I’ll never forget my first time. She was an assistant (not mine) at work. She was a few year older than me but fucking gorgeous.

We flirted for nearly a year. Then we went on a business trip together. I knew it was my shot. I was convinced the risk was worth it. Even if she slapped me for trying something, I had to do something.

We had a late dinner and some drinks. On the way back I mustered all my confidence and told her how great her ass looked in those jeans. She just kind of giggled. So I reach out and gave her ass a long tight squeeze. Then I waited to see if I was going to get slapped or kissed. Haha

Well neither happened. So I put my hand back on her ass and pulled her close. We finished the walk casually talking while I squeezed her ass as she leaned into me.

When we got back to the hotel I walked her to her room. As she stood there we looked into each other eyes for a moment. I then leaned in and laid the best passionate kiss I could do.

That was enough for her, she stepped back and pulled me into your room.