Over the years I've attempted to write pieces of this story. Every time, it's been about a single experience that was floating through my memory at the time. While writing about a specific experience was easy, it always lacked the depth, context, and erotic foundation of the overall relationship. This story is my attempt to pull it all together. All of this is true and actually happened, although I have changed some of the personal details for discretion.
I first met Jan at a project kickoff meeting between our two companies. The customer had been facing a unique challenge and approached both companies about working together to deliver a solution. What initially caught my attention was the skill and ability Jan displayed at pulling both teams together and laying out a logical structure for the project group. What also caught my attention was how attractive she was.
Jan was in her mid-30s, around 5'7" tall and if I had to guess, about 130 lbs. She had dark, shoulder-length hair, green eyes, thin, red lips, and a warm smile. While she had the curves of a woman in her 30s, her body was clearly toned and in shape. She was wearing a skirt the first day we met and I remember staring at her incredibly shapely legs. She also wore a white, button-down blouse that was conservative, but highlighted full, round breasts that I guessed were 36D, making them almost out of proportion with the rest of her body.
That evening, we all went out to dinner as a group. Jan and I sat across from each other in a booth, along with a couple of other colleagues and chatted throughout dinner. We were still deep in conversation when dinner ended and decided to walk down the street to a bar and continue our conversation. I think it was nearly midnight when we finally headed back to our hotels.
Over the course of the evening, I learned that Jan was recently separated and had two daughters, both in their mid-teens. She told me that she and her husband had grown apart and the tension between them finally got to the point where they realized it was hurting their daughters and they needed to separate for everyone's well-being. The good news was that her mother lived close by and was able to look after the girls whenever she was traveling for work, which was fairly often. My situation wasn't all that different except that I had been divorced for a little over a year and my kids lived with their mother, who had moved back home to Georgia.
After the second day of the kickoff, my company sponsored a social hour on the patio of our hotel. I ended up sitting next to Jan and we continued our easy conversation. I'm not sure what caused me to be so forward, but I slid my leg over until it was touching hers. Jan looked directly at me and raised her eyebrows, but didn't pull her leg away. After a minute or so, I slowly raised and lowered my heel, rubbing my leg against hers. Jan's eyes bore into mine and her lips curved into the very slightest of smiles, as she mimicked the gesture.
We continued to play "footsie" on and off over the course of the next hour, neither of us letting on as we chatted casually around the table. When the social hour ended and we got up, I felt Jan's hand graze discretely across my lower back.
"What are you doing for dinner," Jan asked?
"No plans yet. You?"
"No plans either. Have anything in mind?"
"How do you feel about Italian? I know this great little place that's been around for decades. It's about a fifteen-minute walk if you're up for a little exercise."
"I think a walk would be great after a full day sitting in meetings."
"How about I meet you in the lobby of your hotel around 6:45?"
"Perfect."
I headed up to my room and grabbed a shower, unsure of what to expect for the evening, but wanted to be prepared for whatever happened. I dressed in jeans and a black, button down shirt, and headed to Jan's hotel.
Less than a minute after arriving, the elevator doors opened and Jan stepped out. She was also dressed casually and in a way that made us both laugh since we looked like we had planned our outfits...jeans, a black silk blouse and black open toed heels. I did notice though that one additional button was open on her blouse compared with earlier in the day.
Over the course of the next two and a half hours, we talked, laughed, enjoyed a lovely dinner, and got to know each other a lot better. None of the conversation was overtly sexual, although we were open about our interest in each other.
"Can I ask you a personal question?"
"Sure."
"Why did you begin rubbing your leg against mine this afternoon at the social?"
"I hope I didn't offend you?"
"Not at all. I was flattered, but...well...I'm usually not the person guys flirt with. There are plenty of younger, sexy girls on the team that always seem to get extra attention."
"I did it because I wanted to flirt with you. You're incredibly smart, clearly a great boss and manager who your team respects, you're fun, fascinating to talk with, and...well...I think you're incredibly attractive and sexy."
Jan's eyes opened wide and a bright smile spread across her face at the string of compliments. "That's one of the loveliest compliments anyone has ever given me. And I can say exactly the same about you."
She paused and bit her lip, clearly unsure of whether to say what she was thinking. We had each had two gin and tonics at the social, a third when we got to the restaurant, and now were nearing the end of a bottle of wine. I was feeling the effects and was sure she was also. Whether it was the drinks or her just being turned on and wanting to tell me, I couldn't be sure, but she finally said, "The touch of your leg really turned me on and I was nervous when we got up from the table that...someone might notice how turned on I was."
"Notice? How so?"
Jan paused again and looked down at the table, then finally back up at me. "I hate underwear and never wear any. I haven't since I was a teen. I hated the way they would shift around or cause panty lines. And...well...the openness felt good. It's never been a problem at work until today when you had me so turned on. No ones' flirted with me in a long time."
"Ah...that definitely makes sense," I said with a smile. "I'm glad you enjoyed the flirting."
"Oh, I definitely enjoyed it," Jan said before thinking about what she had just admitted, turning instantly red. Not only that, I was beginning to see the outline of her nipples, even through her bra. Wow, her body really responded to her emotions.
"So, I guess when you say underwear, you only mean panties since you've been wearing a bra both days."
"I definitely couldn't get away without one, at least at work or when I'm out. It would be way too obvious. But since I'm being so totally open, which is totally shocking me, I'll just say I never wear one at home or if I can get away with it when I go out."
"Why do you say your openness is shocking you?"
