she usually wears on the first and second meeting. no sense in going through the risk if he can't even use it. once she's comfortable, she'll demand that he deposit inside her
she fucked him but she's reluctant to say it. the pictures with guys legs, the hot tub. It almost begs the question - why DIDN'T they fuck? He wants to stay single, sure - isn't this why he's single?
I get that you're worried about her wanting more than sex. but don't be blind to the fact that it may happen with someone she meets as a result of your new adventures.