Sissy Training - Porn Videos (148,448)

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 1 month ago

Bi Encouragement Training - Take 2 Of My Mans Cumshots

Bi Encouragement Training - Take 2 Of My Mans Cumshots

XHamster 1 month ago

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Dafreeporn 3 years ago

Jhanne Cherry Private Show

54% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years ago

He's been asking for so long. I saw for the first time what a male anal orgasm is.

He's been asking for so long. I saw for the first time what a male anal orgasm is.

XHamster 4 years ago

SISSY DRESS UP

64% 0:30 / 9:04

Clips4sale 1 year ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Sweet & Daaniel Private Show

60% HD 2:00 / 9:33

Sweet & Daaniel Private Show

Camster 3 weeks ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Guided JOI Session With Femdom Mistress

Guided JOI Session With Femdom Mistress

Pornicom 5 years ago

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 7 months ago

Prissy sissy dolly - Maid to be used

63% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years ago

Group Bi Training with My Three Girlfriends

Group Bi Training with My Three Girlfriends

XHamster 2 months ago

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Lesbian8 5 days ago

SISSY CUM EATING

SISSY CUM EATING

Amateur8 4 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 7 months ago

Stepmommy Turns YOU into a Little Bunny Sissy Bitch - Penny Barber Taboo

Stepmommy Turns YOU into a Little Bunny Sissy Bitch - Penny Barber Taboo

PornFreeNow 7 months ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 4 months ago

Cataleya Kirk Private Show

Cataleya Kirk Private Show

Camster 1 week ago

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

StiefMutter 1 week ago

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

XHamster 1 year ago

Sissy's Feminization

Sissy's Feminization

BigTitsLust 5 months ago

sissy joyce - goddess annie i love their helpless porn video

sissy joyce - goddess annie i love their helpless porn video

BDSMShip 1 year ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 6 months ago

Elizabeth Whiler Private Show

47% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Camster 3 years ago

Katharine Cane Party on Aug 8, 2026 - Part 3

65% 4K 2:00 / 8:46

Katharine Cane Party on Aug 8, 2026 - Part 3

Camster 3 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

PornFreeNow 7 months 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 1 year ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Bisexual Guide: Sissy Slut Slurps on Cock Gently for Hot Cum

Bisexual Guide: Sissy Slut Slurps on Cock Gently for Hot Cum

XXXXCum 1 year ago

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

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

XMilf 9 months ago

hottie blonde trains smooth boyfriend in hotel room

hottie blonde trains smooth boyfriend in hotel room

XHamster 3 years ago

Massive Cock Compilation: Who Can Swallow More Cum?

Massive Cock Compilation: Who Can Swallow More Cum?

XXXShake 4 years ago

Nobody's Gonna Save You - Anal Bondage with a Dominant Mistress and Submissive Slave

Nobody's Gonna Save You - Anal Bondage with a Dominant Mistress and Submissive Slave

JuicyVid 1 week ago

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

SortPorn 1 year ago

Katharine Cane Party on Aug 9, 2026 - Part 2

4K 2:00 / 22:38

Katharine Cane Party on Aug 9, 2026 - Part 2

Camster 2 weeks ago

U will eat his cum

U will eat his cum

SortPorn 4 years ago

Sissy cuckold trained to love cum and ruined orgasms by dominant mistress

Sissy cuckold trained to love cum and ruined orgasms by dominant mistress

XXXShake 3 years ago

Female POV - feel like a girl

Female POV - feel like a girl

XHamster 3 years ago

BBC Sissy Training #2

BBC Sissy Training #2

AbXXX 2 years ago

Jhanne Cherry Private Show

48% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Jhanne Cherry Private Show

60% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

Lesbian8 2 months ago

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

54% 1:00 / 10:40

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

Clips4sale 5 months ago

wife makes stranger cum and then her husband licks it up

wife makes stranger cum and then her husband licks it up

XHamster 1 year ago

Her Ebony Hand Chokes Your Sissy Throat Then Pegs You Until You Cum in Your Cage

Her Ebony Hand Chokes Your Sissy Throat Then Pegs You Until You Cum in Your Cage

AveXXX 3 weeks ago

Strict vintage femdom mistress trains her sissy slave in sensual submission

Strict vintage femdom mistress trains her sissy slave in sensual submission

Yesvids 1 month ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Cuckold Training 2 - Sissy Cuckold Watches While His New Wife Chokes On A Bbc

