Ruby’s New Life Ch.9

When we arrived at the school, I had never seen so many nude girls all in one place. Each of us was escorted by our fiancé or father. Kyle had found my black ballet flats and that was all I wore. I had even been told to leave my plug in the case, which Kyle had packed into my dorm supplies. I had moved up to the size Kyle wanted me at and he was very pleased. It was 9” long and 2” in diameter, only tapering down to 1 ½” at the base. It literally felt like his entire cock was stuck inside me every time I wore it.

Giving blow jobs and pleasing him had me so horny I couldn’t stand it. I was trying to be obedient and hadn’t attempted to masturbate. I was hoping school would be some release for me in that area. My mood would certainly improve.

My dorm room had two beds and my roommate had already arrived. She was a brunette with a bull ring in her nose and dark red lipstick. Her breasts were fairly small and her nipples were itty bitty. She smiled and said hello.

“I’m Ruby. Nice to meet you.” I set down a box on the bed.

“I’m Alice. My fiancé just left for the office, I should follow.” She bowed her head toward Kyle, “Excuse me, Sir.” She moved around him and left.

“I was hoping Naomi or Tasha would be my roommate.” I was a tad disappointed.

“Alice will do fine, Ruby. This isn’t time to socialize and gossip, it’s time to learn and reflect and mold yourself into the perfect wife for me.” It sounded awfully selfish the way he said it.

“Yes, Sir.” I didn’t argue.

We unpacked my things, laid out my uniform that I would need in a bit for the formal gathering and orientation and headed for the office to check me in and get my official schedule.

The headmaster was a foreboding man. He was tall and bald and very stern. “Slaves will keep their eyes lowered in my presence.” I lowered my eyes to the floor.

I heard the slap a split second before I felt it. The headmaster’s riding crop had whipped at my left breast and I whimpered as I jumped. “I didn’t hear a ‘Yes, Sir’, slave.”

“Yes, Sir.”

“Yes Sir, WHAT?”

“Yes Sir, I will keep my eyes lowered in your presence.”

“Better. Now keep in mind that no matter how relaxed your life may be at home, this school is very formal and incredibly strict. We do not carry out elaborate punishments, but too many corrections and you may be sent home to your fiancé for proper realignment.”

“Yes, Sir.” I was beginning to worry that this was a monumental mistake.

Kyle spoke then, “Sir, I’m sure Ruby will be one of your best students. She wasn’t raised in this lifestyle and is a recent addition to our town. She has developed incredibly quickly and I know she’ll make me proud.”

“Let us hope so, Sir.” The headmaster handed Kyle my schedule and they discussed payments and deadlines and visiting and phone call schedules. Kyle would be sent progress reports and psychological evaluations regularly. “We’ll keep you up to date as to how your property is being cared for and how said property is progressing in her studies.”

“Thank You, Sir.” When we left the office, Kyle snickered. “I felt like a schoolboy in trouble in there!”

“He’s terrifying.”

“You’ll do fine, darling. Just be sweet and obedient and try your best. Everyone here is learning. You may be behind compared to those raised here, but from what I’ve seen you do – you’ll outshine them all in no time.” He kissed my forehead and we headed back to the dorm room.

My roommate was giving her fiancé a farewell blow job apparently. He was incredibly rough with her, holding her by the throat. We turned toward my bed and began unpacking my things, trying to give them some privacy. I could hear him cursing and calling her a whore. I was grateful Kyle was not cruel.

When everything was packed, Kyle helped me into my uniform. The top was a thin white tank top, if it could even be considered that. It had wide straps and the bottom came down just far enough to cover my nipples and nothing more. The bottom of my breasts bulged out below the shirt.

The skirt was a nice quality blue and green plaid schoolgirl skirt but the hem came just to the top of my pussy in the front and rested ½ way down my ass in the back. My pussy was completely exposed under the hem and ass was nearly fully visible as well. I had 8 sets of this uniform in my drawers, along with 20 pairs of sheer white knee-high stockings which I put on carefully before slipping my feet into the plain black, pointy-toed high heels.

“Your hair will always be kept in a high, clean ponytail. No make-up allowed other than chapstick.” Kyle handed me an organic tube of lip balm and put some on before pulling my hair up.

