Might I suggest opening an account with
www.gmail.com I find this site better than hotmail.
When you send an email there is a link underneath the heading to "attach a file" and you should be able to navigate to your flashdrive, as usual, again DO NOT right click on the file, just
LEFT click on it and and then press the "Open" button. It should then show you a bar working from left to right as the file is uploaded and when it is finished the name of the file should be in italics with a tick next to it.
It is all quite self explanatory when you look at it, just my instructions without seeing the page in front of you might seem too much to take in at once. Perhaps have a practice at home before you go.
Again, never RIGHT click when you have an email programme open.