My strategy for learning how to sit like this was for meditation as I fully lacked better sitting positions, I personally found it very comfortable until my muscles and body screamed at me. MY default sitting positions and lack of crouching for extended periods result in this position to be heavily difficult for me.
My strategy was to do the following:
- Get a seiza sitting position setup. I have an office chair that I put around 6-7 inches of cushion on, namely a thick blanket and a bed pillow, the blanket being folded up.
Sit in the Seiza position for as long as you can, then change on sitting on your rear with both legs still bent, however is most comfortable. I swap between these two and while in the normal-for-me sitting position (not seiza) I tend to also flex my toes or fidget my knee up and down with my feet.
My plan is to get to a point where I can keep the position comfortably for an entire straight hour and only then will I begin to slide my feet forward and assume a more-stretched position for my ankles.
As someone who used to stretch their arms behind their head very regularly and eventually go to a point where for half my life I can touch my brain stem with my own elbow without using my other arm (can lick the elbow's tip with help from my other arm) this is more or less the best option.
Comfortable seiza sitting requires that you build flexibility, and if you can't assume the position even slightly yet, the next point will be what you can do.
- Things you can do, all will help, do them as much as you can manage.
A. Walk on your tiptoes like you're pretending your feet are hooves and you're a minotaur (maze and murder excluded).
B. When stretching your leg so your foot touches or gets close to your rear, hold that position for 20 seconds at a time and do those repeatedly (I say 3 times) 20 seconds apart.
C. Hold a squatting position with your thighs and calves touching, lean forward if you have to. You are on tiptoes with this one.
D. Assume a situp position, something used to weigh your feet down as if you were going to do situps as if you couldn't keep your feet on the floor. Legs bent and feet outstretched as much as you can manage.
The great thing about building flexibility is that downtime from attempts are more important than the stretching. As a kid, the above arm stretching mentioned prior was only performed maybe 2-3 times per day for maybe 10 seconds straight, I simply touched my arm to its jointed-shoulder and stretched it backwards and did this repeatedly for weeks. Eventually my arm became flexibile enough that I've never needed backscratchers.
You are building flexibility more than anything else and for that, taking it slow and easy is important. Your exercises are ultimately all stretches and as such it will take time.
There is no shortcut to building flexibility and becoming more comfortable in the seiza sitting position outside of simply integrating different forms of the sitting position into your daily life, you're stretching your feet, ankle and lower calf as those parts feel the worst when trying it
Note: If you also have problems with your knees hurting when trying this, stretch it out straight, either sitting or standing, and tense your knee for 10 seconds, relax it for 10, tense for 10 and repeat this tense-relax loop 10 times, it will strengthen your knees and reduce the likelihood of such pain.
Goodluck!