Aunt is his prom date

[Brandnewbuddy]

80s or 90s (before it was so easy to look up stuff).

Guy has had a pretty strict upbringing and has a ton of trouble socializing. So he’s gotten to be a senior in high school with not even a single date let alone a girlfriend. Big dance is coming up and while he would skip, his parents conversely want him to go as it would be weird for him not to. They of course throw out suggestions he doesn’t want or won’t work…when his aunt pops by and volunteers herself.

Now guy’s dad was the first born of a large ass family while aunt is the baby. In fact, she’s in her early 20s. She got the same rough upbringing dad and MC got but during college she started branching out. She offers to be nephew’s prom date and to assuage parents she even agrees to not do anything wild after prom and even agrees to have her dress approved by them.

Course, she sees this as a chance to have the prom she never got and wants to try and let nephew look like he has game, so she shows a conservative dress to the parents then changes into a much more revealing one of the actual dance. She gases him up in front of his classmates (pretending to be his college girlfriend though, not wanting to push her luck she turns down an invite to a party, flashing a packaged condom from her purse saying she and nephew have plans of their own)

Only thing is: next dance she has with nephew, she feels something pressing against her…and she decides to press back against it.

 

[Rob_Royale]

Now guy’s dad was the first born of a large ass family while aunt is the baby. In fact, she’s in her early 20s.

This feels too much like your trying to make them appear a similar age, when the fact that they do not is what makes this taboo. A woman in her thirties can still look young and attractive but she has a maturity about her that is unmistakable. A poise and a confidence that no eighteen year old has and it triples her attractiveness to anyone paying attention.

 

[LFM90]

Love it roll with it

 

[Andreas_Kreuz]

Both approaches could work and would even deserve a story of their own. The girl who is almost the same age, but is actually the aunt. I'd probably make her less compliant with the her brother. Let the brother think she is just as conservative as he is, but when she picks up the son, she comes all dolled up in a sexy mini dress. Father is shocked, but now its too late...

 

[Andreas_Kreuz]

The other version of her being about 30 with the confident demeanor of a seductive woman, can also work very well. It offers more opportunity for nice dialogs and interactions with the class mates who try to hit on her as they believe the son would be too shy to pull it through. I think this offers interesting challenges for character evolution. I.e. the evolution of the aunt in the back-story, the evolution of the father when he sees his sister become a siren for his son, and of course the son. He suddenly has this hot girl at his side, what does he do with her? You created a scenario with a high stakes pivot that can be played out.