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. Two hours!?

The movie was a porn, a horrible story line to get into the sex. Black men were teasing a petite blonde in a bikini by a pool, pulling at her suit to get a peek, taunting her. She finally gave in and took off her top and lay down in the grass. The men descended on her and started sucking her nipples, her fake tits standing straight up for them, sliding her bottoms off and licking her slit.

The machine pushing into me was starting to feel good as I stretched to accommodate it. Watching the men kiss and suck and rub the woman made me wish I had a free hand to rub my clit. Before long, I felt my own juices dripping down my ass and wanted to beg someone to get me off. I was alone. I grunted and moaned in frustration.

I had never had an orgasm without clitoral stimulation and the two-hours of movies were torture. The men were fucking her three holes, cumming all over her body and face, in her mouth. The machine sped up periodically and was fucking me faster and faster. By the time the last group of men had finished using yet another woman’s holes and covering her in ropes of semen, the machine was jutting in and out of me so fast that I thought I would scream if I didn’t cum. I grunted and whimpered and pulled at the cuffs with frustration.

Grandpa came into the room and turned the TV. He stood there, watching me struggle and groan, covered in sweat, my pussy a sloppy, wet hole being violated at high speed.

“Please!” I screamed.

“Please what?” He smirked.

“I need to cum!”

“Not my job.” He stopped the machine and pushed a button that slowly pulled the dildo out of me. He undid the restraints and I rolled onto my side, panting and trying to slow my breathing.

“I need to cum!”

“Not allowed yet. And if you do make yourself cum, I have a list of punishments I’m to carry out. You don’t want that, I assure you.” He took my clothes and handed me a bag with new clothes in it. “Get dressed, I need you to run into town and get groceries for dinner.” He pulled the dildo off the machine and put it back into the trunk, taking the dildo with him to clean.

He started walking out, “And this door is to remain open unless I shut it. There is no door on the bathroom either. You won’t get much privacy any more I’m afraid.”

I found a towel in the nightstand drawer and wiped the sweat from my body before I cleaned the sloppiness from between my legs. The sheets were soaked with sweat and my juices. I pulled them off the bed, revealing a rubber sheet underneath.

When the bed was re-made and the soiled pile put in the laundry room, I went back to get dressed. I felt like stomping in frustration. I had never been so turned on without release in my life.

The clothes were hardly clothes. The skirt was black and made of a thin, airy fabric. When I put it on, it just covered my pussy in the front and left the bottom curve of my ass cheeks exposed. The shirt was a tiny white tank top that looked like it would fit an 8-year old. I put it on and it stretched around my D cup breasts, hugging them but just covering my nipples, leaving the bottom half bare. I had to go in public like this?

I slipped on black ballet flats and went downstairs. Grandpa looked me up and down approvingly and waved me over. “Just one minute.” He handed me the car key and lifted my tank top. He produced a small suction bulb that he placed over my nipple to suck it into the shaft and rolled a small rubber band down around the base of my nipple. The pressure made my nipple bulge grotesquely and stand out bigger than I’d ever seen it. When the other nipple was done, he pulled the tank top down and admired my obscene nipples through the white fabric.

“Better hurry back, that’s gonna sting soon.” He handed me a list of six items and waved me out the door.

When I opened the car door, I saw that my Grandpa had installed a board in the driver’s seat with a thick, 7” dildo standing proudly on it. I thought about just moving it, but I noticed it was locked in place and I had no key.

The pressure on my nipples was increasing and I felt myself getting wet with anticipation. I lowered myself onto the dildo, letting it fill me and took a deep breath. It felt amazing. I shut the door and headed down the road.

Grandpa’s house was on a country road that wasn’t paved. The bumpy ride jostled the dildo inside of me and the potholes made me bounce, making the sensation even more intense.

By the time I pulled into the grocery store in town, I was panting and moaning in frustration. My nipples were starting to sting, just like Grandpa said they would.

