Dating My Grandfather Ch. 03

***Thanks to all for keeping up with this slow-burn story. The plot turns the corner into the true beginning of Tess and Everett's sexual and romantic relationship with this chapter. My profile has details about my release schedule. Enjoy!***

Mei knelt between the legs of Everett Ambrose Halloway.

"She's ready to move on?" he asked. "You mean it?"

Mei stared at the impressive naked shaft of Everett's cock that stood at attention right in front of her face.

"She was capable enough two days ago, Sir," Mei said. "But I needed to know that she wouldn't revert."

"Is she still trying to probe you for information?" he asked.

"She stopped a few days ago," she said. "I followed your advice."

"She is quite a challenge," he sighed. He reached forward and gently stroked Mei's dark hair. She did her best not to move or make a noise. Her eyes were locked onto his leaking tower. "You've done well. My daughter did quite a number on her. To think a granddaughter of mine could be so undisciplined at twenty five."

"She loves you a lot," Mei said. "She's very curious about your relationship to me, Elisa, and Carmelina."

"You've told her that she can ask me," Everett said.

"Many times."

"Then you've done all you can do."

Mei felt her mouth fill with drool. Her eyes threatened to unfocus, but she kept steady.

Everett looked down at his newest head housekeeper. She still had some discipline to learn as well but there was no need to unduly punish.

"Go on," he said. "Serve."

Mei let out an exhale of deep relief.

"Thank you, Master Halloway," she said. She reached forward and took his cock into her small hand and pulled it toward her mouth.

*****

Two weeks had passed since I moved into Halloway Manor and my custom tailored wardrobe had finally arrived.

The majority of the clothing that I had packed had already been donated. I had been surviving with barely more than a few pairs of yoga shorts, tank tops, and casual sweaters.

My strict grandfather only let me wear those things in my room and on weekends, so I was stuck wearing the house staff uniforms during the day and borrowed items in the evening.

The arrival of my new wardrobe also marked another important day for me.

It was the day when I finally graduated from laundry duty.

It was my grandfather's belief that I needed to learn structure, authority, and challenge through the process of learning to do basic chores.

It had been a humbling experience to realize that something as basic as laundry had taken me over a week to learn to do properly.

Every weekday, I had to wake up early, go down into the basement, and spend all day with Mei.

Mei was my least favourite of Grandpa's three head housekeepers. Elisa and Carmelina were professional and followed the rules as well, but both had more natural warmth.

I had hoped that I would settle into my new routine, but each day of chores continued to feel like torture. I knew that I was being a little childish and dramatic, but spending all day in a stuffy uniform sorting laundry made me want to scream and throw a fit.

My only release was my fingers.

I had been seeing a local guy, Chase, for a week or so but he had been bothering me recently. Although he was older than me, he felt so immature. He only talked about how hot he thought I was and he fucked like he had somewhere to be.

So I had resorted to masturbating. A lot.

The most shameful part was that I had taken to fantasizing about the housekeepers sleeping with my own grandfather as I got myself off.

Chase had alluded to rumours about Grandpa hiring busty women to be escorts, and all of his staff fit the bill.

I had no real evidence that he had anything but professional relationships with any of them, but the idea had consumed me.

After a few days of trying to probe Mei, Elisa, and Carmelina for information, I simply stopped. It got to be embarrassing. All they did was tell me to talk to Grandpa about it.

As if I would ever bring up something like that.

What would I say?

'Hey, Grandpa, do you fuck the women you employ who are a fraction of your age?'

It was bad enough that he probably knew that I was asking his employees about it, although not in so many words.

I thought about all that as I masturbated.

It was four in the morning.

It used to be that I would stay up that late after a night at the bar or a night of manic painting.

These days it meant that I was waking up before breakfast so that I could rub one out.

I had gotten really good at using my fingers. Back in the city, I couldn't imagine masturbating without my vibrator, but it had disappeared from my luggage when I moved, so I had to make do.

That was another thing that I had yet to ask Grandpa about.

The only way I found comfortable to masturbate with my generous 30K cup bust was to push my face into my bed and stick my ass way up.

It was a humiliating pose, but it kept my huge tits in check. Plus, I was starting to think that the submissive and embarrassing position was part of its effectiveness.

