Sissy Training Archives

Miss Kelle Martina – Medical Feminization Treatment

2025-09-27 / Bi encouragement / above, Ass, Bi, breast, Cei, class, clips, don’t, ember, Femdom, Femdom Pov, feminization, first, getting, girls, little, Mesmerize, notice, place, please, right, school, Sissy, Sissy Training, taking, train, training, trans, trapped, treatment, treatments, video, videos, watch, woman, women, Young

Miss Kelle Martina – Medical Feminization Treatment Welcome to your […]

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Mistress Alana – Your New Sissy Life – Sissification

2025-09-27 / Bi encouragement / always, Bi, clips, domina, domination, dress, ember, female, Femdom, Femdom Pov, feminization, first, forever, fucked, Mesmerize, mistress, Sissification, Sissy, Sissy Training, sluts, stress, train, training, video, videos, watch, wearing, women

Mistress Alana – Your New Sissy Life – Sissification You

Mistress Alana – Your New Sissy Life – Sissification Watch Now 🤤

Sissy Needs – Proper Sissy Training – 102 – Reloaded (Patreon) mp3

2025-09-26 / Bi encouragement / first, Sissy, Sissy Training, train, training, video, videos

Sissy Needs – Proper Sissy Training – 102 – Reloaded

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ScarlettBelle – Dirty Sissy Freak

2025-09-24 / Bi encouragement / alpha, Ass, balls, belle, Bi, clips, comple, dirty, domina, domination, don’t, dress, ember, encouragement, Femdom, Femdom Pov, Fetish, first, freak, goddess, going, heels, Humiliation, i’m, little, loads, Mesmerize, panty, pantyhose, pervert, ready, scarlet, scarlett, scarlettbelle, secret, Sissification, Sissy, Sissy Training, sluts, Sure, their, train, training, verbal, video, videos, watch, whore

ScarlettBelle – Dirty Sissy Freak There’s a reason that you

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ScarlettBelle – Leaky Little Sissy

2025-09-20 / Bi encouragement / belle, Bi, clips, comple, dirty, domina, domination, dress, ember, encouragement, feeling, Femdom, Femdom Pov, feminization, Fetish, first, follow, horny, Instruction, Instructions, level, little, masturbate, masturbation, Mesmerize, naughty, panties, panty, right, rough, scarlet, scarlett, scarlettbelle, Sissification, Sissy, Sissy Training, sissygasm, sluts, tease, things, through, tight, today, train, training, until, video, videos, watch, while

ScarlettBelle – Leaky Little Sissy Is my naughty sissy feeling

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Mistress Petra Hunter – My Cuckold Boyfriend

2025-09-19 / Bi encouragement / about, after, Anal Training, another, Ass, Bi, boyfriend, Chastity, clips, control, Cuckold, Cuckolding, ember, Femdom, Femdom Pov, feminization, Fetish, first, friend, fucked, getting, having, heels, High Heels, i’m, i’ve, loves, makes, Mesmerize, mistress, never, other, panties, panty, pantyhose, Pegging, petra, place, ready, should, Sissy, Sissy Training, stare, started, stress, taking, train, training, video, videos, watch, while, would

Mistress Petra Hunter – My Cuckold Boyfriend Available in WMV

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Bad Bella – Sissy Training Extreme Stretching

2025-09-18 / Bi encouragement / bella, extreme, first, Sissy, Sissy Training, stretching, train, training, video, videos, watch

Bad Bella – Sissy Training Extreme Stretching Name: Bad Bella

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Mistress An Li – Sl33pover Sissy Cuck- Part III

2025-09-12 / Bi encouragement / about, after, already, always, Bi, clips, dicks, don’t, dress, ember, encouragement, extra, Femdom, Femdom Pov, first, friend, friends, girls, having, Make Me Bi, Mesmerize, mistress, practice, prepare, prepared, ready, right, Sissy, Sissy Training, sluts, stress, sucking, those, train, training, video, videos, virgin, watch, would

Mistress An Li – Sl33pover Sissy Cuck- Part III Now

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Mistress An Li – Sl33pover Sissy Cuck- Part II

2025-09-12 / Bi encouragement / about, always, Ass, better, Bi, clips, Cuckold, Cuckolding, danielle, destiny, dicks, dirty, dress, ember, fantasies, Femdom, Femdom Pov, Fetish, first, friend, girls, going, imposed, Make Me Bi, Mesmerize, mistress, naughty, night, problem, secret, Sissification, Sissy, Sissy Training, sluts, something, stress, sucking, talking, things, thinking, those, train, training, trans, video, videos, wants, watch

