sounds like your headphone clamp is too tight as opposed to a lack of cushioning, if anything. Currently wearing a pair of akg 612's with my glasses and there's no pain or anything like that (although sometimes if I turn my head my glasses make a creaking sound. not often though and I personally don't find it annoying)

It should depend based on your ears and how big your glasses are but something like Beyers or nice Sennheisers with nice pads and that aren't too heavy would work well. Don't have glasses myself so can't say too much but i do know that beyers and higher end sennheisers have really comfy pads and pretty good sound signatures as well. Also worth considering your budget/music preferences.
Might want to check out headfi, tons if information there on most headphones

Audio Technica ATH-ad700s are seriously comfortable. I wear them with fairly chunky glasses and I don't find it to be a problem.

http://www.head-fi.org/products/audio-technica-ath-ad700

logitech g430s are good

Sennheiser 555 595 598 600 650 700 800

beyerdynamic dt880 prems are comfy with glasses

good headphones, just some of them (600/650/700/800) are very source dependent.

I use dt880 prem's, but pretty much anything DT880/990 will work from beyerdynamic. Just shy away from the pros; they have extra clamping force. I use DT880s. Great w/my glasses.

Depends a bit on how much you want to spend. Above a certain pricepoint comfort (proper pads and no excessive clamp force) is pretty much standard for any decent brand (that excludes the usual suspects like beats).

Generally full-size (circumaural) headphones should be most comfortable with glasses. Thicker/softer pads and glasses with smaller frame (though you probably won't change that) -> more comfortable.

What are your current headphones?

I have akg q701's and theyre pretty comfortable with glasses on. My head is also larger than average I'd say? I'm a pretty tall guy so I'm just going to assume it is. Anyways, I don't have any issues with the q701's. It also helps that the velour pads that comes with the headphones are a major upgrade from the pleather ones from my previous headphones.

I'm fairly sure these are the glasses frames I have. Just to give you an idea of how big my frames are if that helps at all.
http://images10.newegg.com/NeweggImage/ProductImageCompressAll300/A1UX_1_201305301677251778.jpg

I can't speak for any of the other headphones listed in the thread but my 2cents on the g430s are that they're way too heavy if they're anything like the older g35's.

I have a pair of steelseries siberia v1 and they are pretty comfy for long periods of gaming when wearing glasses, hope this works for you too!

steelseries siberia v2 frost blue here, might not have the best sound quality if you're after that too (in which case get audio technica or sennheiser) but they're very comfortable for long periods of times, even with my glasses on

my wireless sennheiser RS 120 II arguably has better sound quality (though its nots that noticeable, to me at least), but it's honestly not as comfortable, especially with glasses on

edit : fuck

My Sennheiser HD 558 doesn't irritate me with my glasses.

IEMs work with glasses :p

I have Superlux HD668Bs and they don't hurt me when I am wearing my glasses. Just find a light pair with a good amount of padding :3