Tag Archives: clothespins

Maggie Rae: Story Assignment 3—Back and Forth

Let me tell you about the worst night I’ve had in a while, and bear with me because I haven’t had nearly as much sleep as I should have. This week’s story assignment looked bad on its face, many of them do, but it’s not until you’re well into it before you realize exactly how terrible it is. The principle sounds simple enough—my assignment was to transfer pennies one at a time from a cup in one room in the house to a cup in another, with increasingly unpleasant additions as I went. Now, my place isn’t that big, and even spread out as far as possible, there were only about 15 steps between cups—not awful you say, that’s 30 steps per penny. Well, allow me to show you how wrong you would be…

Like most assignments, however, I started by laying out everything I would need beforehand… Ominous, isn’t it?

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SUMMER SCHOOL SESSION # 2 – WEEK 2 – CLASS STUDY OF THE EXPERIENCES OF A “SISSY GIRL PERIOD’

The Second Semester is dedicated to a class curriculum of “Sissy Girl” Home Economics. It is a learning experience of what to expect as a Sissy Girlie Cross-Dresser in preparation for readmission to “The Institute for Cross-Dressing Punishment”.

My second week course entails the experiences of a “SISSY EXPERIENCING HER PERIOD”.

The following course requirements are:

This week will be devoted to her “period” week. Learning to become a young Lady is critical to her Sissy Development. This course is under the guidance of “Auntie Flo”. “Auntie Flo” will send her reminder and daily assignments prior to the School Week. Attached is the “Period” Memo I received from “Auntie Flo”

Hello Sissy Billy,

I know that you believe your Monthly Menstrual Cycle is not due to start till Thursday, but Honey, sometimes it can come early and suddenly. So, unexpectedly it you will start your “Period” tonight.

“SURPRISE”

Tuesday, June 26, 2012

Tonight without warning it starts. Take 3 feminine laxatives immediately and drink a large glass of water every hour until 9:00 PM. I would suggest you put a Sanitary Napkin in your panties right away. Your cramping will start at 9:00 PM today. You will accept a full enema and refill each time you must go to the Ladies Room. Your nipples will also swell and throb. Nipple Pins for 15 minutes every hour. Continue to 11:00 PM and then you can try to go to sleep.

You should set your alarm for 5:00 AM and start your enema simulation of severe cramping for an hour before you may then start to get dressed for work. Since you feel bad, eating lightly is a must. You may eat you normal food, but I strongly suggest you help digest your Food by taking a tablespoon of Castor Oil with it. You better wear a Sanitary Napkin to work tomorrow.

Wednesday, June 27, 2012

A Bad Day today. Cramping is bad – Drink water all day. This will continue Menstrual Bloating. You should wear maxi pads for the day changing if necessary. Tonight is more cramping enemas for the entire night. When the cramps are too much you may go to the Ladies Room. However, you must refill and re-administer another 2 Quart Enema as usual. Repeat the process until you go to bed. – Your Sanitary Pads must be smeared with my special “Period” discharge
– Attach clothes pins for 15 minutes before going to sleep.
– Normal Food is OK, but it must be taken with Castor Oil as well as feminine Laxatives before going to Bed.

Thursday, June 28, 2012

Your cramps are stopping, but your Sanitary Pads must be smeared with my special “Period” discharge and you should insert Tampons all day.

Friday, June 1, 2012

Your period is ending, but continue to wear protection today.

Good Luck my young Sissy Girlie Lady.

Best wishes, Auntie Flo
See you next month.

And So, on Tuesday my “Period” began. It is true that I have been having my “Period” for a number of months now, but it is humiliating to tell about it in a post.

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How I spent my summer vacation – Episode 4

It has been quite a while since I have related another of my summer experiences with Mistress Rosemarie. I was supposed to do this on a regular basis, but forgot and to be honest put it off since my summer vacation was mostly humiliating with many embarrassing activities, trips and things with her. Well the year is almost over and as all things do it has caught up with me big time. This past summer often found me in hot water, but none more so then when I tend to embarrass Mistress Rosemarie in front of one of her friends.

