I suggest using vibrating toys, the more powerful the better. The build up can be 10+ minutes. I also suggest learning about where the p-spot is... We first started with penetration generally and missed it all together. You read often on the mansion about a peeing sensation when you are in the right spot... that is a good start, but it takes some time to figure out how massage it. Lastly, a p-spot orgasm, if you can call it that, is totally different than a normal orgasm. You are not going for the usual feeling. It is more like intense pleasure you have just before you cum but it lasts as long as you massage it will stay at that almost there felling. And you won't feel the dripping, that will just happen. It is actually quite crazy because your penis feels nothing. I am pretty lucky, I seem to get there incredibly easily. We don't play that often, and it is terribly embarassing when we do as I get enough pleasure to prefer it. But my masculinity couldn't take it to have it all the time. Best of luck...
After many, many futile attempts at achieving and orgasm from pegging, we now resort to Her milking me with Her gloved finger. The juices flow, alright, and it certainly feels like its building up to an orgasm, but I never ejaculate! Afterwards, I am left drained and docile, but still no orgasm. Perhaps, if she can concentrate on rubbing your prostate with the strapon, you might be able to achieve ejaculation. Good luck!
A lot of it has to do with being able to relax with that sensation of having to urinate. If you’re potty trained, your body will naturally try to tense the muscles so as to not pee outside of the toilet anywhere. This is because your body has muscle memory when it comes to fluid in the urethra. This is why I suggest practicing with a plug, or aneros, or even an electric plug, while wearing diapers. Even if you don’t have a diaper fetish, it will at least help you relax with that peeing sensation since your body won’t be tensed up about the idea of peeing all over the floor.
I will definitely keep you updated. In fact here's an update. My chastity is already more permanent than it has ever been before, i.e. going to work in it, showering in it, and literally never taking it off except to groom hair. That's new to me. But here's the update...I'm going home for thanksgiving and she's going to visit her brother. However, we have decided that I shall continue to stay locked the entire time as usual. She'll have the key, and I'll have our lockbox with a key in it for emergencies, but other than that.....also I've never been around family while wearing it before.......I'll be home for about 5 days.......
I know where the prostate is, and it's always felt good. But getting over any sort of edge or getting anything to leak out or having any sort of intense sustained pleasure has eluded me without at least the tiniest bit of touching my penis. Combining the two (penis and prostate) always leads to amazingly pleasurable orgasms, but I want to chase the illusive hands-free orgasm wherever that rabbit hole takes me. The closest I've gotten is masturbating almost entirely anally and at the end barely jerking my limp penis (from lack of attention and relaxation and all that) just enough to kind of connect the sensation in my prostate up through to my tip and make me cum.
Lockedbyher90, you might want to look at the forums over at aneros.com. They have tons of information on the different prostate orgasms. They say its best to achieve a hands free prostate orgasm to leave the penis out of it. This will help you progress towards that goal much better. When you include the penis you will get further away from your goal. Also fyi the orgasm from ejaculating with prostate stimulation is whats called a super traditional orgasm or super T. The orgasm your looking for is called a super O. Heres some pages for further reading. http://wiki.malegspot.com/index.php?title=The_Super-O https://superoblog.com
This, in many ways is the path I am. Only its all been of my own doing. I've wanted a Super-O for a long time. I've been close once ....but never over the edge. Good luck!
A little practice and the right toy in her hands and you will get there. It took us a while to get the right "stimulation" but now it is fairly easy. It still takes a bit of time but it does happen!
It does take time but once you get there they are the most powerful orgasms ever I have multiple ones now although I have always been senitive back there being locked year in year out your body adjusts .I love anal orgasms and is all I am allowed and probably all i want now my wife loves them aswell
ineverknew, thanks for the info. The fact that a clear distinction in feeling that people universally agree on exists is good to know.