Mistress An Li – Sl33pover Sissy Cuck- Part II You

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Mistress An Li – Sl33pover Sissy Cuck – Part I

2025-09-12 / Bi encouragement / about, always, Ass, Bi, bitch, clips, Cuckold, Cuckolding, danielle, domina, domination, double, ember, every, experience, female, Femdom, Femdom Pov, first, friend, fucked, girls, i’m, listen, Mesmerize, mistress, never, night, Sissy, Sissy Training, slave, sluts, stress, super, Sure, train, training, video, videos, virgin, watch, while, women, would

Mistress An Li – Sl33pover Sissy Cuck – Part I

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Heather Highborne – Pink Dreams With Effects

2025-09-09 / Bi encouragement / Ass, Bi, boots, clips, dream, dress, ember, Femdom, Femdom Pov, feminization, Fetish, first, fishnet, heather, highborne, Humiliation, Latex, Mesmerize, Sissification, Sissy, Sissy Training, special, train, training, upskirt, video, videos, watch

Heather Highborne – Pink Dreams With Effects If you desperately

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Goddess Gracie Haze – Sissy Training

2025-09-08 / Bi encouragement / Bi, clips, ember, Femdom, Femdom Pov, first, goddess, going, gracie, Instruction, Instructions, listen, Mesmerize, Sissy, Sissy Training, train, training, video, videos, watch

Goddess Gracie Haze – Sissy Training Time to give up

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ScarlettBelle – Sissy Maid Counseling

2025-09-05 / Bi encouragement / about, agree, another, Ass, belle, Bi, boyfriend, break, clips, counseling, custom, dress, ember, encouragement, every, extreme, extremely, fantasy, Femdom, Femdom Pov, first, french, friend, going, heart, humiliating, Humiliation, i’m, i’ve, instead, Mesmerize, other, place, right, scarlet, scarlett, scarlettbelle, Sissification, Sissy, Sissy Training, slave, submit, Sure, their, therapy, today, train, training, video, videos, wants, watch, wearing, without

ScarlettBelle – Sissy Maid Counseling You’ve scheduled a counseling appointment

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MissIvyDoll – Sissy Training

2025-09-03 / Bi encouragement / first, Sissy, Sissy Training, train, training, video, videos, watch

MissIvyDoll – Sissy Training Name: MissIvyDoll – Sissy Training Video:

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Freya Reign – Witch Turns You Into A Sissy Maid To Pay Off Your Debt

2025-09-01 / Bi encouragement / about, Bi, boobs, breast, cleaning, clips, dirty, dress, ember, encouragement, fantasy, Femdom, Femdom Pov, feminization, fingers, first, floor, having, Mesmerize, money, please, punish, reign, Sissification, Sissy, Sissy Training, Teasing, train, training, trans, turned, undress, video, videos, watch, witch

Freya Reign – Witch Turns You Into A Sissy Maid

Freya Reign – Witch Turns You Into A Sissy Maid To Pay Off Your Debt Watch Now 🤤

ScarlettBelle – You’re My Sissy Slave

2025-08-27 / Bi encouragement / belle, Bi, black, Blackmail, bratty, clips, dirty, domina, domination, don’t, dress, ember, encouragement, fantasy, Femdom, Femdom Pov, first, girls, goddess, heels, humiliating, Humiliation, Mesmerize, perfect, ready, scarlet, scarlett, scarlettbelle, secret, Sissification, Sissy, Sissy Training, slave, Slave Training, those, train, training, video, videos, watch, would

ScarlettBelle – You’re My Sissy Slave I know all of

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Vicious Femdom Empire – Sissy Orgasm Trainer – Anny Aurora – Instructions

2025-08-26 / Bi encouragement / about, already, answer, aurora, before, Bi, bitch, clips, command, domina, domination, ember, empire, ending, every, fantasies, female, Femdom, Femdom Pov, first, german, Instruction, Instructions, Joi, little, locke, locked, masturbation, Mesmerize, mistress, orgasm, perfect, ready, right, Sissy, Sissy Training, stress, strict, stroke, sucking, today, train, training, trans, vicious, video, videos, watch, where, Young

