lol I laughed so hard when I read that!
First of all, we are talking about either dating or relating with a woman to the point where the pants are gonna come off. If you are in a situation where you may have sex, it is best to be in the proper attire for me. If you know you aren't doffing your slacks, then it doesn't matter what you wear.
But we are talking the stripping game. And the Prime Rule is this... NO TIGHTY WHITIES!! I can't emphasize it ENOUGH! In addition, while colored tighties are not as bad, they still have that diaper look which really detract from the otherwise masculine appearance.
Now, if you are a guy who has a large paunch, then boxers are best. Mid-length boxers, either silk or dark cotton, with a fly that is not gaping, though only one snap at the waist.
Finally, if you are fit or at least have no or little body fat, then boxer briefs are the absolute best. Darker colors are usually better, mainly because they camouflage the "precum" or other bodacious liquids that may seep. I DO assume you washed your ass COMPLETELY beforehand, and I mean COMPLETELY, and there is ABSOLUTELY NO DISCOLORATION in the rear. And yes, women will know from twenty feet.
As someone who was both 40 lbs overweight at one time, and now currently fit and physically active, I can attest to this from both angles. I would invest in "formal" boxers or boxer-briefs for dates, spending more for high-quality silk or other such material. In addition, the same care must be given for socks, undershirts, and even thermal underwear if in super-cold weather areas.
EDIT: Oh, one more thing... do NOT GO COMMANDO! It may seem cool to unzip right to the Johnson, but women have an innate sense of hygiene which they will remember. And, frankly, it's not all that comfortable for "the boys."
I cannot go commando, it feels weird. Boxers for me.
Today I went with.....high cut white panties!
Commando? No way. I hate the slapping my balls get against my thighs, boxers aren't any better and both chaff me. Boxer briefs stfetch and bag out after a few washes. Tightys squeeze my junk against me. Because I have big balls and more than most guys, I get what I want in a jock: jock brief for regular wear in my size, and one size smaller when I play rugby. Thanks to Nutty Buddy, I finally have a cup that fits.
Would trade them all in a minute for something considered "average."
Unless it's very cold outside or I'm going to the gym, I go commando. I never quite understood the point of underwear and have (on more than one occasion) benefited from not having any on. Apparently some women find it quite sexy.
Boxer Briefs or just boxers for me. The main thing is keeping my manhood centered 'cause sometimes it shows through my pants and I'm not one/too shy for showing off the goods.
Sometimes boxers. Sometimes briefs. I've been tending towards boxers a bit more frequently lately. It just feels right.
Sexual innuendo? I can keep it up all night.
depends on what I am doing. If I am at work then its boxer briefs. If I am any other place else its a thong
Boxer Briefs are the superior cut for sure!
Click The Pic
I wear boxers and briefs so
Jockey Y-front classic briefs, Slip briefs (mini or midi), Tangas, sometimes Thongs but less and less boxers these day's.
usually boxers. some times briefs
Boxer briefs mainly, though I do have several thongs and some tight bikinis. Very comfy.