Ruby's New Life Ch. 15

Ruby's New Life Ch. 15

Days went by; I was left out of all discussions as to what my future would hold. I was allowed to do all of the shopping so I could earn Tavern time and video store time. They deemed it necessary for my mental health. It was also good for business. I was quickly becoming very popular in town and there was a following of men who kept tabs on where I would be working and when.

They also resumed my anal training so that my body would be ready and willing as it should be, regardless of what they decided. I was so thankful for that.

The machine had been removed from my room and there was no reason to bring it back in. Mental training was on hold, they had no idea what to do with me.

One morning when I awoke, I saw that Grandpa had laid out clothes for me. He hadn’t done that since …. Well, since before.

Just a simple crop top that really only covered my nipples, leaving the bottom half of my tits exposed and a pleated, very low-cut plaid skirt that just covered my pussy but left most of my ass exposed. White knee-high socks and Mary Jane 4” heels.

It was exciting to be dressed again, and I put my hair in messy pigtails to celebrate. When I went down for breakfast, Grandpa called to me from the living room.

When I turned the corner, my heart raced. My father and my brothers were sitting with Grandpa and stood when I entered the room.

I felt a part of me I had forgotten come forward and I squealed and ran forward to hug them all.

“Daddy, it’s so good to see you!” He hugged me tight as if he never wanted to let go.

“Your Grandfather thought you could use some familiar faces right now.”

“He was totally right!” I couldn’t stop smiling.

My older brother, Bill, had matured from a wild Frat boy into a man. My younger brother, Miles, would have just turned 18 and I couldn’t believe how much he had filled out. They were a welcome change.

Grandpa cleared his throat, “We thought maybe you would all like to spend some time together while Kyle is away on business for a week or so. The house is empty and the staff is at the ready….Ruby, you haven’t been home in a bit, this could be a nice break for you.”

“Yes! Oh thank you, Grandpa!!!!”

We ate a beautiful breakfast that Molly had made and Grandpa even put my dildo back on my chair. Things felt like they had shifted, the mood felt lighter.

When Molly and I were done cleaning up after our meal, I got in the car with my family and directed them to our house. Things were just as I’d left them and it was perfect. My family was just what the house needed. I showed them all to a guest room and checked in with Chef for the menus. Kyle’s attendant had gone with him on his trip and to my surprise; no jealousy crept into my thoughts. He was taken care of and I was free to entertain my family while he was gone.

The boys were elated that we had decided to have the pool heated and ran out to swim in the cold morning air. I found Daddy in the sitting room, thumbing through a book he had found on the shelf. I stood in the doorway and obediently waited for him to notice I was there.

“Oh Ruby!” He shut the book and returned it to the shelf before turning and smiling my way, “I was just admiring your book collection.”

“I haven’t had a lot of time to track down all the volumes I want, but we have a good start on the shelves.” The open gaps I had filled with statuettes of bound women, lovers intertwined, masks, small plants, and even some antique sex toys that I found fascinating. You would never know I was trying to disguise sparse book shelves.

“Your home is beautiful, you’ve done well.”

“Yes, well, not as well at school….”

“Yes, your grandfather filled me in. Let’s not talk about it, let’s just enjoy our time together this week. I haven’t been to this town in years, I would love to explore and just spend time with you.”

“Yes, Daddy.” I smiled, “Would you like some coffee? Chef just brewed some fresh.”

“That sounds divine, let’s chat a while.” He sat on one of our chairs and I turned to gesture toward Maid and she hurried to the kitchen to get a tray.

I sat in a chair that shared a small table with Daddy’s chair and waited for him to choose the topic of conversation.

“You look divine, Ruby, really. The changes Kyle made are tasteful and beautiful. I hardly recognized you. You look ready for sex every minute.”

“I am.” I smiled as Maid returned with the coffee tray. She set it down and we went through the formalities of how Daddy took his coffee and serving before I dismissed her and encouraged the conversation again.

“Ruby, I want this time to be just like old times. But I want to know if you have any questions for me about how you were raised or why I made the choices I did. Have you seen your mother?”

“I haven’t seen her, no. I decided to write her and explain that I was choosing the lifestyle and sent her a very kind goodbye.”

“That’s nice, honey.”

“Why didn’t you let me go with her when I was young?”

“I couldn’t bear the thought of letting you go. Your mother was so angry….I naturally assumed being raised in the lifestyle; she would have understood what I wanted. But she didn’t. She had been away from here too long. Throwing fits over pudding….it was a bad time.”

“Pudding?” I laughed.

“It’s early training, Ruby.”

I studied his face as I sipped my coffee, “Training? I was told I had no training when I arrived here.”

“Your grandfather wasn’t a big part of our lives; he was very upset with us for leaving. But I did start your training early. Childhood training is innocent enough; you never would have thought anything of it. It isn’t sexual.”

