I'm looking to break into the grade on lead but am a bit of a wuss. Ay suggestions are welcome.

Trad or sport?

Sorry, trad. Multi pitch is fine. I'll hop on 9/10 sport lines now.

Last pitch of Over the Hill in Eldo. Approach via Over and Out.

First pitch of Pony Express in Eldo.

nip n tuck crag, boulder canyon. Finger crack is the route.
short, secure and bomber gear the whole way.

blder cyn. cob rock, the empor. 5.8 the start is the worst gear. only about 10 or 15ft of easy climbing then plug away.

these were two of my first in the boulder area.
have fun.

Steppenwolf at Turkey Perch in the Platte
Yosemite Crack at Lumpy Ridge

Werk Supp is very moderate with a wide variety of placements. You could place 5 pieces or you could place 25. Just mind the first 10 ft or so. It was my first trad lead.

Actually Steppenwolf is a little sketchy at the top. I don't think it fits into his criteria very well.

All in Eldo:

P1 of Green Spur.
Right hand variation of P1 of Blind Faith (is 5.9 if you are of average height for a man)
Good Cleavage
Rover Dihedral
Rincon P1 (as if it's not already over-crowded)

Also in Eldo:
left hand variation on V3 at Cadillac is fun
Pony Express pitch 1 as suggested is great
Ruper w/ Rover dihedral pitch 2 is great - I just did it a couple weeks ago

I found decent gear on Buck Fever, (Kirk's Corner, Locksmith, & Lichen or not - BUT NOT NOW!!). Ragger Bagger is a good 8+; Green Spur good too.

Sorry - Steppenwolf was one of my first 5.9 leads in CO back in the day and i don't remember it being bad. Must have been a low gravity day. The perch is good though anyway - Ragger Bagger and Gobble Up are good 5.8 crack lines to get ready for 5.9

Whistlestop, The Flakes, Heavy Weather in Eldo; Classic Finger Crack and Tough Situation in Bldr Canyon; Mainliner and Loose Ends at Lumpy.

Eldo:
The flakes
Whistle stop (easiest 9 in the canyon?)
Heavy weather
The Bulge last pitch variation (also in contention for easiest 9) although the rest of the climb is fairly runout
Touch n go 8+
Rincon p1&2
Over n out to over the hill
Darkness til Dawn used to be 9+, no real 5.10 moves, just sustained 5.9
Pony Express p1
Allosaur - runout on 7ish terrain

In Eldorado, I'd add Handcracker Direct. It's rated 10a but I think it's soft for the grade and the crux can be laced up.

Perversion on Eldorado Mountain

Security Risk in Boulder Canyon

Center Route on Cynical Pinnacle

I greatly appreciate the responses. It seems like a creepy grade to move into but it also seems like doors really open up in the alpine once you hit it. I need to go out and scare myself on safe stuff.

The 9's in the mountains generally aren't going to have 1/2 the pro of any of the above routes, so you may want to train for that. It's not atypical for a 5.9 alpine climber to be doing 12 in the gym, 11 sport, 10 trad and 9 in the mountains. It's not just the pro, it's also the speed you'll be able to climb at to avoid weather while pulling off much longer routes. Nobody is going to be going very fast right at their limit. There are no special routes, secrets or shortcuts to these things, just get out a lot and keep challenging yourself on new things.

Turkey Shoot, Cardiac Crack, Tee Pee Tower Crack, Center Route (closed right now) all in the Platte.

Want a heart attack? Walk up to Cardiac Crack!
Actually it's worth the walk. I did it a couple of days ago after many years. It takes gear fine. If it was in Boulder Canyon circa 2008 it'd be a 5.10.

Jared, here is a post from me last year that might help.

http://www.mountainproject.com/v/colorado__rocky_mountain_re>>>>>

If you want a 1 move 5.9 with gear at your chest during the move try Nightcap at Happy Hour.

I think your right Allen, Cardiac Crack is a pretty stiff 9 but it takes gear all the way up. I wasn't a real strong 9 leader the first time I climbed it a few years ago and I used up all my number 3s and had to run it out to the top. Jared, if you climb this route take a few extra 3 and 4s to be comfortable.

Keep in mind that there are many 10a's around Boulder that feel easier than many 5.9's, and many 5.8's that feel like 9's. The older routes tend to be more sandbagged. After onsighting a few 10a's, I fell off of a 5.9. Anyway, the grade is about the same around Boulder. Especially beware of 9+, as this usually means it is an old route that they hesitate to upgrade.

Also, 5.8 in Eldo can feel like 5.9 if you aren't used to the climbing. Get on Ruper(8+)if you have a full day, Do the Great Zot start on Rewritten(8+ at the start), and finish on Rebuffat's arete for awesome exposure.
Cosmosis 10a and Dementia 10a(both in Boulder Canyon), both protect really well and aren't really harder than many 5.9's. (try Green Spur (9) and then do Dementia (10a), you decide which is harder!!!)

Also, Blind faith is a pretty solid 10a, but feels mentally easier for me than Hair City (9+).
Cussin' Crack in Boulder Canyon is 5.7, but that was one of the toughest. I've also heard horror stories about the Umph Slot(8) on the Dome (Many 5.10 climbers get rejected). You might want to hold off on Rosy Crucifiction(10a).

If you go to Lumpy Ridge, the lines sew up well, but I might start with some 5.7, or even do Osiris (5.6).

Many good suggestions, thanks to everyone. I think I'll start with Nightcap and finger crack this week and see if they feel scary or very scary. If just scary then I'll start working on the rest of the suggestions you guys gave me. Much appreciated.