Ruby’s New Life Ch. 16

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When we arrived home from our day of exploring, Chef had dinner ready and everything was set. I was relieved.

I removed my sheer dress so I was in my house uniform only and my attendant took it upstairs to my rooms for me.

Daddy and Bill were speaking in hushed tones by the table, Miles was glued to his phone screen, and the food was waiting to be brought out.

Bill went to the head of the table where Kyle usually sat and cleared his throat, “Have a seat, everyone.” The men sat down and I waited to be included. Dad nudged Bill and gestured toward me, “Oh! Ruby, you may sit.”

I moved toward my chair and my attendant pulled it out for me. I lowered myself onto my dildo and was scooted closer to the table.

Chef brought out the first plates, service Bill first, then oldest to youngest male. I was last and we all waited for Bill to begin eating first.

“Why am I sweating? This makes me nervous.”

“Being the head of the household in this lifestyle is a big responsibility, Bill.” Dad sipped his wine and continued, “It isn’t only about free love and sex and being in charge. You’re responsible for the lives under you, expected to entertain and maintain your staff, keep everyone in line, dole out punishments if needed….”

“It’s a lot.” Bill began eating so we all took his lead.

“It is. Which is why Ruby had to attend finishing school to learn how to be here. She’s been on a crash course while she’s been here and I, for one, think she’s taken to it in an amazing way.”

“Thank You, Daddy.” I smiled and chewed small bites.

Bill put his napkin next to his plate and scooted his chair out, “I need to be excused for a moment.”

I softly put my hand on his arm and smiled, stopping him. I scooted out and lifted off of my dildo, kneeling down in front of him. He stared at me with a confused expression.

I unbuttoned his pants and freed his flaccid cock, assuming my hands-and-knees position with my back arched a bit , “Let me help.” I placed the tip of his cock in my mouth and waited.

Bill was in shock, he froze. I waited for him to make the connection and figure it out.

“Bill, will you just go already? We’ll be at the table all damn night.” Dad seemed frustrated, “I should have taught you all more than I did.”

“In her mouth!?”

“Yes, Bill, in her mouth. Ruby is trying to show you how life as the head of a household will be for you here. Damn!”

Bill let a little trickle into my mouth and swallowed, then a bit more came. He was testing the waters. Finally he let the flow happen and I swallowed down his steady stream. When he was finished, I didn’t move.

“Tap her on the forehead when you’re done.” Dad would be Bill’s instruction booklet while we did this, I could tell.

Bill tapped my forehead and I cleaned his cock, tucked it away and buttoned him up before lowering myself into my seat again.

I continued eating as if it were an evening with Kyle.

“This is going to be hard.” Bill was eating and in deep thought.

“Billy, I have books you can read. I’ll help you.” I smiled and patted his arm.

“Thanks, Ruby. Not sure this is all for me yet.”

“You can make your own rules in your own home, Billy. Some households are more extreme than others. If you choose to stay, we’ll find you a nice girl, you can alter her however you like and she will be this for you. Whatever you need her to be.”

“Alter her? Like Kyle did to you?”

“Yes. You can create your perfect companion.” It really did seem ideal to me.

Miles was listening intently, “Fuck yes! I want to stay here.”

Dad rolled his eyes, “I’m not sure you’re mature enough to handle it.”

Miles spoke up, “Hey sis, I need to pee too.” He pushed his chair out and unbuttoned his pants.

I looked at Bill, waiting for instruction. “What?”

“Billy, if you’re head of the table and I am your wife, then YOU make the rules about who I can and won’t serve.”

“Really? So I could still have a monogamous relationship?”

“Of course, if that’s what you wanted.”

“Otherwise, I have to share my wife with everyone?”

I laughed, “Sorry, no. I will find a book that explains this. You decide. There are varying degrees of sharing.”

“It would be kind of hot to watch my wife with other men though. Like you with Dad or Miles.”

“You can choose to have only family use her.”

“Hmm….” Bill had a lot of thinking to do and I felt a responsibility to pass on the knowledge I had learned during my time here. “Help Miles out, he’s gonna burst if he doesn’t get to do it at least once.”

“Yes, Sir.” I rose off my dildo and crawled under the table to Miles, taking his cock into my mouth so he could fill my belly with his piss.

“Fuck, Ruby, this is so cool! I could play video games all day and never have to get up!”

Dad slammed his fist on the table, “Which is exactly why you will not be doing this any longer.”

“But Dad!” Miles finished and politely tapped on my forehead. “I feel like I was meant for this lifestyle!”

