With a handle like yours, the obvious jokes aren't going to make it past the censors. I think the best I can offer on that front is Kinky Friedman's Big Richard.
There is a special on the mother ship for vodka and whipped cream-flavored cigars. Wouldn't smoke one if I died and you tried to put a lit one in my mouth, but they are being made and sold. The Cusano eXclusivo used to be pretty creamy, but I don't think they are made any more. The Lot 23 is a good mild-med cigar, to my tastes, but always reminded me more of peanuts than anything. No, peanuts, not that other thing.
It's been a long time since I've smoked a large number of mild cigars, as I like med and on up more now, but I'll go the direct route and try to offer some serious suggestions. Really. I'd think you'd want to stick mainly with shade-grown, milder stuff. Tough to imagine a creamy cigar with a CBL, San Andres or Sumatra leaf sungrown wrapper fitting the bill. I'll also try to stick with current offerings, as it appears you're looking for purchases, not nostalgia.
Rocky Patel Signature is creamy, IIRC. Not a big seller, and not many fans, but a go-to mild smoke for me at one point, and a bit creamier than Edge Lite (nka Edge Connecticut now, I believe) and RP Connie, which are also solid choices. If RP Sig is offered on Cbid, you can prolly get them on the cheap (singles on bid until Sunday currently going for a buck). Perdomo Champagne (the original, not SG nor noir). Had a Nub connie after buffet brunch at my first Cfest (last one they allowed smoking in the banquet room). Damned fine smoke after a mid to late-morning meal, and pretty creamy. I prefer the smallest, 354 IIRC. Espinosa Habano is a bit stronger and not quite as creamy, but the mothership has them on flash sale right now, 40 clams for 10. Good deal. Oliva connie may be the best connie I've smoked, and pretty creamy cigar. Love 'em. I recall Macanudo Gold as being fairly creamy, but also had a pretty noticeable (and tasty) lemon hint to them. Last I checked, still offered. Not scintillating, but Gurkha Symphony is fairly creamy and cheap. You probably have a decent chance with most AJF connie-wrapped cigars, too, but I cannot give you a rec on any one of them. Felipe Gregorio used to make a Pelo de Oro that was creamy. Don't think it's offered now, but if you can find a mild-med cigar made with the Pelo de Oro leaf, I'd give it a try. Subtle but smooth leaf. For a stronger smoke with a bit of creaminess, I always loved the original Torano Exodus Gold 1959. Habano 2000 wrapper gives nice body, a bit of spice and smooth, so there's a last note before I turn this into a full-time gig.
For Habanos, only in theory of course, I once had...er, heard the Boli Gold Medal, a small smoke, was imminently creamy and best sipped slowly, like a good wine. Not sure if they are regular line or were just a special. Only cigar I ever really just sipped, and not very big smoke. Aged like a dream. So I'm told.
