Katie (Remastered)
I met Jenna when I was 30. She was four years older than me and had been on her own since she was 18. A college guy had knocked her up. She wanted the kid, he didn't. Unsurprisingly, he disappeared.
As for me, I was single. I'd come out of a relationship three years before and was still recovering. Family gatherings, I discovered, are awkward when your former fiancΓ© is married to your brother.
I coped with the anger, hurt and betrayal by dating good looking women who meant nothing to me. My theory was that you can't get hurt if you don't care. I know, that kind of made me an asshole, but I'll be damned if it didn't work.
The wife of a co-worker decided that I was her special project. She was going to save me from myself. Oh yeah, The office thought that it was fucking hilarious. Me? Not so much.
I repeatedly rebuffed her subtle matchmaking attempts. Finally, she thrust a name and number into my hand saying, "Call her." I started to give her my standard brush off, but she was fiercely insistent.
We were with the gang and quite drunk. I shrugged and said, "All right, sure." I took the number. She gave me a menacing look until I raised my hands in submission. "All right, I'll call her. You have my word." We then did a shot and the rest of the night was a blur.
I called the chick a few days later. She was cool. The chat was good, so I asked her out. I became a bit nervous when I realized that I actually liked this woman.
I decided that I would do it right. This was going to be the perfect date. I meticulously planned everything. I felt confident. Nothing could possibly go wrong.
About that... So yeah, the date was an unmitigated disaster. I was late, the restaurant didn't have my reservation and I felt uncomfortable. I was wearing an expensive suit that made me feel out of place. Hell, it even felt like I'd cinched my tie too tight. I couldn't figure out what the fuck was wrong with me.
It had nothing to do with Jenna; she was great. The woman is absolutely beautiful with dark blonde hair and bright blue eyes. Jenna was nothing but class. She was warm, elegant and composed the whole time.
In retrospect, I suspect I fell apart because she was too good for me. Jenna was impressive and a bit intimidating. While raising her daughter, she'd earned her bachelor's and master's degrees. Oh, and she'd worked full time during her studies.
This was new territory for me. I was used to being the most impressive guy in the room. I was fit, I'd gone to a fancy school and was the golden boy in my firm. Whenever there was a problem, they called me to fix it. I was going places. Everyone said that I was going to be the boss someday, including me.
But compared to Jenna? I was nothing.
When I looked into her eyes, I felt like an awkward teen. I blushed and made mundane comments that were neither interesting nor profound. I'd been making a fool of myself. To cap it off, I spilled a glass of red wine. I was mortified as it splashed into Jenna's lap, staining her lovely lavender dress.
At the end of the night, I didn't even try to give her a kiss. I walked her to the door and started to say, "Look, I'm really sorry-"
But Jenna cut me off. "Shut up. Kiss me," she whispered. I'm not stupid. I obeyed. I expected it to be a soft, sweet kiss. I was correct at first. But then it slowly built with passion and desire. We became primal, as if we were starved for one another.
We continued, indifferent to the fact we were standing on her front porch. She felt me get hard and whispered, "Oh my." I pulled her even closer. I'd never wanted anyone more than I wanted her.
We heard a car door slam behind us. We broke apart and straightened ourselves just as a girl rushed by. "Gross," she said with disgust. The girl passed behind me and disappeared into the house.
Jenna blushed. "That's my daughter, Katie," she said. "I'm going to catch an earful." We both laughed. All I'd seen was the girl's blonde hair. Jenna quietly explained that she was 16 and hated it when Jenna went on a date. "Why can't she be like other teens and break curfew?" Jenna asked in a conspiratorial whisper. "I might get laid more!"
"Kids..." I said, laughing a bit as I awkwardly tried to make my hardon less obvious.
Jenna caught me mid-adjustment and gave me a wicked smile. "It looks like I won't be the only one left frustrated tonight." I burst out laughing; both of us did. The awkwardness evaporated. Jenna looked me in the eye and said, "I'm going to be frank: The date sucked and you ruined my dress."
"I'll buy you a new one-" She raised her hand, so I shut up. "On the other hand, I was told you were an arrogant prick. But you're not. You're something else."
I needed to have a talk with the office matchmaker. "Oh yeah?" I asked.
"Yeah," Jenna replied. "You're a bit of a dork and kind of cute."
With uncertainty, I said, "Thank you?" She was telling me to hit the bricks. I deserved it. Jenna had been looking to score and it wasn't going to happen. Better luck next time, right?
"You're welcome," Jenna said. She then surprised me by asking, "When are you going to ask me out again?"
"Pardon?" I said. I caught myself and asked, "Can I take you on another date? Maybe next Friday?"
"No. Saturday," Jenna countered. I already had plans for Saturday, but fuck it. I was cancelling. "This time, don't try so hard. Relax. I like you and I can tell that you like me," her hand brushed against my aching cock.
"I really appreciate that-," I started to say. But then, I realized I had to step up. I needed to be the man. With confidence, I told her, "Wear some jeans. We'll go to a bar I know. We'll play some pool."
"I'm not good at pool," Jenna warned me.