Sissy Training (148,375)

The best and newest sissy training videos

Whored Out Office Sissy - Pegging POV with Elle Eros

66% HD 0:39 / 8:17

Whored Out Office Sissy - Pegging POV with Elle Eros

FapHouse 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

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

61% HD 0:39 / 8:39

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

FapHouse 1 year ago

Peg Curious - Sharing My Man W Roommate

58% 1:01 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 1 month ago

Diva Belle Private Show

64% HD 2:00 / 4:27

Diva Belle Private Show

Camster 1 month ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Baby in paradise part 1

63% HD 0:39 / 9:01

Baby in paradise part 1

FapHouse 4 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

Wife makes husband suck her lovers cock whilst she masturbates

Wife makes husband suck her lovers cock whilst she masturbates

XHamster 1 year ago

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

55% HD 0:10 / 15:31

Sissy Transformation and Training Go Girly and suck cock! Goddess Vivien guides you to get dressed in a frilly pink sissy outfit and suck dick

LoyalFans 1 year ago

Peg Curious - Sharing My Man W Roommate

74% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 1 month ago

Sissy Gets Caught

66% HD 0:10 / 9:26

Sissy Gets Caught

LoyalFans 8 months ago

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

XHamster 1 year ago

Feminization Retreat: A Weekend of Use, Humiliation, and Unholy Obedience - Available only on LF!

47% HD 0:10 / 25:08

Feminization Retreat: A Weekend of Use, Humiliation, and Unholy Obedience - Available only on LF!

LoyalFans 1 year ago

Andromeda Cute Private Show

HD 2:00 / 20:53

Andromeda Cute Private Show

Camster 3 weeks ago

Femdom Humiliation - Oops, I've Made You Gay!

44% HD 1:01 / 18:20

Femdom Humiliation - Oops, I've Made You Gay!

FapHouse 4 months ago

Kandi More & Jamer Private Show

57% HD 2:00 / 5:32

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

Viky & Mateo Private Show

54% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 7 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

Reminding Her Why I'm the StepDaddy

Reminding Her Why I'm the StepDaddy

LoyalFans 7 months ago

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

XHamster 8 months ago

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 years ago

Pantyhose Aerobics Class For Sissies

61% HD 0:10 / 15:12

Pantyhose Aerobics Class For Sissies

LoyalFans 1 year ago

Fist Fuck Training Sissy Sluts Ass

Fist Fuck Training Sissy Sluts Ass

BDSMX 4 years ago

Jen Holly Private Show

Jen Holly Private Show

Camster 1 year ago

Grooming care for chastity sissy

Grooming care for chastity sissy

XHamster 6 months ago

Chaste & Sissified

43% HD 0:10 / 7:19

Chaste & Sissified

LoyalFans 3 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

The Last Step: Convincing You to Become My Feminized Cocksucker

The Last Step: Convincing You to Become My Feminized Cocksucker

XHamster 3 months ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years ago

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

XHamster 2 years ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 6 months ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Your First Gloryhole Cock - Bi Encouraged Suck and Swallow

54% 0:39 / 10:59

Your First Gloryhole Cock - Bi Encouraged Suck and Swallow

FapHouse 1 year ago

Bella Brookz Private Show

49% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Wear These for Step-mommy!

Wear These for Step-mommy!

XHamster 1 year ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Busty British MILF pegs office faggot with her huge strap-on

Busty British MILF pegs office faggot with her huge strap-on

AveXXX 4 days ago

”Bi-Curious Bro Gets A Sissy Sandwich”

”Bi-Curious Bro Gets A Sissy Sandwich”

TransHero 8 months ago

wife makes stranger cum and then her spouse licks it up

wife makes stranger cum and then her spouse licks it up

SortPorn 1 month ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

58% 0:39 / 25:09

JOI Echo in Latex with My Big Black Strapon - Luna Doll

FapHouse 10 months ago

SISSIFYME. A SISSY FOR LIFE

SISSIFYME. A SISSY FOR LIFE

BigTitsLust 1 year ago

Training You, My Sissy, to Love Cock

57% HD 0:10 / 10:14

Training You, My Sissy, to Love Cock

LoyalFans 2 months ago

Sissy Slut Trained And Spit Roasted

Sissy Slut Trained And Spit Roasted

PePorn 10 months ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 4 months ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

