Sissy Training (147,648)

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

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 months ago

Dildo Dolly 2

58% HD 1:01 / 15:31

FapHouse 3 years ago

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

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Making You Soft Forever

59% HD 0:28 / 19:00

Making You Soft Forever

IWantClips 11 months ago

The sissy, his Wife & The Saleswoman - Kendra James and Star Nine Pantyhose Domination, Sissy Sluts, Double Domination, Sissy Training

60% HD 0:10 / 13:05

The sissy, his Wife & The Saleswoman - Kendra James and Star Nine Pantyhose Domination, Sissy Sluts, Double Domination, Sissy Training

LoyalFans 2 months ago

Sissy Slut Gets Strapon Experience - Full Version

Sissy Slut Gets Strapon Experience - Full Version

XHamster 4 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 2 weeks ago

Size Queen Sissy Boy Training with CEI

61% HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 1 month ago

Aroma Strapon Your Sissy Virginity Is Over

Aroma Strapon Your Sissy Virginity Is Over

FapHouse 1 week ago

Autumn Woods Party on Aug 17, 2026

HD 2:00 / 28:50

Autumn Woods Party on Aug 17, 2026

Camster 5 days ago

Femdom Republic Sissy Training And Feminisation a Feminine

Femdom Republic Sissy Training And Feminisation a Feminine

DrTuber 4 weeks ago

Hand Job Training the Bondage Pet

53% HD 0:39 / 12:21

Hand Job Training the Bondage Pet

FapHouse 2 months ago

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

68% 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

Lauren Newton Private Show

HD 2:00 / 11:56

Lauren Newton Private Show

Flirt4Free 1 week ago

Femdom POV Sissy Training Pleasure Him

49% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 4 months ago

Jen Holly Private Show

59% HD 2:00 / 4:52

Jen Holly Private Show

Camster 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

Hope Daylee Foot Job

68% HD 2:00 / 20:35

Hope Daylee Foot Job

Flirt4Free 8 years ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 1 month ago

Teaching My Cuckold - SNOWBALLING & HUMILIATION

65% 1:01 / 20:17

Teaching My Cuckold - SNOWBALLING & HUMILIATION

FapHouse 3 years ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

Sissy & cuckold training

53% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 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

Becoming a sissy

Becoming a sissy

FreePorn8 6 years ago

Katharine Cane Party on Aug 8, 2026 - Part 3

Katharine Cane Party on Aug 8, 2026 - Part 3

Flirt4Free 2 weeks ago

early morning upskirt

early morning upskirt

SortPorn 1 year ago

Femdom POV Sissy Training Pleasure Him

49% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 4 months ago

Kate Rhoades Private Show

61% 4K 2:00 / 7:04

Kate Rhoades Private Show

Camster 9 months ago

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

65% HD 1:01 / 10:37

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

FapHouse 1 year ago

Jen Holly Private Show

63% HD 2:00 / 7:30

Jen Holly Private Show

Camster 1 year ago

Extreme Sissy Cock Sucking !

55% HD 0:25 / 11:25

Extreme Sissy Cock Sucking !

IWantClips 2 months ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Total Transformation - HD

42% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 1 year 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 8 months ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 1 month ago

strp HEELS PANTYHOSE

strp HEELS PANTYHOSE

XHamster 5 months ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Camster 1 week ago

Best of Harmony Rose volume 4

Best of Harmony Rose volume 4

XHamster 1 year ago

Put this on for me now, my slut! - Sissy Training and Pantyhose Domination with Miss Adrastea

HD 0:10 / 12:14

Put this on for me now, my slut! - Sissy Training and Pantyhose Domination with Miss Adrastea

