Ahh, I have fond memories of my first trip, it was on NYE in 2006 when I took my first gram of shrooms. They were some ground up Amazonian cubensis I had acquired along with some high quality pot. I remember my parents had left for the evening to a neighbor's party and I had the house to myself, which is what prompted me to experiment... So, I somehow choked down what I estimated to be a gram of the shrooms in a piece of bread with a glass of orange juice. It combined in my mouth to make a soggy mess, awful texture, I had lemon in there too eeuuuch.
The taste was awful at first, of course, but it after that it began to grow on me more with each successive trip. I first noticed hints of breathing and Mayan patterns in the carpet while I was playing drums, much to my delight! That 3g baggie was the start of my first series of psychedelic experiments, I'll have to see if I can track down a spore print of that strain since it was so mellow and pleasant on the body, unlike the Mexican Cubensis I later sampled from the same place. These were all 1.5-0.5g eyeballed trips, so it's hard to compare them to say, 4g's of potent cubensis alone in a dark room
I think for New Year's Eve 2007 I couldn't work out a plan for tripping on the night of the 'eve. But I had time a few days before which I used to ingest my first RC, if you could call it that, 4-AcO-DMT, which was an equally as eye opening experience. Before that point I had never seeked out and acquired a compound myself, I had only tried the aforementioned mushrooms and LSD-which was a gift actually, for my 18th birthday. Ever since having that first experience on new year's, I've grown to enjoy having some kind of chronological significance to my trips. It seems to complete the ceremonial nature sometimes, and takes some of the hollowness out of the "Oh shit it's a week after Christmas, let's get drunk!"-type holiday that NYE is anyways... It makes the new year really seem full of promise and significance, and resolutions valid. Also my birthday is right around the summer solstice, I like tripping than just as well.