Does your KH/OH milk your prostate? Or does she make you milk yourself? How easy/difficult have you found it when milking yourself? And what has helped you to do so successfully?
My wife or her boyfriend will massage my prostate once a month. It takes between 30 and 45 minutes till I start dripping into my bowl to consume. I'm usually drained about 10 minutes later. They use their fingers.
I have only tried to milk myself once while the wife was on a business trip and it left me more frustrated than if I left well enough alone. My finger just could not reach with the position I had my wrist bent and the anal probe was just not hitting the right spot. Now my wife/KH/Mistress nails the spot everytime and the outcome depends on the amount of lock time and the tool she uses. If she uses a mini dildo it takes only a few minutes and that does give me a mini orgasm feeling but not anything to write home about. The anal probe sits around in the middle, roughly about 10 minutes to start really flowing and takes another 7-10 minutes to complete and left off edge but still wanting. Last, her fingers, she can drag it on for 30 minutes before the dam breaks and work it for 10-15 minutes before she is satisfied I'm empty. When she is done, I'm empty and exhausted and left relaxed but still frustrated. Usually, I fall asleep real quick for the first 2 hours but wake up in the middle of the night with an erection trying to form and the rest of the night is a restless sleep. What is described above is when we have decided on a 14 day lock cycle and the milking comes at the end of the first week. (day 7). At the end of the 14 days, she likes to either ride or be ridden and I am allowed to have a full orgasm. If we are doing Locktober or Lent, There is no milking or any release until the last day (day 31 or 41) and that is only a milking. Those are the most intense and sometimes the worst. Once milked, I must remain in my cage for another 24 hours and then she has her way with me.
I am milked occasionally by MIstress, using her gloved and lubed finger. She has me "assume the position" on all fours on the bed and She can quickly locate and begin massaging my "walnut" and I can feel the fluids moving, but never really achieve any sort of ejaculation or orgasm. The whole process takes only a few minutes and the 'drippings' are caught in a bowl placed under my clitty. I quickly consume the drippings and find myself pretty drained and sleepy. Mistress says that it makes me "docile" and nicely feminine for a few days and She prefers me that way.
I've tried with my own finger(s) too, but just can't reach deep enough, or for long enough before I feel like my arm wants to die. I have a prostate buttplug which can hit the right spot, but I need to have more of a play with it to make it more of a enjoyable and reliable form of pleasure - I haven't used it extensively yet, as I had only recently ejaculated, so want to build up some fluid to milk.
It might sound boring but my release schedule is set as follows: Birthday,Anniversary,Christmas and SummerVacation I get a full orgasm via handjob.The remaining 8 months I get a prostate milking while caged. It is always performed by a Masseuse. It took around three months of twice a week trials to perfect her technique,which is now outstanding! Depending on her mood and/ or my KH/Wife's instructions it can take from 15 to 45 minutes, whether the idea is to make it a most pleasurable,desperate or clinical procedure. She exactly knows the location of my gland and knows how to work with her fingers to induce different sensations and make me beg her to finish as soon as possible or make it last forever! Expulsion of fluid can be from almost unnoticed to an "explotion" of the prostate producing a whole body shivering. In the end,whatever happens,there is certain amount of relief ,but frustration is what prevails.
It sounds like it takes a few attempts to locate the gland so you can be milked. If you wait longer before milking is it easier or harder to do, or does it matter?
1) you are right,first goal is to locate the gland.After that it takes time to know exactly where to touch it and the intensity.It may happen that instead of semen you can't control yourself and pee abundantly lol ! 2) In my experience, the longer you wait the easier it is, because it helps if you are full and desperate to get at least this kind of relief!
My wife mentioned mine last night so likely to be milked with a lelo loki massager on Sunday. It will be the 3rd one so far this year so not very experienced
I'm actually no longer sure that all men can experience this. I personally have tried for years using fingers & toys. I've also had others try to milk me and to date it's proven completely impossible. Locked or unlocked. Denied for days, weeks or months. Teased or ignored. Nothing makes a difference, it just doesn't work. Everything functions perfectly normally, milking on the other hand just doesn't work at all. The only thing that will work is an e-stim buttplug...
In my experience it depends on the technique and the goal to be achieved. For example, two extremes, 1)with a thorough ,slow , delicate prostate massage thick semen is obtained eventually,like a lava flow vs. 2) a quick,vibration like,more intense,short stimulation ( by the way ,that will make you beg to be stopped) will obtain thin,transparent precum! And in both cases all sensations will be in your anus and prostate,your penis won't "exist" lol