The Undy Conversion

“Ewww, Tidy-whiteys!”  This cry echoed in my head even as the image of the man on the TV screen left it.  A friend whose opinion on just about everything I give great respect had made it.  Maybe this was why, for the first time, I found myself wondering if my choice of underwear was the right one.  I had given it some thought in the past, but always I had been swayed from even considering change by the fact that my underwear was just plane comfortable. 

            Let’s just something straight first, in my own defense, I have only ever, in my entire life, owned one pair of tidy-whiteys, and those were purchased while I was away from home and had forgotten to pack spare underwear. I was forced to buy them and I have since misplaced them in the laundry.  But I did wear jockeys almost exclusively from the time I wandered out of pampers until last year.  Blue ones, black ones, grey ones, just not white ones. 

            Since that early point in my life, I had been happy with my underwear.  If you ask me why I wore them, the answer seems simple to me, it is what my dad wore and it was what my mom bought me.  End of discussion.  I never really considered changing.  Occasionally I thought about boxers, but growing up they always seemed to be the thing that those weird Italian guys who always had a t-shirt tucked into them.  You know, the hairy dad-type guys that you could see in the Godfather, not one thing attractive about them in the slightest.  When I found some friends in university that wore them and swore by them, I thought about them, but they always seemed bulkier, thicker waistband, more fabric and etc and therefore less comfortable. And then there was the story my friend told me about the first time he ever work silk boxers and how it made him walk around all day with a semi.  I just didn’t think they were for me.

            And you know what, jockey’s are just comfortable.  They are, really they are.  They stay out of the way and yet protect your package, they hold you up with support but never clinch, they look like shit but still do the same job even though they have holes.  Oh, I know, I know, is there anything worse than seeing a guy wearing a ratty pair of jockey’s with holes in them?  No, after seeing my dad in them, I can honestly say, not.

            For a while before my friend’s comment I had been thinking about what I was wearing. I knew it wasn’t sexy. It is not like they could be, I had seen me and others in them.  For a while, I thought that briefs were the sexy underwear.  How could I not, all the really hot looking guys in movies wore them.  I even bought some.  A four pair pack.  For a while I wore them when I wanted to feel sexy.  Then one day, I realized that I looked awful in them.  I realized that there was no difference between them and Speedo’s.  My god, I looked like a chubby guy in a Speedo!  All of a sudden, I didn’t feel sexy in them anymore, I felt silly.  To the back of the drawer they went and I started wearing them only when desperate.  Saved for the day before laundry day.  There is not a person alive who has seen me wearing those briefs.  This is something I am thankful for.  (ironically, guess what I am wearing as I write this)
            I sat for a while after my friends comment, mortified.  Embarrassed that I could wear something that was fit for such ridicule by someone I respected so much.  Then I decided to ignore that, because, they are still comfortable.  But over the next couple of days I realized something else, I might not care what my friend thought of them, but her thoughts would likely be indicative of the thoughts of other people around me.  Female type people, people that I might be interested in.  People I would let see me in my underwear perhaps…people who in judging me, would be doing something important in terms of relationships and sex.  That weekend, I went out and bought some.  Cheap ones mind you, but nice.  Luckily I picked a good set, because I have found some less comfortable ones since then, but these, they were comfortable. They were nice, they felt good.  I looked pretty good.  I was happy.

            I did notice something a little different for the first while.  Honestly, well, I just hang a little different in boxers, sit different, you know?  And this difference, more free, more exposed, rubbed me a little.   For the first couple of weeks, at the oddest times, I would be shocked to find myself rather excited, shall we say.  It got worse when I bought some more expensive ones, ones that I found sexy in some way, Hilfigers, or Ralph Lauren’s.  After a while though, I acclimatized and now I don’t get the random reactions, but for once I have what I call my ‘sexy’ underwear that I wear when I want to feel sexy. 

            I don’t think I will ever go back to being a jockey boy.  I have now purchased enough boxers to equal the number of jockey’s I used to have and I am a convert.  But you know…they are still comfortable…and…now…I don’t HAVE to do laundry for twice as long. 

First published on underwired.net in July of 2000 (now dead)

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