This is the second part of a multi-part story. The first five parts are the initial book. I am adding parts as things develop with these characters. Note that although this story is in the Lesbian Sex category, it is a straight, mature romance, which is part of the larger arc of the story.
Simon Douglas
"Eileen? Eileen Neally." She was walking for lunch on Main Street in White Plains when she turned to see Simon Douglas rushing up to her. "Eileen? I thought that was you. How are you?"
Simon and Eileen had worked together in her small bank until he left for a job in New York City about five years earlier and since then, she'd heard, he'd done well for himself, ending up with a small hedge fund with its office along the water in Greenwich.
"Simon. My goodness. How long has it been? Four, five years?"
"From when I last saw you? Five years, three months, six days and"—a glance at his watch— "13 hours, eight minutes, and...32 seconds. Far too long." It was a completely arbitrary figure but he said it with such flair that she almost believed it, down to the second. He was a charmer this Simon. A solid five-ten with the build of a rugby player and thick, short hair, a bit weather-beaten; it was clear that whatever else might have happened in his life he had not given up on staying in shape.
"Such a tease. What are you doing here?"
"A meeting with our bankruptcy counsel. We're looking to get involved in the auction of assets of a firm in Chapter 11 that filed up here. I confess I hoped I'd see you. And I did."
It was mid-September 2017. Were it a year earlier, Eileen would have left it with a curt nice-to-see-you-again/keep-in-touch but she was different now. After her husband, Michael, died in 2010, she threw herself into her work and her daughter. She had neither the time nor the inclination to do anything for herself. Now her daughter Kerry was living at home while going to law school in the City and through Suzanne, Kerry's girlfriend, Eileen met other women her age and started enjoying being social again, emerging from her self-imposed shell.
So when Simon asked if they could go to lunch, she readily agreed and in ten minutes they were sitting in a small Italian place on quiet side street near the courthouses and she was sipping on her water and breaking off a piece of bread.
She had not been alone with a man like this since before her husband died. It was nice. They each ordered, she limiting herself to a Caesar salad, he to sole, and exchanged gossip about shared current and former workmates and she discovered that she was having a good time, a very good time. And now when she said how nice it was to have seen him and how they should keep in touch she said it with sincerity.
Kerry was at the house in a village just north of the City when Eileen came through the door and, as happened a couple of times a week, dinner was ready for her after she washed up and changed. The two fell into their typical relaxed conversation until Eileen dropped the bombshell that she'd "had a lunch with a former colleague." As soon as Kerry understood that the former colleague was a man, her interest in this lunch rose exponentially. Her Mom told of his calling to her on Main Street, of how attractive he "still is," and how nice it was to just sit down in a quiet restaurant with a man with no pretenses or expectations and how much she enjoyed it.
"Mom, was this a date?"
"Honey, it definitely was
not
. Just—"
Eileen was not so sure. How was it not a date? The only thing not-a-date about it was the happenstance of running into him on Main Street.
"He just happened to see you come out of the office where he once worked and happened to take you to lunch?" This was Kelly, interrupting Eileen's thoughts, which now veered to wondering whether he had been waiting for her. Things she hadn't noticed then she noticed now. Whether his meeting ended long before he let on and he loitered about until she showed up. Was there even a meeting? What if he was stalking her? Why had he emphasized his inability to find anyone after his divorce? That he was now in a position at the fund where he did not have to travel as much as he had, travel he had long since tired of?
Now Kerry interrupted
this
train of thought. "Are you going to see him again?"
"I doubt it. Although I wouldn't be unhappy if he asked." and Kerry simply said, "Well then, let's hope he does" before clearing away the plates. Kerry in fact was far from calm in all of this, her thoughts quickly ratcheting up for her Mom's future, but it was best to keep a low profile.
And he did ask. After a decent interval—two days—he called her while she sat in her office at mid-afternoon on Thursday.
"Eileen. It's Simon. Look, there's a thing here in Greenwich on Saturday night. I wondered if you'd like to accompany me."
"A 'thing.' Simon you are such a wordsmith."
"It's a gallery opening," he confessed, "I get these invitations all the time but almost never go. I don't want you to think I'm some kind of art connoisseur. It's really just a convenient excuse for me to ask you to go out with me."
"Always the charmer. Let me see how free my calendar is." And then after a decent interval—two seconds—she said, "I'd love to." and when he offered to come down to pick her up, she insisted that she could drive herself the half-hour up, and back, and so they met outside the gallery at 7:30 on Saturday. The exhibit was a bit too modern for the tastes of either of them, but it was fun to stop in front of each and ask each other, in turns, "what do
you
think it is?"
There was no question. This was a date, the gallery-visit followed by dinner, and Eileen enjoyed it and enjoyed each of the ones that followed. She felt comfortable enough that on the third or fourth date, while having dinner in Greenwich, the one that led to their first kiss, she told him of the unhappiness of her marriage, especially towards its end, of her becoming dependent on alcohol to try to bridge a gap to happiness, and of having stopped drinking after her husband died.
Simon had by then told Eileen many of his own stories, unknown to her when they worked together. He had married young and they both realized the mistake before kids came along. He'd been on a roller coaster with women forever, stretches of ups and stretches of downs, near-engagements and narrow-escapes. He was tired of it. The efforts he put into work had long since paid off for him and as one of the firm's old-guard—at the ripe old age of 46—he had easily slipped into the elder-statesman role at the fund and leaving it to younger people to do what he, when