New and seeking advice

When measuring a sub for a chastity cage it is good practice to take measurements from the body where the penis starts to the end when as small as possible So the full length of the shrunken penis (top) to (end) mine is 7cm total length when soft measured many times as the penis shrinks and grows. Then you would select a cage at least 10cm shorter than the minimum you have measured so for me the Total cage including the base ring end - end is 6cm.
Next you need to measure the base ring and this is the most tricky to get correct first off as its not just a straight measurement as most can tolerate a quite tight base ring. We tried a few cheap Chinese designs first to see what base ring but mine is Oval 36x40mm and works well for me.
After many years of testing these are my final measurements for a 7cm penis.
The urethral insert makes getting back in if you ever manage to pull out impossible at least for me.

Hope this gives you food for thought.

Mitch

 

All best wishes. Your situation is not quite the norm for here as you are effectively both Dominant and sub at the same time, though to different people. Not that common, but there are some other relationships like yours. There are others on FL. CM did till a few days ago have an F section called 'The Secret Garden' for current/wannabe F lockees, though it wasn't much used/visited and its threads have now been subsumed in 'Other Fetishes' as part of the reorganization. But you and your Mistress might like to look round there to see if there's anything suitable for you both.

 

Just a quick comment on "corner time in a long pencil skirt and stilettos", here are a few variations I use.
Get a small board, like a deck board maybe an inch thick by a foot long.
Have the sissy stand with only her heels on it. This will "jack her up" another inch or so adding to the discomfort and awkwardness. Also the 1 foot length requires her to keep her feet close together and not move them, also adding to the stress.
Have her kneel and kick her toes into the floor for a minute or 2 first. This will tenderize her toes and make standing in her stilettos more painful.
Instead of placing her heels on the board, have her stand with only the balls of her feet on the board so her heels cannot touch the ground. her feet will be straining in no time.
I promise you, all of these are very effective.