April 2018

After a few years with my last employer, we merged with another company and started holding a once a year conference for everyone in my department across our organization (we were a nation company). The meetings were held in Minneapolis near our company HQ and were a fun way to meet with vendors and work associates from all different divisions across the country. I especially enjoyed them as I was from the companies smallest division, didn't really have a local counterpart in role, and primarily worked with old white men that were boring.

My first trip out to MN I really hit it off with Kelly, she was in the same work role as myself but working out of one of our West divisions. I'd seen her picture before on teams and been involved in conference calls with her but we'd never met in person. Her and the rest of her team from the west were a fun breath of fresh air. Not sure I would say Kelly was overly flirty, at least not forwardly but she was very friendly to me and we buddied up for several dinners and activities while at the event. This first trip went quickly and we parted ways but it had been fun and great to make a few new friend on the trip, Kelly and I would occasionally chat offline during all team calls going forward but nothing more than friendly hello's and catching up on what was going on in our work lives mostly.

The following year I was excited to see her smiling face when I got to the expo - she was in line to check into the resort we were staying at when I arrived to do the same. Kelly was a few years older than myself, late 30's (I was 34 at the time), and married with no children. Although she didn't have kids, "hot mom next door" would be a simple and fitting physical description for her. Kelly was attractive but somewhat unassuming - she wore little makeup, kind eyes and a sweet smile, medium length straight brown hair, and she looked like she belonged in the business casual I always saw her in - a skirt or dress slacks with a cute blouse. Occasionally she'd show off a little of her firm and fit figure, she was a competitive runner and looked the part.

That evening we caught up at the welcome reception, telling stories of how work had been going in our regions and what we'd each been up to personally. The resort we held the event at had a bowling alley and casino which was conducive to all our associates hanging out and being social. Kelly and I buddied up again, playing on the same bowling team, grabbing drinks with the same group, and making dinner plans with each other. Kelly did a little more flirt this trip, as did I - seemingly innocent touching and nudging of each other, sitting closely at dinner, and one night jokingly referring to me as her "work husband" for the week.

These expos always go fast and next thing I knew it was the last night of the trip. A dozen or so of us went to the casino after dinner to do a little gambling and have some drinks. Kelly and I were standing behind the group, chatting and playfully teasing each other as the rest of the group played video roulette or cheered on the ones who were.
Kelly said to me "I'm going to walk over there for a minute to check my phone and use the bathroom, want to walk with me and hold my drink for a minute?" "Sure" I replied as I grabbed her drink and followed along. After a minute in the restroom Kelly emerged and walked back over to me. "You better not have put anything in my drink" she joked as she reached out her hand. Without hesitation I replied "I'd want you completely coherent for what I'd do to you, you definitely wouldn't forget it" I replied with a wink. She went speechless for a second, blushing a little and gathering herself. Possibly still a little flustered but being very cute, she quietly said "you definitely have my attention" As she leaned her face close to mine and bit her bottom lip - almost daring me to kiss her. I glanced towards our group to ensure no one was looking, they weren't and I leaned into her as well and gave her a kiss, a short peck on the lips at first followed by a longer, lingering kiss the second time.

We both sort of froze for a second, just looking at each other in silence. She had a gaze of pleasure, excitement and surprise - I could tell this wasn't something she had done often if ever. "Do you want to come up to my room?" I asked. She stared, took a deep breath and paused for a moment. "I do" she whispered as she let her breathe out. In tandem we both looked over our shoulders at the group again to make sure we weren't being watched, we weren't. "I'm in room 1734, do you think anyone will notice if we sneak off?" I asked. "They won't. I'll give you a head start, after you get on the elevator I'll walk that way and do the same, I just don't want anyone to see us leaving or going into your room together. Meet you there in 2 minutes?" She asked "That's perfect, I'll see you up there" I said as I gave her a smile and walked to the elevator.