The specific day was a nice warm day in August and we were suppose to go to the beach with one of her friends from work. This was always fun and mostly stress free for me since Mistress Rosemarie was seldom inclined to embarrass me in public by having me do girlish things. It was Saturday and when we went to pick up her girlfriend she explained that she had her period, did not feel good and really did not want to go to a sandy beach. I had been looking forward to this and I lost it. I cried and before I thought, I said I didn’t care if she had her period, she could stay home and we should go without her. No sooner were the words out of my mouth and the look on Mistress Rosemarie’s face told me I had crossed the line. I knew it was insensitive and I knew I would regret it.

Mistress Rosemarie left the room with her friend and when they came back smiling they told me it was about time that I had my first feminine period. I blushed a deep red, but knew better then to say a word. Well out came the feminine sanitary products and their fun began and my misery started. Her friend seemed to feel better that she had a girlie sissy to commiserate with. I was very much embarrassed by this day that I had hoped never to have to relay it for all to hear.

I somehow never learn my lessons though. Last week I made the same awful insensitive mistake again with another one of her friends because it interfered with us going out to a party. She was totally livid and then she remembered my unlearned lesson from this past summer.

Well, this has now become – How I spent my summer vacation – 4 and also how I spent my Christmas vacation – 1.

This past Tuesday Night I came home to find Mistress Rosemarie with both of her girlfriends that I had embarrassed by being insensitive about their periods. They reminded me about how I had said to all of them that I did not see what the big deal was about a little stomach ache and having to wear a rag between there legs. Well, Mistress Rosemarie then smiled and said that it was about time that I realized what a big deal it was.

I was led into the bathroom and spread out on the counter was my impending lesson.

I was to have my first feminine period and I would certainly learn what the big deal was after 24 hours. I groaned, but there was no way out of this now.

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Pieclown: Halloween Assignment 2009

I received an email Tuesday October 27, 2009 from Mistress Amber Shummer. This is an exert from the email.

Since it is Halloween, it is time for some dress up with the following assignments.

pie clown – Something creative (anything but a clown)

Notes:

  • No masks are allowed
  • Costumes should be as creative, yet as uncomfortable as possible.

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sissy billy’s Makeup Punishment for Mistress Rosemarie

Mistress Amber never forgets:

Out of the blue she noted that I had failed to complete and actually never started a punishment that Mistress Rosemarie assigned me for embarrassing her. My original punishment was for taking the sissy way out of accepting a punishment by saying that I could never wear clothespins on my nipples for more then 1/2 hour. I accepted the fact that I had ignored this punishment and accepted the punishment from Mistress Amber that I was now required to complete it. I accepted and started my punishment.

Day One:

Mistress Rosemarie intended for me to place clothespins on my nipples for just 1/2 hour on the first day. Since I was already wearing wrist and ankle cuffs per my Standing Training rules I put the cuffs on also. I also had lots of my panties to iron. I had not had clothespins attached to my nipples for several weeks now and I forgot how much they hurt. I did complete my half hour and felt good that I had done so. My nipples were already sore, but I knew the real punishment would be Day three and four.

There was one huge mistake I made. I did not tell Mistress Rosemarie that I was completing the assignment she had given me. She was so mad that I went and hid in my room. When I finally got up the courage to go back downstairs she had calmed down, I thought. All she said was that the conditions had changed and we would be starting again tomorrow. Then she sent me to my room to think about how much trouble I was in.

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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.

