Ivy & Headmistress; Sissification & Humiliation Punishment

26:37

St Mackenzie's

Published: 20.02.2025 More info Hide

You have upset Ivy, she asked you to Headmistress’s satin prom and you said ‘no’! You told her you were too good for her! This has angered Headmistress, she is outraged you would have the audacity to upset and humiliate one of her girls, but now she has you in her office on the afternoon of the satin prom. She tells you how you will beg for Ivy’s forgiveness and she WILL take you to the prom, but only as her sissy princess! Headmistress will now dress you in a pretty satin dress, a long wavy wig, frilly panties, pantyhose, high heels and also wearing a crown. As one of St Hugh’s top and most celebrated students you will be humiliated beyond belief. Of course everyone at St Mackenzie’s will see you and laugh at you at the prom! Once Headmistress has dressed you she sends you away to have your makeup done, and now you have returned to the office. They are both dressed in their satin dresses ready to go and you think this is it, but Headmistress has a further plan for you...

St Mackenzie's videos

44 fanclub vids

7 vids

St Mackenzie's: Lola & Miss Rose; Made to Jerk off & Cum on Their...

Lola & Miss Rose; Made to Jerk off & Cum on Their Assholes

St Mackenzie's: Ivy & Headmistress; Using Their Eyes to Make You Their Stud

4K 12:47Buy this video for

$13

Ivy & Headmistress; Using Their Eyes to Make You Their Stud

St Mackenzie's: Ivy & Miss Nixx; Jerk off & Cum with Them Both

Ivy & Miss Nixx; Jerk off & Cum with Them Both

St Mackenzie's: Morgan & Miss Lee; Cum on Two Huge Pairs of Tits

Morgan & Miss Lee; Cum on Two Huge Pairs of Tits

St Mackenzie's: Essie; Black Sheer Stocking Tease & Pussy Spreading

Essie; Black Sheer Stocking Tease & Pussy Spreading

St Mackenzie's: Miss Marsh. Stroke Your Big Cock & Cum for Teacher

Miss Marsh. Stroke Your Big Cock & Cum for Teacher

More videos like this

Lady Valeska: Sissification

SissificationLady Valeska

Domina Lady Vampira - SM Studio Femdom Empire: Bi Slave Gang Bang 2 - Showing the Sissy Whore

HD 11:17Buy this video for

$15.62

Bi Slave Gang Bang 2 - Showing the Sissy WhoreDomina Lady Vampira - SM Studio Femdom Empire

Lady Valeska: Sissy College Lesson 5 - Sluttification

Sissy College Lesson 5 - SluttificationLady Valeska

DeesseJulia: Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse JuliaDeesseJulia

Margo Apollo Femdom: Performing a My Husband's Transformation Into a Sissy Slut, Part 1

Performing a My Husband's Transformation Into a Sissy Slut, Part 1Margo Apollo Femdom

Sarah Stern: A Riding Lesson with the Crop

A Riding Lesson with the CropSarah Stern

Shannon Huxley: Married Cock Belongs in My Pussy Not Hers

Married Cock Belongs in My Pussy Not HersShannon Huxley

Lady Blackdiamoond: Chaste sissy

Chaste sissyLady Blackdiamoond

Fetish Tv: My lipstick guy

My lipstick guyFetish Tv

Lady Valeska: Sissy Fucks Boots - Goth Domme Fucks Sissy

Sissy Fucks Boots - Goth Domme Fucks SissyLady Valeska

Christina X Productions: Christina rides the sybian - Part 1

05:23Buy this video for

$6.25

Christina rides the sybian - Part 1Christina X Productions

Nadia Foxx: Spending Time Apart Is Hard.. but These Toys Will Make...

Spending Time Apart Is Hard.. but These Toys Will Make Things Easier!Nadia Foxx

Lady Valeska: Sissy compilation volume 2

Sissy compilation volume 2Lady Valeska

Lady Valeska: Turning Their Timid Boy Into a Cute Girl

Turning Their Timid Boy Into a Cute GirlLady Valeska

Fetish Tv: Wearing to cross dress

Wearing to cross dressFetish Tv

Lady Sonia: LADY SONIA - Doing a little job for Sonia and Red

LADY SONIA - Doing a little job for Sonia and RedLady Sonia

Lady Valeska: Sissy College Lesson 1: Dollification

Sissy College Lesson 1: DollificationLady Valeska

Siri Pornstar: Siri Power Grrl's -boobs Jerk-off Instructions

Siri Power Grrl's -boobs Jerk-off InstructionsSiri Pornstar

Morrigan Havoc: Jerk Off to My Sexy Panties

Jerk Off to My Sexy PantiesMorrigan Havoc

Claudia Kink: Wife's Crossdressing Proposal

HD 08:27Buy this video for

$10

Wife's Crossdressing ProposalClaudia Kink

DominaFireOfficial: Sissy Anal Examination by Dominafire

Sissy Anal Examination by DominafireDominaFireOfficial

Vicky Vette: Vicky Vette.. A cop bribed with cum!!