After I shook into a pleasant climax, I took a brisk shower and then opened my wardrobe.

I had spent hours sorting through my new clothing, but I had tried very little on.

I knew that I had been measured specifically for the clothing order, so I wasn't worried about anything not fitting

It was unlike me to do so much preparation. I scowled at myself to think that Grandpa's lessons might be rubbing off on me.

I still thought it was silly that Grandpa required me to get fully dressed just to walk to where I was going to train for the day. It was so much work for just a few minutes of traveling through the mansion when I would only have to change into a stuffy maid outfit anyway.

The only thing countering my grumpy mood was the fact that I no longer had to train under Mei.

I knew that I was being a little hard on her. She was nice enough, and she was very charming during dinner, when everybody was more relaxed, but something about her still rubbed me the wrong way.

Maybe it was how she acted whenever Grandpa was around.

It was subtle, but I noticed. The way her cheeks flushed a little more. The way her voice became that much more high pitched.

I got dressed in one of the more casual pieces that I could find that didn't fall all the way into lounge wear. It was far more formal than anything that I ever would have worn before moving into Halloway Manor, but my goal posts were shifting.

It was a charcoal dress with a midi-length hem. The waist was sculpted and it had a high, asymmetrical neckline. I had to admit that I thought I looked fantastic.

A knock came at my door.

My heart beat fast. I had a feeling it was him. Grandpa.

I almost never saw him outside of dinner time, and - except for the first night - that was always a group affair with Carmelina, Elisa, and Mei joining us.

The last time I had seen him alone was when he had walked me to the laundry room a week and a half earlier, and he had been annoyed at me for being under-dressed.

Therefore I was excited for him to see me dressed properly. I rushed to the door and threw it open.

"Master Halloway, Sir," I said with a bright smile.

"Tessa Jean," he said.

He was dressed in a grey three-piece suit. His perfectly styled thick hair made him look so handsome. I didn't even mind that he used my full first name.

I smiled up at him and kept my hands down at my side.

"I am glad that you are learning the importance of structure," he said.

I felt myself deflate. He had complimented me on my appearance when I wore one of Elisa's dresses on my second night in the manor, but there had been nothing of the sort since.

"Do you like it?" I asked.

"Don't be crude, Tessa Jean," he said. "Come now, let me show you to the kitchens."

I followed behind him. I felt my huge breasts clap together with tight restraint under the structured curve of the tailored bust of my dress. I just wanted him to notice me. I didn't grow up with a father. Mom was always more like a roommate. Couldn't my grandpa at least tell me that I looked pretty?

When we got to the kitchen, I felt great relief to see Carmelina standing there.

Grandpa detailed that I would be learning to make breakfast and - just like laundry with Mei - I would do it every day until Carmelina was satisfied with my progress.

It was only after he left that I noticed Carmelina's uniform. It was distinctly less modest than anything I had seen her wearing to that point.

It had all the trappings of the traditional maid outfit that she normally wore - black and white colours, frills on the shoulders, doily-style lace - but the shape was tailored to her shapely body, the skirt was only down to her knees, and there was a healthy amount of tightly-packed cleavage visible.

"Is that the normal kitchen uniform?" I asked her.

"It's a very feminine act to prepare food," Carmelina said. "It's only natural."

I wasn't all together comfortable with her answer, but I had learned to not talk back. It never got me anywhere.

So I changed into the same uniform as Carmelina. I felt very exposed. It wasn't like I didn't wear tight and revealing outfits, but normally it was when I was out trying to get laid, not making breakfast at the break of dawn.

I had been far more nervous about cooking than I had been about laundry, but it turned out that I was something of a natural in the kitchen.

Carmelina was a very good teacher, but my instincts were also in the right place. I cracked the eggs perfectly, I put just enough cheese into the omelets, I spiced everything just right.

"You did extremely well this morning, Tessa Jean," she said after I helped her deliver the meals to all the lesser staff in the mansion. "I will tell Master Halloway that you can begin preparing breakfast for him as soon as tomorrow morning."

This news surprised me.

I was surprised partly because of how quickly she approved my work, but moreso because of the fact that I would be making breakfast specifically for Grandpa.

"I'm sorry," I said. "What do you mean by that?"

