You thought about it for a bit. Mom and Emi were willing to help you, but they were willing. If you were going to do something like this it would have to be on someone that didn’t expect it. After all, you’ll probably never find a situation when someone will present themselves to you like your mom and sister are doing. Even Ms. Ember next door was more of a safe choice. It probably was just her inside her house. No one to see or hear what you were doing. If you truly wanted to be able to do this in the future, then you had to be bold. “... I’ll go find someone outside. I… I have to do this.” Mom looked at you with a proud expression and a nod while Emi patted your back.
“You got this Big Bro.” She smiled and gave you a thumbs up and you smiled back giving her your own. You finished breakfast shortly after and went to your room to put on some loose clothing. While you could do this while dressed, getting out with the clothes was… not exactly easy. It is better to attempt to use “wear” naked, as embarrassing as it is. So with some sneakers you just slipped on, some shorts and a loose t-shirt you left the house, saying goodbye to Mom and Emi as you exited your house and looked around the neighborhood. Most of the houses had a fair distance between them. This wasn’t the well-off part of town or anything, more like a middle-class district. But the houses here still managed to leave some privacy, not to mention that most of them were surrounded by trees. Overall, one knew their neighbors here, but more often than not didn’t speak to them unless they were close friends or something. Still though, despite not speaking with them often, there were always a few anthros that you could spot in the same place at around the same time.
In the house in front of yours was the house of Mrs. Belle. She is a divorced anthro hyena whose kids have left her home already. She’s pretty curvy, with big breasts and ass, thick thighs and somewhat pudgy, a bit more than your mom. The thing she’s most known for is that she tries to seduce anyone that passes by her door. If you go talk to her, she may just take you inside before you even say anything.
Another option you saw was a male bird anthro. They had jogging wear on and seemed to be listening to music as they made their run. You always see them around this hour and also have a very good general idea of their route, so you could surprise them at some point. Their form is sleek, a bit of a bubble butt and wide hips.
In another house, next to the one of Mrs. Belle, was another neighbor who you don’t really know. An anthro bat who worked night shifts somewhere. They always arrive at this hour pretty tired, and you’re sure they just sleep until some hours past noon. Their form is more fit than the jogger’s at first glance, but still kind of lean. If you’re careful you could sneak onto them or slip inside their house while they sleep.
Another neighbor you saw was a raccoon anthro lady with glasses. She seemed to have a decent figure, decent breasts that look like a D cup, nice hips and round ass, and a big fluffy tail behind her. She was moving boxes out of her garage it seems like. You could go and offer to help, and maybe get invited inside afterwards. You think you can try “wear” on her.
The next anthro you saw was one of the most curious ones, at least to you. Next to the dragons of course. It was an anthro dinosaur, specifically, a female anthro brachiosaurus. Her most defining feature was the length of her neck, though she had a pretty decent pear shaped form, with more emphasis on her butt. She seemed to be painting the outside of her house, occasionally drying herself with a towel and having to push up her sweatpants.
All of them seemed like good targets to try and “wear”. You’re fairly sure of your chances with all of them, though now the question is simply… who to go for?