Tag Archives: sissy-billy

Embarrassment at the Bar

sissy billy sent me this quick story about how she was almost humilated at a bar during her [current punishment][1]:

> Several of us sat for dinner in a corner of the restaurant and I was the first to sit and found a place in the corner thinking I would be less exposed. The women quickly surrounded me as they usually do. I think they all have a protective spot in their heart for me the past few years. One of the girls is a lot younger then I and she had her new boyfriend in tow. My best friend’s wife who is the most protective sat next to me and the single woman (a good friend of my wife) and is my age sat on the other side of me. I do enjoy how protective they are and it does give me a feeling of being included. My thoughts went back to one of your statements in my wedding punishment about what they would think about having a sissy among them. I was inwardly embarrassed, but also wondered the same thing.
> Well – the embarrassing moment came towards the end of the night. I was kind of trapped in the corner and had just got my check when I lost control and started to urinate in my diaper. I could not stop it and it felt like I soaked it. I put my hand in my lap and the whole front of pants was wet. I sat there frozen as everyone else continued to talk. I was afraid to move and as they all got up to leave I tried to hide myself as best as I could and get out of there. I don’t think anyone noticed as I had to give the mandatory kisses and hugs (No close hugs this night) to the women and handshakes with the men. When I got home and could look in the mirror it did not look as bad as it felt. I had dark pants on and you could hardly notice the dark spot. Lesson to be learned is not to wear light pants with my diaper.

I asked her why her plastic panties (which I required her to wear) didn’t take care of this issue. Apparently she misunderstood the rule (“Both cloth and disposable are fine, but the plastic cover must be worn over them.”) and didn’t wear them. Since the doesn’t want to wear the panties, maybe she should get some more absorbent diapers. [This brand][2] holds over four liters of liquid (depending on the size). I could have her pour a gallon of water down her panties before going out and she still wouldn’t overflow. I will keep that in mind.

[1]: http://institute.cdpunishment.com/2009/05/a_very_smooth_move
[2]: http://kckmedical.com/index.asp?PageAction=VIEWCATS&Category=27186

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).

[1]: http://institute.cdpunishment.com/2009/05/a_very_smooth_move
[2]: http://institute.cdpunishment.com/2009/05/avoiding_humiliation

– ~ — • — ~ –

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″]

Avoiding Humiliation

sissy billy [commented that][1]

> I lack the courage to expose myself to my doctor. I just would be so humiliated. I am such a sissy baby and you are right that I would pick the punishment in private. I will send you pictures of what a sissy baby will endure instead of humiliating herself in front of her Doctor.

So she is working though her punishment prior to actually shaving. In addition to this, she has a few other events coming up that she will be attending as a diapered sissy *after* she’s shaved:

* Two days of playing golf (May 9 and 10)
* One time at church (May 9)
* One nice dinner with her Mom (May 10)
* One wedding (May 15)

I just wonder what these people would think if they knew there was a sissy baby among them.

[1]: http://institute.cdpunishment.com/2009/05/a_very_smooth_move#comment-2407

A Very Smooth Move

Last night [sissy billy admitted][1]: “I deserve punishment for this basic mistake of not knowing the proper name. What is my suitable punishment?” The punishment is very simple and will handle an different whining complaint that she made: sissy billy is to shave herself **tonight** from the neck down—sissy babies shouldn’t be hairy at all.

[1]: http://institute.cdpunishment.com/2009/04/taking_our_name_in_vain#comment-2369

If sissy billy wishes to put off this punishment, which I am pretty sure she does since she has an annual check up with the doctor next week, then two conditions will be added, First, each night until she decides to shave, she is to follow the directions in the following paragraph:

> sissy billy is very sorry that she did not take the time to properly learn that the name of this institution of correction is known as ‘The Institute for Cross-Dressing Punishment’ and not the other name that sissy billy wanted to call it. sissy billy will endeavor to use the name of The Institute properly in all future communications; will be punished much more severely in the future for this type of infraction; and will recognize that her Mistresses are always right in attempts to correct her. sissy billy also realizes that she is dressed up as a double stuffed sissy baby (with a water-balloon over-filled large bra, a regular diaper, a grossly overstuffed pink plastic diaper cover filled with all manner of absorbent material, and punishment level high heels) and has a wetted down bar of pink Camay in her mouth of her own accord because she chooses to put off her punishment. By writing out this paragraph five times each night before going to bed, sissy billy is learning a very important lesson about ‘The Institute for Cross-Dressing Punishment’. sissy billy is learning that Mistress Heavynne Yeardleigh, Mistress Amber Shummer, and the other ladies of ‘The Institute for Cross-Dressing Punishment’, are committed to punishing and humiliating all of their sissy clients, especially when the sissy wants to delay a punishment. sissy billy is also learning that when being trained by Mistress Heavynne Yeardleigh, Mistress Amber Shummer, and the other ladies of ‘The Institute for Cross-Dressing Punishment’, the punishment will only get worse the longer it is delayed.