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

sissy billy’s Standing Training Rules had only been issued last week, but already I am in trouble and must confess to Mistress Amber. I love a pretty negligee, but I can never sleep at night while wearing one and that should be easy for a sissy. This was true with my diaper training and now more so with the selected activity of having to wear wrist and ankle cuffs while in the house. I sleep in the house, so therefore I should wear them to bed as a reminder that I am the sissy in training and Mistress Amber is in Control. Mistress Amber has thoughtfully tried to help in my learning to sleep as a sissy by constantly assigning sleep time activities. Since last week I have worn the cuffs while in the house, but have had to remove them to sleep. Last night I laid in bed until 1:00 AM trying to learn to wear them and sleep, but could not. I took them off. Today was a Holiday, so it was not bad. I do need my sleep during the work week though. Per Mistress Amber’s assignment, I am to propose a punishment and then carry it out if I am naughty. The last time I tried to do this in my Modified Wedding Punishment it was a disaster for me as I thought I could accomplish a lot and impress Mistress Amber, but to no avail. Thankfully she took pity on me and made my punishment less severe. This time I think I will propose punishments more in line with my abilities to accomplish them, I Hope.

The only portion of the activity that I failed to obey was the cuffs and only at night. sissy billy would like to propose the following punishment scenarios.

In the case where sissy billy does not wear cuffs so she can sleep during the work week, this should be a lesser punishment as she does need to work and get some sleep and so is only a naughty sissy.

Since sissy billy needs her sleep, she can remove her cuffs before bed. However, to reinforce that she is still a sissy, on the nights she does not wear her cuffs, she will no longer be treated like a sissy, but like a sissy baby. Baby’s do not take showers in the morning, but sissy baby’s take baths and so sissy billy will take a bath and a sissy when taking a bath should always take a bubble bath. Tomorrow sissy billy will start taking bubble baths each morning she does not wear her cuffs. Additionally, since sissy billy is still trying to learn to wear her sissy clitty cage, she will be required to wear it whenever she is wearing her cuffs. sissy billy will owe four additional bubble bath mornings when this assignment is completed.

The second part is for a very naughty sissy. Since this activity may go on for quite some time, I will offer some options for myself so as to vary the punishment. The following punishments are also punishments that sissy billy has had in the past and does not like. So by offering a variety, she may learn how to deal with her punishments.

On non Work Week nights like last night when sissy billy did not need her sleep and did it for her convience, the following punishments will be carried out the next day before she goes to sleep. There are six punishments and only one will be awarded to her when she is a very naughty sissy. sissy billy will take a single dice, roll it and whatever number appears will perform that punishment. Listed below are the punishments listed 1 thru 6

  1. sissy billy is to wear High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a thong and stand in a corner for 10 minutes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  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.
  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.
  4. sissy billy is to put a bar of Pink Camay soap into water for 5 minutes so it is wet, soapy and gushy, get ready for bed by removing her sissy items and shove the Pink Camay into her mouth for 1 minute (enough time for the gooey soap to fill her mouth). She is then to take the bar of Pink Camay soap out, but is not allowed to spit any of the gooey soap in her mouth out, but must keep it in her mouth for another minute, get into bed and then she is to swallow it. The soap taste will remind her to think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  5. sissy billy is to put on High Heels, a water balloon stuffed big bra, cuffs, sissy clitty cage, and a stuffed diaper and rubber diaper cover, her teal Jumper to package it all and then using the treadmill in the basement walk for 1 mile waddling like Mistress Amber likes and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night.
  6. This is a Mistress Amber lucky – out of the goodness of her heart – get out of punishment card. There is no punishment, but sissy billy will kneel by the bed for 5 minutes before going to bed and think about being a naughty sissy and how she can become a good sissy by wearing her cuffs at night. sissy billy gets to roll again and double the length of the punishment she gets on that roll. once completed, sissy billy will go to bed with all of her cuffs locked on anyway.

For last nights indiscretion sissy billy rolled the dice and the number two came up. I performed the punishment and will document it to Mistress Amber.

Of Course Mistress Amber has the option of modifying or changing any of the punishments above as well as deciding the length of this assignment. The next non work day is Saturday and so the very naughty sissy scenario will be decided after Friday night. Hopefully I do better this Friday Night.

