For getting a permanent wedgie that doesn't become too uncomfortable because of pressure, try a permanent wedgie that changes between completely loose and quite tight throughout the day. Try:
Idea 1: Tie a rope from the back of your underwear, over your shoulder, and tie the other end to your knee. Tighten as necessary. Add a polyethylene bag or something on your shoulder under the rope so it can slide easily. That way, the rope is tightly pulling on your underwear whenever you are standing/lying down, and loose when you are sitting.
More general ideas:
Idea 2: Try a shoulder wedgie with bigger underwear (try a big, nylon thong).
Idea 3: Try a weaker permanent wedgie.
Idea 4: Try taking breaks. For example, you could undo the wedgie for 5 minutes every half hour.
Idea 5: Stop the wedgie and completely pick the underwear out of your ass. This lets you rest. You will also find that putting a permanent wedgie back on from neutral is quite satisfying.
Idea 6: (Male) Don't let your underwear crush your nuts (male) for too long or you will feel sick. Potentially try keeping a set of underwear with the crotch cut out for this purpose.
Idea 7: (Female) Avoid letting your underwear dry out your vagina (female). This will damage your labia and chafe you way faster.
Idea 8: For reducing chafing, try to wear big, thin underwear under your main wedgie underwear. The main idea is to reduce cloth-skin rubbing without weakening the wedgie feeling too much (by having a thinner buffer layer). You want the under layer to always catch the cloth from the wedgied underwear. You could try wearing thin panties or something under a thong, then pull on the thong.
Let me know if this works.
Likes: Thong | Shoulder wedgie | Chair wedgie | Wedgies from girlfriend | Creative dares.