About eight years ago I started working as a salesman for a computer software company. It was a growing business and the work was steady. I had a good group of co-workers and supportive staff at the office. I was out in the field a lot and my time at the office was limited.
Every time I was in the office, I tried to go around and introduce myself to everyone. Some of the staff would chat with me but most of them were too busy or stressed out to even concentrate on a conversation. There was one particular administrative assistant that was very friendly. Her name was Diana. She was actually the wife of one of my supervisors. His name was Roger. She worked in one of the back offices and provided support for the field staff, which included me.
Diana was not exactly what society would consider attractive, but she did have a really cool personality. She was plump with light brown hair and wore glasses. She tended to wear loose fitting clothes because of her figure. But there were occasions when she would dress up nicely and would show off her curves. I always notices her thick soft ass but one particular day she had put the girls on display.
It was around 3:30 on a Friday afternoon. Most of the staff had already left for the day. I walked passed Diana's office.
"Hey there!" she called out.
"Hi," I responded. "How much longer are you staying?"
"Oh probably about two more hours or so," she replied. "I have to wait until the Fed-Ex driver gets here with a package and he is running late," she said.
I noted that Diana was wearing a red colored button down blouse. The top couple of buttons were undone which exposed her neckline and the top of where her cleavage began. That is all I needed, and being the typical horny male that I was, I decided to step into her office and sit down in one of the seats next to her desk.
We had a conversation about work and then started to discuss other things. I asked her if she and Roger had anything planned for the weekend. She told me that he was going to be away until tomorrow night which she referred to as "typical." I knew that Roger worked a lot and would travel often and she seemed to accept the idea because he made really good money.
Next thing I knew it was about 4:30. She looked over at her clock and then bent down to get something out of the bottom drawer of her desk. I got my first glimpse of her large boobs being restrained in her top. I could see she was wearing a white bra which was under some stress at the time. She shuffled around and the drawer for a moment.
"So what do you say," Diana asked as she pulled a bottle out of the drawer. It was a bottle of crown royal. "It's almost 5 o'clock, and I'm ready to relax."
"Uh, are your sure about this?" I asked.
"Yeah, it'll be all right, my husband and the other supervisors usually hang out in here after work all the time," she replied. "Hey, the Fed-Ex guy just pulled up, do you mind running down to the front desk for me?" she asked.
I went down and collected the package from the front desk and returned to the office. Diana had two shot glasses set up on her desk. She poured the crown royal into them and slid one towards me.
"Bottoms up!" she said.
I grabbed my shot and we clinked glasses. We simultaneously downed our shots. They went down smoothly. She started to pour another round.
"One more for the road," she said as she finished pouring.
"Why not," I said as I reached for the glass. Once again, we clinked glasses and downed the shots.
"Ahhh," she said. She put the bottle away and began to pack up her belongings. "Got any plans tonight?" she asked.
"Just gonna head home and relax," I replied. "What about you?"
"I'm going to the Mexican joint for happy hour," she said. "They got two for one Margaritas," she added. "I'm gonna go hit on the bartender and maybe he'll take me home tonight," she said laughing.
"Well, if you drink to much, make sure to call a cab or you can even call me," I told her. I wrote down my cellphone number and handed it to her.
"Ok, thank you," she replied. She gave me a hug and I left the office.
A couple of hours later, I'm sitting in my apartment when I received a phone call. It was Diana. She told me that she was in no condition to drive and was still at the Mexican restaurant. I told her I would be there in about twenty minutes.
I pulled up to the restaurant and sent her a text message letting her know I was there. She did not respond and I tried to call her. She still didn't answer, so I went in to find her. She was standing by the bar talking to the bartender. I walked over to her and tapped her on the shoulder.
"Oh hey," she said as she put her arms around me and kissed my cheek. She looked at the bartender and said "he's my ride and he's driving me home," as she laughed real loud.
