Sissy Humiliation (18,473)

The best and newest sissy humiliation videos

Mature Mistress Femdom Strapon Humiliation Young Sissy Slave Boy

Mature Mistress Femdom Strapon Humiliation Young Sissy Slave Boy

PornoXO 1 year ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

49% HD 1:01 / 12:49

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

FapHouse 2 months ago

Angelica Swiss Party on Feb 8, 2026 - Part 4

HD 2:00 / 33:23

Angelica Swiss Party on Feb 8, 2026 - Part 4

Flirt4Free 1 week ago

I fuck my husband on the beach

I fuck my husband on the beach

xHamster 1 year ago

Strapon Pegging Compilation

Strapon Pegging Compilation

xHamster 1 week ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

SortPorn 1 year ago

Cuckold Fantasies Volume 6

Cuckold Fantasies Volume 6

xHamster 4 years ago

forbidden to for my cuckold in a chastity cage

forbidden to for my cuckold in a chastity cage

xHamster 5 months ago

Cuckold Archive Sissys wife on vacation

Cuckold Archive Sissys wife on vacation

xHamster 2 years ago

I my husband with another guy's

I my husband with another guy's

xHamster 1 month ago

Chastity, Locked! (absolute Power 2)

75% HD 1:01 / 9:10

Chastity, Locked! (absolute Power 2)

FapHouse 9 months ago

BLONDE WIFE GETS CAUGHT CHEATING THEN CUCKS HER HUSBAND POV

BLONDE WIFE GETS CAUGHT CHEATING THEN CUCKS HER HUSBAND POV

xHamster 2 years ago

Milking of femboy with orgasm control

Milking of femboy with orgasm control

xHamster 2 years ago

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

XVideos 1 year ago

1st step for virgin sissy, snatch defloration. Anal stretching, FaceSitting, Humiliation, Pee.

1st step for virgin sissy, snatch defloration. Anal stretching, FaceSitting, Humiliation, Pee.

Lesbian8 1 month ago

Experience the Tempting Power Play with MILF Rosie: A Journey of Rejection and Worship

Experience the Tempting Power Play with MILF Rosie: A Journey of Rejection and Worship

JuicyVid 4 days ago

Angelica Swiss Party on Feb 8, 2026 - Part 4

HD 2:00 / 28:42

Angelica Swiss Party on Feb 8, 2026 - Part 4

Flirt4Free 1 week ago

Jhanne Cherry Private Show

44% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Your Sissy dream come True - Female POV blowjob - Roleplay

Your Sissy dream come True - Female POV blowjob - Roleplay

xHamster 1 year ago

POV JOI vol 3

xHamster 2 years ago

Helena Red Private Show

68% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Jhanne Cherry Private Show

54% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 5 months ago

Abril Newton Private Show

63% HD 2:00 / 1:41:59

Abril Newton Private Show

Flirt4Free 6 months ago

Emily & Stesha Private Show

58% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 1 month ago

Sofi Saenz Private Show

66% HD 2:00 / 8:23

Sofi Saenz Private Show

Flirt4Free 5 months ago

Nefertiti & Demian Private Show

57% HD 2:00 / 9:43

Nefertiti & Demian Private Show

Flirt4Free 2 years ago

Cuckold Dreams Volume 24

Cuckold Dreams Volume 24

FreePorn8 1 year ago

Abril Newton Private Show

54% HD 2:00 / 17:42

Abril Newton Private Show

Flirt4Free 5 months ago

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

xHamster 1 year ago

Abril Newton Private Show

58% 4K 2:00 / 11:48

Abril Newton Private Show

Flirt4Free 6 months ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

xHamster 4 years ago

Feminized and Pegged - Ruby Onyx

Feminized and Pegged - Ruby Onyx

xHamster 1 week ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

xHamster 6 months ago

Sissy Maid Slut Humiliated by 2 Hotwifes and BBC

Sissy Maid Slut Humiliated by 2 Hotwifes and BBC

xHamster 1 year ago

The Irish Bull

xHamster 4 months ago

Mature mistress Femdom Strapon Humiliation young sissy slave boy

Mature mistress Femdom Strapon Humiliation young sissy slave boy

Eporner 1 year ago

MILF made her husband shave her pussy, drink piss and watch her lover suff her with a creampie

MILF made her husband shave her pussy, drink piss and watch her lover suff her with a creampie

