Okay! Let's see what we've got here.
Q's
1. No, he's an only child. He probably had family other than his mother but they didn't live nearby so he didn't see them often. Didn't have many friends but had plenty of fuck-buddies. His family just see him as fairly normal since they mostly don't know about his gifts.
2. He's gained muscle thanks to all the walking, climbing, and fucking he does. But it's more like lithe athletic muscle than big bulky muscle.
3. He had his home region's version of Ratatta/Zigzagoon/Bidoof when he was a Shorts Kid, but gave it away later on because he was no good at battling.
4. His main hobby is Shorts, other than that he tends to jump from hobby to hobby whenever something catches his interest. His favorite gam is actually an indie title, it's really good but you probably haven't heard of it :P
Ideas
1. Never played Masters, so this is unlikely to happen.
2. I suppose that could work, but I have no idea how I'd write it in, so for now it can just be a head-canon.
3. I like this, maybe she's immediatly open to being fucked and captrered... until she sees the MC stood on the flower and instantly goes on the attack