Updated by Mistress Amber on May 28, 2009

pieclown: Potty Mouth – Cleaned Up – IV

My most resent punishment has me paying for not doing all my treatments. I am to wear panties and a bra, every day until I get this done. I was to add panty hose on Monday, and girdle on Wednesday, if I did not post all four punishments. Me and my clown ways screwed up and thought if I started on time would not do this. Well if I had started on time and did it everyday I would b done before I need to add more clothing. This photo is from Tuesday.

Here I added pantyhose.

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pieclown: Potty Mouth – Cleaned Up – III

Third time is not a charm.

My most resent punishment has me paying for not doing all my treatments. I am to wear panties and a bra, every day until I get this done. I was to add panty hose on Monday, but I misinterpreted Mistress Amber’s instructions. She said if I started Thursday, I would not need to add any more clothes. Had I done everyday since Thursday, I would have been done on Sunday and not needed extra clothes. Well here is what I did wear.
This photo is from Sunday.

This photo is from Monday.

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pieclown: Potty Mouth – Cleaned Up – II

2nd Round

My most resent punishment has me paying for not doing all my treatments. I am to wear panties and a bra, every day until I get this done.

This photo is from Friday.

This photo is from Saturday. Mistress Amber said in a recent conversation, that I should do a photo in a sexy way. So I snapped one normal photo and a little sexier.

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pieclown: Potty Mouth – Cleaned Up – I

My most resent punishment has me paying for not doing all my treatments. I am to wear panties and a bra.

This will go on until I get my potty mouth cleaned.

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Stacee Skye: Another Beginning

Apparently Stacee Skye didn’t realize that I would be waiting for her when she got home from work. She complained that she wasn’t ready and had to take the lawn mower to the shop. I told her it was fine. She could take it to the shop while wearing a bra and panties without any problem. And the penis harness for good measure. I think she has a clue what is coming since I sent some clothes pins with her “just in case”. I don’t think there is any question that those will be on when she gets back.

Update at 6:22pm: After all of her complaining, she sure wasn’t outside very long before wetting herself. I wasn’t planning on keeping her in a wet diaper very long, but I don’t have anything else planned, so I guess it will have to do. I way even eventually let her take her clothespins off, but not too soon. I need to get them toughened up because Mistress M has mentioned some big plans for them.

Update at 6:45pm: Stacee Skye seemed so happy when I had her take pictures of herself taking off one item of clothing at a time. She didn’t even complain when I only left her in one high heel for a while and the breast forms bounced wildly as she ran to get in place for the picture: at last the clothespins were coming off. Perhaps that is why she looks so sad kneeling next to me wearing a corset, a diaper and those clothespins. She just has not learned her lesson yet.

Update at 7:02pm: When I put some weights on the clothespins and they were pulled off, I wasn’t feeling evil enough to put them back on. (I mean I could have, since she obviously didn’t do a good job putting them on in the first place, but I’ll save more clothespins for later.) So I left them off, but a bra and forms back on, dressed her in her KDPi t-shirt and sent her back outside. It’s not that bad: she doesn’t have on any bondage gear (yet) and the t-shirt mostly covers the diaper. Besides, it should be dark in 3 hours or so.

Getting Started is Half the Trouble

In helping wives become Mistresses to properly train their husbands, I have found that getting started is usually the hardest part. Once the training has started, it will continue without a problem–but that initial boost is the issue.

For many of the training sessions with Mistress M’s husband, I have ensured he was dressed and bound before she arrived home to “start” the punishment. It has worked well, but it is not always a practical solution. So here is the situation and how I would start thinking about the punishment. Good learning.


Mistress M is planning a training session this weekend, on Sunday, after going to church. She will be dropping her daughter off at the baby sitters and then sending her mother, who is in town for a visit, off to a double feature.