XGroovy 2 years ago

Cuckolds secret Blonde MILF and her 2 BBC friends

Cuckolds secret Blonde MILF and her 2 BBC friends

xHamster 2 years ago

The Irish Bull

57% HD 1:01 / 11:32

FapHouse 4 months ago

Worship My Pussy and Ass

Worship My Pussy and Ass

xHamster 4 years ago

You're My Slut Slave

You're My Slut Slave

xHamster 1 year ago

Chastity, Locked! (absolute Power 2)

67% HD 0:39 / 9:10

Chastity, Locked! (absolute Power 2)

FapHouse 9 months ago

The White Room - Humiliation and Milking - Part 1

The White Room - Humiliation and Milking - Part 1

xHamster 1 week ago

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

xHamster 1 year ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

xHamster 2 years ago

Delivery Guy Becomes a Sissy

63% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 1 month ago

My husband has a new cock

My husband has a new cock

xHamster 1 year ago

Mommy likes giving Daddy her big fat cock! FitNaughtyCouple

Mommy likes giving Daddy her big fat cock! FitNaughtyCouple

xHamster 3 years ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 1 month ago

Lesbian Ass Licking 11

Lesbian Ass Licking 11

xHamster 2 years ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 2 weeks ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

Lesbian8 10 months ago

Jhanne Cherry Private Show

50% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Cuckold Dreams Volume 24

Cuckold Dreams Volume 24

SortPorn 3 years ago

She try to get my limp clitty penis hard

She try to get my limp clitty penis hard

xHamster 4 weeks ago

Flexing on the Sissy Fuck Mat!!

54% HD 0:39 / 16:18

Flexing on the Sissy Fuck Mat!!

FapHouse 10 months ago

Femdom Fantasy - AI Animated Slideshow for Adults

Femdom Fantasy - AI Animated Slideshow for Adults

xHamster 6 months ago

Cuckold Archive Sissy drinks BBs jizz after his wife had sex

Cuckold Archive Sissy drinks BBs jizz after his wife had sex

xHamster 2 years ago

The Irish Bull

54% HD 0:39 / 11:32

FapHouse 4 months ago

1st step for virgin sissy, vagina defloration. Anal stretching, FaceSitting, Humiliation, Pee.

1st step for virgin sissy, vagina defloration. Anal stretching, FaceSitting, Humiliation, Pee.

FreePorn8 1 month ago

Emily & Stesha Private Show

58% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Sissy Training & Teaching U How to Suck Alpha's Huge Cock!

Sissy Training & Teaching U How to Suck Alpha's Huge Cock!

xHamster 10 months ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

xHamster 2 years ago

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

xHamster 1 year ago

Jhanne Cherry Private Show

67% 4K 2:00 / 14:24

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Magic Fantasy: I Transform You Into a Real Sissy Slave Girl

63% HD 0:07 / 0:40

Magic Fantasy: I Transform You Into a Real Sissy Slave Girl

FapHouse 3 months ago

I lock my husband's cock in a chastity cage

I lock my husband's cock in a chastity cage

xHamster 1 year ago

Cuckold on the beach

Cuckold on the beach

xHamster 2 months ago

Cuckolds secret Redhead MILF with 2 BBC bulls. Husband

Cuckolds secret Redhead MILF with 2 BBC bulls. Husband

xHamster 2 years ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Cuckold Dreams volume 23

Cuckold Dreams volume 23

SortPorn 1 year ago

humiliatrix fetish

humiliatrix fetish

Amateur8 1 year ago

Fuck Slut Is Face Fucked and Humiliated by Nympho Goddess!

70% HD 1:01 / 10:34

Fuck Slut Is Face Fucked and Humiliated by Nympho Goddess!

FapHouse 8 months ago

Happy Wife, Happy Life, Slutty Bitch BBC Railed In Front of Hot Hubby - DFXtra

Happy Wife, Happy Life, Slutty Bitch BBC Railed In Front of Hot Hubby - DFXtra

Some.Porn 10 months ago

Jhanne Cherry Private Show

50% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 4 months ago

Alpha he is now my submissive sissy

Alpha he is now my submissive sissy

xHamster 1 year ago

Jhanne Cherry Private Show

55% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 5 months ago

Home From the Wedding, Foot Cuck!

72% HD 1:01 / 16:14

Home From the Wedding, Foot Cuck!