Carmelina smiled at me. She had such easy warmth to her. It was impossible to not feel calm and happy in her presence.

"Master Halloway wishes to spend more time with you," she said. "He requested that you bring him his breakfast every morning once your cooking was adequate."

I stood stunned for a moment. When I felt able to speak, I asked the first thing that came to my mind.

"And I'll be wearing this?"

*****

Training to make breakfast took up far less of the day than laundry did.

Laundry was effectively a full shift, but after making breakfast, I was done my work for the day with a number of hours still until noon.

I considered going to find my grandfather. I had so many questions for him, but the thought of asking any of them was daunting.

I had changed back into my charcoal dress to leave the kitchen and while it would have been my instinct to change into something more comfortable at the first opportunity, I did no such thing when I went back to my room.

My phone was on my nightstand - I wasn't allowed to bring it to training - and I opened it to check my dating apps.

The thrill had been gone for days, but I still checked out of habit.

It was so strange. I had a high sex drive, loved men, had free reign to go on dates or have men over, and yet none of the guys on the app appealed to me.

My standards were not normally very high but the past week I had found myself finding small faults in all of them.

Instead, I put my phone back on my nightstand and walked back out into the mansion.

I barely noticed the fact that I wore heels all the time since moving into the mansion. Even the low platform heels I had on would have made me squirm in discomfort just a few short weeks ago, but it had become the new normal.

I walked past the reading nook where I had spent most of my weekends to that point.

I walked past the room that Elisa had told me I could use to paint to my heart's content during free time.

I hadn't gone in once.

I walked out of the East Wing and towards the side of the mansion that I had more nostalgia for, the side of the mansion where I would stay when I came to visit Grandpa and Grandma when I was younger.

Before Grandma passed away and Grandpa and I stopped talking.

I thought back to the funeral, when I didn't know what to say to him, when I had to face the fact that he was a man, not part of an immortal pairing that my grandparents had represented.

My memories were so strong that I didn't notice that I was walking straight toward Grandpa's room until I heard him speaking.

"Next Thursday, that's rather short notice," he said. "But you said the Treels will be there?"

I knew that Grandpa was still heavily involved in attending social gatherings. I knew that he considered it a responsibility of his fortune to continue to mingle and be involved in the business community.

The conversation wasn't of particular interest to me, but it felt so taboo to be listening to him when I wasn't invited.

"That's fine," he said. "Mark me down as attending. Yes, with a plus one. Have a good day, Trevor."

I hear the distinctive sound of an old landline phone being hung up. I suddenly realized that I was standing right outside his door.

I decided that I would have to let my presence be known. Without the distraction of a phone call, he would certainly hear me if I tried to walk away.

But then he spoke again.

"Well that's irritating," he said. "I know that you're not free next Thursday."

My heart skipped a beat. For a silly moment, I thought that he was talking to me.

But then I heard another voice.

A muffled voice.

"Mmfffthh."

Although it was just a noise, I recognized it as Elisa right away.

I couldn't help it. I moved closer. I peeked around the door.

Grandpa was sitting in a padded ladderback chair, turned three quarters away from me.

On her knees between his legs was Elisa, sucking his cock.

My eyes bulged. The angle wasn't great, but I could still make out what was happening, and I could definitely tell that my grandfather was hung.

I only looked for a moment. Just enough to realize what was going on, and then another moment longer to make sure that my eyes weren't deceiving me about his size.

But that moment was just long enough for Elisa to notice me.

Our eyes locked.

She smiled as best she could with her mouth stuffed with cock and then she returned to her service.

"Carmelina will be away too," Grandpa continued.

I backed away as quietly as I could and then rushed back to the East Wing.

*****

I couldn't get the image out of my mind.

I tried to read and it didn't help. I tried to masturbate and it didn't help. Hell, I even finally went into the painting room, but I couldn't get anything on the canvas.

There was no way to parse what I was feeling. I had been convinced that Grandpa had a sexual relationship with his three head housekeepers, but seeing proof still felt world-shattering.

Or was it the fact that Grandpa had the biggest dick I had ever seen in my life?

Maybe it was the fact that Elisa looked so happy.

Maybe it was the contrast between Grandpa's stern rules and the lewd act that he was allowing while conducting a business conversation on the phone.

