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Chastity
#31
(05-18-2021, 07:29 AM)Silymaid Wrote: Miss Elise, a quick short hand job, wearing washing up gloves, ruined, then locked back up as soon as possible, ice cold flannel etc...need to minimise the after glow/pleasure as much as possible. This helps returning sissy to their submissive ways.

One day missed for you, 28 days missed for sissy....strict regime you have...will certainly keep sissy on their toes to perform!
That description of a milking is almost spot on what I get these days. The weeks I am not finished off I am teased until the denial is torment. But when I am eventually milked the event is very businesslike, administered in the way a nurse might, and usually over in less than a minute with a ruined climax that leaves me equally frustrated.
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#32
I like the idea of Nanny or Mummy making sure that we know that making squirties is just another thing that they control completely.

And then making it clear that for them it is as clinical as an enema before hand, and a thorough bathtime scrubbing, unlocking and shaving and cleaning, before locking us up again.

Making us kneel on all fours over our toddler potties, while they snap on their nursing gloves, before inserting their fingers to add lube to our bottoms. Looking back to see them putting on the harness, attaching the large rubber cock, modelled on their boyfriend.

Then squealing as it slowly but forcefully penetrates our bottoms and starts to be pulled back and then forced forward, fucking our sissy bottoms.

Eventually, the milking has its effect and even though our peepees throb in their little cage, they cannot get hard, but our miserable squirties leak out into the potty.

Then the feeling as our dummy is unstrapped from our mouths, rubbed in our silly sissy squirties before being strapped back into our mouths.

Quick, clinical and complete, it's over for a week, with a locked peepee, plugged bottom and thick nappies once more.
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#33
A friend of mine can make me cum just by rhythmically spanking my bottom. He puts me across his lap and makes sure he gets right between my legs with each spank.

I wonder if your sissy might find himself cumming in the same way? If he did then he’d not only get no pleasure from his release, but actually be punished as he releases. You could maybe put him into a pair of those discreet incontinence panties as he’s spanked, so that his little dribble is safely contained in his panties.
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#34
Found a flaw in my plan to release him every 4 weeks, when I reached the 4 week point I just didn't feel like it. I told him that it remains That he must give me daily good times but I would release him only when I feel up to it. So he did 36 days. I cuffed his hands in front of him so he could reach it, bent him over the sofa on his knees, got my strapon on and took the cage off. He hates the strapon and can't usually get hard when I use it. But I wasn't really trying to be fair. The idea was to be tough on him. 25 minutes of that or thereabouts, I washed him and put his cage back on. The plastic sheet I use was quite wet but he says he didn't have the standard orgasm. It was a bit disappointing for him.
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#35
I’m not sure him feeling disappointment would necessarily constitute a failure here (it might even represent progress) - unless of course it didn’t fulfil your own requirements  Wink
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#36
(06-01-2021, 12:22 PM)Elsie Wrote: Found a flaw in my plan to release him every 4 weeks, when I reached the 4 week point I just didn't feel like it. I told him that it remains That he must give me daily good times but I would release him only when I feel up to it. So he did 36 days. I cuffed his hands in front of him so he could reach it, bent him over the sofa on his knees, got my strapon on and took the cage off. He hates the strapon and can't usually get hard when I use it. But I wasn't really trying to be fair. The idea was to be tough on him. 25 minutes of that or thereabouts, I washed him and put his cage back on. The plastic sheet I use was quite wet but he says he didn't have the standard orgasm. It was a bit disappointing for him.
Sounds like he got a very thorough milking, which is what us naughty toddlers deserve. He was lucky that you let him out of the cage for it. I hope he thanked you for being so nice to him.
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#37
(06-01-2021, 12:22 PM)Elsie Wrote: Found a flaw in my plan to release him every 4 weeks, when I reached the 4 week point I just didn't feel like it. I told him that it remains That he must give me daily good times but I would release him only when I feel up to it. So he did 36 days. I cuffed his hands in front of him so he could reach it, bent him over the sofa on his knees, got my strapon on and took the cage off. He hates the strapon and can't usually get hard when I use it. But I wasn't really trying to be fair. The idea was to be tough on him. 25 minutes of that or thereabouts, I washed him and put his cage back on. The plastic sheet I use was quite wet but he says he didn't have the standard orgasm. It was a bit disappointing for him.

36 days is a good length of time. I found when my sissymaid was extended to once every 2 months her attitude became very much more obedient and willing to do anything to please me. She was nearly climbing the walls after two months, as it should be. Her attention was solely on me and my pleasure and it helped a lot with her submissiveness as well!
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#38
(06-15-2021, 01:01 AM)Strictwifeamber Wrote:
(06-01-2021, 12:22 PM)Elsie Wrote: Found a flaw in my plan to release him every 4 weeks, when I reached the 4 week point I just didn't feel like it. I told him that it remains That he must give me daily good times but I would release him only when I feel up to it. So he did 36 days. I cuffed his hands in front of him so he could reach it, bent him over the sofa on his knees, got my strapon on and took the cage off. He hates the strapon and can't usually get hard when I use it. But I wasn't really trying to be fair. The idea was to be tough on him. 25 minutes of that or thereabouts, I washed him and put his cage back on. The plastic sheet I use was quite wet but he says he didn't have the standard orgasm. It was a bit disappointing for him.

36 days is a good length of time. I found when my sissymaid was extended to once every 2 months her attitude became very much more obedient and willing to do anything to please me. She was nearly climbing the walls after two months, as it should be. Her attention was solely on me and my pleasure and it helped a lot with her submissiveness as well!
So good to see so many ladies taking charge of their sissy's bits!  I am loving the power and control....   Ten days is longest soo far........  I think i enjoy using it more and more........  Will pop it on or off at a moments notice at my whim.  Keeps him guessing and eager to please..
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