The way I knew I was ready is because the nervousness subsided when it actually started to happen. I was unbelievably nervous when I knew it could possibly happen that night. I was super nervous all night. Then when we started making out and things started getting hot and heavy. It all started to progress very naturally. I was so in the moment and turned on, the nerves weren't what was on my mind. There was a little nervousness/adrenaline but it was exciting not intimidating. Leave it up to the moment. If you are totally freaking out then you're probably not ready.

Yes I would suggest missionary first. This way he has control and it will be the easiest position for you to be comfortable in. He will most likely be able to penetrate you even though you haven't had much luck. You just want to spend a lot of time on the foreplay and really getting you turned on. The wetter you are the better. It might be a little uncomfortable at first or there might be a little sting from him stretching you. It should not be very painful by no means though. If it's painful that just means you're not ready to fit him yet. You can either continue with the foreplay and fingering until you feel you're ready to try again. Just keep working it until you feel comfortable with him in you. This could take a couple of nights before you're ready.

When he is giving you oral, you should do what feels natural. You'll probably start rubbing his head, moving your hips, arching your back. But do yourself a favor and don't worry about what you think you should be doing. Relax and really try to enjoy it. Like I said the more you're turned on the better. Plus an orgasm from someone else is amazing, and relaxing is the best thing you can do to get there.

With the shaving thing. Being clean is really what matters. But it being nice and trimmed is probably ideal. Or shaved. But if it's something you're not comfortable with or want to do...not a big deal