I looked around to see if anyone could see me before I lifted off the dildo and got out. My juices were smeared on my inner thighs and the skirt I was wearing did nothing to hide it. I looked in the car for anything to wipe myself with, but the car was empty. Spotless.

I took a deep, jagged breath as I started walking into the store with my list. My heart was pounding and I started to shake. Would I be arrested for being dressed so inappropriately?

I saw a woman leaving the store with a bag and I panicked but kept walking, the stinging sensation driving me forward. I noticed the woman wearing a white, flowing sundress and wished I was more covered up. Then I looked closer and realized that the material was so sheer that I could see her entire naked body. It was like the dress was made out of a sheer white scarf. She noticed me looking at her and smiled.

The store was fairly busy, mostly women doing shopping with lists like my own. Everyone was dressed in something revealing, showing off their assets in provocative ways that would never be allowed in the conventional world. I blended in, which made my heart rate slow.

The sting in my nipples was becoming more intense and it made it difficult to concentrate on finding things in the unfamiliar aisles. But find them I did. When I went to the front with my basket, I realized that Grandpa hadn’t given me any money to pay with.

I stayed in line, not wanting to lose my place or this would take longer and my nipples were so painful. I watched the woman two places ahead of me as the cashier rang up her purchases and put them in bags. When the checker was finished, she asked the checker, “How will I be paying for this?”

The checker was a guy about my age, good looking and tan with dark eyes and a brilliant smile. “Sixty five ninety-seven ….. today that’s …..” He thumbed through a booklet and ripped a slip from it and handed it to the woman. “Have a nice day!”

“Thank you, Sir.” She looked down at the slip and took her bags out of the store with her.

My curiosity was growing by the second as I watched two more women do the same. What would mine say?

The checker started on my items and I tried to smile politely despite the fire in my breasts. I resisted the urge to put my hands around his throat and tell him to hurry the fuck up. “You new in town?” He smiled and looked at my breasts.

“Yes.” I couldn’t manage much more without moaning in pain.

“Starting school in the fall?” Why the fuck was he taking his time?

“Yes.”

“In a hurry?” He looked down at my breasts.

“Yes.”

He paused with the last item and lifted my shirt to expose my now purple nipples and then covered them back up. “Gorgeous.” He rang up the last item.

“How will I be paying for this?” I asked just as the other women had.

“Thirty-three forty-nine is …….” He tore a slip out of his booklet and handed it to me.

“Thank you.”

“Sir.”

“Excuse me?”

“No matter who you address in this town, be sure to use ‘Sir’. My tip for the day, freebie with no reporting to your family.”

“Oh.” I stammered for a second, “Thank you, SIR.”

“Have a nice day!”

I looked down at the slip, it read:

TAVERN DUTY, TWO HOURS

I had no idea what that meant, but I took my bag of groceries and quickly walked to the car. I would have run, but then my tits would have bounced and the pain would be worse.

The ride home bouncing on the dildo was just as torturous as the ride into town, maybe more so. My nipples were on fire and mixing the pain and the pleasure confused my mind into a dizzying state. I didn’t know whether to concentrate on the pain and driving faster home or to enjoy the dildo and ignore the pain.

In the end, driving faster meant that I bounced harder on the country road and my breasts felt like lead weights.

When I pulled in the driveway, I grabbed the grocery bag, my slip of paper and jumped out to run inside.

Grandpa looked up at my frantic, panting self and smiled, “How was your first shopping trip?”

“Can you please take them off, Grandpa? Please!”

“Put the groceries away in the kitchen and come back. Where is your payment slip?”

I handed him the slip and ran into the kitchen. I didn’t know where anything went! My nipples felt like they would fall off at any moment.

Back in the living room, Grandpa set the slip on his side table and gestured me to move toward him. He lifted my shirt and took the rubber bands off each nipple. The sharp pain of the bands coming off made me jerk, but the warm relief when they were off made me sigh.

“You have Tavern Duty tonight I see.”

“Tonight? What is that?”

“You’ll waitress or wash dishes or bartend I suppose. Whatever they need.”