My mind spun in circles, but deep down I knew that all my thoughts were just avoiding what was really on my mind: I would be bringing my grandfather breakfast in a slutty maid outfit.

*****

I trembled the entire time in the kitchen while I prepared breakfast the next morning. I hoped that my nerves would screw up my cooking enough so that Carmelina would tell me I wasn't actually ready, but I had no such luck.

"Go on," she said when I had the plate prepared. "You know where his room is."

I could feel my huge tits bounce with every step I took.

I could see my cleavage jiggling out of the bottom of my peripheral vision.

My grandfather was training me to cook breakfast for him. My grandfather liked getting blowjobs from women in their 20s with massive boobs. My grandfather wanted me to come into his room alone in a tight little maid outfit.

I held the tray under my arm like Carmelina taught me and I knocked on his door.

"Master Halloway?" I called out. "Breakfast is ready."

"Come in," he said.

His voice was so low. It was extra gravely and rough from sleep.

I opened the door and made sure that I was holding the tray properly before I walked into his bedroom.

I brought his breakfast and placed it down on the table that Carmelina told me to. It was the same table that he had been sitting at the day before, when I had spied on him.

Grandpa himself was sitting on the edge of his bed. I had never seen him so disheveled.

His hair was a mess and he was only wearing a dark blue silk robe.

"Should I leave it here?" I asked, with no small amount of awkwardness in my voice.

"Please, Tessa Jean," he said. "Stay."

He stood up from the bed and I did everything in my power to not look down at his crotch, certain that he would have a bulge big enough to protrude from the loose folds of his robe.

"I didn't bring breakfast for myself," I replied.

He chuckled. I smiled despite myself. His laugh was so full of life, no matter its form.

"Nor should you have," he said. "I plan for you to switch to a more appropriate diet starting today. No more bacon and eggs for you."

I felt immediately indignant.

"I'm sorry?" I replied.

"Don't be difficult, Tessa Jean," he said. "This is for your own good. You are twenty five. You will not have the perfect figure without effort for much longer. We need to start now."

I felt a rush of conflicting emotions.

First was deeper indignation. How dare my old man of a grandfather start talking about what sort of body I should have or dictating what I could eat? It was insulting.

Next, I felt betrayed, as if he called me into his room in the morning with an ulterior motive beyond spending time together.

Finally, I felt a burst of shameful warmth. It was backhanded and shallow, but he had complimented me again. I had a perfect figure.

"Grandpa, I-"

"-I will not hear it," he said. His voice was firm but he did not raise it. "Tell me, you have been in Halloway Manor for how long?"

"Two weeks, Sir," I replied.

"And tell me, how has been your experience?"

"Frustrating," I said. "I've been forced to wear what you want me to wear, forced to do laundry, forced to abide by your nonsense rules."

I looked at him, expecting to see anger, but his face was calm.

"I am not surprised that you find it challenging," he said. "Your mother gave you a disrespectful amount of freedom. Is frustration the only element of your experience?"

I exhaled sharply through my nose.

"Well, no," I said. "Dinner is really nice. My room is beautiful. My weekends have been very relaxing. I've never slept so well in my life."

"So then you might say that you are responding well to structure?" he asked. A small grin twisted up his face.

I realized that he was referencing his own list from my first night in the mansion.

Structure, authority, and challenge.

It was as if he knew that the words would stick with me.

"I still have a problem with authority," I snapped back.

He smiled and motioned towards a chair on the other side of the table as he sat down in front of his breakfast.

"Elisa tells me that you haven't painted yet," he said. "Why is that?"

I felt startled by his change of topic, but I didn't want to waste time alone with my grandfather, no matter how annoyed I was with him in the moment.

"I don't know," I answered honestly. "I thought it would come easily."

"Art is unpredictable," he said. "The room is there for you whenever you have free time. I'm sure that inspiration will strike."

"Thank you, Sir."

The conversation was light and easy after that. I noticed after a few minutes that I was calling him 'Grandpa' and he wasn't correcting me.

After precisely half an hour passed, he sent me on my way.

I felt elated after such a wonderful time, even with the way it started, but my mood dropped when I got back to my room and saw that Grandpa hadn't been joking. Instead of my usual bacon, omelet, and toast, there was yogurt and fruit.

