Sissy Training (153,234)

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Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 منذ أعوام

Bi Humiliation & Cum Clean up with a Female Audience

51% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 منذ أعوام

Submissive Sluts volume 4

Submissive Sluts volume 4

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Bi Encouragement Training - Take 2 Of My Mans Cumshots

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Asian Mistress Dominafire Trains Her White Submissive Slave with Pegging

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Suck Cock and Swallow Hot Cum - Obey Your Mistress

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Jhanne Cherry Private Show

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Electra Joness Party on Jul 27, 2026 - Part 11

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Electra Joness Party on Jul 27, 2026 - Part 11

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Ruth Oliver Private Show

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Emily & Stesha Private Show

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Rubber Sissy Training High Heels, Boots & Punishment

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Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

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My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

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Elizabeth Whiler Private Show

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Elizabeth Whiler Private Show

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PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

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

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Junior & Brittney Private Show

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Junior & Brittney Private Show

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Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

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Sissy Dress-up Encouragement

55% HD 0:39 / 9:19

Sissy Dress-up Encouragement

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Cuckold 2 (lick My Toilet Clean!)

64% HD 1:01 / 5:36

Cuckold 2 (lick My Toilet Clean!)

FapHouse 1 منذ أعوام

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Sissy Kendall Anal Training & Slave Affirmations

58% HD 1:01 / 10:20

Sissy Kendall Anal Training & Slave Affirmations

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65% HD 0:39 / 10:19

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

FapHouse 1 منذ أيام

Sissy Training - Teaching My Friend How to Give a Blowjob

65% HD 1:01 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

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Step-mommy's Forever 2

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Step-mommy's Forever 2

FapHouse 2 منذ أسابيع

Pussy Eating Sissy (with CEI)

63% HD 0:39 / 10:01

Pussy Eating Sissy (with CEI)

FapHouse 1 منذ أعوام

Blonde Sex Slave Inseminated in Steel Shackles

Blonde Sex Slave Inseminated in Steel Shackles

XHamster 4 منذ أيام

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 منذ أعوام

Abril Newton Private Show

57% 4K 2:00 / 12:56

Abril Newton Private Show

Camster 11 منذ أشهر

Give up Your Life to Serve Me

66% HD 1:01 / 11:39

Give up Your Life to Serve Me

FapHouse 2 منذ أسابيع

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

XHamster 11 منذ أشهر

"Ultimate co- erced Bi BBC sissy cuck humiliation training" [18.49 minutes]

66% HD 0:10 / 18:49

"Ultimate co- erced Bi BBC sissy cuck humiliation training" [18.49 minutes]

LoyalFans 2 منذ أسابيع

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

51% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 9 منذ أشهر

Sunday Humiliation for Sissy husband Full

Sunday Humiliation for Sissy husband Full

XHamster 1 منذ أعوام

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 2 منذ أسابيع

Sissy Academy Part 6 - Sissy's Taste of Heaven

53% HD 0:39 / 5:55

Sissy Academy Part 6 - Sissy's Taste of Heaven

FapHouse 2 منذ أشهر

Group Bi Training with My Three Girlfriends

HD 1:01 / 22:44

Group Bi Training with My Three Girlfriends

FapHouse 6 منذ أيام

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 منذ أعوام

Be a Real Nylon Slut for Me! - Femdom POV with Strapon, Slut Training, Pantyhose Domination, Jerk off and Cum Eating Instruction

63% HD 1:01 / 17:40

Be a Real Nylon Slut for Me! - Femdom POV with Strapon, Slut Training, Pantyhose Domination, Jerk off and Cum Eating Instruction

FapHouse 3 منذ أشهر

Fun Feminization

52% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 منذ أعوام

Edging and Sounding by Dominafire

65% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 منذ أعوام

Hospitality Whores (full scene 4k)

52% 4K 0:30 / 42:01

Hospitality Whores (full scene 4k)

IWantClips 2 منذ أعوام

Sissy Kendall Anal Training & Slave Affirmations

53% HD 0:39 / 10:20

Sissy Kendall Anal Training & Slave Affirmations

FapHouse 5 منذ أشهر

Cruel BBW Goddess Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piss Drinking!

