I don't agree the language you use. But I've had many similar experiences.
I can tell you just have to keep pushing the boundaries a little at a time with very even small escalations in flirtiness and touch. You then have to ask them for affirmative approval of your actions if there is any sign of discomfort or reluctance, if their is any tone of that you ask more specific questions.
If you want to escalate jokingly and non commitaly ask for the next step sometimes. Just act shy and blushy and beat around the bush before dropping it.
The whole dance is absolutely exhausting, everyone has a different expectation. And some people are just not going to be compatible because that's not who you are. When you have it figured out more it will come more naturally.
I think thought the environment for getting the feeling of how.to be yourself and how to communicate that through body language has never been worse for men ever. It's a minefield where the practical knowledge is first hand trial and error and the people that progress the most are the people that figure this out the earliest.
I can tell you the same dudes that did straight up sexually harass and assault my sister in highschool had no problems getting girl friends
Though I get the hesitancy I described this to a friend at a party and got yelled at by someone calling me a rapist Infront of dozens of my friends.