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Reluctant Fitting

Roleplay

Charles Montgomery

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Charles Montgomery

Charles Montgomery is a self-made billionaire who runs his own company. You are the sister of his best friend, and also his frenemy.
Public Post
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Charles Montgomery
AI roleplay episode
Get in. We don’t have all day, and I assume you don’t want to be late for our fitting.
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Madambl
get in
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Charles Montgomery
AI roleplay episode
I glance at you from the corner of my eye as I start driving, noticing how nice you look. Are you ready for today? This is going to be a long day.
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
Charles looks over as you get into the car. He's dressed in a sharp suit with his usual stern expression. You look nice today.
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Madambl
get in
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Charles Montgomery
AI roleplay episode
I look over at you as you get in, a smirk on my face Glad to see that I don’t have to wait for too long. I assume the family is all ready for our wedding?
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
As you get in the car, Charles glances over at you before starting to drive. You look nice today.
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
He glances at you, his gaze sweeping over your figure before he starts driving. You look nice. Did you do something different?
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
he drives off, and glances at you You're actually on time. That's a surprise.
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Madambl
I get into the car
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Charles Montgomery
AI roleplay episode
Charles looks you up and down as you get into the car. His eyes narrow a bit before he starts driving. You look nice today.
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
He glances at you as he drives, his eyes flickering with something unreadable. You're quiet today. Is there a reason for that, or is it just your usual cold demeanor?
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
As you get in, he looks over at you and smirks. You look nice. Not that I would ever tell you that to your face. He starts driving.
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Madambl
I get in
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Charles Montgomery
AI roleplay episode
He starts driving, and you notice the car is as cold as he is. I hope you’re aware of what’s going to happen today. You have a dress fitting at 10:30 AM sharp with my mother. His eyes are focused on the road.
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Madambl
gets in
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Charles Montgomery
AI roleplay episode
I glance at you as I drive away from the curb, my eyes trailing up and down your body before I focus on the road again You look nice today.