I don't know how to give you advice on sex because sex is not something I particularly enjoy doing. Being asexual hinders my ability to experience attraction and arousal towards others.
Over six months ago, I was extremely vulnerable about my body due to gender dysphoria, I made out with a person and didn't think it would go further than that. It did, they were drunk and began groping my body, I froze. I was not aroused and they shoved their hand down my pants, tried giving me a handjob, when that didn't work, they stuck their fingers inside me. Being reminded of the fact I have a vagina pushed me over the edge. I burst into tears and was inconsolable. I ended up going home after that, I didn't want to be comforted by anyone which is normal for me. I don't like to be comforted when I am upset.
Aside from the situation itself, being touched in the vagina region when I am vulnerable is off-limits. I am not sure if the same applies for your boyfriend. When I am upset, I like to be left alone to introspect and come to my senses. I'm not sure if the same applies for your boyfriend, perhaps he wants to be comforted or left alone. Is there a reason he doesn't answer you when you ask...? Has he had emotional breakdowns due to gender dysphoria before? How has he handled them in the past, by opening up to you or pulling away until he feels better or in the right head-space?
If all else fails, you can reassure him that you love him, you care about him and that you'll be there waiting when he is ready. It might be best to discuss with him how he wants to have sex, as he is the best person to ask. Maybe with top surgery coming up in December, he may be feeling too nervous/anxious/scared to enjoy sex like he usually does as his attention is solely on top-surgery and the possible outcomes - both good/bad. Perhaps discuss with him about his concerns regarding surgery, maybe he needs someone to vent to about his worries?
There are no silly questions, please don't worry about that. It is good you are asking questions.
