If I decided to really start at the beginning of this story, it started with a handshake β not with her but with her husband Greg. I had been called for an interview by his search firm and when I was introduced, and we shook hands, I knew I was going to work with him. It was visceral. Two hours later I was offered the VP position. I started the following week. This is a true story and its mine.
When I arrived for my first day I was pleasantly surprised to be greeted by the office staff and the boss's wife. She was about 45 or so, 5'4" with a well maintained body, proportional breasts, trim figure, cute little ass, shapely legs and a bright smile. To say the least she was extremely attractive.
Over the next couple of weeks as I got settled into the new position, I had the opportunity to spend a great deal of time with her. Let's call her Gail for these purposes. We shared some physically close moments that, when I reflect backwards on it, were probably uncomfortable for both if us β we both recognized the attraction and the sexual tension.
Me? I'm 46 years old, about 6 foot tall and I try to stay in shape with a weekly workout and regular golf. Some months I need to lay off the big meals and spend more time at the gym. I had been divorced from my wife for about three years and had decided I needed a personal life change. So I quit my job and moved about as far away as possible to someplace where I knew no one. After three months of searching I had finally landed a job.
So back to Gail. Our first real physical connection was actually in public at a Memorial Day party at their home. I was greeted with a warm and firm hug, which I reciprocated. Her body was completely against mine which allowed me the opportunity to feel the outcome of her regular workouts and the subtleness of the rest. I reacted like any other red-blooded horny America guy. I was hardening almost immediately and backed away to avoid any embarrassment. She looked up to my face, locked onto my almost black eyes, smiled with what I could only call an invitation, and left.
I've been around a little and I recognized some of the signals she was sending and there is no question in my mind she knew she was sending them. I like to flirt but what she did was more like a challenge. I made sure the next time I saw her that day was when I said good bye and thank you.
The following weekend, about 6:30PM on Saturday my cell phone rang. It was Gail and she was obviously drunk. She was crying about a fight she had with Greg and how hard she worked at pleasing him and how she didn't think he loved her anymore. I talked with her for about an hour reassuring her until she finally calmed down. I inquired if she was ok and she answered she was and thanked me. She closed by saying how grateful she was to have me as a friend. Then she added "how come some lucky woman hasn't latched on to you?"
"I've been married twice, neither worked out very well. So for now, I'll just having some time for myself. I really enjoy living alone. I have a nice place, plenty of help, and company if I want some."
She laughed. "I'm sure you do! I'll bet they're lining up! Thanks again" and hung up.
I didn't see or talk to Gail for almost two months after that. Then one night the phone rang. She was drunk and at their cabin in the mountains. Her husband was at their other house. I learned they had another fight and I really didn't want to play referee for my boss and his wife. But, being the kind of guy I am and the position I was in, we went through a lot of the same conversation as the first time.
"You are so good at calming me down and getting me to see clearer. How come you are willing to do this with me?" she asked.
"Well, I like both of you and I consider you friends. If I can help you guys smooth out the road, I'm willing to do that or at least try by listening. Besides for the money I spent getting in touch with me and the world, the least I can do is share it."
"Does he talk to you too?"
"No, not at all about anything personal."
"Well OK then" and she hung up. Strange and getting stranger.
She was in and out of the office about once a week thereafter and made sure she came into my office to say hello. It would always start with a hug and each time they seemed to get longer and longer, not that I complained. She would often close the door and "want to get something off her chest". Each time it was an apology for her calls or her actions. I made light of it and suggested we let it go.
During that time she would call to talk about things. Each time the topic was about issues she was struggling with and seeking some advice or just needed someone to listen. Each time she was sober.
The next time she called drunk was two months later. This time the conversation went from weird to sexual and back to weird and back to sexual. The sexual innuendo part was a new plateau. It was pretty tame as phone sex goes, talking about how nice my lips were and how she thought I would be a good kisser, what a nice body I appeared to have, etc. etc.. She was embarrassed and wanton all at the same time. She quickly closed off with "I love you β but not in that way".
Notwithstanding this new plateau and her closing admission, I put it out of my mind. She was drunk after all. Until two weeks later. Her husband had gone away with their oldest boy for a long weekend. Their youngest was away at prep school. She was alone for the weekend and another cell phone call came. Had I thought about it, it wouldn't have been a surprise, but this time she was crying. I hate that β a woman crying. There isn't a guy in the world that isn't at least marginally helpless in that situation.
She started out soft and almost whimpering. But the topic wasn't either and she was slurring her words.
"I'm playing with my pussy. Have you ever played with a very wet pussy. Mine is absolutely drenched. I've been playing with it for most of the day, I'm hornier than hell, and I had to share with someone β even if its fantasy. I even shaved myself for the occasion."
"What's going on here Gail?" I asked almost speechless at her admission.
"I wanted to feel like a woman. I needed to be sexual. I had to have a release, and so I did myself. I can't get anyone else around here to do it! So I bought this big black toy that has a buzzer and its fabulous! Not a substitute but it'll do in a pinch." And she started chuckling.
I was in dangerous territory. "I'm not sure I need to know this!"
"I want you to. I trust you to keep this as our little secret. I love you but not like that!"
"Then how?" She ignored me.
"Where are you right now?"
"I'm at my house in the living room."
"Are you alone?"
"Yes"
"Take your clothes off for me. Grab your thing and play along with me."
"Gail β no!" Trying to be as mannerly and forceful as I can. She kept right on going.