Mirror View- FIRM Pegging

54% HD 0:25 / 13:11

Mirror View- FIRM Pegging

IWantClips 2 years ago

Helena Red Private Show

63% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

The Final Transformation Part 2

The Final Transformation Part 2

Dafreeporn 4 months ago

BBC Sissy FPOV Blow Job Mindwash - Femdom - Female-Taskmaster Alexa and Father Jay

BBC Sissy FPOV Blow Job Mindwash - Femdom - Female-Taskmaster Alexa and Father Jay

Dafreeporn 4 years ago

Veronica Mendez Private Show

HD 2:00 / 22:16

Veronica Mendez Private Show

Camster 3 days ago

Slave training in heat

Slave training in heat

Lesbian8 1 year ago

!!! MUST WATCH!!! Perfectly ruined orgasm

!!! MUST WATCH!!! Perfectly ruined orgasm

XHamster 5 years ago

Julie and Liza's Latex Doll

68% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 6 months ago

Bella Brookz Private Show

45% HD 2:00 / 14:02

Bella Brookz Private Show

Flirt4Free 3 years ago

Red Lips Tease and Pussyplay

56% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Camster 3 years ago

alexis amadahy and jade sissy training and strap on

alexis amadahy and jade sissy training and strap on

PornOne 8 years ago

German Mastix Silvia trains her sissy maid

German Mastix Silvia trains her sissy maid

AbXXX 13 years ago

Leather Weather! The Best Leather

Leather Weather! The Best Leather

Some.Porn 1 year ago

Sissy Twerks for BNWO

Sissy Twerks for BNWO

LoyalFans 1 year ago

Feminised and fucked. HARD PEGGING

57% HD 0:25 / 12:02

Feminised and fucked. HARD PEGGING

IWantClips 2 years ago

Dare to Come Closer?

64% HD 2:00 / 2:20

Dare to Come Closer?

Camster 1 year ago

Bella Brookz Private Show

52% HD 2:00 / 9:01

Bella Brookz Private Show

Camster 3 years ago

Your Slutty Sissy Fantasy 2

HD 0:15 / 20:12

Your Slutty Sissy Fantasy 2

IWantClips 2 months ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Experimental Alpha Supplements

HD 0:31 / 18:02

Experimental Alpha Supplements

Clips4sale 1 year ago

Fun Feminization

52% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 year ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 8 months ago

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

57% 0:40 / 9:22

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

Clips4sale 8 months ago

10 Depraved Tasks No Limits - Femom POV

42% HD 1:01 / 14:02

10 Depraved Tasks No Limits - Femom POV

FapHouse 4 months ago

Feminisation Bundle (720p)

68% HD 0:36 / 40:44

Feminisation Bundle (720p)

Clips4sale 1 year ago

Mistress Lady Renee - Making you dress - mp4

72% 0:16 / 14:03

Mistress Lady Renee - Making you dress - mp4

Clips4sale 1 year ago

Faggot Maker - make me bi - bi encouragement - CEI - cock worship - faggot training - sissy training - imposed bi - big cock - joi

64% HD 0:10 / 6:32

Faggot Maker - make me bi - bi encouragement - CEI - cock worship - faggot training - sissy training - imposed bi - big cock - joi

LoyalFans 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

Akira Sissifies Jessica (HD MP4)

57% HD 0:26 / 13:00

Akira Sissifies Jessica (HD MP4)

Clips4sale 11 months ago

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

69% HD 1:01 / 11:28

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

FapHouse 2 months ago

Special feminization training with your girlfriend Yae Miko (Femdom JOI)

Special feminization training with your girlfriend Yae Miko (Femdom JOI)

XHamster 2 months ago

Femdom Republic Sissy Training And Feminisation a Feminine

Femdom Republic Sissy Training And Feminisation a Feminine

DrTuber 1 month ago

The Final Step: Convincing U to Become My Feminized Cocksmoker

The Final Step: Convincing U to Become My Feminized Cocksmoker

BigTitsLust 3 months ago

Self Facial Training for my Cuckold Sissy

Self Facial Training for my Cuckold Sissy

Amateur8 3 years ago

Bella Brookz Private Show

63% HD 2:00 / 18:56

Bella Brookz Private Show

Camster 3 years ago

Super Girly JOI

HD 0:10 / 13:08

Super Girly JOI

LoyalFans 2 weeks ago

Sissy Mouth-Serf Training: Eat Each Load

Sissy Mouth-Serf Training: Eat Each Load

SortPorn 10 months ago

Harmoni Kalifornia's Sissy Spouse Mr. B***e (Pip) Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Spouse Mr. B***e (Pip) Experiences Anal Training from Sean