Vicky Vette.. A cop bribed with cum!!Vicky Vette

No limits I love it rough: The pervers travestie.

The pervers travestie.No limits I love it rough

British Domination: Chastity Head Fuck. I Want to Fuck with My Slaves...

Chastity Head Fuck. I Want to Fuck with My Slaves Head.British Domination

Margo Apollo Femdom: Performing My Husband's Transformation Into a Sissy Slut Part 4

Performing My Husband's Transformation Into a Sissy Slut Part 4Margo Apollo Femdom

Fetish Tv: Lets fuck the crossdresser

Lets fuck the crossdresserFetish Tv

Lakeview Entertainment: Way too hot - part 4 of 5

Way too hot - part 4 of 5Lakeview Entertainment

Dominatrix Frida: Sissy training - task 13 - feminization training

Sissy training - task 13 - feminization trainingDominatrix Frida

Sarah Stern: Punished in Her Curlers

4K 26:10Buy this video for

$27

Punished in Her CurlersSarah Stern

ElleEros: Girlfriend Gets Kinky During Lunch - Anal JOI Game with Elle...

Girlfriend Gets Kinky During Lunch - Anal JOI Game with Elle ErosElleEros

Soiyu Hentai: The Goddess Ntr - Hentai 3D Uncensored V249

The Goddess Ntr - Hentai 3D Uncensored V249Soiyu Hentai

Naughty Lesbian Girls: The Vips Get a Special Strip Show Where the Girls...

The Vips Get a Special Strip Show Where the Girls Eat Pussy Live on StageNaughty Lesbian Girls

Absolute BDSM films - The original: The queen of your perversions - scene #05

The queen of your perversions - scene #05Absolute BDSM films - The original

skyunited007: The Camera Under the Table Captured a Beautiful Woman at...

The Camera Under the Table Captured a Beautiful Woman at Home Alone and Watching a Porn Movie.skyunited007

Eros JOI: Trying on panties for my stepbrother-in-law (with Claire Heart)

Trying on panties for my stepbrother-in-law (with Claire Heart)Eros JOI

Nadia Foxx: Humiliation Roleplay (sph, JOI & CEI)

Humiliation Roleplay (sph, JOI & CEI)Nadia Foxx

Get Your Fix: Huge melon tit babe anal blasted

Huge melon tit babe anal blastedGet Your Fix

St Mackenzie's: Miss Page; Masturbating to Orgasm Behind the Medical Screen

Miss Page; Masturbating to Orgasm Behind the Medical ScreenSt Mackenzie's

Soft Vulgar: Testing Out the New Lenses

Testing Out the New LensesSoft Vulgar

Tirrany Girls: Lezdom fun with redhead and her mistress

Lezdom fun with redhead and her mistressTirrany Girls

DeesseJulia: Chastity Release: Your Last Penetration of Your Life

Chastity Release: Your Last Penetration of Your LifeDeesseJulia

Amator Media: Sissy gets what she deserves

Sissy gets what she deservesAmator Media

Domina Lady Vampira - SM Studio Femdom Empire: Sissy maid party

14:03Buy this video for

$15.62

Sissy maid partyDomina Lady Vampira - SM Studio Femdom Empire

Lady Valeska: Cum Like a Sissy (at House of Sinn)

Cum Like a Sissy (at House of Sinn)Lady Valeska

BDSM Deutschland: BDSM Sadomaso Klinik 3 - Movie German

BDSM Sadomaso Klinik 3 - Movie GermanBDSM Deutschland

Domestic femdom: Using you as a spitoon

Using you as a spitoonDomestic femdom

Diana Von Rigg: Sissy Slut Anal Destruction

Sissy Slut Anal DestructionDiana Von Rigg

Dominatrix Frida: SissyPinkyLilly - sissy maid - part 1

SissyPinkyLilly - sissy maid - part 1Dominatrix Frida

PureVicky66: Grandma Will Dominate

Grandma Will DominatePureVicky66

Sophie James: I have never seen a cock before

I have never seen a cock beforeSophie James

Diana Von Rigg: Sissy Bitch Boyfriend

Sissy Bitch BoyfriendDiana Von Rigg

Nylon fetish 4u: 599. Spandex Nylon Encasement JOI, Big Nylon Ass JOI, Spandex...

