How I spent my summer vacation – Episode 2

It was a normal Summer Saturday and Mistress Rosemarie had laid out my sissy maid outfit that I was to wear for cleaning the house this week. I am sure that every sissy is made to clean her Mistress’s House and that was normal.

Let me rephrase that. Dressing as a sissy maid for Mistress Rosemarie and other Mistresses of “The Institute for Cross-Dressing Punishment” is never normal. The Mistresses always seem to have a way of making every simple cleaning day an adventure in reminding me of what it means to be a sissy maid. There always seems to be corsets, cuffs, sissy clitty cages, diapers or something terrible and uncomfortable to hinder my cleaning routine. At least today I was given my 2″ heels instead of the 5″ heels (when I am really being punished) to wear.

Well I dressed as instructed and presented myself to Mistress Rosemarie for the “sissy-do” list of cleaning chores that she would require me to do.


On this particular Saturday in August Mistress Rosemarie took it to a new level of sissy maid punishment for my sissy cross-dressing ways. She decided that if her house needed cleaning that my house probably did too! I was uncertain by what she meant by this, so she explained. She thought that a complete wash and cleansing of my interiors was also necessary and why not accomplish both at the same time. I started to cry when she explained further to this not too quick or bright sissy.

I was to be given an enema while I cleaned the house.

Oh My Gosh, I could have fainted on the spot. She told me to stand in the corner while she went to the Ladies room to prepare my enema. She returned with a bulging two quart enema bag as I stood quietly dreading this. I have been given enemas by Mistress Rosemarie and they always gave me cramps and they hurt so much.

She instructed me to bend over, pick up my dress, crinoline, pull down my panties and pull the butt plug out of sissy vagina leaving it dangling for future insertion at the end of the enema. Then I gasped as she plunged the sissy enema douche nozzle into my sissy vagina. I clenched my vagina cheeks to keep the douche nozzle in place because the consequences of letting it fall out are unmentionable.


I was told to fix myself and to look like a proper sissy maid. Mistress Rosemarie had not released the enema, but the big enema douche nozzle hurt my sissy vagina. I stood there for several minutes as Mistress Rosemarie took pictures for my sissy scrapbook. It is so humiliating to know that I have a sissy scrapbook that she keeps and is my ultimate threat of embarrassing exposure. I stood as still as I could dreading the start of my sissy maid duties for the day.


The 2 quart enema was attached to my wrist with a pink scarf and was told that I would have to thoroughly clean all of the Ladies Rooms in the house to Mistress Rosemarie’s satisfaction. She then released the enema clamp on a very low setting so that it very slowly started to leak into my body. She had put very cold water in it and in a matter of minutes it started to give me cramps and it hurt terribly. I was sent on my way to clean the bathrooms. It was very difficult cleaning as I received my enema. It took me a long time and my sissy tummy hurt a lot, but I finally finished the first bathroom. I called for Mistress Rosemarie to inspect, but as usual it did not meet her stringent requirements as she thought the toilet still looked dirty. I started to protest but stopped as she reached for the bar of pink Camey soap. I hate the taste of pink soap.

The enema had emptied and completely filled me. She told me to bend over and she took out the enema douche nozzle and shoved the sissy vagina plug roughly back in as a let out a tiny squeal. That did bring a smile to her face. I was told to redo the entire bathroom.

About half way through cleaning the toilet my cramping was terrible and I started to leak. By the time I finished the toilet I had leaked enough to leave a small puddle of enema fluid on the floor and Mistress Rosemarie having watched and I am sure anticipating this told me to sit on the toilet and allowed me to release the rest of the enema fluid.

I thought I was done, but she informed me that since it was not lady like for even a sissy to have an accident on the Ladies Room floor that I would have to start over from the beginning. She filled the 2 Quart enema bag again and we started from the beginning.

This continued all afternoon as I could not hold my sissy enema while I cleaned. Finally, thank goodness, Mistress Rosemarie relented and I was allowed to clean the Ladies room without my enema attachments. Some 30 minutes later I finally finished.