“Don’t they have employees who do that?”

“This town runs differently than most, my dear. Money is only exchanged when men purchase something. If we have a woman to send on our errands, payment is with …. Favors. Work mostly. Female employees other than shop owners that you see are working to pay off their slips. The male employees are paid with money, of course. Instead of paying you tonight, they’ll send the money you earn directly to the grocery store to pay your bill.”

“Oh.” It seemed sexist to me. Were women nothing but slave labor here? My nipples ached now that the blood was rushing back to them and I reached up to rub them, but they were sore to the touch.

“You’ll get used to it. By the time school starts, they’ll be trained up nicely.”

I had no idea what he meant.

“You’ll need to be ready by 7:00 so I can drive you to work. We’ll have an early dinner in a bit. First, you should exercise. Daily exercise is a requirement. Do you jog?”

“Yes, I played a lot of sports in high school, we did a lot of running.”

“Good. I’ve laid out your jogging clothes on your bed. When you come down, I’ll drive you to the track.”

On the bed was what looked like a normal white sports bra, but low cut with spaghetti straps and no lining. The cotton seemed very thin to me. The shorts were nothing but white mesh, high cut jogging shorts that exposed the bottom curve of my ass. You could see everything through them.

I put on my new running shoes and invisible white socks and bounced downstairs, tying my hair into a ponytail with the white hair band that had been left for me. The bra didn’t give much support.

Grandpa looked me over and stood up with the car key in his hand and headed for the door. I followed and when we got to the car, the board with the dildo was locked in on the passenger side. I pulled my loose shorts to the side and lowered down on it. My cheeks flushed to be like this in front of Grandpa. It would have been less embarrassing if he would at least let me fuck him. But keeping the relationship proper made all of this incredibly embarrassing somehow.

When we arrived at the track, my pussy was once again sloppy wet. Grandpa handed me a wet wipe and I cleaned the dildo before we headed for the track.

The stands at the stadium were riddled with men, some reading, some watching the runners.

“You younger girls usually have an escort to your exercise events. You’re always watched.” He gestured toward the track, “Two miles for today.” He headed for the stands to sit with some men he appeared to be friends with.

I turned to the track and watched the other girls my age, all dressed in the same white uniform, wet and panting. How long were they being made to run? Their hair was drenched; their white uniforms clinging to their bouncing breasts and erect nipples, showing everything through the wet white fabric as they jogged.

I fell in line and started running. The track looked like a ¼ mile, so I set my inner dial to eight laps and focused on my breathing. When I got half way around, I noticed the girls running through a series of what looked like water sprinklers on either side of the track that sprayed them from the neck down. That was why they were wet. When I went through, I noticed the pressure was fairly high and the water was freezing. I squealed as I was drenched with the water and my hair and face were splattered with droplets.

Now my athletic body was glistening with water and my white sports bra was wet and hugging my own hard nipples as my large tits bounced obscenely. My nipples were still sore and being hard and cold made them ache a little. I wondered if all the other girls were experiencing the same sensation.

When I finished my two miles, I exited the track and went to find Grandpa in the stands. He turned to me and smiled, “This is my Granddaughter, Ruby. She’ll be a first year in the fall.” The men eyed me up and down, focusing on my breasts and looking through my mesh shorts. Standing there, fully exposed in front of so many men was embarrassing. I had never been ogled so much in my life and I felt myself blush.

One of the men spoke to my Grandpa, “I haven’t seen pubic hair in quite a while, you gonna wait to have her waxed?”

“I was thinking of waiting, we’ll see.”

Waxed? I wasn’t going to have ANY pubic hair?

“Well, before you have it done, someone should enjoy it, don’t you think?”

Grandpa stood up and gestured to me that we were leaving, “We’ll see, Josh.”

I was shivering by the car when Grandpa unlocked it for me and watched me lower myself onto the dildo before shutting me in. My nipples ached and my skin felt cold, despite the exercise.