There are a number of ways this could play out, depending on the timing of the church, the movies and the baby sitter. Here are some of the options (in an approximate order of severity). Of course, there are many tweaks that can be made to these choices, but that exercise is left to the student.

  1. After sending her mother to the movies, Mistress M admonishes her husband to be dressed and ready for training when she returns. (In about a half hour, which should be sufficient time for her to get dressed.)

  2. After sending her mother to the movies, Mistress M sends her husband to the baby sitters. She is waiting when he returns and pulls into the garage. She has him strip, then leaves clothes for him to dress in the cold garage and hope neighbors are not looking through the windows.

  3. After sending her mother to the movies, Mistress M has her husband get ready to go to the baby sitter. He is to put on a corset (black), penis harness, g-string, girdle panties, tights (pantyhose) and bra under his other clothing. Depending on the level of his complaints, wrist and ankle cuffs can be locked on, clothespins can be clamped on the nipples, a remote vibrator can be used, etc.

    Once he is dressed, Mistress M can send him to the baby sitter, so she can stay home to prepare, knowing that he will hurry back, or they both can go.

  4. The same as number 3, but Mistress M sends her husband upstairs to change as soon as they return from church. He can then spend the next hour avoiding his Mother-in-Law (until she goes to the movies) lest he be found out.

  5. After coming home from church, Mistress M sends her husband upstairs to change out of his church clothes. Unfortunately for him, she has the full training outfit laid out and he is quickly dressed. She leaves him hogtied, blindfolded, ear plugged and hooded in the bedroom, while she goes to visit with her mother. She returns later, after her mother has gone to the movies and she has taken the baby to the sitter.

  6. After sending her mother to the movies, Mistress M sends her husband upstairs to change into the full training outfit. He is blindfolded, ear plugged and hooded in the bedroom, then leashed and led to the garage, where he is tied into the back end of the car for the trip to the baby sitters. Once they return home, the real training can begin.

  7. The same as number 5, but when she comes to release her husband, he is untied long enough to bed led to the garage and re-tied into the back end of the car for the trip to the baby sitters. After a start like this, she should happily submit to any training that is offered.


So those were just the ideas I had–I’m sure you can come up with some tamer and some much more evil than I can. Happy training.

pieclown: Mid-Assignment Punishment [Results]

So, pieclown finished her punishment, and in record time.

She had clothespegs on her nipples:
Plum

a decent set of forms:
Plum

and a nice skirt and blouse combination:
Plum

When she was tied to the chair:
Plum

she did a fair bit of writing:
Plum

So the punishment was completed successfully? Absolutely not. I’ll finish grading it in a bit, but I wanted to make sure she had time to defend her work first.

Stacee Skye’s Sentencing

In a comment via Yahoo 360, sissie maid jenna said that Stacee Skye should be required to write “i am a worthless slut” 100 times with perfect handwriting before being allowed to go to bed.

I like the intent of what maid jenna is trying to do, but I think it could be spiced up a little bit. So I came up with this sentence for Stacee Skye to write when this punishment is implemented:

my name is stacee skye, the big titted slut puppy,
a panty wearing bimbo sissy with huge fake breasts who needs to  
   have her cuffs and collar locked on her to keep her from removing them,  
   be gagged to prevent her constant back talk,  
   be corseted to improve her figure,  
   be forced to wear the highest heels to improve her gait,  
   be corrected with a wooden paddle to be reminded Mistress is always right,  
   have clothespins applied to show it can always get worse, and  
be trained  
   as a sissy maid to learn the importance of serving Mistress,  
   as a pain toy for Mistress' amusement,  
   as a pain slut for Mistress' whipping practice,  
   as a oral sex slave for Mistress' pleasure,  
   to sleep bound so Mistress can sleep as well, and
on occasion,  
   have a plug shoved up her ass to remind her of her place, or
   be diapered to show how bad it could get,
all with the ever-present threat of public humiliation.

I think this might get the point across a little better. Is there anything that I have forgotten?

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