jockstrap or boxers?

Sweetman, It just depends on what you desire to do/accomplish. You are certainly equipped to model either.

Now if you desire to impress or shock someone during fore-play go for a styish Jock.
 
Think you could do with something like an army style trunk / boxer brief (Without sling support), bit like the ones in my profile from C-in2

A number can be found here: C-IN2 at MensUnderwearStore.com - athletics, eco-friendly, shirts, swimwear and underwear (Especaly recommend the bamboo range, especaly if you tend to sweat a bit).

Another good range in the same style would be 2(x)ist Men's Underwear by 2(x)ist at MensUnderwearStore.com

You certanaly have a good package there, and with the slightaly defind pouches in these 2 ranges, you would realy kick things off with looks.
 
Why not switch it up? Variety is the spice of life! I have all kinds of underwear, even though boxers are what I wear most the time. It's fairly inexpensive to buy a jock, some boxers, trunks, etc., and always makes for interesting fun to wear something different just for the hell of it.
 
i like jockstraps. are they comfortable?

Most are not at all comfortable for the well-endowed guy, at least until they are broken in. The old-fashioned ones are made of this horrible stiff fabric that tends to squash and compress the larger man.

If you want a roomier, more comfortable jock, I'd recommend Under Armour's model. They can be found in the Boston area (I'm also a local) at Modell's stores, or you can order them online from Sports Authority or Dick's. This is the most comfortable jockstrap I have *ever* worn ... well worth looking into.

Good luck!

Steve