“I also need your engagement ring. No jewelry allowed if it isn’t a piercing.”

“Yes, Sir.” I removed the beautiful ring and placed it in Kyle’s hand.

“It will be back on your finger before you know it.” Kyle smiled and slipped the ring into his pocket.

My roommate was left to dress by herself, no tearful goodbye for her and her fiancé. Kyle walked me out of the dorm and told me to follow the other girls to the sanctuary for orientation.

He pulled me to him and lifted my chin, “I will speak with you soon and I will be here every visiting day, I promise.” He kissed me deeply before turning to leave.

“My, my! Must be true love!” I turned to see my roommate sneering in my direction. She didn’t fill out her uniform quite as well as I did. She was beautiful but obviously cynical.

“Is it such a bad thing to fall in love with the man you’re going to marry?” I was certainly falling in love with Kyle more and more each day.

“You’re property, not his true love.” She started walking to class and when I did the same, she steadied her pace beside me.

I couldn’t let it go, “I disagree. I may be property, I may be submissive and cater to his every whim but that doesn’t mean we can’t have feelings for one another.”

“Must be cozy in that dream world of yours.”

“Just because you’re treated differently doesn’t mean….”

“Treated differently? How do you think you’ll be treated once you’re married? Like that? Dream on.” She rolled her eyes.

“We’ve discussed our arrangement at length.”

“Well, Pollyanna, what could you possibly have to learn here, then?”

Naomi suddenly appeared on my other side, “She wasn’t raised in the lifestyle, Alice, you know that. Don’t be a bitch.”

“Obviously. She acts like there will be flower petals and scented oils in her bath every night like a pampered wife.” She turned to me, “You’re property. You’re a sex slave and nothing more. Get over yourself.”

“Alice!” Naomi looked enraged, “I’ve seen her and Kyle together, he’s very respectful and I think he’s head over heels for her. Stop it!”

“Bullshit. You know who he dated all through school, don’t you? My best friend. When he applied to be her husband, her family chose for her and they were split apart. They were both heartbroken. He’ll never love you like that. You’re a cheap replacement.”

“I don’t know much about that, but I assure you what we have is far more than a business arrangement for sex.”

“We’ll see.” She smirked as she walked faster ahead of us to catch up with some other girls.

“Don’t worry about her,” Naomi put her arm around me, “Her best friend is a cunt. Kyle stayed with her because she put out and would do whatever she was asked. I knew Kyle in school, he didn’t love her. He respected all the girls, but he certainly never looked at her the way I’ve seen him look at you.” She winked at me and I smiled.

“That’s my roommate.”

“No way! That sucks so hard. Her fiancé is a dick. I know plenty of stern husbands that show very little affection but he’s … sadistic and cruel at best. I’m surprised she doesn’t have scars all over her body by now.”

“That’s sad. I feel sorry for her.” Maybe I could get through that cool exterior and find a human in there.

“Don’t. She’s always been like that. Her father has been fucking her since she got her period but pretends like she’s invisible otherwise. She’s damaged goods. She ended up with exactly the kind of guy I always thought she would.”

When we entered the sanctuary, it resembled the inside of a Catholic church. It was beautiful. We were shuffled in and we all sat in the pews. We found Tasha and all three of us sat together, talking about how horrible our roommates were. Tasha’s roommate cried all the time and was a sniveling wimp. I wished I had that problem.

“Ladies!” The hall suddenly got quiet. The headmaster was in the pulpit, “Classes will begin tomorrow, be sure you explore the campus and find your classrooms today so that you will not be tardy tomorrow. Tardiness is not accepted here. Be sure to also read through the school rules and policies thoroughly. There are no first day exceptions to punishments.”

The headmaster glanced down at a paper in front of him, “There will be no sexual contact tolerated between students. If you are caught in this manner, you will be expelled. Your future husbands will certainly reconsider their marriage plans if that happens. I expect obedient behavior from you all. I now introduce my assistant headmistress.”