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XHamster 3 منذ أشهر

Peg Curious - Sharing My Man W Roommate

57% 1:01 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 2 منذ أشهر

Alpha Couple Teaches How to Suck Cock

60% HD 0:39 / 11:53

Alpha Couple Teaches How to Suck Cock

FapHouse 1 منذ أعوام

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

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Double Sissy Discipline

63% HD 0:39 / 12:34

Double Sissy Discipline

FapHouse 10 منذ أشهر

Your New Life as My Free Use Sissy

45% HD 0:39 / 16:13

Your New Life as My Free Use Sissy

FapHouse 6 منذ أشهر

Sissy Chastity Cuckold Humiliation, Hotwife Locks Her Caged Sissy Dildo Dummy

HD 0:39 / 19:20

Sissy Chastity Cuckold Humiliation, Hotwife Locks Her Caged Sissy Dildo Dummy

FapHouse 4 منذ أيام

Today we practice tying silk scarves

Today we practice tying silk scarves

FapHouse 4 منذ أعوام

insanely hot huge pegging compilation #2

insanely hot huge pegging compilation #2

PornBox 1 منذ أسابيع

Viky & Mateo Private Show

52% HD 2:00 / 4:35

Viky & Mateo Private Show

Flirt4Free 7 منذ أشهر

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

70% HD 0:39 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 3 منذ أيام

Poor Cuckold: the Wedding Anniversary

58% HD 0:39 / 36:28

Poor Cuckold: the Wedding Anniversary

FapHouse 3 منذ أعوام

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 منذ أشهر

Gape For Goddess 2

HD 0:15 / 21:21

Gape For Goddess 2

IWantClips 4 منذ أعوام

Not for Boring Couples - Vol 2

Not for Boring Couples - Vol 2

XHamster 4 منذ أسابيع

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

66% HD 1:01 / 20:49

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

FapHouse 5 منذ أيام

Sissy Training in Chastity

69% HD 1:01 / 9:54

Sissy Training in Chastity

FapHouse 1 منذ أعوام

Sissy Training - Teaching My Friend How to Give a Blowjob

60% HD 0:39 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 2 منذ أعوام

Jhanne Cherry Private Show

54% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 11 منذ أشهر

Husband Turned Girlfriend Pt 5

60% HD 0:15 / 20:29

Husband Turned Girlfriend Pt 5

IWantClips 3 منذ أعوام

Sissy training with strap-on pin-up curvy Mistress Arya Grander

Sissy training with strap-on pin-up curvy Mistress Arya Grander

FapHouse 6 منذ أيام

Dressed up in Gloss to Suck My Cock

HD 0:39 / 10:34

Dressed up in Gloss to Suck My Cock

FapHouse 2 منذ أيام

Anal Training and First Time Fisting

HD 0:39 / 10:19

Anal Training and First Time Fisting

FapHouse 2 منذ أعوام

Katharine Cane Party on Jul 6, 2026 - Part 2

56% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Flirt4Free 2 منذ أشهر

Zoey Evans Private Show

67% HD 2:00 / 48:47

Zoey Evans Private Show

Flirt4Free 1 منذ أعوام

Vilu Vidish Makes a Boy Into a Girl to Peg Him

Vilu Vidish Makes a Boy Into a Girl to Peg Him

XHamster 4 منذ أشهر

Useless sissy maid given a caning in the garden by Nikki & Aveena WL1772

60% 0:11 / 19:34

Useless sissy maid given a caning in the garden by Nikki & Aveena WL1772

Clips4sale 1 منذ أعوام

Peg Curious - Sharing My Man W Roommate

71% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 2 منذ أشهر

Cuckold Husband and His Ass and Lips Kellyaerick

63% HD 0:39 / 2:39

Cuckold Husband and His Ass and Lips Kellyaerick

FapHouse 2 منذ أعوام

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

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

XHamster 1 منذ أعوام

Sissy training with Femdom Mistress Tangent

Sissy training with Femdom Mistress Tangent

XHamster 9 منذ أعوام

Your Slutty Sissy Fantasy 2

HD 0:15 / 20:12

Your Slutty Sissy Fantasy 2

IWantClips 2 منذ أشهر

Femdom POV Sissy Training Pleasure Him

46% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 منذ أشهر

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

HD 0:39 / 17:26

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

FapHouse 2 منذ أيام

52% HD 1:01 / 11:41

Brand New World Order

FapHouse 1 منذ أسابيع

Grooming care for chastity sissy

Grooming care for chastity sissy

XHamster 6 منذ أشهر

Kitchen Session with Katharine

64% HD 2:00 / 1:34:09

Kitchen Session with Katharine

Camster 8 منذ أعوام

