Firstly - what saddle are you using? Saddles are a very personal thing and so you may need to go sit on a few to get an idea of what's best for you. I've got a Charge Spoon, and all the lads I go riding with reckon it's a razor blade, but for me it's more comfortable than the WTB's that they swear by.
Secondly - how long have you been riding? No matter what you wear/sit on the first month is gonna be a sore one. Your body has to get used to it I'm afraid.
Finally - the shorts. Get some proper padded gel cycling shorts. They don't have to be the skinny lycra, but so long as they're proper cycling shorts you're onto a winner. Remember that you don't wear underwear with them because the seams are in difference places to stop you getting cut in half.
To be honest I buy all my biking wear from Aldi when they have the specials on. Ok it's not branded, but it's just as good as the posh stuff, you don't care if it gets ruined and it's really cheap. I got waterproofs, glasses, gloves, shorts, normal tops and underwear for 50 quid. That wouldn't buy you a jacket!