Many thanks to tuhahkhan for editing this story.
Eileen is a tall ungainly woman. She is on the thin side, but with overly broad hips, an oversized butt, and no boobs. Or almost no boobs. They are low mounds, with areolas surrounding her, quite prominent, nipples. She has a plain face. Her straight mousy hair is cut at chin level.
Eileen is a very intelligent woman, but had only finished high school. She works as a paralegal. She is very good at it. Her income is sufficient to maintain a middle class lifestyle. Her home is in a Boston suburb a short commute from her job.
Eileen dresses very conservatively for work. Typically a well fitted suit, usually with a skirt. Occasionally she will wear a pantsuit. Her blouses were always high necked. Off work she is also a conservative dresser. She prefers dresses or skirts.
Eileen is friendly, outgoing; but she is not an attractive woman. Until recently she had very little sexual experience. At one time she tried bar scene looking for love or companionship. The results weren't at all satisfactory. A few times she was able to meet someone. But, the guy never called her again once he got her in bed. Eventually she quit drinking, except for a glass of wine with dinner, because it wasn't doing her any good. Eileen is a realist. She does not bullshit herself. She has her fantasies, but she realizes they are exactly that.
Eileen's fantasies are usually about young, well hung studs lying on top of her giving her a hard fuck. She usually masturbates to these illusions. Sometimes she gets the hots for one of the young lawyers at the firm where she works, but she is always careful not to show any outward sign of her dreams. She doesn't have enough experience to imagine any other way than the man on top. She had experienced oral sex a couple of times, but she had been drinking so her memory of the event was hazy. She did not know if she had enjoyed it or not.
By the time she was forty-five years old Eileen had accepted the fact men weren't very interested in her. She thought about trying women, but she didn't feel sexually attracted to them.
Shortly after her fiftieth birthday Eileen met Robert. Or maybe one should say Eileen met Robert again.
Robert had grown up in the same neighborhood as Eileen lived. He had gone off to college and a career. Eileen had only seen him on a couple of occasions since, at the funerals for his parents. Robert's parents had stayed in the neighborhood after their retirement. His father had died about six years before. His mother passed away only four months before.
Eileen was sitting in for the receptionist, while she went out for lunch, when Robert came into the office. He was there to check on some things about his parent's estate. Eileen greeted Robert, she remembered him as a bright child who was always curious about things. She had last seen him at his mother's funeral. She had thought of him as a hunk. He was in her dreams a few times after that.
Robert remembered Eileen very well, while he waited they chatted about their old neighborhood. Robert concluded his business quickly. On his way out he invited Eileen to lunch, so they could talk about the old neighborhood. "I don't know many people there anymore," he said, followed by. "Let's make it on a weekend so you won't have to rush back to work." Eileen agreed, they decided to meet at a restaurant they both liked the following Saturday.
Eileen had Robert in her dreams again that night. She imagined him with a big cock. Her vibrator was the substitute for him as she pumped it into her wet pussy. She could almost feel him lying on top of her.
Saturday Eileen took extra care in dressing wearing a dress just a little bit low cut. She wished she had cleavage to display. She did think she looked good in the dress she chose, even without big boobs. She had thought about wearing a padded bra, but decided against it. She took extra care with her makeup being careful not to use too much. She had no illusions about this being a romantic date. After all Robert was only in his late twenties to her fifty. But she could fantasize. She would carry the memories home, to use in her dreams.
Robert was waiting for her when she arrived at the restaurant. "You look very nice." He told her. He had arranged for a secluded table where, as he put it. "We won't be disturbed by other diners."
Robert
:
I'm Robert, not Bob, Rob, or Robby. I'm twenty eight years old. I stand 6' 1" weigh 190. I am well built, not bad in the looks department. I've been told I'm very attractive to women. I must admit I'm seldom lacking female companionship, if I want it. That may be due to the fact I am very well hung, or that I like going down on women. But it may be due to a couple of quirks in my personality. First I am attracted to older women. Second I am attracted to unattractive women.
I usually have two or three affairs going at the same time. Once I found myself dividing my time between five women, but I found it to be a bit too much. I try to be honest with them all.I never imply they are the only ladies in my life. In fact I make it plain they are not.
When I saw Eileen in the lawyer's office I immediately recognized her. After chatting for a while I asked her to lunch. She accepted quickly. We made our arrangements to meet.
I arrived at the restaurant first. A generous tip secured us a nice, secluded table. When Eileen arrived I complimented her on her looks. It wasn't false flattery, it was obvious she had taken extra care when dressing.
We had a very good lunch. I found Eileen to be an interesting person. She was intelligent and well read. She kept up with current events so she could discuss them logically. Our conversation ranged far further than the old neighborhood. But, she also seemed naïve about some things.
After an hour, or so, of conversation with a couple of glasses of wine. I told Eileen, "I have certainly enjoyed our conversation. You are not only attractive, but brainy too." Eileen blushed a little. She thanked me for the compliment. I continued. "I wish we could continue our chat, but I think the restaurant wants their table back."
Eileen's response was. "We can go to my house. I am enjoying myself. It is so seldom I have such interesting conversation."
"Ok," I agreed. "I'll meet you there." I followed Eileen to her house. She drove into her garage. I parked on the street, not quite in front of her house. I didn't want to make it too obvious she had company. She waited for me in the garage. We entered through the kitchen.
"Would you like another glass of wine?" Eileen asked as she showed me into the living room indicating a place on the couch.
"I seldom have more than two glasses, but with such enchanting company I will make an exception." I replied.
Eileen showed a slight blush again. "Thank you Robert, the pleasure is mine."
I sat on the couch. Eileen brought a couple of glasses of wine for us. She sat leaving a space between us. We both turned so we could talk. After fifteen minutes, or so, of talk Eileen offered to show me around the house. It wasn't big but it was very well furnished. I complimented her on it as we returned to the living room.
Eileen said then. "I am really enjoying this afternoon. It is so seldom I get to entertain gentlemen." She went on to ask. "Have you ever married Robert?"
"No," I replied, "Never."
"I would think some young lady would have snared you by now." Eileen had that light blush again.
"Actually Eileen I am not that interested in young ladies." She looked baffled for a moment until I continued. "I am attracted to older women. And to intelligent women."
"Oh." Was all that Eileen said.
"In fact." I continued, "I find you to be very attractive."
Eileen
:
'My God,' I thought. 'Can he really mean that?' My emotions were a mess. A thrill ran through me, nervousness too.
"Robert," I said. "Do you really mean it? Please don't toy with me."
