Keep him an unhappy unwilling sissy, so I can torture their father both with a sissy son who loves to tease and mock his cuckold father and with a second sissy son who is embarrassed and revolted by his father's being turned on by what a sissy he is.
Then I recalled that I'd written Tammy's brother onto the Suckwood High Football Team. Which reminded me of this series which gave me a name for this new character as well as something of an outline of how his captions might feel. It especially makes sense since how could two different whitebois get on the team? (Sidenote: for a doublet of captions I wrote in a drunken rush I've gotten a lot of mileage out of that series.)
When I was writing Stephi's introductory captions (Bonus: you even get one more introductory caption than normal) I noticed that they were all kind of linked and they seemed to work rather well as a "what happened to Stephi after he lost the big game against Blackmore" series so that's what the into captions became.
Alex Grey and Naomi Woods are probably the two models most emblematic of Stephi. But any blonde with small (but not mosquito bite) boobs. I have so many blonde teen sissy characters at this point that I've almost got the whole spectrum of boob sizes covered.
Mosquito Bites (eg: Elsa Jean): Tammy
"Normal" sized: Cindi
Large: Nobody yet although I have ideas. If you read the comments you might be able to put it together.
Too many words not enough smut. Time to fix that.