Hellraiser
Arcane
I can't remember the last time I built wriggles on nasus. Even if you start cloth+5 (which you do most of the time anyway) you just keep the cloth to turn it into FH later on. The thing with nasus is that he is a very late game champion, you can't just get fed and buy shit to win you need to farm farm and farm. Items help but they won't mean jack if you have 50 CS and only around +100 Q damage farmed. Which is why you max Q first, you need to minimize any CS loss from last hitting too early every minions is worth 3 points of damage. That doesn't sound like much but it quickly adds up. W is the second skill you max, it is a godlike debuff that outright cripples a lot of champs (derpamere for example). It allows you to farm safely, mess up enemy gank attempts and prevent the enemy from trying to harass you. Nasus post 6 is ungankable unless you push a lot and don't ward. Even pre-6 he's hard to gank and due to lack of CDR that early odds are the enemy will push more than him since you try to farm with Q only as much as possible.
Overall you should build nasus with CDR items and tanky items, the only damage item you should ever get is a trinity force and you only get that after FH+shurelia's+FoN(or just a negatron if it is sufficient). FH is pretty much core on him but it should be delayed if the enemy (particularly your lane opponent if you face kenen or morde) has an abundance of magic damage. The reasons why you build CDR and tanky are simple, nasus scaling with raw AD and AS is meh and most of his damage comes from Q. This means two thing, one you need cdr to spam Q more (not to mention W) to deal massive damage, two you can build full tank and still rape. But I guess you already know that.
As far as nasus' counters go a good tryndamere can set you behind in cs by a decent amount early on but post boots and chainmail you can laugh at him, garen is just fucking obnoxious as is udyr. Irelia can be a pain because of W, morde is a major dick to lane against. Overall as far as laning goes your job is to be careful as fuck until level 2, slightly less careful as fuck until level 6, and not giving a damn about the enemy harass after level 6 and your first major tanky item (hopefully a glacial shroud).
If you want to learn how to lane against all champs (even if you shouldn't against some of them like Garen) check out this guide. It has a a list of what to start with and what to rush when facing different champs. It's very well written because FYA Umashi unlike that asshole Dyrus (fuck his shitty guides) actually bothers to write informative guides. Hyfe's guide is nowadays quite similar as far as the builds go (it got updated it used to be different hence Umashi mentions he disagrees with it but nowadays the builds suggested by both players are similar).
Overall you should build nasus with CDR items and tanky items, the only damage item you should ever get is a trinity force and you only get that after FH+shurelia's+FoN(or just a negatron if it is sufficient). FH is pretty much core on him but it should be delayed if the enemy (particularly your lane opponent if you face kenen or morde) has an abundance of magic damage. The reasons why you build CDR and tanky are simple, nasus scaling with raw AD and AS is meh and most of his damage comes from Q. This means two thing, one you need cdr to spam Q more (not to mention W) to deal massive damage, two you can build full tank and still rape. But I guess you already know that.
As far as nasus' counters go a good tryndamere can set you behind in cs by a decent amount early on but post boots and chainmail you can laugh at him, garen is just fucking obnoxious as is udyr. Irelia can be a pain because of W, morde is a major dick to lane against. Overall as far as laning goes your job is to be careful as fuck until level 2, slightly less careful as fuck until level 6, and not giving a damn about the enemy harass after level 6 and your first major tanky item (hopefully a glacial shroud).
If you want to learn how to lane against all champs (even if you shouldn't against some of them like Garen) check out this guide. It has a a list of what to start with and what to rush when facing different champs. It's very well written because FYA Umashi unlike that asshole Dyrus (fuck his shitty guides) actually bothers to write informative guides. Hyfe's guide is nowadays quite similar as far as the builds go (it got updated it used to be different hence Umashi mentions he disagrees with it but nowadays the builds suggested by both players are similar).