The Date

We got out of the limo. All three of us.

I finally saw our driver properly.

Can I state the obvious? Reagan was fucking hot.

She somehow encapsulated cool, dangerous and sexy, all in the same package. Like I was all of a sudden in a middle of a spy movie and this bitch was ready to interrogate me.

Oh wait. My life was a practically a spy movie these days. So this was just a logical progression, I guess.

It was very obvious I was leering at her, getting a good eyeful of every inch of her body. Reagan didn’t seem to care. Her expression didn’t change one iota. It was like she was used to men drooling over her.

I felt a tug on my arm.

“Jack! Stop staring at retard! The restaurant is this way!”

I carefully pulled Gloria’s arm off mine, and gave her a stern look.

“That’s the third time you called her a retard. Why?”

“It’s her nickname for me, sir,” Reagan spoke up. “I believe it sounds similar enough to my name, Reagan, that’s why she uses it.”

“Shut up retard! Nobody asked you anything!”

This was getting weird. I turned to Reagan.

“How long you two have known each other?”

“Six years now, sir,” she said with a painful edge in her words. I’m guessing those weren’t happy six years. It wasn’t a hard assumption to make, considering Gloria’s attitude to her right now.

“Yeah and it’s six years too much! Forget her Jack, this is our date!”

She was about to drag me again, but I slipped my arm out of her grip fast.

“So, you are the chaperone, right?” Reagan nodded. “What are you planning to do next? I mean we obviously would like some privacy.”

“I’ll stand here and keep an eye on things. You are free to talk amongst yourselves.”

Great. I hardly believe that Maria had somehow bugged this entire restaurant. I might actually get to do something more daring with Gloria.

But… Reagan on the other hand… Maybe this right now was our first, actual, app-approved meeting? Could I still get her to obey an order and start her score at zero? Something like that would go a long way with helping me in the future as well.

Yeah, and let’s be honest. Obviously I wanted to fuck her too. I mean it’s me, come on.

There was an awkward, 10 seconds of silence as I tried to come up with a humiliating order for her to follow. Gloria knew better than to grab me again, but she was huffing like a spoiled little child she was.

This was hard. Just by looking at Reagan I could tell the woman was an impenetrable wall. She would only obey the orders of her employer. And it wasn’t like I could just hire her like that. But damn, I had to try something!

“So… umm… do you have a gun?”

“Yes I do, sir.”

“Can I see it?”

“Absolutely not, sir.”

Fuck. That made no sense at all. I was grasping at straws. Something else.

“Reagan, I order you to… um… spin around and bend over. I want to see you’re not hiding any other weapons.”

“Absolutely not, sir.”

There was no change in her voice. But I could tell her hand was inching closing to her hidden pistol.

Yeah, I couldn’t make this work. I had to eat this loss.

“Well… okay then. Good,” I said awkwardly and turned towards the restaurant. Gloria was waiting for me at the entrance.

“Are you done flirting with the retard?”

“Yeah. I guess I’ll have to do with you.”

“Yeah. Awesome,” she muttered sarcastically.

It was a grandiose place. A real sense of snobbish attitude everywhere. It felt like every single waiter and patron were looking up their noses at me. I had wore a suit and everything today! I mean sure it probably was a little crumbled and dirty after the tryst with four redheads, but still…

Gloria they almost worshiped. They knew exactly who the girl was, and practically kissed her feet. Our table was smack dab in the middle of the floor. It felt like the spotlight was on us. I heard multiple whispers around us, coming from the other tables, and I definitely heard the word ‘diamanti’ multiple times.

I knew she wasn’t a celebrity or anything, but we were in the stratosphere of the ultra-rich now, and seemed like everybody knew who everybody was. Except for me. I wonder what they thought about me. Some poor schmuck that Gloria had taken for a joy ride? Then again, kudos to her, she didn’t seem to be embarrassed to be seen with me.

When the waiter asked for her order, the waiter did it with a huge smile and even complimented her adequate dress like it was some fashion masterpiece. Her smile disappeared into thin air when she turned to me and very monotonely asked what I would like to eat today.

She was a small, wrinkly, elderly woman. Not really my type. Otherwise I would have loved to add her to the list.

Then, there we were. Sitting in the same table. Waiting for our food. The other patrons’ interest in us dissipated and they returned to their dinners as well.

We were free to talk about anything now.

I think I knew how to get this party started.

“So. Has your pussy had time to heal up?”

She blushed. “Jack…”

“Because I think you are way due for another punishment.”

Suddenly, Gloria slammed her hand on the table. It was like she was trying very hard to focus on something.

“Jack… n-no. Please. Let’s talk normally, okay?”

“Sure. Let’s.” I rubbed her shin again with my foot. This time she withdrew her shapely limb.

“No, I want to talk normally. You do realize that every single conversation we’ve had is either suggestive, about work or you ordering me around?”

