It would depend on the plug. Some are comfy for long term wear, others have bases that press uncomfortably on the buttocks, chafe, or start to pull at sensitive skin. You don't want to be trying to figure out how to deal with this in the middle of a long date (though having a purse, bag, or briefcase would be a very good idea so you have somewhere to stash it if it needs to come out). Another consideration is lube - water-based can dry out, whereas oil or silicone can stain clothes. I'd think some kind of shield/guard for the clothing would be a good idea.
As far as the plug goes, look for a small yet secure base, long neck, and a noticeable bulge between the body and neck (all help to keep it in and unobtrusive).
I only use butt plugs during sex. I don't wear them out of the bed.
I don't think I could eat with a butt plug in anyway. They are pretty distracting. For me, they denote sexual arousal and I want to be able to enjoy my food without wanting to run out of the restaurant to get home and fuck immediately.
But, if you think it won't distract you or take away the pleasure of eating your food, give it a try.
I think this would be kin of sexy, maybe with a vibe too.
No, I really love going out to dinner and eating amazing food. I don't want to be distracted by something up my ass. Plus there is just too much that could go wrong, it's not really something that turns me on.
No, but I'm not interested in stretching my ass long term in any situation. A lot of people have leakage issues when they age as it is. I can't but help thinking wearing a plug for expended periods of time may lossen the ass???
Besides, I'm just not really into that constant full ass feeling - doesn't do much for me. When something is up my butt, I like it sliding in and out!