I'm going to blame the adapter in this instance.

I have an old pump and adapter that I keep at work just in case I need it when I commute. It drives me insane. I usually have to tighten it to the extreme and then hold the nozzle just so while I pump with the other hand in order for any air to go into the tire. I usually end up letting most of the air out before I can get any air to go in. It's awful. It also doesn't help that sometimes the presta valves stick and need a little extra force to get that first pump of air in them.

I'd highly recommend a new floor pump with a head for presta and schrader valves. I have the Topeak Joe Blow 2 at home, its cheap, built well, and easy enough to top of the tires in the morning with just a few quick pumps. Honestly, go drop the $20-$30 on a new floor pump and your arms, upper body, and tires will thank you!