The issue is that the clutch in compression will squeeze all the oil out from the plates and creates a sticksion to the steels. What I do is after I get the engine firing uniformly and stable, I will ease throttle up to about 1500 with clutch pulled and rap the throttle up to about 2500 / 3000 or so (stay moderate) several times, and this will allow the plates and disc's to free and pump oil. After this it will enter first gear reasonably clean, You will always notice some feel to it as the trans jumps into motion, but much milder of a shock.
'97 VN1500 91 Cubes Of Custom CLASSIC
Vance & Hine 2to1
engine, forks, ignition & carb mod's
WebCam cam & rockers hard weld & grind
NEW TOP END, NO LOOKS ALL GO GO
Maxx intake manifold system & super G carb 44mm