Sissy Training (155,043)

The best and newest sissy training videos

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 3 months ago

BUNS BUNNY INFINITE POV Teasing Asshole Beautiful Natural Ass Wife

Premium HD 2:37

BUNS BUNNY INFINITE POV Teasing Asshole Beautiful Natural Ass Wife

Sheer 1 week ago

Elizabeth Whiler Private Show

52% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 4 years ago

Mad Scientist Gender Transformation Fantasy

58% HD 1:01 / 22:33

Mad Scientist Gender Transformation Fantasy

FapHouse 2 weeks ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years ago

Blowjob training for sissy maid

61% HD 0:20 / 13:43

Blowjob training for sissy maid

QueensOfKink 2 months ago

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 year ago

Emily & Stesha Private Show

4K 2:00 / 12:14

Emily & Stesha Private Show

Flirt4Free 5 months ago

Sissy Date Night

52% 1:01 / 19:30

Sissy Date Night

FapHouse 2 months 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

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 3 months ago

Feminized Fucked Femdommed

50% HD 0:10 / 18:47

Feminized Fucked Femdommed

LoyalFans 1 year ago

BBC JOI for Sissies

BBC JOI for Sissies

XHamster 3 months ago

Valexie Lux Private Show

58% 4K 2:00 / 5:23

Valexie Lux Private Show

Flirt4Free 3 weeks ago

Tori Mcqueen & Nina Lovez Private Show

65% HD 2:00 / 5:44

Tori Mcqueen & Nina Lovez Private Show

Flirt4Free 3 weeks ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

XHamster 2 years ago

Alesia Sin Party on Jul 26, 2026 - Part 3

4K 2:00 / 2:16:29

Alesia Sin Party on Jul 26, 2026 - Part 3

Flirt4Free 2 months ago

SISSY SLUT FUCKED HARD by DominaFire

SISSY SLUT FUCKED HARD by DominaFire

XHamster 4 years ago

Kate Rhoades Private Show

55% 4K 2:00 / 4:20

Kate Rhoades Private Show

Flirt4Free 11 months ago

Femdom Republic Sissy Training And Feminisation a Feminine

Femdom Republic Sissy Training And Feminisation a Feminine

DrTuber 2 months ago

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

64% HD 0:10 / 15:54

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

LoyalFans 7 months ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

XHamster 2 weeks 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

54% 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

Miss Brit Slave Training of Sofie Marie

Miss Brit Slave Training of Sofie Marie

XHamster 7 months ago

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

XHamster 4 years ago

NEW CONTENT! The Training Of Sissy Cum Bucket By Ruby Onyx

72% 4K 0:38 / 13:23

NEW CONTENT! The Training Of Sissy Cum Bucket By Ruby Onyx

Clips4sale 1 year ago

Medical Transformation of Sissy Doll Prague

63% 4K 0:17 / 8:54

Medical Transformation of Sissy Doll Prague

Clips4sale 2 months ago

How to be properly trained by Ms. Amanda

How to be properly trained by Ms. Amanda

Xfeed 3 weeks ago

Your Owner Gives You Surgical Body Modifications

Your Owner Gives You Surgical Body Modifications

XHamster 3 weeks ago

Jennas Suprise

XHamster 3 years ago

Bella Brookz Private Show

53% HD 2:00 / 7:57

Bella Brookz Private Show

Flirt4Free 3 years ago

Mistress Susi - the Straight Slaves First Sissy Blowjob

Mistress Susi - the Straight Slaves First Sissy Blowjob

XHamster 1 month ago

Emmalee Jones Private Show

79% 4K 2:00 / 10:53

Emmalee Jones Private Show

Flirt4Free 10 months ago

From boyfriend to sissy - Caught Wearing My Thong

Premium 4K 13:28

From boyfriend to sissy - Caught Wearing My Thong

Clips4sale 2 days ago

Kate Rhoades Private Show

57% 4K 2:00 / 10:43

Kate Rhoades Private Show

Flirt4Free 11 months ago

Mean Gals JOI

BigTitsLust 2 years ago

BBC Creampie Cuckold Couple Trained for Pleasure

BBC Creampie Cuckold Couple Trained for Pleasure

Jizzberry 5 years ago

Akira Sissifies Jessica (HD WMV)

56% HD 0:26 / 13:00

Akira Sissifies Jessica (HD WMV)

Clips4sale 1 year ago

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

56% 4K 0:22 / 14:14

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

Clips4sale 2 years ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

CBT and Sissy Humiliation with Goddess Tangent and Lady Electra

CBT and Sissy Humiliation with Goddess Tangent and Lady Electra

Clips4sale 2 years ago

Dressing up Sissy

54% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Sissy Whore Instruction (compilation, Pegging, self Sucking, Cum Eating)