LoyalFans 1 month ago

How To Masturbate Like A Girl

HD 0:21 / 17:39

How To Masturbate Like A Girl

IWantClips 1 year ago

MY step BROTHER BECOMES MY step SISTER BLONDE SISSY. FEMINIZED step BROTHER. SISSIFICATION. PEGGING

Premium HD 13:00

MY step BROTHER BECOMES MY step SISTER BLONDE SISSY. FEMINIZED step BROTHER. SISSIFICATION. PEGGING

XVideosRed 3 years ago

Emily & Stesha Private Show

Emily & Stesha Private Show

Flirt4Free 4 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

Pegging His Ass and Giving Him a Sensual Handjob with a Prostate Massage

72% 1:01 / 16:56

Pegging His Ass and Giving Him a Sensual Handjob with a Prostate Massage

FapHouse 1 year ago

Best Femdom Pegging Compilation by Dominafire

Best Femdom Pegging Compilation by Dominafire

XHamster 2 years ago

Feminized Fucked Femdommed

50% HD 0:10 / 18:47

Feminized Fucked Femdommed

LoyalFans 1 year ago

milking after hard pegging. guy tastes mistress annette for the first time.

milking after hard pegging. guy tastes mistress annette for the first time.

PornBox 3 years ago

Squirting Right at You!

63% HD 2:00 / 40:51

Squirting Right at You!

Camster 14 years ago

Husband Turned Girlfriend Pt 5

61% HD 0:15 / 20:29

Husband Turned Girlfriend Pt 5

IWantClips 3 years ago

Femdom Republic Sissy Training Shoe Licking Mistress Dayana

Femdom Republic Sissy Training Shoe Licking Mistress Dayana

Nuvid 1 month ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

Sissy Training: Deep Black Strapon Throat Fuck, Paddle Cock Slaps & Cum Swallow

Sissy Training: Deep Black Strapon Throat Fuck, Paddle Cock Slaps & Cum Swallow

XHamster 3 months ago

Katryn Anal Training n. 3 with Lady Sofia

Katryn Anal Training n. 3 with Lady Sofia

XHamster 6 days ago

Emily & Stesha Private Show

69% 4K 2:00 / 8:54

Emily & Stesha Private Show

Flirt4Free 5 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

Knockin Da Boots All Night Long

4K 2:00 / 22:35

Knockin Da Boots All Night Long

Camster 2 months ago

Sissy Bitch Pegging Compilation. Femdom Chastity

Sissy Bitch Pegging Compilation. Femdom Chastity

BigTitsLust 2 years ago

Two Dominatrix Femdom Ritual Humiliation, Ballbusting, Slave Training, Feminization and Anal Punishment - French Pegging

Two Dominatrix Femdom Ritual Humiliation, Ballbusting, Slave Training, Feminization and Anal Punishment - French Pegging

XHamster 2 months ago

Aurora Ber Private Show

52% 4K 2:00 / 6:07

Aurora Ber Private Show

Flirt4Free 1 year ago

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

Lesbian8 1 year ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 4 years ago

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Lesbian8 6 months ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 8 months ago

Vilu Vidish Makes a Boy Into a Girl to Peg Him

Vilu Vidish Makes a Boy Into a Girl to Peg Him

XHamster 3 months ago

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 4 years ago

Size Queen Sissy Hunk Training with CEI

Size Queen Sissy Hunk Training with CEI

MatureTubeHere 2 weeks ago

Sissy Training in the Dungeon

55% HD 0:10 / 13:29

Sissy Training in the Dungeon

LoyalFans 2 years ago

MILF1838- Evil Cougars Sissify Stepson

67% HD 0:25 / 13:23

MILF1838- Evil Cougars Sissify Stepson

IWantClips 1 year ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 1 month ago

Taming My Bitch

Taming My Bitch

XHamster 2 weeks ago

Sissy Summer

60% HD 0:10 / 9:53

LoyalFans 2 months ago

Jen Holly Private Show

52% HD 2:00 / 4:45

Jen Holly Private Show

Flirt4Free 1 year ago

Miss Adrastea is riding your face while you’re in chastity

Miss Adrastea is riding your face while you’re in chastity

XHamster 5 years ago

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

XHamster 4 years ago

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

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

XHamster 1 month ago

Emmalee Jones Private Show

70% 4K 2:00 / 11:24

Emmalee Jones Private Show

Flirt4Free 3 months ago

Slave training in heat

Slave training in heat

XHamster 1 year ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 3 months ago

FIRST SISSY TRAINING ASSIGNMENT

FIRST SISSY TRAINING ASSIGNMENT

Itsrealamateurs 2 months ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

Amateur8 2 years ago

Jennas Suprise

XHamster 3 years ago

Unexpected sissy male climax .

Unexpected sissy male climax .

