Chapters tagged humiliation

Introduction by lovestoblush

Chapter 1

Matt is lying in bed staring at the ceiling. He is really nervous and wondering if he can go through with this. His phone vibrates from a text message. It reads "I'm out front. Don't make me wait" Matt stands up and looks in the mirror. He is wearing a t-shirt and shorts. He tak...

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Matt is going to do her chores by lovestoblush

Chapter 2

"Excellent. We will be going to my house first. I have some chores for you." She starts driving. "Now normally I would probably have you come out naked, but seeing as its our first 'date' I am going to start out easy. I will only make you strip once we get to my place. Is that fa...

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909 Views

Matt is going to strip in a clothing store changing room and wait... by lovestoblush

Chapter 2

Matt enters the store and looks nervously around. It's a WOMEN'S store! The racks are filled with lacy apparel, brightly-colored dresses... The owner, a shapely blonde middle-aged woman, looks at him knowingly. "Can I help you, sir?" she asks, smiling a secret smile. "Well I-...

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Matt has some impromptu tailoring done. by lovestoblush

Chapter 2

Matt sits in the car with Miss Pippa, nervously wringing his hands as she drives him to some unknown destination. She has kept quiet since their initial greeting but she in no way seems to be in a bad mood. Quite the opposite, Matt realizes, Miss Pippa is so comfortable its as if...

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878 Views