About 14,000 years ago, I wrote a post about the best underwear for chastity. I figure it’s time to update and expand that entry.
I have a serious thing for underwear. It drives Belle nuts because I have far more pairs than any normal person needs (I mean, seriously, nobody really needs more than 10 pairs or so). I haven’t counted in the same way an alcoholic or nicotine addict doesn’t count, but it’s a lot of pairs.
I just keep buying underwear. I’m a total sucker for it. And now Instagram knows and keeps showing me ads for more. Not to mention I belong to the Underwear Expert club so I get pairs automatically sent to me from them. Hey, the first step is admitting I have a problem. Right?
I say all this (and have added so many photos I’ve posted to Instagram and Twitter) to drive home the point that I wear a lot of fucking underwear and know from which I speak on the subject.
Those who have come to chastity relatively recently might think the best underwear for chastity wearers is the tightest. The pairs that smoosh everything down as much as possible and make the whole package as featureless and inert as possible. I, however, am here to tell you life is too short for that shit. Sure, you’ll maybe hide the fact you’ve got something interesting between your legs, but you’ll suffer for it and, by the end of the day, will be in a lot of pain. It’s just not worth it. You have nothing to be ashamed of, my friend.
My idea of a perfect pair of underwear is one that provides some support for the device so that it doesn’t hang in such a way as to put too much stress on one’s balls but not so much it squishes or flattens or pushes the device into one’s body. That fine line of offering support but also allowing freedom of movement. Note I am almost always in the Steelheart (a metal device with a moderately prominent tube) so guys in plastic or micro devices will have different needs.
All that said, my previous best underwear was the John Sievers “natural pouch” pairs. I still have several of them and they’re still excellent options. They have a roomy, generous pouch and are very high quality.
Another brand I’ve recently become acquainted with is Ergowear. They also have an “ergonomic” pouch and a wide variety of styles and colors. I’ve had a pair of boxer briefs from them for a while and recently expanded my collection to include these which are probably my favorite pair of underwear from a comfort point of view.
The pouch is massive and there’s essentially no waistband but the whole things still works. I’m not crazy about the length of the inseam and will probably try the shorter boxer briefs next time or the bikinis.
For the record, here’s the first pair of theirs I wore.
I do have a few gripes about Ergowear. I placed an order from them that took so long to arrive I had forgotten I placed it. Also, one of the pairs I received seemed to be sized appropriately in the waist but was two sizes too small in the leg openings. So, service and quality are not marked very high, I’m afraid.
The other recent entrant I’m pretty happy with is Cocksox. They have three pouch styles. Original is the roomiest, contour is slightly less so, and snug is exactly what it sounds like. I have only worn original-cut pairs. The thing I really like about Cocksox is their more adventurous colors and styles.
These briefs are just so fucking awesome. Kind of lacy, but not at all feminine (not that there’s anything wrong with that), with a roomy supportive pouch. Love the red accent color.
While this thong is totally hot and my current favorite in that style.
Heavens. I love Cocksox. I just wish they had more options in their original pouch.
The biggest problem with all these roomy-pouched underwear is those times I’m not in chastity and wear them. They make the penis seem particularly insignificant since it barely makes a dent in filling all that space. But…who am I kidding. I’m rarely not in some kind of chastity.
Of course, I wear more than just these brands and I don’t only wear big, roomy pouches. I have underwear of all kinds and some I wear because I love the color or fit even though I know the chastity aspect is lacking. C-In2 is like that. I love love love their styles and fabrics, but their pouches are just acceptable to too tight. At the end of the day, underwear choices have to be about more than just practicality. But if you’re in a device not too unlike mine and are wanting the best combination of style and function, I recommend Seivers, Ergowear, and Cocksox.
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