Education of a Sissy - Ch 1. A Good Boy Has A Bad Idea

Printer-friendly version

Michael has come across something that implies that a company is doing a bad thing. Naturally, being a good boy, he decides to investigate.

Naturally, it doesn't work out the way he expected.

But then again, it's not going to go the way the bad guys expect either.

Introduction

This started of as a totally different project, and mutated to its current state.

A while back, I came across Xanderchan's "Girluminati" strip (If you want to read, start here), which, in my opinion, stops far too soon. This started out as an attempt to continue the comic strip, and then it mutated into a text story, and then half the characters got killed off because I didn't think they would work in the direction that I was taking this story, and then it continued mutating.

It's a sort of not at all NaNoWriMo story, in that I'm writing this as fast as I can with almost no editing, but I don't have a target word count, and there is not deadline for completion.


Current plans are for this to mostly be a bit of sexy fluff, but I do have plans to explore some of the darker areas of my universe, and to throw in a few bits that are totally unrelated to the actual story (as far as it has one - the characters can't even keep their names straight, let alone the plot).

For those who find this sort of thing interesting, this story was written using DropBox on a Nexus 7, Notesy on an iPhone 3GS, and Scrivener on a windows laptop.

A Good Boy Has A Bad Idea

"I think I'm going to have to give up, Mrs P," said Michael over the breakfast table. "I've done everything that I can think of that might get me into their offices. You can't get past reception unless you're expected, the building security is too tight, and there aren't any jobs that I can even pretend to apply for."

"There is one possibility that you have not considered," replied Mrs P, "though I suspect that it is one that you would find embarrassing and distasteful. You may have noticed that there are a number of sissies running around the building. I think there is actually a school there on one of the higher floors, and I think the new term just started. There should be no problems with an unknown sissy wandering around, getting lost and into all the wrong places. When I was young, my family was rather well known for its training of sissies, and I suspect that if you dress as one of them, you would almost certainly be considered to be just another lost sissy, and you could be walk straight past the reception desk with no problems."

"A sissy," said Michael, suddenly sounding very uncomfortable. "The orphanage was very strict about that sort of thing; it was regarded as a sin. I think there was one boy a couple of years ahead of me, who might have been a sissy, but they transferred him out shortly after I arrived."

"Yes, there are a number of people who can't seem to accept that people have different tastes, and that sissies aren't evil or dangerous. Anyway, the orphanages' opinion is irrelevant here. Are you brave and determined enough to get the information you want, that you will do this?"

"Given the behaviour of the warden, anything that he thinks is right is almost certainly wrong. Even so, this scares me,"

"If you're willing to try an experiment, I could help you get dressed as a sissy, and we can see how you look. If it doesn't work, you don't have to actually try it. If it does work, I think this will allow you to explore the entire office with no difficulties."

"If you're sure that it will work, I can't really see any reason for not trying. However, if I don't look good enough, I want you to be totally honest, and tell me."

"Of course," said Mrs P. "But from my experience, I would say that you would make an excellent sissy. While you finish breakfast, I'll have a look in the spare room for some stuff that I'm certain I brought with me when I moved. It was far too cute to dispose of."

For the next few minutes, Michael heard banging and shuffling noises coming from upstairs. When he had finished his breakfast, he went to the bottom of the stairs and called out, "Do you need any help?"

The response was "No need. Just make yourself comfortable in the sitting room." After a few minutes, the sounds stopped, and he heard Mrs P coming down the stairs. When she came through the door, she was carrying two cardboard boxes, which she placed on the table. "It's amazing the amount of stuff that I have up there. Such a pity that I'll probably never use it again." She paused few a few seconds, and then carried on. "Let's get you sorted out. First all, you need a shower." Opening one of the boxes, she pulled out of number of bottles. "A good wash, using all of these magic lotions. And when you come back here, I want you to be wearing these." From the box, she also pulled a silk negligee and...

"Panties? Girls panties?" queried Michael.

"If you're going to get away with this, you need to do everything that you can, and these will help you get in the mood"

Sighing, Michael picked up the bundle of clothes and the many bottles. In the shower, he sorted through the bottles and was appalled at the number of them. There was also a sheet a paper entitled "A Sissies Guide to Washing". Washing? Who needs to be told how to wash? Out of curiosity, he had a quick read.

