Tag Archives: oral

Maggie Rae: Story Assignment 5—Hired Help

First off, I’d like to apologize to everyone—things have been a bit hectic, and I missed my usual Sunday deadline. I hope the amusement that you get from my suffering makes up for it a bit, and trust me, there was a good bit of suffering. This week’s story assignment actually managed to be less pleasant than Back and Forth, which I didn’t even think was possible. Like Back and Forth, I was again going to be transporting pennies, though this time as a restrained maid, and before I would be able to complete a penny I would need to perform oral service on a nearby dildo. Combine that with the same 1,000 pennies from the first time I did Back and Forth (which was never going to happen), and horrible consequences for failure, and you’ve got just the latest in my hellish assignments. First order of business, though, was to get dressed…

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Maggie Rae: Story Assignment 1—A Reckoning

As previously mentioned, tonight marks the beginning of my story assignment series—every week Mistress Katzenburg will be adding a new chapter to the overall story and I will be assigned a special assignment based on the week’s chapter. This being the introduction week, I got off relatively unscathed, but it was still an extremely unpleasant (and painful) experience. I know that as the story continues, my assignments will only get more and more humiliating—good for all of you, not so good for me. I don’t even want to think of where I’ll be in a month’s time…

Enough about worrying about the future though—here are the results of this week’s assignment.

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Aissgnment # 2A – “sissy billy’s” Ovulation Time

I am a Sissy that is now having her monthly “Period” at a regular Interval. Mistress tells me that it is part of a feminine cycle that I now “Ovulate” each month. I did not really know what this meant and was sent to research it’s meaning by Mistress.

A Women’s Ovulation time is the 2-3 Days each month when she is fertile. It usually falls in the middle of her Menstrual Period which I have now been experiencing. It is also the time of the month when the egg falls and she can become pregnant. Her hormones are at their peak and she feels her most feminine. It is also the time of the month when she will unconsciously dress her prettiest and have her strongest feelings to get pregnant.

At this time of my sissy life I certainly do not want to get “pregnant” or get anyone else “pregnant” and Mistress is “helping” me with contraceptive protection.

As a result of obsession with Cross-Dressing and the Training and Punishments the “Institute” has assignment to me, another phase of my Sissy Life begins.

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Make-Up Week for “Sissy Billy”

Last Week my Sissy had some personal issues and being the kind and sensitive Mistress I am, I relented and allowed her the week to settle her affairs.

However, as you all know, there are always consequences. Therefore she shall make-up last weeks assignments as she must also do her current week assignment.

  1. Complete her Post from Assignment # 3 – Fantasy Island High Roller Trip before going to bed tonight.

  2. Complete Assignment # 2A – Ovulation Time – this Tuesday, Wednesday and Thursday.

  3. Complete Assignment # 4 – Soap Testing designed as follows:

  • The Soap to be tested this week shall be a big white bar of Ivory.
  • Testing shall be per the previous guidelines.
  • Each morning with her shower using the Ivory, she is also to clean the inside of her mouth during her shower. She shall soap up her pink soft sponge completely and shove it in her mouth for the entire shower.
  • At night before going to bed, she shall test the Ivory as a soap-paste and brush her teeth thoroughly. Results are do next Monday night (It is a long weekend, so she gets an extra day) or sooner.
  1. Complete this week’s Assignment # 5 – Fantasy Island trip as a Cheerleader.
  • Special Cheerleader Dress Code for a Sissy. Everything Pink. Nail Polish, lipstick, Red Stockings and heels, pink panties, pink stuffed Bra, sheer top and of course her pom poms.
  • Her Bonus trip is a punishment for causing the team to loose.
  • First a paddling until her “ass” is pink.
  • Then a Cheerleader 2 quart enema.
  • With legs tied she is to stand in the corner of the Locker Room for one hour as her enema leaks out. No Cheerleader that I know would be able to hold it for an entire Hour. This should prove embarrasing as everyone watches.
  • Last she is to suck on the practice dildo for ten minutes and then lick the cheerleader practice vagina for another ten minutes.

Make up Weeks can be exhausting and non forgiving. Since our Sissy missed last weeks assignments and requirements she shall wear panties and pantyhose every day to work this week as a punishment.

“sissy billy” – I was understanding, but I have not talked with Mistress Katzenburg this week and am not sure if she will be. Do not be surprised if she is not as understanding as I and alters your assignments.

Your Summer School Associate Mistress

sissy billy’s Ovulation Time

Now that you are a young “sissy” Lady and are getting your monthly “Periods”, there is also a time of the month where you “Ovulate”. This is usually about two weeks after your “Period” starts each month and after consulting “Auntie Flo” and her menstrual Calendar, it is determined that you will be Ovulating from next Wednesday thru Friday.

