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The .NET Framework is not specific to any one programming language; rather, it includes a library of functions that allows developers to rapidly build applications. Several supported languages include C#, VB.NET, C++ or ASP.NET.
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There are already well-known protocols for serial file transfer from the good old days. They are called xModem, yModem, zModem and kermit and .... Some of them are available in hyperterminal for windows.
There are some commercial libs ($$$) to be used with dotnet. There may be some free or open-source libraries too (one I found is at http://code.google.com/p/ymodemdotnet/source/browse/#svn%2Ftrunk%2FCurit.Module.RTX.Com, although it is C# you can use it as C# lib in a separate project and reference the lib from your VB.NET code). Another open source one is ZModem4net at http://sourceforge.net/projects/zmodem4dotnet/
You may also go with your own 'protocol' or send a zipped file and verify it after receive.
Send and receive has to be done in chunks (for example 2KByte at once). You have to repeatly read the data of the file into byte array and then write this to the serial port.