Secondly, after she shaves, she will multiply the the day of the month (of May) that she decided to shave, and spend that many days following with the following punishment rules:

* She is to wear her clitty cage, panties and pantyhose to work.
* The only toilet she may use is the one at her job.
* She is to be diapered as soon as she arrives home from work, and remain so until she leaves for work again. Both cloth and disposable are fine, but the plastic cover must be worn over them.
* If she loads her diaper, she is allowed to change herself after [gagging on a cock][2] for 10 minutes. (Every sissy should be required to practice this way.)
* If she just wets her diaper, she is allowed to change it after 30 minutes.
* Pantyhose may be worn to help her compress the diaper if she needs to leave her house.
* And since she needs to pretty and likes to wear a negligee to bed, that will be allowed if she is wearing some appropriately [heavy duty cuffs][3] on her wrists and ankles—just so she doesn’t forget this is a punishment.

So if she waits until the 7th to shave, she will spend 14 days, from the 8th through the 21st under these rules. Or, she may surprise me and just shave tonight. Stranger things have happened.

[2]: http://www.extremerestraints.com/penis-gags_154/
[3]: http://www.extremerestraints.com/bondage-gear_10/strict-leather-premium-locking-cuffs_199.html

Taking Our Name in Vain

In the middle of one of the first email exchanges that I had with sissy billy, I had to gently correct her on the name of this institution:

> Our name is not “The Institute for Cross-Dressers Punishment”. The
proper name is printed at the top of EVERY SINGLE WEB PAGE!

And of course, she couldn’t help but reply:

> You must think me an idiot Mistress Amber.

Well, she should have helped, because that was the wrong thing to say. So, I gave her what I thought was a suitable punishment:

> Your punishment is as follows:

> * You are to wet down a bar of pink Camay
* You are to dress in a negligee, different than your previous punishment.
* You are to put 10 clothespins on your body (at least 2 on your nipples as
before)
* You are to shove the wet bar of pink Camay in your mouth
* You are to write out (longhand) the following sentence 50 times:
“sissy billy is very sorry that she did not take the time to properly learn
that the name of this institution of correction is known as ‘The Institute
for Cross-Dressing Punishment’ and not the other name that sissy billy
wanted to call it. sissy billy will endeavor to use the name of The
Institute properly in all future communications; will be punished much more
severely in the future for this type of infraction; and will recognize that
her Mistresses are always right in attempts to correct her.”
* If a mistake is made in the sentence, it should be lined out AND the
total due is increased by 2.
* If the soap leaves the mouth for any reason, it is to be soaked in water,
replaced in five minutes AND the total due increased by 10.
* Sentences shall be written in ink on lined paper.
* The line before each sentence shall be a status line containing
+ Date
+ Time
+ Number of this sentence
+ Total number of sentences to complete

Then she really started the whining:

> I don’t think I could get it done all at once. It will take me hours.

(Apparently her day is much shorter than mine.) I was even nice enough to offer her some relief in having to finish her punishment (which she declined to take) and her performance was miserable:

> As I can tell you finished two sentences (plus two incomplete) and had
twenty added for dropping the soap. My count shows you adding 24 sentences
to the 50, completing 2 for a total of 72 remaining. That is a spectacular
failure.
>
> You should realize that the standing rule has been that a failed assignment
is given again until it is repeat correctly. In addition, a punishment is
added for the first failure.
>
> I will let you know when I come up with a suitable punishment for this
miserable failure.

And though it has taken a long while, I finally have a punishment suitable just for her.

Welcome sissy billy

Since I started my European trip, I haven’t had much time for working on the site. It this time a new sissy has joined the fold:

![](http://cdpunishment.com/institute/images/2009/04/sissybilly_090405-002s.jpg)

With her reading comprehension and whining like a baby, she will fit right in.

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