Club Endless Fantasy

Ian

I got the best night of sleep that I had gotten in years and woke up feeling rather refreshed—partially because of what I did before I went to sleep and partially because I had Elly’s beautiful smile in my thoughts all night long. The first thing I did was reach for my phone and read through our conversation. I didn’t need a reminder to remember what we talked about, but it was still nice to read the exchange. By the time I finished, my cock was hard, and I was thinking about turning our conversation into reality.

I’m so tempted, but we should wait before we take the next step in our relationship. It needs time to flourish first.

Somewhere in the midst of flirting, teasing, and talking dirty to each other, Elly and I made plans for a date. I needed to figure out where I was going to take her and make plans. I fixed a pot of coffee, pulled out my phone, and started doing a little research. It had been a long time since I planned an actual date, so I was rusty on current events that didn’t involve global politics or business—the former was my grandfather’s specialty, and the latter was mine. I found a few things that were interesting and jotted them down.

Hopefully, Elly is in the mood for a night on the town.

It was Sunday, which was when I normally called my parents, so I decided to do that before I contacted Elly to discuss our date. My mother answered the phone, and we talked for a little while before she handed the phone to my father. Both of them were enjoying the weather in Florida but looking forward to coming home for Christmas. It wasn’t a long conversation, but it was nice to talk to them—and even better to hear that they were doing well.

The year Alexander Software launched its first successful app changed my life. I went from living in an apartment in what was essentially the ghetto to being able to afford a house. Two years later, I had enough money in the bank to buy any house in the state. I offered to share that wealth with my family because they were the ones that were always there for me when times were tough—both emotionally and financially.

My grandparents on my mother’s side lived out west and were doing pretty well for themselves, so they didn’t really need anything from me. My grandparent’s on my father’s side had been poor most of their lives, and while they had each other, they finally agreed to let me set them up in a nice apartment in the city. My sister wasn’t one for charity, but she said it was okay if I spoiled her kids—I already planned to do that, whether I had her permission or not. My parents—they were a lot more open to my offer. They had always dreamed of living somewhere warmer and traveling the world after they retired. I was able to provide that for them, which made me feel like everything that brought me to that point was worth it in some capacity, even if I didn’t have the kind of love in my life that they had.

Maybe I’ve got another shot at that with Elly. It’s too soon to be thinking about forever, but I can’t ignore the way that I feel about her…

Elly and I talked in the afternoon, and she agreed to let me pick her up for our date. I wasn’t in the mood to drive, and there was a chance that I wouldn’t be comfortable behind the wheel by the time our date was over, so I requested a car. Elly lived in a pretty nice apartment building. I was surprised that she was able to afford it if she was just getting started in advertising. I assumed there was some sort of affiliation with her company that made it possible since I knew what real estate in the area went for. I tried that once with Alexander Software, but we weren’t able to make it work once the company started growing.

Okay, this is her apartment…

I knocked on the door and waited. A couple of seconds later, I heard Elly’s voice on the other side. I couldn’t make out every word that she said, but I pieced together enough to understand that she was still getting ready. I glanced at my watch, and we still had plenty of time, so I didn’t stress about her tardiness. One thing I learned from my parents was that there was no reason to sweat the small stuff—it was just wasted emotions that didn’t change anything.

“Sorry.” Elly opened her door. “I lost one of my shoes…”

“It’s fine.” I smiled and pulled her close. “I would have waited forever if that’s what it took for me to get another taste of your gorgeous lips.”

I crushed Elly’s lips with a passionate kiss that instantly reignite the fire that burned between us before I was forced to pull away the night before. I didn’t care. I had been thinking about them since our last kiss, so I was willing to take another risk—and gamble on my ability to break the seal that formed before we ended up inside her apartment. It only took me a second to realize that my plans for the evening didn’t matter as much as having Elly in my arms, but the voice in the back of my mind told me not to let it go that far.

“You can say hello to me like that anytime you want.” Elly looked up at me and grinned as soon as I leaned back from our kiss.

“I just might…” I let my hands slide down to her hips. “You look beautiful.”

“Are you admiring my dress or wondering how it will look on the floor later tonight?” Her grin got wider.

“I already told you that we needed to wait…” I exhaled sharply, and despite my hesitation, I pictured exactly what she said.

“What if I don’t want to wait?” She leaned closer. “I want to be on Santa’s naughty list tonight.”

“Let’s talk about that later.” I looked down and sighed. “We’ve got somewhere to be right now.”

“Okay, let me grab my coat.” She disappeared into her apartment and emerged a few seconds later.

“All set?” I took her hand.

“Yep! Where are you taking me anyway?” She looked over at me as we walked towards the elevator.

“A wine tasting.” I hit the button that would take us to the bottom floor. “Well, technically it’s multiple wine tastings—it’s an event that’s being sponsored by several of the biggest vineyards in the state.”

“Well now I know I’m going to end up on the naughty list.” Elly giggled and kissed me as soon as we stepped into the elevator.

Elly and I kissed until the elevator doors opened on the bottom floor. An older couple got quite a shock when they tried to enter the elevator before we had a chance to exit. We managed to keep a few feet between our lips until we were in the backseat of the car, and then the heat really got turned up. I had to raise the barrier between the front and back of the car so that the driver didn’t get a show he would be thinking about when he got home that evening. Elly’s hands moved along my body and I explored her curves with mine. My cock was throbbing and telling me that waiting was lunacy—I had a gorgeous virgin in my arms that didn’t want to be one by the end of the night.

“You’re making this so difficult…” I exhaled sharply and traced the skin at the bottom of her dress.

I bet she is wearing the shortest one she owns—in the middle of winter.

“You teased me too.” Her eyes flickered with excitement. “Don’t act like I’m the only one that was misbehaving last night…”