“You’re a good runner. Next time we’ll push it to three miles.” Grandpa headed for home, glancing now and then at my grimacing face as I was impaled on the dildo. I can’t be sure, but I think he hit some potholes deliberately on the way back to watch me bounce and to see my face when the dildo slammed into me.

When we got inside, Grandpa gestured toward the kitchen, “Go fix an early dinner now. We eat vegan in this house, if you hadn’t noticed by the items you bought. Healthy bodies are important. You’ll learn.”

I went into the kitchen to start cooking the items I’d bought. Had I really only bought enough for one meal? How many trips to the store would I have to make!?

As if he was reading my my mind, Grandpa answered, “Larger amounts require harder work and in some cases, sexual favors to be paid off.” Grandpa came to sit at the dining table and watch me cook. “I’m keeping the amounts low for you to ease into this. Understand?”

“Thank you, Grandpa.” I was looking for pots and pans and knives and such in the cupboards and felt his eyes on me.

I was shivering from the cold still, though I could feel my body warming up a little. Of course, my inner thighs were wet with my juices. I searched through the drawers and cupboards to find the items I needed. When I had to crouch down, he yelled at me, “Always bend, Ruby, never crouch! You’ll be punished for crouching whether it’s here at home or anywhere in public. They’ll report every infraction to me.”

I straightened my legs and bent over, exposing my ass and my juicy inner thighs to him as I looked for the pan I needed. So women were really objects to these people, weren’t they?

“Looks like you enjoyed your ride.” I noticed him staring at my thighs.

“Kind of, yes.”

“You’ll get used to it.” He was looking through a booklet, “They sure do have a lot of rules at this school.” It must have been my handbook. “No orgasms, nipple training, exercise, anal training. Hmm. I guess we should start on that after dinner. Don’t want you showing up to work and everyone knowing you haven’t started that yet.”

“Anal training? Like, my ass?” I had never even thought of my ass being part of sex.

“Your kit is here. I’ll get you started and we’ll work up to what you have to have for school.”

I cooked dinner and we ate in silence, me squirming on the dildo that was attached to my dining chair. Being filled and wet with my still-damp sports bra teasing my nipples was curbing my appetite.

“Eat. You need nutrition and you need to stay hydrated. 60 oz. Of water each day, understood?”

“Okay, Grandpa.” I guzzled my water and finished my food with little excitement. While I was cleaning the kitchen, Grandpa went upstairs and came down to tell me it was time to get ready for work.

On the bed were my clothes. I was never going to choose my clothes again, was I? There was a pair of black leg-hugging chaps made out of a comfortable stretchy material, but when I put them on, my entire crotch and ass were exposed. The shirt was a white, sheer jersey material, spaghetti straps and a small bit of fabric that tied between my breasts, covering the nipples but little else. I didn’t see the point, you could see right through it.

Black heels and a high, tight ponytail and I was down the stairs.

Grandpa had me bend over in the living room and he spread my ass cheeks to rub a small dab of lubricant just inside of my rear hole. I jerked in surprise at first, but took a deep breath and waited.

He eased something that felt cold and metal in just a bit, then pulled it out again. He kept doing this, pushing a little further in each time until whatever it was settled inside of me and my hole clamped down comfortably around a small rod.

“Your anal training. This is the smaller plug, we’ll get the bigger one in when you’re ready.”

“I leave it in like this?” How was I suppose to walk? It felt like I had to go to the bathroom.

“Yes, Ruby.” He seemed tired of explaining things to me.

I reached back and felt what was sticking out of me. It felt like a round, flat knob.

“It’s a white jewel. It will be just visible between your cheeks. If you need to use the bathroom, you’ll have to take it out and put it back in yourself.”

When I walked toward the door to leave, I was surprised that it didn’t bother me as much as I thought it would. I just felt full back there.

Grandpa made small talk on the way to the car, “We don’t usually see pubic hair on women in this town, you’ll make good tips tonight.”

“Do I keep my tips?”

Grandpa laughed, “In a matter of speaking, yes.”

I lowered myself into the car onto the dildo and we drove into town.

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