Day 12

For this day, I decide to try out a pair of old-fashioned tighty-whities. Grandpa panties. Sanitarium undies. I take them off within seconds. There’s a reason I stopped wearing these. They make me feel stupid. They dig in, and in strange places, too.

And, of course, they’re white. Please note that in 2019 there’s really no reason to wear white underwear. Why would you ever do that to yourself? The majority of undies I try for this assignment turn out to be either black, because manly, or gray, because designers want it to look like your dick is a fucking elephant. Both colors are fine by me. White is out.

Day 18

Time to test out a pair of MeUndies, the direct-to-consumer underwear start-up that has purchased ad space on every last podcast on the entire fucking planet hosted by a white guy. These are very jazzy undies. My first pair has bananas on them. Not terribly subtle. The other pair has pink and purple flowers all over them. In general, dads my age do not want you to notice their underwear, and so banana undies are a real issue for me.

MeUndies are made from something called micromodal, which I guess is modal but super tiny. (Modal, it turns out, is a relative of rayon.) Unfortunately, MeUndies designers have seemingly failed to account for the existence of the scrotum. This is a real problem if you’re an older fellow like me and your balls have dropped into the southern hemisphere. It can feel jussssst a bit bunched. Micromodal is comfortable at first, but then comes to feel like you’ve had, in the words of George Carlin, your testicles laminated. Also, there’s no dickhole. My kingdom for a dickhole.

For the full effect, I test out the banana undies by wearing them to the gym and seeing how it feels to strip down in front of my fellow club members with them on. I leave the ’nanner undies out in an open gym bag, along with the rest of my sodden gym clothes, while I shower. Please note this is standard operating procedure for me at the gym. I’m not stripping like I’m working at a burlesque show. I haven’t done anything out of routine, and yet I become VERY conscious that people might see my banana undies sitting out and think I’m a fucking weirdo. Then I change into the flower undies in the general dressing area, and I feel even weirder.

Day 23

It’s time to get into the freaky stuff. One luxury brand has sent me a pair of black, sheer, lacy undies. I put them on, and you can see my ass through the fabric. These are Prince undies. I go and look at them in the mirror. I do not look like Prince in them. My first instinct is that they look ridiculous. But on a much deeper level, I feel kind of sexy—lovesexy, one might say—even though I know no one else on earth would feel likewise if they saw me in these things. Also, the tag is running right down my crack, which spoils any initial flirtatious effect.

I appreciate underwear that tries to make you feel sexy. There’s nothing wrong with that, no matter how much of a dad you happen to be. But I can’t see myself feeling that sexy all the time. Nothing would get done, and I can’t pull off being the kind of dude who arches an eyebrow at himself in the mirror on a daily basis. Off they go.

Day 26

The Prince undies are not the only pair I try that cross over the Rubicon into the territory of male lingerie. I test out a pair of bikini briefs. There’s ONLY waistband on the sides of these. No other fabric for my ample haunches to hide behind. I think they make my butt look good, but at what cost? I also try a pair of boxer briefs that have a literal pocket for my dick sewn into the inside, either to keep my junk cool or to make me feel like a meat smuggler. Then I test out a couple of jock straps, along with a pair of boxer briefs that has jock-style ass straps sewn directly into the fabric, for reasons that escape me. It feels like I’m wearing a butt bonnet.