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Introduction:

Ruby has settled in with her grandfather

When we arrived at the bar, my heart was racing and I was dripping wet again. The sensation of both holes being filled was something I had never experienced and I couldn’t decide whether I liked it or not. Grandpa had me clean the dildo when I got out but I was left to show off my wetness as we walked inside.

Grandpa greeted the bartender and told him I was reporting for a shift. The bartender looked me over, pausing at my crotch.

“The guys will love her.” They filled out paperwork while I surveyed my surroundings. The bar seemed what would be typical, though I’d never been in a bar at 18. Tables, barstools, everything was black and stainless steel. Then I saw the cages. Huge, tall, black birdcages suspended from the ceiling along one wall. There were five of them, each one with a hairless naked girl inside, covered in oil, rubbing her body and twisting and writhing. I blushed, praying that this would not be what I had to do tonight.

“Get behind the bar and get your instructions. I’ll be back in two hours to pick you up.” Grandpa left me there to fend for myself at my first job.

The bartender introduced me to two other girls, waitresses, who were dressed in revealing clothing and told them to show me the ropes.

The first girl had red hair and was muscular and fit, her breasts were huge and stuck out like headlights. Fake, she told me. “I’m Amber. This is Katie.” She gestured toward the curvy girl next to her with black hair and dark eyeliner. Katie was in a black vinyl cat suit, her nipples poking through and a slit of fabric missing from her crotch.

“I’m Ruby.”

“Student, right?” Amber eyed me up and down.

“Yes. I start in the fall.”

“The guys will love the hair. You allowed to keep it until school starts?”

I shrugged, “I’m not sure.”

“Well listen, we don’t make the drinks, we just serve them.” Katie handed me a notepad, “Write the orders down, put the table number at the bottom and bring them to the bar.” She pointed to a table map on the wall, “You get tables 1 through 6. Keep ‘em happy.”

Amber came behind me and reached over my head, clasping a 1” steel collar around my neck with a white heart dangling from the front. I flinched before I knew what was happening. “Easy, newbie. This will just remind the guys that you’re a student and the rules are different. They can’t take as many liberties with a student.”

“Liberties?” I felt naïve not knowing what to expect.

“You’ll see. Now, be friendly, introduce yourself to each table and ask how you can serve them tonight. You’ll get rude comments, just smile and wink. I know you’re new at this, but be flirty. If you act like a prude, they’ll lose interest and leave sooner. If you’re friendly and accommodating, they’ll stay longer and drink more. Get it?”

“I think so.”

Katie handed me a shot glass with liquid in it, “Drink this. One an hour. It will loosen you up a bit.”

I smelled it and went in for a sip, but Amber interrupted me, “Just pour it down your throat and swallow, love. Tequila isn’t for sipping.”

I poured all of the liquid into my mouth and took it in one swallow. Everything burned and I felt like gagging.

The girls laughed, patted me on the back and went to their tables to take orders. I waited for the burning to subside and looked at the table chart. I looked out into the bar and noticed one of my tables had a group of men just sitting down. They all looked near my Grandpa’s age.

I took a deep breath and walked to the table, smiling. “Hello, I’m Ruby, I’ll be your waitress. How can I serve you this evening?” It seemed like my best Brothel Madame interpretation.

One of the old men looked up from his menu and eyed me up and down, “A fresh, young student.” The other men ogled me in unison, all eyes on my pubic hair. One man reached out to run a finger through the hair and I managed to avoid flinching and jerking back as he tickled the tuft.

“I’ll have a number six and a light beer.” I scribbled quickly, remembering the man’s face.

The other men ordered and I thanked them and headed for the bar. As I walked away, I heard the comments about my ‘fresh young ass’ and something about my ‘tits’. I felt embarrassed and self-conscious. I gave the bartender the order and found Amber by the table chart, arranging a tray of drinks.

“Amber, um … are they allowed to touch us?” I had heard rumors about strip clubs and the strict rules about no touching before. Wasn’t this a strip club?

