Sissy Training (81,379)

The best and newest sissy training videos

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

56% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 year ago

Sissy Training - Teaching My Friend How to Give a Blowjob

68% HD 1:01 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 1 year ago

I Milked His Cock, He Fucked My Throat - I Swallowed a Lot of Cum - Female POV

I Milked His Cock, He Fucked My Throat - I Swallowed a Lot of Cum - Female POV

xHamster 1 year ago

The whip lesson 1 - Hungry for hurt

50% HD 1:01 / 1:33:47

The whip lesson 1 - Hungry for hurt

FapHouse 2 years ago

Bi Humiliation & Cum Clean up with a Female Audience

47% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 11 months ago

Sissy Slave Contract

HD 0:10 / 12:37

Sissy Slave Contract

LoyalFans 3 years ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

xHamster 4 years ago

Be A Good Slut

LoyalFans 2 years ago

Suck Cock For Me

HD 0:10 / 18:42

Suck Cock For Me

LoyalFans 1 month ago

two Pathetic Sissies Get to Suck and Screw Each Other

two Pathetic Sissies Get to Suck and Screw Each Other

PornFreeNow 2 months ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

Amateur8 1 year ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

xHamster 3 weeks ago

Sissy Valentine's Day

HD 0:10 / 10:16

Sissy Valentine's Day

LoyalFans 1 week ago

Becoming a sissy

Becoming a sissy

Dafreeporn 5 years ago

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

xHamster 1 year ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

47% HD 1:01 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 9 months ago

Her femboy stands and flows like a whore

Her femboy stands and flows like a whore

xHamster 2 years ago

Making StepBro My Step-Sissy: Telling My Friends Pt 3 Feat Aria Nicole 4K

66% 4K 0:10 / 10:11

Making StepBro My Step-Sissy: Telling My Friends Pt 3 Feat Aria Nicole 4K

LoyalFans 2 weeks ago

Sissy Blowjob

xHamster 4 months ago

Femdom: Fisting, Deepthroat, Strap-on, Humiliation. Arya Grander

Femdom: Fisting, Deepthroat, Strap-on, Humiliation. Arya Grander

xHamster 2 months ago

Up Down Stop Squeeze&mdash_Tessa Breaks Your Gooner Brain

Premium HD 19:20

Up Down Stop Squeeze&mdash_Tessa Breaks Your Gooner Brain

xnxxGold 4 months ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 3 weeks ago

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

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

FreePorn8 4 weeks ago

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

Dafreeporn 1 year ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Amateur8 3 months ago

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

xHamster 9 months ago

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

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

PornFreeNow 4 weeks ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

U will eat his cum

U will eat his cum

SortPorn 4 years ago

Transform Your Perspective: Experience the Thrill of Sissy Fantasy with Farrah de Rossi

Transform Your Perspective: Experience the Thrill of Sissy Fantasy with Farrah de Rossi

