Thursday, September 26th, 2013

My girlfriends don’t seem to understand the concept of briefs. As in the underwear. I think they look at them as a “gay” thing, and so any guy who wears them is automatically unfit for them to date or sleep with. I don’t really get it. But then I am a gay man. Who does wear briefs.

Just the other night at kickball we were talking about men’s underwear. Not an uncommon topic for us, actually. The girls on my team are fascinated by what I wear. And I’m always more than willing to pull down my shorts to let them get a peek. (It’s a very heterosexual bar – it’s kickball, after all – so no need for you to retroactively worry.)

I wish you had seen their confusion the few times I wore a jock strap. It’s like they’ve never seen backless underwear before. And I kept trying to tell them that it’s the same basic principle as their thongs, but they still don’t get it. Even after I pulled down my shorts to let them glimpse my ass cheeks and see the jock strap working in real life. They’re hopeless.

Personally, I find jock straps super comfortable. They hold everything in nice and securely, they minimize unwanted package protrusion and they keep my butt comfortable and cool in the summer. Not to mention the slight lifting effect they have on the ass. It’s always nice and perky when I’ve got one on. I bought my first pair when I was dating you. And my second. I stopped after two, though. Because really, how many pairs does one man need? It’s not like I play professional sports or anything. And now that I’m running a lot, I need a boxer brief or my thighs chafe.

But back to my girlfriend’s not understanding briefs. Kristen and I were talking about underwear the other night at kickball and she was asking me what I liked to wear, and I told her briefs. She seemed somewhat confused by this. But whatever. She’s probably never seen a guy in briefs, except for me. Then Dhani, my Indian (like the sub-continent) girl friend, comes up to join in our conversation. And she asks maybe the most baffling question ever.

Wait…so when you wear briefs, where does you dick go? Do you have to tuck it up?


I couldn’t even process her question. Where else would we put it? And do girls really think that it’s more comfortable having our penises dangling down between our legs? Or tucked into one or the other pant leg? Because it’s not. It’s just annoying. And requires constant readjustment. The brief keeps it nice and pulled up. Not “tucked” as Dhani put it. That’s what drag queens do to hide their penises. And they’re tucking them in the opposite and far less comfortable direction.

I thought that maybe this lack of knowledge about men’s underwear (particularly a gay man’s underwear) held just for the girls on my kickball team. But then the conversation came up again with two of my roommates, Marjorie and Trina. We were talking about the guys Marjorie has been going out on dates with and what she likes about each one. Somehow we got on the topic of underwear and again I was baffled by Marjorie and Trina’s preferences. They both agreed that boxers were a no-no. But they also weren’t attracted to a guy in briefs. Only boxer briefs for them.

Again, I don’t understand. It’s not like I’m talking about tighty-whities. Briefs are form-fitting and colorful. They can have patterns and come in low-cut varieties. They are super sexy. And yet again, I’m confronted with girl friends who don’t agree.

Poor straight guys, relegated to wear only boxer briefs. That must get annoying. I’d want to be able to mix it up, have a little fun with it, and get the phallic support I need. Boxer briefs, despite what people might tell you, aren’t always snug down there. They can stretch and sag, and then they’re doing about as much good as a pair of boxer shorts in regards to support. Not to mention how ugly they look on someone when they’re all loose and stretched out. But that’s what my girl friends (and I’m including all of them here) want their guys to wear.

Boxer briefs…

And if not boxer briefs, then they’d actually prefer their men wear boxers. Am I crazy? A guy wearing boxers as underwear just doesn’t do a damn thing for me. It does not cut it at all.

I mean, I’m not knocking boxers completely. I do own a few pairs. Mine just aren’t in the best shape any longer. They’re old and ratty, remnants of my “straight” days in high school and college.  Half of them have holes in them. I haven’t bought a new pair in probably six or seven years. I only wear them when I sleep alone, though. So you never saw me in a pair. No one sees me in them actually.

I saw you in a pair of boxers one time. A nice salmon-striped pair. I think they were from J Crew. Yours were fitted nicely though, almost as if you’d had them tailored. (I wonder if rich people get their underwear tailored. Because that would be awesome! Another reason to have a lot of money.) You looked cute in those boxers. But then you looked damn good no matter what underwear you had on.

I’m going to miss seeing you in your underwear. First, because you really do have an excellent ass. And then you have a little waist for someone who’s so muscular, so you can fit into all those sexy little pairs of briefs and the occasional jock strap.

I remember your different pairs of underwear pretty well, actually. There were those camo boxer briefs; the funky, purple and pink plaid boxer briefs; the bright blue and incandescent pink American Apparel briefs that you bought on sale with me that one time; your sexy blue, see-through mesh briefs; the navy pinstriped briefs that looked like something you might wear to the office if suits had never been invented; the colorful assortment of American Eagle boxer briefs you have from your college days of working there, the ones with the eagle logo splashed across the right hip like a bad paint job; and then that super sexy pair from AussieBum that was so small but just managed to cover you up.

(Are you creeped out that I remember so much? I guess I kind of have a fetish for guys and their underwear.)

But of all the pairs you had, do you know which one was my favorite? You might be surprised.

You had this pair of light blue trunks (they weren’t necessarily briefs, but then they weren’t as long as boxer briefs either) that had little yellow shapes on them that I think were ducks. I say I think they were ducks because it was one of your older pairs and the fabric had worn from so many wears and washings. But that pair of underwear was so soft and clung to your ass so nicely…I honestly never found you sexier than when you wore them, keeping in mind that one of my favorite parts was getting to take them off of you.

I just hope that the next guy has your ass. Or at least your eye for undergarment style. Because you really did know how to wear a good pair of briefs.


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