Disheartened newbie in need of assistance! (P-spot stuff and O-ring measurements)

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!

 

Thanks for the replies and help!

I'll look into a custom-fit chastity device later on but I think I'll stick to the larger ring for now, since that doesn't hurt (and still feels secure after I swapped another part on the belt). I tried using the smaller ring for two days and I was struck with a burning sensation when I removed it, so I figured it might be bad to wear it for a very long time like that.

When it comes to anal play, I believe I need to take my time and lessen my expectations. I did have a really good time once and believe I was on my way to an orgasm... but I've been unable to backtrack how I reached that stage and it took a quite long time to build up.

It might be a bit too personal but, if u don't mind me asking or maybe you'd prefer answering in PM (if at all, don't feel forced to!)... PouchyPantyLover, how does milking work for you? I've managed to hit a spot which made me feel a bit like I wanted to pee... however, I had already emptied my bladder and I think that I was on my way to doing it right and could feel some liquid trying to get out but the sensation also triggered a stronger erection, which prevented it all from happening. What are your thoughts on this? (Sorry if it's asking too much)

 

Thanks again for the reply @PouchPantyLover !

Quite funny, I did the exact opposite with the sizing of the cage. I went for a smaller gap between the cage and the ring and went with a little bit larger ring. The cage has been fitting nicely without pain. I woke during the first night with the morning wood but fell asleep again and haven't woken once since then! The area which I mentioned burned earlier was where I believe my D had grown a bit and was pressing against the smaller ring.

I think that changing so I get a cage I won't be able to grow in would make it impossible for the D to thicken as well? If so, I should get a smaller ring once I can get one of those I believe. I took some measurements and they indicaged my diameter should be around 5cm, which this ring actually is! (the smaller one is about 4.5cm).

I'm going to look for a smaller cage asap, so if it isn't against the rules on the forums to suggest places for purchasing them, I'd love some recommendations!

 

Thanks a lot for the reply @Xileh ! I appreciate it a lot