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.

 

[Jay142]

Once she feels his cock pressing against her, she gets horny too and decides to take his virginity. She takes him to the lover's lane and fucks him twice because he came so fast the first time. They then go to the party where he is strutting around with a new confidence after just getting laid for the first time. An alternative is to fuck him at the party so all his friends know he just fucked his hot date.

 

[Rob_Royale]

I keep returning to this idea, but man, high schoolers are just so NOT my thing, so I want to age up the man. Instead of a prom, it's a wedding he needs a plus-one for.
Aunt is married but astranged from her cheating husband. From the second her college-age nephew mentions that he's going alone to a wedding, she sees an opporunity to go out and just cut loose for a night, in perfect safety. It's not a bar or club with the girls where she could perhaps get herself in trouble with some young stud, but her own nephew at a wedding.
"Why don't I go with you? I could use a night out and you won't have to go stag."

The nephew of course has been crushing in his aunt for years and would happily beat the crap out of his uncle for what he's done.
Of course the wedding is in a hotel. A beach hotel. They have a good time, a few drinks, some dancing and at some point they are walking on the beach at dusk. His jacket is over his shoulder and she's carrying her heels and they are having a very intimate chat that ends in a kiss.

They don't leave the hotel for two days.

 

[Five_Inch_Heels]

I keep returning to this idea, but man, high schoolers are just so NOT my thing, so I want to age up the man. Instead of a prom, it's a wedding he needs a plus-one for.

Some kind of big frat party. Dude's kind of nerdy and not good with college girls. He's been telling a cover story for months that he has a girl 'back home' and that's why he hasn't been chasing girls like everyone else. They don't believe him and start giving him a hard time, maybe even saying they'll put him out of the Frat.

He goes home for the Holiday break and ends up telling his Aunt about all this. She's 30-ish and remembers how mean kids were to her at college.

They work out the details and the Frat is stunned at the eye candy on the nerd's arm.

 

[Five_Inch_Heels]

Auntie's pouring it on too, all snuggly and smoochy and touchy feely.

Crowd notices FratBoy's hands roaming freely also.