That night for dinner, I put on one of the more bold items of clothing from my new wardrobe.

The fit of the dress was simple and form-fitting, running down to my ankles with a high neck, but the colour was a shocking pink. It had been Elisa's suggestion when I was looking through the catalog and I felt compelled to follow her advice.

I arrived just as Mei arrived and I flashed her a warm smile.

She smiled back, although she did appear a little confused.

Dinner conversation was warm and lovely as usual, but it suddenly took on a different tone for me. I realized that I looked forward to dinner because of the company and because of how loose Grandpa was, but after he was so informal that morning, the dinner version of him no longer felt like enough.

That night, I couldn't help but let the image float back into my head of Elisa on her knees for Grandpa.

Although I had been fantasizing about Grandpa fucking his staff for over a week, it suddenly felt different. It wasn't just my imagination, I had a real image to refer to.

It wasn't a fantasy, it was reality.

I remembered how huge Grandpa's cock was. It looked so virile and hard, more than I thought would be possible at his age, even with how healthy he was and how good he looked.

My fingers slid between my legs as I pushed my ass up into the air.

I was completely naked.

It turns out that I was also completely soaked.

"Fuck, your dick is huge, Grandpa," I moaned to myself in my room. I realized that I was imagining myself in Elisa's position, kneeling before him.

'Put it in your mouth, Tessa Jean,' he said in my mind's eye.

"How is it going to fit, Grandpa?" I asked.

'Structure,' he said. 'Authority. Challenge.'

I shook as I came on my fingers without warning.

*****

By the time I brought Grandpa his breakfast the next morning, I had already pushed my taboo fantasy out of my mind. Clearly I was going a little crazy cooped up in the mansion, and with nobody else around, my mind went to fucked-up places.

I didn't think about how I hadn't replied to Chase or any other of the eligible bachelors on my phone for days.

"Master Halloway?" I called. "Breakfast is ready."

I came in with the tray, and Grandpa was in a similar state to the day before.

"Do you know how to work a stovetop espresso pot?" he asked. He nodded over to the kitchenette that was part of his enormous master bedroom suite.

"I don't, Grandpa."

"Get Elisa to teach you," he said. "I'd like you to make it for me in the morning."

"Yes, Grandpa."

Although I answered demurely, I had mixed feelings. Grandpa had talked a big game about equality to me that first night, but he was clearly pushing me into submissive behaviours. I gathered the courage to ask him about it.

"I understand that you want to teach me about structure, authority, and challenge, Sir," I said. "But do those things have to take the form of such archaic gender stereotypes?"

He looked up at me with a half smile.

"They do not have to, Tessa Jean," he said. "But I consider myself an excellent judge of character, and you are a woman who I believe will thrive in a traditional role."

I wasn't sure what answer I had expected, but it wasn't that.

"Oh," I said.

"I forgot to tell you yesterday," he continued. "This meal is delicious. I admit to being suspicious that Carmelina cleared you after just one day, but I should know better than to not trust her."

I blushed at the compliment.

The morning before, I had forgotten about my revealing outfit after a few minutes into the conversation. That morning, however, Grandpa reminded me with his eyes.

He looked while he ate his breakfast. Actually looked. It wasn't a passing, shameful glance. It wasn't an accident. His eyes dipped to my tits - his own granddaughter's tits - and took an appreciative look into my tightly-packed cleavage.

"Grandpa..." I said softly. His eyes moved up to meet mine.

"Yes, Tessa Jean?" he asked.

"Nothing."

The next morning, I was excited to show off how I had learned the stovetop espresso for him. I proudly watched his expression as he took a sip.

"It's perfect, Tessa Jean."

"Thanks, Grandpa."

My days became centered around that half hour with him in the morning.

It was hard to explain. Our conversations would be pleasant and warm, but nothing life-changing. It was everything around it. It was the fact that I would be the first one to see him in the morning, that I would be taking care of him, that we only had thirty minutes and so it felt special.

One full week later, he repeated a question from that first morning.

"So," he said. "Tessa Jean. How would you describe your experience living at Halloway Manor?"

I froze and blushed.

I knew that he had a victory. I didn't care.

"I feel free," I said quietly.

"Elisa told me that you painted on the weekend."