Vicious Femdom Empire – Sissy Orgasm Trainer – Anny Aurora

Vicious Femdom Empire – Sissy Orgasm Trainer – Anny Aurora – Instructions Watch Now 🤤

ScarlettBelle – Secret Panty Obsession

2025-08-22 / Bi encouragement / about, alpha, already, Ass, belle, Bi, clips, dirty, don’t, dress, ember, encouragement, Femdom, Femdom Pov, Fetish, first, found, goddess, going, i’m, little, Mesmerize, panties, panty, perfect, pervert, ready, scarlet, scarlett, scarlettbelle, secret, session, Sissification, Sissy, Sissy Training, slave, Slave Training, sniff, thief, thinking, train, training, video, videos, watch, would

ScarlettBelle – Secret Panty Obsession It’s time to have a

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ScarlettBelle – Sissy Slave Contract

2025-08-16 / Bi encouragement / agree, alpha, Ass, belle, Bi, boots, Cei, clips, Cum Eating, don’t, dress, eating, ember, encouragement, every, Femdom, Femdom Pov, first, floor, goddess, going, heels, Instruction, Instructions, Latex, leather, Mesmerize, never, ready, saying, scarlet, scarlett, scarlettbelle, Sissification, Sissy, Sissy Training, slave, Slave Training, slaves, stripper, sucking, their, train, training, video, videos, watch

ScarlettBelle – Sissy Slave Contract So you want to be

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Kendi Olsen – Ive Always Wanted A Sissy Boyfriend – Forced Bi

2025-08-14 / Bi encouragement / after, always, Ass, asshole, Bi, boyfriend, clips, close, Coerced, domina, domination, domme, ember, faggot, female, Femdom, Femdom Pov, feminization, first, Forced Bi, friend, friends, Girlfriend, girls, going, happily, having, Humiliation, imposed, inside, little, Make Me Bi, Mesmerize, pretty, pussy, really, Sissification, Sissy, Sissy Training, things, train, training, verbal, video, videos, watch, while, whore, women, would

Kendi Olsen – Ive Always Wanted A Sissy Boyfriend –

Kendi Olsen – Ive Always Wanted A Sissy Boyfriend – Forced Bi Watch Now 🤤

ScarlettBelle – Stretch Your Sissyhole

2025-08-13 / Bi encouragement / alpha, Anal Training, Ass, belle, Bi, clips, dirty, ember, Femdom, Femdom Pov, feminization, Fetish, first, goddess, going, i’m, important, Instruction, Instructions, little, Mesmerize, naughty, panty, ready, really, rough, scarlet, scarlett, scarlettbelle, Sissification, Sissy, Sissy Training, sluts, through, today, train, training, video, videos, watch, where, while, whore

ScarlettBelle – Stretch Your Sissyhole It’s time to focus on

ScarlettBelle – Stretch Your Sissyhole Watch Now 🤤

Yourhikerbabe – Step-Mommy Humiliates Sissy Boy Infront Of BBC

2025-08-11 / Bi encouragement / about, after, alpha, BBC, Bi, black, clips, daddy, dress, ember, Femdom, Femdom Pov, first, having, humiliate, imposed, little, loves, Make Me Bi, Mesmerize, mommy, Sissy, Sissy Training, step-mommy, sweet, talking, tease, tells, their, train, training, video, videos, watch, while, white, Worship

Yourhikerbabe – Step-Mommy Humiliates Sissy Boy Infront Of BBC Your

Yourhikerbabe – Step-Mommy Humiliates Sissy Boy Infront Of BBC Watch Now 🤤

Findom Katerina – Sissy Training Sucking

2025-08-03 / Bi encouragement / Findom, first, Sissy, Sissy Training, sucking, train, training, video, videos, watch

Findom Katerina – Sissy Training Sucking Name: Findom Katerina –

Findom Katerina – Sissy Training Sucking Watch Now 🤤

ScarlettBelle – Sissy Valentines Day Challenge

2025-08-02 / Bi encouragement / about, belle, Bi, challenge, clips, domina, domination, dress, ember, encouragement, every, Femdom, Femdom Pov, Fetish, first, little, Mesmerize, naughty, panty, perfect, please, ready, scarlet, scarlett, scarlettbelle, Sissification, Sissy, Sissy Training, sluts, train, training, valentine, valentine’s, video, videos, watch

ScarlettBelle – Sissy Valentines Day Challenge Valentine’s Day is the

ScarlettBelle – Sissy Valentines Day Challenge Watch Now 🤤