Okay, here's a list of my stories that more or less fits with that:
Asking : He's not spanked at home, but after discovering that his friend's mother spanks her kids he decides to convince her to spank him too.
Dear Anne Letters: 05: a college students writes an agony aunt about how he's always wanted to be spanked.
Dear Anne Letters: 09: A high school student writes an agony aunt about how he has a chance to be watched after school by a woman who believes that he is a couple years younger than he really is and also spanks her own son
Dear Anne Letters: 23: a college students writes an agony aunt about how he always envied how his friend's sister spanked that friend - and asks if he should now (years later) ask her to spank him.
The series Distance Memories" touches on this. The hero has seen his crush spanked and now wants to see another girl spanked - but his attempts more often than not put his own rear at risk for a spanking (which he's fine with if he gets the chance to see a girl get a spanking).
Everything But...- A boy is curious about spanking. He asks a friend's mother about it, and that woman has permission to do everything but actually spank him....
The Genius - written before the Big Bang was on the air, this features a Sheldon Cooper like young genius in college.
Ghost Town: Bored and unsupervised, the hero explores a nearby ghost town (one that was only abandoned about a decade ago), stumbling over proof that one of the families that once lived there spanked. Making him wonder how it would it feel like to have parents who focused on him enough to notice what he was doing - even if it meant getting spanked. This sends him off to track down someone who used to live there.
Glass Wall: A boy has a limited talent for magic - which allows him to see through his apartment wall to see the girl next door getting a spanking, which leads to...
Home Made Wine: a new neighbour moves in next to a teenage boy. Since they have a son near his age and make home made wine in their garage, the two boys "borrow" some of the wine, leading to...
Moms Taking Charge - Part 1 & 2: Almost spanked for real during an otherwise playful birthday spanking, that near miss has haunted him for years. Then, while in community college, he stumbles over (actually is lured into) a website about mother spanking their older children. Does he click further (accepting that he will be spanked) or does he walk away?
The Problem With Chequebooks : A boy really wants to know what a spanking is while his mother is hard at work trying to balance her chequebook. Yes, it's a bit dated, with electric cheques replacing chequeboos, but it's a nice story about a boy who wants to know about spanking.
Reaching For A Memory : a youngish actor needs to be able to reach for a memory to act in a scene where he will get a fake spanking in a movie. Alas, he's never been spanked - at least not yet
A Realistic Story Of The 80s : A boy wants to be spanked, going so far as to buy a paddle in the hopes that it will be used.
Returning To The Family Reunion : Years ago he escaped getting spanked by a distant relative - and he's regretted ever since. Attending another reunion, this time as a adult, he tries to make a different choice.
Rival Cousins : A pair of cousins who submit to spanking in a way to one up each other.
Summer With The Relatives : for years he's been visiting his aunt's where she spanks her own children but respected his mother's non-spanking philosophy. He's now getting too old to spank, but has a desperate plan to finally be spanked.
Ted's Profitable Misadventures : another "set in a world of magic" story, Ted shapeshifts into a younger looking form (a fat one because of conservation of mass) as part of a plan, then discovers that he liked the outcome.
A Tribute - Version I : A boy, facing a possible spanking from his new stepmom, asks a guidance counselor help him get ready for it.
There maybe others that I have missed - feel free to go through my author page looking for more that touches on this theme. | 
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