This is going back MANY years. I was 24 (m) and engaged and still a virgin. My fiancee was a virgin too — it’s not like we were saving ourselves until we were married; my fiancee was just very uptight. And so… I waited.
But I had a female co-worker named Judy who was a about 11 years older than me – and we were REALLY great friends. We got along really well, enjoyed each other’s company, laughed, had fun, worked really well together. She was great. She was also stacked. Like SO stacked. I used to catch myself staring at her tits constantly.
Anyway…we worked together really closely, very long hours, very late nights, and I developed a huge crush on her but never did anything about it or said anything about it. Our job required some frequent travel, and this once time, we had to go on a business trip to Chicago with a team of about 8-10 other people. So we were all staying in the same hotel and at night or during down time, we’d hang out in each other’s rooms watching movies, ordering ridiculous amounts of room service on the client’s dime and having as good a time as we could given the long hours we had to work.