Would have replied sooner but stopped at
When I try and pump some air in I end up on the ceiling.
I still don't understand what that means.
Withal...
Does the problem occur with presta valves on other bikes?
If it's a dual head pump , i.e. schrader & presta, does the problem occur with schrader valves as well as presta?
The question is whether it's the valves on the road bike, or the pump, or some unusual combination of both.
My (limited) experience is of a track pump that has gradually become leakier at the valve end. Surprisingly that's on both presta & schrader valves.
HTH.