So I had recently finished a project for my boss that we had been working on for about 5 months. This was a huge project and after we had completed it my boss Terry invited me on an all expenses evening which included a hotel for the night, evening meal and drinks paid for by him as a thank you. My boss is a 56 year old man, medium build, quite athletic and an overall nice guy. His wife passed away a few years ago and ever since then he just works constantly. He invited my gf for the night as well as he said it would be a great opportunity to meet her and learn more about me and my personal life.
So it came to do the day of going away, my gf frantically packing her case and stressing about what clothes to take. We knew it was going to be a nice fancy meal so she packed a dress and heels for the evening, and I packed a suit. We met Terry in the train station and all travelled together to the hotel. When we arrived we couldn’t believe it, this was the fanciest hotel we had ever stayed in. We checked and agreed to meet at the hotel bar in a couple of hours to give us chance to get ready. My gf looked amazing, her short dress that showed off her legs and also showing off a modest amount of cleavage, and heels that complimented it all.