Sissy Training Archives | Page 4 of 13

Natashas Bedroom – Sissy All Day

2025-04-03 / Bi encouragement / after, Ass, assignments, Bi, bitch, clips, comple, ember, every, Femdom, Femdom Pov, feminization, first, going, i’m, masturbation, Mesmerize, morni, morning, naughty, night, rough, rules, series, Sissy, Sissy Training, summer, Sure, tasks, things, through, today, train, training, trans, video, videos, watch, while

Natashas Bedroom – Sissy All Day Life is full of […]

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Princess Ashley – Bachelorette Party Sissy Humiliation

2025-04-01 / Bi encouragement / Bi, bikini, bitch, clips, crazy, doesn’t, domina, domination, don’t, dream, ember, extra, fantasy, female, Femdom, Femdom Pov, feminization, Fetish, first, girls, goddess, going, heels, humiliating, Humiliation, little, looking, Mesmerize, night, party, pretty, prince, princess, ready, right, Sissification, Sissy, Sissy Training, today, train, training, verbal, video, videos, watch, while, whore, Worship

Princess Ashley – Bachelorette Party Sissy Humiliation Bachelorette Party Sissy

Princess Ashley – Bachelorette Party Sissy Humiliation Watch Now 🤤

Queen Morningstar – Cocknosis MindTease and Worship – Brainwash

2025-03-31 / Bi encouragement / agree, already, beautiful, Bi, boobs, brain, brainwash, caught, clips, Cocktease, denial, desire, doesn’t, domina, domination, don’t, dress, ember, erotic, fantasy, female, Femdom, Femdom Pov, feminization, Fetish, first, fishnet, going, Hypno, Hypnosis, Hypnotic, Mesmerize, Mind Fuck, morni, morning, mouth, never, queen, ready, Sissification, Sissy, Sissy Training, small, Spitting, strap, strap-on, tease, Teasing, things, train, training, video, videos, watch, Worship, worshipping

Queen Morningstar – Cocknosis MindTease and Worship – Brainwash It

Queen Morningstar – Cocknosis MindTease and Worship – Brainwash Watch Now 🤤

Empress Jennifer – Not a Man – SPH

2025-03-27 / Bi encouragement / Bi, clips, domina, domination, ember, empress, female, Femdom, Femdom Pov, feminization, first, girls, humiliating, Humiliation, i’m, jennifer, Mesmerize, penis, really, saying, since, Sissification, Sissy, Sissy Training, small, Sph, train, training, verbal, video, videos, watch

Empress Jennifer – Not a Man – SPH Men like

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Sissy Training – €at Yur 0wn Cm

2025-03-20 / Bi encouragement / €at, Sissy, Sissy Training, train, training

Sissy Training – €at Yur 0wn Cm Watch Now 🤤

Sissy Training – Eat Your Own Cum

2025-03-20 / Bi encouragement / Bi, clips, ember, Femdom, Femdom Pov, first, Mesmerize, Sissy, Sissy Training, train, training, video, videos, watch

Sissy Training – Eat Your Own Cum mp4 | 1280*720

Sissy Training – Eat Your Own Cum Watch Now 🤤

ScarlettBelle – Sissy Acceptance Counseling

2025-03-17 / Bi encouragement / about, acceptance, Ass, belle, Bi, boobs, boots, Cei, clips, counseling, custom, daily, ember, encouragement, every, fantasy, Femdom, Femdom Pov, first, goddess, going, humiliating, Humiliation, i’m, level, Mesmerize, please, right, roleplay, round, rules, scarlet, scarlett, scarlettbelle, session, Sissification, Sissy, Sissy Training, Sure, therapist, today, train, training, verbal, video, videos, watch

ScarlettBelle – Sissy Acceptance Counseling You’ve been seeing me for

ScarlettBelle – Sissy Acceptance Counseling Watch Now 🤤

Candy Glitter – SISSY MLKED – Sissy Training

2025-03-11 / Bi encouragement / candy, glitter, Sissy, Sissy Training, train, training

Candy Glitter – SISSY MLKED – Sissy Training Watch Now 🤤

Candy Glitter – SISSY MILKED – Sissy Training Fetish – Princess Candy Glitter Dominatrix