FapHouse 11 months ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

PornFreeNow 10 months ago

CUM CHALLENGE FOR BISEXUAL PERVS

CUM CHALLENGE FOR BISEXUAL PERVS

xHamster 1 year ago

Emily & Stesha Private Show

49% 4K 2:00 / 7:00

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Feminized and Pegged - Ruby Onyx

HD 1:01 / 20:11

Feminized and Pegged - Ruby Onyx

FapHouse 1 week ago

My husband's cock is desperate in his chastity cage

My husband's cock is desperate in his chastity cage

xHamster 1 year ago

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

xHamster 2 years ago

Princess Penis

xHamster 3 months ago

Olga Barz - anal sex with strap-on

Olga Barz - anal sex with strap-on

xHamster 3 years ago

Emily & Stesha Private Show

46% 4K 2:00 / 4:08

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Humiliating and Pegging My Sissy Bitch with BBC Dildo

55% HD 1:01 / 6:32

Humiliating and Pegging My Sissy Bitch with BBC Dildo

FapHouse 3 weeks ago

Cuckold Dreams volume 23

Cuckold Dreams volume 23

FreePorn8 1 year ago

two Pathetic Sissies Get to Suck and Screw Each Other

two Pathetic Sissies Get to Suck and Screw Each Other

PornFreeNow 1 month ago

Sissy Swimsuit Slut Bend Over and Gets Fucked

48% HD 1:01 / 6:18

Sissy Swimsuit Slut Bend Over and Gets Fucked

FapHouse 5 months ago

Therapy

60% HD 0:39 / 4:47

FapHouse 4 months ago

Kristinaxxx sissy training

Kristinaxxx sissy training

AnySex 2 years ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 3 months ago

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

xHamster 1 year ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 2 months ago

Red open crotch thong, mature

Red open crotch thong, mature

xHamster 8 months ago

My Cuckold husband loves humiliation and spitting on him

My Cuckold husband loves humiliation and spitting on him

xHamster 5 months ago

Amber Fletcher Private Show - Part 3

65% HD 2:00 / 21:25

Amber Fletcher Private Show - Part 3

Flirt4Free 1 year ago

Hard Amazon fuck creampie cum drip

Hard Amazon fuck creampie cum drip

xHamster 2 years ago

Goddess Sabrina - 2 of 6

63% HD 1:01 / 10:17

Goddess Sabrina - 2 of 6

FapHouse 10 months ago

Suck Cock, Eat CREAM PIE and Swallow SNOWBALL is what Cuckold's Wife DEMANDS of Her SISSY :-)

Suck Cock, Eat CREAM PIE and Swallow SNOWBALL is what Cuckold's Wife DEMANDS of Her SISSY :-)

xHamster 2 years ago

Therapy session for sissy boys

Therapy session for sissy boys

xHamster 2 years ago

Home From the Wedding, Foot Cuck!

60% HD 0:39 / 16:14

Home From the Wedding, Foot Cuck!

FapHouse 11 months ago

The Sissygasm

47% 1:01 / 12:01

FapHouse 8 months ago

Femdom and Cuckold Humiliation Compilation

Femdom and Cuckold Humiliation Compilation

xHamster 9 months ago

Bar Flirt Fantasy: Chastity and Sissy Transformation

Bar Flirt Fantasy: Chastity and Sissy Transformation

xHamster 6 months ago

amazon cum dripping cream pie

amazon cum dripping cream pie

xHamster 1 year ago

One Ass to Rule them All

One Ass to Rule them All

xHamster 4 years ago

filth mouthed messy talking wife humiliates sissy hubby on the phone whilst getting bbc

filth mouthed messy talking wife humiliates sissy hubby on the phone whilst getting bbc

MatureTubeHere 1 week ago

Jhanne Cherry Private Show

58% 4K 2:00 / 6:40

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 2 weeks ago

Mistress wife discipline her sissy husband on kitchen

Mistress wife discipline her sissy husband on kitchen

xHamster 2 years ago

My husband's penis frozen

My husband's penis frozen

xHamster 3 months ago

German Sissy Becomes Whore Fatma a True Transformation

64% HD 0:07 / 0:40

German Sissy Becomes Whore Fatma a True Transformation

FapHouse 3 months ago

Jhanne Cherry Private Show

67% 4K 2:00 / 7:28

Jhanne Cherry Private Show

Flirt4Free 7 months ago

BBC Owned My Womb

HD 0:10 / 14:56

BBC Owned My Womb

LoyalFans 2 weeks ago

SUCK THIS COCK 4 ME - part 5

SUCK THIS COCK 4 ME - part 5

xHamster 11 months ago

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