Sissy Training - Porn Videos (148,390)

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

Bi Encouragement Training - Take 2 Of My Mans Cumshots

Bi Encouragement Training - Take 2 Of My Mans Cumshots

XHamster 1 month 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

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

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 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

Prissy sissy dolly - Maid to be used

63% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years 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

Cataleya Kirk Private Show

Cataleya Kirk Private Show

Camster 1 week ago

Sweet & Daaniel Private Show

60% HD 2:00 / 9:33

Sweet & Daaniel Private Show

Camster 3 weeks ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 1 month ago

Group Bi Training with My Three Girlfriends

Group Bi Training with My Three Girlfriends

XHamster 2 months ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

PornFreeNow 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

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Randy Moore Fucks Lance Hart in the Ass with Strapon

Randy Moore Fucks Lance Hart in the Ass with Strapon

Fetishpapa 4 days ago

Guided JOI Session With Femdom Mistress

Guided JOI Session With Femdom Mistress

Pornicom 5 years 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 CUM EATING

SISSY CUM EATING

Amateur8 4 years ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 7 months ago

Cock Sucking Sissy Training – FEMDOM EMPIRE FemDom

Cock Sucking Sissy Training – FEMDOM EMPIRE FemDom

IcePorn 2 months ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Elizabeth Whiler Private Show

47% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Camster 3 years ago

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

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

Lesbian8 4 days ago

Jessie Evans Private Show

Jessie Evans Private Show

Flirt4Free 2 weeks ago

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 7 months ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 10 months ago

[823] Strap and Birch

71% 0:55 / 32:50

[823] Strap and Birch

Clips4sale 3 years ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 4 months 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

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

hottie blonde trains smooth boyfriend in hotel room

hottie blonde trains smooth boyfriend in hotel room

XHamster 3 years ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

Lesbian8 1 year ago

Female POV - feel like a girl

Female POV - feel like a girl

XHamster 3 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

Pale babe moves her lips Slowly and Sucks BBC close-up

Pale babe moves her lips Slowly and Sucks BBC close-up

XGroovy 4 years ago

Sissy & cuckold training

53% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Sissy's Feminization

Sissy's Feminization

BigTitsLust 5 months ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year 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

Viky & Mateo Private Show

54% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 7 months ago

Lucie Arztin - Sissy Training

Lucie Arztin - Sissy Training

IcePorn 1 year ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 8 months 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

BBC Sissy Training #2

BBC Sissy Training #2

AbXXX 2 years ago

Miss Alika White Size Queen Sissy Training

Miss Alika White Size Queen Sissy Training

YepTube 7 months ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 6 months ago

Grisha Mochka Private Show

58% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 2 months ago

Miss Alika White - A-Z Sissy Training

Miss Alika White - A-Z Sissy Training

Nuvid 3 months ago

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 years ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 2 months ago

Elizabeth Whiler Private Show

49% HD 2:00 / 59:39

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Jhanne Cherry Private Show

60% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Femdom pegging with 8 inch strapon

Femdom pegging with 8 inch strapon

XHamster 9 months ago

Sissy joi with stockings

Sissy joi with stockings

PornFreeNow 2 weeks 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

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 cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 year ago

Edging and Sounding by Dominafire

65% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

ANAL training for my DIAPER slave

ANAL training for my DIAPER slave

XHamster 1 year ago

Wife Makes Husband Suck Her Lovers Cock Whilst She Masturbates

62% 0:39 / 6:57

Wife Makes Husband Suck Her Lovers Cock Whilst She Masturbates

FapHouse 1 year ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 2 years 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

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 2 weeks ago

Elizabeth Whiler Private Show

50% HD 2:00 / 8:57

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Get a Taste for Cum (Sissy Swallow Training Compilation)

Get a Taste for Cum (Sissy Swallow Training Compilation)

FreePorn8 5 years ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year ago

Oriental Angel with Latex Hard Sex in the Dungeon

Oriental Angel with Latex Hard Sex in the Dungeon

Amateur8 1 month ago

Pegged in Chastity - Screw your Butt Anal Jerk off Instructions with Messy Talk by Female-Dominator Nikki Kit

Pegged in Chastity - Screw your Butt Anal Jerk off Instructions with Messy Talk by Female-Dominator Nikki Kit

BigTitsLust 4 years ago

Massive Cock Compilation: Who Can Swallow More Cum?

