Speaking as a man who has played them all, not beaten them all (no pun intended), I would start with Andy P's Cock Hero 3. Use this list viewtopic.php?f=25&t=8393
Go from CH3 through to Ch nations Part 2. Then I'd probably play some of Vindicare's Flux series, maybe up to Episode 4 or so, from there I'd switch between the two, Andyp and Vindicare until they are done.
See how you get on with that for starters, that'll take you a good few weeks anyway. After that go check out some of the others, some quality offerings from all the rest of the guys, they are all brilliant in their own right. Supermokkori's stuff, MrBlonde's vids, utopia had some good vids, hiphopanonymous puts out some quality shit. I stick by this one though, the best ending ever has to go to Bornforthis and Gracie Glam.
Enjoy your time my friend and stock up on lube before you start.