  1. Wash hair with shampoo. Repeat if required.
  2. Apply conditioner. Work through thoroughly, and cover with shower cap.
  3. Wash face with scrub, avoiding delicate skin around eyes.
  4. Wash face with cleanser, paying attention to eyes.
  5. Wash body with body wash.
  6. Rinse conditioner out of hair.
  7. Towel dry hair, and fully dry body.
  8. Apply body lotion to all of your body. Use it sparingly, but cover all of your body below the neck. Ensure it is well worked in.
  9. Use towel to remove excess body lotion.
    10.Apply hair lotion sparingly, and ensure it is fully worked through hair.

"Good grief," though Michael, "is it really this complicated to wash? I suppose I should follow the list. Why else would it be here?"

After what seemed like a long time, and a lot of effort, Michael was washed and dried, and was contemplating getting dressed. The panties were plain cotton, and apart from the large quantities of lace on the back, didn't seem that different from the normal man's pants he wore. The robe, on the other hand, was a slippery gold satin, and he found himself simultaneously fearing and desiring it. Until now, he hadn't really thought about what he was about to do. The shower had been more complicated than usual, but that had been it. Now, he had to make the decision. Was he to pretend to be a sissy? Was the information he was after important enough for him to do what he had been taught was a sin? He shivered, not sure if it was the cold after the warm shower or the prospect that lay before him.

It was a sin, but, in all likelihood, he wouldn't be able to pass a sissy, and he could simply pretend that it had never happened. He slowly slipped the robe on, the satin sliding over his skin caused shivers to run through his body, and he got flashes of the scent from the lotion that he applied just a few moments before. He paused for a few seconds, then wrapped the robe around himself, doing up the bow on the front with a decisive tug.

There had been some changes in the sitting room - the contents of the boxes had been unpacked into the table, and one of the reclining chairs had been moved to beside it.

"I don't have the time or stuff to do the full makeover, but I'm sure I'll be able to do enough that everyone will know you're a sissy. If you'll sit down, I'll get started." When Michael was seated, Mrs P started playing around with his hair. "You don't have a lot of hair, but I can get something suitable about it." Michael could feel her pulling at his hair as she did things that he could not see.

After a few minute, she said, "That should do," and placed a cap over his hair. With a click and a whir, the cap filled with warm air. "While your hair dries, I'll give your face a good going over. I doubt that you have ever had it properly cleansed."

The chair slowly tilted, and Michael found himself lying back, staring upwards at Mrs P and the ceiling. As she gently ministered to his face, he found the feeling of her fingers and the warm air both relaxing and arousing. He hoped that she wouldn't notice the erection that was slowly starting to fill his panties. He was on the verge of sleep, when he heard "There, we'll leave that for a few moments while I do your nails."

When Mrs P looked at his nails, she said, "You're not taking proper care of your nails. Everyone should, it shows you care."

For the next few minutes, Michael could feel the nail file rasping and shaping his nails. He then felt a cold liquid on his hand, that quickly warmed up as Mrs P massaged it in. "There, definitely the nails of someone who cares how they look. You'll be amazed at how this can change people's opinions of you, without them realising why. Hold still now, the polish is very delicate to apply." Michael looked down, where his nails were changing colour under the influence of the brush that his landlady was wielding. For some reason, he felt a bit disappointed that she wasn't using a bright red. "I'm using soft pink," she said, as if reading his mind, "as it's more appropriate for what you'll be wearing. A brighter colour is reserved for evenings or when you want to stand out from the crowd, which I doubt you want to do today." After a few more minutes, the task was complete. "We just leave that to dry now, and we'll see what else needs to be done."

Michael found himself shivering again, as Mrs P ran her hands over his legs. "Hmm. You don't have a lot of hair, do you? That will make things a lot easier, but let us finish with your facial."

"I think your nails are dry enough now - as long as you're careful, you shouldn't cause any noticeable damage. We can start getting you dressed." Removing the hair dryer cap, Mrs P freed him from the chair. "First, let's start with socks and shoes." Michael was handed a bundle, which he found to consist of a pair of low-heeled shoes in black patent, and socks. Putting the shoes on the table, he unfolded the socks, and found that they were long, white cotton.

