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It's not the only thing going on, but An Ordinary Teenage Sex Life might scratch that itch.
Well, the coming of age series, Stupid Boy, by GYounger ought to fill the bill - in 9 books and the 2 stories about Tony serve as a side trip. Pour a cold one, get settled, put your feet up and enjoy a great read.
https://storiesonline.net/series/1080/stupid-boy
You are right, but one character kept trying for four years - and came close.
I burrowed into the Collection file on SOL home page looking for a story I could not find in my own memory or hard drive. While there I made this list for firstlastest404. FLT404 can find the series with the search function for stories, collections or authors list and download for future reading.
Dark Vision "The Lottery" series
Doug Fox "Life in Paradise"
Dual Writer "Oh Boy"
Heatheranne "Huge"
Invid Fan "Bells Across the Universe"
Jay Cantrell "Brock Miller" series
JimC "Lucky Tickets"
Latikia "Ike Blacktower"
Michael Loucks - "Well-Lived Life"
Wizard "The Trailer Park" which is now part of "RWynter/Trailer Park" by Russell Hoisington
Old Fart "Jack & Jill"
Reluctant Sir "Dark Days"
Ryan Sylander "Hook, Pick and Lens"
SmokinDriver "Hindsight 20/20"
There is Lubrican too, to search. His are great but seldom overly long.
but one character kept trying for four years - and came close.
Can I get more details on that?
First story that comes to mind is Living next door to heaven, incest doesn't play a large role but coming of age/group sex does
Several stories by Losgud.
Help! by Lazlong.
Always Loved Her by General Principle.