4sale 8 months 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

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

Pissy Sissy

69% HD 0:25 / 18:02

Clips4sale 1 year 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 in Chastity Fucked Compilation

56% HD 0:10 / 25:35

Sissy in Chastity Fucked Compilation

LoyalFans 1 month ago

Ruined By SheMales

44% HD 0:15 / 7:58

Ruined By SheMales

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

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

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

TS Valorie Valentina Fucked Hard

58% HD 0:10 / 22:07

TS Valorie Valentina Fucked Hard

LoyalFans 2 months ago

NUN SUPERVISED MASTURBATION

56% 4K 0:25 / 13:59

NUN SUPERVISED MASTURBATION

Clips4sale 3 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

GLORYHOLE LUNCH BREAK

52% HD 0:10 / 24:59

GLORYHOLE LUNCH BREAK

LoyalFans 3 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

Total Sissy Amnesia

61% HD 0:30 / 13:15

Total Sissy Amnesia

Clips4sale 10 months ago

COCK FILLED WHORE (1080p)

67% HD 0:22 / 12:23

COCK FILLED WHORE (1080p)

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

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

Cross dresser of the month

56% HD 0:10 / 12:42

Cross dresser of the month

LoyalFans 1 month ago

Just Outta Curiosity

65% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 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

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

Sissy Faggot Cocksucker JOI

56% HD 0:25 / 18:16

Sissy Faggot Cocksucker JOI

Clips4sale 2 years ago

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

70% 4K 0:50 / 24:39

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

Clips4sale 4 months ago

Slut Training PT2 - lets make use the teeth for a reason! - 480P

66% 0:15 / 9:37

Slut Training PT2 - lets make use the teeth for a reason! - 480P

Clips4sale 2 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

You Get A Whore Makeover

You Get A Whore Makeover

LoyalFans 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

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

Just Outta Curiosity

58% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 3 years ago

Sissy’s Magical Transformation

57% HD 0:10 / 13:13

Sissy’s Magical Transformation

LoyalFans 1 month ago

Wife Turns You Into BBC Sissy

Premium HD 19:57

Wife Turns You Into BBC Sissy

Clips4sale 2 weeks ago

Scots Sissy Sluts Makeup Part 1

Scots Sissy Sluts Makeup Part 1

Clips4sale 4 years ago

Slut training blow job Encouraging PT1 - Real time session recording 480p

Slut training blow job Encouraging PT1 - Real time session recording 480p

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

Shemale Champagne Strapon in Bath

Shemale Champagne Strapon in Bath

Clips4sale 4 years ago

BBC MAKING WHITE BOYS EXTINCT

47% HD 0:10 / 7:09

BBC MAKING WHITE BOYS EXTINCT

LoyalFans 3 years ago

Maid Fluffer for Shecock

55% HD 0:10 / 6:54

Maid Fluffer for Shecock

LoyalFans 4 years ago

Femboy Craves CBT Punishment

69% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

Sissy Jerking Anal Solo Compilation

70% HD 0:10 / 20:10

Sissy Jerking Anal Solo Compilation

LoyalFans 1 month ago

Grooming Gays

69% HD 0:29 / 8:46

Clips4sale 2 years ago

Sissy Sluts Part 1

48% HD 0:10 / 12:49

Sissy Sluts Part 1

LoyalFans 5 years ago

TURNING SISSY SLUT INTO MY PET

48% HD 0:10 / 18:01

TURNING SISSY SLUT INTO MY PET

LoyalFans 2 years ago

GLORYHOLE LUNCH BREAK

52% 4K 0:25 / 24:59

GLORYHOLE LUNCH BREAK

Clips4sale 3 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

Blow Him For Me

67% 0:11 / 9:26

Blow Him For Me

Clips4sale 3 years 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

POV Blonde Crossdresser in Chastity Fucked *EXCLUSUVE*

POV Blonde Crossdresser in Chastity Fucked *EXCLUSUVE*

LoyalFans 2 months ago

POV Sexy Blonde Crossdresser Sucking Cock

POV Sexy Blonde Crossdresser Sucking Cock

LoyalFans 2 months ago

Two Dominants. One very willing trans sub heavy impact bottom. 🖤🔥

HD 0:10 / 26:48

Two Dominants. One very willing trans sub heavy impact bottom. 🖤🔥

LoyalFans 2 weeks ago

Virgin Feminized by Sex Coach

HD 0:10 / 18:38

Virgin Feminized by Sex Coach

LoyalFans 2 years ago

Sexy Blonde Feminizes Boyfriend Then Blowjob *EXCLUSIVE*

65% HD 0:10 / 4:05

Sexy Blonde Feminizes Boyfriend Then Blowjob *EXCLUSIVE*

LoyalFans 1 month 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

TS Becki Bottomz Fucking Bailey Wilde

63% HD 0:10 / 17:18

TS Becki Bottomz Fucking Bailey Wilde

LoyalFans 1 month ago

Don't Pick Up Hitchhikers

62% HD 0:30 / 43:37

Don't Pick Up Hitchhikers

Clips4sale 1 year 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

Diaper Sissy Circus Freak

HD 0:51 / 16:30

Diaper Sissy Circus Freak

Clips4sale 2 weeks ago

Cross Dressing Sissy Dick Rider

53% HD 0:10 / 8:05

Cross Dressing Sissy Dick Rider

LoyalFans 2 years 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

New Sissy Clitty Locked! (4K)

Premium 4K 10:38

New Sissy Clitty Locked! (4K)

Clips4sale 2 weeks ago

New Job For You Sissy

New Job For You Sissy

LoyalFans 2 years ago

Little Sissy Goon For Cock

Little Sissy Goon For Cock

Clips4sale 8 months ago

SLUT MICHELLES BBC SUCKING LESSON

70% 4K 0:25 / 26:32

SLUT MICHELLES BBC SUCKING LESSON

Clips4sale 3 years ago

Femboy Fucking Trans Becki Bottomz

55% HD 0:10 / 32:55

Femboy Fucking Trans Becki Bottomz

LoyalFans 1 month ago

Sophia Truee Humiliates and Exposes a Sissy Slut

Sophia Truee Humiliates and Exposes a Sissy Slut

Clips4sale 2 years ago

The Sissy Peep Show (MP4)

The Sissy Peep Show (MP4)

Clips4sale 1 year ago

Hot Sissies Fucking Compilation

HD 0:10 / 17:05

Hot Sissies Fucking Compilation

LoyalFans 1 month ago

You've been a failure man but now you are my sissy wife!

You've been a failure man but now you are my sissy wife!

Clips4sale 7 months 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 Whore Transformation

66% 0:30 / 8:43

Sissy Whore Transformation

Clips4sale 1 year ago

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