To Carmad
The film that you are talking about is The Year My Voice Broke. It was made in about the late 80s and is set in the 50s or 60s. The girl is not actually asleep. The boy and girl (not sure of the actors ages, probably 19/20) are friends at school about the age of 15/16. The boy had seen something about hypnosis, and wants to try to hypnotise the girl. The girl goes along with it to prank him and pretends to be under his hypnotic control. So she is lying there pretending, and he thinks he has actually hypnotised her. Then he proceeds to carefully lift up her school dress and look at her panties and his having the time of his life at that moment. She then pretends to 'wake up' out of the trance really suddenly and catches him, and pretends to be all shocked by it saying stuff like "what are you doing?". He gets all flustered and embarrassed and doesn't know what to say and starts babbling like an idiot. Then she starts laughing and he realises she was pretending the whole time. She sees the whole episode as harmless fun, but he is mortified and begs her not to tell anyone about what he just did.
The girl is very hot. They have been friends for years and she has always seen him as a good friend and very innocent, but he spends the whole film trying to be much more than friends and wants her badly. There is another scene in the film where he is hiding in her back yard, peeping at her through the bedroom window as she is getting undressed for bed. When she is down to bra and panties (50s/early 60s style so not all that skimpy), he is praying to god for her to continue, but then she closes the curtains. In his frustration he steals a pair of her panties that are drying on the clothesline. He takes them home and in the next scene he is lying in bed clutching on to her panties and holding them against his head trying to use all the power of the mind that he can muster up to wish that she would be his girlfriend.
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