Ruined and milked

[Aarkey]

You may need additional stimulation- stroking to near orgasm before starting on the prostate massage, and/or some shaft stimulation/stroking during the prostate massage.

Not to side track the discussion too far but I tried for years - both solo and with my ex, to milk successfully. With no results other than a lot of clear pre-cum. However, I had fully successful results with a professional Domme who was much more interested in playing back there than my ex, and the pro would use her fingers on me for a while (perhaps 10 minutes) then used her strapon on me (seemed like 15 minutes) and then would resume milking with a pyrex g-spot toy. When it was all said and done there was quite a lot released.

In the past, I normally would get to that point when I felt like I needed to urinate, but then nothing would happen - but being fully restrained and overwhelmed as I was with the pro, all thinking disappeared and it just happened. I guess I couldn't relax enough to get "there" with it.

And there was no stimulation of my penis at all, nor was I let out of the belt for it to happen. She did it three times with me, and all three times she was able to get positive results out of me.

[TwistedMister]

Not to side track the discussion too far but I tried for years - both solo and with my ex, to milk successfully. With no results other than a lot of clear pre-cum. However, I had fully successful results with a professional Domme who was much more interested in playing back there than my ex, and the pro would use her fingers on me for a while (perhaps 10 minutes) then used her strapon on me (seemed like 15 minutes) and then would resume milking with a pyrex g-spot toy. When it was all said and done there was quite a lot released.

In the past, I normally would get to that point when I felt like I needed to urinate, but then nothing would happen - but being fully restrained and overwhelmed as I was with the pro, all thinking disappeared and it just happened. I guess I couldn't relax enough to get "there" with it.

And there was no stimulation of my penis at all, nor was I let out of the belt for it to happen. She did it three times with me, and all three times she was able to get positive results out of me.

Yeah, my suggestion was intended as a method for him to learn what it felt like and how to get there, then let it happen, without getting frustrated by a whole lot of nothing beforehand. So far, I can't get there without the additional stimulation, but I suspect that it might be different if I were to have a duplicate of your experience with the pro...I'd be interested in finding out, but I don't think Mrs. Twisted would be on-board with it...not yet anyway...

[SissyWannabe]

My Mistress does not like to leave me locked up when she has to go out of town overnight on business, so it has become a standard that, on the evening prior to her travels, I get milked to reduce my drive somewhat and to prevent my wanking. Since we rarely have PIV sex anymore, I have begun to look forward to those milkings and find myself glancing at her Google calendar frequently for her travel schedule!

[poptart1200]

I've been milked a few times before during my BDSM days. It's very frustrating, but it did feel pretty good.

I told my g/f how bloated I feel after 3 weeks of cum build up in my prostrate. She told me how she doesn't like my behavior during the few days after I cum, so she wants to limit my ejaculations. Right now I get a release once a month, but she wants to work that down to a full orgasm only 3 to 4 times a year. That would be tough to handle without RO and milking.

I introduced her to RO and we are doing that now. I also told her about milking. We have a strap on that I use on her for PIV sex while I am locked up and now she wants to peg me with it and milk me that way.

With milking and RO, we both get what we want, kind of.

[Grizzly228]

I've never been able to milk the prostate successfully. Feels like I've gotten close to *something* a few times but nothing happens. The feeling fades and I feel like an idiot with something up my bum and stop. Often vowing to stop and never try again due to the effort disappointment and frankly shame associated with it. I've got quite a few days worth of semen in me now so may try again later. Idk. I'm starting to think all those prostate websites and videos are scams. Lol. Not really but seems to be exaggerated.

[SissyWannabe]

We've found that just using a dildo doesn't cut it. There are little "Prostate Massage" devices that are curved to properly address the prostate directly. They seem to work well, but the gloved finger of my Mistress has been most effective in locating and manipulating my prostate to get the juices flowing. She didn't enjoy doing that much until seeing the immediate and direct effect it has on me. Just another way of her exercising total control over me!

[TwistedMister]

I've never been able to milk the prostate successfully. Feels like I've gotten close to *something* a few times but nothing happens. The feeling fades and I feel like an idiot with something up my bum and stop. Often vowing to stop and never try again due to the effort disappointment and frankly shame associated with it. I've got quite a few days worth of semen in me now so may try again later. Idk. I'm starting to think all those prostate websites and videos are scams. Lol. Not really but seems to be exaggerated.

LOL, not if it's done *right*.

Maybe having it done *to* you, and having no control over it would give some different results...

[Aarkey]

I'm starting to think all those prostate websites and videos are scams. Lol. Not really but seems to be exaggerated.

Well, it is definitely not something that is easily done for everyone. And I had actually gotten to the point of giving up as well. The only woman who was able to milk me, and she did it three times, was a pro-Domme who has gone to nursing school. She got into being a pro-Domme in part because she loved to play with men's butts, so... when compared to my ex wife, the pro was far more interested in working back there and making sure that she gave it her 100%

And she did.

It turns out that my prostate is a good bit deeper than for most men. The aneros toy just barely touches it. And the same for most women. So she ended up using a glass g-spot toy to actually give my prostate the kind of massaging motion that was needed for actual seminal fluid to come out. And it took time. And it was only after she'd fully scrambled my brain and I wasn't at all paying attention or self conscious of the fact that I felt like I needed to urinate... when she was "done" with me, I realized that it simply had happened.

She claims that she has never met a man she couldn't milk, though she insists on at least 7 days of denial first in order to "build up enough" and said that some men take quite a while to milk until they get more and more used to it. She also said she had a personal sissy slave who took originally took 30 mins when they started prostate milking, but she over the course of a couple of years of milking, she had trained him to be able to get milked in under 10 minutes, and to do it himself. She also said she had been training him to have prostate orgasms "sissygasms" but that his work relocated him before she'd been able to get him trained with it.

She's retired now from being a pro, but she both showed and convinced me that it is a do-able thing, though definitely not as easy for many of us as its made out to be in the fantasy stories.

[Caged55]

My Mistress does not like to leave me locked up when she has to go out of town overnight on business, so it has become a standard that, on the evening prior to her travels, I get milked to reduce my drive somewhat and to prevent my wanking. Since we rarely have PIV sex anymore, I have begun to look forward to those milkings and find myself glancing at her Google calendar frequently for her travel schedule!

My KH has zero pity for me staying locked while she travel, when we get back from our long weekend trip, she is going overseas for 10 says, and there is NO-WAY I'll be allowed uncaged, or having un-supervised erections anytime soon - she is experimenting with milking me, but besides getting the feeling of needing to pee, we not getting much success, and with T&D being rare, its going to be a long time before any relief is in sight.

Her version is that she wants to milk me rather than allow me a orgasm, or limit me to 1-2 per year - IF she manages to milk me successfully - she still feels just a little guilty, hence my being allowed to orgasm ONLY inside her every 2-3 months (and obviously clean her afterwards)....

[Aarkey]

My KH has zero pity for me staying locked while she traves.

That has been my experienced too. Both the women who I've had long term relationships with since discovering chastity seemed to always like to lock me up if we were going to be apart for a while.

Her version is that she wants to milk me rather than allow me a orgasm...

Good luck with it. As I wrote above, it takes some practice and experimenting for some of us to make it work.