“What does pudding have to do with it?”

“Young girls are given vanilla pudding with every meal, it’s just tradition.”

“I remember the pudding, but how does it have anything to do with training?” It made no sense.

“It’s a texture thing. Simply learning to swallow thick, sweet pudding creates a positive association for …. later in life.”

“For cum swallowing?” I was being blunt.

“Fine. Yes, for cum swallowing. You had chocolate pudding every day until you were 10, when I switched you to vanilla.”

“I remember that.”

“When you were 18 and started fooling around with Bill, I knew it was time to work on the formula so we started altering it.”

“Altering it how?”

“Jesus, Ruby, why do you make me say it?”

“Daddy, I don’t know any of this! I was kept in the dark!”

“We made the pudding by hand then and …. It was mixed with ejaculate on an increasing level until you came here. To get develop your palate…”

I didn’t know how I felt about it but my programming told me that it was perfectly logical to prepare me for the lifestyle. “Thank you, I think.” We made awkward eye contact and sipped our coffee quietly for a bit.

When we were done with coffee, Daddy insisted on touring the grounds and seeing the house. When we came to the dog enclosure, Blake ran to us wildly excited for attention. I opened the gate and Daddy greeted and pet him.

“This is Master Blake.” I smiled down at my small lover.

“Master? You really have come a long way.”

Blake came to me and buried his snout in my pussy and began licking. It was divine. When I heard his dominant growl, I turned and knelt on the cold ground and put my ass in the air to present for Blake like a good girl.

Black sniffed and licked and wasted no time jumping up and mounting me. I moaned with ecstasy, it had been a while since I had experienced animal abandon during fucking. It was amazing.

“Daddy, can you hold him back so he doesn’t knot me? I don’t have time for it right now.”

“Sure, baby girl.” Daddy moved forward when the knot began to swell and made sure Blake didn’t succeed in plugging me with it.

Having Daddy there, watching me get fucked by Blake was turning me on. I wanted to show him all that I had learned; let him know that he had made the right decision sending me here.

I felt Blake’s doggy cum filling me up and spilling out of me. I felt the orgasm building and began to moan wildly.

“That’s it, Blake, fill up your bitch like a good boy.” Daddy was encouraging him and I felt so proud.

When Blake was finished pumping his seed into me, he came around in front of me and sat, waiting. I sucked and cleaned his doggy cock, spreading my knees wide and pushing as much cum out of me as I could.

Daddy spoke up, “Blake, Clean!”

Black went behind me and began licking and cleaning me, his tongue going up into my pussy to get it all. I didn’t even know he knew this command. Daddy had so much experience, it made me love him even more.

When I was clean, we went back inside and the boys were having a snack with Chef.

“Wow, sis that was hot.” Bill seemed impressed.

“Thank you.” I smiled and excused myself so I could be freshened up by my attendant.

I was dressed in my house uniform with a sheer, black house dress over it. It was like a thin veil covering the chains running around my beautiful new body. I looked like a Goddess.

When I came back downstairs, the boys were still in the kitchen with Chef, having drinks and telling stories.

Bill noticed me first, “Ruby! Remember that time we fucked in the baseball dugout at our high school!?”

“Yes, Billy, I remember.” I smiled and took the drink Daddy had made me.

“I thought my heart would pound out of my chest. Imagine someone finding me fucking my sister!” The boys laughed and clinked glasses.

I took a sip of whatever Daddy had given me, “What is your plan for the day? Shall we go out or …?”

Daddy slugged back the last of his drink, “Let’s go out. I want to see if this town has changed at all. Shopping?”

Miles spoke up, “Actually, Dad, I’ve been missing Ruby like crazy and seeing her like this ….”

“You need some time with your sister then?” Dad smiled, “I’ll let you young boys catch up with your sister. I have some calls to make.” Dad pulled out his cell phone and went outside to make his calls.

“Miles, you never could control your urges!” I giggled and he snatched me up into his arms right there in the kitchen. He kissed me deeply; his teen passion had only gotten stronger since I’d been gone.

Bill moved behind me and I could feel his dick, hard and pressing into the back side of me.

We fell into our old routine from home, after school. The boys removed my house dress, lifted me up, each one taking a leg, and Miles started fucking my pussy wile I lay back on Bill’s chest and he pushed his way into my ass. They knew just how to handle me and how to make us all happy.

Miles obviously hadn’t been edging himself to control his orgasms. It wasn’t 10 minutes into our fucking that he lost control and came inside of me, burying his face in my tits for comfort. It brought back so many memories.

Miles softened and pulled out of me, Bill was still pumping away at me, whispering dirty memories in my ear, “I’ve missed fucking you, Ruby. I love you so much, baby sister. Remember when I took your virginity at home?”

We both remembered. It was an amazing day; two horny teens using one another to make it through the day.

