For me it's way less of the actual cigar as the context and company (this can go in several directions). I've had some great conversations over cigars, and as the cigar wound down the conversation wound down and I just wished it would keep going on forever. Often I'll sit on my back porch with my fiancee and we have really intimate time together while I have a cigar and we enjoy some wine. I wish that cigar would never end. Sometimes I'm content being alone on the back porch, and know that when I go back inside all the troubles of the day will come rushing back in force. I wish that cigar would never end so I could enjoy that quiet place for a while.
The cigar in any of the above could be a Sir Winston or a Famous Nic 3000 - it's been those and everywhere in between. Obviously I have to enjoy the cigar to not want it to end, but plenty of different cigars have filled that role.