Chastity: Boxers or Briefs?

Posted: March 6, 2016 in Chastity, Fetish, Kinky, Long Term Chastity, Male Chastity, Mature Metal, Orgasm Denial, Queens Keep


It’s an age-old question, in practically all walks of life. Men all have their opinions of what feels the most comfortable to them, and women all have opinions of what they like to see on their man! So what kind of underwear do YOU prefer: Boxers or Briefs?

Through my teenage years and most of my adult life, personally I always tended to be a Boxers kind of guy. Keep everything loose, free, and able to “breathe!” But when it comes to wearing a chastity device, I can start to see the other side of it too! On one hand, boxers can make it a little bit easier to “reposition” the cage once in a while if it starts getting uncomfortable.  On the other hand though, the closeness and extra support of briefs, can make your chastity feel even more comfortable and secure!

So why not the best of both worlds? For me, I have really begun to prefer the simple Boxer Briefs! You get most of the look and some of the feel of boxers, combined with the tighter support of briefs. Since the weight of the Queen’s Keep isn’t just dangling there between my legs, they really are quite comfortable to wear!

And even more importantly, Angel thoroughly enjoys the way they look on me! She especially likes this solid red pair, which if I may say, does fit my form rather nicely!


These are great for everyday wear and even some fun, sexy times with Angel when I know there’s little chance that I will be getting unlocked anytime soon. But then, when things are REALLY starting to get hot and heavy, I’ve found that I can really send Angel over the edge by pulling on this pair of shiny black underwear with see-through mesh in all the right places!


She reacts to that visual in much the same way that I would imagine that I look like when I get to see HER all dolled up in some sexy lingerie!  For us at least, it goes both ways. We both have a lot of fun getting rather provocatively dressed for each other! 🙂


Now for a little “Better Know My Readers” survey…  Enjoy!

(please note that the male/female designation is not asking for what gender you may identify as, only if you prefer men’s or women’s types of underwear!)


Here are some “Other” responses that have been received so far, in case anybody would care to type in the same response to add to the tally!

  • Diapers
  • Men’s Thong
  • Pouch briefs
  • Panty girdle
  1. Iwan says:

    Normally good ‘ol men’s briefs are fine, but semi-transparant plastic briefs when I’m in the mood and want to feel horny. Just like regular briefs, but deliciouly uncomfortable: it gets hot and sweaty pretty quickly in there, constantly reminding me being chaste thus straining in the device to bursting. Nice side effect is that the briefs catch the precum I’m oozing in this state, with no one in my surroundings aware of my flustered state. Great as a warm-up to a release or a long tease session.

    Only just discovered the blog, it’s great, hope that I can follow your footsteps with my loved one.

  2. Robbie says:

    A lot of the time I am in a diaper and plastic panties. When I’m not I always wear, or rather I am ordered to wear, girls panties. Always nylon and either the full cut briefs or hipsters.

  3. sophiejc50 says:

    My wife makes me wear feminine underwear permanently.

  4. Travis says:

    I prefer jockstraps (Bike or Champion brand), and my girlfriend likes me to wear them. It’s part of playing a macho role, so for us there’s more thrills when she is sub-dude-ing me in male gear. Plus I’m a pretty big guy: 6’1″, 195, muscular. I can get to 9-1/2″ inches hard if she’ll let me. Sometimes, I’ll wear a male stripper thong (they have a bigger pouch), especially a really cheesy one (gold lame or leopard print). That’s fun, but it’s not underwear, per se. But it’s sort of a switch-up, plus I’ll entertain her with a dance. If I don’t wear a jockstrap, I go commando … which has it’s challenges. BTW, our device of choice is a simple tube that encloses the shaft of the penis but exposes the head (sometimes this is called a constrictor), but we also have a jailbird and birdcage for change-up. All metal, no plastic for us.

  5. Ted says:

    Andrew Christian makes Show it jockstraps with plenty of room for your cock cage. I prefer naked but when I am in pants at work theres less rubbing and wear on the pants fabric.

  6. vinnieh says:

    I prefer to wear boxers.

  7. Where did you get the see through boxers? I think my wife would love those!

  8. Domina Jen says:

    I’ve always been into humiliation, and using chastity as both a tool for control and a tool for humiliation. So making my boys wear women’s panties is my preference.

    But you have to be careful when going that route, because cages are big, bulky, and heavy, and need support.

    I love the way men look in women’s boyshorts. And the more plain ones can pass as men’s underwear for things like doctor’s appointments, locker rooms, etc.

  9. Fantastic post, thought provoking as always

  10. Lady Eiluj says:

    Love being able to see your device through the mesh on the black pair ……very sexy
    Lady E x

  11. I only wear boxer briefs or trunks when locked in MrsL Steelheart. When I am unlocked I opt for trunks or jocks.

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