Sex Questions! (NSFW)

I have never had front hole sex due to massive discomfort with the idea of penetration in that fashion, but lately, due in part to my awesomely supportive husband, I've been considering trying it. Mostly I have some concerns about pain, as well as whether there's any possibility that I could still get with spawn even with me being in T. Most of the info I could find said no, but...well, y'never know and I trust you guys with lived experiences.

What can I do to make this feel good for me? My husband's a pretty big dude, do I need to like...stretch myself? I can has help wit sexings, please?