The best way is to have an OPEN CONVERSATION, As we can see u r trying to make her feel comfortable around u, tell her how u feel and how u will still love her despite her flaws (which are flaws becuz of the negative beauty standards that makes natural look ugly) And these issues are something u can only help her with,but the efforts of getting out of it and working on it, are the things only she can do. If she is insecure, it's a fight in her mind…in which u can only accompany her in and she has to fight and win the battle.
Whenever you want as long as you BOTH are consenting. Hell you can even skip the first date and just bang. There are no set of rules to this, anyone who says anything degrading about this needs to get out of your life.
The best way is to have an OPEN CONVERSATION, As we can see u r trying to make her feel comfortable around u, tell her how u feel and how u will still love her despite her flaws (which are flaws becuz of the negative beauty standards that makes natural look ugly) And these issues are something u can only help her with,but the efforts of getting out of it and working on it, are the things only she can do. If she is insecure, it's a fight in her mind…in which u can only accompany her in and she has to fight and win the battle.
Whenever you want as long as you BOTH are consenting. Hell you can even skip the first date and just bang. There are no set of rules to this, anyone who says anything degrading about this needs to get out of your life.