You can pump in a flaccid state, but it is better to be erect or semi-erect.
Once you are in the state you are going to use, lube up your shaft and the base of and the first few inches inside the cylinder.
Once you've got that taken care of, go inside the tube, press the base of the tube against the pubic region, and start pumping. You'll want to do this to time, so start the clock as soon as you establish a seal.
For beginners, slowly build to a pressure setting of 5 in Hg (obviously, I recommend pumping with a pressure guage).
For the first week, only pump for about 10 minutes.
How you want to increase in pressure and time is up to you. However, whatever increases you decide to make, I recommend you make them one at a time and do them gradually.
Don't cross the pleasure/pain threshold. If it starts to feel uncomfortable. Back off of the pressure.
If you notice any blisters form on your shaft, you will have to discontinue pumping until you heal. This is the greatest incentive to be gradual with your increases.
I recommend you be conservative at first just to be on the safe side.
Hope this helps.