A tall, voluptuous woman in a gray form-fitting long-sleeve dress took his place, “You may call me headmistress. I am here to go where it is not appropriate for the headmaster to venture. There is nowhere on this campus that will be private. We will know your every move and there are cameras on you at all times, monitored carefully by a well-trained surveillance staff. If you are caught masturbating, stealing, bullying, having sex or otherwise breaking campus rules, you will be caught and you will be punished accordingly.”

Headmistress sneered at all of us, “Your fiancés will be notified of every infraction. There are no secrets about your life here. You will soon be dismissed for lunch. After lunch, you are free to adhere to your standard exercise routines, etcetera. We are not here to interfere with the rules your fiancés have set forth. Your classes will be during the first part of the day, your time to reflect and train as only you and your fiancé have decided is what your afternoons are to be used for.”

She stepped down and she and the headmaster walked together up the aisle and out the door. Each row of girls dismissed themselves quietly and one large, long single-file line bee-lined for what I assumed was the cafeteria.

We had assigned seats for lunch and I suspected Mother had some influence over where we were seated as Tasha and Naomi and I were together at a table with three other girls. Each of our seats was fitted with a replica of our fiancé’s cock for us to lower ourselves onto, which didn’t surprise me in the least. I tried not to judge the size of the others. The other girls were nicer than my roommate, which I was thankful for. Their fiancés were very strict, though one girl was over the moon for hers.

“Is Blaire here? I haven’t seen her.” I was still very curious about her dentures.

Tasha looked around, “I haven’t seen her either but I’m sure she’s here. Her fiancé wouldn’t let her skip out on this.”

We chatted and I got to know the other girls. They were nice enough. Tasha and Naomi had grown up with everyone at the school, so I felt a little left out and behind in everything.

When we were finished eating, we cleaned our trays and explored the campus. It was beautiful. There was an Olympic-sized swimming pool with lounge chairs all around where I could sun myself while the weather was still nice. We even found the tanning bed room where I could go on rainy days.

My classes were not difficult to find and we had a good time running the track. I was feeling a bit more settled in.

When I returned to my dorm to put in my anal plug and listen to some music while I read the school rules, my roommate was already in her bed reading. I noticed she had clothespins on her nipples and when I glanced between her legs, I noticed a cluster of the same pins. Her face was red and she was trying very hard to concentrate.

“Don’t stare, it’s rude.”

“I’m sorry, I just…”

“He likes inflicting pain. I am here to build my tolerance. I don’t need distractions.”

“You got it.” I took my plug into the bathroom and used lube before slowly inserting it. It felt good and almost comfortable to be filled again.

I laid on the bed and read the handbook. We were to be very organized, clean and regimented. It was like sex slave military school. There wasn’t anything I couldn’t handle. As long as I did what I was told, it seemed I would be fine.

After dinner most of us were too exhausted to do much. I did find out that Tasha and Naomi were in my building, even if we weren’t roommates. We agreed that we would meet in the common room every evening to do our homework. Each class didn’t have homework, but we had a list of reading material, worksheets and writing assignments that had deadlines.

I got ready for bed, put my worn uniform in the laundry bag and removed my anal plug, washing it and placing it back in the kit. I ignored Alice as I settled into bed, choosing the next conditioning Mp3 and falling asleep to it peacefully.

My first class the next morning was Restraint. I was nervous. What if we couldn’t hold back?

Each class was only 15 girls, which made it a more intimate setting. This class had three short rows of lounging couches, each with a disposable pad laid out where you would sit and a small table beside it. Each table had a standard-issue Doc Johnson vibrator and a bowl of cleaning wipes.

We each chose a couch, sitting politely on the edge, waiting for the teacher to begin. The teacher was a sweet-looking woman with nothing too remarkable about her. All the teachers wore the same tight-fitting gray dress.

“My name is Mrs. Kettle. I expect proper behavior from you, but by no means is this a class with strict rules. You are here to learn to control our own impulses, re-direct your mind and thoughts and overcome your own primal urges to satisfy your husbands first. Practice makes perfect. Ladies, if your husband doesn’t want you to have an orgasm, you simply won’t. This you must accept. How to do that is what I’m here to help you with. Lie back please.”

We all removed our shoes and laid back on our lounges.

