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5 years ago

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Crossdressing Sissy Trainer Humiliation

11 years ago

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Clipping her Sissy Clit to get her Reward

1 year ago

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2 years ago

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1 year ago

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10 years ago

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Sexy Mistress gives Sissy Boy a Lesson on what happens when he's Bad (Part 1)

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7 months ago

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4 years ago

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SISSY TRAP - YOUNG SISSY RIDING DILDO

3 years ago

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2 years ago

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1 year ago

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ROXIE RAE'S SEDUCTIVE SISSY TRAINING HUMILIATION : 2

2 years ago

Sissy Chastity (part 1)

Sissy Chastity (part 1)

3 years ago

Sissy Transformation Session by your Princess Lynette Phoenix

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5 months ago

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7 months ago

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3 years ago

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3 years ago

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10 months ago

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3 months ago

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3 years ago

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Diary of a Sissy Maid

3 years ago

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Gambling: A Sissy Caption Story - SissyAmberAshley

5 years ago

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2 years ago

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6 months ago

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Sissy Maid Tasks JOI Humiliation

4 years ago

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3 years ago

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6 years ago

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9 years ago

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3 years ago

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Inversao De Papeis Na Minha Sissy

3 years ago

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Sissy Exposed & Humiliated

4 years ago

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2 years ago

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3 years ago

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Sissy Crossdresser Annon Blowjob Training

5 years ago

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1 year ago

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2 years ago

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3 years ago

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Goth Dominatrix Dressing up crossdresser TV sissy slave pt2

3 years ago

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Pretty Princess Sissy Feminization Captions

2 years ago

Sissy Brainwashing (Gooning Captions)

Sissy Brainwashing (Gooning Captions)

3 years ago

Sissy Doggy Worships her Teen Mistress's Feet before Hot Pegging

Sissy Doggy Worships her Teen Mistress's Feet before Hot Pegging

2 years ago

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10 years ago

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4 years ago

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2 years ago

Penny Barber Catches you in Diaper Sissy Bondage

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3 years ago

Sissy Cuckold Husband Life Stages Chapter 1 Part 6

Sissy Cuckold Husband Life Stages Chapter 1 Part 6

1 year ago

Sissy Nikki Graziano Humiliated in Chastity Riding Dildo in Chastity by Femdom Delilah FULL VIDEO

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2 years ago

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4 Liter Painful Enema Submission in Chastity Sissy

3 years ago

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9 years ago

Lingerie, Make-Over, and Buttplug for my Good Sissy Bitch - Mistress Trains you to be a Sissy

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1 year ago

Sissy Jackie getting Pegged again at (Edgewood Erotica on OF)

Sissy Jackie getting Pegged again at (Edgewood Erotica on OF)

1 year ago

Sissy Cuckold with Small Penis Fucked by Dirty Talking Mistress PART 2

Sissy Cuckold with Small Penis Fucked by Dirty Talking Mistress PART 2

3 years ago

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Femdom Pegging her Sissy Cuckold Husband

1 year ago

Man to Sissy Transformation

Man to Sissy Transformation

1 year ago

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2 years ago

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10 years ago

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10 years ago

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3 years ago

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9 years ago

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Sissy Bella Gagged and Cumming from CBT

3 years ago

Welcome to Slut School Dirty Sissy! Mistress Dresses you in Lingerie & Teaches you to be a Good Slut

Welcome to Slut School Dirty Sissy! Mistress Dresses you in Lingerie & Teaches you to be a Good Slut

1 year ago