Samderella?

[Five_Inch_Heels]

The myriad of stories on the plot basis almost always have the rich guy or King/Prince seeking a younger female.

Perhaps the rich lady, or Queen/Princess is in the role of having spotted someone and chooses to pursue the matter?

Does Prong P properly fit Hole V?

 

[Rob_Royale]

Some gender swapped fairy tales would be great, and because you are completely changing out the character, so most of the problems with the no-aging-up-the-characters rule go away.

Cinder-fella? Bob White and the Seven Horny Lady Dwarves? Grandma can't wait until her grandson with the red cloak arrives, there's been a wolf prowling about.
Lots to work with here.

 

[Brandnewbuddy]

Gender-flipped Snow White would be fun. Especially if you kept “fairest” as the issue the evil queen has. So you have a a gorgeous effeminate guy running around the woods.

*pauses to imagine that* course now I’m thinking of making it a gay version as opposed to gender flip *imagines* god that’s hot.

Anywho:

Rapunzel would be fun. A woman climbs the tower to find a guy with the most luxurious hair.

I think a gender flip of the dancing princesses would be good.

Original version: soldier is tasked with investigating why princesses in a kingdom all have their shoes ruined each morning. He gets a ring of invisibility and finds out they’ve been sneaking to a fantastical place at night where they dance with princes (I think in some versions the princes are demons or monsters who have bewitched the women). In the story the soldier messes with the youngest princess by poking her or tapping her on the shoulder while he’s invisible.

So gender flip: our soldier is a tough woman who the princes all look down on but she follows them to where they are being seduced by succubi at night. Her pestering is essentially getting their attention to break them out of their enchantment. Like she grabs one of their dicks or does something to get them to take their mind off the succubi

 

[Carnevil9]

Some gender swapped fairy tales would be great, and because you are completely changing out the character, so most of the problems with the no-aging-up-the-characters rule go away.

Cinder-fella? Bob White and the Seven Horny Lady Dwarves? Grandma can't wait until her grandson with the red cloak arrives, there's been a wolf prowling about.
Lots to work with here.

There was a Jerry Lewis movie called Cinderfella a long time ago. I never saw it, but I imagine it was a gender-flip version.