“Honey, they can do whatever they want to you, and you better let them. If you don’t, you’ll get reported.”

“Oh.”

“Don’t worry, students are off limits in a lot of areas. They’ll keep it pretty innocent. But watch Katie and I, because when you’re out of school and married … the rules change.” I looked at her collar and saw a black heart staring back at me.

“What does the black heart mean?”

“It means I have no restrictions.”

“Restrictions?” I felt like a child asking these questions, but this town was like a whole new world.

“Weren’t you raised in the lifestyle?”

“My mother left when I was little, and my father didn’t tell me about his lifestyle until ...”

“Your husband will give you whatever color heart he wants you to wear. It depends on their kink and their possessiveness. I’ve known some wives who never lose the white heart. If you have a steel heart, no one is allowed to even touch you.”

“Oh.” We were again reduced to possessions. I was beginning to understand why my mother wouldn’t have wanted her daughter raised like this.

When the old men were finished eating, they finished their beers and called me over to settle their tabs. I did a lot of smiling and ‘Yes, Sir’ing and collected their payments.

When I returned to the table with everyone’s receipt they all yelled, “Tips, boys!” as if they were reminding each other not to be rude.

One man with a beard rubbed my clit for about 30 seconds, another sucked one of my nipples and gave it a little bite, my anal plug was pulled out and pushed back in a few times, more clit rubbing and an open-mouthed kiss.

By the time I had collected my ‘tips’ and headed back to the bar, I was turned on and ready to beg anyone to fuck me.

I watched Katie and Amber collect their tips throughout my shift and noticed that they were rewarded with orgasms and rides on men’s cocks, even some blow jobs and swallowing. When I asked Amber how giving a guy a blow job was a ‘tip’ she told me that she loved doing it and swallowing their cum made her horny.

I was happy to be the student for my shift, I wasn’t incredibly good at blow jobs and I hated the taste of semen.

The two hours flew by quickly, though I was so turned on by the time my Grandpa came to get me that I was trying to form a plan to seduce him when we got home. The girls in the cages switched out every half hour, then they would walk through the bar, oiled up with a sexy, turned-on air about them. The men would fondle them and slap their asses, sometimes taking them from behind over a table. Watching them made me wet.

The atmosphere of the tavern itself was designed to be visually stimulating, and it was working on me as well. My ‘tips’ kept me on edge and I secretly wished now that I could be one of the oil girls just to get more than kisses and touches and sucks.

When we got home, I was told to shower while Grandpa waited on the toilet with a magazine. No privacy.

When I was finished, he handed me a towel without so much as glancing at me and I dried off. The anal plug had been washed and put back into the kit on the back of the toilet. I looked at the various sizes of plugs and wondered how the biggest one would ever fit inside of me. My hole cringed at the thought.

I was put to bed, my wrists and ankles cuffed again and the sheet laid over my body. The heat was turned up so I wouldn’t get cold and Grandpa turned off the light.

During the night, I heard a woman come into the house and go into Grandpa’s bedroom with him. The sounds of their wild sex kept me awake and frustrated. When I heard the woman moan and squeal as she had an orgasm, I pulled at my restraints and began thinking it would be worth the punishment to make myself cum. The restraints weren’t giving and I wanted to scream. Eventually they quieted down in the bedroom and I drifted off to sleep.

Grandpa woke me up when he was taking off my restraints. My arms were sore and I curled into a ball, enjoying the freedom.

“Breakfast, Ruby.” He walked to the door and stood, watching me.

I slowly sat up and looked on the nightstand for my clothes but there was nothing there.

“Breakfast and then some time in the sun. It’s 10:00, time to start the day well rested. No need for clothes just yet. Now use the bathroom and we’ll plug you before we eat.”

I followed instructions, my Grandpa watching me to make sure I didn’t touch myself, I assumed. When I had washed my hands, he came into the bathroom and bent me over to insert the plug again. It slid in easily this time, the sensation less of a shock.