HD 10:08Buy this video for

$15.62

599. Spandex Nylon Encasement JOI, Big Nylon Ass JOI, Spandex Ass JOI, Cum Demands, Cum Encouragement, Big Butt in Shiny SpandexNylon fetish 4u

Java Consulting: Three nasty ladys and her sissy friend

Three nasty ladys and her sissy friendJava Consulting

Lady Valeska: Latex Ladies Lunch Part 1 - Humiliating the Clumsy Maid

Latex Ladies Lunch Part 1 - Humiliating the Clumsy MaidLady Valeska

Lady Valeska: Slut competition

Slut competitionLady Valeska

Soiyu Hentai: Threesome with Two Beauty Lady - 3D Animation V577

Threesome with Two Beauty Lady - 3D Animation V577Soiyu Hentai

Boys in Stockings: Blonde slave suck and fuck two strap ons

Blonde slave suck and fuck two strap onsBoys in Stockings

Miss Adrastea: Lick my soles

Lick my solesMiss Adrastea

Lady Stardust: Therapist prescribes stroking

HD 08:52Buy this video for

$25

Therapist prescribes strokingLady Stardust

MMV films - The Original: Three Hot MILFs Ass Fucked and Cummed on Pussy and...

Three Hot MILFs Ass Fucked and Cummed on Pussy and Mouth by Three Huge CocksMMV films - The Original

SophiaSmithUK: Black Stockings High Heel JOI

Black Stockings High Heel JOISophiaSmithUK

Naughty Lesbian Girls: Naughty Girls Get Detention for Dressing Like Sluts but Turn...

Naughty Girls Get Detention for Dressing Like Sluts but Turn It Into a Lesbian OrgyNaughty Lesbian Girls

Pussy Tribe: Naughty doctor had a special treatment for her sexy nurse

Naughty doctor had a special treatment for her sexy nursePussy Tribe

Dark Dungeon Secrets: Hottie with a decent rack getting ready for a BDSM...

Hottie with a decent rack getting ready for a BDSM sessionDark Dungeon Secrets

Melon Juggler: SSBBW Dr Vallery Spanks Big Tits BBW Alexxxis Allure

SSBBW Dr Vallery Spanks Big Tits BBW Alexxxis AllureMelon Juggler

KinkyDomina: Sexy brunette MILF gives CEI

Sexy brunette MILF gives CEIKinkyDomina

Shannon Huxley: Teachers Boot Discipline

Teachers Boot DisciplineShannon Huxley

Sarah Stern: Spank Me Please Sarah

4K 14:23Buy this video for

$20

Spank Me Please SarahSarah Stern

Lady Valeska: Latex sissy humiliating self facial

Latex sissy humiliating self facialLady Valeska

SophiaSmithUK: CEI Women Dont Swallow

CEI Women Dont SwallowSophiaSmithUK

Dream Factory: Gorgeous silk lingerie set for my sissy

Gorgeous silk lingerie set for my sissyDream Factory

Ariel Anderssen: BDSM, Shame, Porn & Me

BDSM, Shame, Porn & MeAriel Anderssen

Nylon MILFS: Pussy play on the desk

Pussy play on the deskNylon MILFS

Luna Sapphire: Cum Pie CEI Cum Eating Instruction

Cum Pie CEI Cum Eating InstructionLuna Sapphire

Soiyu Hentai: Hentai 3D Uncensored Compilation C06

Hentai 3D Uncensored Compilation C06Soiyu Hentai

Lexie Cummings: Lexie under orders from Mistress Di

Lexie under orders from Mistress DiLexie Cummings

Sarah Stern: The Leaving of Cherry

4K 53:05Buy this video for

$40

The Leaving of CherrySarah Stern

Aunt Judy's: AuntJudys - 48 y.o British milf Ms. Kitty in fishnet stockings & lingerie

AuntJudys - 48 y.o British milf Ms. Kitty in fishnet stockings & lingerieAunt Judy's

Maitresse Christal: BDSM world by Mistress Christal

BDSM world by Mistress ChristalMaitresse Christal

Eros JOI: I am Kimberly Kane's sissy bitch (featuring Zoey Holloway)

I am Kimberly Kane's sissy bitch (featuring Zoey Holloway)Eros JOI