Ruby's Tale - Sex Stories

Ruby's Tale

... uniform as well.

We stopped by a few adult shops and my school lists were filled, then we stopped for shoes. Grandpa chose what he liked and gave the store clerk my size. I tried them all on and before I knew it, we were on our way home.

When my shoes were put neatly onto the racks in my room, I went downstairs to find Grandpa reading the paper. He looked up and smiled, “All put away neatly?”

“Yes, Sir.” I smiled and sat on the couch opposite him.

He eyed me closely, “You know that things will be different here.”

“Yes, Sir.” Just how different, I didn’t know.

“We don’t have television, so kiss your favorite shows goodbye. We get the paper and we have plenty of movies. While you’re in school, you have a list of movies that you are to watch specifically. I didn’t choose them, so don’t complain to me.”

“No, Sir.”

“Any time spent at home will be in your room or running errands, cooking and cleaning. For the remainder of the summer, your school requires you to sunbathe. So for two hours a day, you’ll have time on the deck out back by the pool. I suppose swimming is okay.”

“Yes, Sir.”

“Your school has also supplied you with an ipod with music loaded onto it if you want to listen to something.” He handed me the black ipod and I scrolled through the songs. I’d never heard of any of them.

“Thank You.”

“I won’t be fucking you like your dad and brothers did, so don’t get that idea into your head. It messes with your training and I have a woman who ...

... services me.”

“Yes, Sir.” No sex all summer?

“There are other kids your age around, I’m sure you’ll bump into them on trips to the grocery store. Visits are acceptable, but you must ask permission before you visit anyone else, is that understood?”

“Yes, Sir.”

“I have a summer activity list from the school, so each day we’ll be sure to check off those too. Today, we’ll start with the machine.” He stood up and headed upstairs, beckoning me to follow him.

When we got to my room, he told me to undress. While I took my clothes off and folded them neatly on the nightstand, he opened the trunk and a machine pulled out on hinges and rested nicely on the edge of the bed. Grandpa pulled out a rather large, thick dildo and slid it onto a shaft on the machine.

Something about being naked with my Grandpa, who refused to use my body made me feel self-conscious.

“Lay down.”

I laid on the bed and Grandpa put a wedge under me to raise my hips to the desired height. He squirted lubricant onto the dildo and positioned it at the entrance to my pussy. Then he reached behind the bed and produced two leather cuffs that he attached to my wrists so that my arms were wide above me. He did the same to my ankles so that they were spread wide.

When the machine came to life, it slowly penetrated me, easing the thick dildo into my tight pussy before Grandpa turned it off. I was filled like I’d never been filled before. I grunted with discomfort.

“Hurt?”

“No, it’s just … so ...