“Then you can go to school here Senior year and get to know things from a child’s perspective before you try to take on any responsibility.” Dad excused himself and went into the study.

I looked at Bill, he seemed stressed.

“Don’t worry, everything will be fine. It doesn’t have to be decided tonight.” I turned to Miles, “I heard about a high school party this weekend that I think you would like. Someone at the Tavern mentioned it the other day, their son is the host.”

“Parents know about their kids’ parties here? Lame. I bet it’s a bore.”

“I think you should check it out. See what the girls your age are all about in this town?” I was trying to spark some interest.

“Yeah, okay. Whatever.” He put his napkin on the table and stood to go upstairs to his room.

I turned to Bill, “Maybe we should hire him an attendant for his stay here? Keep him calm?”

“An attendant?”

“Billy, damn! An attendant will dress him, bathe him, tend to his needs.”

“Let him piss in her mouth?”

I laughed, “Yes, she would do that too if we asked. Shave his balls, groom him, suck his dick….” I stood up and straddled Bill I his chair, “Fuck him to sleep, fuck him awake, pick up after him …. She would be at his beck and call.”

“You’ll help me find one?” Bill kissed me deeply and tugged at my gaziantep travesti nipple chain.

“Yes, Sir.”

“I could get used to this ‘Sir’ stuff.” He smiled and I unbuttoned his pants to lower myself onto his cock. I bounced and rolled onto his dick while he leaned back and watched me.

Chef and the kitchen staff began clearing the table and washing my dildo. We didn’t even notice them.

Billy reached out and unclamped my nipples, replacing it with his mouth. He had always loved to suck and flick at my nipples while we fucked. “I want to see your titties bounce.”

I braced my legs and bounced hard up and down on his cock, letting my tits bounce into his hands. It didn’t take long with the bouncing tits to send him over the edge. I knew his weakness. He roared and pulled me down hard on his dick, shooting deep inside of me and hugging me close.

“I love you, Ruby Girl.”

“I love you, Billy.” We had always only had each other growing up. Mom was gone and Dad was so busy with work all the time. “You’ll make a great husband here, I know it.”

“I will with you to help me.” He kissed my chest and turned his face toward mine. I kissed him softly and pressed against him to feel his warmth. We stayed that way until Dad called out to us.

“Get in here you two, let’s make a plan!” He was in the living room and we could smell the cigar smoke.

I lifted off Bill’s cock and sucked him clean, buttoning his pants again. My attendant took me into the small guest bath to clean me out and re-adjust my uniform.

When I was refreshed, I went into the living room and knelt down, legs spread, hands on my knees and eyes down.

“Dad, I don’t know if I could do this. It’s one thing with Ruby but …. A woman I don’t even know?”

“There’s a dating process, what do you think they do, throw a woman at you? You put in bids, there is a process. Damn, son. Ruby! At ease.”

I stood up and carefully walked toward Daddy and sat on his lap, facing Bill. Daddy wasn’t an equal like Bill was to me. Daddy had always been the one in charge when he was around. It made me feel safe that he was there.

“Ruby, grab me that book you were talking about on the shelf. Bill and I need to go over some things.”

“Yes, Sir.” I fetched the book and gave it to Daddy.

“Ruby, you’re crowding me, take a turn on the sybian.”

“Yes, Sir.” I had my attendant roll the sybian into the center of the room and help me get on. He secured my feet and turned it on a nice, slow, rhythmic speed. Our sybian had a remote, so he took the remote and handed it to Daddy.

Things were quiet for a moment. I got my rhythm down and began enjoying the ride. I felt my nipples in their clamps and let the sensations spread down into my pussy. My eyes were closed and I could feel their eyes on me, watching my body interpret the pleasure it was feeling with moans and flushed cheeks. The machine was amazing.

“Look at your sister, Bill. That is a woman who knows her place and that is what this lifestyle is all about.”

“A plaything for all the men in town?”

“No! You’re not getting it. She is unmarried and used quite often, yes, but she knows that when those vows are taken, she answers only to her husband. She obeys, she serves, she takes on the responsibilities that her husband does not want. When he’s stressed, she fucks it out of him, when he’s angry, she will be his whipping post, when he entertains, she will be his shining glory; she will be his alter ego until death parts them. It’s between them to make the rules and once the rules are set, they will obey them religiously.”

“But the men do whatever they want.”

