sissy billy attends a wedding

sissy billy wants to be able to [suspend her punishment][1] on the last day since she will be attending a friends wedding and she wants to [avoid humiliation][2]. (Of course, if she had just shaved earlier, then it wouldn’t have been a problem to begin with. ) So I had her come up with a suitable punishment so she would be able to take off her sissy diaper once she got up from bed on the 15th. The following is what she came up with (with my changes in _italics_ and strike-through).


– ~ — • — ~ –

sissy billy is to return to her room immediately after the reception is over and _milk her sissy clitty into her diaper. The she will_ put on a diaper, rubber diaper cover and attach ankle and wrist cuffs _and a collar, all locked on,_ to reinforce the severity of the punishment. She is to bring the rubber cover with her to the hotel room to protect the bed because she will not be able to leave the bed until morning no matter how much she soils herself.

She will get up in the morning and _milk her sissy clitty and then_ clean herself and put on a new diaper to wear to the brunch. She will remain in diapers for the remainder of the punishment. After the brunch, she is to return home and commence a full 24 hour punishment as payment for being allowed to go to the wedding. The punishment will be continuous for the 24 hour period with no sleeping allowed.

The following 24 hour schedule is general and will be modified by Mistress Amber with options of Mistress Amber’s choosing. sissy billy is to document in a diary the description of each punishment section, the start and completion time of each segment of the 24 hr agenda with pictures that Mistress Amber will dictate as being necessary.

**12:00 to 2:00**

Arrive home and change into attire as dictated by Mistress Amber. _sissy billy will strip off everything but her diaper, lock on the wrist cuffs, ankle cuffs and collar. Then she will stuff her 4XL diaper pants to over flowing, put on her large bra, fill out the forms with water balloons (doing a bigger job than she has done in the past) and gag herself with her cock gag. She will clip her wrists together and clip her ankles together and then not be allowed to stand until this phase is over.

Write a letter of apology for requesting this modification, express gratitude that Mistress Amber allowed sissy billy this modification and write several times the agenda of the next 24 hr period laid out by Mistress Amber until sissy billy knows this agenda by heart.

**2:00 to 6:00**

Humiliation in public that sissy billy did not have to endure during the wedding with her friends. sissy billy is to go on a sissy girl shopping afternoon. She is put on her sissy clitty chastity, panties, pantyhose and a bra (unstuffed) and is allowed to put on whatever other clothes she feels necessary to conceal her sissy attire. She should spray a small amount of perfume on her like a girl would do just to remind her that she is a sissy even though her sissy clothing is hidden by boy’s clothes. She is then to drive to the next town and purchase feminine items as listed by Mistress Amber. (Items of Mistress Amber’s choosing such as lipstick, nail polish, make up, pantyhose, sissy clothes and whatever other embarrassing feminine needs that Mistress Amber can think of) She is to buy only one item in each store so that she is humiliated each time in each store. She is not to buy more then one product at a time.

**6:00 to 8:00**

Dinner – sissy billy is to eat and drink only what Mistress Amber has listed on the menu. sissy billy is to supply to Mistress Amber (If Mistress Amber approves this agenda and requests) by Sunday night (5/10) a list of healthy foods that sissy billy does not like and sissy billy will learn to like these foods in an attempt to make sissy billy get healthy and loose weight. Mistress Amber will add to this list things that she feels are good for sissy billy.

Mistress Amber will also prescribe fluids (Particularly Fluids that sissy billy does not like – since this is a punishment) continually through the night. At no time during this punishment is sissy billy allowed to use the bathroom.

_sissy billy will be allowed to eat any Level 1 or Level 2 baby food, baby cereal, and baby formula. These are the only foods that will be permitted for the duration of the punishment, and fasting is **not** an option._

**9:00 to 10:30**

Exercise to wear off dinner. sissy billy is to go for a one hour walk wearing undergarments as directed by Mistress Amber. To assist with loosing this weight from Dinner, sissy billy is to give herself an _retention_ enema of the type _submitted by her and approved_ directed by Mistress Amber and then go for a walk. Should sissy billy mess herself, she is not to stop, but must complete her walking assignment.

**10:30 to 11:00**

sissy billy is to take a shower and clean up and is allowed to relax and rest for this time period. _During her shower she will confirm that she is as hairless as when the punishment began, and adjust accordingly._

**11:00PM to 3:00 AM**

There should be a midnight snack as chosen by Mistress Amber

House Cleaning:
sissy billy is to dress as directed by Mistress Amber (Maids outfit, dress, _high heels, cuffs and collar, super stuffed 4XL_ diaper and _properly filled large_ Bra, or whatever Mistress Amber chooses). She is to thoroughly clean the house from top to bottom without resting. She is to make a list of everything that she cleaned, take pictures and Mistress Amber will decide whether she cleaned thoroughly enough or will have to repeat this cleaning next week.

