Kanto's Newest (and Oldest) Gym Leader, Ashley (Patreon)

Commission for BehindTheMaskBTM on DA.

After Ash finally accepts his new body and life as a curvaceous older woman, he realizes he can no longer travel around and battle like he did as a young man. Using his skills gained over his Pokemon battles in his past life, Ash decides to open a gym in his hometown of Pallet Town, adopting a new confident and sexy persona as Ashley to play up her plump mature curves and throw off her opponents. 

I added some color edits of the outfit to imagine Ash/Ashley as a different type of gym leader, with fire, electric, and water types.