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A further restriction
#1
As I have described, I am subject to a three weekly milking, always on a Sunday morning, purely for hygiene and long term health purposes. Last night though, as part of a wider discussion about my place in our relationship, Mummy let me know that there would be changes to the regime from now on. Here is what she proposes from now on.

In future, my milkings will be dependent on the roll of a dice. Each Sunday morning I will throw the dice, ensuring that it lands out of sight.  The outcome will be as follows:-

The first week, actually, there will be no roll of the dice.  Mummy explained that it would be too indulgent to have consecutive milkings, and probably more than my little winky could stand.

The second week, I need to roll a 6. The third week a 5 or 6, and so on, so I am guaranteed a milking by the 7th week. The clock resets after each milking.

When I wake up on Sunday, Mummy will give me one of my big boy sweeties. She has explained in the past that these make my winky slightly less floppy, and so makes it easier for her to finish the milking quickly and with least effort.  I won't know at that point whether of course I will actually be milked.

After the dice has been rolled, regardless of outcome I will be laid on the bed, and be prepared. This will involve being dummied, having my satin milking hood put on me, and my hands mittened and tied out of harms way, to prevent any naughty attempts to play with myself. Only then will I be uncaged.

Mummy says she will then start to give me my special feelings.  She will carry on until she senses that my milk is frothing up inside me. If the dice roll wasn't in my favour then she will stop the milking, let the frothing subside, and, after a period of contemplation, I will then be caged and unhooded.  Mummy says that I might find that this gives me a heightened degree of urges for the next few hours, especially as I have taken a sweetie, but that is all part of my training to control myself.

If I am fortunate in the dice roll then Mummy has explained that in future, she will stop her milking just as I get to the point where I cannot stop the milk frothing over, but really want her to carry on. She says that as I only produce a tiny dribble of milk these days, it won't make much difference to the amount she will then spoon feed me, but will stop her getting her hands messy in future.

So I'm now waiting, with nervous anticipation, the first trial of my new milking regime this Sunday. Somehow I don't think it's going to be an improvement from my perspective.
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#2
A very clever idea, I will give her that. It sounds like a lose-lose situation irrespective of whether the dice comes up in your favour the way I have interpreted it as she doesn’t intend leaving you fulfilled either way.  Wink 

Be sure to let us know how you get on though as it sounds like it might be a ‚Äėdifferent‚Äô experience if nothing else.
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#3
Full marks for creative games.
Always in strict uniform
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#4
Has Mummy considered wearing latex gloves and covering her fingers and palm with Deep Heat/Dencorub/Bengay? That way, whether you win or lose the roll of the dice, your little winky will feel Mummy's hand for the hours afterward?
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#5
(09-24-2020, 11:55 AM)wailer Wrote: Has Mummy considered wearing latex gloves and covering her fingers and palm with Deep Heat/Dencorub/Bengay? That way, whether you win or lose the roll of the dice, your little winky will feel Mummy's hand for the hours afterward?

Ouch!  I might just forget to mention that suggestion to her... Big Grin
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#6
(09-24-2020, 03:18 PM)Sissy Celeste Wrote:
(09-24-2020, 11:55 AM)wailer Wrote: Has Mummy considered wearing latex gloves and covering her fingers and palm with Deep Heat/Dencorub/Bengay? That way, whether you win or lose the roll of the dice, your little winky will feel Mummy's hand for the hours afterward?

Ouch!  I might just forget to mention that suggestion to her... Big Grin

heheh, I've read about such treatments from Victorian Governesses as part of a boy's punishment for "self abuse", I never would want it though Smile
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#7
(09-25-2020, 05:18 AM)wailer Wrote:
(09-24-2020, 03:18 PM)Sissy Celeste Wrote:
(09-24-2020, 11:55 AM)wailer Wrote: Has Mummy considered wearing latex gloves and covering her fingers and palm with Deep Heat/Dencorub/Bengay? That way, whether you win or lose the roll of the dice, your little winky will feel Mummy's hand for the hours afterward?

Ouch!  I might just forget to mention that suggestion to her... Big Grin

heheh, I've read about such treatments from Victorian Governesses as part of a boy's punishment for "self abuse", I never would want it though Smile
Would be interesting to try and watch
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#8
A very creative method of milking indeed and certainly for a sissy once every 7 weeks is quite ample. It seems that under this regime you will never experience a full blown orgasm, but always produce enough sissy milk for a feeding! The life of a petticoated sissy! Thank you for sharing!
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#9
You are very welcome sissyjamieanne.

And so, an update on the first day of the new regime. Mummy had a couple of further twists to the process, which I can only guess whether she deliberately kept from me earlier in the week or had thought of subsequently. Neither, as you can imagine, made the experience any easier for me.

The first came during preparation time. Having had my nappy removed, and been hooded, dummied and my hands secured, it was explained to me that because of the extended session I was about to have, Mummy was concerned that there might be a little mess from my botty. So she told me she was going to put what she called an inflatable sausage inside me to prevent any leaks. After insertion, it was duly pumped up until I will admit I let out a little squeal (or would have done if my dummy had let me).

So I rolled the dice, and although I didn't know it, I rolled a 3. That turned out to be more significant than I thought. I was taken to the edge, and as expected, left to contemplate my position for around 10 to 15 minutes. And then, to my surprise, it all started again, with one more pump of the dildo, which by then I had sort of got used to before the teasing started. And then a third time. By the end I was utterly exhausted, even after what seemed like a final downtime of around 30 minutes (most of which I spent wondering whether I was going to get a fourth helping of attention).

After that, Mummy unhooded me, took the dummy out, and thankfully also her "inflatable sausage", and explained what had happened. Because I rolled a 3, that was 3 less than I needed for the milking, so I was to have 3 sessions of being taken to the edge. I was so grateful not to have rolled a 1, as I don't think I could endure 5 aborted milkings.

Mummy did say how well I had done, as she put my cage back on and dressed me, and that she was very proud of me. She said that the experience was an essential part of my sissy training, and that I would get used to having my milk froth up and then back down again with lots of practice, which it looks like I'm going to be getting in future weeks. Next week I "only" have to roll a 5. Sigh!
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#10
I have had to use Icy Hot to give myself pleasure with. It is a wicked feeling, it starts of cool and feels good and you want to give yourself that pleasure. Than the heat kicks in and not sure what to do, continue on and have a painful climax or stop rubbing it in and no climax. In the end it is so rubbed in and you almost cry from the shear pain, for the next 30-40 minutes, the heat is so hot you can barely breath but you hope that cummy was worth it. After that time you can just feel the heat for about 2-3 hours, not uncomfortable just notice it.
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