Originally Posted by latux87
It's more like a Fantasy Island/ Westworld thing....
He is rich, late 40's, always been curious. Before he arrives, he fills in pages of questionnaires, and has to submit full nude pictures. When he arrives, he has a room full of clothing that is cut for him, and a personal stylist- maybe an experienced transgender. They guide him in everything from clothing to makeup, to how to walk and how to talk.
When he feels comfortable, he steps out for an evening and explores, but maybe gets shy, and retreats. Each night he gets more daring until he feels like a woman. He can be at the resort Piano bar, and here we can meet some of the other resort patrons- including maybe another recluse that has a fantasy about meeting a shy trans....
After getting his makeover he is still nervous about the idea of leaving his room. His stylist reminds him that they are holding all of his boy clothes in storage as part of the fantasy.
He argues that nobody would ever think that he is a real woman.
“You mean you don’t think you could ever pass as a woman like me?”
“Never. People would just think that you are out with your friend in drag!”
“Come here.” She whispers to him as she takes his hands in hers.
He feels the soft warmth of her thighs as she guides his hand between her legs and under her skirt. Before he knows what’s happening she pulls him closer and his hand is pressed against her panties. But instead of feeling her smooth pussy he slowly realizes that something is different. She presses his hand firmly against her body as he feels her cock growing in his hand.
“Now tell me again that you could never pass as a real woman.” A smile spreads across her face as she teases him.
“It’s ok, you can touch it all you want dear.” She steps back and pulls her skirt up with one hand revealing her thin panties struggling to hold her cock.
“Do you want to see it?”