I actually enjoy the feel of my fingers once the calluses start to form. It certainly makes holding the chords easier. Until I get a nice layer of protection, playing for any length of time in quite uncomfortable. I kind of wish that I could develop a similar sort of padding for my arm and shoulder as playing for a while really starts to wear them out.
The discomfort is worth it in the end. My boys love singing along with many of my Christmas songs--especially "The Kidnapping of Santa Claus." It's also fun to play in the halls during the last day of school before break. Although my guitar skills are rather meager, most of the students seem to appreciate the music.
However, before I can play for that length of time, I need for my fingers to build up their natural protection.