My first time was with a first timer.  

When I first started I was strictly UTR/WOM and only did duos with a few girlfriends, so my first ever date was also my very first threesome. My girlfriend was very experienced and noticed I was shaking like a leaf on the elevator ride up. She assured me that the nerves would subside soon enough and to just act as though I'm fluent in practice. Once we reached the room we were greeted by a very handsome, but visibly shy silver fox. A couple glasses of wine in and we all began to loosen up and he let slip that it was his first time. I felt a wave of relief and confessed that it was mine as well. Being as my girlfriend was the most experienced of us she acted as the ringmaster and fun was had by all. It was mind blowing and goes down easily as one of my top 10.