I was looking at some chastity caption pictures yesterday and a few of them went somewhere along the lines of, “I want to get you so desperate and frustrated so I can find out what you will offer to do just to be allowed an orgasm.” It got me thinking, what have people here offered their key holders to be allowed to cum? I know some will see this as a strange idea because their chastity is about being locked at the whim of their key holder, but I want to hear from those who are locked and really want to cum.
It doesn't work that way in our relationship. If I so much as ask when I'll be released her response is to smile sadistically and promise me it will now be that much longer as a result. Begging just makes her laugh... to a point, and then she hushes me and tells me I need to shut up if I ever want to be released. I would imagine offering her something would probably offend her. If she wanted something she would just order it.
In my case begging outside of a session and when not told to do so, would be punished. That could range form a good talking to, increased non ejaculation time or testicle slapping while ejaculating after being milked in the cage, The worst I had, mistress removed my cage during a normal session, inserted a solid penis plug/cum stopper, refitted the cage. She then set about what I thought was a normal session albeit with a cum stopper fitted, this was always removed before she ejaculated me, on this occasion she, didn't. Mistress kept going, and said don't ever ask to ejaculate again. I was in real fear and oh my god, if you've ever ejaculated with a cum stopper in you'll know what I mean! I never did ask/beg again ever.
Begging or bargaining would get me nowhere ether, at any time if I did madam would just laugh at me, and if I kept at it she would just ignore me, and not respond at all. I did once offer her £1000 to have sex with me again, I had the cash in my hand there and then( I’d sold a car), and she turned me down. The next day after I got in from the bank to deposit the money, madam, laughed and poured out she had the money any way and she hadn’t had to lift a finger! I hadn’t thought about that!
I don't have anything to bargain with my Wife already knows I will do anything for her: I'm allowed to ask only. Requests for full sex or performing oral on her are always denied when in chastity.
Begging or bargaining for me whilst I’m locked would get me further from having an orgasm. Mentioning the very thought of it, my cage or my desire to have sex gets me more time locked up. My pleasure is simply down to her, when she wants it.
I see a difference between begging and bargaining. I can totally understand why begging would get most people nowhere, and isn’t really what I meant by my initial question. I was thinking more along the lines of the bargaining being led by your Mistress/key holder. What if your Mistress/key holder asked you what you would do to be allowed to cum? That’s different from begging in my view. It’s more about how desperate you have become and what sort of things that would normally be outside of your comfort zone might you now be willing to endure to be allowed that orgasm?
This I could imagine. She loves to tease, and I could see her initiate such a conversation where she probes me to find out what I would be willing to do. I would see that in more of a fantasy teasing session though (e.g., "Would you suck a cock for me?"), and I don't think it would be something where she would actually plan or schedule my release based on my responses.
I get teased a lot and sometimes, while teasing me, She will ask what I would be willing to do if....... but I now know better than to reply with anything other than "whatever you wish ma'am!)
I once begged by saying that I would eat my cum if she allowed me to orgasm. She refused. I have never begged again. Occasionally I ask (not beg). Sometimes she says yes, other times no (which I LOVE).
That’s more along the lines of what I was thinking. You say she would t plan anything based on your responses but you never know...
Oh, I totally think she might plan to make me do the things I say in response. I just mean that it might or might not actually change her plans for when I get released.