Sissy Humiliation Videos (42,333)

Turning My Boyfriend Into A Sissy

Turning My Boyfriend Into A Sissy

xHamster 2 weeks ago

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

66% HD 1:01 / 12:50

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

FapHouse 8 months ago

Sissy in Bondage Teased by Mistress

Sissy in Bondage Teased by Mistress

FapHouse 1 week ago

Sissy Hubby Penetrated

Sissy Hubby Penetrated

GayCK 6 years ago

Cuckold learns to make deep throat in foursome

Cuckold learns to make deep throat in foursome

xHamster 1 year ago

Feminine Sissy Has Fun With 2 Hot Girls

Feminine Sissy Has Fun With 2 Hot Girls

Eporner 7 years ago

Sissy hubby gets a hard anal pounding while being humiliated in HD

Sissy hubby gets a hard anal pounding while being humiliated in HD

GayX 1 week ago

Gay Joy CEI

37% HD 1:01 / 17:00

FapHouse 1 month ago

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

HD 1:01 / 25:52

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

FapHouse 2 weeks ago

fucking my crossdreser wife in the kitchen

fucking my crossdreser wife in the kitchen

xHamster 1 year ago

Stupid Big Tits Sissy Slut Raven Eating Cum after Giving a Blowjob to a Big Black Dildo

Stupid Big Tits Sissy Slut Raven Eating Cum after Giving a Blowjob to a Big Black Dildo

xHamster 1 week ago

Super hot Light-haired Femboy Puts Trans Nymph in Restrain bondage and Predominates Her

Super hot Light-haired Femboy Puts Trans Nymph in Restrain bondage and Predominates Her

TrannyGem 6 days ago

POV Cucked by Transgirl and Your Girlfriend - Jessica Bloom & Polieana

68% HD 0:39 / 25:04

POV Cucked by Transgirl and Your Girlfriend - Jessica Bloom & Polieana

FapHouse 11 months ago

Sissy's tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

Sissy's tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

xHamster 1 year ago

Femboy gonzo Fucky-fucky Abjection: A hardcore crossdresser humiliation and cumshot with big cock

Femboy gonzo Fucky-fucky Abjection: A hardcore crossdresser humiliation and cumshot with big cock

GayVD 3 weeks ago

Mandatory Pee

58% HD 0:39 / 2:28

FapHouse 3 weeks ago

Crossdresser Puts Red-haired Trans Doll in Restrain bondage DOMINATION & SUBMISSION

Crossdresser Puts Red-haired Trans Doll in Restrain bondage DOMINATION & SUBMISSION

TrannyGem 1 week ago

Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation) Jessica Bloom

Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation) Jessica Bloom

Itsrealamateurs 3 days ago

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

xHamster 1 year ago

Sissy takes huge enema then bounces on dildo whilst still inflated

Sissy takes huge enema then bounces on dildo whilst still inflated

xHamster 2 years ago

Sissy crossdresser piss drink slave

Sissy crossdresser piss drink slave

xHamster 1 year ago

Clara Dee JOI: You're My Little Bitch Husband Now

Clara Dee JOI: You're My Little Bitch Husband Now

Jizzberry 1 year ago

Watch these Indian boys dominate and humiliate their pathetic bottom boy in a hot interracial action

Watch these Indian boys dominate and humiliate their pathetic bottom boy in a hot interracial action

GayVD 2 weeks ago

sissy crossdressing outdoors

sissy crossdressing outdoors

xHamster 1 week ago

1 Hour Special: Huge Ass Femboy Samus Wedgie, Spanks, Creampie and Anal Fucking with Multiple Dildos

1 Hour Special: Huge Ass Femboy Samus Wedgie, Spanks, Creampie and Anal Fucking with Multiple Dildos

xHamster 2 months ago

Sissy Boyfriend Takes Inflatable Plug and Penis Pump - I Finally Spit His Cum Inside Through Hollow Plug

