So I’m somewhat new to this. My first time was about a year ago from now, and so far, my main goal is to improve my masturbation which has worked greatly, but I also want to see what a Prostate orgasm feels like. It took a while to see what worked, and what stimulates me the most out of all the things I’ve tried (anal toys, and one small vibrator) is a thrusting dildo. It felt great and it almost felt like I was going to orgasm, but instead it calmed down and I stopped to call it a day. I know these sorts of things take up to 45 minutes or more, but I’m sort of a visual learner and wanted to see other people’s experiences to see how I can last longer and any tips to maximize the orgasm. I’d say that my last time I went for like 3 minutes with the toy and almost orgasmed so any advice on what I should do would be appreciated. I also wanted to ask about how long I should keep it in there. I heard from a friend that you need to take it out to lube it again after some time, but I don’t know what a good time would be? Does a break in between the masturbation help with the orgasm or should I just wait out the entire period?
Weirdly I think there’s no set answers to give as such as we all are different in what works for us but yeah it’s good to keep the toy lubed up to avoid any internal friction damage. For me in the past I’ve gotten to the point then taken the toy out so I could use my fingers to finish it off and that actually worked well but also keeping the toy in and kept going worked too so maybe just carry on experimenting to see what happens for you 
Usually just leave the toy in on its highest setting, however I am a visual person so it is only usually achieved flicking through the pages of a porn magazine or the OH is naked in front of me, playing with her breasts and pussy. Never managed to achieve a prostate orgasm without visual stimulation.
I find what works for me is using a dildo starting with light to moderate thrusting to warm up. You need to get yourself aroused and turned on as this is key in reaching a prostate orgasm. Take your time and gradually increase the speed of thrusting throughout the session.
If you are hitting your prostate, you should gradually feel pleasure building. I often feel the sensation of having to pee and often feel sensation building in my groin and ass and spreading through my body. I often will start dripping prostate fluid and precum as well.
At this point I often feel an orgasm building a nd increase speed of stimulation building the orgasm until peak. It’s a wave of intense pleasure and I often feel as if I’m bearing down when it happens. I love the feeling and the fact that I can have multiples during a session.
Some great advice here, and an interesting point about the visual stimulation.
I have tried prostate massage from time to time and felt some lovely sensations, but never got to the elusive full body orgasm (or ‘super O’).
None of the advice I have seen previously went into visual stimulation, giving the impression the key is mentally training yourself to reach it through concentrating on what’s happening, and not even touching yourself.
So I am wondering what stimulation people on here use, if any.
It does take time and practice. I had quite a few sessions before I got anywhere near an orgasm. Often finished myself off with a HJ on the first few goes. You will eventually get there as you understand the sensations more and more.
Visual stimulation is key. You need to be aroused to have any chance - in my view. I also found a long stint without any masturbation or sex helps. Then a couple of days out start edging yourself a bit to get aroused and stop. Repeat again the day before and then even on the day before going for it. This was how I got my first anal orgasm. I was on the edge before I’d even started. The session still took a while and it took all of my willpower to not grab myself and go crazy but it was so worth it when it hit!
Good luck and try to enjoy each session for what it is. It will come