Time seemed to stand still ever since I’d asked Tiffany on a date yesterday. I still did not understand why it took so much work to get her to say yes. Was I not her type? Was she just playing hard to get? I would have to ask some questions tonight in a roundabout way to get to know her better.

I really wanted to know why she was so damn insecure. It completely baffled me that she had such low self-esteem but was completely gorgeous. I wanted to help her see her beauty, inside and out.

To be honest, the fact that she played a little hard to get made me want her even more. I hadn’t tried so hard for a date before in my entire life. The bigger the challenge, the bigger the reward, right?

It was nearly noon and I hadn’t seen her all morning. I usually would run into her by the coffee machine, but not today. I hoped she hadn’t called in sick that day. I decided to try to casually stop by her office.

On the way there, I ran into Nikki.

“Hot date tonight, huh?” She winked at me. I nodded. Nikki was the last person I wanted to talk to about tonight’s date. I didn’t respond to her, but she didn’t care. She continued to talk.

“Just be careful with her, Cayden,” she said. “I’m not sure of your intentions, but she’s a good soul with a shattered past.”

Shattered past? I wanted to ask questions, but as we reached the office, Tiffany popped out.

“Hey, Tiffany,” Nikki said. “We were just talking about you!”

Tiffany blushed.

“Nothing bad,” I reassured her with a smile. “Are we still good with 7:30 tonight?”

She wrinkled her nose and looked away.

“You guys are still good,” Nikki answered for her, slipping inside of the office.

“Yes, we are still on,” Tiffany finally responded. I sensed a bit of hesitancy in her voice, but I let it slide. I did not want to give her an opportunity to back out of this date.

I pulled up in front of her house at 7:30 on the dot. She must have been waiting by the door, because she opened it almost immediately. She was beautiful. As she approached my car, I checked her out from head to toe. Her dark hair was wavy, and she had styled it half up and half down. Her makeup was done perfectly with a bold, sexy red lipstick. While her hair and makeup were great, neither of them matched her outfit.

She wore a short black dress with tie-up heels. The dress wrapped around her curves and put her large breasts on display. The dress was short and for a minute, I wondered what kind of underwear she had on underneath.

I jumped out of my car and opened the door for her.

“Good evening,” I said with a smirk. “My name is Cayden, and I will be your chauffer for the evening.”

She laughed as she entered my convertible Mustang.

“Thank you,” she said.

I closed her door and walked back to my side.

“You look absolutely stunning,” I told her as I got in the car.

“Thank you,” she said again.

I drove us toward a popular restaurant in Little Havana, the warm, Miami breeze in our faces. It was hard to have a conversation with the top down, so I would have to wait until dinner to start asking questions.

As we entered the restaurant, I noticed an older man check Tiffany out and lick his lips. I was instantly protective and wanted to punch the pervert, but Tiffany did not notice him. We sat down at a table.

“I am so glad that you agreed to go out with me tonight,” I said. “I have to admit, I was attracted to you the minute I met you.”

She smiled. The worry that I’d come on too strong went away. I figured there was one of two ways I could act. I could either be more aggressive, or more timid. Since she was shy, I didn’t think two timid people would work. I would need to be the one to push things along, in a completely consensual way, of course.

After we ordered, I began to ask her questions to help open her up. While I wanted to bombard her with questions and learn everything I could about her, I refrained and took it slow.

“Have you lived in Miami your entire life?” I asked.

She nodded, putting down her wine glass.

“I have,” she responded. “I was born here, raised here, and can’t imagine living anywhere else but here.”

“I don’t blame you. I moved here from New York when I was in high school, and there hasn’t been a single day that I have regretted it. I went up last year to see some friends, and there was so much snow. If I never had to see snow again, I would be the happiest man in the world.”

She laughed, and my heart flittered around.

“I’m twenty-five and have never seen snow in real life. It’s only snowed one time in Miami. It was January 1977. My dad told me about it and said that some people thought it was the end of the world.”

“I would imagine!” I said. “Did you go to school around here, too?”

She nodded.

“I graduated in 2015 from the University of Miami with my journalism degree. It’s actually funny that you mention you’re from New York. My dream is to be a reporter for the New York Times.”

Her green eyes sparkled with excitement. It was the first time that I’d seen her face without the sadness it usually held. She looked like a different woman. For once, she didn’t seem burdened by trying to fit into a mold or being an outcast. I liked this side of her.

“You’re kidding me! My dream growing up was to be a reporter for the New York Times. I would always go into the city and dream about working in the offices, being the top dog at the Times.”

“So why did you leave New York, then?” she asked. It was a fair question.

“My dad got a job down here. Plus, The Times is a tough gig,” I said. “I tried but couldn’t even get in there at the very bottom. I found this job shortly after college and never looked back.”

I watched as her face fell with disappointment.

“Did I say something wrong?” I asked. The mood had noticeably changed.

“No,” she said. “It’s just… if you can’t get into The Times, I definitely can’t get in there. Just another one of my stupid dreams, I guess.”

