Tag Archives: milking

Relief for sissy billy

I made a wish and Mistress Amber has granted it. I did not, however, ask what the price would be.

Now my wish has been granted and I must pay the price at the same time.

Mistress Amber has tagged this an assignment, I will tell you later if is a punishment. I seems like one. In hindsight I was to learn something and that is something private I will discuss with Mistress Amber.

sissy billy makeup Punishment for Mistress Rosemarie has been Posted and my basic feminine ensemble is based on Day 4.

I am to wear:

Wrist and Ankle cuffs, Clothespins on my nipples, High Heels, My sissy clitty-cage (May be removed when playing the Role of Kaya’s Master only), A lace up Corset, Panties, A Big Bra stuffed with the largest water Balloons, Diapered and wearing my Overstuffed Pink Plastic cover

Added conditions for this Relief

Higher High Heels, Bigger Water Balloons, More stuffing in my Diaper

Prior to the start of this Activity, I am to dump a 1 Quart pitcher of Cold Water in my Diaper. I realize now why Mistress Amber added this. My wish was to be very difficult for me to accomplish. My sissy-clitty shriveled up from the cold water.

The Cost of my Wish

I am to perform Kaya’s Video and I am to play both the Part of Kaya’s Master (My wish) and the part of Kaya (My payment for this wish)

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Relief for sissy billy

sissy billy has been very patient in her training, but has become a bit needy in the past few weeks. (I think this is why Mistress Rosemarie wanted her sissy to wear a clitty cage full time.)

I have been laying in bed trying to go to sleep and I have an enormous erection. I laid on my back so as not to have an orgasm. It has subsided, but I have only milked my sissy clitty the one weekend of the wedding punishment and that was as directed by the punishment. Since the end of March I have only made love with my sissy clitty that one weekend. I have been so careful because you said that if I did have an orgasm and milk was to come out that the punishment was something that I did not ever want to know about.

In that same email cautioning me not to milk my sissy clitty or else suffer a terrible punishment, you also suggested that I not wish for something that I might not like. I has been so long since my last orgasm, that I am willing to accept any consequences. Please Mistress Amber, I am wishing for you to give me your permission to milk my sissy clitty.

I am afraid of the consequences, but I am desperate for making love to my sissy clitty.

So, as requested, I am giving sissy billy what she thinks she wants. She is to dress up as she did in day 4 of her yet to be published clothespin punishment with a couple of changes and re-iterations:

  • High heels will be worn
  • The pink diaper cover will be super-stuffed.
  • One quart of ice cold water will be poured into the disposable diaper immediately after putting it on.
  • The bra will be properly stuffed—the balloons used in the recent pictures were not sufficient.

Once dressed, she will play both part’s in this video from Kaya. She will pull out her sissy clitty and perform the part of Kaya’s master. She will then pull the diaper back up and perform the part of Kaya.

sissy billy will post the results of this punishment before she is allowed to take the clothespins off. The remainder of the clothing will remain in place for six hours following the posting of her punishment.

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