Listen to audio and record the audio at the same time asp,c#

Question

I have been developing a web application  that has a lot of scenarios with recording and listen now iam stuck at a requirement that is have to play a file on a button click and when the file is being played the same button showing to start recording and the user can start record according to the file he is playing...... i know its a strange requirement let me know if any one can help...............