Sissy Whore Instruction (compilation, Pegging, self Sucking, Cum Eating)

FreePorn8 5 years ago

Edging and Sounding by Dominafire

62% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

KAMS 1 year ago

Creating A New Feminized Doll (WMV)

71% 0:13 / 59:30

Creating A New Feminized Doll (WMV)

Clips4sale 1 year ago

Randy Moore Fucks Lance Hart in the Ass with Strapon

Randy Moore Fucks Lance Hart in the Ass with Strapon

Fetishpapa 1 month ago

Maya’s Back for Your Ass

63% VR 0:08 / 3:00

Maya’s Back for Your Ass

FapHouse 11 months ago

Delivery Guy Becomes a Sissy

56% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 8 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 10 months 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

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 5 years ago

Take It Like a Slutty Whore! - Femdom POV with Strap-on, Slut Training, Masturbation with Miss Adrastea

53% HD 0:39 / 15:49

Take It Like a Slutty Whore! - Femdom POV with Strap-on, Slut Training, Masturbation with Miss Adrastea

FapHouse 1 month ago

Shiny Sissy Caught Slacking and Strapped on the Swing

HD 0:10 / 16:42

Shiny Sissy Caught Slacking and Strapped on the Swing

LoyalFans 5 months ago

What Happens when you lose at Boxing

What Happens when you lose at Boxing

Clips4sale 7 months ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 8 months ago

Bella Brookz Private Show

60% HD 2:00 / 16:09

Bella Brookz Private Show

Flirt4Free 3 years ago

The Lust of Sissy 3D Saga - Supportive Sugardaddy

49% HD 0:39 / 12:03

The Lust of Sissy 3D Saga - Supportive Sugardaddy

FapHouse 1 year ago

Greisy & Rey Private Show

57% HD 2:00 / 35:48

Greisy & Rey Private Show

Flirt4Free 6 years ago

Turning Pupcup Into Our Perfect Sissy Slut

51% HD 0:29 / 23:59

Turning Pupcup Into Our Perfect Sissy Slut

IWantClips 11 months ago

Sissy Bitch Pegging Compilation. Femdom Chastity

Sissy Bitch Pegging Compilation. Femdom Chastity

BigTitsLust 2 years ago

Peg Curious - Sharing My Man W Roommate

71% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 months ago

(4K) Sissy Club Slut: Huge Strap-on and Deep Fisting Full Length 50 Minutes (4K)

65% 4K 0:30 / 53:35

(4K) Sissy Club Slut: Huge Strap-on and Deep Fisting Full Length 50 Minutes (4K)

Clips4sale 2 years ago

Sissy training

Dafreeporn 4 years ago

Bella Brookz Private Show

49% HD 2:00 / 5:11

Bella Brookz Private Show

Flirt4Free 2 years ago

Prissy sissy dolly - Maid to be used

62% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years ago

The sissy learns to suck sbites - English audio JOI Sissy

The sissy learns to suck sbites - English audio JOI Sissy

XHamster 2 months ago

Locktober Begins

65% HD 1:01 / 6:35

Locktober Begins

FapHouse 1 week ago

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

45% HD 1:01 / 18:20

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

FapHouse 6 months ago

Tight Sissy Pegged While Gagged in Cuffs - 4k

70% 4K 0:24 / 16:11

Tight Sissy Pegged While Gagged in Cuffs - 4k

Clips4sale 3 years ago

Peg Curious - Sharing My Man W Roommate

58% 1:01 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 months ago

Bisexual husband gets fucked by three strapons

Bisexual husband gets fucked by three strapons

XHamster 2 years ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 3 years ago

Making You Soft Forever

63% HD 0:28 / 19:00

Making You Soft Forever

IWantClips 1 year ago

Eat From a Bowl, Lick My Boots, Suck Rod

Eat From a Bowl, Lick My Boots, Suck Rod

SortPorn 2 months ago

YOU ARE FUCKED BY A REAL ALPHA

YOU ARE FUCKED BY A REAL ALPHA

XHamster 3 months ago

Jen Holly Private Show

54% HD 2:00 / 8:35

Jen Holly Private Show

Flirt4Free 1 year 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

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

Diapers and a Babysitter for the Bed Wetter

51% HD 0:30 / 17:41

Diapers and a Babysitter for the Bed Wetter

Clips4sale 1 year ago

Male to Feminized Sissy Bondage Transformation

59% 0:12 / 12:32

Male to Feminized Sissy Bondage Transformation

Clips4sale 2 years ago

Mistress Luna and sissy Faith erotic strapon fucking in pantyhose

62% HD 0:30 / 23:13

Mistress Luna and sissy Faith erotic strapon fucking in pantyhose

Clips4sale 2 years ago

Cum Like A Girl

51% HD 0:21 / 14:07

Cum Like A Girl

IWantClips 3 years 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 10 months ago

