Novices and newbies discussion

Hello! I have two questions I’d like to ask but first I’d like to introduce a bit of my background so you’d understand me better! I’m somewhat new to chastity. I’ve been locked a bit before, had a long break and I’m now exploring it again (with a very close friend who’s my current dom though it’s through internet). One of my kinks is transformation and I get aroused by doing girly things and love getting praised for it. In general, I’m a “pleaser submissive”, who strive to please and improve for the sake of my dom. Letting them mold me so I can better please them is my biggest kink. I’ve been chasticed for two weeks now and I love it! I don’t want to be let out. I love getting horny and seeing that my d stays soft. I’ve started experimenting with putting things up in my rear and I want to try to reach a proper prostate (or sissy)gasm. Now, while I love being chastised, I’ve felt a bit disheartened lately. Two days ago, I was allowed to put a vibrator next to my cage and try to orgasm while playing with a dildo, which resulted in me having my first ever ejaculation without an actual orgasm. Same thing the day after but I believe I reached some kind of a half-orgasm or so. I’ve now been forbidden to use the vibrator though and (to my delight), my dom tries to push me towards pursuing a proper P-spot (or sissy)gasm. As I said above, I’d like to reach a climax from stimulating my P-spot. However, I’m unsure how to do it and while riding dildos or putting fingers or toys up my rear feels good, I feel a bit disheartened because I don’t seem to be getting closer or wiser about how to reach a proper orgasm at all. I’ve also found that trying to pin-point the P-spot is very tough! I’m not really sure if I actually know where it is /despite having played with my rear quite a bunch before and now). The problem I’ve faced the past few days is that it’s as if my mind knows I can’t climax and I don’t think I’ve made any progress towards getting there, so “there’s no point in trying…” (something along those lines and I’m not getting as excited from the play anymore). I feel a bit lost and disheartened at the moment and would love any kind of tips/help more experienced people could provide for me! Is it better to go gently or faster? High or low pressure? Gently first and rougher later? I know that all those things probably vary from person to person but hearing what worked for others might help me find my own way if I get to try! - I need help! (I’ve tried reading online but the few guides I’ve found haven’t been very clear - some said that if you hit a spot which make you feel like peeing, you’re doing it right, while another said you’re being too rough if that’s the case and I am clueless myself!) My second question is regarding the actual size of the O-ring. I’m a grower and used a ring, which measured 50mm in diameter. However, when cold, I actually managed to fall out of the cage while playing with my rear. I then switched to a ring which measured 45mm but woke up several times during the night in a bit of a pain. Now, I know my cage is a bit too big and lets me grow a bit, which is bad (I believe I have a CB6000s but I’m not completely certain). Anyway, I didn’t see any colour shift on my balls/skin while waking up with the horrible morning wood (so I guess it didn’t stop circulation… at least not for long?). I’ve read that the morning wood pain tend to stop being a problem after 1-2 weeks (is this true?). I can easily fit one finger in between while soft (as mentioned in guides online) even with the small ring. **My question is whether I should try to fight through the pain for a few nights and hope for the problem to end or would it be better to wear the bigger ring until I can get a custom-fit chastity device in the future? **(which probably will take a long time). During the day, I feel a slight discomfort if I get aroused with the small ring (it presses from the bottom) but it’s nothing big at all and the whole device feel comfortable in general. Thank you for reading!