My family crossdressing stories are friendly ones, I don't tend to write about forced situations, but ones where acceptance of a boy's more feminine side is realised gradually and while there might be some reluctance, they are eased over it. They're about young crossdressers who are in situations which have a strong dose of reality in them, rather than completely fantastic settings.
When Annette hears from a friend that her young son Carl looks cute in his friend's dress she wants to see how he looks for herself, so re-lives his game in a real shop for some fun, picking a delightful party dress. Once she sees how cute her son is as a girl, she doesn't want him to change back and gently encourages him to keep the dress on for fun while they complete their shopping and she gathers some more girly items.
Once he's over his initial nerves, Carl starts to relax and enjoy wearing the outfit. Annette feels a little guilty about pushing him towards femininity, but not enough to stop her dressing him up again for an extra day of mother and daughter time.
The Double-Dip Halloween follows Ant and Joey, boys who are trying to win a Halloween competition against Ant's sister and her friend. When their sneaky plan to get the most candy goes wrong, Joey's aunt can't resist the opportunity to slip him into a pretty dress for a round of trick or treating. Can Joey survive the evening without being discovered? Will he start to enjoy all the extra attention? You'll have to read the story to find out!
Bored in lockdown, Amber convinces her sister and cousin to put on a fashion show with her. The only problem is, her cousin Matt doesn't have any interesting or pretty clothes with him. With a bit of a push, Amber gets him to try on one of her old dresses, and the show is on! Matt has some worries, but soon he's enjoying his afternoon strutting his stuff as one of the girls.
Eddie's got himself in trouble, he's forgotten it's fancy dress day at school for charity. If he goes home to change he'll get in trouble with the school and his mother, but if he stays as he is everyone will think he's too cheap to have fun. His cousin Claire comes up with an answer, but it'll involve Eddie wearing a skirt all day and being the butt of a lot of jokes.
Can he survive a whole day without his classmates finding out what's under his skirt? Does the girl he fancies now think he's a freak? You'll have to read it to find out!
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