Hotel Dick Sucking for Sissy Training

66% HD 0:15 / 15:02

Hotel Dick Sucking for Sissy Training

IWantClips 8 years ago

hottie blonde trains smooth boyfriend in hotel room

hottie blonde trains smooth boyfriend in hotel room

XHamster 3 years ago

Turned into a Prissy Sissy Dolly Bird! (1080p)

60% HD 0:30 / 9:44

Turned into a Prissy Sissy Dolly Bird! (1080p)

Clips4sale 2 years ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

Lesbian8 1 year ago

Dahlia VR trains princess Zoey

56% HD 0:10 / 14:28

Dahlia VR trains princess Zoey

LoyalFans 9 months ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

Ciara Bunny Private Show

Ciara Bunny Private Show

Camster 1 week ago

HD Sissy Step-sister Panty Perv

HD Sissy Step-sister Panty Perv

XHamster 4 months ago

unmerciful mom catheter incontinence defiance sissy part1

unmerciful mom catheter incontinence defiance sissy part1

SortPorn 3 years ago

Sissygasms Destroy Your Boy Brain – We Own Your Leaking Clit

Premium HD 13:27

Sissygasms Destroy Your Boy Brain – We Own Your Leaking Clit

Clips4sale 3 months ago

Making You My Sissy Fem Boi! (1080p)

56% HD 0:11 / 11:19

Making You My Sissy Fem Boi! (1080p)

Clips4sale 2 years ago

Berlin femdom mommy chokes роре уоur throat raw

Berlin femdom mommy chokes роре уоur throat raw

AveXXX 3 months 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 8 months ago

Slutty Sissy Hitachi Cam Girl Training

HD 0:15 / 12:52

Slutty Sissy Hitachi Cam Girl Training

IWantClips 7 years ago

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

BigTitsLust 1 year ago

Sissy Training

HD 0:39 / 11:01

FapHouse 1 year ago

The Ultimate Sissy Training by MissBratDom

The Ultimate Sissy Training by MissBratDom

Lesbian8 1 month ago

Obedient White Whore Worships BBC & Dicked down Hard

Obedient White Whore Worships BBC & Dicked down Hard

FreePorn8 5 years ago

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

PornFreeNow 3 months ago

Be My Fucking Slut

Be My Fucking Slut

XHamster 6 months 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 2 months ago

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

64% HD 0:10 / 9:57

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

LoyalFans 1 year ago

ANAL training for my DIAPER slave

ANAL training for my DIAPER slave

XHamster 2 years ago

Sissy training with Femdom Headmistress Tangent

Sissy training with Femdom Headmistress Tangent

BigTitsLust 1 month ago

Bimbo rubber doll - Chastity and dick sucking

65% 0:30 / 9:47

Bimbo rubber doll - Chastity and dick sucking

Clips4sale 2 years ago

Brunette and Chastity slave having some fun

Brunette and Chastity slave having some fun

XHamster 1 year ago

Goddess Small Penis Sissy Humiliation

Goddess Small Penis Sissy Humiliation

Clips4sale 1 year ago

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Lesbian8 8 months ago

Sissy choked pink cum drenched by femdom goddess

Sissy choked pink cum drenched by femdom goddess

AveXXX 1 month ago

Helloween Night

Helloween Night

XHamster 4 months ago

Sissified by Step-Mommy

65% HD 0:15 / 13:28

Sissified by Step-Mommy

IWantClips 3 months ago

[EN] - PEGGING - Freak's Mischievous Paradise - (Preview)

[EN] - PEGGING - Freak's Mischievous Paradise - (Preview)

HentaiGem 1 year ago

Dominatrix Mistress April - Herr Specht

Dominatrix Mistress April - Herr Specht

XHamster 3 months ago

Jasmine Flowers Pegging Training, femdom Goddess

68% 1:01 / 17:29

Jasmine Flowers Pegging Training, femdom Goddess

FapHouse 3 months ago

Gender Transformation Wish Granted Turned into a Woman- MtF - Magic - Fairy - Wish - Male to Female - Tied Up - Gender Bender

63% HD 0:25 / 23:53

Gender Transformation Wish Granted Turned into a Woman- MtF - Magic - Fairy - Wish - Male to Female - Tied Up - Gender Bender

Clips4sale 3 months ago

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