This assignment (Let’s call it Assignment 2 A) is in addition to your Assignment # 4 – More Soap Testing which will be issued this weekend and start on Monday.

Assignment # 2 A – sissy billy’ “Ovulation”.

This is a time when a Lady is most susceptible to getting pregnant. We do not want that to happen to you or for you to impregnate anyone else. So your assignment is as follows.

  • You are to research and write a paragraph describing a Ladies Ovulating Time.
  • When at home (I think you are safe when out in public) you should wear protection. You are to put your sissy clitty cage on and wear it whenever you are home.
  • A Lady usually feels sexy and pretty during this time. You should change as soon as you get home into a pretty feminine outfit and then before bed put on a pretty Negligee and wear it until morning. You should wear something different and pretty each night.
  • Each night you may (since this is safe and no impregnating can take place) practice your oral technique on your dildo and your vagina.
  • After three nights and your “Ovulation” has ended – you are to remove you sissy clitty cage, put on a condom and relieve three nights of pent-up sexual frustration filling it as much as you can. You are then to snip the end and in front of your Mistress such your juices till it is empty.

This should protect your “sissy” virginity.

Fantasy Island – Smurfed All Night Long

As related in my previous adventure – A Smurfy Centerfold, the Smurfette’s convinced Mistress that I should stay the night and meet them in the Fantasy Island Smurf Park on the far side of the Island.

I did not like the sound of that, but as usual I had no choice and I was led by Mistress back into the Sissy Salon.

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Fantasy Island – High Roller

I ask myself how I ever got myself into this mess. All I did was request a few months off to take care of some personal Business. My re-instatement has become long and trying. The Moral of this all is that all sissy clients of “The Institute for Cross-Dressing Punishment” should realize and accept that they are naughty and that this should never be a part time experience, but must be dealt with on a continual basis. I will think twice about asking for a little time off the next time. But then again, I never seem to learn quickly. However, back to the task at hand.

I am restarting my assigned trips to Fantasy Island. This time the script is dictated by other clients and Mistress Katzenburg.

As I approach the Mistress of Fantasy Island she informs me that she wants to go to the Fantasy Island Casino and will teach me to be a High Roller. I am whisked off by her assistants to dress for the occasion.

I am to wear a slinky dress, a large bra and forms and a matching thong. I present myself to the Mistress.

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In a Row — Alien Invasion — Maggie Rae’s Results

For our most recent assignment, In a Row 2: Alien Invasion, we were to dress up as alien invaders of Earth—very confused alien invaders I might add, with our primary tactic of invasion being a lingerie photo-shoot and the crashing of a Halloween party. I’m not sure I get it either, but that’s the story, and I’m sticking to it. In the words of the assignment:

”To dress as the buxom alien for the lingerie shoot you will be painted from head to toe with a colored cream make-up (you get to pick the color, which cannot be white), then in your largest bra (stuffed) and panties.”

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Fantasy Island – 12 “A Little Girl’s Birthday Party”

As I walked up to the Mistress of Fantasy Island my mind was racing. It seemed whatever I wished for, the results of my wish were not what I thought they would be. Actually they had mostly been disasters and were truly painful and humiliating. What should I wish for?

Then I thought, how bad could a little Girl’s Birthday Party be. She dressed up in a pretty Dress and had fun with her Girl Friends and got lots of Presents.

Settled – I asked for it to be my Birthday and to attend a Little Girl’s Birthday Party in my Honor.

As usual, Mistress smiled that smile that always gave me chills and dread. Her answer, “Of Course”

Her assistants came rushing out as usual and grabbing my hand took me off to the Little Girl’s Store.

An hour later I was decked out in the prettiest lacy-est frilly Little Girl’s Party Dress. It was so little Girlish that it was humiliating. No Girl would wear it, let alone a sissy boy and not be embarrassed. I must admit though, I did like it very much and felt very Girlie in it.

I was led off into another room and as I entered all of Assistants to the Mistress yelled surprise. I had expected a lot of other little girls to play with, but all the Big Girls meant something else was planned.

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Fantasy Island – 9 “The Bridal Shower”

As I walked off the boat and up the Ramp the Mistress of Fantasy Island was waiting to greet me. With a smile, she asked me how she could help a Sissy like myself. I was humiliated as usual when she asked me like that, but with a stammer and a stutter I said that it was always my Dream to be a Bride and to be married to my Mistress.