"I did. A scene from a series I started years ago."

"The fantasy world, correct?" he asked. "I love the idea of a story world told through images, not words."

Emotion bubbled up inside of me. I had no idea that he remembered.

"Yes, Sir," I said. "Ennoria."

"It's a beautiful name."

I smiled at him and did my best to not let tears well up.

That day, as soon as he dismissed me, I painted until it was time for dinner.

I noticed that Grandpa didn't look at my body during dinner, although he had continued to do it during our morning time together. I didn't think about it much, only that I enjoyed the attention.

As I walked back to my room that night, I noticed that Elisa was right behind me.

I wasn't entirely sure why I hadn't brought up the fact that I had seen her on her knees for my grandfather, despite the fact that we had locked eyes, but part of it was surely the general tone of boundaries and respect that Grandpa commanded over the mansion.

"Is everything alright, Elisa?" I asked her when I got to my door.

"Absolutely," she said. "However, Master Halloway wanted to inform you that you are free to wear what you wish for breakfast service tomorrow."

"I'm not sure I understand, Elisa."

"Goodnight, Miss Halloway."

I spent an hour staring at my wardrobe.

I was free to wear what I wished?

Nothing came to me. I decided to fall asleep and to let the morning decide.

I showered and got myself into one of my silk pajama sets and went to bed without masturbating.

In the morning, I felt oddly calm. I didn't panic over what to wear. I didn't think about it.

I showered again and walked to my wardrobe.

I pulled out a purple lacy bra and matching panties.

After putting on a black pair of four inch heels, I looked at myself in the mirror. I looked incredible.

I wanted to the kitchen.

Ever the professional, Carmelina didn't make a single comment about my outfit, or lack thereof.

I didn't rush the process. I knew that it was my job to make the perfect breakfast for the man of the house.

The idea was still a little silly to me, but it had become more than just that.

I carried the tray to my grandfather's room and knocked on his door.

"Master Halloway," I called. "Breakfast is ready."

"Come in," he said. His voice was clear and calm. He had already been awake for a time, I realized.

I walked inside and placed the tray down on the table. I turned to face him. I felt incredible as his eyes ran down my curves and back up again.

"Would you like your coffee as well, Grandpa?" I asked.

He was still sitting on the edge of his bed with his robe on like every morning, but his hair was styled and he had shaved.

"I would," he said. "But in a moment. I believe that you may be ready for an escalation in responsibility."

My heart pounded. My knees felt weak.

"I believe so," I said.

"Come here," he said. "Use only your hand."

"Yes, Master Halloway," I said.

I walked to the bed and slid one leg up beside and around him. I felt my large breasts push against his side as I brought my lips to his ear.

"Thank you for teaching me, Grandpa," I whispered. I slid my hand under his robe and felt his chest. "Thank you for teaching me about challenge."

I lowered my hand down his chest to his stomach.

"Thank you for teaching me about structure," I whispered.

I brought my hand down lower. I let out an involuntary whimper as my hand found his enormous footlong staff.

"Thank you for teaching me about authority."

"Good girl," he said. "Now stroke."

I obeyed.

I didn't ramp up to it, but I didn't go too fast either. I simply breathed softly in his ear as my hand flew up and down his magnificent cock.

My huge, creamy tits jiggled in my perfectly tailored bra. My trim, fit frame leaned into him, signaling my devotion.

"Can I talk dirty, Grandpa?" I moaned. "Please?"

"You will speak when spoken to," he hissed.

My pussy clenched.

Then, swiftly, he brought his hand up to my hair - the hair that I had been straightening in recent days, the hair that had grown longer in three weeks than I had let it grow in my adult life - and made a fist.

He pushed my head down into his robes.

I felt a surge of excitement as I realized that he was already about to cum.

That's how badly he wanted me.

Just a few pumps of his giant cock and my stern, disciplined grandfather was going to cum.

His enormous cockhead filled my mouth and I could barely let out a moan before I felt creamy, thick cum coat my tongue.

I closed my eyes and swallowed, grateful for the incredible treat that my grandfather had allowed me to earn.

"That's it, Tessa Jean," he sighed. "That's just right. I'm so proud of you. Drink it up. Drink all of Grandpa's cum."

I had never been happier to follow an order in my entire life.