1.) Well my wife can daydream her way to an orgasm, although it is not nearly as intense as one brought about by sexual contact.

2.) I can only speak about my own experiences but men can have multiple orgasms. Further more our nipples can be as sensitive as a woman's as can our neck with heavy breathing and nipping, sensitive places such as the ribs, back of the neck along the hairline, armpits, inner thighs, behind the knees and along the spine can be teased. Finally prostate massaging can heighten the orgasm and perhaps fill (the pun wasn't intended but I guess it fits) the desire to know what a woman would feel. There are many guides on how to go such things but my advise is to find a partner willing to experiment and go slowly taking your time with the foreplay.