Just like that, the insecurity was back. I wish there was something that I could do to help her realize what a talented woman she was. I would just need to continue to work on it.

“It’s not a stupid dream,” I told her. “Believe me, your fact checking gig is just a stepping stone to something bigger and better. Trust me. If there is ever a place for advancement, I’m recommending you.”

She smiled and wiped a tendril of hair from her face.

“That’s nice, but you don’t even know me.”

“I know your work,” I responded. “I know that you’re one of the best fact checkers that I have ever worked with. I know that you always do a great job and you’re the one I prefer to work with. I know that your work is thorough and timely. When you have traits like that, you carry them with you to any job.”

She shrugged.

“Well, thank you,” she replied. “I really do appreciate you having confidence in my abilities. I have been lacking in that area for quite a while.”

Before she could continue to speak, or I could ask more questions, the waiter appeared with our dinner.

Dammit, I cursed him. It was the first time I was irritated by speedy service. I wanted to see if she would say more, but the conversation turned to our Cuban food.

“I should probably tell you something before we go any further,” I said after the food talk died down. I wanted to tell Tiffany about Austin. If she didn’t want to date a single dad, I would need to know that before I fell for her. She looked at me nervously.

“I have a son,” I admitted. She smiled and let out a sigh of relief.

“Thank God,” she laughed. “I thought you were going to tell me this whole dinner was some office joke! A son, I can deal with. What’s his name?”

“His name is Austin,” I said. “He’s four, and he’s my whole world. I just wanted to let you know upfront.”

“Thank you. I appreciate that. Do you have a picture of him?”

I retrieved my phone. I’d thousands of pictures of Austin. I picked my recent favorite and showed Tiffany. She smiled.

“He’s so cute,” she said. “He looks like you.”

There was an awkward silence and I wondered if she was thinking about Austin’s mom. I hoped she wouldn’t ask about her, because that was one topic that I didn’t feel comfortable discussing right now. The dreaded “C” word would have ruined the whole night. Luckily, I was able to quickly switch the subject.

The rest of dinner went well, but it never got back to that personal level like it had earlier in the night. I took it as a win, though. She was finally opening up to me. Slowly, but surely. Hopefully there would be more time in the future to ask questions and get answers.

Since it was a work night, I decided to take it easy and not extend the evening. Not that I wanted it to end. I could have stayed at dinner with her all night or taken her out for more drinks, but I did not want to press my luck.

After we arrived back at her place, I parked the car on the side of the street and walked around to open her door.

Damn, you’re a gentleman, I thought to myself as I opened her car door.

“Can I walk you to your door?” I asked her. She nodded with a smile. I reached for her hand. It took her a second to extend her hand and place it into mine.

Baby steps, I thought. I could do baby steps if it meant they were leading somewhere.

“Do you live here alone?” I asked. She shook her head.

“I live here with my best friend, Mandy,” she explained. “But, she’s a nurse and works nights, so she’s not here right now. We work different schedules, but it’s basically like I live by myself most of the time.”

“A little bit of both worlds, huh? It’s like living alone but paying half the rent. Not a bad way to live.”

She giggled as we reached her door. She looked gorgeous, even under her yellow porch light.

“Thank you for tonight, Cayden,” she said. Her hand was on the doorknob, ready to open it and go inside. I’d seconds to make my move.

Instinctively, I dropped her hand and put one of my hands on each side of her waist. I pulled her closer to me and our lips met. Just as I imagined, her lips were soft and luscious. She kissed me passionately as my tongue slowly darted in and out of her mouth. Her breasts pushed up against my chest. She wasn’t wearing a bra, so I could feel her hard nipples too.

I wanted to reach down and grab her breasts, but I resisted. We were on her front porch. It was neither the time, nor the place. I’d to shut this down before I got in trouble.

I pulled away and she wiped her mouth with a grin.

“That was fucking amazing,” she said. It was the first time that I heard her swear and it turned me on. My cock began to swell even more in my dress pants. I noticed her look down at my crotch for an instant. She had to have seen my cock busting through my pants.

Her eyes looked hungry and I knew she wanted more, as well. But for both of our sakes, I needed to take this slow.

“Thank you for finally saying yes,” I said, taking a step back. “We should definitely do this again.”

She nodded, biting her bottom lip. I desperately wanted to take her into the empty apartment, but I refrained. She had just agreed to another date. We could take this further another day. It was hard to tell this to my raging hard-on, but I’d to play it cool. Tiffany was someone that I would have to take it slow with, but I needed one more taste.

I reached over to her, kissing her for a second time. I moved my hand by her cheek, pulling her as close as possible. I wanted to feel her body completely against mine. My cock was rock hard now. She must have felt it through my pants.

We said goodbye and she walked into her apartment alone. I walked back to my car, thoughts of a naked Tiffany dancing through my head. Her breasts had felt so good pressed up against me. I wanted to know how they felt in my hands. I wanted to know how her hard nipples would feel in my mouth. I would definitely have to go home and take matters into my own hands.