MoanTube 1 month ago

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

xHamster 3 weeks ago

Fpov - Your Goddess Wife Is My Slut - Slow Motion Thick Cumshot

63% 1:01 / 13:54

Fpov - Your Goddess Wife Is My Slut - Slow Motion Thick Cumshot

FapHouse 1 year ago

Sissy Slut Anal Training

56% HD 0:10 / 22:06

Sissy Slut Anal Training

LoyalFans 3 months ago

Sissy Mind WARP

Sissy Mind WARP

BigTitsLust 1 year ago

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

xHamster 3 years ago

Lord Maria Introduces her Caged Sub to Her Training Tools

Lord Maria Introduces her Caged Sub to Her Training Tools

Amateur8 2 months ago

ADDICTION HYPNOTIQUE DE SOUMISES - HD

ADDICTION HYPNOTIQUE DE SOUMISES - HD

SortPorn 4 years ago

Best pegging compilation with domineering brunette

Best pegging compilation with domineering brunette

XCafe 1 year ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

You Will Be Wearing a Headscarf Today Sissy Kelly

You Will Be Wearing a Headscarf Today Sissy Kelly

xHamster 1 year ago

Emmalee Jones Party on Oct 23, 2025 - Part 3

61% 4K 2:00 / 1:14:50

Emmalee Jones Party on Oct 23, 2025 - Part 3

Flirt4Free 4 months ago

Sissy Training Day

Sissy Training Day

AbBDSM 11 months ago

Sissy Caption Compilation #three

Sissy Caption Compilation #three

BigTitsLust 1 year ago

Red Lips Tease and Pussyplay

59% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 2 years ago

Stuffed Woman. the Hole Overflows as It Is Full to the Top

Stuffed Woman. the Hole Overflows as It Is Full to the Top

FapHouse 3 weeks ago

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

62% HD 1:01 / 5:10

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

FapHouse 7 months ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

xHamster 2 months ago

Sissy Atonement

Sissy Atonement

SortPorn 3 years ago

Sissy Butt Training !! Fisting

Sissy Butt Training !! Fisting

SortPorn 1 month ago

Sissy Training

BDSMX 3 years ago

Bella Brookz Private Show

63% HD 2:00 / 22:41

Bella Brookz Private Show

Flirt4Free 1 year ago

Sissy Atonement

Sissy Atonement

FreePorn8 4 weeks ago

Lexy Skye Party on Feb 16, 2026 - Part 3

HD 2:00 / 39:11

Lexy Skye Party on Feb 16, 2026 - Part 3

Flirt4Free 1 week ago

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

xHamster 2 years ago

Prissy sissy Dolly - Locked in frills

60% HD 0:10 / 13:13

Prissy sissy Dolly - Locked in frills

LoyalFans 7 months ago

My husband's cock is desperate in his chastity cage

My husband's cock is desperate in his chastity cage

xHamster 1 year 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

Emily & Stesha Private Show

53% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 3 weeks ago

Super Hot Stepsister Spend One Night with Her Stepbrother

47% HD 1:01 / 5:41

Super Hot Stepsister Spend One Night with Her Stepbrother

FapHouse 10 months ago

Bullied Beta

55% HD 0:10 / 6:43

LoyalFans 1 year ago

Emmalee Jones Private Show

Emmalee Jones Private Show

Flirt4Free 2 days 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 7 months ago

Genny Rock Private Show

Genny Rock Private Show

Flirt4Free 5 days ago

Ex Boyfriend to Sissy Girlfriend COMPLETE SERIES | Sissy Feminisation Transformation | Sophia Truee

50% HD 0:10 / 27:16

Ex Boyfriend to Sissy Girlfriend COMPLETE SERIES | Sissy Feminisation Transformation | Sophia Truee

LoyalFans 3 months ago

BBC Sissy FPOV Fellatio Mindwash - Femdom - Dominatrix-Bitch Alexa and Father Jay

BBC Sissy FPOV Fellatio Mindwash - Femdom - Dominatrix-Bitch Alexa and Father Jay

SortPorn 3 years ago

Watch Me Become Your Mistress

Watch Me Become Your Mistress

xHamster 2 years ago

Bella Brookz Private Show

57% HD 2:00 / 5:11

Bella Brookz Private Show

Flirt4Free 1 year ago

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

58% HD 0:10 / 16:20

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

LoyalFans 1 year ago

He's been asking for so long.

He's been asking for so long.

