Try cocking it, decocking it, etc... sometimes that helps.
Also, air must be escaping somewhere. Is it escaping from the fill port, or is it escaping out of the barrel of the gun? That's a good clue.
When the gun has "some" pressure in the cylinder, you...don't...need to cock the gun.
With 100 pumps on your pump, either the pump is faulty or the cylinder gauge is faulty.
Those 100 pumps should have gotten pretty difficult at 175 or so bar. But 200 bar should be plenty diable...provided you weigh more than 175 or so pounds !
Also...do NOT, let the lower area of the pump get hot. If it's working correctly, it should have started getting warm at about 50 pumps.
If...the pumping action, did not get difficult, around 40 or 50 pumps, there's most likely a problem with the pump not sealing internally.
Last thing, when everything is working correctly, I've found that, when you pull the handle up, pull it "all..." the way up. Don't stop part way. And equally important, when you hit the bottom of the stroke, hold the handle there for a second or two. This will help make sure that the air has past the valve in the guns air cylinder.
Good luck.
Mike