2025-03-10 / Bi encouragement / about, Bi, candy, clips, domina, dominatrix, domme, ember, Femdom, Femdom Pov, Fetish, first, glitter, Joi, Mesmerize, prince, princess, Sissy, Sissy Training, slave, sluts, train, training, video, videos, watch, where

Candy Glitter – SISSY MILKED – Sissy Training Fetish –

Candy Glitter – SISSY MILKED – Sissy Training Fetish – Princess Candy Glitter Dominatrix Watch Now 🤤

Urlilgoddess – Worship This Goddess Bulge

2025-03-10 / Bi encouragement / Ass, basement, betas, Bi, clips, desire, domina, drone, ember, every, Femdom, Femdom Pov, first, fucking, goddess, Joi, journey, Mesmerize, Mind Fuck, prepare, prepared, Sissy, Sissy Training, surrender, Teasing, train, training, trans, video, videos, watch, Worship

Urlilgoddess – Worship This Goddess Bulge Attention all sissies, bi-curious

Urlilgoddess – Worship This Goddess Bulge Watch Now 🤤

HumiliationPOV – Feminizing Your Brain, Your Brain Is Throbbing Between Your Legs – Mesmerize

2025-03-10 / Bi encouragement / about, always, Bi, brain, brainwash, bubble, clips, cumdump., domina, domination, eating, ember, encouragement, feeling, feels, female, Femdom, Femdom Pov, first, Forced Bi, forever, fucked, girls, horny, Humiliation, Hypno, Hypnosis, Hypnotic, inside, little, lowly, Make Me Bi, makes, Mesmerize, mouth, never, please, pleasure, relaxing, resist, round, Sissy, Sissy Training, submit, submitting, Sure, these, throat, train, training, trance, trans, trapped, video, videos, voice, wants, watch

HumiliationPOV – Feminizing Your Brain, Your Brain Is Throbbing Between

HumiliationPOV – Feminizing Your Brain, Your Brain Is Throbbing Between Your Legs – Mesmerize Watch Now 🤤

Urlilgoddess Worship This Goddess Bulge .99 (Premium user request)

Urlilgoddess Worship This Goddess Bulge $19.99 (Premium user request)

2025-03-08 / Femdom-videos / Ass, basement, betas, Bi, desire, domina, drone, every, first, fucking, goddess, Joi, journey, Mesmerize, Mind Fuck, prepare, prepared, Sissy, Sissy Training, surrender, Teasing, train, training, trans, video, videos, watch, Worship

Urlilgoddess Worship This Goddess Bulge $19.99 (Premium user request) Name:

Urlilgoddess Worship This Goddess Bulge $19.99 (Premium user request) Watch Now 🤤

Pro Sissy Training & Feminization 4

2025-03-07 / Bi encouragement / Bi, clips, ember, Femdom, Femdom Pov, feminization, first, Mesmerize, Sissy, Sissy Training, train, training, video, videos, watch

Pro Sissy Training & Feminization 4 mp4 | 854*480 |

Pro Sissy Training & Feminization 4 Watch Now 🤤

Sissy Training – Permanent Limp Sissy Clitty Trainer

2025-03-04 / Bi encouragement / Bi, clips, ember, Femdom, Femdom Pov, first, Mesmerize, Sissy, Sissy Training, train, training, video, videos, watch

Sissy Training – Permanent Limp Sissy Clitty Trainer mp4 |

Sissy Training – Permanent Limp Sissy Clitty Trainer Watch Now 🤤

Mistress Paulina – Make Up Lesson Turned Into BBC Training Good Morning Sissy

2025-03-03 / Bi encouragement / after, another, balls, BBC, Bi, bitch, black, clips, dildo, domina, dress, ember, female, Femdom, Femdom Pov, first, fucking, gagging, going, happy, heels, High Heels, Humiliation, hungry, inside, lesson, lipstick, Mesmerize, mistress, morni, morning, night, order, other, pussy, resist, Sissy, Sissy Training, smell, stress, those, throat, today, train, training, turned, tutorial, video, videos, watch, where, whore, Worship, would

Mistress Paulina – Make Up Lesson Turned Into BBC Training

Mistress Paulina – Make Up Lesson Turned Into BBC Training Good Morning Sissy Watch Now 🤤

Fsu – Empty Headed Sissy Training

2025-03-02 / Bi encouragement / Bi, clips, ember, Femdom, Femdom Pov, first, Mesmerize, Sissy, Sissy Training, train, training, video, videos, watch

