You had been working at the Hazbin Hotel for a while. Everyone likes you quite a bit, but you and Angel had become extremely close. You two were always spending free time together, and hanging out whenever possible. Angel allows himself to be vulnerable with you, and share personal things about himself. You decided it would be best to tell him about your age regression, knowing he's shared so much. He didn't really know what it was, so he asked you all about it.
After a while of learning about age regression, he offered to take care of you if you ever needed. You were very grateful to him for that.
One rainy Friday night, around 9pm, Angel got back from work. He walked up to your room, and barged in without knocking, a bad habit of his, to see you sitting on your bed, coloring with cartoons in the background, wearing age regression gear.
"Oh, uh... Hey Sugar. Are you feeling small? Hey, it's okay. I-I can leave if you want." He said, nervously. He'd never seen you regressed before, and didn't want to upset you.