GiveMeAPorn 2 years ago

Bella Brookz Private Show

47% HD 2:00 / 14:02

Bella Brookz Private Show

Flirt4Free 2 years ago

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

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

XGroovy 3 years ago

Anal Dominator

63% 0:39 / 5:12

FapHouse 1 week ago

Delivery Guy Becomes a Sissy

52% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 1 month ago

Jerk Of Instructions With Muscle Mommy

Jerk Of Instructions With Muscle Mommy

Katestube 4 years ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

xHamster 3 years ago

Femdom Cottage Bisexual Blowjob with Encouragement From the Ladies in Charge

55% 4K 0:39 / 12:28

Femdom Cottage Bisexual Blowjob with Encouragement From the Ladies in Charge

FapHouse 11 months ago

Sissification training with paddle and fist given by ladyboss domina

Sissification training with paddle and fist given by ladyboss domina

PornGem 4 years ago

You're Nothing. But You're Comfortable Trampling Femdom Teaser

You're Nothing. But You're Comfortable Trampling Femdom Teaser

xHamster 9 months ago

Sissy Slut Training

54% HD 0:10 / 12:16

Sissy Slut Training

LoyalFans 1 year ago

Step-Mommy's Naughty Sissy

HD 0:10 / 11:16

Step-Mommy's Naughty Sissy

LoyalFans 2 years ago

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

62% 0:39 / 25:09

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

FapHouse 4 months ago

I'LL TEACH YOU HOW TO CUM WITH YOUR ASS

I'LL TEACH YOU HOW TO CUM WITH YOUR ASS

Pornzona 2 days ago

Sissy Cuckold Transformation

Sissy Cuckold Transformation

Dafreeporn 5 years ago

unmerciful mom catheter incontinence defiance sissy part1

unmerciful mom catheter incontinence defiance sissy part1

SortPorn 2 years ago

Bella Brookz Private Show

57% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 2 years ago

Amanda Kiss - Sissy Maid Humiliated And Trained For Cock By Goddess Nyx

Amanda Kiss - Sissy Maid Humiliated And Trained For Cock By Goddess Nyx

AbXXX 4 years ago

Sissyfication 3

59% HD 1:01 / 14:32

Sissyfication 3

FapHouse 8 months ago

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Xfeed 5 months ago

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

49% HD 2:00 / 4:52

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

Flirt4Free 1 year ago

Fpov: Blowjob and Deepthroat Training for Sissies

Fpov: Blowjob and Deepthroat Training for Sissies

xHamster 2 months ago

Dahlia VR trains princess Zoey

63% HD 0:10 / 14:28

Dahlia VR trains princess Zoey

LoyalFans 1 month ago

Total Transformation - HD

39% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 7 months ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 6 years ago

Sissy's Daily Service - Brianna Beach - Faphouse Preview

Sissy's Daily Service - Brianna Beach - Faphouse Preview

xHamster 3 years ago

Feminized Fucked Femdommed

51% HD 0:10 / 18:47

Feminized Fucked Femdommed

LoyalFans 7 months ago

Good boys eat cum

Good boys eat cum

xHamster 1 year ago

How to make a cuckold out of a guy? Licking cum off a black dick

How to make a cuckold out of a guy? Licking cum off a black dick

xHamster 5 years ago

Suck His Dick Loser

Suck His Dick Loser

xHamster 7 months ago

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

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

Amateur8 1 year ago

Dildo Dolly 2

64% HD 0:10 / 15:32

LoyalFans 3 years ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

xHamster 2 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 2 months ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

52% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 3 months ago

Electra Joness Private Show

HD 2:00 / 14:41

Electra Joness Private Show

Flirt4Free 1 week ago

Powerful moment from "JOI Echo With My Big Black Dick - Luna Doll"

Powerful moment from "JOI Echo With My Big Black Dick - Luna Doll"

xHamster 4 months ago

Asmr Good Girl

61% HD 1:01 / 5:51

FapHouse 2 weeks ago

Mistress Fatale's sissy training

41% HD 0:10 / 22:42

Mistress Fatale's sissy training

LoyalFans 2 years ago

part 6 : imprisonment training a sissy after 6 months with no news - maitresse julia

57% HD 0:30 / 15:50

part 6 : imprisonment training a sissy after 6 months with no news - maitresse julia

PornBox 1 year ago

Cum in her mouth after rimjob

Cum in her mouth after rimjob

xHamster 4 years ago

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

62% 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 7 months ago

Aching For Penis

Aching For Penis

SortPorn 10 months ago

Sissy Training in the Dungeon

55% HD 0:10 / 13:29

Sissy Training in the Dungeon

LoyalFans 1 year ago

Diaper Bimbo Bitch Trainer - Mistress Ashley Edmonds

62% HD 0:10 / 16:35

Diaper Bimbo Bitch Trainer - Mistress Ashley Edmonds

LoyalFans 4 months ago

Trained Through the Screen: Denied, Rewired, Relocked -- Full Video Available

Trained Through the Screen: Denied, Rewired, Relocked -- Full Video Available

Lesbian8 7 months ago

How To Masturbate Like A Girl

HD 0:10 / 17:39

How To Masturbate Like A Girl

LoyalFans 1 year ago

YOU Will Implore Me To Link YOU To This Movie scene. Big Compilation.

YOU Will Implore Me To Link YOU To This Movie scene. Big Compilation.

Dafreeporn 3 years ago

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

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

Dafreeporn 5 months ago

Bella Brookz Private Show

67% HD 2:00 / 16:39

Bella Brookz Private Show

Flirt4Free 2 years ago

Elite Sissification: Transform into a High-Class Slut under Mistress Bibianne & Mistress Elena

47% HD 0:10 / 11:00

Elite Sissification: Transform into a High-Class Slut under Mistress Bibianne & Mistress Elena

LoyalFans 1 year ago

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