Cuckold Training 2 - Sissy Cuckold Watches While His New Wife Chokes On A Bbc

11Hentai 7 months ago

Randy Moore Fucks Lance Hart in the Ass with Strapon

Randy Moore Fucks Lance Hart in the Ass with Strapon

Fetishpapa 5 days ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 8 months ago

Sissy & cuckold training

53% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Yesvids 1 month ago

[823] Strap and Birch

71% 0:55 / 32:50

[823] Strap and Birch

Clips4sale 3 years ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 2 months ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Viky & Mateo Private Show

56% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 7 months ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Sweet & Daaniel Private Show

63% HD 2:00 / 9:33

Sweet & Daaniel Private Show

Flirt4Free 3 weeks ago

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

BDSMX 1 month ago

Miss Alika White - A-Z Sissy Training

Miss Alika White - A-Z Sissy Training

Nuvid 3 months ago

Get a Taste for Cum (Sissy Swallow Training Compilation)

Get a Taste for Cum (Sissy Swallow Training Compilation)

FreePorn8 5 years ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 2 years ago

14 days long Anal orgasm sissy calendar - TASK

56% 0:25 / 18:08

14 days long Anal orgasm sissy calendar - TASK

Clips4sale 1 year ago

Miss Alika White Size Queen Sissy Training

Miss Alika White Size Queen Sissy Training

YepTube 7 months ago

Elizabeth Whiler Private Show

50% HD 2:00 / 8:57

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

hands free cum in cage with new toy

hands free cum in cage with new toy

Fetishpapa 1 month ago

Grisha Mochka Private Show

56% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 2 months ago

Sissy joi with stockings

Sissy joi with stockings

PornFreeNow 2 weeks ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 10 months 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

Sissy Slave Training MyFreeShemale.com

Sissy Slave Training MyFreeShemale.com

Fapcat 4 years ago

Jhanne Cherry Private Show

Jhanne Cherry Private Show

Camster 1 year ago

ANAL training for my DIAPER slave

ANAL training for my DIAPER slave

XHamster 1 year ago

Obedient White Whore Worships BBC & Dicked down Hard

Obedient White Whore Worships BBC & Dicked down Hard

FreePorn8 4 years ago

Pantywearing Sissy JOI CEI

63% 0:30 / 8:46

Pantywearing Sissy JOI CEI

Clips 2 weeks ago

Mean Double Domination of the Caged Sissy Doxy Part 1

Mean Double Domination of the Caged Sissy Doxy Part 1

Amateur8 4 weeks ago

Two dominant goddesses teach sissy hotties to suck and swallow

Two dominant goddesses teach sissy hotties to suck and swallow

XHamster 2 years ago

Oriental Angel with Latex Hard Sex in the Dungeon

Oriental Angel with Latex Hard Sex in the Dungeon

Amateur8 1 month ago

Viky & Mateo Private Show

53% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 months ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 3 years ago

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

BDSMShip 1 year ago

Bi Encouragement - Serve Me and Alpha Cock

51% HD 1:01 / 12:47

Bi Encouragement - Serve Me and Alpha Cock

FapHouse 9 months ago

Let Me Ride You - P.o.v

63% 4K 2:00 / 4:32

Let Me Ride You - P.o.v

Flirt4Free 7 years ago

My Loser Beta Sissy Cuckold Jason

My Loser Beta Sissy Cuckold Jason

XHamster 5 months ago

Emily & Stesha Private Show

67% 4K 2:00 / 8:54

Emily & Stesha Private Show

Flirt4Free 5 months ago

U Will Suck Penis Bi-Sexual Encouragement Binaural Beats Erotic Audio Mesmerizing by Tara Smith

U Will Suck Penis Bi-Sexual Encouragement Binaural Beats Erotic Audio Mesmerizing by Tara Smith

SortPorn 4 years ago

Elizabeth Whiler Private Show

49% HD 2:00 / 59:39

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Manu Eyngri Private Show

HD 2:00 / 24:41

Manu Eyngri Private Show

Camster 2 weeks ago

Sexually Lascivious Sissy Caption Story – Quarantined With Black Friend!

