Training Riley’s Ass for Daddy’s Use

Daughter Finishing School 4

Sophia Sands

Training Riley’s Ass for Daddy’s Use

Daughter Finishing School 4

Copyright © 2026 Sophia Sands

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A New Lesson

The Monday of my third week at the Daughter Finishing School, we had a new lesson instead of Pleasure Mapping. We got to class and sat in our assigned seats. I noticed foam mats next to each chair on the floor. Master Findlay stood at the front with a long, narrow crop in his hands.

“This week, you will be training your assholes to take a cock there. Now that your pussies have been enjoyed by your fathers, and they’ve tried your mouths, you’ll need to prepare your final hole for him to use. Open your desk and take out what you find there.”

My cheeks flushed at the thought of my daddy’s big cock making its way into my butt. I didn’t see how it could possibly fit. The whole idea of anal felt shameful and naughty. Would Daddy really want to enjoy me there? If he did, and I remembered him mentioning it when I last saw him, I’d have to accept it, and get ready for him to use me that way.

I opened the lid, and inside was a cone shaped dildo and a small bottle of lubricant.

“These are butt plugs, and are used to help open you up to penetration in your anus. These are a small ones. You have a few in your rooms as well, bigger than these. Today, I will help you get your first one seated in your anus, but tomorrow I expect you to attend your classes with the next size one already inside you.”

He smacked the crop against his palm, making us jump. “Girls are usually reluctant to do what it takes to insert the plug, so I will be coming around with motivation. Take down your skirts and panties, and stand next to your chair.”

I looked nervously at the crop and undressed, laying my clothes neatly on the back of the chair. I covered the juncture of my thighs with my hands, standing awkwardly by my seat.

“Find a position that works for you to explore your anus with a lubricated finger. You can sit with your legs bent and spread, get down on your hands and knees, or lie on your side. You will massage the ring gently to help you to relax and get used to being touched there.”

I sat down and tried the position with my knees bent up, but that didn’t work well, so I got on my hands and knees and used one hand to rub around my asshole with my finger. I used a lot of lube, and my finger slid around the wrinkly opening. It felt naughty but nice, as I gently slid my finger around and around.

“Now insert your finger and see how deep you ...