I had issues too every time I connected. I would run the loader stick to relieve pressure but it never worked. Then I made a call to my dealer and he reminded me that my third function was electronically controlled and I needed to have the tractor OFF with the key on run and press the third function valve. Since that discussion, I haven't had one not just slide on extremely easily. I just always have to remember to do it before I disconnect anything or that pressure is stored up in the implement side. THe only way around that was to crack open a line and bleed some pressure which is annoying and messier than necessary.
Just noticed you really are having issues on the de-coupling side. Move the sleeve around and try to lube as npalen mentioned. I've had them get grit in them before and re-lubing them helped.