To wear myself, like many others that have already weighed in, it's roughly 50/50 between Calvin Klein and Jockey if I'm in boxer-briefs (and nearly a lock that my undershirt is from Jockey too; their Staycool+ V-necks1 are such an under-the-radar winner). That's generally when I'm in business attire, which I just realized has become an ever-decreasing part of my life in recent years. More often you'll find me out and about in just a button-down shirt with the sleeves rolled up, jeans, and Brooks sneakers. Not only does it free me up to get my hands dirty when I see something that needs doing, but it feels like in recent years people respond better to it than they do the suit and tie.
In those instances, you can take to the bank that I'm wearing Tommy Hilfiger Knit Cotton boxers, usually navy blue but occasionally fire engine red. Sadly my time with them will soon run out as, like everything else in the God-damned world, the last pack I bought was unrecognizable, they'd switched to a much thinner, cheaper cotton, an elastic waistband that had all the tactile properties of new burlap, and the fucking fly was cut so ridiculously high that I felt like a European park fountain everytime I had to piss. I'd love to have chance encounter with the quant jock who gave the go-ahead on that corporate decision in some dark alley in the middle of nowhere, let me tell you… But I digress, because regardless of what they've become, I will always reflect fondly on them because they were the underwear of choice for the guy who popped my cherry some 20+ years ago. I'd love to tell you that I was so taken by how good he looked in them that I became an instant convert, but alas, he actually wasn't that good-looking and the underwear didn't exactly help his case either. Lucky for him, that registered very little to my very horny, very virgin, 16 year old brain.
After we'd accomplished what we set out to do and had worked up quite an appetite, he suggested we walk over to a diner a few blocks away and have a bite before I left to go home, his treat. Having been raised with enough sense never to turn down a free meal, I pushed through my awkward feelings and impulse to make my retreat long enough to accept. I remember thinking that everything I'd heard about women "walking funny" after good sex was surprisingly applicable to me as well while we walked, despite the experience not really having lived up to my teenage fantasies of a heavenly chorus singing and getting an instant soulmate from the deal. By the time we'd reached the diner I started to become aware of more urgent concerns, though, as the confluence of taking my first stroll through the world as a non-virgin and our decision not to use a condom, plus a little planetary gravity, was working to leave me with more than just the sweaty butt crack I chalked it up to as we walked. I knew the instant I sat down on the vinyl seat of our booth that there was a wet spot forming in the rear of my boxers beneath my (have you already guessed?) khaki Dockers, and instead of excusing myself to the restroom and performing triage, I decided that I'd just sit there and pretend it wasn't happening.
Thankfully in the end it wasn't the major catastrophe I had been picturing in vivid detail the entire time we ate and I was able to exit the establishment without making my companion pull the fire alarm or create another similar distraction. It hit me on the walk back that my situation was simply the price one must pay to venture outside without their virginity and along the way I leaned over to whisper conspiratorially in his ear about my condition. He apologized several times despite my insistence about there being no need for it, and when we'd reached my car parked in front of his house, he suddenly told me to go back inside with him. I was already trying to settle on the best way to tell him I had no interest in an encore as he closed the door behind us and matter-of-factly told me to start getting out of my underwear while he went to his room to get a pair of his for me to wear home. The thoughtfulness of his reaction bowled me over and without protest I just said okay and did as I was told. I'd never worn anyone else's underwear before and for reasons I'm still powerless to explain, even after what we'd done not long before that put me in this predicament, him giving me a clean pair of underwear before I left was hands-down the high-water mark of the sense of intimacy I felt a part of that day.
I hollered up to him that I had a pressing question to ask once he'd already gone upstairs and was probably almost to his bedroom, and he appeared again at the top of the stairs to hear it. I still wonder exactly where the idea I was about to voice came from within me and whether it's proof of my having an unusually high level of sentimentality or just a hopelessly dirty mind, but the question I asked was if he'd be okay with giving me the underwear was wearing rather than a clean pair. I was already beating myself up silently for sounding like the world's biggest perv during the brief moment of silence while he considered my request then surprised me by saying he was fine with it if I was sure. He never asked me why I wanted them, which was good because I don't know what I would've said, I hadn't gotten that far myself. He looked sexier taking off his shoes and pants just then than he had the first time, I decided, and when he was standing there bare-assed as I pulled them up my thighs and into position around me that encore I was eager to avoid minutes before seemed instead very tempting. I loved how warm they were already and how well they fit and told him so more than once as we both put our pants back on and we walked back out to my car and said goodbye.
Of all the day's events, that drive home remains highest on my list of fondest memories. I was deep in thought the whole way, parsing my feelings on sex as an actual physical experience and not just a hormone-fueled fantasy, wondering if there was still a way I might not be gay despite being pretty certain I was doing something inherently very natural to me while it was happening, and a surprising amount of time realizing that my Mom had been buying me absolute garbage underwear for my ENTIRE LIFE in comparison to what I had on right then. I smelled them while I jerked off like a man possessed that night in bed, reliving everything we'd done and the smell of him. Afterwards I hid them away, not wanting to explain how I ended up wearing another's guy underwear the next time laundry was done, and when it was finally time to pack up my things to go to college they were one of the first things in the box.
I still have them to this day, even still wear them every once in a while (if for no other reason than as a reward for still being the same size now that I'm staring down the barrel of the big 4-0 as I was in high school :cool2:), and the proof of their quality is in how well they still fit and look exactly how I remember they did as he held them out to give to me. They were the only sense of comfort I felt at all when I wore them on a very difficult day about a decade ago to join his family in saying a final goodbye to him so much sooner than we should've needed to. This is the first time I've ever shared this story, strangely, despite how fondly I reflect on it. If you made it this far, thanks for allowing me to finally get the chance to do so.
That's how my favorite brand of underwear became Tommy Hilfiger, thanks to one pair in particular, though I'll go to the mattresses with anyone who disagrees on principle; though I haven't gone out of my way to try a ton of other brands, every time that I have I find them wanting to some degree in comparison. It will be with a heavy heart that I begin the search for a new brand to replace them when those that I have now come to need it.
1Jockey Staycool+ V-neck Men's Undershirts
) and getting sober while dealing with the 18 months of statutory driver's license revocation. On most days during that chapter of life my mood was foul, and that's being charitable; some days I might as well have been Satan's new apprentice. 
Anything that even tangentially highlighted the fact that I had neither vehicle nor a license to use one would've done well to give me a very wide berth.
