Tag Archives: pictures

sissy billy’s Standing Training Rules – A SUCCESS – 2009-May-31

A Success:

Mistress Amber has been so kind to allow me to tell you about the first small success I have had in my first two months of trying to become a worthy sissy of the “The Institute for Cross-Dressing Punishment”. This is only a small one night completion of a punishment, but I am very proud of it. I want to thank Mistress Amber in my training in becoming an obedient sissy.

Saturday Night – 2009-May-30:

It is Saturday night and I am home for the evening. I have put on my ankle and wrist cuffs and my sissy clitty cage. I have also put on my new pretty Lilac Peignoir. I have included pictures so you can see. Isn’t it really pretty and feminine. I just love it. As instructed by Mistress Amber when I dress in my sissy clothes at home I am to wear my big bra and I have made bigger water balloons that please Mistress Amber stuffed in my bra.

I have decided that tonight I am not going to just give in and accept a punishment and hope for the best. I am going to succeed tonight, not only in wearing my cuffs as the assignment dictates, but also in wearing my pretty peignoir all night. I am not going to take them off even if I lay awake all night long.

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sissy billy’s Standing Training Rules – Punishment – 2009-May-30

How I have disappointed Mistress Amber

Confession: On Friday Night, which was a non work week night, I tried to sleep with my cuffs on, but failed to keep cuffs on my wrists and ankles for the entire night. I was very tired and thought that I would be able to go to sleep, but at 1:00 AM after laying in bed for two hours I was still wide awake. I then gave in to my sissy weak willpower and decided to take off my cuffs.

Punishment: I rolled the dice and the number 3 came up. Therefore the punishment is as follows: Punishment # 3. sissy billy is to make a bedtime snack of Level 1 and 2 baby cereal, vegetable, fruit and while wearing cuffs, sissy clitty cage, Stuffed bra and a thong eat the whole snack. After she has finish the baby snack she may take off her sissy items and climb into bed with a 4 oz bottle of baby formula and drink it. The sour taste of baby formula all night should remind her of being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.

Completed Punishment: I got out of bed, kept my sissy clitty cage on and put on a red thong, kept my cuffs on, put on and stuffed with water balloons a big bra and then I went down stairs to the kitchen to make my sissy baby snack. I used only Level 1 and 2 baby food and made baby cereal, added baby vegetables (squash and carrots), added fruit (Plum and peaches) and then poured baby formula into a baby bottle. I added too much baby formula to the baby cereal and it was really soupy and looked even worst then the last time I had to eat baby food. I also made more then the snack portion required by mistake, but once I had made it I knew I would have to eat what I made. I then went back up to my bed and sat on the edge of the bed to start eating my snack. Finally when I finished the food, I took off my sissy items, took my sissy baby bottle and lay down in bed to drink it and go to sleep. I took appropriate photo’s to document my punishment for all to see. I still had problems going to sleep because the sissy baby food snack was sitting in my already stuffed stomach from dinner. I could still taste the icky baby food and since I was not allowed to wash my mouth out our brush my teeth, the baby formula taste coated my tongue and mouth. As I lay in bed trying to go to sleep with the awful taste of pasty and icky sour tasting baby formula in my mouth, I thought about why I am such a sissy and can not successfully complete the assignments that Mistress Amber gives me. I will try to be a better sissy in the future. I should be thankful that Mistress Amber is helping me to become a better sissy and I will try to please Mistress Amber more each day with my training.

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sissy billy’s Standing Training Rules – Punishment – 2009-May-25

How I have disappointed Mistress Amber

Confession: On Sunday Night, which was a non work week night, I failed to keep cuffs on my wrists and ankles when I was in the house.

Punishment: I rolled the dice and the number 2 came up. Therefore the punishment is as follows: Punishment # 2. sissy billy will stuff a bar of wet Pink Camay soap into her mouth, put clothespins on her nipples, High Heels, cuffs, sissy clitty cage, and a thong and stand in front of the mirror for 5 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.

Completed Punishment: I put my sissy clitty cage on with a red thong, kept my cuffs on, put high heels on, placed a clothespin on each nipple and then shoved a fully wet Pink bar of Camay soap into my mouth. I took appropriate photo’s to document my punishment for all to see and then faced the mirror for 5 minutes as timed on the kitchen timer. While I stood facing the mirror for a full 5 minutes I recited to myself a part of one my punishments previously given to me by Mistress Amber. Mistress Amber and the other Mistresses and Ladies of ‘The Institute for Cross-Dressing Punishment’ are always right in their attempts to correct a sissy like me. I should be thankful that Mistress Amber is helping me to become a better sissy and I should learn by my mistakes and correct them.

Be Careful What You Say

When you are posting comments, you should always be careful what you say, as it may comeback to bite you. For instance, Stacee Skye commented “Are you sure that is a diaper? It looks more like a pair of old gym shorts to me.” While technically correct, she was out of place. So I reminded her what a real diaper looks like. This picture was taken after I poured two quarts of ice cold water down her diaper:

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pieclown:Atonement (Bra Show)[UPDATED]

Hello All. It was several days after I was ask to leave the salon school, that I finally did my bra show. I knew I have better duplicate what the conditions to my best ability. I had been clothed pinned and plugged at the salon, so I redid this while I started to shave my chest and below the belt.