Well, yeah, obviously.

“Why do you think I agreed to this date? I want to talk normally,” she continued, looking determined. “In any other place or any other situation you would just start… dominating me again. And you are really fucking good at it. In here… I feel like we could actually talk. I don’t know anything about you. And you… well, you were my first one. So can we like… Just talk?”

“Talk? About what?”

“I don’t know. Just this once, no games, tell me about you. Where you come from and such.”

So… What do I do here? Just power through and dominate her?

Was she really looking to start a serious relationship?

I looked around. Yeah. This wasn’t the most ideal location for domination. Eyes everywhere. Yeah and even Reagan staring at us through the restaurant window.

Fine. Let’s please little missy. Maybe it makes things easier with her in the future.

So, I began talking. And honestly, I can’t pretend it was interesting. My life wasn’t interesting. It was about as average as can be. I told her about my early life, my school life and my family. She kept asking me more and more questions like she was interested or something. Eventually I told her how I ended up in fashion business, even though I really hated it. She found that particularly amusing.

Somehow I ended up talking for thirty minutes. I really didn’t think there was much to tell, but she kept the conversation going. And for a while, we talked like human beings. For the first time.

It was okay.

Our food arrived at some point. I had ordered just a steak, she ordered some vegetarian shit. I have to admit, possibly the best steak I had ever eaten. No wonder the rich like being rich.

Then, there were some lulls. She sort of stopped asking me questions. It took me a moment to understand why. I think she wanted me to reciprocate. Ask her about her history.

I wish I could say that I cared. But I really didn’t. I couldn’t help it.

She wasn’t my type, personality-wise. She was just a young, inexperienced girl who tried to act tough and grown-up. The only thing interesting about her was her body and her mother. And her wealth.

If this was three weeks ago, before I got the app, and I was on a date with Gloria Diamanti… I mean sure it would be an egoboost, but I couldn’t see a future with her. Not beyond sexual anyway.

She did have one thing going, though. She was full of surprises. There were some things I still didn’t quite get about her.

But I had to ask something about her. Might as well make it useful.

“How is life in the Diamanti house? Your mom seems like a… very protective woman.”

Gloria’s eyes rolled in her head.

“The bitch is a nightmare. She has made my life a living Hell. I mean Jesus Christ, she should look at my birth certificate for once and see how old I am! I don’t need her coddling me.”

Well, I could easily agree with all of that.

There was a question I had been wondering about their relationship for quite some time now… Maybe it was the right time to bring this up?

“Well, sometimes bad girls need to be set straight. She ever spanked you?”

That got her quiet, and then looking a little annoyed.

“I don’t want to talk about her anymore,” she stated.

Oh yeah. I was hitting on something. And I think I saw a way out of this conversation.

“She did spank you, didn’t she? I can already see you, bending over her knees-“

“Stop it.”

“ready to receive a hairbrush right on your little tushy.“

“Please. Stop.”

“It wasn’t quite enough, though was it? At some point she even stopped doing, right? You had grown too old.”

“what’s… wrong with you…”

I was getting somewhere. Her face was reddening again.

“You wished for those days when she grabbed you, bent you over and left some red, stinging prints on your ass, didn’t you? Treated you like the bad girl that you were?”

She didn’t say anything, just breathed a bit harder.

“A woman’s hand wouldn’t be enough now. And it felt weird asking your mom to do that anymore. You needed a strong, powerful father-figure to provide some justice.”

“jack…”

“I bet one of the hunks your mom dated seemed just like the right type. And when you asked him…”

“how do you…”

“He was disgusted. And you grew more and more ashamed of your kink until one guy at your office…”

She let out a small moan.

“One normal looking guy just took you downstairs and delivered the sweet justice you’d been waiting for years. Left your ass stinging for hours upon hours.”

She was biting her lip. I couldn’t se her hands, but she was gyrating like she was rubbing her pussy underneath the table.

“The father-figure you’d been waiting for years. The one who wasn’t disgusted by your… perversions.”

She swallowed hard and kept gyrating harder.

“Well here I am, missy. And I’m tired of playing around. Go to the bathroom and wait for me.”

She got up surprisingly fast. She shared one questioning look at me, and almost sprinted towards the bathrooms. (GLORIA: +2SP) (+49SP)

That’s it? Only two points? I wasn’t making great progress yet. So far everything had happened almost as Gloria had wished. Getting more points out someone who wanted to be humiliated was extra hard.

I waited for a minute. Better not make this too suspicious-looking. Like I was going straight after her.

Reagan had disappeared somewhere. She wasn’t behind the window anymore.

Perhaps the coast was clear?

I got up. It was time to **** a spoiled little bitch again.

Then I felt her hand on my shoulder.

At some point Reagan had sneaked up behind me.