“I think we’ll move up a size. The first one is always an easy one to get used to.” He washed the small plug and put it back in its place and chose the bigger size next to it. My hole resisted a bit this time, which seemed to please him.

The plug didn’t feel that much different, I just felt even more full as I walked naked downstairs. Breakfast was already made, sitting on the table.

“Ginger made breakfast this morning. Fruit and sautéed veggies. Drink all of your water, you’ll need to hydrate if you’ll be in the sun.”

I laid out in the sun for two hours, flipping over and listening to the ipod the school had provided me. The songs were dark and sexy and made me think of sex. I was desperate to touch myself, but terrified as to what the punishment would be if I did, so I tried to focus on the words of the songs. It didn’t help. I was constantly wet between my legs.

When the two hours was over, Grandpa told me to take a quick dip and get inside to clean up and get ready for some exercise after lunch.

The cool water felt good on my body and snapped my thoughts away from sex and calmed me down. I made a mental note to do more swimming.

I dried off with my towel and walked naked into the house. A beautiful woman was waiting with Grandpa in the kitchen.

“Ruby, this is Gladys. She does the waxing in town. Time to say goodbye to your hair, it will interfere with your training unfortunately.” He left the room and I turned to Gladys, who was smiling sweetly.

“Can you climb on the table, sweety?” She gestured toward a massage table she’d set up next to a stool with a pot of hot wax sitting on it.

The waxing went faster than I’d imagined and Gladys taught me breathing and relaxing to help with the pain. She plucked a few stray hairs she saw and then asked me to get on my hands and knees. I didn’t question it.

“Oh my. We’ll have to remove this.” She tugged at my anal plug and set it on a towel. Then she cleaned around my anus with a wipe and waited for it to dry before she started on the tiny fuzz that grew anywhere in the crevices.

When Gladys was finished, I was completely bald anywhere and everywhere between my legs and beyond. Gladys rubbed some lavender oil that she’d made over the sore hair follicles and announced that she was finished.

Grandpa made me bend over the kitchen table and checked my plug. He pushed it in and out slowly. When I moaned with pleasure, he decided it was time to go up a size again.

When the bigger plug was pushed into me, I grimaced and grunted in protest. This seemed to please Grandpa and he patted my ass cheek to let me know he was done. I felt stretched and full and it consumed my thoughts.

When lunch was finished, I found my clothes laid out on the bed, but they were different this time. The shorts were tiny and white with a thick seam in the center and I saw a plastic ring in the center of the crotch. I looked at Grandpa with a questioning expression and he held up what looked to be an 8” white dildo.

I pulled the shorts over my feet and when I got them to my knees, Grandpa snapped the dildo into its place and pulled the shorts up, positioning the dildo at my bald, wet opening. He pulled the shorts up higher than I would have and the dildo slid easily into me. When I looked in the mirror, the thick seam was finding its way into my slit, outlining my new, bald lips.

The thick seam in the back pulled the shorts up between my ass cheeks and barely covered them. The waistband was tight enough that the shorts would stay in place. My new bald pussy was sensitive and the seam rubbed parts of my pussy that I never knew could feel so good.

The shirt was a white cropped shirt made of thin fabric that hung loosely over the top half of my breasts, just grazing my nipples as I moved. I put on my jogging shoes and put my hair into a ponytail. As I walked, it felt so strange to have the dildo sliding ever-so-slightly in and out of me as gravity worked with the shorts to fuck me with every step.

I walked slowly, the feeling of both holes being stuffed was agony. I wanted to cum so badly. I had a whole summer of this torture!?

At the track, when I began to run my knees almost buckled under me. The other girls who had already been running were grunting and moaning in frustration, already having found their stride.

The jolting movements of running forced gravity to tug at the plug in my ass with each step, and the dildo bounced in and out of me, teasing me from the inside. All I could think about was my brother’s cock sliding in and out of me. I missed being fucked. The thoughts occupied my mind for three miles.

By the time I was done running, the silky fabric was clinging to my erect nipples like a second skin and my shorts were soaking wet, making my camel toe seem swollen. The seam had rubbed my clit just enough to tease me, but not enough to pleasure me. I was beyond frustrated.

