Ruby's Tale - Sex Stories

Ruby's Tale

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 ...