I'm looking to sell a couple of TF2 keys for real life money

Put a post on ST, trust me you'll get a ton of offers :P

Make it a requirement to comment on your thread before adding you though, and only trade with those with a decent amount of positve rep, and no negative.

You'll probably get a lot of adds from people with no rep though, I know I did when I sold off my keys.

That was a thrilling tale.

Try TF2OP

did you know this friend from real life?
as I read your tale my first impression was someone scammed those keys or something he sold then for those keys and wanted to get rid of them asap.
You know normal tf2player don't have huge amounts of keys since they don't drop ingame and can only be aquirred in mann co shop with real money or from community market.
If I were you I wouldnt have touched those keys, the whole story sounds a little bit fishy.

sourceop forum is the best place to trade large amount of keys in bulks but the people over there most of the time require some +reps and dont want to do business with people without reputation.

As for steamtrades, it's good enough, too. Propably your prices aren't right, just check the price other people are selling for, to see how much you can ask for.

another thing you could try is selling the keys on the market then offer steam wallet for paypal

like you buy games/items for people and they paypal you back; but obviously at a discount (usually around 10-15%--although I havent traded in a while)