Fsu – Empty Headed Sissy Training mp4 | 1920*1080 |

Fsu – Empty Headed Sissy Training Watch Now 🤤

Opulentfetish – The Sissy Assignment

2025-02-17 / Bi encouragement / Ass, Bi, chase, clips, comple, control, countdown, ember, enjoy, Femdom, Femdom Pov, Fetish, first, follow, gives, goddess, Instruction, Instructions, Joi, level, makes, masturbation, Mesmerize, order, orders, perfect, person, practice, public, Sissy, Sissy Training, submission, train, training, under, video, videos, watch

Opulentfetish – The Sissy Assignment The sissy Assignment This clip

Opulentfetish – The Sissy Assignment Watch Now 🤤

POV Humiliation – Lena Nicole – Sissy-Loser Mind Warp

2025-02-14 / Bi encouragement / after, below, Bi, clips, ember, Femdom, Femdom Pov, first, Humiliation, loser, losers, Mesmerize, round, Sissy, Sissy Training, train, training, version, video, videos, watch, without

POV Humiliation – Lena Nicole – Sissy-Loser Mind Warp Untitled

POV Humiliation – Lena Nicole – Sissy-Loser Mind Warp Watch Now 🤤

Vera Hostera – Sissy Training

2025-02-10 / Bi encouragement / Sissy, Sissy Training, train, training

Vera Hostera – Sissy Training Watch Now 🤤

Goddess Evelyn – Sissy Cam Audition 3 – CEI

2025-01-31 / Bi encouragement / after, Bi, Cei, chase, clips, Coerced, Cum Eating, dildo, disgusting, domina, domination, don’t, dress, eating, ember, encouragement, evelyn, female, Femdom, Femdom Pov, feminization, first, follow, fresh, fucking, goddess, humiliating, Humiliation, hungry, Instruction, Instructions, little, loads, Mesmerize, mouth, order, orgasm, penis, practice, ready, session, Sissification, Sissy, Sissy Training, small, Sph, third, those, train, training, video, videos, watch

Goddess Evelyn – Sissy Cam Audition 3 – CEI This

Goddess Evelyn – Sissy Cam Audition 3 – CEI Watch Now 🤤

Goddess Evelyn – Sissy Cam Audition – CEI

2025-01-31 / Bi encouragement / agree, before, Bi, Cei, clips, Coerced, countdown, Cum Countdown, Cum Eating, custom, domina, domination, don’t, dress, eating, ember, encouragement, evelyn, female, Femdom, Femdom Pov, feminization, financial, first, follow, goddess, humiliating, important, Instruction, Instructions, interview, light, loser, Mesmerize, other, position, really, rough, Sissification, Sissy, Sissy Training, sluts, super, Sure, tease, thank, through, train, training, video, videos, watch, whore, would

Goddess Evelyn – Sissy Cam Audition – CEI We work

Goddess Evelyn – Sissy Cam Audition – CEI Watch Now 🤤

Goddess Evelyn – Sissy Training Session

2025-01-31 / Bi encouragement / after, allowed, always, Ass, Bi, Chastity, clips, countdown, Cum Countdown, custom, dildo, don’t, ember, evelyn, Femdom, Femdom Pov, first, floor, follow, fresh, fucking, goddess, holes, loads, Mesmerize, minutes, mouth, never, orgasm, panties, remember, remove, service, session, should, Sissy, Sissy Training, spitty, train, training, video, videos, watch, while

Goddess Evelyn – Sissy Training Session (Custom video. No name

Goddess Evelyn – Sissy Training Session Watch Now 🤤

Mistress LucyXX – Gentlemans Mayo

2025-01-28 / Bi encouragement / about, Bi, Cei, clips, doing, don’t, dress, ember, english, enjoy, feels, Femdom, Femdom Pov, Fetish, first, going, happy, humiliate, humiliated, humiliating, Humiliation, leather, little, makes, Mesmerize, mistress, moist, please, pleasure, ready, really, since, Sissy, Sissy Training, something, stress, Sure, things, today, together., train, training, video, videos, watch, would

Mistress LucyXX – Gentlemans Mayo It feels like ages since

Mistress LucyXX – Gentlemans Mayo Watch Now 🤤

Sissy Training

2025-01-25 / Bi encouragement / Sissy, Sissy Training, train, training

Sissy Training Watch Now 🤤