SortPorn 1 month ago

A Dominatrix Takes her Bath in Tights and Humiliates her Slave (Fetish ASMR) - Maitresse Julia Teaser

A Dominatrix Takes her Bath in Tights and Humiliates her Slave (Fetish ASMR) - Maitresse Julia Teaser

XHamster 3 years ago

Jessie Evans Private Show

Jessie Evans Private Show

Flirt4Free 1 week ago

A Sissy Type of Diet (standard Definition)

A Sissy Type of Diet (standard Definition)

FapHouse 1 month ago

Mean Wife locked me in chastity and mads to fuck her with a strap on

Mean Wife locked me in chastity and mads to fuck her with a strap on

XHamster 1 year ago

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 year ago

Her Mission Is to Take Him Unfathomable with Her Siswet From Mrhankeystoys

Her Mission Is to Take Him Unfathomable with Her Siswet From Mrhankeystoys

Amateur8 2 weeks ago

Sissy Mesmerize Sessions

56% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 3 years ago

Miss Brit Slave Training of Sofie Marie

Miss Brit Slave Training of Sofie Marie

XHamster 5 months ago

best fucking huge strapon sissy anal. this slut is ready to fuck. sissy fucked in chastity

HD 0:30 / 11:06

best fucking huge strapon sissy anal. this slut is ready to fuck. sissy fucked in chastity

PornBox 3 years ago

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

78% HD 1:01 / 7:58

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

FapHouse 1 year ago

YOU're Such a Sexy Sissy Doxy for Me

YOU're Such a Sexy Sissy Doxy for Me

PornFreeNow 1 week ago

Sissy Feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom POV domination

Sissy Feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom POV domination

Deviants 3 years 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 6 months ago

BBC Sissy FPOV Fellatio Mindwash - Femdom - Female-Dominator Alexa and Father Jay

BBC Sissy FPOV Fellatio Mindwash - Femdom - Female-Dominator Alexa and Father Jay

Amateur8 4 years ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 2 years ago

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 10 months ago

Katharine Cane Party on Aug 22, 2026 - Part 2

4K 2:00 / 1:01:35

Katharine Cane Party on Aug 22, 2026 - Part 2

Camster 2 days ago

Strapon Pegging in Hotel

Strapon Pegging in Hotel

XHamster 1 year ago

POV Two Milfs in Bodystocking Strap-On Domination

POV Two Milfs in Bodystocking Strap-On Domination

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

Zoey Evans Premiere Show

64% HD 2:00 / 4:56

Zoey Evans Premiere Show

Camster 1 month ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

Merciless big beautiful woman Female-dom Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Urinate Drinking!

Merciless big beautiful woman Female-dom Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Urinate Drinking!

Lesbian8 1 month ago

U're Such a Hawt Sissy Wench for Me

U're Such a Hawt Sissy Wench for Me

Lesbian8 1 week ago

2 Lesbians Taunt a Submissive Man and Fuck in Front of Him

HD 0:39 / 22:03

2 Lesbians Taunt a Submissive Man and Fuck in Front of Him

FapHouse 4 weeks ago

Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

XHamster 3 years ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 4 years ago

Sissy training with Femdom Mistress Tangent

Sissy training with Femdom Mistress Tangent

Xozilla 8 years ago

Bisexual husband gets fucked by three strapons

Bisexual husband gets fucked by three strapons

XHamster 2 years ago

CUCKOLD CUMS IN PANTIES LIKE A GIRL

CUCKOLD CUMS IN PANTIES LIKE A GIRL

XHamster 4 years ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

XHamster 2 years 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

BDSMX 7 months ago

Your new Sexuality as A Sissy: EP5 Turning a Wanker into a Slave - Mistress Julia Femdom

Your new Sexuality as A Sissy: EP5 Turning a Wanker into a Slave - Mistress Julia Femdom

XHamster 2 years ago

Ashley Sinn Private Show

53% 4K 2:00 / 7:22

Ashley Sinn Private Show

Camster 11 months ago

1 2 3 4 5

147,648 results found

Related searches

Narrow your search

sissy anal training

Categories Pornstars

Parents

Stocking-tease.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Stocking-tease.com. All rights reserved.

© 2026 Stocking-tease.com. All rights reserved.