I'm twenty, in college, and I've been freeballing for as long as I can remember. I've always loved the comfort.
What I like to do every night, even though I'm a freeballer, is wear shorts. I'm a dedicated freeballer otherwise. I'm uncut and recently I've been wearing shorts to sleep in because of the morning pleasure I get sometimes. My dick is just long enough that the base of the bottom of the head is against the waistband when I have a boner. The head pokes out, but the bottom of the head is just at the top of the waistband at the most sensitive spot. This provided me with a lot of pleasure when I wake up. I almost always have a boner when I wake up each morning, and the waistband of the boxers I've worn in the past doesn't do much. But I love these shorts for obvious reasons. The roughness is just right. It's so good that usually I just have to pull my foreskin back and forth over the head a couple times before I cum. The head is so swollen already that it doesn't take much to reach orgasm.
The problem I have is that sometimes it's a little too rough. Other times I wake up with some pain. I did notice, however, that I can adjust the drawstring to loosen it a little bit and it can mean the difference between waking up with pain or waking up with extreme pleasure.