13Saturn

Jason/Diane Gets Ready for Game Day (Fan Art of Heads Up! by NewBeeTSF + Alt)

Added 2025-07-01 20:29:12 +0000 UTC

A quick little personal project I've been drawing for myself in between my many commissions and wanted to draw for a long time.

This is fan art for the amazing TG comic Head's Up! by NewBeeTSF over on DA. This is one of my favorite TG comics of all time so far, and I hope you check it out if you haven't already and are a fan of MILF TG.

To give a quick description of this story, Jason is a young man who after a bad night out partying, awakens the next day to find his head has been inexplicably placed on the body of a curvy middle aged woman! Jason's head and face slowly transforms to fit his new body, as he also slowly uncovers more about the life of the woman who's body he now has, with a larger conspiracy at play pushing him into accepting the life of Diane the sexy single mother.

(Spoilers below for those who haven't read the comic!)

This scene is a fan-fic that takes place after Jason/Diane has entered a relationship with Vincent and learned the truth of his transformation. Jason/Diane is getting ready to watch another football team and reconnect with his masculinity, but is disturbed by how much tighter the outfit is than the last time she wore it, and how much bigger her butt and cleavage look... What could be the reason?

Plus a bonus version with a different color scheme I almost went with.