I felt a hard cock in my pussy and it didn’t feel familiar. I opened my eyes to see Chef, holding my other leg and watching his cock slide in and out of me.

I remembered Kyle mentioning that there were no clearly defined boundaries in this house, so I just enjoyed the double penetration and Bill’s sweet whispers.

Chef was a champion. His cock was a gorgeous size and filled me up nicely. The 2 of them fucked me steadily until I moaned that I was ready to cum.

Chef changed his angle and rhythm and started really hitting my G-spot while I rubbed my clit and enjoyed all of the sensations.

“Billy, I’m close. I want you to come with me.”

“You say when, Ruby girl.” I could hear it in his voice how hard he was holding back.

It built and built and when I knew I was going over the edge I yelped, “Billy now! I’m cumming now!”

He grabbed my head and pushed it to the side, biting firmly on my neck as I came, screaming and clenching around Chef’s dick. Chef lost it watching us and filled me up with his jizz too.

I was set down and I made sure to clean Chef’s cock so he could get back to work. I thanked him and Bill and Miles followed me upstairs to my room.

“Watch and learn, boys.” My attendant gave me water douches and cleaned me up, oiling me backup and smoothing out my uniform before he touched up my hair and makeup, then put on my sheer house dress again.

“Why did Kyle choose black?” It seemed so depressing.

“Master thought it would be a nice contrast with your hair and eyes.”

I looked in the mirror, “He’s right. He’s always right.”

We went downstairs to tear Dad away from his phone meetings and we all went into town. I found Kyle’s car dildo attachment and made sure I rode shotgun so I could use it.

“Sis, this is so hot! You’re like, being fucked while Dad drives!” Miles was young and dumb and fascinated with everything he was seeing.

“It’s even cooler. This dildo is a replica of Kyle’s dick.” I glanced into the back seat.

“No way! That’s fucking romantic.”

Dad smiled and glanced over at me, “I thought this would be a good chance for the boys to see what the lifestyle is like so they can choose a path for their future.”

“That’s a great idea, Dad!” We pulled onto Main Street and Dad parked the car.

We spent the afternoon touring the shops, showing the boys how women behaved in this fairytale place. I was on my best, submissive behavior and the women we saw in town were as well. Our final stop was the Tavern. Bill and Miles were so worked up from everything they’d seen; I hoped there would be a black heart available.

Luckily, I spotted Amber behind the bar. When she saw me and then my father and brothers, I swear I saw her salivate. She started moving toward us.

“Welcome, gentleman.” She smiled her sexiest smile and glanced at me, “Ruby…”

“Amber, hello. This is my father and these are my brothers. I am showing them around town, thought they might like to see what the Tavern has to offer.” I smiled wickedly.

“You working?” Amber looked excited.

“Not officially but ….” I looked over at Daddy, “I could help out if you like?”

“Let’s order some drinks, boys!” Amber guided us to the lounge area and my men leaned back and ordered their favorites.

Their eyes were taking it all in, glued to the cages, curious about the back rooms.

Dad wasn’t saying anything, so I spoke up, “If you see someone you like, you can request some private time in the back….”

Miles eyes widened, I could tell he was interested. I handed him a price menu and he began studying it. Dad took the menu from him, “This one needs to learn a little impulse control.”

Amber came by with our check, asking if we wanted anything else. Daddy said we were ready to go.

He gave her a credit card to run, filled in a monetary tip when she came back, thanked her and started out the door. We looked at one another, confused.

“I’m sorry, Amber I …. I don’t understand.”

“It’s okay; he’s been away for a long time.” She shrugged.

“But my father grew up here …. “ It was puzzling.

“Have a fun time with your family, Ruby.” She smiled and started cleaning the lounge area of our discarded drinks.

In the car, comfortably impaled on my dildo, I asked Daddy if he knew the customary tipping routine.

“Yes, I know, Ruby. I just need to introduce the boys to this slowly or it can go really wrong. Miles needs to learn to control his urges and Bill…..well Bill needs a wife.”

My head turned sharply to face Dad, “What!? A wife!?”

“It’s time, Ruby. I can’t have you getting married before your older brother. He needs to decide which world he wants to make his home in, the outside world or this one.”

“I see.”

“He’s had job offers already and he isn’t even graduated. It’s time to start thinking about which colleagues he will be making his friends.”

Daddy was right. Outside colleagues couldn’t be entertained here; the less people who knew this place well, the better.

“How can I help?” I wanted Bill to be happy with whatever he chose.

“Just do as you have been. Live life as it is here, let him see.”

“Act as a wife here would?”

Daddy thought for a second, “Yeah, like that. Let him experience it, introduce him to some people you’ve met.”

“I can do that.” I smiled and enjoyed the ride, wishing it was Kyle’s cock inside of me.

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