Does this picture mean I need a longer cage?

Depends on what you want, penises are pretty squishy so you'll likely fit. Personally I think the best device for long term wear is one that's has an open design to help keep things clean and slightly shorter (1/4" - 1/2") than your normally flaccid penis. I know that super short devices are all the rage and I have couple myself but I don't think that having your skin bunched up for days on end is a great idea, although I've found that the shorter the device, the better I sleep.

 

For me, i enjoy different fits on different days. So i don’t think it is so much a question of “should”. Rather, you probably would enjoy having two cages. Or three....

As a CK owner of several cages, i think you are making a good move to get a bigger one.

 

No, but you might want a larger cage diameter if you want to pack everything in.

 

Exactly this!

I've found very short devices look great, are very comfortable under clothes, and do a wonderful job a preventing erections, but they are a poor choice for 24/7/365 wear without frequent removal for cleaning and skincare (since the skin is too bunched up when wearing).

My 24/7/365 is an open construction SS device (jailbird) that doesn't ever need to be removed for cleaning. The key for me is the fit when absolutely 100% flaccid (think cold shower). Ideally there should be a little compression at the tip 1/2" to 1/4" is good), with as little bunched up skin as possible along the shaft. This lets everything stay dry and "aired out" and it allows all the skin to be cleaned in a shower/bath and then properly dried without removing the cage (i use a hairdryer and baby powder after showering).

If the cage is longer than me when completely flaccid, nocturnal erections will "ratchet" the cage away from my body (each erection attempt pushing it farther away before relaxing and pulling back farther in the cage). Having the tip pushed against the end of the cage prevents this.

 

You need to be in a small, steel device. Start with a stainless-steel Nub with a waist belt. All will stay in place until your HK decides when to unlock

 

@King Hippo this is spot on