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Sucks to Be Me

Back in August, after Mistress Amber dressed me in a diaper, she further dressed me up in a couple of different outfits.

After each one, she sent me to the basement with a camera to “practice” Continue Reading

Pink and Plasticy

After Mistress Amber got finished playing dress-up, she took pictures to show Mistress M, that yes, I show up dressed up exactly like she had sent me. I’m not sure what else she was expecting.

And then she decided to punishment me for being “late”. Continue Reading

pieclown: Pantied n Hosed

As part of my Hard as a Rock assignment, I was required to wear panties every day, until the assignment was done.

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pieclown: Big Ball Slut

Hello all, this posting is in response to the assignment Hard as a Rock. Not the AC/DC song Big Balls.

Some of you that have read through the Institute know that this is also based on the on idea of Heavy Knockers. I was required to get some bowling balls and use them instead of balloons. My thought was I would be checking thrift stores and second hand sports equipment. I took a chance and check Craig’s List

I got lucky and found the bowling balls on sale for five dollars each.

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Let’s Go

Just before Christmas, I showed up for a quick training session and gave Stacee Skye a fairly simple task: get dressed so that you can go outside. And she did a fairly decent job of it:

Ready to Go

So I said, “Let’s go” and she replied “Let me get my coat.” Big mistake. Continue Reading

pieclown: A New Dress

In this picture from back in December, pieclown shows off her new dress and asks “Does this complete this part of the punishment?”. Since I can’t remember which punishment it was, I guess so.

pieclown's new dress

She sent in two pictures, but in the other one she decided not to wear any forms. (Perhaps she though I would like it anyway?)

pieclown’s apology

I got a note back from missy maid the other day:

mistress amber,

missy maid is very sorry to hear that all of miss pieclown’s pictures and video were uploaded since missy maid cannot understand why miss pieclown cannot follow the directions. missy maid was right to think that miss pieclown would find a way to cheat. missy maid is also upsets with mistress amber because missy maid knew that miss pieclown would not complete her apology correctly.

missy maid

I have already sent my apologies to missy maid, as I forgot that I must give pieclown very explicit directions. While I told her to “Get yourself dressed up, proper feminine makeup required, with properly sized and weighted breast forms…properly corseted, plugged, packaged and ball gagged,” I did not specifically mention this time that the pictures must reflect this. So there is a whole lot of pictures of her meditating and writing that all pretty much look the same.

Meditating Writing

Was there a digital clock in any of the pictures? Not a chance. (Well, there was a computer added timer, but that wasn’t quite the point.) And apparently, my directions should have said “Take readable photographs (or scan) the original apology letter.” There’s nothing like an apology you can’t read.

I did manage to catch a couple of pictures with pieclown all dolled up, so I will be sure to post those soon. As soon as I hear back from missy maid. (Maybe pieclown will feel sorry for missy maid and send some full body pictures. I am not holding my breath.)

Why I Love Working with Stacee Skye

One of the reasons that I love working with Stacee Skye is that she is so damn predictable. Everyday she will come home from work and head straight to the bathroom. Today she found me waiting with a large diaper.

Note that it is still small enough for her to get on pants that are normally two sizes too big, so its not close to too big. So I’m going to send her out to the back deck for a few with her pants and a tight shirt to show off the small (D-cup) forms I had her put in. Maybe if she is good I will let her take the forms out before I send her further in the back yard to get ready for later tonight. And if she’s not, then I predict it will become much harder for her to waddle about her house pretty soon.

Update 1 (6:10pm):

Of course, once I told her she was going out on the deck, she put up a fit and said she wasn’t going out there in her loose shirt and pants. For once I agreed–I sent her out the side door (which has a bit more protection from prying eyes) wearing just her diaper and a way too small shirt. Wasn’t she cute?

Update 2:

As when enlarging the size of breast forms, when putting on a diaper, bigger is always better. How big is too big? Well, I haven’t found out yet, but as long as it still fits through a hula hoop, its probably too small.

Of course, since I wouldn’t want Stacee Skye messing up this nice large diaper, I made sure that there were a couple of disposables underneath. So think of this one as just for show. (As in showing off to neighbors and friends and anyone else who cares to look just what a big sissy Stacee Skye is).

Stacee Skye: Bitch Baby

Here’s a blast from the past: Stacee Skye starring as “Bitch Baby”. She “can’t” remember when she took the picture, but thinks it was sometime between Jan 1996 and Oct 1999. Yeah, way to narrow down the range there. The pictures quality is due to a poor original: she took an out of focus picture of herself in the mirror and then kept in hidden for quite a while–until now.

Bitch Baby

Judging by the size, I think she may have had a pillow between her legs as a part of the diaper. Her breasts are duct taped into place. And she has “Bitch” written down one leg and “Baby” up the other. In permanent marker. So what do you think of her get up?

pieclown: Alphabet Soup Assignment Results

And now for the results:

















How did she do?

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