After rolling one of the socks down to a little bundle, he stood on one leg, and attempted to unroll the sock up the other leg. After a lot of jumping around, Mrs P suggested that he sit down on the edge of one of the chairs, and start again. This time Michael found that he could actually manage to unroll the sock up his leg, but he was surprised at how far up his leg the sock went.

"Thigh highs," said Mrs P in response. "I don't think you'd appreciate tights, and with these, if your skirts flip in the breeze, you won't show anything you don't want to."

After Michael had donned both socks, Mrs P passed him the shoes. "Mary Jane's, the classic sissy shoe. The heel is low enough that you should have no problems walking." Mrs P continued in a wistful voice, "I used to love teaching sissies to walk in heels, the way they would grow from gawky, awkward colts, barely staying upright up as they attempted to walk in the lowest of heels, to poetry in motion, as they dance their way around the ballroom in the tallest and spikiest of stilettos."

"I won't make you wear a bra. For many sissies, their first bra is one of the big moments in becoming a sissy, and we we're not going there, yet. The dress I have chosen for you is quite a simple one, suitable for a young sissy who is just starting out. It's really a bit young for you, but with suitable makeup, you'll look the part."

Mrs P held up the dress for Michael to view. It was all in pink, soft pink cotton, with clusters of flowers embroidered into the fabrics. It had a high neckline, elbow length sleeves, and a knee length skirt that was held out by several petticoats. Around the neck, sleeves cuffs, waist and skirt were layers of white lace. It was most definitely not the sort of thing that Michael had ever contemplated that he would be wearing. In fact, he should really be doing just about anything to get out of wearing it, instead of sort of wondering what it would be like.

With a quick flick that defied Michael's eyes, Mrs P was holding the dress out, ready for him to put on. "Hold your hands out in from of you, and I'll slip this on." Raising his arms in front, Michael found himself enveloped in the skirts and petticoats of the dress. He felt a scratching on his arms from the lace of the petticoats that was quickly replaced by the soft feel of cotton. There came the soft smell of a rose perfume, and a sudden burst of light as his head shot through the collar of the dress. "OK," said Mrs P, "hands by your side, and stand up straight. Let's gets a good look at you."

Blinking a little, Michael look down. All he could see was pink and white. The skirts of the dress stood out around him, blocking the view of his feet, except where his squashed the skirt down, forcing the slightly scratchy lace against his thighs, bare above the long socks. "Can I have a look in the mirror, Mrs P? I want to see what I look like."

"I think you should wait until you're completely ready. At the moment, there are still things to do, and you would get totally the wrong idea of what you look like." Taking him gently by the shoulders, Mrs P spun Michael around on the spot to face away from her, and took hold of the dresses zip. Slowly, she pulled it up, and Michael could hear the slow rasp as the zip worked its way up, and the dress tightened around him.

Spinning him round again, Mrs P stood back, and looked at Michael. He could see that she had an odd look on her face, but he could not work out what it was. "Yesss," she said, "that dress is just about perfect on you. I just need to figure out what to do with your hair. It's far too short for a sissy, and I don't think I have a suitable wig." Michael kept his hair short, partly due to the way he had been brought up by the orphanage, and partly because long hair had made him looked girlish. "Maybe I can make use of its shortness, use it as a contrast to the rest ..."

Mrs P made Michael sit down again, and started attacking his hair with all kinds of mysterious implements and unguents. He could feel her pulling his hair in all directions, and she repeatedly stood back, looked at him, and started in again. Eventually, when she stood back, she nodded to herself, and smiled. "You know," she said, "if it wasn't for the fact that a sissy would have a panic attack if you suggested that she cut her hair, that style could almost start a new fashion trend."

"Just let me do your makeup, and I think you'll be ready for your debut." Mrs P dived in again, this time wielding brushes and sponges, and applying the mysterious unguents to his face. She muttered quietly to herself, and Michael picked up the odd phrase. "Perfect skin." "A bit heavy on the blusher, but we're not going for natural today." Michael nearly ran when she approached his eye with what looked like torture instruments, but all she said was "eyelashes to die for."