When I returned to the stands where Grandpa was talking to a few men, all eyes were on me, panting and soaking wet, barely clothed.

“Good news, Ruby. I have several offers for marriage arrangements for you. Josh here has a son just about ready to graduate college with two other boys from town. They’ll be moving back in the fall, looking to settle down.”

“Yes, Sir.” I didn’t know what to say. I didn’t even get to choose my own husband?

“Their profiles will be sent over this evening, we’ll have a look and I’ll make my decision by the end of the summer.”

“Yes, Sir.” My heart rate was slowing and I was catching my breath, but I still felt like I was out of breath.

On our way home, Grandpa stopped by the grocery store and handed me a list. I made my way into the store, being fucked with every step. My pussy seemed to have a never-ending reservoir of juices. I was sopping wet and I could smell my musk.

At the register, the same boy checked me out and made small talk. He was so good looking, in my state I wanted to jump over the counter and fuck him until he collapsed.

“It’s going to be a hot summer, are you staying busy?” He smiled and stared freely at my breasts.

“Yes, Sir.” I smiled and imagined him naked.

“We should hang out sometime. I could introduce you to some other people our age. Most of us guys are headed to college in the fall so this is our last summer home. We’re making the best of it.”

“That would be fun, thank you Sir.” I was hoping there would be wild orgies and orgasms handed out like candy.

“I’ll contact your Grandfather.” Back to being an owned ‘thing’. He handed me my slip without being asked.

“Thank you, Sir.” I smiled and left. I didn’t look at the slip until I was in the car.
VIDEO STORE, TWO HOURS

Grandpa read the slip over my shoulder, “Ah, that will be later tonight. I’ll take you by at 9:00. Let’s get home, we have dinner to make and you have some videos to watch.

More of the machine. How was one body suppose to endure this kind of teasing? If only I could find a way to come without touching my clit. I would have endured any punishment if I could come.

When we got home, I was strapped down and the machine was set to fuck me. This time, with my anal plug inside of me. The double penetration was much like running at the track, but this dildo was far bigger and wider and the incredible feeling of being stuffed in both holes was overwhelming.

When the video came on and Grandpa turned on the machine to slowly begin fucking me, I moaned with crushing pleasure. Then came Grandpa’s warning, “There is still punishment if you come. Remember that.” He left the room, the door open and went into his bedroom.

The videos were nothing but beautiful naked women masturbating. Dildos, vibrators, slow finger fucking … any and every way I could imagine getting off, these girls were doing it. I was so envious of them. As the machine sped up, there were a few moments that I thought if I concentrated, I could come.

When the movies were over, Grandpa came and unhooked me, finding me the same as before, covered in sweat and panting like a dog in heat.

“I got a phone call from Ryan at the grocery store, he asked if you could go on a hike with some of the other kids in town. I told him tomorrow you could go during your exercise time.”

I thanked him between breaths.

“He’s a nice boy, I don’t think the lifestyle is for him. I expect him to make a run for it after college. But he insisted on sending his profile over for consideration tonight as well.”

“For marriage?”

“Yes, Ruby, for what else?”

“But he doesn’t even know me.”

“He doesn’t need to know you, he’s seen you.”

“But how is a marriage suppose to last if two people don’t even know each other?” I was sitting on the edge of the bed rubbing my wrists, sore from the restraints.

“Know each other? Do you think these men care what your favorite movies are? What your hobbies are? Your hobbies will be pleasing them. Your favorite things will the THEIR favorite things. You aren’t to have opinions, you’re to be obedient. This isn’t a proposal for a best friend, Ruby. It’s a proposal to be your provider and your husband.”

“Women here are treated like trophies; slaves! We have no opinions apparently, we do as we’re told and we’re exploited like sex objects every minute of every day.”

“You ARE objects, my dear. Marriage is an ownership. Men are the head of the household and women are their prized possessions. Your husband will take care of you, you’ll never want for a thing. In return, you make sure that HE never wants for a thing and keep yourself healthy so that everywhere you go, you represent him well.”

