Two stories...
In Living In Another World, Andy attends a local computer fair and tries out a device that generates a picture of him as she would look as a girl. The next morning he wakes up as that very girl. Awkward in the role at first, he soon discovers that being a pretty young woman isn't the worst thing in the world.
In The Wrong Suitcase, Brian picks up the wrong suitcase, one filled with sexy, feminine clothing. The owner of the case, a beautiful woman named Lucille, contacts him to exchange luggage. Lucille confesses that 'she' is a male crossdresser. Before he knows what's happening to him, Brian has found his feminine self and has met a good-looking young man who not only doesn't mind the fact that Brian is a man dressing up as a woman but actually appreciates it.