Eventually, Michael got the feeling that she was slowing down, and nearing completion of the masterpiece she was working on. For the final time, Mrs P stepped back, and had a long slow look up and down, up and down. "Perfect. Not quite the conventional sissy, not with that hair, but I doubt that anyone would think anything but."

Standing Michael up, Mr P said "Let's do the big reveal scene, and let you see your new self." She moved Michael to in front of a large mirror that had been covered up by a piece of cloth. "Are you ready?" she asked, preparing to pull the cloth aside. "Hold one, there's just one thing needed." Darting over to the pile of clothing on the table, she dug through it, and pulled out a pair of lace gloves. "The final touch." The fingerless gloves were made of a white lace that matched that of the dress, and had frills around the wrist. Crossing Michaels hand in front of him, one hand holding the other wrist, she walked back to the mirror. "Ready?" she asked again, and pulled the cloth aside.

All Michael could do was stare at the mirror. This could not be him. There was no way that this could be him. This was not the slightly scruffy 21 year old that he was used to seeing in the mirror. This was a young girl, in her mid-teens, 17 at most, and she was stunning.

After a few moments, Michael found that he could do more than simply drink in the image, and he could actually look at himself. The most obvious item was the dress. When he had looked down at the dress, it had seemed far too bright a pink, the pattern had been far too obtrusive, and the skirts had seemed massive. In the mirror, it was different. The white lace toned down the pink, and the pattern receded a bit into the background. The skirts still stood out further than he was happy with, but nowhere as far as they had seemed.

At first sight, the makeup seemed overdone, but he could sort of see what Mrs P had been aiming at. The colours were brighter than he was used to seeing on women, and his cheekbones had been quite emphasised. It was a bit like a little girl had been let loose in her mother's makeup, but it fit perfectly with the dress and his hair.

His hair. It was still short. Far too short for the dress and makeup. It was as if the little girl had rebelled against being made to dress up, and had cut all her hair off, and yet the result was incredibly cute. Its very shortness and lack of femininity emphasised the girlishness of the rest of the image.

Mrs P started crying. "It's amazing. I've never seen anything like it." She rushed over, and embraced Michael in a strong hug. After a while, she let him go, and said "I think there's absolutely no doubt that no-one would doubt that you are a sissy. Just a few quick lessons on behaviour, and I think you will be ready to go."

"The most essential thing is your walk. The heels on your shoes should ensure that you are aware of your walk, but you will still need to modify it slightly. The key is to take smaller steps, and to try to walk as if you are on a tight-rope, one foot in front of the other, rather than side by side."

Mrs P made Michael walk up and down the room, until she was satisfied with his walk. As he walked around the room, Michael could hear a rustling from the petticoats under his skirts. The sound varied with his walk, and he soon learnt when it sounded correct, and when it indicated that he was walking in the wrong manner.

When he complained that the walk was slow, Mrs P replied, "Speed is not important, style is. A sissy never runs, and never appears to hurry. If you do need do need to move quickly, smaller, but faster steps will enable you to move faster than people realise"

"Finally, check your make-up regularly, even if you know it's perfect. This gives you a pause, a chance to think. If you're nervous on the street, this gives you a reason to stop, to step out of the flow of people, and let them all go pass. Knowing your make-up is perfect adds to your confidence, and lipstick nearly always needs redoing."

After what seemed liked miles of walking, and thousands of glances into a pocket mirror, Mrs P finally said, "I think you're finally ready." Seeing the look of panic suddenly blooming on Michaels face, she added, "You're looking good. I doubt that anyone will see anything other than a rather pretty, young sissy." When Michael didn't look any better, she continued, "You don't have to go out. There's nothing forcing you to do this."

"No, I do have to. If I don't I'll never be able to live with myself."

"OK. In which case, I think you should go now, before you get too scared. Do you have everything you need? Money, keys, whatever it is you need to get the information?"

"Yes it's all in the..." Before Michael could complete the sentence, Mrs P had the front door open, and her hand on his back was gently urging him out into the street. The last thing he heard was a "Good luck" as the door closed behind him.

up
127 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos