Still unable to cum in cage

I have only been able to cum a few times over a couple of years while caged, and there was a LOT of teasing with vibrators, etc from Mistress during that time.

Nothing specific was magic except maybe it had been well over a month between last time I did anything. The longer between orgasms ...sometimes...the somewhat unpredictable milking will happen with enough teasing for me.

 

Good! Maybe this should be your cue to stop.

 

What sort of massager do you have, is it a wand? If I use a wand, it can take quite a bit of time, but holding it against the cage will eventually induce an orgasm. Just be sure to hold it away the moment you know you've gone far enough to keep it ruined. Here's something you could try, hold the wand against the base ring, under your balls, that way you are vibrating both the cage and your balls, double whammy!

 

Wands are the way to go for me, when I'm allowed to cum in my cage. It works best if I use it between the bottom of the cage & my balls, similar to what Chaz69 said. I can make it work with the wand on top of the cage but it takes longer.

Having an anal toy at the same time helps immensely.

 

I see, it's not actual chastity either, then

 

Yes, sure, I like your remark. Albeit we should ask @Caged for life does he have a keyholder, what had keyholder commanded. It it was a command of a keyholder, then @Caged for life should definitely try to milk.

 

How long has it been since you last had an orgasm or ejaculation?

 

After a few months without any kind of orgasm or ejaculation you will be able to do it easily.

 

It's easy to blur the line... Two separate experiences, yet they can easily mean different things to different people.

Maybe first try bringing yourself to edge of an orgasm several times (by vibrating the cage and your balls).

This can be used as a warmup to get the juices flowing...

Once the prostate milking begins, keep repeatedly squeezing the PC muscle. The clear pre-cum that's leaking out will eventually start to turn white and cloudy...

Ejaculatory inevitability...

 

Nailed it!

 

The only way I get a prostate release is with my dick. Not my Wife’s dick, mind you. That’s locked.
It the same one i use when my Wife and have sex. So it satisfies both me and my Wife.

 

It took me some time but now I can cum in my cage by using my prostate massager or my dildo.

Here's how I do it, hope it helps:

First of all, I need to be very turned on (luckily that's not a problem). I have found out that these are the two positions that work best for me: laying on my back with my knees up, and sitting with my upper back against a wall and my legs up and open wide. I point the dildo/prostate massager towards my prostate so that it hits it just right and thrust it in and out. I usually start slow and increase the speed and pressure as my ass gets more and more sensitive. What also helps me cum is fantasizing while stimulating my prostate. And I think this is key in my case. Letting my imagination run wild, imagining that I'm being pegged, or whatever turns me on, but it's always something related to having my ass/prostate stimulated.

 

I’m new to the cage and my KH loves to milk my prostate while caged. Although I’m not shooting loads, it does milk me, meaning I start oozing cum. Not a lot but a noticeable amount.

Like others said, I also need to be really turned on and wanting it. It helps if I haven’t came in a day or two. I like a back/forth type motion on my prostate, like a touch and go but constant. Ive fantasized about being able to cum strictly from anal but it’s never happened, just tons of dribble and intense feelings.

For me to actually shoot a load within my cage, my penis head needs attention and I can stroke my cock while it’s in the cage. It’s a ruined orgasm but I still cum.

 

Quit trying. Since Miss A starting extending my lock ups, she likes to randomly tease and massage my cage and scrotum while locked. After about 7 days, she knows I will flow buckets while she does this…and that’s kinda the point. It’s definitely not a ruined orgasm but it is very pleasurable and lowers my frustration level for a few hours.

 

It’s worth noting, every time Miss A does this, she adds 5 days to that lockup period. It’s here way of giving me pleasure, but at a price. I’m flying out on business tonight so I will be free until I return home on Wednesday night. This will be my longest free stretch in months. Funny thing is, I’m not sure how I feel about it…

 

Did anyone read that in Agent Smith's voice? I was waiting for "ejaculatory inevitability Mr. Andersen"