Sissy Boyfriend Takes Inflatable Plug and Penis Pump - I Finally Spit His Cum Inside Through Hollow Plug

FapHouse 1 week ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

xHamster 1 year ago

Bi Foursome Facesitting cocksucker training

Bi Foursome Facesitting cocksucker training

xHamster 1 year ago

FEMBOY turns himself in to his college teacher to leave his ass broken

FEMBOY turns himself in to his college teacher to leave his ass broken

xHamster 2 months ago

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

xHamster 1 year ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Femdom Sissy Chastity Tease

Femdom Sissy Chastity Tease

xHamster 1 month ago

A Hole Forever Free Use for Futas for the Rest of Your Life

A Hole Forever Free Use for Futas for the Rest of Your Life

xHamster 2 months ago

Deepthroat and Obedience Feet Test Pt.2

Deepthroat and Obedience Feet Test Pt.2

xHamster 4 months ago

Putting Restraints on Ginger-haired Trans Doll

Putting Restraints on Ginger-haired Trans Doll

TrannyGem 2 weeks ago

Femdom Humiliate Asian Sissy

60% HD 0:39 / 7:23

Femdom Humiliate Asian Sissy

FapHouse 2 months ago

Trans Demon Punishes You With Her Huge Dick And Massive Load of Hot Cum

Trans Demon Punishes You With Her Huge Dick And Massive Load of Hot Cum

xHamster 3 weeks ago

LOLA CUMS FROM BBC

Premium HD 26:13

LOLA CUMS FROM BBC

XVideosRed 2 months ago

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

xHamster 1 month ago

Today I called my new sissy to suck my feet for a while when I was tired of walking

Today I called my new sissy to suck my feet for a while when I was tired of walking

xHamster 2 years ago

Maid Put To Work (Sissy)

Maid Put To Work (Sissy)

Tranny.one 3 years ago

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

xHamster 3 weeks ago

Sissy Secretary Maddy Riding My Big Black Dildo's And Gaping My Ass

Sissy Secretary Maddy Riding My Big Black Dildo's And Gaping My Ass

xHamster 6 months ago

Hung BBC Explodes on Locked Up, Caged Chastity Tranny Slut Sammi Smith

Hung BBC Explodes on Locked Up, Caged Chastity Tranny Slut Sammi Smith

XXXShake 8 months ago

Fucking, Flip Flop

56% 4K 2:00 / 25:04

Fucking, Flip Flop

Flirt4Free 4 months ago

Newbie Sissy Training: Meeting #2. Stretching Sissy Cunt with Fingers. Facesitting. Pussy Worship. Arya Grander

Newbie Sissy Training: Meeting #2. Stretching Sissy Cunt with Fingers. Facesitting. Pussy Worship. Arya Grander

xHamster 1 year ago

Jacob Malik Private Show

58% HD 2:00 / 11:23

Jacob Malik Private Show

Flirt4Free 3 months ago

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

xHamster 1 year ago

Chastity fag slave humiliation pet play bondage

Chastity fag slave humiliation pet play bondage

xHamster 4 months ago

Step Bro Gets Caught Dressing Up

Step Bro Gets Caught Dressing Up

xHamster 3 years ago

CUM DIET

46% 0:11 / 10:13

Clips4sale 3 years ago

Desperate pillow rider

Desperate pillow rider

xHamster 1 month ago

Sasha de Sade is a Latex Sissy Maid for Goddess Tangent

Sasha de Sade is a Latex Sissy Maid for Goddess Tangent

aShemaleTube 7 years ago

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

ShemaleSin 3 years ago

Watch this sissy crossdresser take on a massive BBC without protection

Watch this sissy crossdresser take on a massive BBC without protection

GayX 1 week ago

Dressing you like a sissy and spanking your ass

Dressing you like a sissy and spanking your ass

Bokep.PORN 1 week ago

Sph Amateurs Babe Jerks Crossdresser Male Stick In Femdom Cfnm

Sph Amateurs Babe Jerks Crossdresser Male Stick In Femdom Cfnm

PornUse 1 day ago

Daisy Taylor Trans SPH small penis humiliation JOI

Daisy Taylor Trans SPH small penis humiliation JOI

aShemaleTube 9 months ago

BIG BLACK COCK Without A Condom Crossdresser in Crimson Stocking

BIG BLACK COCK Without A Condom Crossdresser in Crimson Stocking

GayCK 6 years ago

I Will Fuck Your Ass You Pathetic Gay Fag POV

68% HD 1:01 / 31:01

I Will Fuck Your Ass You Pathetic Gay Fag POV

FapHouse 1 year ago

Mandatory Pee

xHamster 3 weeks ago

Sophia Loreen Party on Oct 31, 2025 - Part 2

55% 4K 2:00 / 6:28

Sophia Loreen Party on Oct 31, 2025 - Part 2

Flirt4Free 7 months ago

Roy & Hercules & Jamer Private Show

46% HD 2:00 / 4:09

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

Consequences for Breaking Out of Chastity

65% HD 1:01 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 2 weeks ago

Sissy trainer - Give your ass

Sissy trainer - Give your ass

DeegX 3 years ago

Dominated by the Trans Gamer Girl Melissa Masters – Teaser

Dominated by the Trans Gamer Girl Melissa Masters – Teaser

Tranny.one 3 years ago

Luke Hardy & Cristian Ford Party on May 17, 2026 - Part 3

HD 2:00 / 55:13

Luke Hardy & Cristian Ford Party on May 17, 2026 - Part 3

Flirt4Free 3 weeks ago

sissyjoyce - mistress laura plays with me

sissyjoyce - mistress laura plays with me

TransDoe 2 years ago

Femdom Humiliate Asian Sissy

54% HD 1:01 / 7:23

Femdom Humiliate Asian Sissy

FapHouse 2 months ago

Humiliated Sissy Custom #2

57% HD 0:10 / 14:23

Humiliated Sissy Custom #2

LoyalFans 1 year ago

The Blizzard Part 2

The Blizzard Part 2

Transvids.tv 1 week ago

fat sissy pig playing on the floor like it should be

fat sissy pig playing on the floor like it should be

xHamster 2 months ago

Sissy coming home from work

Sissy coming home from work

xHamster 11 months ago

Jacob Malik Private Show

56% HD 2:00 / 8:46

Jacob Malik Private Show

Flirt4Free 3 months ago

The Sissy Show - dominatrix humiliates two feminized British sluts - Sasha de Sade

The Sissy Show - dominatrix humiliates two feminized British sluts - Sasha de Sade

