Ruby’s New Life Part 1

I arrived at my Grandpa’s house in the morning on a Saturday. I had been sent here because the finishing school I was to attend was nearby. It was a small community in the middle of nowhere, ‘Lifestyle’ my family called it. Not on any maps for a reason.

My name is Ruby. I’m 18 and pretty average. I’m 5’ 6” and 125 lbs and athletic. Brown hair and brown eyes aren’t what I would call exciting, but the boys seem to like me.

I had a normal childhood, raised by my father and my older brothers. My mother was long gone and no one knew where. When I turned 18 things changed. My older brother was attending the nearby college and he and I started fooling around after school. He taught me how to enjoy my body and how to please him and one cool fall afternoon, he took my virginity.

After my high school graduation, I was informed that I would be going to a finishing school to learn to be an obedient, loving wife. No college for me. He explained ‘the lifestyle’ to me and how my mother left when she couldn’t bear the thought of her children being in the lifestyle and my father had refused to budge.

I was given my mother’s contact information and told that when I finished my first year of school, to write to her and let her know what my decision was. I could decide to walk away from the lifestyle and go live with her, begin a conventional life, or I could choose the lifestyle and continue with school and eventually marry. There was much to consider.

As I walked up the steps, Grandpa carried my luggage behind me. The house was quiet and neat.

“Your room is upstairs.” Grandpa gestured toward the stairs and I walked up.

My room was stark. There was a bed with a black nightstand and a trunk at the end facing toward the bed, no comforter with black satin sheets and a pillow. The dresser was painted black on the wall at the food of the bed with a flat screen TV and DVD player. The closet was small with black shoe racks in the bottom.

Grandpa started opening my luggage and going through my things, sorting them into piles. “Most of this you won’t need, other items can be modified to be acceptable.”

“Modified?”

Grandpa smiled, “You’re going to learn to be pleasing to men, Ruby. What you wear needs to entice and keep our attention.”

“Oh.” I had no idea what he meant.

When he was finished sorting, he put some things, including my bras and panties, into a trash bag and folded the rest neatly into one suitcase. “Let’s get to the tailor before they close. It’s the weekend.”

Grandpa threw the trash bag into the large garbage bin outside and we went into town.

Town was one street with very few shops. There was a grocery store, a medical clinic, I saw a sign for a dentist and several clothing shops, bars and adult stores.

Grandpa made me dizzy giving the Tailor instructions. My jeans were to be modified to be crotch-less, my skirts and shorts shortened, my shirts and sweaters cropped. The Taylor measured me and ordered my school 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 big.” I pulled at my feet, but they didn’t move.

“You’ll get used to it.” He left the dildo inside me to stretch my insides as he went to the television. “This is the first on your school list. When it’s over, I’ll be back to let you relax.” He put in a DVD and pressed play, then pressed a button on the machine and it started slowly moving in and out of me.

I closed my eyes and moaned as the thickness penetrated me over and over.

“It’s on a progressive setting, it will speed up over the next two hours.” He shut the door and left me there.