Sexually Lascivious Sissy Caption Story – Quarantined With Black Friend!

Dafreeporn 3 years ago

Sissy Whore Brain Scrambler

HD 0:20 / 28:01

Sissy Whore Brain Scrambler

IWantClips 2 years ago

What a way to cum - OMG

What a way to cum - OMG

Amateur8 1 year ago

You Will Beg Me To Link You To This Video. Big Compilation.

You Will Beg Me To Link You To This Video. Big Compilation.

XHamster 3 years ago

PERMANENT FEMINIZATION- Femdom Goddess Worship Castration Penectomy Dirty Talk by Miss Faith Rae with Submissive Encouragement and Surgical Talk- HD 1080p MP4

63% HD 0:29 / 8:54

PERMANENT FEMINIZATION- Femdom Goddess Worship Castration Penectomy Dirty Talk by Miss Faith Rae with Submissive Encouragement and Surgical Talk- HD 1080p MP4

IWantClips 1 year ago

sissy chokes on food stuffed ass then gets face fucked raw

sissy chokes on food stuffed ass then gets face fucked raw

AveXXX 1 week ago

Hard pegging compilation with lots of cum on chest

Hard pegging compilation with lots of cum on chest

SortPorn 3 years ago

Helena Red Private Show

63% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Double Humiliation : Two Leather Mistress Train & Break Their Slave - part 1

HD 0:10 / 17:43

Double Humiliation : Two Leather Mistress Train & Break Their Slave - part 1

LoyalFans 3 weeks ago

Caged sissy gets femdom goddess sissygasm training

Caged sissy gets femdom goddess sissygasm training

AveXXX 3 weeks ago

Whip that sissy!

Whip that sissy!

XHamster 6 days ago

Bimbo sissy takes anal fisting instructions from dominant woman

Bimbo sissy takes anal fisting instructions from dominant woman

AveXXX 1 week ago

Katharine Cane Party on Jul 6, 2026 - Part 2

55% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Flirt4Free 1 month ago

New Sissy in Training (4K)

53% 4K 0:18 / 11:44

New Sissy in Training (4K)

Clips4sale 6 months ago

Triple Jizz Cum Slut 1080p ft Mistress Damazonia

68% HD 0:16 / 10:05

Triple Jizz Cum Slut 1080p ft Mistress Damazonia

Clips4sale 2 years ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

59% HD 0:39 / 16:47

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

FapHouse 1 month ago

Cock Sucking Sissy Training – FEMDOM EMPIRE FemDom

Cock Sucking Sissy Training – FEMDOM EMPIRE FemDom

IcePorn 2 months ago

Best Femdom Pegging Compilation by Dominafire

Best Femdom Pegging Compilation by Dominafire

XHamster 2 years ago

Emmalee Jones Uses Fuck Machine

66% 4K 2:00 / 4:17

Emmalee Jones Uses Fuck Machine

Flirt4Free 11 months ago

woman knows how to penetrate a man's ass pegging rimjob

woman knows how to penetrate a man's ass pegging rimjob

XHamster 3 years ago

Darsy Pearly Private Show

65% HD 2:00 / 9:56

Darsy Pearly Private Show

Camster 1 month ago

10 Anal Tasks CEI CBT Femdom Humiliation

64% HD 0:39 / 21:38

10 Anal Tasks CEI CBT Femdom Humiliation

FapHouse 2 months ago

Gape For Goddess 2

HD 0:15 / 21:21

Gape For Goddess 2

IWantClips 4 years ago

Not for Boring Couples - Vol 2

Not for Boring Couples - Vol 2

XHamster 3 weeks ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year ago

Angelica Swiss Party on Jul 4, 2026

64% HD 2:00 / 1:44:09

Angelica Swiss Party on Jul 4, 2026

Camster 1 month ago

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