Sorry, but you are being somewhat melodramatic! I take it you was never one of the lads? Tis a mate of mine, who is actually a really good bloke. She did find out and thought it was quite amusing - and for the record, he did reinflate the tyre for her.
Im sure your mate is sound and all the rest, Im just giving my take on it. Interfering in someones life in such a way is not the best way to win a date with them, its akin to harassment. Im just pointing out, not everyone would be so easygoing about it. My first thought would be that the person is the nutjob/stalker type and Id be pretty angry about it.
I was one of the lads, I just never needed all these tricks to get into a womans underwear.
(they fit just right if I buy the right size)