aShemaleTube 7 years ago

femdom tgirl gives SPH and busts whiteboi balls with BBC

66% 0:30 / 17:33

femdom tgirl gives SPH and busts whiteboi balls with BBC

Clips4sale 1 year ago

Sexy Lovers

62% HD 2:00 / 5:08

Flirt4Free 4 months ago

Black Owned sissy bitch humiliated and used to please BBC

Black Owned sissy bitch humiliated and used to please BBC

VipTube 1 month ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 week ago

Are you really wearing my Swimsuit and Stockings Clip 1

Are you really wearing my Swimsuit and Stockings Clip 1

xHamster 1 year ago

Sasha De Sade goes wild with her toys in a hot webcam session

Sasha De Sade goes wild with her toys in a hot webcam session

TrannyMovs 2 months ago

See the New Slave They Humiliate, Torment & Hard Fist

65% HD 1:01 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 6 days ago

Paulo & Jose & Sander Private Show

67% HD 2:00 / 7:57

Paulo & Jose & Sander Private Show

Flirt4Free 1 week ago

Homemade sissy training strapon madam reads the newspaper

Homemade sissy training strapon madam reads the newspaper

xHamster 1 year ago

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

Trans Femdom Big Dick Sissy Encouragement - Jessica Bloom

xHamster 2 years ago

Rubbing my inverted cage cock like a pussy clit and cumming 4 times

Rubbing my inverted cage cock like a pussy clit and cumming 4 times

xHamster 3 years ago

Goth trans woman humiliates you in a JOI

Goth trans woman humiliates you in a JOI

aShemaleTube 4 weeks ago

Daphne Millerr Private Show

4K 2:00 / 21:09

Daphne Millerr Private Show

Flirt4Free 1 week ago

Sophia Loreen Party on May 1, 2026 - Part 3

HD 2:00 / 1:44:32

Sophia Loreen Party on May 1, 2026 - Part 3

Flirt4Free 1 month ago

Sabrina Smiith Private Show

70% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 5 months ago

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

HD 0:39 / 23:31

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

FapHouse 4 months ago

Nicky Rip the Clothes and Tickle

46% HD 1:01 / 14:18

Nicky Rip the Clothes and Tickle

FapHouse 6 months ago

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV Clip 1

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV Clip 1

xHamster 1 month ago

fat sissy fuck dancing for men to insult and laugh at Oink

fat sissy fuck dancing for men to insult and laugh at Oink

xHamster 3 months ago

Alpha Hunk Spits and Pisses on your face - Slave Training

Alpha Hunk Spits and Pisses on your face - Slave Training

xHamster 2 years ago

Between the Lines & Between My Legs

Between the Lines & Between My Legs

xHamster 7 months ago

How Badly You Want to Worship My Phat Ass?

68% HD 2:00 / 13:31

How Badly You Want to Worship My Phat Ass?

Flirt4Free 2 years ago

Daphne Millerr Private Show

Daphne Millerr Private Show

Flirt4Free 1 week ago

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Pornfact 1 week ago

Luccas & Jhordy & Master Private Show

56% HD 2:00 / 12:04

Luccas & Jhordy & Master Private Show

Flirt4Free 3 months ago

I touched a stranger's dick in a restaurant

I touched a stranger's dick in a restaurant

xHamster 10 months ago

I will degrade and reduce you to tiny cock fuck toy you miserable cunt

I will degrade and reduce you to tiny cock fuck toy you miserable cunt

xHamster 1 year ago

Edlin Dockray Private Show

60% HD 2:00 / 13:31

Edlin Dockray Private Show

Flirt4Free 2 years ago

sissy pig Cosmicjones88 wants to be a good girl

sissy pig Cosmicjones88 wants to be a good girl

xHamster 4 months ago

Corrine Dittmann Private Show

59% 4K 2:00 / 5:04

Corrine Dittmann Private Show

Flirt4Free 9 months ago

Will Your Parents Be Proud? (in Spanish)

Will Your Parents Be Proud? (in Spanish)

xHamster 1 year ago

Small clit virgin shemale get her first blowjob intense orgasm and moaning cum swallowing

Small clit virgin shemale get her first blowjob intense orgasm and moaning cum swallowing

xHamster 3 months ago

Giovanni Becomes Giovanna

Giovanni Becomes Giovanna

xHamster 2 months ago

Piss Slave Sissy

Piss Slave Sissy

xHamster 2 months ago

Horny Sissy Waiting for BBC She Enjoy My Cock Again

Horny Sissy Waiting for BBC She Enjoy My Cock Again

xHamster 10 months ago

Duct Tape on My Mouth

HD 2:00 / 11:45

Duct Tape on My Mouth

Flirt4Free 6 months ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

51% HD 2:00 / 56:20

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 2 months ago

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

xHamster 4 months ago

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

TrannyGem 3 years ago

Put Your Tongue into My Foreskin

61% HD 2:00 / 5:07

Put Your Tongue into My Foreskin

Flirt4Free 2 years ago

Liam Jacobson Private Show

50% HD 2:00 / 5:47

Liam Jacobson Private Show

Flirt4Free 1 year ago

Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll

Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll

xHamster 8 months ago

Corrine Dittmann Private Show

53% 4K 2:00 / 5:07

Corrine Dittmann Private Show

Flirt4Free 2 weeks ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 9 years ago

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