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.

Here’s what my Steelheart looks like in this pair of briefs:

Here’s an alternate head-on view.

As you can see, the pouch is quite deep. Slipping my balls and the tube down there results in a very comforting sensation not unlike putting on a pair of well-fitting gloves. Just as with the thong, there’s a bit of support, but not so much that I feel like I’m being pushed around excessively. I now own several pairs of these and they’ve become my default underwear while sporting the device (which is pretty much all the time).

The only downside to them is when I’m not packing steel. As you can see in the image below, even with the Steelheart Short’s tube in place, I can’t fill out the pouch. When swinging freely, these underwear do a good job making the penis look fairly unimpressive. They don’t get really filled out unless I’m sporting a healthy chubby (as is the model in the comparison, I suspect, besides having the ministrations of the off-camera stylist who’s pinned/taped things just so).

Though, on the plus side of the downside, they are the first underwear I’ve owned through which it’s entirely possible to masturbate.

They’re not excessively expensive when compared to other fashion underwear and their build quality seems quite high. The first pairs I got are probably at least six months old now and show little sign of wear. They’re holding up quite nicely. In my opinion, the John Sievers natural pouch briefs are the best best chastity underwear you can buy.

4 Replies to “The best chastity underwear”

  1. I find that I enjoy freeballing when I’m not locked up (and I used to freeball all the time before my husband and I started playing with chastity), but when i’m locked up, it’s terribly uncomfortable, and I end up wearing briefs. (Plus, freeballing when locked up, unless I tape the lock down, means I click whenever I walk – which I’m paranoid is a giveaway even though I’m pretty sure that anyone who could figure out what it meant would be into chastity anyway).

  2. I struggle to find the right underwear. I have difficulty with the seam down the centre of the pouch. It catches the tip of the urethra poking out of my cage. As I’m uncut, the edge of the glans is sensitive to rubbing also.

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