She was sitting across the table from me. Late forties. Short-ish and well groomed hair. Think Claire Underwood from House of Cards, but hair charcoal-black. Face was pretty, but you could tell that life hasn't been kind. Dark red matte lipstick. Black dress that is tight around the chest, but loose around arms and below the waist. Breasts are popping from the dress, but there is no deep neckline, so the mounds on the chest are the only thing to evaluate by. They are not huge, but more than a handful with some natural sag. Zipper on the front that I just want to rip down.
Her name is Ivy.
But we are not on a date. Far from it. This is a small work dinner - just 8 people at a nice restaurant. Ivy and I have worked at this company for over 7 years now. Difference is that I started after university and had work my way up. Being 28, I am still the "kid" at the table. I have had the luck to work closely with Ivy for several years and get to know her quite well. She is extremely smart with a great personality. And I have had a crush on her ever since I first met her. Always had a thing for older women.
She has been happily married for over 20 years and has children who are adults now. But that has not stopped us from making comments to each other that HR would probably look down at. But it has all been in jest. Always. I would never make a move on a married woman.
Few years ago at a company party, everyone was drunk deep into the night. The DJ was still playing and Ivy asked me to dance. Which was probably more like stumbling around since it was quite a fast song and were drunk. At the end of the song, in my drunk mind I thought it would be fun to squeeze her ass. I instantly thought I had made a huge mistake. But she just smiled at me and went back to her group of other work friends.
Not long after that party, her husband suddenly died. It hit her very hard. She took time off work for a while and was not really herself after that. All the dirty jokes ended between us. But we remained good work friends.
But back to the dinner. It was very pleasant. We were enjoying good company, food and drinks. I was driving, so I just had a small beer with the starters. Ivy had had 4 or 5 beers and was quite tipsy. She had asked me if I could drive her to her sister's family house after dinner since she plans to spend the weekend with them. She knew that I would likely agree since it is on my way home anyway.
The dinner ended. Everyone paid for themselves since this was not company sponsored. Ivy and I walked back to my car which was parked nearby. Drive to her sister's house was about 45 minutes. We were remembering some of the fun conversations from the dinner and simply having a nice chat.
As we were exiting the city and started driving on a smaller country road, she suddenly put a hand on my thigh. Something sinks in my stomach and for a second I am trying to figure out what to do. I look at her, but she is just looking ahead with a barely visible smile on her face.
I feel her squeeze a bit and take it as a confirmation that this is no accident. I figure - I am single, she is single (as far as I know) - let's see what happens. So I reach across and put my right hand on her thigh. At this point she is stroking my leg and moving closer to my crotch.
I respond by pulling up her dress enough to expose her bare leg, so I can caress her leg and inner thigh which is quite warm. By now her hand is already firmly on my crotch. Although I am wearing jeans, I am sure she can feel that my semi is turning into a proper boner.
Ivy casually, as if talking about weather, suggests that we should find a quiet sideroad. And we are running out of time since there are only 10 minutes left to the destination. But I see on the satnav that there is a tiny road diverting from the main one and going into the woods not far ahead.
While we are approaching the wooded road, I become bolder. My hand is now firmly between her legs, which she graciously spread as much as the car seat allowed. And I am rubbing the front of her lacy panties. The whole area is very warm and slightly moist from the sweat.