She clapped her hands with glee and summoned several of her helpers. Looking at me, she said that before I became a Bride and before the Wedding, that of course there had to be a Bridal Shower.

They took me off to the Beauty Salon and started to prepare me for my Bridal Shower. As always I knew this was going to be embarrassing, but I wanted to be a Bride and a Bridal Shower was also a big part of my Dream. To be dressed up in a very feminine dress and to be given a Bridal Shower by all of my Mistress’s Girlfriends was both exciting and humiliating.

I exited the Salon and felt lovely as I was escorted to the Bridal Shower Reception at the local Restaurant. I paused before the doors were opened and I entered.

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Fantasy Island – 2 “A Pajama Party”

From the time I was young I always wanted to go the Girl’s Pajama Parties. They always seemed like they would be a lot of fun. I would hear my older Sister talk about the Pajama Parties she went to and how all the girls would wear pretty, frilly, lacy sexy Baby Doll Negligees. When my Sister had her Pajama Party I peaked and when I saw all her girl friends wearing those feminine Baby Dolls, I wished from that day to this that I would be invited to one. It never happened, since Pajama Parties were only things that girls did. I was so Jealous.

Naturally, when I had the opportunity to travel to Fantasy Island one of my first wishes was to attend a Girl’s Pajama Party. I was soon to regret my wish.

Mistress bought me a very feminine frilly red Baby Doll Negligee and frilly lace Panties. I got very excited about going to my first Girlie Negligee Party.

Until …………..

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sissy billy: Happy Year 2011 – Again

Well, here I am again celebrating Happy New Year 2011 – Again.

I have been a sissy client for quite some time now and I should know better, but I was lazy and lax and have not read the Rules and Regulations lately. Big Mistake. I know that I am supposed to upload all untouched photos for Mistress Katzenburg to review and pass judgement. I accomplished the hardest part of the activity – celebrating Happy New Year 2011 and failed to do the simplest of requirements and upload the photos.

I will now pay the price for forgetfulness and lack of focus of accomplishing all my tasks. And – the second time for any assignment is always more difficult. Depending on the mood of the Mistress and how bad a sissy is it can be really really bad. I guess a repeat of the assignment and one added assignment means I was really not that naughty, but I still have not been told what the “Whine and Cheese” means. I will find out.

Happy New Year 2011 to all again.

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sissy billy: Happy New Year

Over the years it seems that I have had a difficult time in progressing from my baby years to even an adolescent sissy. Mistress Katzenburg has deemed that I should start out the New Year as a brand new baby.

To start the year I am to put on my largest overstuffed diaper, put on my prettiest baby dress to celebrate my 0’th birthday, waddle and crawl around the house and then I will be put down for my baby’s nap. But, because I have been bad recently, when I take my nap I will have a special baby pacifier. The pacifier will be the biggest dildoe that Mistress Rosemarie has bought for me.

Happy New Year to all

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Her Last Visit

The last time that Mistress Amber visited for training, she though it would be a good idea to work on my “technique”. Apparently, one of the prerequisites for learning technique is not worrying about what is in your panties. Continue Reading

Maggie Rae: Suckswell Again

In my last assignment, I was instructed by Mistress Amber to dress as a sissy slut in bondage and orally service Ms. Lisa’s strap-on dildo—an assignment I took too lightly, neglecting to package my boy-parts and performing the entire assignment flat chested. Due to my negligence, my punishment was to first repeat the assignment—this time in proper form—before switching positions to service the sizable naughty-chair dildo while exposing my backside to Ms. Lisa for her to administer as she saw fit. It was to be a most unpleasant night of correction, however one I much deserved, and have learned a valuable lesson on thoroughness from…

The evening began with the transformation from wayward boy into sissy girl—Ms. Lisa had me try on a number of outfits before she settled on a bra-pantie set and a pink plaid skirt, perfect for allowing full rear access. My hair was done up into sweet little girl pigtails, and my face painted up to match the part. Once hair, makeup, and outfit were completed, we moved on to packaging up my boy-parts, which proved to be a bit of an adventure as—while the definition was clear—neither of us really had any clue as to exact technique. In keeping with the stipulations of “as uncomfortable as possible”, we selected an unfinished jute twine (a natural, very scratchy material) for the task and set about wrapping until everything was concealed below a bundle of scratchy lines. With my bits suitably buried, Ms. Lisa produced a pair of black water balloons to fill out the bra she had selected—they were a bit of a stretch, and the bra could only barely support them, but eventually she made them fit. She produced a length of rope and proceeded to bind my hands as a final bit of preparation before the punishment commenced in earnest.

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