I started to cry as she told me she liked the way I responded to her new cleaning protocol and we would clean the Ladies Rooms once a month with this new routine. The normal routine of cleaning the Toilets each week did not seem so bad anymore.

sissy billy – sissy cleaning maid to Mistress Rosemarie


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You should consider yourself lucky that Rosemarie allowed you to have an accident on the floor. How much more disgusting would it have been if you would have been wearing full panties and hose which would have let the leaks run right down your legs?

Yes Mistress Katzenburg, you are correct. At the time I thought that it was the most horrible thing I ever had to do. I realized as I was writing this episode and exposing my punishment that Mistress Rosemarie was very kind. She was within her rights to have continued my sissy maid training until I was able to clean the Ladies Room and in hindsight might still be trying to do it today. The thought of having my insides cleaned by leaking into my panties and dripping and collecting down my leg inside my pantyhose is icky, disgusting and would have been totally humiliating.

The truth is that I did learn a valuable lesson about doing my sissy maid chores each Saturday and not complaining. Mistress Rosemarie must have noticed the difference because I have not been made to perform my cleaning in such a manner since August. Each Saturday it is a lesson I think about and pray that I have pleased her and do not have to repeat this lesson in servitude and humility.

I thank you Mistress Rosemarie for this valuable lesson and training.

sissy billy

You are welcome sissy billy. You should consider yourself very fortunate to have Mistresses like Mistress Katzenburg and myself that are very considerate, conscientious and probably much to lenient in your training and punishment for cross-dressing.

Mistress Katzenburg, thank you for the thought of having her contain her inability to perform her simple cleaning activity. That would certainly have been disgusting and degrading for her. She did look like she was having some terrible cramps though. How amusing a little sloshing around would have been.

Just remember my little sissy, this is for your own good and you do deserve it.

Dear sissy billy,

I wanted to know how many times did you get an enema that day?

Hello pieclown,

I got a total of three enemas that day. Mistress Rosemarie was not mean though. After I leaked the first time she did allow me to sit on the toilet and empty myself the best I could. If you have ever had two enemas in a row you know that you can not empty it out totally in one sitting. The second enema hurt so much because it filled me up a lot more then the first and when I leaked I leaked a lot and had a lot of cleanup to do. The third enema was really really bad and before I exploded on the floor she told me to go to the bathroom before I really messed up her bathroom. She was kind enough to let me completely empty myself after that and then I finished my sissy maid cleaning chores.

This was a hard way to try to clean the house and hope I don’t deserve to get another double or triple enema any time soon.

Mistress Rosemarie does like to give me enema punishments because she likes me to feel the cramping like girls do and they embarrass me as she makes fun of me. Most times if I am naughty I only get a single enema though.

sissy billy

    Thank you for sharing sissy billy. I have not had a double enema, but I have had 2 quart enemas, fleet, and barium. The last 2 were for medical reasons. Yes, the process of becoming empty is quite time consuming. I have read that mistress would give their sub and enema and leave, knowing the sub would be busy for a while. Thank you again for sharing your adventures.

you sound like you had a wonderful summer, and I adore your cute dress and the way its makes you look so sweet in your pictures. I havent tried enemas as yet but they sound both painful but enjoyable. Hope to learn more about you soon.


maidsadie xx

Hello sissymaidsadie, they can be painful and they are enjoyable in a limited fantasy. As a punishment or part of an extended activity or assignment, not so much so.

sissy billy

Oh my gosh, pardon my rudeness, Welcome sissymaidsadie. I do not think I have conversed with you in the past.

sissy billy

thank you sissy billy pleasure to meet you xxx

Good luck in your assignments sissymaidsadie, I am glad to have some additional sissies in training.

sissy billy

I love the second picture with you bending over. So telling! I have yet to have an enema but am very interested in it.

Hello sissymaid jillian – I sounds great and exciting and sexually arousing in a fantasy life, but be assured it is unpleasant and it hurts and if held for any length of time the cramping is very very unpleasant. Much like a women’s period would feel like I imagine.
sissy billy

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