I came late to the boxers party. I used to hate boxers, but now I love them and won't wear any other kind of underwear. Here's how it happened.
I wore briefs from the time that I moved on from diapers as a toddler all through grade school and high school. Jockey made some really nice SLIM GUY briefs in the late '70s in a multitude of colors with white contrasting waistband and legbands. Jim Palmer, a baseball star, did many of the Jockey ads, and many young guys bought Jockey brand after seeing Jim in his Jockey briefs. I was very fit, and they looked smokin' hot on me. They felt good, too, for weight training, running, and racquetball. I pretty much wore them all day every day. I bought a few different boxers just for fun because my best friend wore them. I could never get into boxers because I didn't like my junk bouncing all around. Plus, I'd always pop boners when I wore boxers.
Fast forward to the mid '90s and the height of boxers popularity. So many guys at San Diego State wore boxers when I was in college, and they would always dress so you could see their boxers. I just could never see why they liked them. I'd wear them sometimes knowing that I'd be walking around campus with a hard on all day and wore boxers to be kinky. Still didn't like how they felt.
The thing that turned me in the mid 2000s was one day I saw a young guy at the gym who was wearing white mesh gym shorts with striped boxers. You could see the pattern of the stripes show through the mesh fabric. Korny, yet hot in an odd sort of way. Even better, you could plainly see the outline of his hanging dick moving around as he walked from one piece of equipment to the next. It was amazing how visible his dick was. When he layed spread eagle on the bench press, I about died. It was easy to follow the stripes as they curved around his dick head. It was so obvious, that it killed me not to stare. All of a sudden, I saw the sexy side of boxers. This guy knew what he was doing, and purposely dressed to flash everyone at the gym. It made me ferociously horny. I had mesh gym shorts at home. I had boxers at home. When I combined the 2, I love how my dick outline looked hanging in gym shorts instead of an undefined lump with briefs. So, I had a new found motivation to give boxers an honest chance. I liked how my dick showed in corduroy jeans and track pants as it hung down the right side. It was cool to catch people checking me out and I didn't feel the least bit embarrassed that they were looking at my dick. After a few weeks, I got used to hanging loose and knew that I could never go back. Now, I can't stand to wear briefs or even boxerbriefs. Loose feels better. I can deal with wearing cycling shorts when I ride my bike, but all other times, I can't handle anything snug. It's boxers or freeball for me.
San Diego Boxer Guy