About 7 years ago, I started to find that my good old briefs that I had worn for years were starting to bother me. It seemed like my dick was always uncomfortably squished into the crotch, and I had to constantly adjust. I began to experiment with boxers. It was strange to have my dick hang loose totally unrestrained. It felt really good and I boned up constantly. At first, I only did the boxers on the weekends. Then I took the plunge and made the switch to full time boxers. Worked out better for me. It's very rare that I'll wear briefs or boxerbriefs any more.
Once I got used to boxers, it was no big deal to freeball. It felt exactly the same - totally unrestrained. One day while dressing for work, I caught a glimpse of my softie in the mirror and it seemed as though my limp size had increased. I know that the actual size didn't change. My theory is that my penis stretched out a bit from the conditioning of giving it some breathing room that it never got before. It wasn't a drasttic change, but enough that I could see it.