“Now. Restraint is all about mental focus. The nerves in your body will react with gusto if you are not concentrating. Most of you will get off on the idea that you are being used and controlled. That will work against you when you are trying to hold back your orgasm. Now, please turn your vibrators on to the highest setting and place them on your clitoris.”

I reached for the vibrator and turned the top until it was buzzing violently, then placed it against my swollen, enlarged clit. The sensation was overwhelming. I tried to focus on the teacher’s voice.

“Take your mind out of your bodies, ladies. Count the squares on the ceiling, recite Shakespeare in your head, think of something that turns your off or disgusts you, whatever you need to do to ignore the sensations between your legs!”

I looked up at the ceiling and tried to find a pattern among the tiles. My clit was begging for release. I could hear other girls losing control already. I literally pushed against the feeling, as if I was pushing a cock out of my vagina. I took deep breaths and thought of how Alice’s fiancé had treated her. How could a man who treated me like that ever get me to climax? I decided he was my distraction.

I focused on his soul-less expression, his cruel words and his hand on Alice’s throat. I blocked out the sounds of pleasure surrounding me. My clit felt swollen and ready to explode. Finally, the vibration was too much to ignore and my orgasm split through me, making my back arch as I gave in to it. The feeling was amazing and I felt relaxed for the first time in weeks.

When I opened my eyes, Mrs. Kettle was standing above me. “You’re the last, my dear. Congratulations.” She turned and moved toward the front of the classroom. “That was pathetic, ladies. What if your husband was administering the stimulation, telling you not to climax until he allows it? How many of you would be severely punished right now? Would it be worth the orgasm to endure the pain? Of course it wouldn’t. Let’s try this again…”

And on it went for an hour. As the hour wore on, we were better able to control it just from exhausting the nerves in our clits. For a total of three rounds, I was the last to finish. It was the tiniest of victories, especially since if it had been Kyle working on me, I knew I wouldn’t be able to focus on anything but him and I knew it would mean failure.

When class was over, we cleaned our vibrators and our dripping pussies and threw the wipes and disposable pads soaked with our juices in the trash on our way out. I kept to myself and made my way to Sensual Pain.

Alice bumped into me on the way out the door, “Tell me, just what makes a newbie to this lifestyle so good at restraining herself?”

I smiled, “Thinking of your vile fiancé.” I pushed passed her and giggled to myself as I walked to the building next door.

Sensual Pain was taught by a short, stern man with very little patience. When we arrived in class, each girl was fitted with nipple bands that were to remain on until the end of class. Different sizes were chosen and I was given the largest size, of course, with my new modification. The teacher seemed impressed with my nipples and spent more time than necessary ‘stimulating’ them if you ask me. They were stimulated constantly.

We were told to read the passage written on the whiteboard at the front of the room and respond to it in essay form, due at the end of class. That was it.

One girl began whimpering from the beginning of class and by the end was nearly panting like a wild animal. The pain was intense and it made it very difficult to focus on writing anything with much thought. My essay was total shit, that much I knew.

Toward the end of class, the teacher moved around to each of us and removed our bands, letting the blood rush back into our nipples. That pain was worse than what I had endured for nearly an hour. Then my own whimpers began.

I tried deep breathing and clenching my fists, but it made it impossible to write. Before any of us were finished, we were asked to pass our papers to the front.

“Ladies, your concentration was juvenile. You must overcome the pain and focus your thoughts. Your bodies belong to your future husbands, not to YOU. They must respond as he asks and you must make that happen. If you can’t focus on a simple essay while your nipples are bound, how will you focus on sucking your husband’s cock or that of his colleagues properly while the same is happening? To be a good, obedient wife, you must put your own needs, your own pain and your own discomfort out of your mind. Sensual pain should DRIVE your behavior, not hinder it. I will read your essays and assess where you are at first class. This will be included in your psychological profile and in your final assessment as to your progress when the term is over. Good day.”

When I left class, my nipples felt back to normal but they were sore and sensitive to the touch. I was mentally exhausted already. I had no idea there was so much mentally to being subservient to a man. It was far more exhausting than being rebellious, which came naturally to me.

I was looking forward to Sybian class as I rushed for the building, my tits bouncing as I jogged along. This building was further than the rest and I couldn’t risk being late. My pussy was dying to find out what a Sybian could do….

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