My first experiences happened a few years back and was set under some rather sad circumstances. Myself and a few friends had recently come into contact with an old friend of mine who after reuniting with said he could get some dmt for all of us to try. After waiting around for a while for my dmt holding friend to call my friend (who i was with at the time) who I will refer to as Gamgee got a call informing him that his father was going to die that night from brain cancer that he had been battling for quite some time. After a few horrible hours in the hospital gamgee thanked us for being there but told us there was nothing more we could do for him there and that he needed to be alone with his dad for his final hours of life.
After we left the hospital with sad thoughts in our heads and discussions of what the afterlife might be like (Tolkien's white shores of valinor came to my mind) we headed over to my friend with the dimitri's house to take our first respective jumps into hyperspace. I was the first to take the jump and was honestly quite terrified from reading an erowid trip report the same day about someone who said dmt completely twisted and rewired their nerves painfully, not a good way to start. My dmt holding friend sandwiched said dmt between some finely ground marijuana and gave me the rundown of the 3 hit method and how long I should hold my hits for. He put the bowl into my homemade waterpipe made from a cows horn (bong of destiny anyone?) and started to light the dmt sandwich as I inhaled.
After a few seconds of taking the first hit it hit me so fast and so hard that I completely forgot where I was and what I was doing so I blew out my hit without thinking about it. "Hold It IN!" my friend said and then i remembered I was smoking dmt for the first time. With the second hit fractals exploded of the lighter and the room turned into a giant fractalized dome which looked like the inside of an insects eye to me but every section of the dome was a wierd sort of "S" symbol. I took the third hit and gulped down some water and closed my eyes.
Upon closing my eyes I found myself in a sort of liquid hyperspace tunnel that was changing colors faster than I could pay attention to. Inside this tunnel with me were some of the most complex multicolored geometric objects I have ever seen that would respond to and try to mimic my thoughts. For example I remember having a very brief thought of my girlfriend and the objects tried to take the form a girl with blonde hair. After a while of this happening I came out into a sort of dark space with a lot of complex fractals and the first hyperspace entities i would ever see. I recall an entitiy that looked like gumbi with the head of a brontosaurus, one that looked like a mayan bird god and one that looked like the wierd cat creature from ATTACK OF THE CLONES with a snake for a tail and whenever it took a step it would make a sort of wierd mechanical "whomp" sound that would echo for a while. Though I tried to communicate with them none of them would return the favor though all of them had this look and feel to them that suggested that these appearances were just ruses and they were appearing to me as they wanted me to think they looked if that makes sense.
After a while of these strange entity encounters everything was sort of wiped clean into blackness and in the "distance" what I can only describe as the blueprint of another dimension began to appear. It is hard to describe what I saw but what I can say is that it was ever changing and the boundaries were constantly shifting. I remember thinking when i saw this blueprint "Bruce(gamgee's dad) is in there. In the "center" I saw a sort of crystal flower mandala with a blinding white light shining out of the center. Upon seeing this I had the thought "I need to get into the center of that, but how?". Upon thinking this a voice sounded in my head that I really don't think was mine which said "You need to know more before you can enter here".
The rest of the trip I really don't remember very well but it really is inconsequential. Ever since this trip I have had somewhat of an obsession with dmt and smoke it ever so often.

Love All, Rest in Peace Bruce

Intriguing report, it's pretty common to link DMT with death, weather or not the two are related, nobody can say for sure, but once I had an unwelcome invasion of images of someone I knew who told me they had tried to commit suicide, which was distressing, but I managed to sink into a nice trip afterward.

I'm sure this person you knew is resting peacefully now.

Yeah after smoking dmt for a while I really no longer fear death and I know it's going to be a hard but beautiful thing. Still fear pain though, illusion though it may be.