Electra Joness Party on Apr 13, 2026 - Part 3

50% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 4 منذ أشهر

Whip and Fuck the Slut

67% HD 0:39 / 9:19

Whip and Fuck the Slut

FapHouse 2 منذ أعوام

Emmalee Jones Talks Dirty

Emmalee Jones Talks Dirty

Camster 11 منذ أشهر

Sissy Spreads Wide

HD 0:17 / 11:57

Sissy Spreads Wide

IWantClips 2 منذ أعوام

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 منذ أعوام

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 منذ أعوام

Labella Slays Dick on Crossdressing Big Dick Sissy

Labella Slays Dick on Crossdressing Big Dick Sissy

XHamster 4 منذ أشهر

Cock Worship For Sissies

57% HD 0:15 / 21:36

Cock Worship For Sissies

IWantClips 2 منذ أشهر

Chastity tutorial - how to wear a chastity cage - part 1

Chastity tutorial - how to wear a chastity cage - part 1

XHamster 7 منذ أشهر

Pissing CFNM domina punishes sissy in BDSM lesson

Pissing CFNM domina punishes sissy in BDSM lesson

Some.Porn 1 منذ أعوام

The Hard Questions: Will I Sissify You? Potential Sissy Training with Rebelle Hart

The Hard Questions: Will I Sissify You? Potential Sissy Training with Rebelle Hart

IWantClips 2 منذ أشهر

Teasing his Butt Hole and Dick & balls

Teasing his Butt Hole and Dick & balls

XHamster 1 منذ أعوام

hard, deep, passionate pegging

hard, deep, passionate pegging

XHamster 3 منذ أيام

GUARANTEED SHOW AT 111 CREDITS INCLUDES: NAKED, BLOW JOB, FINGERING, RIDING AND MORE SEXY SQUIRT ORGASM SHOW AT GOAL 700 CREDITS🔥 🥵💦WHO WANTS TO BE MY GROUP KING

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Camster 1 منذ أسابيع

Emily & Stesha Private Show

61% 4K 2:00 / 9:06

Emily & Stesha Private Show

Camster 4 منذ أشهر

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

70% HD 2:00 / 4:53

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

Flirt4Free 1 منذ أعوام

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

77% HD 1:01 / 5:45

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

FapHouse 3 منذ أشهر

Rough Triple Anal Ride for Our Little Sissy

Premium HD 12:27

Rough Triple Anal Ride for Our Little Sissy

Sheer 2 منذ أسابيع

How Do I Wake up My Slave? by Pegging, of Course - Femdom Maitresse Julia

How Do I Wake up My Slave? by Pegging, of Course - Femdom Maitresse Julia

FapHouse 3 منذ أعوام

Elizabeth Whiler Private Show

53% HD 2:00 / 16:55

Elizabeth Whiler Private Show

Flirt4Free 3 منذ أعوام

Sex Doll Has Arrived

HD 0:39 / 32:44

Sex Doll Has Arrived

FapHouse 1 منذ أعوام

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 7 منذ أشهر

Lynna Bun Private Show

Lynna Bun Private Show

Camster 1 منذ أعوام

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 4 منذ أعوام

Elizabeth Whiler Private Show

60% HD 2:00 / 4:23

Elizabeth Whiler Private Show

Camster 3 منذ أعوام

Open your slutty mouth! - Sissy Training with Strap On and Jerk Off Instruction with Miss Adrastea

HD 0:10 / 12:56

Open your slutty mouth! - Sissy Training with Strap On and Jerk Off Instruction with Miss Adrastea

LoyalFans 1 منذ أسابيع

BBW Domina Fists & Pegs the Butthole Of Her Masked Sub, Then Lets the Sissy Man Fist Her Cunt

BBW Domina Fists & Pegs the Butthole Of Her Masked Sub, Then Lets the Sissy Man Fist Her Cunt

XGroovy 1 منذ أعوام

Intense strapon training sessions with dominant women and submissive men

Intense strapon training sessions with dominant women and submissive men

Yesvids 1 منذ أسابيع

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 2 منذ أشهر

Bi Encouragement - Serve Me and Alpha Cock

51% HD 1:01 / 12:47

Bi Encouragement - Serve Me and Alpha Cock

FapHouse 9 منذ أشهر

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 منذ أعوام

Size Queen Sissy Boy Training with CEI

Size Queen Sissy Boy Training with CEI

XHamster 1 منذ أشهر

Strip Me Down and Tease My Pussy

Strip Me Down and Tease My Pussy

Camster 3 منذ أعوام

Leena Sky Private Show

Leena Sky Private Show

Flirt4Free 3 منذ أعوام

The installation of the rubber doll - Sissy Training

The installation of the rubber doll - Sissy Training

XHamster 3 منذ أعوام

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

51% HD 1:01 / 9:48

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

FapHouse 10 منذ أشهر

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