**3:00 to 3:30**

sissy billy is allowed to rest for thirty minutes. This rest period should be in a manner that pleases Mistress Amber and does not have to be a true rest period for sissy billy. _sissy billy is to go outside to get some fresh air, still dressed for cleaning. A few picture will be taken._

**3:30 to 9:00**

Miscellaneous punishments of Mistress Ambers choosing. _Since sissy billy will not have finished the cleaning by now, she will continue doing that. If she thinks she has finished, then she can scrub the kitchen floor and the bathroom toilet and floor with a toothbrush._

**9:00 to 10:00**

General cleaning of whatever was messed in the house and sissy billy is to clean her self up.

**10:00 to 12:00**

sissy billy is to put on her Sunday best suit with whatever undergarments _(lacy g-string, pantyhose, locked on ankle cuffs)_ Mistress Amber directs and attend a church service. During Church sissy billy is to think about her punishments and be grateful that she has a Mistress like Mistress Amber who is taking an interest in her training and resources of ‘The Institute for Cross-Dressing Punishment’ to assist her in this training.

_Only_ If all of the above segments are completed and documented, will the punishment will be noted as complete. sissy billy is immediately _return to her cleaning outfit above, then_ sit at the computer and send off documentation to Mistress Amber _by correctly making a post with all applicable pictures on the website_ before she is allowed to rest for the rest of Sunday.

– ~ — • — ~ –

So, does this sounds like a fair trade? (Of course, even if sissy billy is getting the pointy end of the stick, it will still be considered fair since she made the proposal to begin with.)

[poll id=”8″]


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Oh my Goodness Mistress Amber. I submitted this proposed modified punishment as a number of possible punishments for your choosing and asked that you pick from them what was appropriate. I did not mean that the entire punishment should be substituted for not having to wear the diaper during the wedding and in particular soiling and changing it during the wedding. I proposed the modification and hoped you would consider this 24 hr modification to severe and asked that you would pick one or two that were harder as a whole then the diaper punishment, not the entire punishment. This entire 24 hour punishment is a punishment for a far more serious failure. With due respect to your wisdom and training Mistress Amber, I do not feel this total punishment is fair. Am I allowed to vote? If a majority of the votes are that it is not fair, does it then get modified again? Of course I will follow completely your decision and final instructions regarding this punishment. When does the voting complete and a final modified punishment issued? Thank You Mistress Amber. sissy billy

Mistres Amber. Do I still have the option of choosing the original punishment over this far more severe punishment or am I now destined to follow whatever this punishment ends up as a final version.

@sissy billy: You did not submit “this proposed modified punishment as a number of possible punishments for my choosing and asked that I pick from them.” In fact, you said ” I have proposed a modified punishment which is only one day in duration, but is many many times more severe then the one day punishment. I proposed a very severe modification with the hopes that Mistress Amber will agree that even my modified proposal is more than severe and that you would reduce the severity of this punishment and still grant my request.”

It sounds like you based email on false hopes. “I offer this 24 hour excessive punishment with the hopes that you accept 1 or 2 options as punishment in lieu of the Wedding punishment completion.”

I was very specific with my instruction. I did not ask for a smorgasbord of choices to pick from. I wrote, “You are to send me a proposed modification to the punishment which will
allow you the relief you desire AND provide me incentive to make it so”

“I will accept your decision as the proper punishment for a sissy requesting a modification of a punishment already given.” Or you can start a write in campaign for the various readers to vote you punishment as too hard.

@sissy billy: You have submitted a request for modification. It is being considered. It may be granted as is, may be granted in a modified form, or may be declined. You not longer have the ability to remove your proposal from consideration. Your comments will be taken under advisement.

Good Afternoon Mistress Amber. When I read the modified punishment this morning I was too quick to respond and have regretted it all day and was anxious to get home from work and correct my inappropriate responses of this morning. I apologize for my comments above and respectfully withdraw any comments or inferences that Mistress Amber did not react correctly to my proposal as submitted. Mistress Amber has always been correct in noting and documenting my mistakes and is always correct in her judgements and punishments of them. I stated my case improperly and as a sissy will accept any consequences from them. I will accept and implement the decision that Mistress Amber presents to me as a final punishment to my request for relief. Thank You Mistress Amber. sissy billy

[…] though the majority of people thought sissy billy’s punishment suggestion was fair, I have decided to change it up a bit–just to keep her on her toes (and to lessen […]

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