“And don’t misbehave. And call everyone ‘Sir.’” I was getting negative.

“Yes, Ruby. If you’re disrespectful, it looks bad on your husband. If you’re not pleasing to the eye, he looks neglectful.”

“It’s barbaric and sexist and demeaning if you ask me.”

Grandpa laughed, “If you ask the rest of the world, yes. But I grew to love my wife very much. She made me proud and treated me like a king. In return, I treated her like a queen.”

“And shared her with the entire town.”

Grandpa stepped forward and slapped my left cheek, hard. “Don’t you EVER disrespect my marriage. You know nothing about it. My job is to train you for this lifestyle and send you to school for a year to learn what I can’t teach you. When school is out, you can either run away to your mother or take the husband chosen for you and stay here. But I assure you, after a year in school, the outside world will look very different to you.”

I stayed quiet, afraid to say another word.

Grandpa turned his back to go upstairs. “Get dinner ready.”

“Yes, Sir.” I managed to find my voice, but it shook as I spoke.

We ate dinner in silence, me impaled on the dildo, daydreaming of a hiking trail orgy the next day.

After dinner, I was told to get dressed for work. I had completely forgotten about the video store.
On my bed was nothing but a black silk robe. I wrapped the robe around me and found some basic black pumps sitting beside the bed as well. When I walked into the hallway, Grandpa motioned for me to follow him into the bathroom.

I was bent over the sink and my robe lifted. Grandpa slowly removed the anal plug and washed it before returning it to the training kit. Then he showed me what he would be putting in my ass for work.

“This is your uniform for the video store.” It was a thick, very soft and rubbery anal plug that was definitely longer than the training plugs I had been using. Attached to the base of the plug was a long horse tail. “Real horse hair, very nicely made.” I looked at the bushy, long tail and tried to imagine myself walking around in public with only this, hanging proudly from my ass.

I was silent, and Grandpa laughed. “A little humiliation is good for the soul. Now let’s get this in.” I turned around and bent over, trying not to shed any tears of embarrassment.

I stole one more look at what was about to be put inside of me and my heart began pounding. It looked about 8 inches long, twice the length of anything I’d ever had up there. The thickness was about an inch and a half but widened to 2 inches thick every 2 inches of the plug. It was curvy and beautiful, but terrifying at the same time. The base where my hole would contract was a tiny steel rod before it attached to the tail.

Grandpa used plenty of lube on the head of the plug and slowly pushed it inside of me. I focused on my breathing as my ass opened wider and each curve of the plug. I couldn’t believe it all fit inside of me. When my hole contracted around the tiny rod, I felt stuffed so full that I was afraid to walk.

“This plug is incredibly flexible, it moves and bends with you and your body. It lets you enjoy the full feeling without any pain. Especially since it’s so long. It’s all necessary training for anal sex and keeping your body ready for anything that your future husband may need from you on any given day. No man has a 4” cock, am I right?”

“Yes, Sir.” I didn’t want to argue that I’m sure someone somewhere had one. I was trying to get my bearings and focus on anything but the full feeling of my ass. It wasn’t working well.

Grandpa asked me to stand straight up so he could put on my collar with the white heart. When I did, I was surprised that Grandpa had been right. The plug didn’t shift and hurt, but bended to my curves. I felt just as full, but there was no pain that a stiff rod would have inflicted shoved that far into me.

When the collar was on, Grandpa led me into the bedroom to look in the full length mirror. My hairless body stared back at me, my nipples hard. He turned me to the side and there I was, a naked girl with a black horse tail that reached the floor. The rod was just long enough and curved upward to hold the tale so that it looked like it really did sprout out of the top of my ass rack.

“Come on, pony. Let’s get you to work on time.” He tossed me my robe and we left.

In the car, when I lowered myself onto the passenger seat dildo, I flinched and moaned. Double penetration so deep in both holes was a new experience for me, and the car ride was delightful agony.

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