“Within the restrictions of their marriage, but they do have rules to live by as well. Watch.” Daddy changed the rhythm of the sybian until I was riding like a mad woman, the sensations were intense. Then he switched it to a bounce. Gravity took over and with my hands on my knees, it bounced its faux cock in and out of my body.

“Do you hear it, Bill?”

“Year what?”

“Listen to your sister! Do you hear how it’s making her feel?”

I was getting close to coming and my moans and yelps were becoming desperate.

“I hear it. Yes, I hear it.”

Daddy stopped the sybian cold and my eyes opened, half crazed. I was panting.

“Come here, Ruby.” My attendant released my feet so I could go to Daddy, “Lower that pussy onto my dick.” Daddy had his beautiful cock out and I turned around with my back to him, straddled his lap and lowered onto him, letting him fill me up.

Daddy leaned be back so my head was resting on his left shoulder, then he pulled up me legs at the knees, spreading me wide and begin pounding in and out of my pussy. I wrapped my right arm around his neck and felt every inch of him inside of me.

“You like that, Ruby?”

“Yes, Sir.”

“You like Daddy’s cock fucking your tight pussy?”

“Yes, Sir.” He felt even better than the machine.

“Are you close? You sound close to me.”

“Yes, Sir.”

“Cum on my dick.”

I felt it building and wailed desperately, “Yes, Daddy.”

“Cum on your Daddy’s cock.”

“I’m cumming, Daddy!” The orgasm gripped me and I arched back but Daddy grabbed my hips and shoved me balls deep onto his cock so he could feel every spasm in my pussy. I could feel his cock stiffening and growing, ready to shoot.

The orgasm was still racing through me when Daddy roared, “I know how much you like your pussy filled with Daddy’s cum. Take it all, Ruby Girl. Take Daddy’s cum and …. AAAAHHHHH! That’s it, milk my dick with that pussy.” He shoved me off of him, “Clean it.” I turned around and took him in my mouth, sucking and slurping him clean, licking our cum off of his beautiful clean-shaven balls until there was nothing left.

“Come straddle my lap.” I went to him and straddled him. He shoved two fingers inside of me and made that ‘come here’ motion, rubbing my G-spot. I moaned and closed my eyes, “Open your eyes. Look at Daddy when I play with your pussy.”

I looked at him, through him while the pleasure just kept going. He took his fingers, covered with his jizz, and put them in my mouth. I sucked and licked them clean. He did this over and over, bringing me close to orgasm and then making me eat his cum out of my own pussy. I was struggling to maintain, Daddy always knew how to push my limits, even now.

“You’re so close, Ruby Girl, I can feel it.”

“Yes, Daddy.”

“You won’t cum until you’ve swallowed all of my cum, do you understand?”

“Yes, Daddy.”

He got rougher, making that scooping motion with his fingers, then he switched to 3 fingers and my moans got louder and perfectly desperate. I couldn’t take it anymore, it was becoming impossible to hold back.

He pulled them out, covered in more jizz, an shoved them into my mouth to be cleaned. The orgasm subsided a bit.

When he went back in to abuse that magical spot, I went wild, bucking on his hand and begging, “Daddy, please! Please let me cum, I can’t hold it back! God please, please let me!”

In one swift motion, Daddy had me on my stomach over his lap and was spanking me, “I say when you cum, you understand?”

I was crying, “Yes, Sir”

WHACK! WHACK! I screamed.

“You cum when I tell you and you do what you have to do to hold back.” He spanked me until my cheeks were on fire but it only made my pussy wetter. “Get back up here.”

I straddled him again, desperate and crying. He went back in to get more of his cum, bringing me so close I almost lost it before he pulled out and shoved his fingers into my mouth again.

The torture continued until I couldn’t taste any more of Daddy’s cum on my fingers.

“A good girl wouldn’t beg. Get off me.” I stood up and stepped back, getting into my submissive sitting position, still sniffling and shaken.

“See, Bill? They sent her home from school because there wasn’t anything more they could teach her. Called me, told me she was broke, that they had ruined her she was so obedient. But I know my daughter. I know how to push her, I know her weakness and I can still bring her down.”

“Dad, I don’t know if I have what it takes.”

“That’s what we’re here to find out.”

The next few days were spent exploring the town, visiting Kyle’s parents and Daddy even left my brothers and I to play alone while he went to connect with people from his past and catch up.

Daddy loved Kyle’s parents and Mother and I had a wonderful time playing with our dogs while the men discussed Lifestyle and answered all of the boys’ questions. They had SO many questions. Miles had already made up his mind he wanted to move here. If Daddy wouldn’t, then he would have to live with Grandpa and Molly.

