Best underwear for guys in chastity

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?

The underwear drawer is bursting.

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.

Panty problems

This whole panty thing got kind of out of control. After reading the post about it, Belle related to me that the idea didn’t do anything for her. That’s fine, if a little disappointing. Totally out of left field and, truth be told, it’s not like wearing something like that is a core part of my sexuality or anything. I’m just experimenting. But then she made a point of saying, “I’m not interested in ever seeing you wearing them.”

That made me feel weird and awkward and sat between us like a dead fish for several days. Suddenly, I was embarrassed and worried she’d even see them in my drawer. I was afraid of being judged and found to be somehow wrong. Then, after a negative comment from a follower to a quickly posted image on Twitter, I spiralled into a very foul mood and impulsively deleted the tweet. It’s one thing to hear something like that from your partner. It’s something quite a bit different to be pantie-shamed by a fellow anonymous perv on the internet.

In any event, Belle’s intention wasn’t to be harsh. I could tell by the tone of how she said what she said. It was an honest comment and I’m glad she made it, even though it pained me. My response was also honest, but I wasn’t mad at her for feeling how she feels and I’d rather she not take it back or try to gloss over it or anything. We’ve discussed it and, after, I’m in a better place if only because the issue is out there. It’s not resolved because I don’t know that it can be.

It was surprising to me how quickly my ego destabilized from this little adventure. I’ve been on pretty good ground for a while and haven’t felt the “freakish freaky freak” thing in a long time.  Then, BOOM, there it was. In any event, like I said, we’re past the worst of it and I’m feeling somewhat better now. I still don’t think I could let myself be seen by her in them, though she said incidental observation (like when I was changing for bed or something) wouldn’t bother her. It’s still a tender spot. At least I can bring myself to put them on without feeling self-loathing.

Practically speaking, I’ve worn two pairs now for a day each. I find I like the boy brief cut better than the thong cut (I also got these but haven’t worn them yet). I don’t have a general problem with thong-style underwear and have several pairs. They’re really good for achieving that commando feel while still providing a bit of support for the steel. I think what I like about the boy brief panties is that I could feel the lace on my ass under my jeans. I was often reminded that I was wearing them and that was satisfying. The other styles look good on, but are just like any other underwear once covered by pants. I also like the incredible lightness of lace. They’re there but just barely. A very appealing material for me. I’m wearing the briefs again today without a device because I’m going to an event tonight where there’ll be metal detectors. I was worried the lace would rub uncomfortably over the penis (which is often very sensitive to that kind of thing right after getting out following a long time locked-up), but there’s been no issues so far. I will be posting HNT this Thursday of what that looked like this morning, so beware all panty-hating types (and Belle).

I’m still trying to figure out the appeal in general of panties. I think it’s that I’ve always had a thing for sexy underwear most men wouldn’t wear (a fetish?) and these are just an extreme example of that. There’s no doubt when you see them that these are for men because they have ample pouches cut into them. I don’t feel like I’m wearing women’s underwear at all and still have no desire to do so. But I do like the lacy stuff and more feminine look of these. Weird.

In any event, I’ve picked up two more pairs. A pair of red (because that’s all they had) shorts and a pair of tanga briefs (a cut I’ve never heard of before). We’ll see how those go.


I have kind of a well-known thing for underwear. I like ’em colorful and skimpy and even sometimes sheer and see-through. So I guess it shouldn’t be a surprise I also have a thing for lacy stuff. But surprised I am.

This is one of those brain twisting sexual self-discoveries. At least I assume it’s sexual. See, I squick out over sissies. Hard. And the idea of wearing women’s clothing and makeup and stuff does nothing for me. But I just discovered that underwear designed for men using materials and cuts typically used in women’s underwear is…OK. More than OK. Like, distractingly hot. Like, I couldn’t fall asleep last night, it was so hot.

The thing I struggle with right now is that this clothing, which I think of as men’s because it’s got pouches in the crotch, is shown on fucking hot obviously male models, etc., is sold on a site for cross-dressers. And…I’m like…gah! And not the good “gah.” I mean, of course. The underwear looks like panties so why shouldn’t they call them that? And really, isn’t that part of why I like them? I have a black sheer thong I occasionally wear (like today, duh) and if someone were doing our laundry I’m quite sure they’d put it in Belle’s drawer by default. What man would wear such things? It’s a very naughty feeling knowing I’m wearing outrageous underwear over my locked steel chastity device (even the fucking device falls into this secret naughtiness category, if I think about it). Having underwear (panties) that are all lacy and see-through or with a frilly fringe or a ruffled bottom is just…fucking sexy as holy hellfire.

So I bought some. Three pair. (With my allowance, not Belle’s money.) And I’m like…what the fuck?

I have limits. Some of their offerings I am definitely not interested in (but, you know, if it works for you, go for it). Others are…intriguing. Weirdly and oddly. But there it is.

So I don’t know what this means. I don’t know what this makes me (or that it even matters). I don’t know how Belle will react (I hope well). But I do know I want my frilly panties to get here ASAP. That, I know for sure.

The best chastity underwear

Note: I’ve since published an updated and expanded list of recommendations with lots more pictures of yours truly in his skivvies. 

Underwear can be tricky. Some guys wearing trapped ball devices eschew it entirely, though I find that leaving the device totally unsupported will eventually cause sore spots, especially in a heavier steel device like the Steelheart. For the rest of us, picking the right pair is a balance between stealth and comfort.

The stealthiest underwear compresses everything down and as flat to the body as possible (think about any pair of tighty whities you’ve ever worn – something like this). Necessary for certain situations and for short periods, but life’s too short to come home every day with aching wobbly bits. I’ve found that the most comfortable underwear type is something like the N2N G-string. I have several pairs of these and they provide the bare minimum of support necessary to ensure the weight of the device isn’t being fully borne by genitalia. On the other hand, their generous pouch and stretchy strings do almost nothing to hide the tube. It’s almost like going commando, so I typically reserve their use for when I’m wearing baggier pants (or feel like putting on a show).

After much trial and error, I’ve found what I think is the best balance for those wearing a device like mine. They’re the line of “natural pouch” briefs by John Sievers. They provide a modest amount of stealth while not squashing anything. After the jump, you’ll find some NSFW images and more info.

Continue reading “The best chastity underwear”

HNThumper XIV

Underwear is a tricky thing. If you’re trying to hide the odd bulge in your crotch because the pants you’re wearing are especially “showy”, then I’ve found tight briefs to be the best bet. However, I’ve also found that the better a pair of underwear hide the device, the more uncomfortable they are. Holding the device down between your legs, squashing the balls into the tube, etc., can leave you feeling rather abused by the end of the day.

If you’re looking for maximum comfort, then I’ve found a simple string thong to be best. The pouch supports your package just enough but doesn’t push it around. Of course, the trade off is that it does nearly nothing to hide the device (it’s almost like going commando, which I’m not a big fan of in chastity), but the difference in comfort is noticeable at the end of the day.

This discussion, of course, is all a flimsy artifice to give me an excuse to post a picture of me in my underwear. Click the jump for the moderately NSFW image (and then click again for a slightly more risque reveal).

Continue reading “HNThumper XIV”