Massive Cock Compilation: Who Can Swallow More Cum?

XXXShake 4 years ago

Sissy Slave Training MyFreeShemale.com

Sissy Slave Training MyFreeShemale.com

Fapcat 4 years 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

Bimbo sissy takes anal fisting instructions from dominant woman

Bimbo sissy takes anal fisting instructions from dominant woman

AveXXX 1 week 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

Sweet & Daaniel Private Show

63% HD 2:00 / 9:33

Sweet & Daaniel Private Show

Flirt4Free 3 weeks ago

Hard pegging compilation with lots of cum on chest

Hard pegging compilation with lots of cum on chest

SortPorn 3 years 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

We Love Spreading and Playing with Our Big Asses.

We Love Spreading and Playing with Our Big Asses.

XHamster 3 months ago

Sissy Whore Brain Scrambler

HD 0:20 / 28:01

Sissy Whore Brain Scrambler

IWantClips 2 years ago

My Loser Beta Sissy Cuckold Jason

My Loser Beta Sissy Cuckold Jason

XHamster 5 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

Lauren Newton Private Show

Lauren Newton Private Show

Camster 1 day ago

Manu Eyngri Private Show

HD 2:00 / 24:41

Manu Eyngri Private Show

Camster 2 weeks 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

Be obedient and spread your ass wide for me

Be obedient and spread your ass wide for me

AveXXX 1 week ago

Femdom Mistresse Domina V humiliates & fully feminizes chastity cuckold sissy sub serf w/ sph 1/three

Femdom Mistresse Domina V humiliates & fully feminizes chastity cuckold sissy sub serf w/ sph 1/three

FreePorn8 2 years 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

Bizarre Compilation - Screwing, Cumshots, Sucking Dong & Pegging

Bizarre Compilation - Screwing, Cumshots, Sucking Dong & Pegging

Dafreeporn 3 years 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

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 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

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

Viky & Mateo Private Show

53% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 months ago

I'm a dirty slave of my wife... she can do everything with me

I'm a dirty slave of my wife... she can do everything with me

XHamster 9 months ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

Katharine Cane Party on Jul 6, 2026 - Part 2

Katharine Cane Party on Jul 6, 2026 - Part 2

Flirt4Free 1 month 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

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 4 years ago

Not for Boring Couples - Vol 2

Not for Boring Couples - Vol 2

XHamster 2 weeks 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

What a way to cum - OMG

What a way to cum - OMG

Amateur8 1 year ago

Junior & Brittney Private Show

65% HD 2:00 / 4:02

Junior & Brittney Private Show

Flirt4Free 2 years ago

Angelica Swiss Party on Jul 4, 2026

61% HD 2:00 / 1:44:09

Angelica Swiss Party on Jul 4, 2026

Camster 1 month ago

Becoming a sissy

Becoming a sissy

Dafreeporn 6 years ago

Asmr Sensual Teasing Close up Blowjob

Asmr Sensual Teasing Close up Blowjob

XHamster 5 months ago

Gape For Goddess 2

HD 0:15 / 21:21

Gape For Goddess 2

IWantClips 4 years ago

Sandra Angell Private Show - Part 3

48% HD 2:00 / 43:27

Sandra Angell Private Show - Part 3

Flirt4Free 3 years ago

Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

Eporner 3 years ago

hands free cum in cage with new toy

hands free cum in cage with new toy

Fetishpapa 1 month ago

Elizabeth Whiler Private Show

60% HD 2:00 / 16:55

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Sissy Intake Exam: Mouth Training & MK Mark - HD

Sissy Intake Exam: Mouth Training & MK Mark - HD

LoyalFans 6 days ago

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