I watched Bill closely as we went about our time. He seemed curious, but hesitant. I decided to talk to Daddy about it.

“Is there anything I can do to help?” Daddy was having a cigar and brandy in the sitting room and the boys had decided to go one their first solo trip to the Tavern.

“You can talk to him in a way that I can’t. Feel him out, see what is holding him back. He may just fit into the outside world better, it’s been too long.” Daddy seemed disappointed.

“Why does that bother you?”

“Your mother would have rather the boys took to this lifestyle and you were the one to reject it, not this way.”

“Well, you trained me in ways I didn’t even know I was being trained, what about the boys?”

“Encouraging them to fool around with their sister wasn’t enough?” He smiled and took a puff on his cigar.

“You know what I mean, Daddy.” I was so curious about my own predicament. “Daddy, what other things did you do when I was young to prepare me for this?”

“Why are you so curious about this?”

“I’m a freak! All of my friends are still at school and I’m here, a shining star of finishing school and everyone treats me like a leper. I want to know why I took to it so well. How did I break?”

“You’re not broken, Ruby. Their system is designed for a different type of mind, that’s all.”

“Did you ….” How could I ask him?

“What? Did I molest you as a child? Ruby, for fuck’s sake!”

“Well Dad, I don’t know how else to explain what has happened to my mind!”

“You were trained on textures, allowed to fool around with your brothers….I didn’t delve into the things that parents in this town would do.” He sipped his brandy, “It was small things you wouldn’t have noticed, they don’t cross any lines.”

“Like the pudding?”

“Like the pudding. Bare bottom spankings, the children’s books you read…”

“My books?” They had all been fairy tales and normal kid stories.

“They’re lifestyle books. They’re similar to the same stories other kids read, but altered just a bit. The moms in the stories are dressed provocatively compared to outside moms, more submissive…references are made to ‘grown up time’ and ‘daddy’s work friends’ or ‘mommy and daddy’s special friends’ you just hear the terms and it’s normalized.”

“I hadn’t even thought about it. I guess you’re right, I just never thought about it.”

“All kids here are raised that way, some with far more questionable ways when it comes to kids. Your mind is just …. Special, Ruby.”

“I don’t want to be special.”

“I know. But our families are some of the oldest in the Lifestyle, you come from a long line of submissive and obedient women. Maybe you were just bred for this?”

“I’m a thoroughbred how wonderful.” I rolled my eyes. “In the meantime, my fiancé wants nothing to do with me. I scare him.”

“I could always move back and you could live with me until you find another husband.”

“But Daddy….Kyle has already altered me! I am already HIS! I want to be his.”

“There are so many people working on this, Ruby. They’re going to figure out what to do for you. Trust that those in this lifestyle know what they’re doing. Kyle has faith, you need to have it yourself.”

“Maybe if he saw me while you guys are here!? I feel different when you’re around. Relaxed.”

“That might be a good idea, actually. In the meantime, enjoy the time with us and don’t worry so much. Everything will work out, I promise.” He smiled that Daddy smile and for a second, I really thought it was going to be alright.

I slept well that night, I loved our house. I had made this a home. I would do everything in my power to make sure this became our home together. I had a new determination.

At breakfast, Chef wowed the boys and the conversation was boisterous just as it had been growing up. I ate light, drinking the piss of 2 men was more than I was used to.

I asked to be excused and went out to check on Blake. He needed release, so I presented to him. I let him mount me and take his time, knotting me so I could make myself cum. When he finally flopped out of me, followed by a river of doggy cum, I had lost count of my orgasms. It was a release I needed to clear my head.

My attendant helped clean me up and when I arrived in the sitting room where I heard voices, Daddy introduced me to a stern-looking woman.

“This is Lydia. She has tailored some conditioning audio for you according to the plan that has been decided on for you.”

“Hello, Ruby.” She didn’t crack a smile, just got down to business, “We have some audio for you to listen to much like you did while you were in school. All spare time, while you’re exercising and sleeping….the decided protocol is a new one, so you should know it’s experimental but it’s been approved by your father, grandfather, and your fiancé so it’s a go.” She didn’t make it sound like I had a choice. I didn’t though, did I?

“When do we start?” I was ready to try anything.

