We've all been in this situation: You're at a store looking for some new clothes. When you get to the underwear section, you spy a mannequin with a body type similar to your friend Danny's, dressed in a quirky pair of Simpsons boxers that you just know would look great on him. Being a generous person, your first impulse is to spend the few bucks on a nice gift for a close friend. But then a voice in the back of your head reminds you that some people seem to think that simple gesture sends the "wrong message," so you glumly put them back on the rack, forever wondering, "What if?"
I'm here to tell you that's just nuts.
If you find a kooky pair of underwear that one of your buds would enjoy, then there's no reason you can't buy 'em and give 'em. Let people talk! Who cares what they think?† Everyone wears underwear, so what better present is there? It's totally natural. Never underestimate just how good a new pair of nice-fitting cotton boxer-briefs can make someone feel. It's fun, it's absolutely innocent, and he'll think of you every time he slips them on. To me, that is worth a few dirty looks here and there.
Let me give you an example. A couple weeks ago, I was at the department store, and I found a pair of underwear that really reminded me of my friend Terry. He'd been kind of down lately, and the color of the underwear would bring out his eyes really well. So I thought, "What the hell," and put them in my cart. Later, we went out with some friends for wing night, and when there was a lull in the conversation, I presented them to him in front of everyone. Sure, the guys razzed him for a while, and he seemed a little embarrassed, but when I asked him about it later in the bathroom, he didn't even say a word. Obviously it didn't bother him, so why should it bother everyone else?
It is so not a big deal. That's just what friends do.
I used to waste a lot of energy trying to figure out the best time to give one of my close male friends a pair of silly underwear as a gag. I thought I needed a special occasion, so I would always find myself with, like, 10 pairs of terrific underwear sitting in my drawer while I waited for someone's birthday to come around. But the truth is I could not wait to see the look on a good friend of mine's face when he'd open up a three-pack of multicolored briefs. I felt like I wanted to explode!
The awkward silence will only last a few seconds, but those briefs will last for years. Believe me, you'll be thanked like you've never been thanked before.
Yet some people still don't get it. They seem to forget that we're all grown-ups here, and we are perfectly capable of accepting a simple jalapeño-pepper-themed pair of underpants from a friend we've known for 15 years without getting all bent out of shape. They get high and mighty and threaten you physically. But underwear makes a great gift! Fact: The Playboy boxers I got for Pete got everybody talking much more than the $250 certificate to that fancy downtown restaurant all the other guys chipped in for.
The best time to give someone a fun pair of undies is anytime. Whether your friend just got fired or you're all out for a night on the town. Nothing adds to the fun like a tiger-stripe bikini-brief that cups your balls just right, or a banana thong you found on sale at that little bookstore off the interstate. At my last job, they told me it was inappropriate to do that. I said, "Just lighten up and try these on!"
We're not living in the 1950s, people!
If you find a pair of underwear that you like a lot, the kind that gives you the support you need without squeezing your dick, pick up a couple extra pairs in all sizes. Spread them around—it wouldn't be fair to keep them to yourself. And when you hand them out, make sure to describe how they feel against your skin. You'll be doing everyone a favor.
In order to live a little, you should give a little! And there's nothing like the look and feel of a fur jockstrap to really live. It's funny like a novelty present, but it's also practical and sexy. It's every adult's right to feel sexy, and it's every friend's duty to help him feel that way.
And while he's feeling sexy, there's nothing wrong with putting your finger up his ass a little. Then a little more, until it's buried up to the knuckle. Prostate massages are just part of being friends. Give it a try! You won't be sorry.