Sounds like you're like me. Most underwear pouches are too small in front and too big everywhere else... But there are a few out there for guys like us.
Here're two. They're almost out of stock but I've seen them on Amazon, DHGate.com, & AliExpress.com
Cockcon Sexy Men Underwear Boxer Ice Silk Transparent Breathable thin | eBay
COCKCON Sexy men boys underwear briefs thin ice silk Low Waist comforatable | eBay
I'm wearing the briefs in my avatar.
There's also ergowear.com. They're a bit pricey but wear like iron. You want anything from the 'Max' line. Do not get 'Feel'!! They have some new pouches but I don't know about them. They have swimwear.
McKillop has different pouches. It souds like you'd best fit #5, aka 'bounce'. Also check anything with a 'hoist' pouch. Swimwear here as well. I haven't bought anything from them yet.
AliExpress.com has a lot of new underwear with pointy pouches. Search for 'elephant', and 'rhinocerous' men's underwear.
Cockrings: primalrings.com has an interesting design that keeps the swing of your dick and gives your balls a boost. For all cockrings it's important to measure first. If you're looking for all-day wear you want to be able to get two fingers through the ring while you're wearing it and you're soft.
Also, glans rings aka head rings weighing 50-60 grams are available on ebay for under $10.00. Wearing one or two will keep your dick at its max soft length. And the bounce it adds feels damn good, too. There're other threads about this.
Hope this helps.