I wish there were more women like you! I am a male and also enjoy anal stimulation. However, I was quite hesitant to ever bring it up to my partner, because some people do consider it a doorway to being gay. This is absolutely not the case! So, I'll will also try to answer your questions and provide some insight for what worked for me. 1. Is his reaction normal? The confusion, not sure if he liked it, wanted it again, whatever.... Yes, this is normal. Again, it comes from him feeling like it could make him gay. It will be your job to explain how sexy you find it and assure him he's even more of a man for being open minded. 2. IF I do this again, I would likely want to take baby steps for him. How far should I go?? Fingertip? The length of the nail bed? To the first bend in the finger? Do I just judge and see what he reacts to? I'm new to this also... The best thing to do is take it slow. Starting with a finger is a great idea. Let him know beforehand that you will always stop if he says to. Make sure he's relaxed and don't hesitate to use lots of lube. Starting after you've already got him hot and horny helps make it easier too. 3. I have nails, not long, but should I use a finger condom? Or will this feel differently? Long nails can be a risk. It can be done carefully, but I'd suggest using a condom over the finger in those cases. It will feel just as good! 4. Lots of lube, little? (The firs two times, there was no ACTUAL insertion, so there was no lube and it was kind of unplanned.) Lots, always lots. Be aware that as you move to larger things (i love being fucked with my gf's strap-on) it will cause some pain at first. Pull it out, and start to slowly insert again. It may take two or three attempts, but the muscles there will relax. Happy playing!