There is astoundingly very few information on script and "getting started" on the net, though one can find a lot of scripts. When you want to assemble a script, just to play around with its features and implications, it gets quickly very difficult.
I had answered a similiar question here in detail, to show first steps and how to go.
I am generally using unixoide type systems, so I am not 100% sure on Windows. But if you have a (regtest) daemon running, using the command line and sending it some commands should do the trick.
Basically there are 5 steps:
- prepare addresses & balances
- create a tx
- sign the tx
- adjust the scriptsig
- send the tx
The most critical part is in step 4, where you need to play with length of the script - and probably a lot of trial and error :-) Good luck!