“We start today, but I would like to explain this to you first so you understand what is going to happen.” She gestured toward the couch and we sat down, “Your mind has created a deep, cavernous place where you can retreat in your submissive state and …. You sort of go on submissive autopilot.” She saw me starting to object, “Now, this is exactly what the training is designed to do, you’ve done everything right, Ruby. It’s just that it’s never worked completely like this before and everyone is a bit on edge.”

“I feel fine!” I had to say something.

Daddy put his hand on my shoulder, “Ruby, there are plenty of men in the Lifestyle that wish their women had reached your level, believe me! But your fiancé desires less of a …. Perfect result. Just listen.”

Lydia continued, “What we are going to try is creating another compartment in your mind where you can retreat to and be …. Free to express your personality as you do when you’re with family. More relaxed more …. Human.”

“It makes sense, I just feel like a freak.”

“I completely understand. But this new place you can get to will be your everyday place to stay in your mind. You’ll still be able to reach that deep place, but there will be code words to access it that you will not be given. It will be situational. Understand?”

“You want to divide my brain up, got it.” I didn’t really care, I was just ready to get back on track to marry Kyle and begin our life.

Lydia handed me my iPod loaded with new audio and music. I thanked her, put in the ear buds and went out to the pool to swim and tan. It would be cold but …. Thank goodness for the pool heater. I needed some sun.

And so were my days for about a week. Music, fucking Blake, servicing Daddy and my brothers, exercising and talking in-depth with Bill about the Lifestyle.

Miles had already decided he was staying. Getting attacked by 3 girls at a party sold him instantly. I had to laugh, he had always been so horny and so eager.

Kyle was coming home for a few days and I spoke with Chef about a special homecoming dinner. I invited Kyle’s parents and Lydia was coming to help start some dialogue and step in if things didn’t go as planned.

I had some reading time to brush up on my etiquette during group situations. It was fuzzy, we weren’t married, it was his home, we hadn’t discussed limits….I called Lydia in a panic. What if I fell into submissive robot mode?

Lydia assured me she would call Kyle and discuss the situation and he would bring home a collar with a heart so I could easily identify the limits he expected of me for the evening and make it clear to everyone else as well.

I prepared for Kyle’s arrival, my attendant chose a gorgeous sheet black jumpsuit with ankle-wrap heels that was stunning when it draped over my well-groomed body. My hair was curled, light make up just the way Kyle preferred….I smiled because I felt like a wife.

Daddy knocked on the door, “Kyle’s pulling in.”

I quickly got up and headed down the stairs. Kyle walked through the door and saw me. He looked nervous, so I smiled. I finally reached the bottom of the stairs and he walked to me, “Ruby, I’ve missed you so.”

“Me too.” He kissed me, testing the waters. I melted into him and his kiss became more passionate. “Can we have a moment?” I pulled away.

“Yes, of course, in my study.” We shut the door behind us and he turned to take me in his arms, “I see more of you in there. Is the new therapy helping?”

“You’ll have to tell me, it happens so gradually that I don’t notice. But Kyle….”

“I prayed it would work, I didn’t want to lose you.”

“Kyle, please listen, I need to say this.” I took a deep breath, I had his full attention, “I do think the therapy is working and having my father and my brothers here has helped immensely. I really wanted you to see me in this environment.”

“And I’m so happy I came home to see it!” Kyle seemed like an excited child.

“Yes, me too, but I also need to tell you that I was comfortable in that place.” Kyle looked confused, “Part of the conditioning was losing my fear. Fear of not being in control, fear of being hurt … fear of all of it. But I learned about every aspect of this lifestyle, the good and the bad, and I realized that none of it is really scary.”

“But Ruby, you were an absolute sex bot! It was the most uncomfortable thing I’ve ever seen! It scared me to death, I thought I’d lost you.” I could see the panic in his face.

“Kyle, none of it was scary because I trust you!”

He turned to me, “What?”

“You will be my husband, my protector, my guide…you will never put me in a position that I will ever need to be afraid of anything. I trust you. Because I trust you, I have no fear, don’t you get it?”

“I guess I never thought of it that way. But Ruby …. I will have to guard those code words with my life and I can honestly say I will never use them myself. I can’t watch that. That woman isn’t my fiancé.”

“You never have to use them. But is there someone you trust who can let that woman out once in a while? For release? To explore that fearless world?” I took his hands in mine, “Please?”

“I will find someone. For you.” He smiled, leaned in and kissed me. I felt like he had completely accepted me and I felt so close to him. I didn’t want to stop. I kept pushing, undressing him.

“Ruby, not until we’re married.”

Our wedding night. The night everything would change.

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