Well, Cambridge has a portrait class, but it's on Mondays from 8-10. Yuck because of 8-10, and out because I'll likely be roleplaying on Mondays. Boston (a 5-minute walk from work) doesn't have a portrait class. Both of these places have Intermediate Photography, which would be better than nothing.
Brookline has a portrait class, and it's on Tuesdays from 7-9. Brookline is not terribly convenient though. Still, this sounds like the class I want, and getting home at 10 on Tuesdays wouldn't be that big of a deal. I'll see how I feel about it in a week or so and hope that the class isn't filled by then.