FreePorn8 11 months ago

Hailey Roses Private Show

49% HD 2:00 / 24:20

Hailey Roses Private Show

Flirt4Free 3 years ago

BBC JOI for Sissies

BBC JOI for Sissies

XHamster 2 months ago

Male to Feminized Sissy Bondage Transformation

59% 0:12 / 12:32

Male to Feminized Sissy Bondage Transformation

Clips4sale 2 years ago

Hailey Roses Private Show

Hailey Roses Private Show

Flirt4Free 3 years ago

JOI Anal session training, sissy lesson - Sammy Altham

JOI Anal session training, sissy lesson - Sammy Altham

XHamster 4 months ago

Hailey Roses Private Show

60% HD 2:00 / 24:20

Hailey Roses Private Show

Camster 3 years ago

Femdom Republic Sissy Training Shoe Licking Mistress Dayana

Femdom Republic Sissy Training Shoe Licking Mistress Dayana

Nuvid 1 month ago

Diaper Sissy Gets Changed, Edged and Denied!

64% HD 0:29 / 20:06

Diaper Sissy Gets Changed, Edged and Denied!

Clips4sale 1 year ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 1 month ago

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 4 years ago

Real Dick VS Sissy Dick - SPH

60% 0:23 / 3:30

Real Dick VS Sissy Dick - SPH

Clips4sale 3 years ago

hands free cum in cage with new toy

hands free cum in cage with new toy

Fetishpapa 4 weeks ago

Your Bully Bimbotized Us WMV - MILF StepMom Lacey Royce Has Been Turned Into A Slutty Bimbo By Your Bully - Mesmerizing Mind Fuck Transformation Slut Training Fantasy

4K 1:00 / 25:12

Your Bully Bimbotized Us WMV - MILF StepMom Lacey Royce Has Been Turned Into A Slutty Bimbo By Your Bully - Mesmerizing Mind Fuck Transformation Slut Training Fantasy

Clips4sale 1 year ago

My sissy slut get strapon fucking

My sissy slut get strapon fucking

Clips4sale 2 years ago

Mistress Fatale's sissy training

38% HD 0:10 / 22:42

Mistress Fatale's sissy training

LoyalFans 3 years ago

Cock Slut

57% 4K 0:19 / 9:55

Clips4sale 2 years ago

XXL-SCHWANZ für SISSY! GERMAN

57% 0:11 / 6:14

XXL-SCHWANZ für SISSY! GERMAN

Clips4sale 3 years ago

Sissy Dirty Sex and a Disgusting Punishment in a Diaper

Sissy Dirty Sex and a Disgusting Punishment in a Diaper

XVideos 1 week ago

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

57% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 year ago

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

60% HD 0:39 / 9:43

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

FapHouse 1 month ago

DominaFire in latex pegging with huge strapon

DominaFire in latex pegging with huge strapon

FapHouse 3 years ago

Dominafire Pegging Compilation

Dominafire Pegging Compilation

FapHouse 2 years ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years ago

Adara Smith & Elver Rodriguez Private Show

62% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 3 years ago

Big Ass Worship Jerk Off Instructions

Big Ass Worship Jerk Off Instructions

Katestube 4 years ago

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

FapHouse 1 month ago

FIRST SISSY TRAINING ASSIGNMENT

FIRST SISSY TRAINING ASSIGNMENT

Itsrealamateurs 2 months ago

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

63% HD 0:15 / 5:13

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

PornBox 3 years ago

Suck Your Friends Cock with Me

Suck Your Friends Cock with Me

FapHouse 6 months ago

Ares & Adara Private Show

61% HD 2:00 / 6:43

Ares & Adara Private Show

Camster 1 year ago

Sissy Anal Training by Domina Fire

64% HD 1:01 / 11:29

Sissy Anal Training by Domina Fire

FapHouse 3 years ago

Sissy Slut BBC Training For Cuckolds

Sissy Slut BBC Training For Cuckolds

Pornicom 5 years ago

Sissy Tasks 2 - sissificiation feminization bimbofication sissy training bimbo feminize femdom domme

Sissy Tasks 2 - sissificiation feminization bimbofication sissy training bimbo feminize femdom domme

Itsrealamateurs 1 month ago

BBC Faggot Brainfuck

56% HD 0:24 / 11:11

BBC Faggot Brainfuck

IWantClips 2 months ago

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