My Mistress will allow me to cum however I like | You Decide!

[GodDragon]

So, I just got the news that I may cum however I like on valentines day.
Now, I could just go the easy route, use my fleshlight or my hand and call it a day.
It is a very enticing idea, but, I want to consider other options. Actually haven't had anything fully wrapped around my penis in months. So had no full stroking, fleshlight or anything.

I am mostly kept in (inverted) chastity cages, edged daily, 1-2 caged ruins a month. I am not sure if I want to humiliate myself by "wasting" that opportunity/might even do the right thing by doing something more fitting for a sissy slave. We play with feminization a lot, anal, plugs, analgasms, chastity etc. Even a full orgasm itself is a gift.

So, why not ask you lovely people and make it interesting? You can suggest a specific idea, or vote for a generic one in the poll.
So here are the poll options with an example:

Very pleasurably! -> Just as I like, hand stroking, fleshlight or similar.
Pleasurable, but limited -> Palming, fleshlight but with manual "fucking", magic wand on lowest level etc.
Caged, pleasurable -> Vibe on big cage or similar
Caged, decent -> Vibe on inverted cage or similar
Caged, (pathetic) sissy style -> Multiple options. A full anal orgasm with a big dildo, or fucking a fleshlight with a strapon, or stroking a dildo instead of myself etc.

Let's see what you guys think is the right choice to do here. I am really torn myself

[SleeplessSub]

I think you will need to hold a second voting round to decide the exact way......

[GodDragon]

I think you will need to hold a second voting round to decide the exact way......

Well, I'd need some more ideas to include then Toys wise I can offer basically anything. Spiked chastity instead of an inverted cage would also be an option. Apart from that and the like simple anal gasm with a big, uncomfortable toy, using a strapon to fuck a fleshlight and cum from the humiliation, light pressure on groin, or stroking a strapon/dildo instead of touching myself, as seen in various clips, are things that come to mind. But otherwise, I am not sure yet what else would be similarly cruel. Something with CBT maybe.

[47dahc]

I don't have any experience with an actual dom/mistress, or the etiquette that goes with it, or your relationship with yours for that matter, but why not just fuck them or have them help you release. You said you haven't had anything wrapped around your cock in awhile. If that's the case, I would want something warm and moist and not controlled by a machine or app. Maybe a nice long edging session maybe with a prostate massage, and then after you release, they make you eat it.

[GodDragon]

I don't have any experience with an actual dom/mistress, or the etiquette that goes with it, or your relationship with yours for that matter, but why not just fuck them or have them help you release. You said you haven't had anything wrapped around your cock in awhile. If that's the case, I would want something warm and moist and not controlled by a machine or app. Maybe a nice long edging session maybe with a prostate massage, and then after you release, they make you eat it.

Yes, surely that is an option for the pleasurable ones.
The previous person in this thread though was hinting at the fact that the "pathetic" option is already winning by a mile, and thus I was asking of further examples for that option.

Generally in the case of the caged options, especially the bottom one, it would be part of our dynamic to have me humiliated and denied the pleasure of getting to touch, even more so sex, being stroked or similar. I haven't had anything around my cock, because I wasn't allowed to, not because I couldn't do so for other reasons. Like our dynamic involves chastity and the withdrawl of anything pleasurable. Edging we do a lot but anything like actually getting to touch, let alone stroke or smth. is very rare, if not ever the case. Like the past stroking, which is a big reward - maybe once a month - has been one finger edging outside of the cage.

Like, not getting to stroke, not getting penetration with my penis and spending most of the time in chastity, edging with like one finger, or if I am lucky a vibrator. That is why I said the obvious great option is to go with the pleasurable option, but, that is like the one not in line with the rest. Not that I wouldn't like it, just that I thought it would be fun to ask the internet instead, since I was torn between getting an actual great orgasm and going with what is more in line with the sub space etc.

[edger477]

I was torn between getting an actual great orgasm and going with what is more in line with the sub space etc.

Then don't ask the internet, just let her decide. Tell her what you want but that you want more to give yourself to her, and to do it in way that is most fun for her.

[GodDragon]

I was torn between getting an actual great orgasm and going with what is more in line with the sub space etc.

Then don't ask the internet, just let her decide. Tell her what you want but that you want more to give yourself to her, and to do it in way that is most fun for her.

I mean, the most fun for her in that case was giving me the choice, and let alone me bringing up the idea of considering a bad orgasm was the fun for her. And since I was torn, we ended up gamefying it and making it a poll which in itself is a "BDSM game".