First relationship and nervous about when to initiate sex /u/Camperdot Sex

I’m 33F and I just started my first relationship and it’s with such a great guy, 40M. He has had sexual partners before and he is aware I haven’t and he has assured me we will take it slow so I’m comfortable. He is so kind and is allowing me to set the pace I need. Eventually I’d like more than the long hugs and cuddles I enjoy. I just don’t know how to initiate a kiss or anything more than that. I really want to but even talking about it with him has me stuttering and avoiding eye contact (I do have anxiety) but I don’t want that to keep me from pursuing what I want. Any tips? Would also love wisdom and advice on when I eventually lose my virginity. Any positions that would make it less painful? Thanks in advance- I really appreciate it.

I’m 33F and I just started my first relationship and it’s with such a great guy, 40M. He has had sexual partners before and he is aware I haven’t and he has assured me we will take it slow so I’m comfortable. He is so kind and is allowing me to set the pace I need. Eventually I’d like more than the long hugs and cuddles I enjoy. I just don’t know how to initiate a kiss or anything more than that. I really want to but even talking about it with him has me stuttering and avoiding eye contact (I do have anxiety) but I don’t want that to keep me from pursuing what I want. Any tips? Would also love wisdom and advice on when I eventually lose my virginity. Any positions that would make it less painful? Thanks in advance- I really appreciate it.