Hey /r/BDSMcommunity. Long time lurker, and thought I'd finally make a post asking a question that's been burning a hole in me recently.

In the past couple months I realized I very much had a sissification/feminization kink. I explored it a bit (I post audios on /r/GoneWildAudio, so mainly I explored it by making audios involving it, nothing in-person due to lack of privacy) and slowly became more familiar and knowledgeable about the kink. I talked about it with my girlfriend and she's 110% supportive of it and likes the idea, to the point that she bought a strap-on and has suggested that I wear her panties and even go as far as to dress up if I ever so wanted to during sexy time.

However the problem we've ran into while exploring this genre of kink is that it always seems to also involve forms of degradation or humiliation. Everything we've found online involving sissification/feminization (porn, captioned images, articles, etc) has always involved a tone of something along the lines of "Lol sissy fag! Your cock is pathetic, just like you whenever you try to be a man. That's why you're better as a woman.". She's not comfortable with saying such things, and the idea of being told such things is a major turn off for me and not even an aspect of the kink that drew my attention/interest in the first place.

I feel like it's a stupid question, but is it possible to do sissification/feminization without having to also include factors of degradation and humiliation? Or is the basis of the kink just that there almost has to be some minor aspects of degradation and humiliation involved? Anyone that has explored the kink before, what was/is your experience with it? Did you basically have a dom/sub relationship during it? Did you or your partner play into the role and kind of assumed the identification of a female during it? What other ways did you and/or your partner express this kink besides pegging or the usage of a strap-on?

Now onto pegging. Little background, me and my girlfriend are long distance so we only see each other about once every 2 months. So while we've dirty talked about sissification and pegging over text, we haven't been able to explore it at all in-person besides for maybe 20 minutes the last time we met when we realized we had completely forgotten that she had packed her strap-on. We only had time for me to teasingly suck on it while looking up at her, but she absolutely loved looking down at me like that and said it was one of the hottest things ever. We both want to explore the world of pegging, but neither of us really know where to begin. We've done anal with her before, so we do know the basics like having a safe word and constantly communicating to make sure everything is alright, being prepared for a possible/likely mess, and knowing that you need to start off slow and can't just go balls deep right off the bat. However, we do still have some questions. Like what would be the best position(s) for beginners, what to expect at first, ways to warm up, ways to mentally and physically prepare, etc.

Any and all advice/insight would be greatly welcomed for both topics. Thanks!